Styryl phenol-based surfactants for hydrocarbon recovery

Abstract

Described herein are compounds and surfactant mixtures (as well as the resulting compositions) for use in oil and gas operations. Also provided are compounds of Formula I, II, III, IIIA, IV, IVA, V, VI, VII, VIIA, VIII, VIIIA, IX, IXA, IXB, IXC, IXD, X, XA, XB, XC, XD, XI, XIA, XIB, XIC, XID, XII, XIIA, XIIB, XIIC, and XIID.

Description

[0001] STYRYL PHENOL-BASED SURFACTANTS FOR HYDROCARBON RECOVERY

[0002] CROSS-REFERENCE TO RELATED APPLICATION

[0003] This application claims benefit of priority of U.S. Provisional Application 63 / 536,035, filed on August 31, 2023, the contents of which is hereby incorporated herein in its entirety.

[0004] BACKGROUND

[0005] Enhanced oil recovery (EOR) is an increasingly important supplemental technique for recovering oil from a reservoir after primary and secondary recovery. Many hydrocarbon reservoirs trap a significant amount of oil that is bound tightly and difficult to remove by traditional water flooding methods. There is an ongoing need to develop cost-effective and improved additives for oil recovery from hydrocarbon reservoirs, including those with heavy oil and / or high asphaltene concentrations.

[0006] SUMMARY

[0007] Provided herein are compounds and surfactant mixtures, as well as compositions comprising these compounds and surfactant mixtures. Also provided are methods of using these compounds, mixtures, and compositions in oil and gas operations.

[0008] Described herein are compounds of Formula I or salt thereof:

[0009] R2-R5are each independently H or -SO3;

[0010] R6-R9and R12-R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0011] R10is H, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A; alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate;

[0012] BO represents -CH2-CH(ethyl)-O-;

[0013] EO represents -CH2-CH2-O-;

[0014] PO represents -CH2-CH(methyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; n, m, p, and q are each independently 0 to 6; the dotted line represents an optional double bond if valence permits; at least two of R]-R9, R12-R17or A are independently -SO3; and wherein when: , one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl.

[0015] Also described herein are compounds of Formula II or salt thereof:

[0016] Formula II wherein:

[0017] R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;

[0018] R2-R4are each independently H or -SO3;

[0019] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate;

[0020] EO represents -CH2-CH2-O-;

[0021] PO represents -CH2-CH(methyl)-O-;

[0022] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R'-R4, R16, R17, or A are independently -SO3.

[0023] Also described herein are compounds of Formula III or salt thereof:

[0024] wherein:

[0025] R2, R3, and R5are each independently H or -SO3;

[0026] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate;

[0027] EO represents -CH2-CH2-O-;

[0028] PO represents -CH2-CH(methyl)-O-;

[0029] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2, R3, R5, R16, R17, or A are independently -SO3.

[0030] Also described herein are compounds of Formula IV or salt thereof: R2, R3, and R5are each independently H or -SO3;

[0031] R6-R8, and R12-R14are each independently H, -OH, -SO3, or C1-C6alkyl;

[0032] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=Cf b), monocarboxylate, dicarboxylate, or tricarboxylate;

[0033] EO represents -CH2-CH2-O-;

[0034] PO represents -CH2-CH(methyl)-O-;

[0035] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R1, R3, R5-R8, R12-R14, R16, R17, or A are independently -SO3; wherein when: one of R6or R12is -SO3. then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0036] Also described herein are compounds of Formula V or salt thereof:

[0037] Formula V wherein: R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;

[0038] R2-R4are each independently H or -SO3;

[0039] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate;

[0040] EO represents -CH2-CH2-O-;

[0041] PO represents -CH2-CH(methyl)-O-;

[0042] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R]-R4, R16, R17, or A are independently -SO3.

[0043] Also described herein are compounds of Formula VI or salt thereof: wherein:

[0044] R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;

[0045] R2-R4are each independently H or -SO3;

[0046] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0047] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate , or tricarboxylate;

[0048] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0049] EO represents -CH2-CH2-O-;

[0050] PO represents -CH2-CH(methyl)-O-;

[0051] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R]-R4, R6, R7, R9, R12, R13, R15-R17or A are independently -SO3; wherein when: one of R6or R12is -SO3. then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3. then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0052] Also described herein are compounds of Formula VII or salt thereof: wherein:

[0053] R2-R4are each independently H or -SO3; A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CHi), monocarboxylate, dicarboxylate, or tricarboxylate;

[0054] EO represents -CH2-CH2-O-;

[0055] PO represents -CH2-CH(methyl)-O-;

[0056] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R16, R17, or A are independently -SO3.

[0057] Also described herein are compounds of Formula VIII or salt thereof: wherein:

[0058] R2-R4are each independently H or -SO3;

[0059] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0060] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate;

[0061]

[0062] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0063] EO represents -CH2-CH2-O-;

[0064] PO represents -CH2-CH(methyl)-O-;

[0065] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R6, R7, R9, R12, R13, R15-R17or A are independently -SO3; wherein when: one of R6or R12is -SO3. then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3. then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0066] Also described herein are compounds of Formula IX or salt thereof, Formula IXA or salt thereof, Formula IXB or salt thereof, Formula IXC or salt thereof, or Formula IXD or salt thereof:

[0067] Formula IXD wherein:

[0068] R2-R4are each independently H or -SO3;

[0069] R6, R7, R9and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0070] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate;

[0071] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0072] BO represents -CH2-CH(ethyl)-O-;

[0073] EO represents -CH2-CH2-O-;

[0074] PO represents -CH2-CH(methyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; n, m, and q are each independently 0 to 6; the dotted line represents an optional double bond if valence permits; at least two of R2-R7, R9, R12-R13, R15-R17, or A are independently -SO3; and wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl.

[0075] Also described herein are compounds of Formula X or salt thereof, Formula XA or salt thereof, Formula XB or salt thereof, Formula XC or salt thereof, or Formula XD or salt thereof:

[0076]

[0077] Formula XD; wherein:

[0078] R2-R4are each independently H or -SO3; A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate; EO represents -CH2-CH2-O-;

[0079] PO represents -CH2-CH(methyl)-O-;

[0080] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R16, R17, or A are independently -SO3.

[0081] Also described herein are compounds of Formula XI or salt thereof, Formula XIA or salt thereof, Formula XIB or salt thereof, Formula XIC or salt thereof, or Formula XID or salt thereof:

[0082]

[0083] Formula XID wherein:

[0084] R2-R4are each independently H or -SO3;

[0085] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate; BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R16, R17, or A are independently -SO3.

[0086] Also described herein are compounds of Formula XII or salt thereof, Formula XIIA or salt thereof, Formula XIIB or salt thereof, Formula XIIC or salt thereof, or Formula XIID or salt thereof: R2-R4are each independently H or -SO3;

[0087] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0088] A is -OR16, -OH, -OSO3, -SO3, alkene (e.g., -CH=CH2), monocarboxylate, dicarboxylate, or tricarboxylate;

[0089] EO represents -CH2-CH2-O-;

[0090] PO represents -CH2-CH(methyl)-O-;

[0091] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R]-R4, R6, R7, R9, R12, R13, R15-R17or A are independently -SO3; wherein when: one of R6or R12is -SO3. then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0092] Also described herein are surfactant mixtures including: a) a compound of Formula I or salt thereof:

[0093] c) a compound of Formula III or salt thereof or a compound of Formula IIIA or salt

[0094] 5 thereof:

[0095] d) a compound of Formula IV or salt thereof or a compound of Formula IVA or salt

[0096] 5 thereof:

[0097]

[0098] 5 combination thereof; e) a compound of Formula V or salt thereof:

[0099] g) a compound of Formula VII or salt thereof or Formula VIIA or salt thereof: or any combination thereof; h) a compound of Formula VIII or salt thereof or Formula VIIIA or salt thereof:

[0100] or any combination thereof; i) a compound of Formula IX or salt thereof, Formula IXA or salt thereof, Formula IXB or salt thereof, Formula IXC or salt thereof, Formula IXD or salt thereof: or any combination thereof; j) a compound of Formula X or salt thereof, Formula XA or salt thereof, Formula XB or salt thereof, Formula XC or salt thereof, or Formula XD or salt thereof:

[0101]

[0102] 5 k) a compound of Formula XI or salt thereof, Formula XIA or salt thereof, Formula XIB or salt thereof, Formula XIC or salt thereof, or Formula XID or salt thereof:

[0103] 1) a compound of Formula XII or salt thereof, Formula XIIA or salt thereof, Formula XIIB or salt thereof, Formula XIIC or salt thereof, or Formula XIID or salt thereof:

[0104] EO represents -CH2-CH2-O-;

[0105] PO represents -CH2-CH(methyl)-O-;

[0106] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; at least two of R]-R9, R12-R17or A are independently -SO3; and when: one of R6or R12is -SO3. then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3. then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; or any combination thereof.

[0107] Also described herein are compositions including water and a compound described herein, a surfactant mixture described herein, or any combination thereof. In some embodiments, the composition can further include water, a co- surfactant, co-solvent, a friction reducer, a gelling agent, a crosslinker, a breaker, a pH adjusting agent, a non-emulsifier agent, an iron control agent, a corrosion inhibitor, a scale inhibitor, a biocide, a clay stabilizing agent, a chelating agent, a proppant, a wettability alteration chemical, or any combination thereof.

[0108] Also described herein are methods of using the compounds and surfactant mixtures as described herein (as well as the resulting compositions) in oil and gas operations. The oil and gas operation can comprise for example, an enhanced oil recovery (EOR) operation (e.g., an improved oil recovery (IOR) operation, a surfactant (S) flooding operation, an alkaline- surfactant (AS) flooding operation, a surfactant-polymer (SP) flooding operation, a alkaline- surfactant-polymer (ASP) flooding operation, or any combination thereof) a hydraulic fracturing operation, a wellbore clean-up operation,, or any combination thereof.

[0109] Provided herein are also methods of preventing asphaltene aggregation in a formation comprising: contacting a hydrocarbon containing asphaltene with a compound described herein, a surfactant mixture described herein, a composition described herein, a styryl phenol sulfonate compound, or any combination thereof.

[0110] Provided herein are also methods for treating a formation, the method comprising: introducing an aqueous fluid comprising water and a compound described herein, a surfactant mixture described herein, a composition described herein, or any combination thereof through a wellbore into the formation. In some embodiments, a hydrocarbon in the formation can include an asphaltene concentration of from 0.5% to 17%.

[0111] The details of one or more embodiments of the disclosure are set forth in the accompanying drawings and the description below. Other features, objects, and advantages of the disclosure will be apparent from the description and drawings, and from the claims.

[0112] DESCRIPTION OF DRAWINGS

[0113] FIGs. 1A-1B are images showing the phase behavior of (FIG. 1 A) basic formulation and basic formulation with 0.3% TSP-polySOa and (FIG. IB) basic formulation and basic formulation with 0.3% TSP 16EO-polySO3.

[0114] FIG. 2 is a graph illustrating core flood experiments using control formulation: 0.45% ISO, 0.50% nonionic, and 1.40% EGBE; and TSP formulation: 0.45% ISO, 0.50% nonionic, TSP-poly sulfonate, and 1.40% EGBE.

[0115] FIG. 3 is an image showing the solubility of 0.5% surfactants in DI water with TSP:H2SO4of 1 : 1, 1 :3, and 1:5.

[0116] FIG. 4 is a synthetic scheme illustrating the generation of tristyrenated phenol (TSP) sulfonates.

[0117] FIG. 5A-5D are13C NMR profiles for (FIG. 5A) TSP, (FIG. 5B) TSP-SO3at a ratio of 1 :1, (FIG. 5C) TSP-SO3at a ratio of 1 :3, and (FIG. 5D) TSP-SO3at a ratio of 1:5.

[0118] FIG. 6A-6D are1H NMR profiles for (FIG. 6A) TSP, (FIG. 6B) TSP-SO3at a ratio of 1 :1, (FIG. 6C) TSP-SO3at a ratio of 1 :3, and (FIG. 6D) TSP-SO3at a ratio of 1:5.

[0119] FIG. 7A-7B are HPLC profiles for TSP and TSP:H2SO4at a ratio of 1:1 after (7 A) 3 hours and (7B) 20 hours. FIG. 8A-8B are HPLC profiles for TSP and TSP:H2SO4at a ratio of 1 :3 after (8A) 3 hours and (8B) 20 hours.

[0120] FIG. 9A-9B are HPLC profiles for TSP and TSPU FSCU at a ratio of 1:5 after (9 A) 3 hours and (9B) 20 hours.

[0121] FIG. 10 is an HPLC profile for TSP:H2SO4at a ratio of 1:1 and 1:5.

[0122] FIG. 11 is an HPLC profile for TSP and TSP:H2SO4 at a ratio of 1 :1, 1:3, and 1 :5.

[0123] FIG. 12 is a synthetic scheme illustrating the generation of tristyryl phenol 16EO sulfonates.

[0124] FIG. 13A-13B are13C NMR profiles for (FIG. 13A) TSP-16EO, (FIG. 13B) TSP-16EO- SO3 / SO4.

[0125] FIG. 14A-14B are]H NMR profiles for (FIG. 14A) TSP-16EO, (FIG. 14B) TSP-16EO- SO3 / SO4.

[0126] FIG. 15 is an HPLC profile for TSP-16EO, and TSP-16EO-polysulfonate.

[0127] FIG. 16 is a proposed synthetic scheme illustrating the generation of tristyryl phenol EO.

[0128] FIG. 17 is a proposed synthetic scheme illustrating the generation of tristyrenated phenol.

[0129] FIG. 18 is an HPLC profile for TSP-35PO-30EO and TSP-35PO-30EO-poIysulfonate.

[0130] FIG. 19 is an image showing the aqueous stability 0.5% TSP polysulfonate compared to 0.5% TSP in deionized water.

[0131] FIG. 20 is an image showing the aqueous stability 0.5% TSP-16EO polysulfonate compared to 0.5% TSP-16EO in 11% NaCl solution at 76°C.

[0132] FIG. 21 is an image showing the aqueous stability of 0.5% TSP-35PO-30EO polysulfonate compared to 0.5% TSP-35PO-30EO in 22% solution at 76°C.

[0133] Like reference symbols in the various drawings indicate like elements.

[0134] DETAILED DESCRIPTION

[0135] A number of embodiments of the disclosure have been described. Nevertheless, it will be understood that various modifications may be made without departing from the spirit and scope of the invention. Accordingly, other embodiments are within the scope of the following claims.

[0136] Definitions

[0137] To facilitate understanding of the disclosure set forth herein, a number of terms are defined below. Unless defined otherwise, all technical and scientific terms used herein generally have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. Unless otherwise specified, all percentages are in weight percent and the pressure is in atmospheres. All citations referred to herein are expressly incorporated by reference.

[0138] General Definitions

[0139] As used in this specification and the following claims, the terms “comprise” (as well as forms, derivatives, or variations thereof, such as “comprising” and “comprises”) and “include” (as well as forms, derivatives, or variations thereof, such as “including” and “includes”) are inclusive (i.e., open-ended) and do not exclude additional elements or steps. For example, the terms "comprise" and / or "comprising," when used in this specification, specify the presence of stated features, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof. Other than where noted, all numbers expressing quantities of ingredients, reaction conditions, geometries, dimensions, and so forth used in the specification and claims are to be understood at the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, to be constmed in light of the number of significant digits and ordinary rounding approaches.

[0140] Accordingly, these terms are intended to not only cover the recited element(s) or step(s), but may also include other elements or steps not expressly recited. Furthermore, as used herein, the use of the terms “a”, “an”, and “the” when used in conjunction with an element may mean “one,” but it is also consistent with the meaning of “one or more,” “at least one,” and “one or more than one.” Therefore, an element preceded by “a” or “an” does not, without more constraints, preclude the existence of additional identical elements.

[0141] Ranges can be expressed herein as from “about” one particular value, and / or to “about” another particular value. By “about” is meant within 10% of the value, e.g., within 9, 8, 7, 6, 5, 4, 3, 2, or 1% of the value. When such a range is expressed, another aspect includes from the one particular value and / or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as “about” that particular value in addition to the value itself. For example, if the value “10” is disclosed, then “about 10” is also disclosed. A range may be construed to include the start and the end of the range. For example, a range of 10% to 20% (i.e., range of 10%-20%) can includes 10% and also includes 20%, and includes percentages in between 10% and 20%, unless explicitly stated otherwise herein.

[0142] As used herein, the terms "may," "optionally," and "may optionally" are used interchangeably and are meant to include cases in which the condition occurs as well as cases in which the condition does not occur. Thus, for example, the statement that a formulation "may include an excipient" is meant to include cases in which the formulation includes an excipient as well as cases in which the formulation does not include an excipient.

[0143] It is understood that when combinations, subsets, groups, etc. of elements are disclosed (e.g., combinations of components in a composition, or combinations of steps in a method), that while specific reference of each of the various individual and collective combinations and permutations of these elements may not be explicitly disclosed, each is specifically contemplated and described herein. By way of example, if a composition is described herein as including a component of type A, a component of type B, a component of type C, or any combination thereof, it is understood that this phrase describes all of the various individual and collective combinations and permutations of these components. For example, in some embodiments, the composition described by this phrase could include only a component of type A. In some embodiments, the composition described by this phrase could include only a component of type B. In some embodiments, the composition described by this phrase could include only a component of type C. In some embodiments, the composition described by this phrase could include a component of type A and a component of type B. In some embodiments, the composition described by this phrase could include a component of type A and a component of type C. In some embodiments, the composition described by this phrase could include a component of type B and a component of type C. In some embodiments, the composition described by this phrase could include a component of type A, a component of type B, and a component of type C. In some embodiments, the composition described by this phrase could include two or more components of type A (e.g., Al and A2). In some embodiments, the composition described by this phrase could include two or more components of type B (e.g., Bl and B2). In some embodiments, the composition described by this phrase could include two or more components of type C (e.g., Cl and C2). In some embodiments, the composition described by this phrase could include two or more of a first component (e.g., two or more components of type A (Al and A2)), optionally one or more of a second component (e.g., optionally one or more components of type B), and optionally one or more of a third component (e.g., optionally one or more components of type C). In some embodiments, the composition described by this phrase could include two or more of a first component (e.g., two or more components of type B (Bl and B2)), optionally one or more of a second component (e.g., optionally one or more components of type A), and optionally one or more of a third component (e.g., optionally one or more components of type C). In some embodiments, the composition described by this phrase could include two or more of a first component (e.g., two or more components of type C (Cl and C2)), optionally one or more of a second component (e.g., optionally one or more components of type A), and optionally one or more of a third component (e.g., optionally one or more components of type B).

[0144] The term “enhanced oil recovery” refers to techniques for increasing the amount of unrefined petroleum (e.g., crude oil) that may be extracted from an oil reservoir. Using EOR, more of the reservoir's original oil can typically be extracted compared with only using primary and secondary recovery (e.g., by water injection or natural gas injection). Enhanced oil recovery may also be referred to as improved oil recovery or tertiary oil recovery (as opposed to primary and secondary oil recovery). Examples of EOR operations include, for example, miscible gas injection (which includes, for example, carbon dioxide flooding), chemical injection (sometimes referred to as chemical enhanced oil recovery (CEOR), and which includes, for example, polymer flooding, alkaline flooding, surfactant flooding, as well as combinations thereof such as alkaline-polymer flooding or alkaline-surfactant-polymer flooding), In some embodiments, the EOR operation can include a polymer (P) flooding operation, an alkaline-polymer (AP) flooding operation, a surfactant-polymer (SP) flooding operation, an alkaline-surfactant-polymer (ASP) flooding operation, or any combination thereof. The terms “operation” and “application” may be used interchangeability herein, as in EOR operations or EOR applications. Other operations can also be performed on subterranean formations to facilitate hydrocarbon recovery, such as thermal recovery operations (including, for example, cyclic steam and steam flooding).

[0145] The term “hydrocarbon” refers to a compound containing only carbon and hydrogen atoms.

[0146] “Hydrocarbon-bearing formation” or simply “formation” refers to the rock matrix in which a wellbore may be drilled. For example, a formation refers to a body of rock that is sufficiently distinctive and continuous such that it can be mapped. It should be appreciated that while the term “formation” generally refers to geologic formations of interest, that the term “formation,” as used herein, may, in some instances, include any geologic points or volumes of interest (such as a survey area).

[0147] “Unconventional formation” is a subterranean hydrocarbon-bearing formation that generally requires intervention in order to recover hydrocarbons from the reservoir at economic flow rates or volumes. For example, an unconventional formation includes reservoirs having an unconventional microstructure in which fractures are used to recover hydrocarbons from the reservoir at sufficient flow rates or volumes (e.g., an unconventional reservoir generally needs to be fractured under pressure or have naturally occurring fractures in order to recover hydrocarbons from the reservoir at sufficient flow rates or volumes).

[0148] In some embodiments, the unconventional formation can include a reservoir having a permeability of less than 25 millidarcy (mD) (e.g., 20 mD or less, 15 mD or less, 10 mD or less, 5 mD or less, 1 mD or less, 0.5 mD or less, 0. 1 mD or less, 0.05 mD or less, 0.01 mD or less, 0.005 mD or less, 0.001 mD or less, 0.0005 mD or less, 0.0001 mD or less, 0.00005 mD or less, 0.00001 mD or less, 0.000005 mD or less, 0.000001 mD or less, or less). In some embodiments, the unconventional formation can include a reservoir having a permeability of at least 0.000001 mD (e.g., at least 0.000005 mD, at least 0.00001 mD, 0.00005 mD, at least 0.0001 mD, 0.0005 mD, 0.001 mD, at least 0.005 mD, at least 0.01 mD, at least 0.05 mD, at least 0.1 mD, at least 0.5 mD, at least 1 mD, at least 5 mD, at least 10 mD, at least 15 mD, or at least 20 mD).

[0149] The unconventional formation can include a reservoir having a permeability ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the unconventional formation can include a reservoir having a permeability of from 0.000001 mD to 25 mD (e.g., from 0.001 mD to 25 mD, from 0.001 mD to 10 mD, from 0.01 mD to 10 mD, from 0.1 mD to 10 mD, from 0.001 mD to 5 mD, from 0.01 mD to 5 mD, or from 0.1 mD to 5 mD). When referring to a permeability value of a formation, the permeability value can comprise an average value for the permeability of samples across a region of the formation.

[0150] The formation may include faults, fractures (e.g., naturally occurring fractures, fractures created through hydraulic fracturing, etc.), geobodies, overburdens, underburdens, horizons, salts, salt welds, etc. The formation may be onshore, offshore (e.g., shallow water, deep water, etc.), etc. Furthermore, the formation may include hydrocarbons, such as liquid hydrocarbons (also known as oil or petroleum), gas hydrocarbons, a combination of liquid hydrocarbons and gas hydrocarbons (e.g., including gas condensate), etc.

[0151] The formation, the hydrocarbons, or both may also include non- hydrocarbon items, such as pore space, connate water, brine, fluids from enhanced oil recovery, etc. The formation may also be divided up into one or more hydrocarbon zones, and hydrocarbons can be produced from each desired hydrocarbon zone.

[0152] The term formation may be used synonymously with the term “reservoir” or “subsurface reservoir” or “subsurface region of interest” or “subsurface formation” or “subsurface volume of interest” or “subterranean formation”. For example, in some embodiments, the reservoir may be, but is not limited to, a shale reservoir, a carbonate reservoir, a tight sandstone reservoir, a tight siltstone reservoir, etc. Indeed, the terms “formation,” “hydrocarbon,” and the like are not limited to any description or configuration described herein.

