Methods for preparing alkyl alkoxy sulfates and methods of assessing injection fluids

Abstract

Described herein are methods of measuring an alkoxy anionic compound cloud point, method of preparing an alkoxy anionic compound and a method of monitoring a reaction progress for preparing an alkoxy anionic compound.

Description

[0001] METHODS FOR PREPARING ALKYL ALKOXY SULFATES

[0002] AND METHODS OF ASSESSING INJECTION FLUIDS

[0003] CROSS-REFERENCE TO RELATED APPLICATIONS

[0004] This application claims benefit of priority of U.S. Provisional Application No. 63 / 579,193, filed August 28, 2023, which is incorporated herein by reference in its entirety.

[0005] BACKGROUND

[0006] A standard percent activity titration is generally used to determine the progression of a reaction producing an alkoxy anionic compound. However, over-cooking a batch with an acidic agent such as sulfamic acid leads to cleavage, for example at propylene oxide subunits, to produce undesirable by-products. Standard percent activity titration gives exaggerated values because the byproducts also get sulfated, carboxymethylated, or sulfonated and respond to the titration. Currently, there is no satisfactory method to qualify an alkoxy anionic product at the right sulfation, sulfonation, or carboxylation degree.

[0007] Accordingly, improved methods to track the reaction progress (e.g., to determine when to terminate a reaction) and / or quantify product purity are needed.

[0008] SUMMARY

[0009] Provided herein are methods of measuring an alkoxy anionic compound cloud point, the method including: (i) contacting the alkoxy anionic compound with an inorganic salt solution to form a test sample; and (ii) increasing the test sample temperature from 1 to 90°C until the cloud point of the test sample including the alkoxy anionic compound is reached.

[0010] Also described herein are methods of monitoring reaction progress, the method including: (i) determining a cloud point for a reaction product including an alkoxy anionic compound using the method described herein; (ii) providing a reaction sample including the alkoxy anionic compound; (iii) contacting the reaction sample with an inorganic salt solution to form a test sample; (iv) increasing the test sample temperature from 1 to 90°C until a cloud point for the test sample is reached; (v) comparing the reaction product cloud point to the test sample cloud point; and (vi) repeating steps (ii) to (v) until the cloud point of the test sample is equal to the cloud point of the reaction product. Also described herein are methods of preparing an alkoxy anionic compound, the methods including: (i) reacting an alcohol alkoxylate with a sulfonating agent, carboxy lating agent, carboxymethylating agent, or sulfating agent to generate a reaction product including an alkoxy anionic compound; (ii) monitoring the reaction progress using the method described herein; and (iii) quenching the reaction when the cloud point of the test sample is equal to the cloud point of the reaction product. In some embodiments, the method further includes (iv) isolating the reaction product.

[0011] In some embodiments, the alkoxy anionic compound can be defined by Formula I below: R1-O-(BO)x-(PO)y-(EO)z-Q

[0012] Formula I wherein,

[0013] BO represents -CH2-CH(ethyl)-O-;

[0014] PO represents -CH2-CH(methyl)-O-;

[0015] EO represents -CH2-CH2-O-;

[0016] R1represents a hydrogen, a C1-C32 alkyl group, a C1-C32 alkenyl group, a C1-C32 alkynyl group, a cycloalkyl group, an aryl group, or an alkylaryl group;

[0017] Q represents sulfate, carboxylate, or carboxymethyl; x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100, wherein when R1represents hydrogen, then y is from 10 to 75.

[0018] 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.

[0019] DETAILED DESCRIPTION

[0020] 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.

[0021] Definitions

[0022] 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. Publications cited herein and the materials for which they are cited are specifically incorporated by reference.

[0023] General Definitions

[0024] 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 valuations 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.

[0025] 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.

[0026] Ranges can be expressed herein as from “about” one particular value, and / or to “about” another particular value. By “about” is meant within 5% of the value, e.g., within 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.

[0027] 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.

[0028] 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).

[0029] A “control” is an alternative subject or sample used in an experiment for comparison purposes. A control can be "positive" or "negative."

[0030] The term "contacting" as used herein, refers to materials or compounds being sufficiently close in proximity to react or interact.

[0031] 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, conformance control operations, as well as combinations thereof such as alkaline-polymer flooding or alkaline-surfactant-polymer flooding), microbial injection, and thermal recovery (which includes, for example, cyclic steam, and steam 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, a conformance control operation, or any combination thereof. The terms “operation” and “application” may be used interchangeability herein, as in EOR operations or EOR applications. The term “hydrocarbon” refers to a compound containing only carbon and hydrogen atoms.

[0032] “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). “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).

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] “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.

[0040] 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.

[0041] 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), Huid(s), fracturing fluid component(s), proppants, and other equipment and non-equipment items related to preparing the fracturing fluid and injecting the fracturing fluid.

[0042] 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.

[0043] Chemical Definitions

[0044] 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.

[0045] 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. 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.

[0046] 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.

[0047] “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.

[0048] 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, Ci-Ce, 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 -methyl-pentyl, 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., - SSC Ra), 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.

[0049] 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.

[0050] 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.