[0153] A “wellbore” refers to a single hole, usually cylindrical, that is drilled into a subsurface volume of interest. A wellbore may be drilled in one or more directions. For example, a wellbore may include a vertical wellbore, a horizontal wellbore, a deviated wellbore, and / or other type of wellbore. A wellbore may be drilled in the formation for exploration and / or recovery of resources. For example, a wellbore may be drilled in the formation to aid in extraction and / or production of resources such as hydrocarbons. As another example, a wellbore may be drilled in the formation for fluid injection. A plurality of wellbores (e.g., tens to hundreds of wellbores) are often used in a field depending on the desired outcome.

[0154] A wellbore may be drilled into a formation using practically any drilling technique and equipment known in the art, such as geosteering, directional drilling, etc. Drilling the wellbore may include using a tool, such as a drilling tool that includes a drill bit and a drill string. Drilling fluid, such as drilling mud, may be used while drilling in order to cool the drill tool and remove cuttings. Other tools may also be used while drilling or after drilling, such as measurement-while-drilling (MWD) tools, seismic-while-drilling (SWD) tools, wireline tools, logging-while-drilling (LWD) tools, or other downhole tools. After drilling to a predetermined depth, the drill string and the drill bit may be removed, and then the casing, the tubing, and / or other equipment may be installed according to the design of the wellbore may be installed according to the design of the wellbore. The equipment to be used in drilling the wellbore may be dependent on the design of the wellbore, the formation, the hydrocarbons, and / or other factors. A wellbore may include a plurality of components, such as, but not limited to, a casing, a liner, a tubing string, a sensor, a packer, a screen, a gravel pack, artificial lift equipment (e.g., an electric submersible pump (ESP)), and / or other components. If a wellbore is drilled offshore, the wellbore may include one or more of the previous components plus other offshore components, such as a riser. A wellbore may also include equipment to control fluid flow into the wellbore, control fluid flow out of the wellbore, or any combination thereof. For example, a wellbore may include a wellhead, a choke, a valve, and / or other control devices. These control devices may be located on the surface, in the subsurface e.g., downhole in the wellbore), or any combination thereof. In some embodiments, the same control devices may be used to control fluid flow into and out of the wellbore. In some embodiments, different control devices may be used to control fluid flow into and out of a wellbore. In some embodiments, the rate of flow of fluids through the wellbore may depend on the fluid handling capacities of the surface facility that is in fluidic communication with the wellbore. The equipment to be used in controlling fluid flow into and out of a wellbore may be dependent on the wellbore, the formation, the surface facility, and / or other factors. Moreover, sand control equipment and / or sand monitoring equipment may also be installed e.g., downhole and / or on the surface). A wellbore may also include any completion hardware that is not discussed separately. The term "wellbore" may be used synonymously with the terms "borehole," "well," or "well bore." The term "wellbore" is not limited to any description or configuration described herein.

[0155] “Slickwater,” as used herein, refers to water-based aqueous solution comprising a friction reducer which is typically pumped at high rates to fracture a reservoir. Optionally when employing slickwater, smaller sized proppant particles (e.g., 40 / 70 or 50 / 140 mesh size) are used due to the fluid having a relatively low viscosity (and therefore a diminished ability to transport sizable proppants relative to more viscous fluids). In some embodiments, proppants are added to some stages of completion during production of an unconventional reservoir. In some embodiments, slickwater is injected with a small quantity of proppant.

[0156] “Fracturing” is one way that hydrocarbons may be recovered (sometimes referred to as produced) from the formation. For example, hydraulic fracturing may entail preparing a fracturing fluid and injecting that fracturing fluid into the wellbore at a sufficient rate and pressure to open existing fractures and / or create fractures in the formation. The fractures permit hydrocarbons to flow more freely into the wellbore. In the hydraulic fracturing process, the fracturing fluid may be prepared on-site to include at least proppants. The proppants, such as sand or other particles, are meant to hold the fractures open so that hydrocarbons can more easily flow to the wellbore. The fracturing fluid and the proppants may be blended together using at least one blender. The fracturing fluid may also include other components in addition to the proppants.

[0157] The wellbore and the formation proximate to the wellbore are in fluid communication (e.g., via perforations), and the fracturing fluid with the proppants is injected into the wellbore through a wellhead of the wellbore using at least one pump (oftentimes called a fracturing pump). The fracturing fluid with the proppants is injected at a sufficient rate and pressure to open existing fractures and / or create fractures in the subsurface volume of interest. As fractures become sufficiently wide to allow proppants to flow into those fractures, proppants in the fracturing fluid are deposited in those fractures during injection of the fracturing fluid. After the hydraulic fracturing process is completed, the fracturing fluid is removed by flowing or pumping it back out of the wellbore so that the fracturing fluid does not block the flow of hydrocarbons to the wellbore. The hydrocarbons will typically enter the same wellbore from the formation and go up to the surface for further processing.

[0158] The equipment to be used in preparing and injecting the fracturing fluid may be dependent on the components of the fracturing fluid, the proppants, the wellbore, the formation, etc. However, for simplicity, the term “fracturing apparatus” is meant to represent any tank(s), mixer(s), blender(s), pump(s), manifold(s), line(s), valve(s), fluid(s), fracturing fluid component(s), proppants, and other equipment and non-equipment items related to preparing the fracturing fluid and injecting the fracturing fluid.

[0159] Other hydrocarbon recovery processes may also be utilized to recover the hydrocarbons. Furthermore, those of ordinary skill in the art will appreciate that one hydrocarbon recovery process may also be used in combination with at least one other recovery process or subsequent to at least one other recovery process.

[0160] The term "interfacial tension" or "IFT" as used herein refers to the surface tension between test oil and water of different salinities containing a surfactant formulation at different concentrations. Typically, interfacial tensions are measured using a spinning drop tensiometer or calculated from phase behavior experiments.

[0161] The term "proximate" is defined as "near". If item A is proximate to item B, then item A is near item B. For example, in some embodiments, item A may be in contact with item B. For example, in some embodiments, there may be at least one barrier between item A and item B such that item A and item B are near each other, but not in contact with each other. The barrier may be a fluid barrier, a non-fluid barrier (e.g., a structural barrier), or any combination thereof. Both scenarios are contemplated within the meaning of the term "proximate. "

[0162] The term "contacting" as used herein, refers to materials or compounds being sufficiently close in proximity to react or interact. For example, in methods of contacting an unrefined petroleum material, a hydrocarbon-bearing formation, and / or a wellbore, the term "contacting" can include placing a compound (e.g., a surfactant) or an aqueous composition (e.g., chemical, surfactant or polymer) within a hydrocarbon-bearing formation using any suitable manner known in the art (e.g., pumping, injecting, pouring, releasing, displacing, spotting or circulating the chemical into a wellbore or hydrocarbon-bearing formation).

[0163] The terms "unrefined petroleum" and "crude oil" are used interchangeably and in keeping with the plain ordinary usage of those terms. "Unrefined petroleum" and "crude oil" may be found in a variety of petroleum reservoirs (also referred to herein as a "reservoir," "oil field deposit" "deposit" and the like) and in a variety of forms including oleaginous materials, oil shales (i.e., organic -rich fine-grained sedimentary rock), tar sands, light oil deposits, heavy oil deposits, and the like. "Crude oils" or "unrefined petroleums" generally refer to a mixture of naturally occurring hydrocarbons that may be refined into diesel, gasoline, heating oil, jet fuel, kerosene, and other products called fuels or petrochemicals. Crude oils or unrefined petroleums are named according to their contents and origins, and are classified according to their per unit weight (specific gravity). Heavier crudes generally yield more heat upon burning, but have lower gravity as defined by the American Petroleum Institute (API) (i.e., API gravity) and market price in comparison to light (or sweet) crude oils. Crude oil may also be characterized by its Equivalent Alkane Carbon Number (EACN). The term "API gravity" refers to the measure of how heavy or light a petroleum liquid is compared to water. If an oil's API gravity is greater than 10, it is lighter and floats on water, whereas if it is less than 10, it is heavier and sinks. API gravity is thus an inverse measure of the relative density of a petroleum liquid and the density of water. API gravity may also be used to compare the relative densities of petroleum liquids. For example, if one petroleum liquid floats on another and is therefore less dense, it has a greater API gravity.

[0164] Crude oils vary widely in appearance and viscosity from field to field. They range in color, odor, and in the properties they contain. While all crude oils are mostly hydrocarbons, the differences in properties, especially the variation in molecular structure, determine whether a crude oil is more or less easy to produce, pipeline, and refine. The variations may even influence its suitability for certain products and the quality of those products. Crude oils are roughly classified into three groups, according to the nature of the hydrocarbons they contain, (i) Paraffin-based crude oils contain higher molecular weight paraffins, which are solid at room temperature, but little or no asphaltic (bituminous) matter. They can produce high-grade lubricating oils, (ii) Asphaltene based crude oils contain large proportions of asphaltic matter, and little or no paraffin. Some are predominantly naphthenes and so yield lubricating oils that are sensitive to temperature changes than the paraffin-based crudes, (iii) Mixed based crude oils contain both paraffin and naphthenes, as well as aromatic hydrocarbons. Most crude oils fit this latter category.

[0165] "Reactive" crude oil, as referred to herein, is crude oil containing natural organic acidic components (also referred to herein as unrefined petroleum acid) or their precursors such as esters or lactones. These reactive crude oils can generate soaps (carboxylates) when reacted with alkali. More terms used interchangeably for crude oil throughout this disclosure are hydrocarbons, hydrocarbon material, or active petroleum material. An "oil bank" or "oil cut" as referred to herein, is the crude oil that does not contain the injected chemicals and is pushed by the injected fluid during an enhanced oil recovery process. A "nonactive oil," as used herein, refers to an oil that is not substantially reactive or crude oil not containing significant amounts of natural organic acidic components or their precursors such as esters or lactones such that significant amounts of soaps are generated when reacted with alkali. A nonactive oil as referred to herein includes oils having an acid number of less than 0.5 mg KOH / g of oil.

[0166] "Unrefined petroleum acids" as referred to herein are carboxylic acids contained in active petroleum material (reactive crude oil). The unrefined petroleum acids contain C11-C20 alkyl chains, including napthenic acid mixtures. The recovery of such "reactive" oils may be performed using alkali (e.g., NaOH, NaHCCh, or Na^COfi in a surfactant composition. The alkali reacts with the acid in the reactive oil to form soap in situ. These in situ generated soaps serve as a source of surfactants minimizing the levels of added surfactants, thus enabling efficient oil recovery from the reservoir.

[0167] The term "polymer" refers to a molecule having a structure that essentially includes the multiple repetitions of units derived, actually or conceptually, from molecules of low relative molecular mass. In some embodiments, the polymer is an oligomer. The term "productivity" as applied to a petroleum or oil well refers to the capacity of a well to produce hydrocarbons (e.g., unrefined petroleum); that is, the ratio of the hydrocarbon flow rate to the pressure drop, where the pressure drop is the difference between the average reservoir pressure and the flowing bottom hole well pressure (i.e., flow per unit of driving force).

[0168] The term "solubility" or "solubilization" in general refers to the property of a solute, which can be a solid, liquid or gas, to dissolve in a solid, liquid or gaseous solvent thereby forming a homogenous solution of the solute in the solvent. Solubility occurs under dynamic equilibrium, which means that solubility results from the simultaneous and opposing processes of dissolution and phase joining (e.g., precipitation of solids). The solubility equilibrium occurs when the two processes proceed at a constant rate. The solubility of a given solute in a given solvent typically depends on temperature. For many solids dissolved in liquid water, the solubility increases with temperature. In liquid water at high temperatures, the solubility of ionic solutes tends to decrease due to the change of properties and structure of liquid water. In more particular, solubility and solubilization as referred to herein is the property of oil to dissolve in water and vice versa.

[0169] "Viscosity" refers to a fluid's internal resistance to flow or being deformed by shear or tensile stress. In other words, viscosity may be defined as thickness or internal friction of a liquid. Thus, water is "thin", having a lower viscosity, while oil is "thick", having a higher viscosity. More generally, the less viscous a fluid is, the greater its ease of fluidity.

[0170] The term "salinity" as used herein, refers to concentration of salt dissolved in an aqueous phase. Examples for such salts are without limitation, sodium chloride, magnesium and calcium sulfates, and bicarbonates. In more particular, the term salinity as it pertains to the present invention refers to the concentration of salts in brine and surfactant solutions.

[0171] The term "co-solvent," as used herein, refers to a compound having the ability to increase the solubility of a solute (e.g., a surfactant as disclosed herein) in the presence of an unrefined petroleum acid. In some embodiments, the co-solvents provided herein have a hydrophobic portion (alkyl or aryl chain), a hydrophilic portion (e.g., an alcohol) and optionally an alkoxy portion. Co-solvents as provided herein include alcohols (e.g., C1-C6alcohols, C1-C6diols), alkoxy alcohols (e.g., C1-C6alkoxy alcohols, C1-C6alkoxy diols, and phenyl alkoxy alcohols), glycol ether, glycol and glycerol. The term "alcohol" is used according to its ordinary meaning and refers to an organic compound containing an -OH groups attached to a carbon atom. The term "diol" is used according to its ordinary meaning and refers to an organic compound containing two -OH groups attached to two different carbon atoms. The term "alkoxy alcohol" is used according to its ordinary meaning and refers to an organic compound containing an alkoxy linker attached to a -OH group.

[0172] The term “bitumen” refers to a mixture of organic liquids that are highly viscous, black, sticky, entirely soluble in carbon disulfide, and composed primarily of highly condensed polycyclic aromatic hydrocarbons. Naturally occurring or crude bitumen is a sticky, tar-like tacky organic form of petroleum which is typically very viscous. It is commonly known as tar or pitch. The high viscosity of the build-up makes these materials extremely difficult to remove from the piping. According to the SAGD (steam assisted gravity drainage) and CSS (cyclic steam stimulation) methods, volumes of steam are injected into the piping to lower the viscosity of the material. SAGD allows for the material to be produced in the lower horizontal piping of the well system, while CSS injects and produces bitumen material through a common vertical well.

[0173] Chemical Definitions

[0174] Terms used herein will have their customary meaning in the art unless specified otherwise. The organic moieties mentioned when defining variable positions within the general formulae described herein (e.g., the term “halogen”) are collective terms for the individual substituents encompassed by the organic moiety. Ph in Formula I refers to a phenyl group.

[0175] The prefix Cn-Cmpreceding a group or moiety indicates, in each case, the possible number of carbon atoms in the group or moiety that follows.

[0176] As used herein, the term “substituted” is contemplated to include all permissible substituents of organic compounds. In a broad aspect, the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. The permissible substituents can be one or more and the same or different for appropriate organic compounds. For purposes of this disclosure, heteroatoms present in a compound or moiety, such as nitrogen, can have hydrogen substituents and / or any permissible substituents of organic compounds described herein which satisfy the valency of the heteroatom. This disclosure is not intended to be limited in any manner by the permissible substituents of organic compounds. Also, the terms “substitution” or “substituted with” include the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound (e.g., a compound that does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, etc.).

[0177] The term "optionally substituted," as used herein, means that substitution with an additional group is optional and therefore it is possible for the designated atom to be unsubstituted. Thus, by use of the term “optionally substituted” the disclosure includes examples where the group is substituted and examples where it is not.

[0178] “Z1,” “Z2,” “Z3,” and “Z4” are used herein as generic symbols to represent various specific substituents. These symbols can be any substituent, not limited to those disclosed herein, and when they are defined to be certain substituents in one instance, they can, in another instance, be defined as some other substituents.

[0179] As used herein, the term “alkyl” refers to saturated, straight-chained or branched saturated hydrocarbon moieties. Unless otherwise specified, C1-C24 (e.g., C1-C22, C1-C20, Ci-Cis, C1-C16, C1-C14, C1-C12, C1-C10, Ci-Cs, C1-C6, or C1-C4) alkyl groups are intended. Examples of alkyl groups include methyl, ethyl, propyl, 1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl- propyl, 1,1-dimethyl-ethyl, pentyl, 1 -methyl-butyl, 2-methyl-butyl, 3-methyl-butyl, 2,2- dimethyl-propyl, 1-ethyl-propyl, hexyl, 1 , 1 -dimethyl -propyl, 1 ,2-dimethyl-propyl, 1 -methylpentyl, 2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1 , 1 -dimethyl -butyl, 1 ,2-dimethyl- butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl, 2,3-dimethyl-butyl, 3,3-dimethyl-butyl, 1-ethyl- butyl, 2-ethyl-butyl, 1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl, 1 -ethyl- 1-methyl-propyl, and l-ethyl-2-methyl-propyl. Alkyl substituents may be unsubstituted or substituted with one or more chemical moieties. The alkyl group can be substituted with one or more groups including, but not limited to, hydroxy, halogen, acyl, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiosulfonate (e.g., -SSChRa), or thiol, as described below, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. The alkyl group can also include one or more heteroatoms (e.g., from one to three heteroatoms) incorporated within the hydrocarbon moiety. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus.

[0180] Throughout the specification “alkyl” is generally used to refer to both unsubstituted alkyl groups and substituted alkyl groups; however, substituted alkyl groups are also specifically referred to herein by identifying the specific substituent(s) on the alkyl group. For example, the term “halogenated alkyl” specifically refers to an alkyl group that is substituted with one or more halides (halogens; e.g., fluorine, chlorine, bromine, or iodine). The term “alkoxyalkyl” specifically refers to an alkyl group that is substituted with one or more alkoxy groups, as described below. The term “alkylamino” specifically refers to an alkyl group that is substituted with one or more amino groups, as described below, and the like. The term “alkylthiol” specifically refers to an alkyl group that is substituted with one or more thiol groups, as described below, and the like. When “alkyl” is used in one instance and a specific term such as “alkylalcohol” is used in another, it is not meant to imply that the term “alkyl” does not also refer to specific terms such as “alkylalcohol” and the like.

[0181] This practice is also used for other groups described herein. That is, while a term such as “cycloalkyl” refers to both unsubstituted and substituted cycloalkyl moieties, the substituted moieties can, in addition, be specifically identified herein; for example, a particular substituted cycloalkyl can be referred to as, e.g., an “alkylcycloalkyl.” Similarly, a substituted alkoxy can be specifically referred to as, e.g. , a “halogenated alkoxy,” a particular substituted alkenyl can be, e.g., an “alkenylalcohol,” and the like. Again, the practice of using a general term, such as “cycloalkyl,” and a specific term, such as “alkylcycloalkyl,” is not meant to imply that the general term does not also include the specific term.

[0182] As used herein, the term “alkenyl” refers to unsaturated, straight-chained, or branched hydrocarbon moieties containing a double bond. Unless otherwise specified, C2-C24 (e.g., C2-C22, C2-C20, C2-C18, C2-C16, C2-C14, C2-C12, C2-C10, C2-C8, C2-C6, C2-C4) alkenyl groups are intended. Alkenyl groups may contain more than one unsaturated bond. Examples include ethenyl, 1- propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1 -propenyl, 2- methyl- 1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3- pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl- 1-butenyl, 3-methyl- 1-butenyl, l-methyl-2- butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3- methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1 ,2-dimethyl- 1 -propenyl, l,2-dimethyl-2-propenyl, 1 -ethyl- 1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,

[0183] 1 -methyl- 1 -pentenyl, 2-methyl- 1 -pentenyl, 3 -methyl- 1 -pentenyl, 4-methyl-l -pentenyl, 1-methyl-

[0184] 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3- pentenyl, 2-methyl-3 -pentenyl, 3-methyl-3 -pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, 1,1- dimethyl-3-butenyl, 1 ,2-dimethyl- 1 -butenyl, 1 ,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3- butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl- 1 -butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl- 1 -butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2- ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl- 3 -butenyl, l,l,2-trimethyl-2-propenyl, 1-ethyl-l- methyl-2-propenyl, l-ethyl-2-methyl-l -propenyl, and 1 -ethyl-2-methyl-2-propenyl. The term “vinyl” refers to a group having the structure -CH=CH2; 1 -propenyl refers to a group with the structure-CH=CH-CH3; and 2- propenyl refers to a group with the structure -CH2-CH=CH2. Asymmetric structures such as (Z]Z2)C=C(Z3Z4) are intended to include both the E and Z isomers. This can be presumed in structural formulae herein wherein an asymmetric alkene is present, or it can be explicitly indicated by the bond symbol C=C. Alkenyl substituents may be unsubstituted or substituted with one or more chemical moi eties. Examples of suitable substituents include, for example, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiosulfonate (e.g., -SSChRa), or thiol, as described below, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied.

[0185] As used herein, the term “alkynyl” represents straight-chained or branched hydrocarbon moieties containing a triple bond. Unless otherwise specified, C2-C24 (e.g., C2-C22, C2-C20, C2- Cis, C2-C16, C2-C14, C2-C12, C2-C10, C2-C8, C2-C6, C2-C4) alkynyl groups are intended. Alkynyl groups may contain more than one unsaturated bond. Examples include C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl- 1-butynyl, l-methyl-2- butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, l,l-dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3 -methyl- 1 -pentynyl, 4-methyl-l- pentynyl, l-methyl-2-pentynyl, 4-methyl-2-pentynyl, l-methyl-3-pentynyl, 2-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, l,l-dimethyl-2-butynyl, 1,1- dimethyl- 3-butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1- ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1 -ethyl- 1 -methyl-2-propynyl. Alkynyl substituents may be unsubstituted or substituted with one or more chemical moieties. Examples of suitable substituents include, for example, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiosulfonate (e.g., -SSChRa), and thiol, as described below. As used herein, the term “aryl,” as well as derivative terms such as aryloxy, refers to groups that include a monovalent aromatic carbocyclic group of from 3 to 20 carbon atoms. Aryl groups can include a single ring or multiple condensed rings. In some embodiments, aryl groups include Ce-Cio aryl groups. Examples of aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, tetrahydronaphthyl, phenylcyclopropyl, and indanyl. In some embodiments, the aryl group can be a phenyl, indanyl or naphthyl group. The term “heteroaryl” is defined as a group that contains an aromatic group that has at least one heteroatom incorporated within the ring of the aromatic group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus. The term “non-heteroaryl,” which is included in the term “aryl,” defines a group that contains an aromatic group that does not contain a heteroatom. The aryl or heteroaryl substituents may be unsubstituted or substituted with one or more chemical moieties. Examples of suitable substituents include, for example, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, cycloalkyl, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, or thiol as described herein. The term “biaryl” is a specific type of aryl group and is included in the definition of aryl. Biaryl refers to two aryl groups that are bound together via a fused ring structure, as in naphthalene, or are attached via one or more carbon-carbon bonds, as in biphenyl.

[0186] The term “cycloalkyl” as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “heterocycloalkyl” is a cycloalkyl group as defined above where at least one of the carbon atoms of the ring is substituted with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. The cycloalkyl group and heterocycloalkyl group can be substituted or unsubstituted. The cycloalkyl group and heterocycloalkyl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, or thiol as described herein.

[0187] The term “cycloalkenyl” as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms and containing at least one double bound, i.e., C=C. Examples of cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, and the like. The term “heterocycloalkenyl” is a type of cycloalkenyl group as defined above, and is included within the meaning of the term “cycloalkenyl,” where at least one of the carbon atoms of the ring is substituted with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. The cycloalkenyl group and heterocycloalkenyl group can be substituted or unsubstituted. The cycloalkenyl group and heterocycloalkenyl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, and thiol as described herein.

[0188] The term “cyclic group” is used herein to refer to either aryl groups, non-aryl groups (z.e., cycloalkyl, heterocycloalkyl, cycloalkenyl, and heterocycloalkenyl groups), or both. Cyclic groups have one or more ring systems that can be substituted or unsubstituted. A cyclic group can contain one or more aryl groups, one or more non-aryl groups, or one or more aryl groups and one or more non-aryl groups.