[0051] 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, l-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-l -propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl- 1 -propenyl, l-ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,

[0052] 1 -methyl- 1 -pentenyl, 2-methyl- 1 -pentenyl, 3-methyl-l -pentenyl, 4-methyl-l -pentenyl, 1-methyl-

[0053] 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,

[0054] 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 , 1 -dimethyl-2-butenyl, 1,1- dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1 ,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl,

[0055] 1.3-dimethyl- 1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl,

[0056] 2.3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3, 3-dimethyl-l -butenyl,

[0057] 3.3-dimethyl-2-butenyl, 1 -ethyl- 1 -butenyl, l-ethyl-2-butenyl, 1-ethy 1-3 -butenyl, 2-ethyl-l- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, l,l,2-triniethyl-2-propenyl, 1 -ethyl- l-methyl-2- propenyl, l-ethyl-2- methyl- 1 -propenyl, and l-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- CPUCH-CJU; 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 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., -SSCERa), or thiol, as described below, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied.

[0058] 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-C18, C2-C16, C2-G4, C2-C 12, 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,

[0059] 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, 1 -methyl-2-butynyl, 1 -methyl -

[0060] 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-l -pentynyl, 4-methyl-l -pentynyl, 1-methyl-

[0061] 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, l,l-dimethyl-3- butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-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., -SSCERa), or thiol, as described below.

[0062] 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.

[0063] 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.

[0064] 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, or thiol as described herein.

[0065] The term “cyclic group” is used herein to refer to either aryl groups, non-aryl groups ( / .<?., 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.

[0066] 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 fivemembered 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- triazolyl, 1,3,4-thiadiazolyl, and 1,3,4-oxadiazolyl. A six-membered 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 six-membered ring heteroaryls are pyridyl, pyrazinyl, pyrimidinyl, triazinyl and pyridazinyl.

[0067] 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, tetrahydrothienyl, 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 ring-forming 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 ( / .<?., 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.

[0068] 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.

[0069] The term “acyl” as used herein is represented by the formula -CiOjZ1where 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.

[0070] 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 Ci-C24(e.g., C1-C22, C1-C20, Ci-Cis, C1-C16, C1-C14, C1-C12, C1-C10, Ci-C8, Ci-C6, 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, 2,2- dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy, 1-ethyl-butoxy, 2-ethylbutoxy, 1,1,2-trimethyl-propoxy, 1,2,2-trimethyl-propoxy, 1 -ethyl- 1-methyl-propoxy, and l-ethyl-2- methyl-propoxy.

[0071] The term “aldehyde” as used herein is represented by the formula — C(O)H.

[0072] 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.

[0073] 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".

[0074] The term “ester” as used herein is represented by the formula — OC(O)Z' or — OIOZ1, where Z1can be an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.

[0075] 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.

[0076] 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.

[0077] The term “halide” or “halogen” or “halo” as used herein refers to fluorine, chlorine, bromine, and iodine.

[0078] The term “hydroxyl” as used herein is represented by the formula — OH.

[0079] The term “nitro” as used herein is represented by the formula — NO2.

[0080] The term “silyl” as used herein is represented by the formula — SiZ'Z2Z\ where Z1, Z2, and Z3can be, independently, hydrogen, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.

[0081] 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.

[0082] The term “sulfonylamino” or “sulfonamide” as used herein is represented by the formula — S(O)2NH— .

[0083] The term “thiol” as used herein is represented by the formula — SH.

[0084] The term “thio” as used herein is represented by the formula — S — . As used herein, Me refers to a methyl group; OMe refers to a methoxy group; and z-Pr refers to an isopropyl group.

[0085] “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.

[0086] 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, - NRaSChRb, -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, heteroarylalkyl.

[0087] 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).

[0088] 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.

[0089] Alkoxy anionic compounds

[0090] The alkoxy anionic compound described herein can be defined by Formula I below:

[0091] R]-O-(BO)x-(PO)y-(EO)z-Q

[0092] Formula I wherein,

[0093] BO represents -CH2-CH(ethyl)-O-;

[0094] PO represents -CH2-CH(methyl)-O-;

[0095] EO represents -CH2-CH2-O-;

[0096] R1represents a hydrogen, a C1-C32 alkyl group, a C1-C32 alkenyl group, a C1-C32 alkynyl group, a cycloalkyl group, an aryl group, or an alkylaryl group;

[0097] Q represents sulfate, carboxylate, or carboxy methyl; x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100, wherein when R1represents hydrogen, then y is from 10 to 75.

[0098] In some embodiments, R1can represent a C1-C32 alkyl group. In some embodiments, R1can represent hydrogen. In some embodiments, R1can represent a C1-C32 alkenyl group. In some embodiments, R1can represent a C1-C32 alkynyl group. In some embodiments, R1can represent a cycloalkyl group. In some embodiments, R1can represent an aryl group. In some embodiments, R1can represent an alkylaryl group.

[0099] In some embodiments, R1represents , wherein R2, R3, and R4are each , , ments, embodiments, R2and R4are some embodiments, R4and R3are

[0100] In some embodiments, R1can represent . In some embodiments, R1can represent . In some embodiments, R1can represent . In some embodiments, R1can represent embodiments, R1can represent . In some embodiments, R1can represent In some embodiments, the alkoxy anionic compound is defined by: wherein,

[0101] BO represents -CH2-CH(ethyl)-O-;

[0102] PO represents -CH2-CH(methyl)-O-;

[0103] EO represents -CH2-CH2-O-;

[0104] Q represents sulfate, carboxylate, or carboxymethyl; x is an integer from 0 to 10; y is an integer from 0 to 75; z is an integer from 0 to 100;

[0105] In some embodiments, the alkoxy anionic compound is defined by: wherein,

[0106] BO represents -CH2-CH(ethyl)-O-;

[0107] PO represents -CH2-CH(methyl)-O-;

[0108] EO represents -CH2-CH2-O-;

[0109] Q represents sulfate, carboxylate, or carboxymethyl; x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100.

[0110] In some embodiments, the alkoxy anionic compound is defined by: wherein,

[0111] PO represents -CH2-CH(methyl)-O-;

[0112] EO represents -CH2-CH2-O-;

[0113] Q represents sulfate, carboxylate, or carboxymethyl; y is an integer from 0 to 75; z is an integer from 0 to 100;

[0114] R , R3, and R4are each independently wherein at least one

[0115] In some embodiments, the alkoxy anionic compound is defined by: wherein,

[0116] PO represents -CH2-CH(methyl)-O-;

[0117] EO represents -CH2-CH2-O-;

[0118] Q represents sulfate, carboxylate, or carboxymethyl; y is an integer from 0 to 75; and z is an integer from 0 to 100. In some embodiments, Q can represent sulfate. In some embodiments, Q can represent carboxylate. In some embodiments, Q can represent carboxymethyl.

[0119] In some embodiments, x can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0120] In some embodiments, x can be at least greater than 0 (e.g., at least 0. 1, at least 0.5, at least 1, at least 2.5, at least 5, or at least 7.5). In some embodiments, x can be 10 or less (e.g., 7.5 or less, 5 or less, 2.5 or less, 1 or less, 0.5 or less, or 0. 1 or less).

[0121] The x can be an integer ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, x can be an integer from 0 to 10 (e.g., from 0 to 7.5, from 0 to 5, from 0 to 2.5, from 1 to 10, from 1 to 7.5, from 1 to 5, from 1 to 2.5, from 5 to 10, from 5 to 7.5, or from 7.5 to 10).

[0122] In some embodiments, y can be 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, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, or 75.

[0123] In some embodiments, y can be at least greater than 0 (e.g., at least 0.5, at least 1, at least 5, at least 10, at least 15, at least 20, at least 25, at least 30, at least 35, at least 40, at least 45, at least 50, at least 55, at least 60, at least 65, or at least 70). In some embodiments, y can be 75 or less (e.g., 70 or less, 65 or less, 60 or less, 55 or less, 50 or less, 45 or less, 40 or less, 35 or less, 30 or less, 25 or less, 20 or less, 15 or less, 10 or less, 5 or less, 1 or less, 0.5 or less, or 0.1 or less).

[0124] The y can be an integer ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, y can be an integer from 0 to 75 (e.g., from 0 to 70, from 0 to 65, from 0 to 60, from 0 to 55, from 0 to 50, from 0 to 45, from 0 to 40, from 0 to 35, from 0 to 30, from 0 to 25, from 0 to 20, from 0 to 15, from 0 to 10, from 0 to 5, from 1 to 75, from 1 to 70, from 1 to 65, from 1 to 60, from 1 to 55, from 1 to 50, from 1 to 45, from 1 to 40, from 1 to 35, from 1 to 30, from 1 to 25, from 1 to 20, from 1 to 15, from 1 to 10, from 1 to 5, from 5 to 75, from 5 to 70, from 5 to 65, from 5 to 60, from 5 to 55, from 5 to 50, from 5 to 45, from 5 to 40, from 5 to 35, from 5 to 30, from 5 to 25, from 5 to 20, from 5 to 15, from 5 to 10, from 10 to 75, from 10 to 70, from 10 to 65, from 10 to

[0125] 60, from 10 to 55, from 10 to 50, from 10 to 45, from 10 to 40, from 10 to 35, from 10 to 30, from 10 to 25, from 10 to 20, from 10 to 15, from 15 to 75, from 15 to 70, from 15 to 65, from 15 to 60, from 15 to 55, from 15 to 50, from 15 to 45, from 15 to 40, from 15 to 35, from 15 to 30, from 15 to 25, from 15 to 20, from 20 to 75, from 20 to 70, from 20 to 65, from 20 to 60, from 20 to 55, from 20 to 50, from 20 to 45, from 20 to 40, from 20 to 35, from 20 to 30, from 20 to 25, from 25 to 75, from 25 to 70, from 25 to 65, from 25 to 60, from 25 to 55, from 25 to 50, from 25 to 45, from 25 to 40, from 25 to 35, from 25 to 30, from 30 to 75, from 30 to 70, from 30 to 65, from 30 to 60, from 30 to 55, from 30 to 50, from 30 to 45, from 30 to 40, from 30 to 35, from 30 to 40, from 35 to 75, from 35 to 70, from 35 to 65, from 35 to 60, from 35 to 55, from 35 to 50, from 35 to 45, from 35 to 40, from 40 to 75, from 40 to 70, from 40 to 65, from 40 to 60, from 40 to 55, from 40 to 50, from 40 to 45, from 45 to 75, from 45 to 70, from 45 to 65, from 45 to 60, from 45 to 55, from 45 to 50, from 50 to 75, from 50 to 70, from 50 to 65, from 50 to 60, from 50 to 55, from 55 to 75, from 55 to 70, from 55 to 65, from 55 to 60, from 60 to 75, from 60 to 70, from 60 to 65, from 65 to 75, from 65 to 70, or from 70 to 75).

[0126] In some embodiments, z can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,

[0127] 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,

[0128] 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70,

[0129] 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96,

[0130] 97, 98, 99, or 100.