[0189] As used herein, “heteroaryl” refers to a monocyclic or polycyclic aromatic heterocycle having at least one heteroatom ring member selected from sulfur, oxygen, and nitrogen. In some embodiments, the heteroaryl ring has 1, 2, 3, or 4 heteroatom ring members independently selected from nitrogen, sulfur and oxygen. In some embodiments, any ring-forming N in a heteroaryl moiety can be an N-oxide. In some embodiments, the heteroaryl has 5-10 ring atoms and 1, 2, 3 or 4 heteroatom ring members independently selected from nitrogen, sulfur and oxygen. In some embodiments, the heteroaryl has 5-6 ring atoms and 1 or 2 heteroatom ring members independently selected from nitrogen, sulfur and oxygen. In some embodiments, the heteroaryl is a five-membered or six-membered heteroaryl ring. A five-membered heteroaryl ring is a heteroaryl with a ring having five ring atoms wherein one or more (e.g., 1, 2, or 3) ring atoms are independently selected from N, O, and S. Exemplary five-membered ring heteroaryls are thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyrazolyl, isothiazolyl, isoxazolyl, 1,2,3-triazolyl, tetrazolyl, 1,2,3-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-triazolyl, 1,2,4- thiadiazolyl, 1 ,2,4-oxadiazolyl, 1,3,4-triazoIyI, 1,3,4-thiadiazolyl, and 1,3,4-oxadiazolyl. A sixmembered heteroaryl ring is a heteroaryl with a ring having six ring atoms wherein one or more (e.g., 1, 2, or 3) ring atoms are independently selected from N, O, and S. Exemplary sixmembered ring heteroaryls are pyridyl, pyrazinyl, pyrimidinyl, triazinyl, and pyridazinyl.

[0190] As used herein, “heterocycloalkyl” refers to non-aromatic monocyclic or polycyclic heterocycles having one or more ring-forming heteroatoms selected from O, N, or S. Included in heterocycloalkyl are monocyclic 4-, 5-, 6-, and 7-membered heterocycloalkyl groups. Heterocycloalkyl groups can also include spirocycles. Example heterocycloalkyl groups include pyrrolidin-2-one, l,3-isoxazolidin-2-one, pyranyl, tetrahydropuran, oxetanyl, azetidinyl, morpholino, thiomorpholino, piperazinyl, tetrahydrofuranyl, tetrahydro thienyl, piperidinyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, azepanyl, benzazapene, and the like. Ring-forming carbon atoms and heteroatoms of a heterocycloalkyl group can be optionally substituted by oxo or sulfido (e.g., C(O), S(O), C(S), or S(O)2, etc.). The heterocycloalkyl group can be attached through a ringforming carbon atom or a ring-forming heteroatom. In some embodiments, the heterocycloalkyl group contains 0 to 3 double bonds. In some embodiments, the heterocycloalkyl group contains 0 to 2 double bonds. Also included in the definition of heterocycloalkyl are moieties that have one or more aromatic rings fused (i.e., having a bond in common with) to the cycloalkyl ring, for example, benzo or thienyl derivatives of piperidine, morpholine, azepine, etc. A heterocycloalkyl group containing a fused aromatic ring can be attached through any ring-forming atom including a ring-forming atom of the fused aromatic ring. In some embodiments, the heterocycloalkyl has 4-10, 4-7 or 4-6 ring atoms with 1 or 2 heteroatoms independently selected from nitrogen, oxygen, or sulfur and having one or more oxidized ring members.

[0191] At certain places, the definitions or embodiments refer to specific rings (e.g., an azetidine ring, a pyridine ring, etc.). Unless otherwise indicated, these rings can be attached to any ring member provided that the valency of the atom is not exceeded. For example, an azetidine ring may be attached at any position of the ring, whereas a pyridin-3-yl ring is attached at the 3- position.

[0192] The term “acyl” as used herein is represented by the formula -C(O)Z]where Z1can be a hydrogen, hydroxyl, alkoxy, alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above. As used herein, the term “acyl” can be used interchangeably with “carbonyl.” Throughout this specification “C(O)” or “CO” is a short hand notation for C=O.

[0193] As used herein, the term “alkoxy” refers to a group of the formula Z'-O-, where Z1is unsubstituted or substituted alkyl as defined above. Unless otherwise specified, alkoxy groups wherein Z1is a C1-C24 (e.g., C1-C22, C1-C20, Ci-Cis, C1-C16, C1-C14, C1-C12, C1-C10, Ci-Cs, Ci- Ce, C1-C4) alkyl group are intended. Examples include methoxy, ethoxy, propoxy, 1-methyl- ethoxy, butoxy, 1-methyl-propoxy, 2-methyl-propoxy, 1,1 -dimethyl-ethoxy, pentoxy, 1-methyl- butyloxy, 2-methyl-butoxy, 3-methyl-butoxy, 2,2-di-methyl-propoxy, 1-ethyl-propoxy, hexoxy, 1.1 -dimethyl -propoxy, 1 ,2-dimethyl-propoxy, 1 -methyl-pentoxy, 2-methyl-pentoxy, 3-methyl- pentoxy, 4-methyl-penoxy, 1,1-dimethyl-butoxy, 1 ,2-dimethyl-butoxy, 1,3-dimethyl-butoxy,

[0194] 2.2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy, 1-ethyl-butoxy, 2-ethylbutoxy,

[0195] 1.1.2-trimethyl-propoxy, 1,2,2-trimethyl-propoxy, 1 -ethyl- 1-methyl-propoxy, and l-ethyl-2- methyl-propoxy.

[0196] The term “aldehyde” as used herein is represented by the formula — C(O)H.

[0197] The terms “amine” or “amino” as used herein are represented by the formula — NZ'Z2, where Z1and Z2can each be substitution group as described herein, such as hydrogen, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above. “Amido” is — C(O)NZ*Z2.

[0198] The term “carboxylic acid” as used herein is represented by the formula — C(O)OH. A “carboxylate” or “carboxyl” group as used herein is represented by the formula — C(O)O’.

[0199] The term “ester” as used herein is represented by the formula — OC(O)Z]or

[0200] — OIOZ1, where Z1can be an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.

[0201] The term “ether” as used herein is represented by the formula Z'OZ2, where Z1and Z2can be, independently, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.

[0202] The term “ketone” as used herein is represented by the formula Z]C(O)Z2, where Z1and Z2can be, independently, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.

[0203] The term “halide” or “halogen” or “halo” as used herein refers to fluorine, chlorine, bromine, and iodine.

[0204] The term “hydroxyl” as used herein is represented by the formula — OH.

[0205] The term “nitro” as used herein is represented by the formula — NO2.

[0206] The term “silyl” as used herein is represented by the formula — SiZ*Z2Z3, where Z1, Z2, and Z3can be, independently, hydrogen, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.

[0207] The term “sulfonyl” is used herein to refer to the sulfo-oxo group represented by the formula — S(O)2Z], where Z1can be hydrogen, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.

[0208] The term “sulfonylamino” or “sulfonamide” as used herein is represented by the formula — S(O)2NH— .

[0209] The term “thiol” as used herein is represented by the formula — SH.

[0210] The term “thio” as used herein is represented by the formula — S — .

[0211] As used herein, Me refers to a methyl group; OMe refers to a methoxy group; and z-Pr refers to an isopropyl group.

[0212] “R1,” “R2,” “R3,” “Rn,” etc., where n is some integer, as used herein can, independently, possess one or more of the groups listed above. For example, if R1is a straight chain alkyl group, one of the hydrogen atoms of the alkyl group can optionally be substituted with a hydroxyl group, an alkoxy group, an amine group, an alkyl group, a halide, and the like. Depending upon the groups that are selected, a first group can be incorporated within second group or, alternatively, the first group can be pendant (i.e., attached) to the second group. For example, with the phrase “an alkyl group comprising an amino group,” the amino group can be incorporated within the backbone of the alkyl group. Alternatively, the amino group can be attached to the backbone of the alkyl group. The nature of the group(s) that is (are) selected will determine if the first group is embedded or attached to the second group.

[0213] The term "substituted" refers to a molecule wherein at least one hydrogen atom is replaced with a substituent. When substituted, one or more of the groups are "substituents." The molecule can be multiply substituted. In the case of an oxo substituent ("=O"), two hydrogen atoms are replaced. Example substituents within this context can include halogen, hydroxy, alkyl, alkoxy, nitro, cyano, oxo, carbocyclyl, carbocycloalkyl, heterocarbocyclyl, heterocarbocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, -NRaRb, -NRaC(=O)Rb, - NRaC(=O)NRaNRb, -NRaC(=O)ORb, - NRaSO2Rb, -C(=O)Ra, -C(=O)ORa, -C(=O)NRaRb, - OC(=O)NRaRb, -ORa, -SRa, -SORa, - S(=O)2Ra, -OS(=O)2Ra and -S(=O)2ORa. Ra and Rb in this context can be the same or different and independently hydrogen, halogen hydroxyl, alkyl, alkoxy, alkyl, amino, alkylamino, dialkylamino, carbocyclyl, carbocycloalkyl, heterocarbocyclyl, heterocarbocycloalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl.

[0214] Unless stated to the contrary, a formula with chemical bonds shown only as solid lines and not as wedges or dashed lines contemplates each possible stereoisomer or mixture of stereoisomer (e.g., each enantiomer, each diastereomer, each meso compound, a racemic mixture, or scalemic mixture).

[0215] Many of the compounds described herein include one or more alkylene oxide units, such as propoxy units, ethoxy units, butoxy units, or a combination thereof. When indicated in a structural formula (e.g., as -(PO)x-(EO)y-A or -(BO)z-(PO)x-(EO)y-A) that contain more than one type of alkylene oxide unit, these formulae can indicate a block copolymer or a random copolymer comprising the alkylene oxide units in the molar ratios specified by the subscripts (e.g., x, y, and z). In certain embodiments, when indicated in a structural formula (e.g., as - (PO)x-(EO)y-A or -(BO)z-(PO)x-(EO)y-A) that contain more than one type of alkylene oxide unit, these formulae can indicate a block copolymer comprising the alkylene oxide units in the molar ratios specified by the subscripts (e.g., x, y, and z).

[0216] Reference will now be made in detail to specific aspects of the disclosed materials, compounds, compositions, articles, and methods, examples of which are illustrated in the accompanying Examples and Figures.

[0217] Compounds

[0218] Described herein are tristyryl phenol polysulfonate compounds and tristyryl phenol alkoxylate polysulfonate compounds of Formula I: alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0219] R16is alkene, C1-C32alkyl,

[0220] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0221] BO represents -CH2-CH(ethyl)-O-;

[0222] EO represents -CH2-CH2-O-;

[0223] PO represents -CH2-CH(methyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; n, m, p, and q are each independently 0 to 6; and the dotted line represents an optional double bond if valence permits; at least two of R'-R9, R12-R17or A are independently -SO3; one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3. then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl.

[0224] In some embodiments, the compounds of Formula I can include at least 2 sulfonates (e.g., at least 3, at least 4, at least 5, at least 6, or at least 7) In some embodiments, the compounds of Formula I can include from 2 to 7 sulfonates, (e.g., from 2 to 6 sulfonates, from 2 to 5 sulfonates, from 2 to 4 sulfonates, or from 2 to 3 sulfonates).

[0225] Described herein are tristyryl phenol polysulfonate compounds and tristyryl phenol alkoxylate polysulfonate compounds of Formula I:

[0226] R2-R5are each independently H or -SO3;

[0227] R6-R9and R12-R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0228] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0229] BO represents -CH2-CH(ethyl)-O-;

[0230] EO represents -CH2-CH2-O-;

[0231] PO represents -CH2-CH(methyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; n, m, p, and q are each independently 0 to 6; and the dotted line represents an optional double bond if valence permits; at least two of R1-R9, R12-R15or A are independently -SO3; wherein when: , one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl.

[0232] In some embodiments, R1is -OH. In some embodiments, R1is -OSO3. In some embodiments, R1is -(PO)x-(EO)y-A. In some embodiments, R1is -(BO)z(PO)x-(EO)y-A. In some embodiment, R1is -OR16. In some embodiments, some embodiments, some embodiments 5 , R1is

[0233] In some embodiments, R2is H. In some embodiments, R3is H. In some embodiments, R4is H. In some embodiments, R5is H. In some embodiments, R2is -SO3. In some embodiments, R3is -SO3. In some embodiments, R4is -SO3. In some embodiments, R5is -SO3. In some embodiments, R2, R3, and R5are -SO3. In some embodiments, R2, R3, and R5are H. In some embodiments, R2and R5are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and R5is H. In some embodiments, R3and R5are -SO3, and R2is H. In some embodiments, R2and R5are H, and R3is -SO3. In some embodiments, R2and R3are H, and R5is -SO3. In some embodiments, R3and R5are H, and R2is -SO3. In some embodiments, R2, R3, and R4are -SO3.

[0234] In some embodiments, R2, R3, and R4are H. In some embodiments, R2and R4are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and R4is H. In some embodiments, R3and R4are -SO3, and R2is H. In some embodiments, R2and R4are H, and R3is -SO3. In some embodiments, R2and R3are H, and R4is -SO3. In some embodiments, R3and R4are H, and R2is -SO3.

[0235] In some embodiments, when R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-

[0236] A then some embodiments, when R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A, -OR16then some embodiments, when R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A then is H. In some embodiments, when R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A,

[0237] -OR16then some embodiments, when R1is In some embodiments, R11is H. In some embodiments, embodiments,

[0238] In some embodiments, when R11is H, then h

[0239] OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16. In some embodiments, when R11is , , , ,y A, -(BO)z-(PO)x-(EO)y-A, -OR16, and R10is H. In some embodiments, when R11 y y

[0240] In some embodiments, n, m, p, and q are 0. In some embodiments, n, m, p, and q are 1. In some embodiments, n, m, p, and q are 2. In some embodiments, n, m, p, and q are 3. In some embodiments, n, m, p, and q are 4. In some embodiments, n, m, p, and q are 5. In some embodiments, n, m, p, and q are 6. In some embodiments, n, m, and q are 0. In some embodiments, n, m, and q are 1 . In some embodiments, n, m, and q are 2. In some embodiments, n, m, and q are 3. In some embodiments, n, m, and q are 4. In some embodiments, n, m, and q are 5. In some embodiments, n, m, and q are 6. In some embodiments, n, m, and p are 1. In some embodiments, n, m, and p are 2. In some embodiments, n, m, and p are 3. In some embodiments, n, m, and p are 4. In some embodiments, n, m, and p are 5. In some embodiments, n, m, and p are 6.

[0241] In some embodiments, R6, R7, R8, and R9are H. In some embodiments, R6, R7, R8, and R9are -SO3. In some embodiments, R6, R7, R8, and R9are -OH. In some embodiments, R6, R7, R8, and R9are C1-C6alkyl. In some embodiments, R6, R7, R8, and R9are each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl.

[0242] In some embodiments, R6, R7, and R9are H. In some embodiments, R6, R7, and R9are - SO3. In some embodiments, R6, R7, and R9are -OH. In some embodiments, R6, R7, and R9are C1-C6alkyl. In some embodiments, R6, R7, and R9are each independently methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl. In some embodiments, R6, R7, and R9are methyl.

[0243] In some embodiments, R6, R7, and R8are H. In some embodiments, R6, R7, and R8are - SO3. In some embodiments, R6, R7, and R8are -OH. In some embodiments, R6, R7, and R8are C1-C6alkyl. In some embodiments, R6, R7, and R8are each independently methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl.

[0244] In some embodiments, R12, R13, R14, and R15are H. In some embodiments, R12, R13, R14, and R15are -SO3. In some embodiments, R12, R13, R14, and R15are -OH. In some embodiments, R12, R13, and R15are H. In some embodiments, R12, R13, and R15are -SO3. In some embodiments, R12, R13, and R15are -OH. In some embodiments, R12, R13, and R14are H. In some embodiments, R12, R13, and R14are -SO3. In some embodiments, R12, R13, and R14are -OH.

[0245] In some embodiments, when R6is -OH, then R12is not -OH. In some embodiments, when R12is -OH, then R6is not -OH. In some embodiments, when R6is -OH, then R12is H or - SO3. In some embodiments, when R12is -OH, then R6is H, -SO3or C1-C6alkyl. In some embodiments, when R8is -OH, then R14is not -OH. In some embodiments, when R14is -OH, then R8is not -OH. In some embodiments, when R8is -OH, then R14is H or -SO3. In some embodiments, when R14is -OH, then R8is H, -SO3or C1-C6alkyl. In some embodiments, when R7is -OH, then R13is not -OH. In some embodiments, when R13is -OH, then R7is not -OH. In some embodiments, when R7is -OH, then R13is H or -SO3. In some embodiments, when R13is - -OH, then R7is H, -SO3or C1-C6alkyl. In some embodiments, when R9is -OH, then R15is not - OH. In some embodiments, when R1Sis -OH, then R9is not -OH. In some embodiments, when R9is -OH, then R1Sis H or -SO3. In some embodiments, when R15is -OH, then R9is H, -SO3or Ci-C6alkyl.

[0246] In some embodiments, A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OR16. In some embodiments, A is - OH. In some embodiments, A is -OSO3. In some embodiments, A is -SO3. In some embodiments, A is an alkene. In some embodiments, A is a terminal alkene. In some embodiments, A is monocarboxylate. In some embodiments, A is dicarboxylate. In some embodiments, A is tricarboxylate.

[0247] R17R17

[0248] In some embodiments, R16is alkene, C1-C32alkyl, , , , or

[0249] OH . In some embodiments, R16is alkene. In some embodiments, R16is C1-C32alkyl. In R17v-^R17some embodiments, R16is * . In some embodiments, R16is . In some

[0250] R17V-^^R17

[0251] T embodiments, R16is . In some embodiments, R16is OH

[0252] In some embodiments, R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or - (BO)z(PO)x-(EO)y-A. In some embodiments, R17is H. In some embodiments, R17is C1-C32alkyl. In some embodiments, R17is alkenyl. In some embodiments, R17is aryl. In some embodiments, R17is C6-C 18 alkyl. In some embodiments, R17is C1-C24 alkyl. In some embodiments, R17is - (PO)x-(EO)y-A. In some embodiments, R17is -(BO)z(PO)x-(EO)y-A.

[0253] In some embodiments, x is 0 to 65, 0 to 60, 0 to 55, 0 to 50, 0 to 45, 0 to 40, 0 to 35, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 65, 1 to 60, 1 to 55, 1 to 50, 1 to 45, 1 to 40, 1 to 35, 1 to 30, 1 to 25, 1 to 20, 5 to 65, 5 to 60, 5 to 55, 5 to 50, 5 to 45, 5 to 40, 5 to 35, 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, 10 to 65, 10 to 60, 10 to 55, 10 to 50, 10 to 45, 10 to 40, 10 to 35, 10 to 30, 10 to 25, 10 to 20, 20 to 65, 20 to 60, 20 to 55, 20 to 50, 20 to

[0254] 45, 20 to 40, 20 to 35, 20 to 30, 20 to 25, 30 to 65, 30 to 60, 30 to 55, 30 to 50, 30 to 45, 30 to

[0255] 40, 30 to 35, 40 to 65, 40 to 60, 40 to 55, 40 to 50, 40 to 45, 50 to 65, 50 to 60, 50 to 55, or 60 to

[0256] 65. In some embodiments, x is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,

[0257] 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, or 65. In some embodiments, x is 0.

[0258] In some embodiments, y is 0 to 100, 0 to 90, 0 to 80, 0 to 70, 0 to 60, 0 to 50, 0 to 40, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 20, 1 to 25, 1 to 30, 1 to 100, 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, 1 to 40, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 20, 5 to 10, 10 to 100, 10 to 90, 10 to 80, 10 to 70, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 20, 20 to 100, 20 to 90, 20 to 80, 20 to 70, 20 to 60, 20 to 50, 20 to 40, 20 to 30, 30 to 100, 30 to 90, 30 to 80, 30 to 70, 30 to 60, 30 to 50, 30 to 40, 40 to 100, 40 to 90, 40 to 80, 40 to 70, 40 to 60, 40 to 50, 50 to 100, 50 to 90, 50 to 80, 50 to 70, 50 to 60, 60 to 100, 60 to 90, 60 to 80, 60 to 70, 70 to 100, 70 to 90, 70 to 80, 80 to 100, 80 to 90, or 90 to 100. In some embodiments, y is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100 In some embodiments, z is 0 to 10, 0 to 5, 1 to 5, 1 to 10, or 5 to 10. In some embodiments, z is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.

[0259] In some embodiments, x is 0.

[0260] In some embodiments, y is 0. In some embodiments, y is 16. In some embodiments, z is 0. In some embodiments, x is 0 and y is 16. In some embodiments, x is 0, y is 16, and z is 0.

[0261] Also described herein are compounds of Formula II: wherein:

[0262] R1is -OH,-OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;

[0263] R2-R4are each independently H or -SO3;

[0264] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0265] R16is alkene, Ci -C32 alkyl,

[0266] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0267] EO represents -CH2-CH2-O-;

[0268] PO represents -CH2-CH(methyl)-O-;

[0269] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R’-R4, R16, R17, or A are independently -SO3.

[0270] Also described herein are compounds of Formula II:

[0271] wherein:

[0272] R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A;

[0273] R2-R4are each independently H or -SO3;

[0274] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0275] EO represents -CH2-CH2-O-;

[0276] PO represents -CH2-CH(methyl)-O-;

[0277] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R1-R4, or A are independently -SO3.

[0278] In some embodiments, the compounds of Formula II can include at least 2 sulfonates (e.g., at least 3, at least 4, at least 5, at least 6, or at least 7) In some embodiments, the compounds of Formula II can include from 2 to 7 sulfonates, (e.g., from 2 to 6 sulfonates, from 2 to 5 sulfonates, from 2 to 4 sulfonates, or from 2 to 3 sulfonates).

[0279] In some embodiments, R1in Formula II is -OH. In some embodiments, R1in Formula II is -OSO3. In some embodiments, R1in Formula II is -(PO)x-(EO)y-A. In some embodiments, R1in Formula II is -(BO)z(PO)x-(EO)y-A. In some embodiments, R1in Formula II is -OR16.

[0280] In some embodiments, R2is H. In some embodiments, R3is H. In some embodiments, R4is H. In some embodiments, R2is -SO3. In some embodiments, R3is -SO3. In some embodiments, R4is -SO3. In some embodiments, R2, R3, and R4are -SO3. In some embodiments, R2, R3, and R4are H. In some embodiments, R2and R4are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and R4is H. In some embodiments, R3and R4are -SO3, and R2is H. In some embodiments, R2and R4are H, and R3is -SO3. In some embodiments, R2and R3are H, and R4is -SO3. In some embodiments, R3and R4are H, and R2is -SO3. In some embodiments, A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OR16. In some embodiments, A is -OH. In some embodiments, A is -OSO3. In some embodiments, A is -SO3. In some embodiments, A is alkene. In some embodiments, A is a terminal alkene. In some embodiments, A is monocarboxylate. In some embodiments, A is dicarboxylate. In some embodiments, A is tricarboxylate.

[0281] In some embodiments, R16is alkene, C1-C32alkyl, or

[0282] OH > insome embodiments, R16is alkene. In some embodiments, R16is C1-C32alkyl. In some embodiments, R16is . In some embodiments, R16is . In some

[0283] R17-^ P17

[0284] I embodiments, R16is . In some embodiments, R16is OH

[0285] In some embodiments, R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or - (BO)z(PO)x-(EO)y-A. In some embodiments, R17is H. In some embodiments, R17is C1-C32alkyl. In some embodiments, R17is alkenyl. In some embodiments, R17is aryl. In some embodiments, R17is C6-C 18 alkyl. In some embodiments, R17is C1-C24 alkyl. In some embodiments, R17is - (PO)x-(EO)y-A. In some embodiments, R17is -(BO)z(PO)x-(EO)y-A.