[0131] In some embodiments, z can be at least greater than 0 (e.g., at least 0.5, at least 1, at least 5, at least 10, at least 15, at least 20, at least 25, at least 30, at least 35, at least 40, at least 45, at least 50, at least 55, at least 60, at least 65, or at least 70). In some embodiments, z can be 75 or less (e.g., 70 or less, 65 or less, 60 or less, 55 or less, 50 or less, 45 or less, 40 or less, 35 or less, 30 or less, 25 or less, 20 or less, 15 or less, 10 or less, 5 or less, 1 or less, 0.5 or less, or 0.1 or less).

[0132] The z can be an integer ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, z can be an integer from 0 to 100 (e.g., from 0 to 95, from 0 to 90, from 0 to 85, from 0 to 80, from 0 to 75, from 0 to 70, from 0 to 65, from 0 to 60, from 0 to 55, from 0 to 50, from 0 to 45, from 0 to 40, from 0 to 35, from 0 to 30, from 0 to 25, from 0 to 20, from 0 to 15, from 0 to 10, from 0 to 5, from 1 to 100, from 1 to 95, from 1 to 90, from 1 to 85, from 1 to 80, from 1 to 75, from 1 to 70, from 1 to 65, from 1 to 60, from 1 to 55, from 1 to 50, from 1 to 45, from 1 to 40, from 1 to 35, from 1 to 30, from 1 to 25, from 1 to 20, from 1 to 15, from 1 to 10, from 1 to 5, from 5 to 100, from 5 to 95, from 5 to 90, from 5 to 85, from 5 to 80, from 5 to 75, from 5 to 70, from 5 to 65, from 5 to 60, from 5 to 55, from 5 to 50, from 5 to 45, from 5 to 40, from 5 to 35, from 5 to 30, from 5 to 25, from 5 to 20, from 5 to 15, from 5 to 10, from 10 to 100, from 10 to 95, from 10 to 90, from 10 to 85, from 10 to 80, from 10 to 75, from 10 to 70, from 10 to 65, from 10 to 60, from 10 to 55, from 10 to 50, from 10 to 45, from 10 to 40, from 10 to 35, from 10 to 30, from 10 to 25, from 10 to 20, from 10 to 15, from 15 to 100, from 15 to 95, from 15 to 90, from 15 to 85, from 15 to 80, from 15 to 75, from 15 to 70, from 15 to 65, from 15 to 60, from 15 to 55, from 15 to 50, from 15 to 45, from 15 to 40, from 15 to 35, from 15 to 30, from 15 to 25, from 15 to 20, from 20 to 100, from 20 to 95, from 20 to 90, from 20 to 85, from 20 to 80, from 20 to 75, from 20 to 70, from 20 to 65, from 20 to 60, from 20 to 55, from 20 to 50, from 20 to 45, from 20 to 40, from 20 to 35, from 20 to 30, from 20 to 25, from 25 to 100, from 25 to 95, from 25 to 90, from 25 to 85, from 25 to 80, from 25 to 75, from 25 to 70, from 25 to 65, from 25 to 60, from 25 to 55, from 25 to 50, from 25 to 45, from 25 to 40, from 25 to 35, from 25 to 30, from 30 to 100, from 30 to 95, from 30 to 90, from 30 to 85, from 30 to 80, from 30 to 75, from 30 to 70, from 30 to 65, from 30 to 60, from 30 to 55, from 30 to 50, from 30 to 45, from 30 to 40, from 30 to 35, from 30 to 40, from 35 to 100, from 35 to 95, from 35 to 90, from 35 to 85, from 35 to 80, from 35 to 75, from 35 to 70, from 35 to 65, from 35 to 60, from 35 to 55, from 35 to 50, from 35 to 45, from 35 to 40, from 40 to 100, from 40 to 95, from 40 to 90, from 40 to 85, from 40 to 80, from 40 to 75, from 40 to 70, from 40 to 65, from 40 to 60, from 40 to 55, from 40 to 50, from 40 to 45, from 45 to 100, from 45 to 95, from 45 to 90, from 45 to 85, from 45 to 80, from 45 to 75, from 45 to 70, from 45 to 65, from 45 to 60, from 45 to 55, from 45 to 50, from 50 to 100, from 50 to 95, from 50 to 90, from 50 to 85, from 50 to 80, from 50 to 75, from 50 to 70, from 50 to 65, from 50 to 60, from 50 to 55, from 55 to 100, from 55 to 95, from 55 to 90, from 55 to 85, from 55 to 80, from 55 to 75, from 55 to 70, from 55 to 65, from 55 to 60, from 60 to 100, from 60 to 95, from 60 to 90, from 60 to 85, from 60 to 80, from 60 to 75, from 60 to 70, from 60 to 65, from 65 to 100, from 65 to 95, from 65 to 90, from 65 to 85, from 65 to 80, from 65 to 75, from 65 to 70, from 70 to 100, from 70 to 95, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 100, from 75 to 95, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 100, from 80 to 95, from 80 to 90, from 80 to 85, from 85 to 100, from 85 to 95, from 85 to 90, from 90 to 100, from 90 to 95, or from 95 to 100).

[0133] In some embodiments, x is 0. In some embodiments, y is 35. In some embodiments, y is 20. In some embodiments, z is 0. In some embodiments, z is 20. In some embodiments, x is 0, y is 35, and z is 20. In some embodiments, x is 0, y is 20, and z is 0.