[0286] In some embodiments, x is 0 to 65, 0 to 60, 0 to 55, 0 to 50, 0 to 45, 0 to 40, 0 to 35, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 65, 1 to 60, 1 to 55, 1 to 50, 1 to 45, 1 to 40, 1 to 35, 1 to 30, 1 to 25, 1 to 20, 5 to 65, 5 to 60, 5 to 55, 5 to 50, 5 to 45, 5 to 40, 5 to 35, 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, 10 to 65, 10 to 60, 10 to 55, 10 to 50, 10 to 45, 10 to 40, 10 to 35, 10 to 30, 10 to 25, 10 to 20, 20 to 65, 20 to 60, 20 to 55, 20 to 50, 20 to 45, 20 to 40, 20 to 35, 20 to 30, 20 to 25, 30 to 65, 30 to 60, 30 to 55, 30 to 50, 30 to 45, 30 to 40, 30 to 35, 40 to 65, 40 to 60, 40 to 55, 40 to 50, 40 to 45, 50 to 65, 50 to 60, 50 to 55, or 60 to 65. In some embodiments, x is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, or 65. In some embodiments, x is 0. In some embodiments, y is 0 to 100, 0 to 90, 0 to 80, 0 to 70, 0 to 60, 0 to 50, 0 to 40, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 20, 1 to 25, 1 to 30, 1 to 100, 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, 1 to 40, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 20, 5 to 10, 10 to 100, 10 to 90, 10 to 80, 10 to 70, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 20, 20 to 100, 20 to 90, 20 to 80, 20 to 70, 20 to 60, 20 to 50, 20 to 40, 20 to 30, 30 to 100, 30 to 90, 30 to 80, 30 to 70, 30 to 60, 30 to 50, 30 to 40, 40 to 100, 40 to 90, 40 to 80, 40 to 70, 40 to 60, 40 to 50, 50 to 100, 50 to 90, 50 to 80, 50 to 70, 50 to 60, 60 to 100, 60 to 90, 60 to 80, 60 to 70, 70 to 100, 70 to 90, 70 to 80, 80 to 100, 80 to 90, or 90 to 100. In some embodiments, y is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100

[0287] In some embodiments, z is 0 to 10, 0 to 5, 1 to 5, 1 to 10, or 5 to 10. In some embodiments, z is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. In some embodiments, x is 0.

[0288] In some embodiments, y is 0. In some embodiments, y is 16. In some embodiments, z is 0. In some embodiments, x is 0 and y is 16. In some embodiments, x is 0, y is 16, and z is 0.

[0289] Also described herein are compounds of Formula III: wherein:

[0290] R2, R3, and R5are each independently H or -SO3;

[0291] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0292] R16is alkene, C1-C32alkyl,

[0293] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0294] EO represents -CH2-CH2-O-;

[0295] PO represents -CH2-CH(methyl)-O-;

[0296] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2, R3, Rs, R16, R17, or A are independently -SO3.

[0297] Also described herein are compounds of Formula III: wherein:

[0298] R2, R3, and R5are each independently H or -SO3;

[0299] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0300] EO represents -CH2-CH2-O-;

[0301] PO represents -CH2-CH(methyl)-O-;

[0302] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2, R3, R5, or A are independently -SO3.

[0303] In some embodiments, R2is H. In some embodiments, R3is H. In some embodiments, R5is H. In some embodiments, R2is -SO3. In some embodiments, R3is -SO3. In some embodiments, R5is -SO3. In some embodiments, R2, R3, and R5are -SO3. In some embodiments, R2, R3, and R5are H. In some embodiments, R2and R5are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and R5is H. In some embodiments, R3and R5are -SO3, and R2is H. In some embodiments, R2and R5are H, and R3is -SO3. In some embodiments, R2and R3are H, and R5is -SO3. In some embodiments, R3and R5are H, and R2is -SO3.

[0304] In some embodiments, A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OR16. In some embodiments, A is -OH. In some embodiments, A is -OSO3In some embodiments, A is -SO3In some embodiments, A is alkene. In some embodiments, A is a terminal alkene. In some embodiments, A is monocarboxylate. In some embodiments, A is dicarboxylate. In some embodiments, A is tricarboxylate.

[0305] In some embodiments, R16is alkene, CI-C 32 alkyl or . insome embodiments, R16is alkene. In some embodiments, R16is C1-C32alkyl. In some embodiments, . In some embodiments, In some embodiments,

[0306] In some embodiments, R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or - (BO)z(PO)x-(EO)y-A. In some embodiments, R17is H. In some embodiments, R17is C1-C32alkyl. In some embodiments, R17is alkenyl. In some embodiments, R17is aryl. In some embodiments, R17is C6-C18alkyl. In some embodiments, R17is C1-C24 alkyl. In some embodiments, R17is - (PO)x-(EO)y-A. In some embodiments, R17is -(BO)z(PO)x-(EO)y-A.

[0307] In some embodiments, x is 0 to 65, 0 to 60, 0 to 55, 0 to 50, 0 to 45, 0 to 40, 0 to 35, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 65, 1 to 60, 1 to 55, 1 to 50, 1 to 45, 1 to 40, 1 to 35, 1 to 30, 1 to 25, 1 to 20, 5 to 65, 5 to 60, 5 to 55, 5 to 50, 5 to 45, 5 to 40, 5 to 35, 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, 10 to 65, 10 to 60, 10 to 55, 10 to 50, 10 to 45, 10 to 40, 10 to 35, 10 to 30, 10 to 25, 10 to 20, 20 to 65, 20 to 60, 20 to 55, 20 to 50, 20 to 45, 20 to 40, 20 to 35, 20 to 30, 20 to 25, 30 to 65, 30 to 60, 30 to 55, 30 to 50, 30 to 45, 30 to 40, 30 to 35, 40 to 65, 40 to 60, 40 to 55, 40 to 50, 40 to 45, 50 to 65, 50 to 60, 50 to 55, or 60 to 65. In some embodiments, x is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, or 65. In some embodiments, x is 0.

[0308] In some embodiments, y is 0 to 100, 0 to 90, 0 to 80, 0 to 70, 0 to 60, 0 to 50, 0 to 40, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 20, 1 to 25, 1 to 30, 1 to 100, 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, 1 to 40, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 20, 5 to 10, 10 to 100, 10 to 90, 10 to 80, 10 to 70, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 20, 20 to 100, 20 to 90, 20 to 80, 20 to 70, 20 to 60, 20 to 50, 20 to 40, 20 to 30, 30 to 100, 30 to 90, 30 to 80, 30 to 70, 30 to 60, 30 to 50, 30 to 40, 40 to 100, 40 to 90, 40 to 80, 40 to 70, 40 to 60, 40 to 50, 50 to 100, 50 to 90, 50 to 80, 50 to 70, 50 to 60, 60 to 100, 60 to 90, 60 to 80, 60 to 70, 70 to 100, 70 to 90, 70 to 80, 80 to 100, 80 to 90, or 90 to 100. In some embodiments, y is 0, 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100.

[0309] In some embodiments, z is 0 to 10, 0 to 5, 1 to 5, 1 to 10, or 5 to 10. In some embodiments, z is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. In some embodiments, x is 0.

[0310] In some embodiments, y is 0. In some embodiments, y is 16. In some embodiments, z is 0. In some embodiments, x is 0 and y is 16. In some embodiments, x is 0, y is 16, and z is 0.

[0311] Also described herein are compounds of Formula IV : wherein:

[0312] R2, R3, and R5are each independently H or -SO3;

[0313] R6-R8, and R12-R14are each independently H, -OH, -SO3, or C1-C6alkyl;

[0314] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0315] R16is alkene, C1-C32alkyl,

[0316] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0317] EO represents -CH2-CH2-O-;

[0318] PO represents -CH2-CH(methyl)-O-;

[0319] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2, R3, R5-R8, R12-R17or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0320] Also described herein are compounds of Formula IV :

[0321] Formula IV or Formula IVA wherein:

[0322] R2, R3, and R5are each independently H or -SO3;

[0323] R6-R8, and R12-R14are each independently H, -OH, -SO3, or C1-C6alkyl;

[0324] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0325] EO represents -CH2-CH2-O-;

[0326] PO represents -CH2-CH(methyl)-O-;

[0327] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2, R3, R5-R8, R12-R14or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0328] In some embodiments, R2is H. In some embodiments, R3is H. In some embodiments, R5is H. In some embodiments, R2is -SO3. In some embodiments, R3is -SO3. In some embodiments, R5is -SO3. In some embodiments, R2, R3, and R5are -SO3. In some embodiments, R2, R3, and R5are H. In some embodiments, R2and R5are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and R5is H. In some embodiments, R3and R5are -SO3, and R2is H. In some embodiments, R2and R5are H, and R3is -SO3. In some embodiments, R2and R3are H, and Rsis -SO3. In some embodiments, R3and Rsare H, and R2is -SO3.

[0329] In some embodiments, R6, R7, and R8are H. In some embodiments, R6, R7, and R8are - SO3. In some embodiments, R6, R7, and R8are -OH. In some embodiments, R6, R7, and R8are C1-C6alkyl. In some embodiments, R6, R7, and R8are each independently methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl.

[0330] In some embodiments, R12, R13, and R14are H. In some embodiments, R12, R13, and R14are -SO3. In some embodiments, R12, R13, and R14are -OH.

[0331] In some embodiments, when R6is OH, then R12is not OH. In some embodiments, when R12is OH, then R6is not OH. In some embodiments, when R6is OH, then R12is H or -SO3. In some embodiments, when R12is OH, then R6is H, -SO3or C1-C6alkyl. In some embodiments, when R8is OH, then R14is not OH. In some embodiments, when R14is OH, then R8is not OH. In some embodiments, when R8is OH, then R14is H or -SO3. In some embodiments, when R14is OH, then R8is H, -SO3or C1-C6alkyl. In some embodiments, when R7is OH, then R13is not OH. In some embodiments, when R13is OH, then R7is not OH. In some embodiments, when R7is OH, then R13is H or -SO3. In some embodiments, when R13is OH, then R7is H, -SO3or Ci- Ce alkyl.

[0332] In some embodiments, A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OR16. In some embodiments, A is -OH. In some embodiments, A is -OSO3. In some embodiments, A is -SO3. In some embodiments, A is alkene. In some embodiments, A is monocarboxylate. In some embodiments, A is dicarboxylate. In some embodiments, A is tricarboxylate. In some embodiments, R16is alkene, C1-C32alkyl, or

[0333] OH . in some embodiments, R16is alkene. In some embodiments, R16is C1-C32alkyl. In

[0334] R17some embodiments, R16is . In some embodiments, R16is . In some embodiments, R16is . In some embodiments, R16is °H

[0335] In some embodiments, R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or - (BO)z(PO)x-(EO)y-A. In some embodiments, R17is H. In some embodiments, R17is alkenyl. In some embodiments, R17is C1-C32alkyl. In some embodiments, R17is aryl. In some embodiments, R17is Ce-Cis alkyl. In some embodiments, R17is C1-C24 alkyl. In some embodiments, R17is -(PO)x-(EO)y-A. In some embodiments, R17is -(BO)z(PO)x-(EO)y-A.

[0336] In some embodiments, x is 0 to 65, 0 to 60, 0 to 55, 0 to 50, 0 to 45, 0 to 40, 0 to 35, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 65, 1 to 60, 1 to 55, 1 to 50, 1 to 45, 1 to 40, 1 to 35, 1 to 30, 1 to 25, 1 to 20, 5 to 65, 5 to 60, 5 to 55, 5 to 50, 5 to 45, 5 to 40, 5 to 35, 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, 10 to 65, 10 to 60, 10 to 55, 10 to 50, 10 to 45, 10 to 40, 10 to 35, 10 to 30, 10 to 25, 10 to 20, 20 to 65, 20 to 60, 20 to 55, 20 to 50, 20 to 45, 20 to 40, 20 to 35, 20 to 30, 20 to 25, 30 to 65, 30 to 60, 30 to 55, 30 to 50, 30 to 45, 30 to 40, 30 to 35, 40 to 65, 40 to 60, 40 to 55, 40 to 50, 40 to 45, 50 to 65, 50 to 60, 50 to 55, or 60 to 65. In some embodiments, x is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, or 65. In some embodiments, x is 0.

[0337] In some embodiments, y is 0 to 100, 0 to 90, 0 to 80, 0 to 70, 0 to 60, 0 to 50, 0 to 40, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 20, 1 to 25, 1 to 30, 1 to 100, 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, 1 to 40, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 20, 5 to 10, 10 to 100, 10 to 90, 10 to 80, 10 to 70, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 20, 20 to 100, 20 to 90, 20 to 80, 20 to 70, 20 to 60, 20 to 50, 20 to 40, 20 to 30, 30 to 100, 30 to 90, 30 to 80, 30 to 70, 30 to 60, 30 to 50, 30 to 40, 40 to 100, 40 to 90, 40 to 80, 40 to 70, 40 to 60, 40 to 50, 50 to 100, 50 to 90, 50 to 80, 50 to 70, 50 to 60, 60 to 100, 60 to 90, 60 to 80, 60 to 70, 70 to 100, 70 to 90, 70 to 80, 80 to 100, 80 to 90, or 90 to 100. In some embodiments, y is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100.

[0338] In some embodiments, z is 0 to 10, 0 to 5, 1 to 5, 1 to 10, or 5 to 10. In some embodiments, z is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. In some embodiments, x is 0.

[0339] In some embodiments, y is 0. In some embodiments, y is 16. In some embodiments, z is 0. In some embodiments, x is 0 and y is 16. In some embodiments, x is 0, y is 16, and z is 0. Also described herein are compounds of Formula V or salt thereof: wherein:

[0340] R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;

[0341] R2-R4are each independently H or -SO3;

[0342] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0343] R16is alkene, Ci -C32 alkyl,

[0344] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0345] EO represents -CH2-CH2-O-;

[0346] PO represents -CH2-CH(methyl)-O-;

[0347] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R]-R4, R16, R17, or A are independently -SO3.

[0348] Also described herein are compounds of Formula V or salt thereof:

[0349] wherein:

[0350] R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A;

[0351] R2-R4are each independently H or -SO3;

[0352] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0353] EO represents -CH2-CH2-O-;

[0354] PO represents -CH2-CH(methyl)-O-;

[0355] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R1-R1, or A are independently -SO3.

[0356] Described are also compounds of Formula VI or salt thereof: wherein:

[0357] R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;

[0358] R2-R4are each independently H or -SO3;

[0359] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0360] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate; R16is alkene, C1-C32alkyl,

[0361] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0362] EO represents -CH2-CH2-O-;

[0363] PO represents -CH2-CH(methyl)-O-;

[0364] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R'-R4, R6, R7, R9, R12, R13, R15-R17or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0365] Described are also compounds of Formula VI or salt thereof: wherein:

[0366] R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A;

[0367] R2-R4are each independently H or -SO3;

[0368] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0369] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0370] EO represents -CH2-CH2-O-;

[0371] PO represents -CH2-CH(methyl)-O-; BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R'-R4, R6, R7, R9, R12, R13, R15or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0372] Also described herein are compounds of Formula VII or salt thereof: wherein:

[0373] R2-R4are each independently H or -SO3;

[0374] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R16, R17, or A are independently -SO3.

[0375] Also described herein are compounds of Formula VII or salt thereof: wherein:

[0376] R2-R4are each independently H or -SO3;

[0377] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0378] EO represents -CH2-CH2-O-;

[0379] PO represents -CH2-CH(methyl)-O-;

[0380] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, or A are independently -SO3.

[0381] Also described herein are compounds of Formula VIII or salt thereof: Formula VIII or Formula VIIIA wherein:

[0382] R2-R4are each independently H or -SO3;

[0383] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0384] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0385] R16is alkene, Ci -C32 alkyl,

[0386] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0387] EO represents -CH2-CH2-O-;

[0388] PO represents -CH2-CH(methyl)-O-;

[0389] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R6, R7, R9, R12, R13, R15-R17or A are independently -SO3; when: one of R6or R12is -SO3. then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0390] Also described herein are compounds of Formula VIII or salt thereof: Formula VIII or Formula VIIIA wherein:

[0391] R2-R4are each independently H or -SO3;

[0392] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0393] A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate;

[0394] EO represents -CH2-CH2-O-;

[0395] PO represents -CH2-CH(methyl)-O-;

[0396] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R6, R7, R9, R12, R13, R15or A are independently -SO3; when: one of R6or R12is -SO3. then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3. then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0397] Also described herein are compounds of Formula IX or salt thereof, Formula IXA or salt thereof, Formula IXB or salt thereof, Formula IXC or salt thereof, or Formula IXD or salt thereof: Formula IXB Formula IXC or

[0398] Formula IXD wherein:

[0399] R2-R4are each independently H or -SO3;

[0400] R6, R7, R9and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0401] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0402] R16is alkene, C1-C32alkyl,

[0403] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0404] BO represents -CH2-CH(ethyl)-O-;

[0405] EO represents -CH2-CH2-O-;

[0406] PO represents -CH2-CH(methyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; n, m, and q are each independently 0 to 6; the dotted line represents an optional double bond if valence permits; at least two of R2-R7, R9, R12-R13, R15-R17, or A are independently -SO3; and wherein when: one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl.

[0407] Also described herein are compounds of Formula X or salt thereof, Formula XA or salt thereof, Formula XB or salt thereof, Formula XC or salt thereof, or Formula XD or salt thereof:

[0408] Formula XD; wherein:

[0409] R2-R4are each independently H or -SO3;

[0410] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate; R16is alkene, C1-C32alkyl,

[0411] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-A;

[0412] EO represents -CH2-CH2-O-;

[0413] PO represents -CH2-CH(methyl)-O-; BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R16, R17, or A are independently -SO3. Also described herein are compounds of Formula XI or salt thereof, Formula XIA or salt thereof, Formula XIB or salt thereof, Formula XIC or salt thereof, or Formula XID or salt thereof:

[0414] wherein:

[0415] R2-R4are each independently H or -SO3;

[0416] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0417] R16is alkene, C1-C32alkyl,

[0418] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0419] EO represents -CH2-CH2-O-;

[0420] PO represents -CH2-CH(methyl)-O-;

[0421] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R16, R17, or A are independently -SO3.

[0422] Also described herein are compounds of Formula XII or salt thereof, Formula XIIA or salt thereof, Formula XIIB or salt thereof, Formula XIIC or salt thereof, or Formula XIID or salt thereof:

[0423]

[0424] Formula XIID wherein:

[0425] R2-R4are each independently H or -SO3;

[0426] R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0427] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0428] R16is alkene, C1-C32alkyl,

[0429] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0430] EO represents -CH2-CH2-O-;

[0431] PO represents -CH2-CH(methyl)-O-;

[0432] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R -R4, R6, R7, R9, R12, R13, R15-R17or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

[0433] In some embodiments, R2is H. In some embodiments, R3is H. In some embodiments, R5is H. In some embodiments, R2is -SO3. In some embodiments, R3is -SO3. In some embodiments, R5is -SO3. In some embodiments, R2, R3, and R5are -SO3. In some embodiments, R2, R3, and Rsare H. In some embodiments, R2and R5are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and Rsis H. In some embodiments, R3and Rsare -SO3, and R2is H. In some embodiments, R2and R5are H, and R3is -SO3. In some embodiments, R2and R3are H, and R5is -SO3. In some embodiments, R3and R5are H, and R2is -SO3.

[0434] In some embodiments, R6, R7, and R9are H. In some embodiments, R6, R7, and R9are - SO3. In some embodiments, R6, R7, and R9are -OH. In some embodiments, R6, R7, and R9are C1-C6alkyl. In some embodiments, R6, R7, and R9are each independently methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl.

[0435] In some embodiments, R12, R13, and R15are H. In some embodiments, R12, R13, and R15are -SO3. In some embodiments, R12, R13, and R1Sare -OH.

[0436] In some embodiments, when R6is OH, then R12is not OH. In some embodiments, when R12is OH, then R6is not OH. In some embodiments, when R6is OH, then R12is H or -SO3. In some embodiments, when R12is OH, then R6is H, -SO3or C1-C6alkyl. In some embodiments, when R9is OH, then R15is not OH. In some embodiments, when R15is OH, then R9is not OH. In some embodiments, when R9is OH, then R1Sis H or -SO3. In some embodiments, when R15is OH, then R9is H, -SO3or C1-C6alkyl. In some embodiments, when R7is OH, then R13is not OH. In some embodiments, when R13is OH, then R7is not OH. In some embodiments, when R7is OH, then R13is H or -SO3. In some embodiments, when R13is OH, then R7is H, -SO3or Ci- Ce alkyl.

[0437] In some embodiments, A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OR16. In some embodiments, A is -OH. In some embodiments, A is -OSO3. In some embodiments, A is -SO3. In some embodiments, A is alkene. In some embodiments, A is monocarboxylate. In some embodiments, A is dicarboxylate. In some embodiments, A is tricarboxylate. In some embodiments, R16is alkene, C1-C32alkyl, or

[0438] OH . in some embodiments, R16is alkene. In some embodiments, R16is C1-C32alkyl. In

[0439] R17some embodiments, R16is . In some embodiments, R16is . In some

[0440] OH embodiments, R16is . In some embodiments, R16is OH

[0441] In some embodiments, R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or - (BO)z(PO)x-(EO)y-A. In some embodiments, R17is H. In some embodiments, R17is C1-C32alkyl In some embodiments, R17is alkenyl. In some embodiments, R17is G,-Cis alkyl. In some embodiments, R17is aryl. In some embodiments, R17is C1-C24 alkyl. In some embodiments, R17is -(PO)x-(EO)y-A. In some embodiments, R17is -(BO)z(PO)x-(EO)y-A.

[0442] In some embodiments, x is 0 to 65, 0 to 60, 0 to 55, 0 to 50, 0 to 45, 0 to 40, 0 to 35, 0 to

[0443] 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 65, 1 to 60, 1 to 55, 1 to 50, 1 to 45, 1 to 40, 1 to 35, 1 to 30, 1 to 25, 1 to 20, 5 to 65, 5 to 60, 5 to 55, 5 to 50, 5 to 45, 5 to 40, 5 to 35, 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, 10 to 65, 10 to 60, 10 to 55, 10 to 50, 10 to 45, 10 to 40, 10 to 35, 10 to 30, 10 to 25, 10 to 20, 20 to 65, 20 to 60, 20 to 55, 20 to 50, 20 to 45, 20 to 40, 20 to 35, 20 to 30, 20 to 25, 30 to 65, 30 to 60, 30 to 55, 30 to 50, 30 to 45, 30 to 40, 30 to 35, 40 to 65, 40 to 60, 40 to 55, 40 to 50, 40 to 45, 50 to 65, 50 to 60, 50 to 55, or 60 to 65. In some embodiments, x is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, or 65. In some embodiments, x is 0.

[0444] In some embodiments, y is 0 to 100, 0 to 90, 0 to 80, 0 to 70, 0 to 60, 0 to 50, 0 to 40, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 20, 1 to 25, 1 to 30, 1 to 100, 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, 1 to 40, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 20, 5 to 10, 10 to 100, 10 to 90, 10 to 80, 10 to 70, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 20, 20 to 100, 20 to 90, 20 to 80, 20 to 70, 20 to 60, 20 to 50, 20 to 40, 20 to 30, 30 to 100, 30 to 90, 30 to 80, 30 to 70, 30 to 60, 30 to 50, 30 to 40, 40 to 100, 40 to 90, 40 to 80, 40 to 70, 40 to 60, 40 to 50, 50 to 100, 50 to 90, 50 to 80, 50 to 70, 50 to 60, 60 to 100, 60 to 90, 60 to 80, 60 to 70, 70 to 100, 70 to 90, 70 to 80, 80 to 100, 80 to 90, or 90 to 100. In some embodiments, y is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100.

[0445] In some embodiments, z is 0 to 10, 0 to 5, 1 to 5, 1 to 10, or 5 to 10. In some embodiments, z is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. In some embodiments, x is 0.

[0446] In some embodiments, y is 0. In some embodiments, y is 16. In some embodiments, z is

[0447] 0. In some embodiments, x is 0 and y is 16. In some embodiments, x is 0, y is 16, and z is 0.

[0448] In some embodiments, the compound can be selected from:

[0449] combination thereof.

[0450] Surfactant mixtures

[0451] Also described herein are surfactant mixtures including: a) a compound of Formula I or salt thereof:

[0452] any combination thereof; b) a compound of Formula II or salt thereof:

[0453] c) a compound of Formula III or salt thereof or a compound of Formula IIIA or salt

[0454] 5 thereof:

[0455] d) a compound of Formula IV or salt thereof or a compound of Formula IVA or salt

[0456] 5 thereof:

[0457] combination thereof; e) a compound of Formula V or salt thereof:

[0458] thereof; f) a compound of Formula VI or salt thereof: thereof; g) a compound of Formula VII or salt thereof or Formula VIIA or salt thereof:

[0459] or any combination thereof; h) a compound of Formula VIII or salt thereof or Formula VIII or salt thereof:

[0460] or any combination thereof; i) a compound of Formula IX or salt thereof, Formula IXA or salt thereof, Formula IXB or salt thereof, Formula IXC or salt thereof, Formula IXD or salt thereof: or any combination thereof; j) a compound of Formula X or salt thereof, Formula XA or salt thereof, Formula XB or salt thereof, Formula XC or salt thereof, or Formula XD or salt thereof:

[0461]

[0462] 5 k) a compound of Formula XI or salt thereof, Formula XIA or salt thereof, Formula XIB or salt thereof, Formula XIC or salt thereof, or Formula XID or salt thereof:

[0463] 1) a compound of Formula XII or salt thereof, Formula XIIA or salt thereof, Formula XIIB or salt thereof, Formula XIIC or salt thereof, or Formula XIID or salt thereof: wherein:

[0464] R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z(PO)x-(EO)y-A, or -OR16;

[0465] R2-R5are each independently H or -SO3;

[0466] R6-R9and R12-R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0467] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate; R16is alkene, C1-C32alkyl,

[0468] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0469] EO represents -CH2-CH2-O-;

[0470] PO represents -CH2-CH(methyl)-O-;

[0471] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; at least two of R'-R9, R12-R17or A are independently -SO3; and when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3. then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; or any combination thereof.

[0472] Also described herein are surfactant mixtures including: a) a compound of Formula I or salt thereof:

[0473] c) a compound of Formula III or salt thereof or a compound of Formula IIIA or salt thereof:

[0474] d) a compound of Formula IV or salt thereof or a compound of Formula IVA or salt

[0475] 5 thereof:

[0476] combination thereof; e) a compound of Formula V or salt thereof:

[0477] thereof; f) a compound of Formula VI or salt thereof: thereof; g) a compound of Formula VII or salt thereof or Formula VIIA or salt thereof:

[0478] or any combination thereof; h) a compound of Formula VIII or salt thereof or Formula VIII or salt thereof:

[0479] or any combination thereof; wherein:

[0480] R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z(PO)x-(EO)y-A, or -OR16;

[0481] R2-R5are each independently H or -SO3;

[0482] R6-R9and R12-R15are each independently H, -OH, -SO3, or C1-C6alkyl;

[0483] A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;

[0484] R16is alkene, C1-C32alkyl,

[0485] R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;

[0486] EO represents -CH2-CH2-O-;

[0487] PO represents -CH2-CH(methyl)-O-;

[0488] BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; at least two of R1-R9, R12-R17or A are independently -SO3; and when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; or any combination thereof.

[0489] In some embodiments, R1is -OH. In some embodiments, R1is -OSO3. In some embodiments, R1is -(PO)x-(EO)y-A. In some embodiments, R1is -(BO)z(PO)x-(EO)y-A. In embodiments, some embodiments, R1

[0490] In some embodiments, R2is H. In some embodiments, R3is H. In some embodiments, R4is H. In some embodiments, R5is H. In some embodiments, R2is -SO3. In some embodiments, R3is -SO3. In some embodiments, R4is -SO3. In some embodiments, R5is -SO3. In some embodiments, R2, R3, and R5are -SO3. In some embodiments, R2, R3, and R5are H. In some embodiments, R2and R5are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and R5is H. In some embodiments, R3and R5are -SO3, and R2is H. In some embodiments, R2and R5are H, and R3is -SO3. In some embodiments, R2and R3are H, and R5is -SO3. In some embodiments, R3and R5are H, and R2is -SO3. In some embodiments, R2, R3, and R4are -SO3. In some embodiments, R2, R3, and R4are H. In some embodiments, R2and R4are -SO3, and R3is H. In some embodiments, R2and R3are -SO3, and R4is H. In some embodiments, R3and R4are -SO3, and R2is H. In some embodiments, R2and R4are H, and R3is -SO3. In some embodiments, R2and R3are H, and R4is -SO3. In some embodiments, R3and R4are H, and R2is -SO3.

[0491] In some embodiments, when R1is -OH, -OSO3, -(PO)x-(EO)y-A, or -(BO)z-(PO)x-(EO)y-

[0492] A, -OR16, then some embodiments, when R1is -OH, -OSO3, -(PO)X- O

[0493] In some embodiments, R11is H. In some embodiments, embodiments,

[0494] In some embodiments, when R11is H, then embodiments, when R11is H, then is not -(BO)z-(PO)x-(EO)y-A.In some embodiments, n, m, p, and q are 0. In some embodiments, n, m, p, and q are 1. In some embodiments, n, m, p, and q are 2. In some embodiments, n, m, p, and q are 3. In some embodiments, n, m, p, and q are 4. In some embodiments, n, m, p, and q are 5. In some embodiments, n, m, p, and q are 6. In some embodiments, n, m, and q are 0. In some embodiments, n, m, and q are 1. In some embodiments, n, m, and q are 2. In some embodiments, n, m, and q are 3. In some embodiments, n, m, and q are 4. In some embodiments, n, m, and q are 5. In some embodiments, n, m, and q are 6. In some embodiments, n, m, and p are 1. In some embodiments, n, m, and p are 2. In some embodiments, n, m, and p are 3. In some embodiments, n, m, and p are 4. In some embodiments, n, m, and p are 5. In some embodiments, n, m, and p are 6.

[0495] In some embodiments, R6, R7, R8, and R9are H. In some embodiments, R6, R7, R8, and R9are -SO3. In some embodiments, R6, R7, R8, and R9are -OH. In some embodiments, R6, R7, R8, and R9are C1-C6alkyl. In some embodiments, R6, R7, R8, and R9are each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl.

[0496] In some embodiments, R6, R7, and R9are H. In some embodiments, R6, R7, and R9are - SO3. In some embodiments, R6, R7, and R9are -OH. In some embodiments, R6, R7, and R9are C1-C6alkyl. In some embodiments, R6, R7, and R9are each independently methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl. In some embodiments, R6, R7, and R9are methyl.

[0497] In some embodiments, R6, R7, and R8are H. In some embodiments, R6, R7, and R8are - SO3. In some embodiments, R6, R7, and R8are -OH. In some embodiments, R6, R7, and R8are C1-C6alkyl. In some embodiments, R6, R7, and R8are each independently methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, or hexyl.

[0498] In some embodiments, R12, R13, R14, and R15are H. In some embodiments, R12, R13, R14, and R15are -SO3. In some embodiments, R12, R13, R14, and R15are -OH. In some embodiments, R12, R13, and R15are H. In some embodiments, R12, R13, and R15are -SO3. In some embodiments, R12, R13, and R15are -OH. In some embodiments, R12, R13, and R14are H. In some embodiments, R12, R13, and R14are -SO3. In some embodiments, R12, R13, and R14are -OH.

[0499] In some embodiments, when R6is -OH, then R12is not -OH. In some embodiments, when R12is -OH, then R6is not -OH. In some embodiments, when R6is -OH, then R12is H or - SO3. In some embodiments, when R12is -OH, then R6is H, -SO3or C1-C6alkyl. In some embodiments, when R8is -OH, then R14is not -OH. In some embodiments, when R14is -OH, then R8is not -OH. In some embodiments, when R8is -OH, then R14is H or -SO3. In some embodiments, when R14is -OH, then R8is H, -SO3or C1-C6alkyl. In some embodiments, when R7is -OH, then R13is not -OH. In some embodiments, when R13is -OH, then R7is not -OH. In some embodiments, when R7is -OH, then R13is H or -SO3. In some embodiments, when R13is - -OH, then R7is H, -SO3or C1-C6alkyl. In some embodiments, when R9is -OH, then R15is not - OH. In some embodiments, when R15is -OH, then R9is not -OH. In some embodiments, when R9is -OH, then R15is H or -SO3. In some embodiments, when R15is -OH, then R9is H, -SO3or Ci-C6alkyl.

[0500] In some embodiments, A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OH, -OSO3, -SO3, monocarboxylate, dicarboxylate, or tricarboxylate. In some embodiments, A is -OR16. In some embodiments, A is -OH. In some embodiments, A is -OSO3. In some embodiments, A is -SO3. In some embodiments, A is alkene. In some embodiments, A is monocarboxylate. In some embodiments, A is dicarboxylate. In some embodiments, A is tricarboxylate.

[0501] In some embodiments, R16is alkene, C1-C32alkyl, , or . In some embodiments, R16is alkene. In some embodiments, R16is C1-C32alkyl. In some embodiments, . In some embodiments, . In some embodiments, R16is . ,

[0502] In some embodiments, R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or - (BO)z(PO)x-(EO)y-A. In some embodiments, R17is H. In some embodiments, R17is C1-C32alkyl. In some embodiments, R17is alkenyl. In some embodiments, R17is aryl. In some embodiments, R17is C6-C18alkyl. In some embodiments, R17is C1-C24 alkyl. In some embodiments, R17is - (PO)x-(EO)y-A. In some embodiments, R17is -(BO)z(PO)x-(EO)y-A.

[0503] In some embodiments, x is 0 to 65, 0 to 60, 0 to 55, 0 to 50, 0 to 45, 0 to 40, 0 to 35, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 65, 1 to 60, 1 to 55, 1 to 50, 1 to 45, 1 to 40, 1 to 35, 1 to 30, 1 to 25, 1 to 20, 5 to 65, 5 to 60, 5 to 55, 5 to 50, 5 to 45, 5 to 40, 5 to 35, 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, 10 to 65, 10 to 60, 10 to 55, 10 to 50, 10 to 45, 10 to 40, 10 to 35, 10 to 30, 10 to 25, 10 to 20, 20 to 65, 20 to 60, 20 to 55, 20 to 50, 20 to

[0504] 45, 20 to 40, 20 to 35, 20 to 30, 20 to 25, 30 to 65, 30 to 60, 30 to 55, 30 to 50, 30 to 45, 30 to

[0505] 40, 30 to 35, 40 to 65, 40 to 60, 40 to 55, 40 to 50, 40 to 45, 50 to 65, 50 to 60, 50 to 55, or 60 to

[0506] 65. In some embodiments, x is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,

[0507] 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, or 65. In some embodiments, x is 0.

[0508] In some embodiments, y is 0 to 100, 0 to 90, 0 to 80, 0 to 70, 0 to 60, 0 to 50, 0 to 40, 0 to 30, 0 to 25, 0 to 20, 0 to 15, 0 to 10, 0 to 5, 1 to 5, 1 to 10, 1 to 15, 1 to 20, 1 to 25, 1 to 30, 1 to 100, 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, 1 to 40, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 20, 5 to 10, 10 to 100, 10 to 90, 10 to 80, 10 to 70, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 20, 20 to 100, 20 to 90, 20 to 80, 20 to 70, 20 to 60, 20 to 50, 20 to 40, 20 to 30, 30 to 100, 30 to 90, 30 to 80, 30 to 70, 30 to 60, 30 to 50, 30 to 40, 40 to 100, 40 to 90, 40 to 80, 40 to 70, 40 to 60, 40 to 50, 50 to 100, 50 to 90, 50 to 80, 50 to 70, 50 to 60, 60 to 100, 60 to 90, 60 to 80, 60 to 70, 70 to 100, 70 to 90, 70 to 80, 80 to 100, 80 to 90, or 90 to 100. In some embodiments, y is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100.

[0509] In some embodiments, z is 0 to 10, 0 to 5, 1 to 5, 1 to 10, or 5 to 10. In some embodiments, z is 0, 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10. In some embodiments, x is 0.

[0510] In some embodiments, y is 0. In some embodiments, y is 16. In some embodiments, z is 0. In some embodiments, x is 0 and y is 16. In some embodiments, x is 0, y is 16, and z is 0.

[0511] Compositions

[0512] Described herein are also compositions comprising water and one or more compounds described herein or surfactant mixture described herein. In some embodiments, the composition comprises water and one or more compounds described herein. In some embodiments, the composition comprises a surfactant mixture described herein.

[0513] Optionally, the composition can include one or more additional components. For example, the composition can further comprise water, a co- surfactant, an acid, a polymer, a friction reducer, a gelling agent, a crosslinker, a scale inhibitor, a breaker, a pH adjusting agent, a non-emulsifier agent, an iron control agent, a corrosion inhibitor, a biocide, a clay stabilizing agent, a proppant, a wettability alteration chemical, a co-solvent (e.g., a C1-C5 alcohol, or an alkoxy lated C1-C5 alcohol), or any combination thereof.

[0514] In other embodiments, the co-surfactant can include an anionic surfactant, a cationic surfactant, a zwitterionic surfactant, an amphoteric surfactant, a non-ionic surfactant, or any combination thereof.

[0515] Suitable anionic surfactants for use as a primary surfactant and / or a secondary surfactant include a hydrophobic tail that comprises from 6 to 60 carbon atoms. In some embodiments, the anionic surfactant can include a hydrophobic tail that comprises at least 6 carbon atoms (e.g., at least 7 carbon atoms, at least 8 carbon atoms, at least 9 carbon atoms, at least 10 carbon atoms, at least 11 carbon atoms, at least 12 carbon atoms, at least 13 carbon atoms, at least 14 carbon atoms, at least 15 carbon atoms, at least 16 carbon atoms, at least 17 carbon atoms, at least 18 carbon atoms, at least 19 carbon atoms, at least 20 carbon atoms, at least 21 carbon atoms, at least 22 carbon atoms, at least 23 carbon atoms, at least 24 carbon atoms, at least 25 carbon atoms, at least 26 carbon atoms, at least 27 carbon atoms, at least 28 carbon atoms, at least 29 carbon atoms, at least 30 carbon atoms, at least 31 carbon atoms, at least 32 carbon atoms, at least 33 carbon atoms, at least 34 carbon atoms, at least 35 carbon atoms, at least 36 carbon atoms, at least 37 carbon atoms, at least 38 carbon atoms, at least 39 carbon atoms, at least 40 carbon atoms, at least 41 carbon atoms, at least 42 carbon atoms, at least 43 carbon atoms, at least 44 carbon atoms, at least 45 carbon atoms, at least 46 carbon atoms, at least 47 carbon atoms, at least 48 carbon atoms, at least 49 carbon atoms, at least 50 carbon atoms, at least 51 carbon atoms, at least 52 carbon atoms, at least 53 carbon atoms, at least 54 carbon atoms, at least 55 carbon atoms, at least 56 carbon atoms, at least 57 carbon atoms, at least 58 carbon atoms, or at least 59 carbon atoms). In some embodiments, the anionic surfactant can include a hydrophobic tail that comprises 60 carbon atoms or less (e.g., 59 carbon atoms or less, 58 carbon atoms or less, 57 carbon atoms or less, 56 carbon atoms or less, 55 carbon atoms or less, 54 carbon atoms or less, 53 carbon atoms or less, 52 carbon atoms or less, 51 carbon atoms or less, 50 carbon atoms or less, 49 carbon atoms or less, 48 carbon atoms or less, 47 carbon atoms or less, 46 carbon atoms or less, 45 carbon atoms or less, 44 carbon atoms or less, 43 carbon atoms or less, 42 carbon atoms or less, 41 carbon atoms or less, 40 carbon atoms or less, 39 carbon atoms or less, 38 carbon atoms or less, 37 carbon atoms or less, 36 carbon atoms or less, 35 carbon atoms or less, 34 carbon atoms or less, 33 carbon atoms or less, 32 carbon atoms or less, 31 carbon atoms or less, 30 carbon atoms or less, 29 carbon atoms or less, 28 carbon atoms or less, 27 carbon atoms or less, 26 carbon atoms or less, 25 carbon atoms or less, 24 carbon atoms or less, 23 carbon atoms or less, 22 carbon atoms or less, 21 carbon atoms or less, 20 carbon atoms or less, 19 carbon atoms or less, 18 carbon atoms or less, 17 carbon atoms or less, 16 carbon atoms or less, 15 carbon atoms or less, 14 carbon atoms or less, 13 carbon atoms or less, 12 carbon atoms or less, 11 carbon atoms or less, 10 carbon atoms or less, 9 carbon atoms or less, 8 carbon atoms or less, or 7 carbon atoms or less).

[0516] The anionic surfactant can include a hydrophobic tail that comprises a number of carbon atoms ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the anionic surfactant can comprise a hydrophobic tail comprising from 6 to 15, from 16 to 30, from 31 to 45, from 46 to 60, from 6 to 25, from 26 to 60, from 6 to 30, from 31 to 60, from 6 to 32, from 33 to 60, from 6 to 12, from 13 to 22, from 23 to 32, from 33 to 42, from 43 to 52, from 53 to 60, from 6 to 10, from 10 to 15, from 16 to 25, from 26 to 35, or from 36 to 45 carbon atoms. The hydrophobic (lipophilic) carbon tail may be a straight chain, branched chain, and / or may comprise cyclic structures. The hydrophobic carbon tail may comprise single bonds, double bonds, triple bonds, or any combination thereof. In some embodiments, the anionic surfactant can include a branched hydrophobic tail derived from Guerbet alcohols. The hydrophilic portion of the anionic surfactant can comprise, for example, one or more sulfate moieties (e.g., one, two, or three sulfate moieties), one or more sulfonate moieties (e.g., one, two, or three sulfonate moieties), one or more sulfosuccinate moieties (e.g., one, two, or three sulfosuccinate moieties), one or more carboxylate moieties (e.g., one, two, or three carboxylate moieties), or any combination thereof.

[0517] In some embodiments, the anionic surfactant can comprise, for example a sulfonate, a disulfonate, a polysulfonate, a sulfate, a disulfate, a polysulfate, a sulfosuccinate, a disulfosuccinate, a poly sulfosuccinate, a carboxylate, a dicarboxylate, a polycarboxylate, or any combination thereof. In some examples, the anionic surfactant can comprise an internal olefin sulfonate (IOS), an isomerized olefin sulfonate, an alfa olefin sulfonate (AOS), an alkyl aryl sulfonate (AAS), a xylene sulfonate, an alkane sulfonate, a petroleum sulfonate, an alkyl diphenyl oxide (di) sulfonate, an alcohol sulfate, an alkoxy sulfate, an alkoxy sulfonate, an alkoxy carboxylate, an alcohol phosphate, or an alkoxy phosphate. In some embodiments, the anionic surfactant can comprise an alkoxy carboxylate surfactant, an alkoxy sulfate surfactant, an alkoxy sulfonate surfactant, an alkyl sulfonate surfactant, an aryl sulfonate surfactant, or an olefin sulfonate surfactant.

[0518] An "alkoxy carboxylate surfactant" or "alkoxy carboxylate" refers to a compound having an alkyl or aryl attached to one or more alkoxylene groups (typically -CH2-CH (ethyl)-O-, -CH2- CH(methyl)-O-, or -CH2-CH2-O-) which, in turn is attached to -COO’ or acid or salt thereof including metal cations such as sodium. In embodiments, the alkoxy carboxylate surfactant can be defined by the formulae below: or wherein R1is substituted or unsubstituted C6-C36 alkyl or substituted or unsubstituted aryl; R2is, independently for each occurrence within the compound, hydrogen or unsubstituted C1-C6 alkyl; R3is independently hydrogen or unsubstituted C1-C6 alkyl, n is an integer from 0 to 175, z is an integer from 1 to 6 and M+is a monovalent, divalent or trivalent cation. In some of these embodiments, R1can be an unsubstituted linear or branched C6-C36 alkyl.

[0519] In certain embodiments, the alkoxy carboxylate can be a C6-C32:PO(0-65):EO(0-100)- carboxylate (i.e., a C6-C32 hydrophobic tail, such as a branched or unbranched C6-C32 alkyl group, attached to from 0 to 65 propyleneoxy groups (-CH2-CH(methyl)-O- linkers), attached in turn to from 0 to 100 ethyleneoxy groups (-CH2-CH2-O- linkers), attached in turn to -COO’ or an acid or salt thereof including metal cations such as sodium). In certain embodiments, the alkoxy carboxylate can be a branched or unbranched C6-C30:PO(30-40):EO(25-35)-carboxylate. In certain embodiments, the alkoxy carboxylate can be a branched or unbranched C6- C12:PO(30-40):EO(25-35)-carboxylate. In certain embodiments, the alkoxy carboxylate can be a branched or unbranched C6-C30:EO(8-30)-carboxylate.

[0520] An “alkoxy sulfate surfactant” or “alkoxy sulfate” refers to a surfactant having an alkyl or aryl attached to one or more alkoxylene groups (typically -CH2-CH(ethyl)-O-, -CH2- CH(methyl)-O-, or -CH2-CH2-O-) which, in turn is attached to -SO3’ or acid or salt thereof including metal cations such as sodium. In some embodiment, the alkoxy sulfate surfactant has the formula R-(BO)e-(PO)f-(EO)g-SO3’ or acid or salt (including metal cations such as sodium) thereof, wherein R is C6-C32 alkyl, BO is -CH2-CH(ethyl)-O-, PO is -CH2-CH (methyl)-O-, and EO is -CH2-CH2-O-. The symbols e, f and g are integers from 0 to 50 wherein at least one is not zero. In some embodiments, the alkoxy sulfate surfactant can be an aryl alkoxy sulfate surfactant. The aryl alkoxy surfactant can be an alkoxy surfactant having an aryl attached to one or more alkoxylene groups (typically -CH2-CH(ethyl)-O-, -CH2-CH(methyl)-0-, or -CH2-CH2- O-) which, in turn is attached to -SO f or acid or salt thereof including metal cations such as sodium.

[0521] An “alkyl sulfonate surfactant” or “alkyl sulfonate” refers to a compound that includes an alkyl group (e.g., a branched or unbranched C6-C32 alkyl group) attached to -SO3" or acid or salt thereof including metal cations such as sodium.

[0522] An “aryl sulfate surfactant” or “aryl sulfate” refers to a compound having an aryl group attached to -O-SO3or acid or salt thereof including metal cations such as sodium. An “aryl sulfonate surfactant” or “aryl sulfonate” refers to a compound having an aryl group attached to - SO3" or acid or salt thereof including metal cations such as sodium. In some cases, the aryl group can be substituted, for example, with an alkyl group (an alkyl aryl sulfonate).