[0134] In some embodiments, the alkoxy anionic compound can be: In some embodiments, the alkoxy anionic compound can be:

[0135] In some embodiments, the alkoxy anionic compound can be: In some embodiments, the alkoxy anionic compound can be present in the test sample in an amount of at least 1% by weight (e.g., at least 2% by weight, at least 4% by weight, at least 6% by weight, at least 8% by weight, at least 10% by weight, at least 12% by weight, or at least 14% by weight).

[0136] In some embodiments, the alkoxy anionic compound can be present in the test sample in an amount of 15% by weight or less (e.g., 14% by weight or less, 12% by weight or less, 10% by weight or less, 8% by weight or less, 6% by weight or less, 4% by weight or less, or 2% by weight or less). The alkoxy anionic compound can be present in the test sample in an amount ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the alkoxy anionic compound can be present in the test sample in an amount of from 1% to 15% by weight (e.g., from 1% to 10% by weight, from 1% to 8% by weight, from 1% to 6% by weight, from 1% to 4% by weight, from 1% to 2% by weight, from 2% to 15% by weight, from 2% to 10% by weight, from 2% to 8% by weight, from 2% to 6% by weight, from 2% to 4% by weight, from 4% to 15% by weight, from 4% to 10% by weight, from 4% to 8% by weight, from 4% to 6% by weight, from 6% to 15% by weight, from 6% to 10% by weight, from 6% to 8% by weight, from 8% to 15% by weight, from 8% to 10% by weight, or from 10% to 15% by weight).

[0137] In some embodiments, the compounds described herein can be used as a component of an injection fluid, or as a component of a hydraulic fracturing fluid.

[0138] Methods

[0139] Described herein are methods of measuring an alkoxy anionic compound cloud point, the method including: (i) contacting the alkoxy anionic compound with an inorganic salt solution to form a test sample; and (ii) increasing the test sample temperature from 1 to 90°C until the cloud point of the test sample including the alkoxy anionic compound is reached.

[0140] In some embodiments, increasing the test sample temperature from 1 to 90°C (e.g., from 1 to 80°C, from 1 to 70°C, from 1 to 60°C, from 1 to 50°C, from 1 to 40°C, from 1 to 30°C, from 1 to 20°C, from 1 to 10°C, from 10 to 90°C, from 10 to 80°C, from 10 to 70°C, from 10 to 60°C, from 10 to 50°C, from 10 to 40°C, from 10 to 30°C, from 10 to 20°C, from 20 to 90°C, from 20 to 80°C, from 20 to 70°C, from 20 to 60°C, from 20 to 50°C, from 20 to 40°C, from 20 to 30°C, from 30 to 90°C, from 30 to 80°C, from 30 to 70°C, from 30 to 60°C, from 30 to 50°C, from 30 to 40°C, from 40 to 90°C, from 40 to 80°C, from 40 to 70°C, from 40 to 60°C, from 40 to 50°C, from 50 to 90°C, from 50 to 80°C, from 50 to 70°C, from 50 to 60°C, from 60 to 90°C, from 60 to 80°C, from 60 to 70°C, from 70 to 90°C, from 70 to 80°C, from 80 to 90°C) until the cloud point of the test sample including the alkoxy anionic compound is reached.

[0141] Suitable inorganic salts can include, but are not limited to, sodium chloride (NaCl), potassium chloride (KC1), calcium carbonate (CaCCh), sodium carbonate (Na2COs), magnesium sulfate (MgSO4), magnesium chloride (MgCh), ammonium nitrate (NH4NO3), sodium bicarbonate (NaHCOs), potassium permanganate (KMnO4), sodium sulfate (Na2SO4), potassium sulfate (K2SO4), calcium chloride (CaCh), or magnesium chloride (MgCh). In some embodiments, the inorganic salt can be present in the test sample in an amount of at least 1% by weight (e.g., at least 2% by weight, at least 4% by weight, at least 6% by weight, at least 8% by weight, at least 10% by weight, at least 12% by weight, or at least 14% by weight).

[0142] In some embodiments, the inorganic salt can be present in the test sample in an amount of 15% by weight or less (e.g., 14% by weight or less, 12% by weight or less, 10% by weight or less, 8% by weight or less, 6% by weight or less, 4% by weight or less, or 2% by weight or less).

[0143] The inorganic salt can be present in the test sample in an amount ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the inorganic salt can be present in the test sample in an amount of from 1% to 15% by weight (e.g., from 1% to 10% by weight, from 1% to 8% by weight, from 1% to 6% by weight, from 1% to 4% by weight, from 1% to 2% by weight, from 2% to 15% by weight, from 2% to 10% by weight, from 2% to 8% by weight, from 2% to 6% by weight, from 2% to 4% by weight, from 4% to 15% by weight, from 4% to 10% by weight, from 4% to 8% by weight, from 4% to 6% by weight, from 6% to 15% by weight, from 6% to 10% by weight, from 6% to 8% by weight, from 8% to 15% by weight, from 8% to 10% by weight, or from 10% to 15% by weight).

[0144] Also described herein are methods of monitoring reaction progress, the method including: (i) measuring a cloud point for a reaction product including an alkoxy anionic compound using the method described herein; (ii) providing a reaction sample including the alkoxy anionic compound; (iii) contacting the reaction sample with an inorganic salt solution to form a test sample; (iv) increasing the test sample temperature from 1 to 90°C until a cloud point for the test sample is reached; (v) comparing the reaction product cloud point to the test sample cloud point; and (vi) repeating steps (ii) to (v) until the cloud point of the test sample is equal to the cloud point of the reaction product.