[0523] An “internal olefin sulfonate,” “isomerized olefin sulfonate,” or “IOS” in the context of co- surfactants present in addition to the olefin sulfonates described herein refers to an unsaturated hydrocarbon compound comprising at least one carbon-carbon double bond and at least one SO3’ group, or a salt thereof. As used herein, a “C20-C28 internal olefin sulfonate,” “a C20-C28 isomerized olefin sulfonate,” or “C20-C28 IOS” refers to an IOS, or a mixture of IOSS with an average carbon number of 20 to 28, or of 23 to 25. The C20-C28 IOS may comprise at least 80% of IOS with carbon numbers of 20 to 28, at least 90% of IOS with carbon numbers of 20 to 28, or at least 99% of IOS with carbon numbers of 20 to 28. As used herein, a “C15-C18 internal olefin sulfonate,” “C15-C18 isomerized olefin sulfonate,” or “C15-C18 IOS” refers to an IOS or a mixture of IOSs with an average carbon number of 15 to 18, or of 16 to 17. The C15- C18 IOS may comprise at least 80% of IOS with carbon numbers of 15 to 18, at least 90% of IOS with carbon numbers of 15 to 18, or at least 99% of IOS with carbon numbers of 15 to 18. The internal olefin sulfonates or isomerized olefin sulfonates may be alpha olefin sulfonates, such as an isomerized alpha olefin sulfonate. The internal olefin sulfonates or isomerized olefin sulfonates may also comprise branching. In certain embodiments, Cl 5- 18 IOS may be added to surfactant packages when used for low particle size injection fluids intended for use in high temperature unconventional subterranean formations, such as formations above 130°F (approximately 55 °C). The IOS may be at least 20% branching, 30% branching, 40% branching, 50% branching, 60% branching, or 65% branching. In some embodiments, the branching is between 20-98%, 30-90%, 40-80%, or around 65%. Examples of internal olefin sulfonates and the methods to make them are found in U.S. Pat. No. 5,488,148, U.S. Patent Application Publication 2009 / 0112014, and SPE 129766, all incorporated herein by reference.

[0524] In embodiments, the anionic surfactant can be a disulfonate, alkyldiphenyloxide disulfonate, mono alkyldiphenyloxide disulfonate, di alkyldiphenyloxide disulfonate, or a di alkyldiphenyloxide monosulfonate, where the alkyl group can be a C6-C36 linear or branched alkyl group. In embodiments, the anionic surfactant can be an alkylbenzene sulfonate or a dibenzene disufonate. In embodiments, the anionic surfactant can be benzenesulfonic acid, decyl(sulfophenoxy)-disodium salt; linear or branched C6-C36 alkyl:PO(0-65):EO(0-100) sulfate; or linear or branched C6-C36 alkyl:PO(0-65):EO(0-100) carboxylate. In embodiments, the anionic surfactant is an isomerized olefin sulfonate (C6-C30), internal olefin sulfonate (C6- C30) or internal olefin disulfonate (C6-C30). In some embodiments, the anionic surfactant is a Guerbet-PO(0-65)-EO(0-100) sulfate (Guerbet portion can be C6-C36). In some embodiments, the anionic surfactant is a Guerbet-PO(0-65)-EO(0-100) carboxylate (Guerbet portion can be C6- C36). In some embodiments, the anionic surfactant is alkyl PO(0-65) and EO(O-IOO) sulfonate: where the alkyl group is linear or branched C6-C36. In some embodiments, the anionic surfactant is a sulfosuccinate, such as a dialkylsulfosuccinate. In some embodiments, the anionic surfactant is an alkyl aryl sulfonate (AAS) (e.g. an alkyl benzene sulfonate (ABS)), a C10-C30 internal olefin sulfate (IOS), a petroleum sulfonate, or an alkyl diphenyl oxide (di)sulfonate.

[0525] In some examples, the anionic surfactant can comprise a surfactant defined by the formula below:

[0526] R1— R2— R3wherein R1comprises a branched or unbranched, saturated or unsaturated, cyclic or non- cyclic, hydrophobic carbon chain having 6-32 carbon atoms and an oxygen atom linking R1and R2; R2comprises an alkoxylated chain comprising at least one oxide group selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and any combination thereof; and R3comprises a branched or unbranched hydrocarbon chain comprising 2-12 carbon atoms and from 2 to 5 carboxylate groups.

[0527] In some examples, the anionic surfactant can comprise a surfactant defined by the formula below: wherein R4is, independently for each occurrence, a branched or unbranched, saturated or unsaturated, cyclic or non-cyclic, hydrophobic carbon chain having 6-32 carbon atoms; and M represents a counterion (e.g., Na+, K+). In some embodiments, R4is a branched or unbranched, saturated or unsaturated, cyclic or non-cyclic, hydrophobic carbon chain having 6-16 carbon atoms.

[0528] In some embodiments, non-ionic surfactants may be used as the primary surfactant and / or secondary surfactant. Suitable non-ionic surfactants include compounds that can be added to increase wettability. In some embodiments, the hydrophilic-lipophilic balance (HLB) of the non-ionic surfactant is greater than 10 (e.g., greater than 9, greater than 8, or greater than 7). In some embodiments, the HLB of the non-ionic surfactant is from 7 to 10.

[0529] The non-ionic surfactant can comprise a hydrophobic tail comprising from 6 to 60 carbon atoms. In some embodiments, the non-ionic surfactant can include a hydrophobic tail that comprises at least 6 carbon atoms (e.g., at least 7 carbon atoms, at least 8 carbon atoms, at least 9 carbon atoms, at least 10 carbon atoms, at least 11 carbon atoms, at least 12 carbon atoms, at least 13 carbon atoms, at least 14 carbon atoms, at least 15 carbon atoms, at least 16 carbon atoms, at least 17 carbon atoms, at least 18 carbon atoms, at least 19 carbon atoms, at least 20 carbon atoms, at least 21 carbon atoms, at least 22 carbon atoms, at least 23 carbon atoms, at least 24 carbon atoms, at least 25 carbon atoms, at least 26 carbon atoms, at least 27 carbon atoms, at least 28 carbon atoms, at least 29 carbon atoms, at least 30 carbon atoms, at least 31 carbon atoms, at least 32 carbon atoms, at least 33 carbon atoms, at least 34 carbon atoms, at least 35 carbon atoms, at least 36 carbon atoms, at least 37 carbon atoms, at least 38 carbon atoms, at least 39 carbon atoms, at least 40 carbon atoms, at least 41 carbon atoms, at least 42 carbon atoms, at least 43 carbon atoms, at least 44 carbon atoms, at least 45 carbon atoms, at least 46 carbon atoms, at least 47 carbon atoms, at least 48 carbon atoms, at least 49 carbon atoms, at least 50 carbon atoms, at least 51 carbon atoms, at least 52 carbon atoms, at least 53 carbon atoms, at least 54 carbon atoms, at least 55 carbon atoms, at least 56 carbon atoms, at least 57 carbon atoms, at least 58 carbon atoms, or at least 59 carbon atoms). In some embodiments, the non-ionic surfactant can include a hydrophobic tail that comprises 60 carbon atoms or less (e.g., 59 carbon atoms or less, 58 carbon atoms or less, 57 carbon atoms or less, 56 carbon atoms or less, 55 carbon atoms or less, 54 carbon atoms or less, 53 carbon atoms or less, 52 carbon atoms or less, 51 carbon atoms or less, 50 carbon atoms or less, 49 carbon atoms or less, 48 carbon atoms or less, 47 carbon atoms or less, 46 carbon atoms or less, 45 carbon atoms or less, 44 carbon atoms or less, 43 carbon atoms or less, 42 carbon atoms or less, 41 carbon atoms or less, 40 carbon atoms or less, 39 carbon atoms or less, 38 carbon atoms or less, 37 carbon atoms or less, 36 carbon atoms or less, 35 carbon atoms or less, 34 carbon atoms or less, 33 carbon atoms or less, 32 carbon atoms or less, 31 carbon atoms or less, 30 carbon atoms or less, 29 carbon atoms or less, 28 carbon atoms or less, 27 carbon atoms or less, 26 carbon atoms or less, 25 carbon atoms or less, 24 carbon atoms or less, 23 carbon atoms or less, 22 carbon atoms or less, 21 carbon atoms or less, 20 carbon atoms or less, 19 carbon atoms or less, 18 carbon atoms or less, 17 carbon atoms or less, 16 carbon atoms or less, 15 carbon atoms or less, 14 carbon atoms or less, 13 carbon atoms or less, 12 carbon atoms or less, 11 carbon atoms or less, 10 carbon atoms or less, 9 carbon atoms or less, 8 carbon atoms or less, or 7 carbon atoms or less).

[0530] The non-ionic surfactant can include a hydrophobic tail that comprises a number of carbon atoms ranging from any of the minimum values described above to any of the maximum values described above. For example, the non-ionic surfactant can comprise a hydrophobic tail comprising from 6 to 15, from 16 to 30, from 31 to 45, from 46 to 60, from 6 to 25, from 26 to 60, from 6 to 30, from 31 to 60, from 6 to 32, from 33 to 60, from 6 to 12, from 13 to 22, from 23 to 32, from 33 to 42, from 43 to 52, from 53 to 60, from 6 to 10, from 10 to 15, from 16 to 25, from 26 to 35, or from 36 to 45 carbon atoms. In some cases, the hydrophobic tail may be a straight chain, branched chain, and / or may comprise cyclic structures. The hydrophobic carbon tail may comprise single bonds, double bonds, triple bonds, or any combination thereof. In some cases, the hydrophobic tail can comprise an alkyl group, with or without an aromatic ring (e.g., a phenyl ring) attached to it. In some embodiments, the hydrophobic tail can comprise a branched hydrophobic tail derived from Guerbet alcohols.

[0531] Example non-ionic surfactants include alkyl aryl alkoxy alcohols, alkyl alkoxy alcohols, or any combination thereof. In embodiments, the non-ionic surfactant may be a mix of surfactants with different length lipophilic tail chain lengths. For example, the non-ionic surfactant may be C9-C11 :9EO, which indicates a mixture of non-ionic surfactants that have a lipophilic tail length of 9 carbon to 11 carbon, which is followed by a chain of 9 EOs. The hydrophilic moiety is an alkyleneoxy chain (e.g., an ethoxy (EO), butoxy (BO) and / or propoxy (PO) chain with two or more repeating units of EO, BO, and / or PO). In some embodiments, 1 - 100 repeating units of EO are present. In some embodiments, 0-65 repeating units of PO are present. In some embodiments, 0-25 repeating units of BO are present. For example, the nonionic surfactant could comprise 10EO:5PO or 5EO. In embodiments, the non-ionic surfactant may be a mix of surfactants with different length lipophilic tail chain lengths. For example, the non-ionic surfactant may be C9-C11 :PO9:EO2, which indicates a mixture of non-ionic surfactants that have a lipophilic tail length of 9 carbon to 11 carbon, which is followed by a chain of 9 POs and 2 EOs. In specific embodiments, the non-ionic surfactant is linear C9- C11:9EO. In some embodiments, the non-ionic surfactant is a Guerbet PO(0-65) and EO(O-IOO) (Guerbet can be C6-C36); or alkyl PO(0-65) and EO(O-IOO): where the alkyl group is linear or branched C1-C36. In some examples, the non-ionic surfactant can comprise a branched or unbranched C6-C32:PO(0-65):EO(0-100) (e.g., a branched or unbranched C6-C30:PO(30- 40):EO(25-35), a branched or unbranched C6-C12:PO(30-40):EO(25-35), a branched or unbranched C6-30:EO(8-30), or any combination thereof). In some embodiments, the non-ionic surfactant is one or more alkyl polyglucosides.

[0532] Example cationic surfactants include surfactant analogous to those described above, except bearing primary, secondary, or tertiary amines, or quaternary ammonium cations, as a hydrophilic head group. "Zwitterionic" or "zwitterion" as used herein refers to a neutral molecule with a positive (or cationic) and a negative (or anionic) electrical charge at different locations within the same molecule. Example zwitterionic surfactants include betains and sultains.

[0533] Examples of other suitable surfactants include those disclosed, for example, in U.S. Patent Nos. 8,372,788 and 9,988,346, each of which is hereby incorporated by reference herein in its entirety. Examples of suitable surfactants are disclosed, for example, in U.S. Patent Nos. 3,811,504, 3,811,505, 3,811,507, 3,890,239, 4,463,806, 6,022,843, 6,225,267, 7,629,299, 7,770,641, 9,976,072, 8,211, 837, 9,422,469, 9,605,198, 10,233,382, and 9,617,464; WIPO Patent Application Nos. WO / 2008 / 079855, WO / 2012 / 027757 and WO / 2011 / 094442; as well as U.S. Patent Application Nos. 2005 / 0199395, 2006 / 0185845, 2006 / 0189486, 2009 / 0270281, 2011 / 0046024, 2011 / 0100402, 2011 / 0190175, 2007 / 0191633, 2010 / 004843. 2011 / 0201531, 2011 / 0190174, 2011 / 0071057, 2011 / 0059873, 2011 / 0059872, 2011 / 0048721, 2010 / 0319920, 2010 / 0292110, 2019 / 0153299, and 2017 / 0198202, each of which is hereby incorporated by reference herein in its entirety for its description of example surfactants. In some embodiments, the composition can further include one or more co-solvents. Suitable co-solvents include alcohols, such as lower carbon chain alcohols such as isopropyl alcohol, ethanol, n-propyl alcohol, n-butyl alcohol, sec -butyl alcohol, n-amyl alcohol, sec-amyl alcohol, n-hexyl alcohol, sec -hexyl alcohol and the like; alcohol ethers, polyalkylene alcohol ethers, polyalkylene glycols, poly(oxyalkylene)glycols, poly(oxyalkylene)glycol ethers, ethoxylated phenol, or any other common organic co-solvent or any combination of any two or more co-solvents. In one embodiment, the co-solvent can comprise alkyl ethoxylate (C1-C6)- XEO X=l-30 -linear or branched. In some embodiments, the co-solvent can comprise ethylene glycol butyl ether (EGBE), diethylene glycol monobutyl ether (DGBE), triethylene glycol monobutyl ether (TEGBE), ethylene glycol dibutyl ether (EGDE), polyethylene glycol monomethyl ether (mPEG), or any combination thereof. In some cases, the co-solvent can comprise an alcohol such as isopropyl alcohol (IP A), isobutyl alcohol (IBA), secondary butyl alcohol (SBA), or any combination thereof.

[0534] In some embodiments, the composition can have a concentration of a compound described herein within the composition of at least 0.05% by weight, based on the total weight of the composition (e.g., at least 0.1% by weight, at least 0.5% by weight, at least 1% by weight, at least 1.5% by weight, at least 2% by weight, at least 2.5% by weight, at least 3% by weight, at least 3.5% by weight, at least 4% by weight, at least 4.5% by weight).

[0535] In some embodiments, the composition can have a concentration of a compound described herein within the composition of 5% by weight or less, based on the total weight of the composition (e.g., 4.5% by weight or less, 4% by weight or less, 3.5% by weight or less, 3% by weight or less, 2.5% by weight or less, 2% by weight or less, 1.5% by weight or less, 1% by weight or less, 0.5% by weight or less, or 0.1% by weight or less).

[0536] For example, in some embodiments, the composition can have a concentration of a compound described herein within the composition of from 0.05% to 5% by weight, based on the total weight of the composition (e.g., from 0.05% to 4.5% by weight, from 0.05% to 4% by weight, from 0.05% to 3.5% by weight, from 0.05% to 3% by weight, from 0.05% to 2.5% by weight, from 0.05% to 2% by weight, from 0.05% to 1.5% by weight, from 0.05% to 1% by weight, from 0.05% to 0.5% by weight, from 0.05% to 0.1% by weight, from 0.1% to 4.5% by weight, from 0.1% to 4% by weight, from 0.1% to 3.5% by weight, from 0.1% to 3% by weight, from 0.1% to 2.5% by weight, from 0.1% to 2% by weight, from 0.1% to 1.5% by weight, from 0.1 % to 1% by weight, from 0.1% to 0.5% by weight, from 0.5% to 4.5% by weight, from 0.5% to 4% by weight, from 0.5% to 3.5% by weight, from 0.5% to 3% by weight, from 0.5% to 2.5% by weight, from 0.5% to 2% by weight, from 0.5% to 1.5% by weight, from 0.5% to 1% by weight, from 1% to 4.5% by weight, from 1% to 4% by weight, from 1% to 3.5% by weight, from 1% to 3% by weight, from 1% to 2.5% by weight, from 1% to 2% by weight, from 2% to 4.5% by weight, from 2% to 4% by weight, from 2% to 3.5% by weight, from 2% to 3% by weight, from 2% to 2.5% by weight, from 3% to 4.5% by weight, from 3% to 4% by weight, from 3% to 3.5% by weight, from 4% to 4.5% by weight, from 0.1% to 5% by weight, from 0.5% to 5% by weight, from 1% to 5% by weight, from 2% to 5% by weight, from 3% to 5% by weight, or from 4% to 5% by weight).

[0537] In some embodiments, the one or more co- surfactants can have a concentration of a compound described herein within the composition of at least 0.05% by weight, based on the total weight of the composition (e.g., at least 0.1% by weight, at least 0.5% by weight, at least 1% by weight, at least 1.5% by weight, at least 2% by weight, at least 2.5% by weight, at least 3% by weight, at least 3.5% by weight, at least 4% by weight, or at least 4.5% by weight).

[0538] In some embodiments, the one or more co- surfactants can have a concentration of a compound described herein within the composition of 5% by weight or less, based on the total weight of the composition (e.g., 4.5% by weight or less, 4% by weight or less, 3.5% by weight or less, 3% by weight or less, 2.5% by weight or less, 2% by weight or less, 1.5% by weight or less, 1 % by weight or less, 0.5% by weight or less, or 0.1 % by weight or less).

[0539] For example, in some embodiments, the one or more co-surfactants can have a concentration of a compound described herein within the composition of from 0.05% to 5% by weight, based on the total weight of the composition (e.g., from 0.05% to 4.5% by weight, from 0.05% to 4% by weight, from 0.05% to 3.5% by weight, from 0.05% to 3% by weight, from 0.05% to 2.5% by weight, from 0.05% to 2% by weight, from 0.05% to 1.5% by weight, from 0.05% to 1% by weight, from 0.05% to 0.5% by weight, from 0.05% to 0.1% by weight, from 0.1% to 4.5% by weight, from 0.1% to 4% by weight, from 0.1% to 3.5% by weight, from 0.1% to 3% by weight, from 0.1% to 2.5% by weight, from 0.1% to 2% by weight, from 0.1% to 1.5% by weight, from 0.1% to 1% by weight, from 0.1% to 0.5% by weight, from 0.5% to 4.5% by weight, from 0.5% to 4% by weight, from 0.5% to 3.5% by weight, from 0.5% to 3% by weight, from 0.5% to 2.5% by weight, from 0.5% to 2% by weight, from 0.5% to 1.5% by weight, from 0.5% to 1% by weight, from 1% to 4.5% by weight, from 1% to 4% by weight, from 1% to 3.5% by weight, from 1% to 3% by weight, from 1% to 2.5% by weight, from 1% to 2% by weight, from 2% to 4.5% by weight, from 2% to 4% by weight, from 2% to 3.5% by weight, from 2% to 3% by weight, from 2% to 2.5% by weight, from 3% to 4.5% by weight, from 3% to 4% by weight, from 3% to 3.5% by weight, from 4% to 4.5% by weight, from 0.1% to 5% by weight, from 0.5% to 5% by weight, from 1% to 5% by weight, from 2% to 5% by weight, from 3% to 5% by weight, or from 4% to 5% by weight).

[0540] The water used to form the compositions can include any type of water, treated or untreated, and can vary in salt content. For example, the aqueous solution can include sea water, brackish water, flowback or produced water, wastewater (e.g., reclaimed or recycled), brine (e.g., reservoir or synthetic brine), fresh water (e.g., fresh water comprises < 1,000 ppm TDS water), or any combination thereof. In certain examples, the water can include hard water or hard brine. In some embodiments, the water can include at least 10 ppm of divalent metal ions e.g., at least 100 ppm, at least 500 ppm, at least 1,000 ppm, at least 5,000 ppm, at least 10,000 ppm, at least 20,000 ppm, or at least 30,000 ppm). In some embodiments, the water can include 30,000 ppm or less of divalent metal ions (e.g., 20,000 ppm or less, 10,000 ppm or less, 5,000 ppm or less, 1,000 ppm or less, 500 ppm or less, 100 ppm or less, or 50 ppm or less). In certain embodiments, the from 10 ppm to 30,000 ppm of divalent metal ions.

[0541] The water can have a concentration of divalent metal ions ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the water can include from 10 ppm to 30,000 ppm of divalent metal ions (e.g., from 50 ppm to 30,000 ppm, from 100 ppm to 30,000 ppm, from 500 ppm to 30,000 ppm, from 1000 ppm to 30,000 ppm, from 5000 ppm to 30,000 ppm, from 10,000 ppm to 30,000 ppm, from 20,000 ppm to 30,000 ppm, from 10 ppm to 20,000 ppm, from 50 ppm to 20,000 ppm, from 100 ppm to 20,000 ppm, from 500 ppm to 20,000 ppm, from 1000 ppm to 20,000 ppm, from 5000 ppm to 20,000 ppm, from 10,000 ppm to 20,000 ppm, from 10 ppm to 10,000 ppm, from 50 ppm to 10,000 ppm, from 100 ppm to 10,000 ppm, from 500 ppm to 10,000 ppm, from 1000 ppm to 10,000 ppm, from 5000 ppm to 10,000 ppm, from 10 ppm to 5,000 ppm, from 50 ppm to 5,000 ppm, from 100 ppm to 5,000 ppm, from 500 ppm to 5,000 ppm, from 1000 ppm to 5,000 ppm, from 10 ppm to 1,000 ppm, from 50 ppm to 1,000 ppm, from 100 ppm to 20,000 ppm, from 500 ppm to 1,000 ppm, from 10 ppm to 500 ppm, from 50 ppm to 500 ppm, from 100 ppm to 500 ppm, from 10 ppm to 100 ppm, from 50 ppm to 100 ppm, or from 10 ppm to 50 ppm). In some embodiments, the divalent metal ions can be chosen from Ca2+, Mg2+, Sr2+, and Ba2+, or any combination thereof. In some embodiments, the composition can further include an unreacted starting material for synthesis, a byproduct remaining from synthesis, or any combination thereof.

[0542] Methods

[0543] Described are methods of using the compounds and surfactant mixtures as described herein (as well as the resulting compositions) in oil and gas operations. The oil and gas operation can comprise for example, an enhanced oil recovery (EOR) operation (e.g., an improved oil recovery (IOR) operation, a surfactant (S) flooding operation, an alkaline-surfactant (AS) flooding operation, a surfactant-polymer (SP) flooding operation, a alkaline-surfactant-polymer (ASP) flooding operation, or any combination thereof) a hydraulic fracturing operation, a wellbore clean-up operation, a stimulation operation, or any combination thereof. Compounds and surfactant mixtures as described herein (as well as the resulting compositions) can be optimized for each formation and / or for the desired oil and gas operation. For example, compounds and compositions described herein can be tested at a specific reservoir temperature and salinity, and with specific additional components. Actual native reservoir fluids may also be used to test the compositions.

[0544] Provided herein are methods of preventing asphaltene aggregation in a formation including: contacting a hydrocarbon containing asphaltene with a compound described herein, the surfactant mixture described herein, a composition described herein, a styryl phenol sulfonate compound, or any combination thereof.