[0145] In some embodiments, increasing the test sample temperature from 1 to 90°C (e.g., from 1 to 80°C, from 1 to 70°C, from 1 to 60°C, from 1 to 50°C, from 1 to 40°C, from 1 to 30°C, from 1 to 20°C, from 1 to 10°C, from 10 to 90°C, from 10 to 80°C, from 10 to 70°C, from 10 to 60°C, from 10 to 50°C, from 10 to 40°C, from 10 to 30°C, from 10 to 20°C, from 20 to 90°C, from 20 to 80°C, from 20 to 70°C, from 20 to 60°C, from 20 to 50°C, from 20 to 40°C, from 20 to 30°C, from 30 to 90°C, from 30 to 80°C, from 30 to 70°C, from 30 to 60°C, from 30 to 50°C, from 30 to 40°C, from 40 to 90°C, from 40 to 80°C, from 40 to 70°C, from 40 to 60°C, from 40 to 50°C, from 50 to 90°C, from 50 to 80°C, from 50 to 70°C, from 50 to 60°C, from 60 to 90°C, from 60 to 80°C, from 60 to 70°C, from 70 to 90°C, from 70 to 80°C, from 80 to 90°C) until the cloud point of the test sample including the alkoxy anionic compound is reached.

[0146] Suitable inorganic salts can include, but are not limited to, sodium chloride (NaCl), potassium chloride (KC1), calcium carbonate (CaCOp, sodium carbonate (NaaCOa), magnesium sulfate (MgSOp, magnesium chloride (MgCh), ammonium nitrate (NH4NO3), sodium bicarbonate (NaHCOp, potassium permanganate ( KMnOp. sodium sulfate (NaaSO , potassium sulfate (K2SO4), calcium chloride (CaCh), or magnesium chloride (MgCh).

[0147] In some embodiments, the inorganic salt can be present in the test sample in an amount of at least 1% by weight (e.g., at least 2% by weight, at least 4% by weight, at least 6% by weight, at least 8% by weight, at least 10% by weight, at least 12% by weight, or at least 14% by weight).

[0148] In some embodiments, the inorganic salt can be present in the test sample in an amount of 15% by weight or less (e.g., 14% by weight or less, 12% by weight or less, 10% by weight or less, 8% by weight or less, 6% by weight or less, 4% by weight or less, or 2% by weight or less).

[0149] The inorganic salt can be present in the test sample in an amount ranging from any of the minimum values described above to any of the maximum values described above. For example, in some embodiments, the inorganic salt can be present in the test sample in an amount of from 1% to 15% by weight (e.g., from 1% to 10% by weight, from 1% to 8% by weight, from 1% to 6% by weight, from 1% to 4% by weight, from 1% to 2% by weight, from 2% to 15% by weight, from 2% to 10% by weight, from 2% to 8% by weight, from 2% to 6% by weight, from 2% to 4% by weight, from 4% to 15% by weight, from 4% to 10% by weight, from 4% to 8% by weight, from 4% to 6% by weight, from 6% to 15% by weight, from 6% to 10% by weight, from 6% to 8% by weight, from 8% to 15% by weight, from 8% to 10% by weight, or from 10% to 15% by weight).

[0150] Also described herein are methods of preparing an alkoxy anionic compound, the methods including: (i) reacting an alcohol alkoxylate with a sulfonating agent, carboxylating agent, carboxymethylating agent, or sulfating agent to generate a reaction product including an alkoxy anionic compound; (ii) monitoring the reaction progress using the method described herein; and (iii) quenching the reaction when the cloud point of the test sample is equal to the cloud point of the reaction product. In some embodiments, the method further includes (iv) isolating the reaction product.

[0151] In some embodiments, the alcohol alkoxylate can be defined by Formula II below: R1-O-(BO)x-(PO)y-(EO)z-Q

[0152] Formula II wherein,

[0153] BO represents -CH2-CH(ethyl)-O-;

[0154] PO represents -CH2-CH(methyl)-O-;

[0155] EO represents -CH2-CH2-O-;

[0156] R1represents a hydrogen, a C1-C32 alkyl group, a C1-C32 alkenyl group, a C1-C32 alkynyl group, a cycloalkyl group, an aryl group, or an alkylaryl group;

[0157] Q represents hydrogen; x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100, wherein when R1represents hydrogen, then y is from 10 to 75.

[0158] In some embodiments, reacting step (i) can include reacting an alcohol alkoxylate with a sulfonating agent to generate a reaction product including an alkoxy anionic compound. In such embodiments, the alkoxy anionic compound can be an alkoxy sulfonate compound. In some embodiments, reacting step (i) can include reacting an alcohol alkoxylate with a carboxylating agent to generate a reaction product including an alkoxy anionic compound. In such embodiments, the alkoxy anionic compound can be an alkoxy carboxylate compound. In some embodiments, reacting step (i) can include reacting an alcohol alkoxylate with a carboxymethylating agent to generate a reaction product including an alkoxy anionic compound. In such embodiments, the alkoxy anionic compound can be an alkoxy carboxy methylated compound. In some embodiments, reacting step (i) can include reacting an alcohol alkoxylate with a sulfating agent to generate a reaction product including an alkoxy anionic compound. In such embodiments, the alkoxy anionic compound can be an alkoxy sulfate compound.