[0545] In some embodiments, described are methods for treating a formation, the method comprising: introducing an aqueous fluid comprising water and a compound described herein, a surfactant mixture described herein, a composition described herein, a styryl phenol sulfonate compound, or any combination thereof through a wellbore into the subterranean formation, wherein a hydrocarbon in the formation can include an asphaltene concentration of from 0.5% to 17%, such as from 1% to 15%, from 3% to 15%, from 5% to 15%, or from 7% to 15%.

[0546] In certain examples, the compositions described herein can be used as an injection fluid, as a component of an injection fluid, as a hydraulic fracturing fluid, or as a component of a hydraulic fracturing fluid.

[0547] For example, provided herein methods for treating a formation, the method comprising: introducing an aqueous fluid comprising water and a compound described herein, a surfactant mixture described herein, a composition described herein, or any combination thereof through a wellbore into the formation. In some embodiments, the formation is a subterranean formation. The subterranean formation can be a subsea reservoir and / or subsurface reservoir.

[0548] In some embodiments, the compositions described herein can be used in treatment operations in an unconventional subterranean formation. For example, the aqueous fluid (injection compositions) described herein can be used as part of a completion and / or fracturing operation. Accordingly, methods of treating the formation can comprise a fracturing operation. For example, the method can comprise injecting the aqueous fluid into the subterranean formation through the wellbore at a sufficient pressure to create or extend at least one fracture in a rock matrix of the subterranean formation in fluid communication with the wellbore.

[0549] In certain embodiments, the fracturing operation can include combining a compound described herein and / or a surfactant mixture described herein with one or more additional components to form an injection composition; and injecting the injection composition through a wellbore and into the unconventional subterranean formation at a sufficient pressure and at a sufficient rate to fracture the unconventional subterranean formation. In some embodiments, the wellbore is a hydraulic fracturing wellbore associated with a hydraulic fracturing well, for example, that may have a substantially vertical portion only, or a substantially vertical portion and a substantially horizontal portion below the substantially vertical portion. In some embodiments, the fracturing operation can be performed in a new well (e.g., a well that has not been previously fractured). In other embodiments, the injection composition can be used in a fracturing operation in an existing well (e.g., in a refracturing operation).

[0550] In some embodiments, the method can comprise performing a fracturing operation on a region of the unconventional subterranean formation proximate to a new wellbore. In some embodiments, the method can comprise performing a fracturing operation on a region of the unconventional subterranean formation proximate to an existing wellbore. In some embodiments, the method can comprise performing a refracturing operation on a previously fractured region of the unconventional subterranean formation proximate to a new wellbore. In some embodiments, the method can comprise performing a refracturing operation on a previously fractured region of the unconventional subterranean formation proximate to an existing wellbore. In some embodiments, the method can comprise performing a fracturing operation on a naturally fractured region of the unconventional subterranean formation proximate to a new wellbore (e.g., an infill well). In some embodiments, the method can comprise performing a fracturing operation on a naturally fractured region of the unconventional subterranean formation proximate to an existing wellbore.

[0551] In cases where the fracturing method comprises a refracturing method, the previously fractured region of the unconventional reservoir can have been fractured by any suitable type of fracturing operation. For example, the fracturing operation may include hydraulic fracturing, fracturing using electrodes such as described in U.S. Patent No. 9,890,627 (Attorney Dkt. No. T- 9622A), U.S. Patent No. 9,840,898 (Attorney Dkt. No. T-9622B), U.S. Patent Publication No. 2018 / 0202273 (Attorney Dkt. No. T-9622A-CIP), or fracturing with any other available equipment or methodology. In some embodiments, the fracturing operation can further comprise adding a tracer to the injection composition prior to introducing the injection composition through the wellbore into the unconventional subterranean formation; recovering the tracer from the fluids produced from the unconventional subterranean formation through the wellbore, fluids recovered from a different wellbore in fluid communication with the unconventional subterranean formation, or any combination thereof; and comparing the quantity of tracer recovered from the fluids produced to the quantity of tracer introduced to the injection composition. The tracer can comprise a proppant tracer, an oil tracer, a water tracer, or any combination thereof. Example tracers are known in the art, and described, for example, in U.S. Pat. No. 9,914,872 and Ashish Kumar et al., Diagnosing Fracture-Wellbore Connectivity Using Chemical Tracer Flowback Data, URTeC 2902023, July 23-25, 2018, page 1-10, Texas, USA.

[0552] The injection composition can be used at varying points throughout a fracturing operation. For example, the injection compositions described herein can be used as an injection fluid during the first, middle or last part of the fracturing process, or throughout the entire fracturing process. In some embodiments, the fracturing process can include a plurality of stages and / or sub-stages. For example, the fracturing process can involve sequential injection of fluids in different stages, with each of the stages employing a different aqueous-based injection fluid system (e.g., with varying properties such as viscosity, chemical composition, etc.). Example fracturing processes of this type are described, for example, in U.S. Patent Application Publication Nos. 2009 / 0044945 and 2015 / 0083420, each of which is hereby incorporated herein by reference in its entirely.

[0553] In these embodiments, the injection compositions described herein can be used as an injection fluid (optionally with additional components) during any or all of the stages and / or substages. Stages and / or sub-stages can employ a wide variety of aqueous-based injection fluid systems, including linear gels, crosslinked gels, and friction-reduced water. Linear gel fracturing fluids are formulated with a wide array of different polymers in an aqueous base. Polymers that are commonly used to formulate these linear gels include guar, hydroxypropyl guar (HPG), carboxymethyl HPG (CMHPG), and hydroxyethyl cellulose (HEC). Crosslinked gel fracturing fluids utilize, for example, borate ions to crosslink the hydrated polymers and provide increased viscosity.

[0554] In some embodiments, the compounds, surfactant mixtures, or any combination described herein can be optionally combined with one or more additional components in a continuous process to form the injection compositions described herein (which is subsequently injected). In other embodiments, the compounds, surfactant mixtures, or any combination described herein can be optionally intermittently added to one or more additional components, thereby providing the injections compositions only during desired portions of the treatment operation (e.g., during one or more phases or stages of a fracturing operation). For example, the compounds, surfactant mixtures, or any combination described herein could be added when injecting slickwater, when injecting fracturing fluid with proppant, during an acid wash, or during any combination thereof. In a specific embodiment, the compounds, surfactant mixtures, or any combination described herein are continuously added to the one or more additional components after acid injection until completion of hydraulic fracturing and completion fluid flow-back. When intermittently dosed, the compounds, surfactant mixtures, or any combination described herein can be added to the one or more additional components once an hour, once every 2 hours, once every 4 hours, once every 5 hours, once every 6 hours, twice a day, once a day, or once every other day, for example. In some embodiments when used in a fracturing operation, the injection composition can have a total surfactant concentration of from 0.01% to 1% by weight, based on the total weight of the injection composition.

[0555] In some embodiments, the injection compositions described herein can be used as part of a reservoir stimulation operation (also referred to as wellbore cleanup operations or nearwellbore cleanup operations). The stimulation operation can be performed on a conventional subterranean formation or an unconventional subterranean formation. The stimulation operation can be performed on a subterranean formation that is fractured (naturally fractured and / or previously fractured in a fracturing operation) or unfractured. The stimulation operation can be performed in a new wellbore or an existing wellbore. In some operations, the fluid can be injected to alter the wettability of existing fractures within the formation (without further fracturing the formation significantly by either forming new fractures within the formation and / or extending the existing fractures within the formation). In such stimulation operations, no proppant is used, and fluid injection generally occurs at a lower pressure. In some embodiments, the aqueous fluid is substantially free of proppant.

[0556] In some cases, the existing fractures can be naturally occurring fractures present within a formation. For example, in some embodiments, the formation can comprise naturally fractured carbonate or naturally fractured sandstone. The presence or absence of naturally occurring fractures within a subterranean formation can be assessed using standard methods known in the art, including seismic surveys, geology, outcrops, cores, logging, reservoir characterization including preparing grids, etc.

[0557] In some embodiments, methods for stimulating a subterranean formation with a fluid can comprise introducing an aqueous fluid (injection composition) as described herein through a wellbore into the subterranean formation; allowing the injection composition to imbibe into a rock matrix of the subterranean formation for a period of time; and producing fluids from the subterranean formation through the wellbore. The method can further include ceasing introduction of the aqueous fluid through the wellbore into the formation before the allowing step. In these methods, the same wellbore can be used for both introducing the injection composition and producing fluids from the subterranean formation, the same wellbore can be used. In some embodiments, introduction of the injection composition can increase the production of hydrocarbons from the same wellbore, from a different wellbore in fluid communication with the subterranean formation, or any combination thereof.

[0558] In some embodiments, the fluids can include a hydrocarbon. In some embodiments, injection of the aqueous fluid into the formation results in increased hydrocarbon recovery from the wellbore as compared to an expected level of hydrocarbon recovery projected from a decline curve fit to production history of the wellbore. In some embodiments, the decline curve is fit to production history of the existing wellbore using Arp’s Equation.

[0559] In some embodiments, the stimulation operation can further comprise preparing the injection composition. For example, in some embodiments, the stimulation operation can further comprise combining the compounds, surfactant mixtures, or any combination described herein with optionally one or more additional components to form an injection composition. In some embodiments, introducing an injection composition as described herein through a wellbore into the subterranean formation can comprise injecting the injection composition through the wellbore and into the subterranean formation at a sufficient pressure and at a sufficient rate to stimulate hydrocarbon production from naturally occurring fractures in the subterranean formation.

[0560] The injection composition as described herein can be allowed to contact the rock matrix (e.g., to imbibe into the rock matrix) of the subterranean formation for varying periods of time depending on the nature of the rock matrix. The imbibing can occur during the introducing step, between the introducing and producing step, or any combination thereof. In some examples, the injection composition can be allowed to imbibe into the rock matrix of the subterranean formation for at least one day (e.g., at least two days, at least three days, at least four days, at least five days, at least six days, at least one week, at least two weeks, at least three weeks, at least one month, at least two months, at least three months, at least four months, or at least five months). In some examples, the injection composition can be allowed to imbibe into the rock matrix of the subterranean formation for six months or less (e.g., five months or less, four months or less, three months or less, two months or less, one month or less, three weeks or less, two weeks or less, one week or less, six days or less, five days or less, four days or less, three days or less, or two days or less).

[0561] In some embodiments, the wellbore used in the stimulation operation may have a substantially vertical portion only, or a substantially vertical portion and a substantially horizontal portion below the substantially vertical portion.

[0562] In some embodiments, the stimulation methods described herein can comprise stimulating a naturally fractured region of the subterranean formation proximate to a new wellbore (e.g., an infill well). In some embodiments, the stimulation methods described herein can comprise stimulating a naturally fractured region of the subterranean formation proximate to an existing wellbore.

[0563] In some embodiments, the stimulation methods described herein can comprise stimulating a previously fractured or previously refractured region of the subterranean formation proximate to a new wellbore (e.g., an infill well). In some embodiments, the stimulation methods described herein can comprise stimulating a previously fractured or previously refractured region of the subterranean formation proximate to an existing wellbore. The previous refracturing operation may include hydraulic fracturing, fracturing using electrodes such as described in U.S. Patent No. 9,890,627 (Attorney Dkt. No. T-9622A), U.S. Patent No. 9,840,898 (Attorney Dkt. No. T-9622B), U.S. Patent Publication No. 2018 / 0202273 (Attorney Dkt. No. T-9622A-CIP), or refracturing with any other available equipment or methodology. In some embodiments, after a formation that has fractures, such as naturally occurring factures, fractures from a fracture operation, fractures from a refracturing operation, or any combination thereof, the fractured formation may be stimulated. For example, a formation may be stimulated after a sufficient amount of time has passed since the fracturing operation with electrodes or refracturing operation with electrodes occurred in that formation so that the electrical pulses utilized to fracture or refracture that formation do not substantially affect the injection composition.

[0564] In some embodiments, the stimulation operation can further comprise adding a tracer to the injection composition prior to introducing the injection fluid through the wellbore into the subterranean formation; recovering the tracer from the fluids produced from the subterranean formation through the wellbore, fluids recovered from a different wellbore in fluid communication with the subterranean formation, or any combination thereof; and comparing the quantity of tracer recovered from the fluids produced to the quantity of tracer introduced to the injection composition. The tracer can be any suitable tracer, such as a water tracer or an oil tracer.

[0565] In some embodiments, the subterranean formation can have a permeability of from 26 millidarcy to 40,000 millidarcy. In some embodiments, the methods of treating the subterranean formation can comprise an EOR operation. For example, the wellbore can comprise an injection wellbore, and the method can comprise a method for hydrocarbon recovery that comprises (a) injecting the aqueous fluid through the injection wellbore into the subterranean formation; and (b) producing fluids from a production wellbore spaced apart from the injection wellbore a predetermined distance and in fluid communication with the subterranean formation. The injection of the aqueous fluid can increase the flow of hydrocarbons to the production well.

[0566] Also provided are methods of displacing a hydrocarbon material in contact with a solid material. These methods can include contacting a hydrocarbon material with a compound, surfactant mixture, composition (injection composition), or any combination thereof described herein, wherein the hydrocarbon material is in contact with a solid material. The hydrocarbon material is allowed to separate from the solid material thereby displacing the hydrocarbon material in contact with the solid material. In some embodiments, the surfactant composition can comprise a borate-acid buffer.

[0567] In other embodiments, the hydrocarbon material is unrefined petroleum (e.g., in a petroleum reservoir). In some further embodiments, the unrefined petroleum is a heavy oil. A "heavy oil" as provided herein is an unrefined petroleum with an API gravity less than 20. In some embodiments, the API gravity of the unrefined petroleum is less than 15. In some embodiments, the API gravity of the unrefined petroleum is less than 10. In other embodiments, the API gravity of the unrefined petroleum is less than 5. In some embodiments, the API gravity of the unrefined petroleum is less than I. In some other embodiments, the API gravity of the unrefined petroleum is between 1 and 45.

[0568] In other embodiments, the hydrocarbons or unrefined petroleum can comprise crude having an H2S concentration of at least 0.5%, a CO2 concentration of 0.3%, or any combination thereof.

[0569] In some embodiments, the hydrocarbons or unrefined petroleum can comprise crude having an H2S concentration of at least 0.5% (e.g., at least 1%, at least 1.5%, at least 2%, at least 2.5%, at least 3%, at least 3.5%, at least 4%, or at least 4.5%). In some embodiments, the hydrocarbons or unrefined petroleum can comprise crude having an H2S concentration of 5% or less (4.5% or less, 4% or less, 3.5% or less, 3% or less, 2.5% or less, 2% or less, 1.5% or less, or 1% or less).

[0570] The hydrocarbons or unrefined petroleum can comprise crude having an H2S concentration ranging from any of the minimum values described above. For example, in some embodiments, the hydrocarbons or unrefined petroleum can comprise crude having an H2S concentration of from 0.5% to 5% (e.g., from 0.5% to 2.5%).

[0571] In some embodiments, the hydrocarbons or unrefined petroleum can comprise crude having a CO2 concentration of at least 0.3% (e.g., at least 0.5%, at least 1%, at least 1.5%, at least 2%, at least 2.5%, at least 3%, at least 3.5%, at least 4%, or at least 4.5%). In some embodiments, the hydrocarbons or unrefined petroleum can comprise crude having a CO2 concentration of 5% or less (4.5% or less, 4% or less, 3.5% or less, 3% or less, 2.5% or less, 2% or less, 1.5% or less, 1% or less, or 0.5% or less).

[0572] The hydrocarbons or unrefined petroleum can comprise crude having a CO2 concentration ranging from any of the minimum values described above. For example, in some embodiments, the hydrocarbons or unrefined petroleum can comprise crude having a CO2 concentration of from 0.3% to 5% (e.g., from 0.3% to 2.5%).

[0573] The solid material may be a natural solid material (i.e., a solid found in nature such as rock). The natural solid material may be found in a petroleum reservoir. In some embodiments, the method is an enhanced oil recovery method. Enhanced oil recovery methods are well known in the art. A general treatise on enhanced oil recovery methods is Basic Concepts in Enhanced Oil Recovery Processes edited by M. Baviere (published for SCI by Elsevier Applied Science, London and New York, 1991). For example, in an enhanced oil recovery method, the displacing of the unrefined petroleum in contact with the solid material is accomplished by contacting the unrefined with a surfactant composition provided herein, wherein the unrefined petroleum is in contact with the solid material. The unrefined petroleum may be in an oil reservoir. The composition can be pumped into the reservoir in accordance with known enhanced oil recovery parameters. Upon contacting the unrefined petroleum, the aqueous composition can form an emulsion composition with the unrefined petroleum.

[0574] In some embodiments, the natural solid material can be rock or regolith. The natural solid material can be a geological formation such as clastics or carbonates. The natural solid material can be either consolidated or unconsolidated material or mixtures thereof. The hydrocarbon material may be trapped or confined by "bedrock" above or below the natural solid material. The hydrocarbon material may be found in fractured bedrock or porous natural solid material. In other embodiments, the regolith is soil. In other embodiments, the solid material can be, for example, oil sand or tar sands.

[0575] In other embodiments, the solid material can comprise equipment associated with an oil and gas operation. For example, the solid material can comprise surface processing equipment, downhole equipment, pipelines and associated equipment, pumps, and other equipment which contacts hydrocarbons during the course of an oil and gas operation.

[0576] In some embodiments, a hydrocarbon in the formation can have an asphaltene concentration of at least 0.5% (e.g., 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10%, 1 1%, 12%, 13%, 14%, 15%, or 16%).

[0577] In some embodiments, a hydrocarbon in the formation can have an asphaltene concentration of 17% or less (e.g., 16% or less, 15% or less, 14% or less, 13% or less, 12% or less, 11% or less, 10% or less, 9% or less, 8% or less, 7% or less, 6% or less, 5% or less, 4% or less, 3% or less, 2% or less, or 1 % or less). A hydrocarbon in the formation can have an asphaltene concentration ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, a hydrocarbon in the formation can have an asphaltene concentration of from 0.5% to 17% (e.g., from 0.5% to 1%, from 0.5% to 2%, from 0.5% to 3%, from 0.5% to 4%, from 0.5% to 5%, from 0.5% to 6%, from 0.5% to 7%, from 0.5% to 8%, from 0.5% to 9%, from 0.5% to 10%, from 0.5% to 11%, from 0.5% to 12%, from 0.5% to 13%, from 0.5% to 14%, from 0.5% to 15%, from 0.5% to 16%, from 1% to 2%, from 1% to 3%, from 1% to 4%, from 1% to 5%, from 1% to 6%, from 1% to 7%, from 1% to 8%, from 1% to 9%, from 1% to 10%, from 1% to 11%, from 1% to 12%, from 1% to 13%, from 1% to 14%, from 1% to 15%, from 1% to 16%, from 1% to 17%, from 2% to 3%, from 2% to 4%, from 2% to 5%, from 2% to 6%, from 2% to 7%, from 2% to 8%, from 2% to 9%, from 2% to 10%, from 2% to 11%, from 2% to 12%, from 2% to 13%, from 2% to 14%, from 2% to 15%, from 2% to 16%, from 2% to 17%, from 3% to 4%, from 3% to 5%, from 3% to 6%, from 3% to 7%, from 3% to 8%, from 3% to 9%, from 3% to 10%, from 3% to 11%, from 3% to 12%, from 3% to 13%, from 3% to 14%, from 3% to 15%, from 3% to 16%, from 3% to 17%, from 4% to 5%, from 4% to 6%, from 4% to 7%, from 4% to 8%, from 4% to 9%, from 4% to 10%, from 4% to 11%, from 4% to 12%, from 4% to 13%, from 4% to 14%, from 4% to 15%, from 4% to 16%, from 4% to 17%, from 5% to 6%, from 5% to 7%, from 5% to 8%, from 5% to 9%, from 5% to 10%, from 5% to 11%, from 5% to 12%, from 5% to 13%, from 5% to 14%, from 5% to 15%, from 5% to 16%, from 5% to 17%, from 6% to 7%, from 6% to 8%, from 6% to 9%, from 6% to 10%, from 6% to 11%, from 6% to 12%, from 6% to 13%, from 6% to 14%, from 6% to 15%, from 6% to 16%, from 6% to 17%, from 7% to 8%, from 7% to 9%, from 7% to 10%, from 7% to 11%, from 7% to 12%, from 7% to 13%, from 7% to 14%, from 7% to 15%, from 7% to 16%, from 7% to 17%, from 8% to 9%, from 8% to 10%, from 8% to 11%, from 8% to 12%, from 8% to 13%, from 8% to 14%, from 8% to 15%, from 8% to 16%, from 8% to 17%, from 9% to 10%, from 9% to 11%, from 9% to 12%, from 9% to 13%, from 9% to 14%, from 9% to 15%, from 9% to 16%, from 9% to 17%, from 10% to 11%, from 10% to 12%, from 10% to 13%, from 10% to 14%, from 10% to 15%, from 10% to 16%, from 10% to 17%, from 11% to 12%, from 11% to 13%, from

[0578] 11% to 14%, from 11% to 15%, from 11% to 16%, from 11% to 17%, from 12% to 13%, from

[0579] 12% to 14%, from 12% to 15%, from 12% to 16%, from 12% to 17%, from 13% to 14%, from

[0580] 13% to 15%, from 13% to 16%, from 13% to 17%, from 14% to 15%, from 14% to 16%, from

[0581] 14% to 17%, from 15% to 16%, from 15% to 17%, or from 16% to 17%). In some embodiments, the formation can have a temperature of at least 75 °F (e.g., at least 80 °F, at least 85 °F, at least 90 °F, at least 95 °F, at least 100 °, at least 105 °F, at least 110 °F, at least 115 °F, at least 120 °F, at least 125 °F, at least 130 °F, at least 135 °F, at least 140 °F, at least 145 °F, at least 150 °F, at least 155 °F, at least 160 °F, at least 165 °F, at least 170 °F, at least 175 °F, at least 180 °F, at least 190 °F, at least 200 °F, at least 205 °F, at least 210 °F, at least 215 °F, at least 220 °F, at least 225 °F, at least 230 °F, at least 235 °F, at least 240 °F, at least 245 °F, at least 250 °F, at least 255 °F, at least 260 °F, at least 265 °F, at least 270 °F, at least 275 °F, at least 280 °F, at least 285 °F, at least 290 °F, at least 295 °F, at least 300 °F, at least 305 °F, at least 310 °F, at least 315 °F, at least 320 °F, at least 325 °F, at least 330 °F, at least 335 °F, at least 340 °F, or at least 345 °F). In some embodiments, the formation can have a temperature of 350 °F or less (e.g., 345 °F or less, 340 °F or less, 335 °F or less, 330 °F or less, 325 °F or less, 320 °F or less, 315 °F or less, 310 °F or less, 305 °F or less, 300 °F or less, 295 °F or less, 290 °F or less, 285 °F or less, 280 °F or less, 275 °F or less, 270 °F or less, 265 °F or less, 260 °F or less, 255 °F or less, 250 °F or less, 245 °F or less, 240 °F or less, 235 °F or less, 230 °F or less, 225 °F or less, 220 °F or less, 215 °F or less, 210 °F or less, 205 °F or less, 200 °F or less, 195 °F or less, 190 °F or less, 185 °F or less, 180 °F or less, 175 °F or less, 170 °F or less, 165 °F or less, 160 °F or less, 155 °F or less, 150 °F or less, 145 °F or less, 140 °F or less, 135 °F or less, 130 °F or less, 125 °F or less, 120 °F or less, 115 °F or less, 110 °F or less, 105 °F or less, 100 °F or less, 95 °F or less, 90 °F or less, 85 °F or less, or 80 °F or less).