[0159] In some embodiments, the sulfonating agent can include sulfuric acid (H2SO4), sulfur trioxide (SO3), chlorosulfuric acid (HSO3CI), or CH3CO2SO3H. In some embodiments, the carboxyalting agent can include CO2, bicarbonate. In some embodiments, the carboxymethylating agent can include monochloroacetic acid. In some embodiments, the sulfating agent can include sulfamic acid (H3NSO3).

[0160] 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.

[0161] By way of non-limiting illustration, examples of certain embodiments of the present disclosure are given below.

[0162] EXAMPLES

[0163] Example 1: Preparation of an alkoxy anionic compound

[0164] Develop a reliable method (Cloud Point method) to follow the reaction progress during a Sulfation (and Carboxy methylation and sulfonation) process of an alcohol alkoxylate wherein we can end the reaction at the desired level of sulfation (based on performance testing) without “over cooking” the batch which leads to undesirable by-products which can answer for anionic active level by activity level titration.

[0165] Experimental:

[0166] 1-15% alcohol alkoxysulfate in water with 1-15% Na2COr are mixed at l-90°C to identify a sharp cloud point. Other alkoxy anionics such as carboxylate and sulfonates can be used. Other inorganic salts can also be used instead of Na2CO3.

[0167] This protocol can be used during a production process until the desired cloud point is reached.

[0168] The alkoxy anionic can be R-xPO-yEO-Z where R is C1-C32 where C3 and higher can be linear or branched and where G> and higher can be linear or alicyclic, aromatic or alkyl aromatic (mono or polynuclear) and where x is 0-75 and y is 0-100 and Z is anionic as in sulfate, carboxy methyl (methylene carboxylate), C1-3 sulfonate including hydroxypropyl sulfonate. In some embodiments, R can be zero as in diol- and polyol alkoxylates and x can be 10-75 and y is 0- 100.

[0169] The cloud point of TSP-35PO-20EO-Sulfate was assayed using the method described herein. 10% TSP-35PO-20EO-Sulfate and 4% Na2CO3 in DI were combined. Different amounts of non-ionic alcohol alkoxylate (TSP-35PO-20EO-OH) were added and the cloud point was determined. Results are shown in Table 1 below. Table 1

[0170] The cloud point of 2EH-20PO-Sulfate was assayed using the method described herein.

[0171] 10% 2EH-20PO-Sulfate and 2% NasCCL in DI were combined. Different amounts of non-ionic alcohol alkoxylate (2EH-20PO-OH) were added and the cloud point was determined. Results are shown in Table 2 below.

[0172] Table 2

[0173] 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 method of measuring an alkoxy anionic compound cloud point, the method comprising:(i) contacting the alkoxy anionic compound with an inorganic salt solution to form a test sample; and(ii) increasing the test sample temperature from 1 to 90°C until the cloud point of the test sample including the alkoxy anionic compound is reached.

2. The method of claim 1, wherein the alkoxy anionic compound is defined by Formula I below:R1-O-(BO)x-(PO)y-(EO)z-QFormula I wherein,BO represents -CH2-CH(ethyl)-O-;PO represents -CH2-CH(methyl)-O-;EO represents -CH2-CH2-O-;R1represents a hydrogen, a C1-C32 alkyl group, a C1-C32 alkenyl group, a Ci- C32 alkynyl group, a cycloalkyl group, an aryl group, or an alkylaryl group;Q represents sulfate, carboxylate, or carboxy methyl; x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100, wherein when R1represents a hydrogen, then y is from 10 to 75.

3. The method of claim 2, wherein R1represents a C1-C32 alkyl group.

4. The method of any one of claims 2-3, wherein R1represents5. The method of any one of claims 1-4, wherein the alkoxy anionic compound is defined bywherein, BO represents -CH2-CH(ethyl)-O-; PO represents -CH2-CH(methyl)-O-; EO represents -CH2-CH2-O-; Q represents sulfate, carboxylate, or carboxy methyl; x is an integer from 0 to 10; y is an integer from 0 to 75; z is an integer from 0 to 100;6. The method of any one of claims 2-5, wherein Q represents sulfate.

7. The method of any one of claims 2-6, wherein Q represents sulfonate.

8. The method of any one of claims 2-7, wherein y is an integer from 10 to 75.

9. The method of any one of claims 2-8, wherein z is an integer from 10 to 75.

10. The method of claim 2, wherein R1represents hydrogen.

11. The method of any one of claims 1-9, wherein the alkoxy anionic compound is12. The method of any one of claims 1-11, wherein the alkoxy anionic compound is present in the test sample in an amount of from 1 % to 15% by weight.

13. The method of any one of claims 1-12, wherein an inorganic salt is present in the test sample in an amount of from 1% to 15% by weight.

14. The method of any one of claims 1-13, wherein the inorganic salt solution comprises sodium chloride (NaCl), potassium chloride (KC1), calcium carbonate (CaCCh), sodium carbonate (Na2COa), magnesium sulfate (MgSO i), magnesium chloride (MgCh), ammonium nitrate (NH4NO3), sodium bicarbonate (NaHCCh), potassium permanganate (KMnO4), sodium sulfate (Na2SO4), potassium sulfate (K2SO4), calcium chloride (CaCh), or magnesium chloride (MgCh).

15. A method of monitoring reaction progress, the method comprising:(i) determining a cloud point for a reaction product comprising an alkoxy anionic compound using the method of any one of claims 1-14;(ii) providing a reaction sample comprising the alkoxy anionic compound;(iii) contacting the reaction sample with an inorganic salt solution to form a test sample;(iv) increasing the test sample temperature from 1 to 90°C until a cloud point for the test sample is reached;(v) comparing the reaction product cloud point to the test sample cloud point; and(vi) repeating steps (ii) to (v) until the cloud point of the test sample is equal to the cloud point of the reaction product.