[0582] The formation can have a temperature ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the formation can have a temperature of from 75 °F to 350 °F (approximately 24 °C to 176 °C), from 150 °F to 250 °F (approximately 66 °C to 121 °C), from 1 10 °F to 350 °F (approximately 43 °C to 176 °C), from 110 °F to 150 °F (approximately 43 °C to 66 °C), from 150 °F to 200 °F (approximately 66 °C to 93 °C), from 200 °F to 250 °F (approximately 93 °C to 121 °C), from 250 °F to 300 °F (approximately 121 °C to 149 °C), from 300 °F to 350 °F (approximately 149 °C to 176 °C), from 110 °F to 240 °F (approximately 43 °C to 1 16 °C), or from 240 °F to 350 °F (approximately 116 °C to 176 °C).

[0583] In some embodiments, the salinity of formation can be at least 5,000 ppm TDS (e.g., at least 25,000 ppm TDS, at least 50,000 ppm TDS, at least 75,000 ppm TDS, at least 100,000 ppm TDS, at least 125,000 ppm TDS, at least 150,000 ppm TDS, at least 175,000 ppm TDS, at least 200,000 ppm TDS, at least 225,000 ppm TDS, at least 250,000 ppm TDS, or at least 275,000 ppm TDS). In some embodiments, the salinity of formation can be 300,000 ppm TDS or less (e.g., 275,000 ppm TDS or less, 250,000 ppm TDS or less, 225,000 ppm TDS or less, 200,000 ppm TDS or less, 175,000 ppm TDS or less, 150,000 ppm TDS or less, 125,000 ppm TDS or less, 100,000 ppm TDS or less, 75,000 ppm TDS or less, 50,000 ppm TDS or less, or 25,000 ppm TDS or less).

[0584] The salinity of formation can range from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the salinity of formation can be from 5,000 ppm TDS to 300,000 ppm TDS (e.g., from 100,000 ppm to 300,000 ppm TDS).

[0585] In some embodiments, the formation can be oil-wet. In some embodiments, the formation can be water- wet. In some embodiments, the formation can be mixed-wet. In some embodiments, the formation can be intermediate-wet.

[0586] In some embodiments, the composition described herein can be introduced at a wellhead pressure of at least 0 PSI (e.g., at least 1,000 PSI, at least 2,000 PSI, at least 3,000 PSI, at least 4,000 PSI, at least 5,000 PSI, at least 6,000 PSI, at least 7,000 PSI, at least 8,000 PSI, at least 9,000 PSI, at least 10,000 PSI, at least 15,000 PSI, at least 20,000 PSI, or at least 25,000 PSI). In some embodiments, the composition can be introduced at a wellhead pressure of 30,000 PSI or less (e.g., 25,000 PSI or less, 20,000 PSI or less, 15,000 PSI or less, 10,000 PSI or less, 9,000 PSI or less, 8,000 PSI or less, 7,000 PSI or less, 6,000 PSI or less, 5,000 PSI or less, 4,000 PSI or less, 3,000 PSI or less, 2,000 PSI or less, or 1,000 PSI or less).

[0587] The composition described herein can be introduced at a wellhead pressure ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the injection composition can be introduced at a wellhead pressure of from 0 PSI to 30,000 PSI (e.g., from 6,000 PSI to 30,000 PSI, or from 5,000 PSI to 10,000 PSI. In some embodiments, the injection composition can be used in a reservoir stimulation operation, and the injection composition can be introduced at a wellhead pressure of from 0 PSI to 1,000 PSI.

[0588] In some embodiments, there is no need to drill the wellbore. In some embodiments, the wellbore has been drilled and completed, and hydrocarbon production has occurred from the wellbore. In other embodiments, methods described herein can optionally include one or more of drilling the wellbore, completing the wellbore, and producing hydrocarbons from the wellbore (prior to injection of the surfactant composition). A number of embodiments of the disclosure have been described. Nevertheless, it will be understood that various modifications may be made without departing from the spirit and scope of the invention. Accordingly, other embodiments are within the scope of the following claims.

[0589] All of the compositions and methods disclosed and claimed herein can be made and executed without undue experimentation in light of the present disclosure. While the compositions and methods of this disclosure have been described in terms of preferred embodiments, it will be apparent to those of skill in the art that variations may be applied to the compositions and methods and in the steps or in the sequence of steps of the methods described herein without departing from the concept, spirit and scope of the disclosure. More specifically, it will be apparent that certain agents which are both chemically related may be substituted for the agents described herein while the same or similar results would be achieved. All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosure as defined by the appended claims.

[0590] By way of non-limiting illustration, examples of certain embodiments of the present disclosure are given below.

[0591] EXAMPLES

[0592] Example 1: TSP-Based Poly Sulfonate Surfactants

[0593] Synthesis of Tristyrenated phenol (TSP) sulfonates

[0594] 15 g of TSP was added to a dry round bottomed flask and 5 ml of CHCh were added. Subsequently, nitrogen was flushed through the system for 72 hours while mixing. Then, the solution was heated to 75 °C and 6.9 ml of concentrated H2SO4 were added slowly. Solution was mixed thoroughly for 5 hours. A synthetic scheme is shown in Figure 4.

[0595] TSP was also reacted using different molar ratio of sulfonated regent. TSP:sulfonated regent (H2SO4) 1:1, 1 :3 and 1 :5.13C NMR, ’H NMR and HPLC were performed. Results for13C NMR,]H NMR and HPLC are shown in Figures 3, and 5-15.

[0596] Two phase Hyamine anionic surfactant titration using bromocresol Green and chloroform was also performed to determine ratio of TSP:sulfonate / sulfate ratio in reaction mixture. Results are shown in Table 3.

[0597] Table 3.

[0598] Synthesis of Tristyryl phenol 16EO sulfonates

[0599] 15 g of TSP was added to the dry round bottomed flask. Subsequently, N2 was flushed through the system for 72 hours while mixing. Then, the solution was heated to 75 °C and 2.5 ml of concentrated H2SO4 was added slowly. Solution was mixed thoroughly 20 hours. A synthetic scheme is shown in Figure 12.

[0600] TSP-16EO was reacted with sulfonated regent (H2SO4) at a ratio of 1:6.13C NMR, 'H NMR, and HPLC were perfomed. Results for13C NMR,1H NMR, and HPLC are shown in Figures 13-15.

[0601] Two phase Hyamine anionic surfactant titration using bromocresol Green and chloroform was performed to determine ratio of TSP:sulfonate / sulfate ratio in reaction mixture. Results are shown below.

[0602] Aqueous stability and Phase behavior: Basic formulation: 0.45% IOS, 0.5% nonionic, 1.4% co-solvent. Salinity was fixed to approximately sea water salinity (42,670 TDS) and 55 °C temperature. Phase behavior and aqueous stability tests were performed by adding 0-0.5% TSP- Polysulfonate and TSP-16EO-Poly-Sulfonate to the basic formulation.

[0603] Results for aqueous stability and phase behavior are summarized below in Tables 1 and 2 and Figure 1.

[0604] Table 1. Aqueous stability and phase behavior for TSP-polysufonate.

[0605] Table 2. Aqueous stability and phase behavior for TSP-16EO-polySO3. Core flood experiments were performed using the formulation below in sea water.

[0606] Control: 0.45% ISO, 0.50% nonionic, and 1.40% EGBE. TSP formulation: 0.45% ISO, 0.50% nonionic, 0.30% TSP-poly sulfonate, and 1.40% EGBE. Results are shown in Figure 2.

[0607] Synthesis of 3 types of Tristyrenated phenol (TSP) based polysulfonates

[0608] Starting material (TSP, TSP-16EO, or TSP-35PO-30EO) was added to a dry round bottomed flask and CHCh were added. Subsequently, nitrogen was flushed through the system for 72 hours while mixing. Then, the solution was heated to 75 °C and concentrated H2SO4 were added slowly. Solution was mixed thoroughly for 3 hours.

[0609] The starting materials were reacted using different molar ratio of sulfonated reagent (H2SO4) such as from 1 :6 to 1 :99. Figure 18 shows the HPLC results for the synthesis of TSP- 35PO-30EO-Polysulfonate at a molar ratio of 1 :96 of TSP-35PO-30EO:sulfonated reagent. Two phase Hyamine anionic surfactant titration using bromocresol Green and chloroform was also performed to determine ratio of the starting material to sulfonate / sulfate ratio in reaction mixture. Results are shown below.

[0610] Aqueous stability: aqueous stability tests were performed by comparing adding 0.5% TSP to 0.5% TSP- polysulfonate in deionized water, TSP-16EO to TSP- 16EO-poly sulfonate in 11% NaCl solution at 76 °C, and TSP-35PO-30EO TSP-35PO-30EO-polysulfonate to 22% NaCl solution at 76 °C. Results for aqueous stability are shown Figures 19-21.

[0611] The compositions and methods of the appended claims are not limited in scope by the specific compositions and methods described herein, which are intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims. Various modifications of the compositions and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims. Further, while only certain representative compositions and method steps disclosed herein are specifically described, other combinations of the compositions and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited. Thus, a combination of steps, elements, components, or constituents may be explicitly mentioned herein; however, other combinations of steps, elements, components, and constituents are included, even though not explicitly stated.

Claims

WHAT IS CLAIMED IS:

1. A compound of Formula I or salt thereof:A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R16is alkene, C1-C32alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;BO represents -CH2-CH(ethyl)-O-;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; n, m, p, and q are each independently 0 to 6;the dotted line represents an optional double bond if valence permits; and at least two of R -R9, R12-R17or A are independently -SO3; wherein when:one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl.

2. The compound of claim 1, wherein3. The compound of any one of claims 1-2, wherein R1is -OH.

4. The compound of any one of claims 1-2, wherein R1is -OSO3.

5. The compound of any one of claims 1-2, wherein R1is -(PO)x-(EO)y-A.

6. The compound of any one of claims 1-5, wherein n, m, and q are 0.

7. The compound of any one of claims 1-6, wherein R6, R7, and R9are C1-C6alkyl.

8. The compound of any one of claims 1-7, wherein R10is H.The compound of claim 1, wherein10. The compound of claim 1 or claim 9, wherein n, m, and p are 1.

11. The compound of any one of claims 1, or 9-10, wherein12. The compound of any one of claims 1, or 9-10, wherein R1is13. The compound of any one of claims 1, or 9-12, wherein R11is H.

14. The compound of any one of claims 1, or 9-13, wherein R10is -(PO)x-(EO)y-A.

15. A compound of Formula II or salt thereof:wherein:R1is -OH,-OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;R2-R4are each independently H or -SO3;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R -R4, R16, R17, or A are independently -SO3.

16. A compound of Formula III or salt thereof:wherein:R2, R3, and R5are each independently H or -SO3;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R16is alkene, C1-C32alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2, R3, R5, R16, R17or A are independently -SO3.

17. A compound of Formula IV or salt thereof:Formula IV or Formula IVA wherein:R2, R3, and R5are each independently H or -SO3;R6-R8, and R12-R14are each independently H, -OH, -SO3, or C1-C6alkyl;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarhoxylate, or tricarboxylate;R16is alkene, C1-C32alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2, R3, R5-R8, R12-R14, R16-R17, or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl; one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6, alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

18. A compound of Formula V or salt thereof:Formula V wherein:R1is -OH, -OSO3, -(PO)x-(EO)y-A, -(BO)z-(PO)x-(EO)y-A, or -OR16;R2-R4are each independently H or -SO3;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R16is alkene, C1-C32alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R -R4, R16, R17, or A are independently -SO3.

19. A compound of Formula VI or salt thereof:Formula V I wherein:R1is -OH, -OSO3, (PO)x-(EO)y-A, (BO)z-(PO)x-(EO)y-A, or -OR16;R2-R4are each independently H or -SO3;R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R16is alkene, Ci -C32 alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R -R4, R6, R7, R9, R12, R13, R15-R17, or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

20. A compound of Formula VII or salt thereof:wherein:R2-R4are each independently H or -SO3;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R16is alkene, Ci -C32 alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R16, R17, or A are independently -SO3.

21. A compound of Formula VIII or salt thereof:wherein:R2-R4are each independently H or -SO3;R6, R7, R9, and R12, R13, R15are each independently H, -OH, -SO3, or C1-C6alkyl;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R16is alkene, C1-C32alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R2-R4, R6, R7, R9, R12, R13, R15-R17, or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R9or R1Sis -SO3. then one of R9or R15is H, -OH, or C1-C6alkyl; one of R9or R15is -OH, then one of R9or R15is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; and one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl.

22. The compound of any one of claims 16-21, wherein x is 0.

23. The compound of any one of claims 16-22, wherein y is 16.

24. The compound of any one of claims 1-23, wherein the compound is selected from:combination thereof.

25. A surfactant mixture comprising: a) a compound of Formula I or salt thereof:b) a compound of Formula II or salt thereof:c) a compound of Formula III or salt thereof or a compound of Formula IIIA or salt thereof:thereof; d) a compound of Formula IV or salt thereof or a compound of Formula IVA or salt thereof:combination thereof; e) a compound of Formula V or salt thereof:thereof; f) a compound of Formula VI or salt thereof:thereof; g) a compound of Formula VII or salt thereof or Formula VIIA or salt thereof:or any combination thereof; h) a compound of Formula VIII or salt thereof or Formula VIII or salt thereof:or any combination thereof; i) a compound of Formula IX or salt thereof, Formula IX A or salt thereof, Formula IXB or salt thereof, Formula IXC or salt thereof, Formula IXD or salt thereof:or any combination thereof; j) a compound of Formula X or salt thereof, Formula XA or salt thereof, Formula XB or salt thereof, Formula XC or salt thereof, or Formula XD or salt thereof:k) a compound of Formula XI or salt thereof, Formula XIA or salt thereof, Formula XIB or salt thereof, Formula XIC or salt thereof, or Formula XID or salt thereof:1) a compound of Formula XII or salt thereof, Formula XIIA or salt thereof, Formula XIIB or salt thereof, Formula XIIC or salt thereof, or Formula XIID or salt thereof:wherein:R1is -OH or -OSO3, -(PO)x-(EO)y-A, -(BO)z(PO)x-(EO)y-A, -OR16;R2-R5are each independently H or -SO3;R6-R9and R12-R15are each independently H, -OH, -SO3, or C1-C6alkyl;A is -OR16, -OH, -OSO3, -SO3, alkene, monocarboxylate, dicarboxylate, or tricarboxylate;R16is alkene, C1-C32alkyl,R17is H, C1-C32alkyl, alkenyl, aryl, -(PO)x-(EO)y-A, or -(BO)z(PO)x-(EO)y-A;EO represents -CH2-CH2-O-;PO represents -CH2-CH(methyl)-O-;BO represents -CH2-CH(ethyl)-O-; x is 0 to 65; y is 0 to 100; z is 0 to 10; and at least two of R -R9, R12-R17or A are independently -SO3; wherein when: one of R6or R12is -SO3, then one of R6or R12is H, -OH, or C1-C6alkyl; one of R6or R12is -OH, then one of R6or R12is H, -SO3or C1-C6alkyl; one of R8or R14is -SO3, then one of R8or R14is H, -OH, or C1-C6alkyl;one of R8or R14is -OH, then one of R8or R14is H, -SO3or C1-C6alkyl; one of R7or R13is -SO3, then one of R7or R13is H, -OH, or C1-C6alkyl; one of R7or R13is -OH, then one of R7or R13is H, -SO3or C1-C6alkyl; one of R9or R15is -SO3, then one of R9or R13is H, -OH, or C1-C6alkyl; and one of R9or R15is -OH, then one of R9or R13is H, -SO3or C1-C6alkyl; or any combination thereof.

26. A composition comprising water and a compound defined by any one of claims 1- 24.

27. The composition of claim 26, wherein the composition comprises a surfactant mixture defined by claim 25.

28. The composition of any one of claims 26-27, wherein the composition further comprises water, a co-surfactant, co-solvent, a friction reducer, a gelling agent, a crosslinker, a breaker, a pH adjusting agent, a non-emulsifier agent, an iron control agent, a corrosion inhibitor, a scale inhibitor, a biocide, a clay stabilizing agent, a chelating agent, a proppant, a wettability alteration chemical, or any combination thereof.

29. The composition of claim 28, wherein the one or more co-surfactants comprise an anionic surfactant.

30. The composition of claim 29, wherein the anionic surfactant comprises a sulfonate, a disulfonate, a sulfate, a disulfate, a sulfosuccinate, a disulfosuccinate, a carboxylate, a dicarboxylate, or any combination thereof.

31. The composition of claim 30, wherein the anionic surfactant comprises one of the following: a branched or unbranched C6-C32:PO(0-65):EO(0-100)- carboxylate;; a C15-C28 internal olefin sulfonate (IOS); a C8-C30 alkyl benzene sulfonate (ABS); a sulfosuccinate surfactant; a surfactant defined by the formula below:R1— R2— R3whereinR1comprises a branched or unbranched, saturated or unsaturated, cyclic or non- cyclic, hydrophobic carbon chain having 6-32 carbon atoms and an oxygen atom linking R1and R2;R2comprises an alkoxylated chain comprising at least one oxide group selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and any combination thereof; andR3comprises a branched or unbranched hydrocarbon chain comprising 2-12 carbon atoms and from 2 to 5 carboxylate groups; or a surfactant defined by the formula below:wherein:R4is, individually for each occurrence, a branched or unbranched, saturated or unsaturated, cyclic or non-cyclic, hydrophobic carbon chain having 6-32 carbon atoms; and M represents a counterion.

32. The composition of any one of claims 28-31, wherein the one or more co-surfactants comprise a non-ionic surfactant.

33. The composition of claim 32, wherein the non-ionic surfactant comprises a branched or unbranched C6-C32:PO(0-65):EO(0-100), such as a branched or unbranched C6- C30:PO(30-40):EO(25-35), a branched or unbranched C6-C12:PO(30-40):EO(25-35), or a branched or unbranched C6-C30:EO(8-30).

34. The composition of any one of claims 32-33, wherein the non-ionic surfactant has a hydrophilic-lipophilic balance of greater than 10.

35. The composition of any one of claims 28-34, wherein the one or more co-surfactants comprise a cationic surfactant.

36. The composition of any one of claims 28-35, wherein the one or more co-surfactants comprise a zwitterionic surfactant.

37. The composition of any one of claims 27-36, wherein the compound of Formula I has a concentration within the composition of from 0.05% to 5% by weight, based on the total weight of the composition.

38. The composition of any one of claims 28-37, wherein the one or more co-surfactants have a concentration within the composition of from 0.05% to 5% by weight, based on the total weight of the composition.

39. The composition of any one of claims 28-38, wherein the water comprises sea water, brackish water, flowback or produced water, wastewater (e.g., reclaimed or recycled), brine (e.g., reservoir or synthetic brine), fresh water (e.g., fresh water comprises < 1,000 ppm TDS water), or any combination thereof.

40. The composition of any one of claims 28-39, wherein the water comprises hard water or hard brine.

41. The composition of any one of claims 28-40, wherein the water comprises at least 10 ppm at least 100 ppm, at least 500 ppm, at least 1,000 ppm, at least 5,000 ppm, at least 10,000 ppm, at least 20,000 ppm, or at least 30,000 ppm of divalent metal ions chosen from Ca2+, Mg2+, Sr2*, and Ba2+, or any combination thereof.

42. The composition of any one of claims 28-41, wherein the water comprises from 100 ppm to 30,000 ppm of divalent metal ions chosen from Ca2+, Mg2+, Sr2+, and Ba2+, or any combination thereof.

43. The composition of any of claims 27-42, further comprises an unreacted starting material for synthesis, a byproduct remaining from synthesis, or any combination thereof.

44. A method of preventing asphaltene aggregation in a subterranean formation comprising:contacting a hydrocarbon containing asphaltene with a compound of any one of claims 1-24, a surfactant mixture of claim 25, a composition of any one of claims 26-43, a styryl phenol sulfonate compound, or any combination thereof.

45. A method for treating a subterranean formation, the method comprising: introducing an aqueous fluid comprising water and a compound of any one of claims1-24, a surfactant mixture of claim 25, a composition of any one of claims 26-43, or any combination thereof through a wellbore into the formation.

46. The method of claim 45, wherein the subterranean formation comprises an unconventional subterranean formation.

47. The method of claim 45, wherein the subterranean formation comprises a conventional subterranean formation.

48. The method of any of claims 45-47, wherein the method comprises a method for stimulating the subterranean formation that comprises:(a) injecting the aqueous fluid through the wellbore into the subterranean formation;(b) allowing the aqueous fluid to imbibe into a rock matrix of the subterranean formation for a period of time; and(c) producing fluids from the subterranean formation through the wellbore.

49. The method of claim 48, further comprising ceasing introduction of the aqueous fluid through the wellbore into the subterranean formation before allowing step (b).

50. The method of any one of claims 48-49, wherein the period of time is from one day to six months, such as from two weeks to one month.

51. The method of any one of claims 45-50, wherein the injection of the aqueous fluid releases hydrocarbons from pores in a rock matrix in a region of the subterranean formation proximate to the wellbore.

52. The method of any one of claims 45-51, wherein the fluids comprise a hydrocarbon.

53. The method of claim 52, wherein injection of the aqueous fluid into the subterranean formation results in increased hydrocarbon recovery from the wellbore as compared to an expected level of hydrocarbon recovery projected from a decline curve fit to production history of the wellbore.

54. The method of claim 53, wherein the decline curve is fit to production history of the existing wellbore using Arp’s Equation.

55. The method of any one of claims 45-54, wherein the aqueous fluid is substantially free of proppant.

56. The method of any of claims 45-55, wherein the method comprises a method for fracturing the subterranean formation that comprises:(a) injecting the aqueous fluid into the subterranean formation through the wellbore at a sufficient pressure to create or extend at least one fracture in a rock matrix of the formation in fluid communication with the wellbore.

57. The method of claim 56, wherein the aqueous fluid further comprises a proppant.

58. The method of any one of claims 56-57, wherein the method further comprises producing fluids from the subterranean formation through the wellbore.

59. The method of claim 58, wherein the wellbore comprises an injection wellbore, and wherein the method comprises a method for hydrocarbon recovery that comprises:(a) injecting the aqueous fluid through the injection wellbore into the subterranean formation; and(b) producing fluids from a production wellbore spaced apart from the injection wellbore a predetermined distance and in fluid communication with the subterranean formation; wherein injection of the aqueous fluid increases a flow of hydrocarbons to the production wellbore.

60. The method of claim 45, wherein the method comprises an enhanced oil recovery (EOR) operation.

61. The method of claim 60, wherein the EOR operation includes a surfactant flooding operation, an AS flooding operation, a SP flooding operation, an ASP flooding operation, or any combination thereof.

62. The method of claim 45, wherein the method comprises a wellbore cleanup operation.

63. The method of claim 45, wherein the method comprises a stimulation operation.

64. The method of any one of claims 44-63, wherein a hydrocarbon in the formation comprises an asphaltene concentration of from 0.5% to 17%, such as from 1% to 15%, from 3% to 15%, from 5% to 15%, or from 7% to 15%.

65. The method of any one of claims 45-64, wherein the subterranean formation has a salinity of from 5,000 ppm TDS to 300,000 ppm TDS.

66. The method of any one of claims 45-65, wherein the subterranean formation has a temperature of from 75 °F to 350 °F.

67. A method for treating a formation, the method comprising: introducing an aqueous fluid comprising water and a compound of any one of claims 1-24, a surfactant mixture of claim 25, a composition of any one of claims 26-43, a styryl phenol sulfonate compound, or any combination thereof through a wellbore into the formation, wherein a hydrocarbon in the formation comprises an asphaltene concentration of from 1% to 15%, such as from 3% to 15%, from 5% to 15%, or from 7% to 15%.

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