16. The method of claim 15, wherein the alkoxy anionic compound is defined by Formula I below:R1-O-(BO)x-(PO)y-(EO)z-QFormula I wherein,BO represents -CH2-CH(ethyl)-O-;PO represents -CH2-CH(methyl)-O-;EO represents -CH2-CH2-O-;R1represents a hydrogen, a C1-C32 alkyl group, a C1-C32 alkenyl group, a Ci- C32 alkynyl group, a cycloalkyl group, an aryl group, or an alkylaryl group;Q represents sulfate, carboxylate, or carboxy methyl; x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100; wherein when R1represents a hydrogen, then y is from 10 to 75.

17. The method of claim 16, wherein R1represents a C1-C32 alkyl group.

18. The method of any one of claims 16-17, wherein R1represents19. The method of any one of claims 15-18, wherein the alkoxy anionic compound is defined bywherein,BO represents -CH2-CH(ethyl)-O-;PO represents -CH2-CH(methyl)-O-;EO represents -CH2-CH2-O-;Q represents sulfate, carboxylate, or carboxy methyl; x is an integer from 0 to 10; y is an integer from 0 to 75; z is an integer from 0 to 100;20. The method of any one of claims 16-19, wherein Q represents sulfate.

21. The method of any one of claims 16-19, wherein Q represents sulfonate.

22. The method of any one of claims 16-21, wherein y is an integer from 10 to 75.

23. The method of any one of claims 16-22, wherein z is an integer from 10 to 75.

24. The method of claim 16, wherein R1represents hydrogen.

25. The method of any one of claims 16-23, wherein the alkoxy anionic compound is26. The method of any one of claims 16-25, wherein the alkoxy anionic compound is present in the test sample in an amount of from 1 % to 15% by weight.

27. The method of any one of claims 16-25, wherein an inorganic salt is present in the test sample in an amount of from 1% to 15% by weight.

28. The method of any one of claims 16-27, wherein the inorganic salt solution comprises sodium chloride (NaCl), potassium chloride (KC1), calcium carbonate (CaCCh), sodium carbonate (Na^CCb), magnesium sulfate (MgSO i), magnesium chloride (MgCh), ammonium nitrate (NH4NO3), sodium bicarbonate (NaHCC ), potassium permanganate (KMnO4), sodium sulfate (Na2SO4), potassium sulfate (K2SO4), calcium chloride (CaCh), or magnesium chloride (MgCh).

29. A method of preparing an alkoxy anionic compound, the method comprising:(i) reacting an alcohol alkoxylate with a sulfonating agent, carboxylating agent, carboxymethylating agent, or sulfating agent to generate a reaction product comprising an alkoxy anionic compound;(ii) monitoring the reaction progress using the method of any of claims 15-28; and(iii) quenching the reaction when the cloud point of the test sample is equal to the cloud point of the reaction product.

30. The method of claim 29, further comprising (iv) isolating the reaction product.

31. The method of any one of claims 29-30, wherein the alcohol alkoxylate is defined by Formula II below:R1-O-(BO)x-(PO)y-(EO)z-QFormula II wherein,BO represents -CH2-CH(ethyl)-O-;PO represents -CH2-CH(methyl)-O-;EO represents -CH2-CH2-O-;R1represents a hydrogen, a C1-C32 alkyl group, a C1-C32 alkenyl group, a Ci- C32 alkynyl group, a cycloalkyl group, an aryl group, or an alkylaryl group;Q represents hydrogen; x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100; wherein when R1represents a hydrogen, then y is from 10 to 75.

32. The method of any one of claims 29-31, wherein the alkoxy anionic compound is defined by Formula I below:R1-O-(BO)x-(PO)y-(EO)z-QFormula I wherein,BO represents -CH2-CH(ethyl)-O-;PO represents -CH2-CH(methyl)-O-;EO represents -CH2-CH2-O-;R1represents a hydrogen, a C1-C32 alkyl group, a C1-C32 alkenyl group, a Ci-C32 alkynyl group, a cycloalkyl group, an aryl group, or an alkylaryl group;Q represents sulfate, carboxylate, or carboxy methyl;x is an integer from 0 to 10; y is an integer from 0 to 75; and z is an integer from 0 to 100; wherein when R1represents a hydrogen, then y is from 10 to 75.

33. The method of any one of claims 29-32, wherein R1represents a C1-C32 alkyl group.

34. The method of any one of claims 31 -33, wherein R1representswherein35. The method of any one of claims 29-34, wherein the alkoxy anionic compound is defined bywherein, BO represents -CH2-CH(ethyl)-O-; PO represents -CH2-CH(methyl)-O-; EO represents -CH2-CH2-O-; Q represents sulfate, carboxylate, or carboxy methyl; x is an integer from 0 to 10;y is an integer from 0 to 75; z is an integer from 0 to 100;36. The method of any one of claims 31-35, wherein Q represents sulfate.

37. The method of any one of claims 31-35, wherein Q represents sulfonate.

38. The method of any one of claims 31-37, wherein y is an integer from 10 to 75.

39. The method of any one of claims 31-38, wherein z is an integer from 10 to 75.

40. The method of claim 31 or claim 32, wherein R1represents hydrogen.

41. The method of any one of claims 29-40, wherein the alkoxy anionic compound is

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