Carbonate reaction products of alkyl glycosides and methods of use thereof

Abstract

Comprising an organic carbonate having an anionic moiety, which is a carbonate reaction product of an alkyl glycoside, can exhibit surfactant properties. When dissolved in an aqueous fluid, such organic carbonates can exhibit relatively low interfacial tension values and maintain resistance to the presence of salts in the aqueous fluid. As a non-limiting example, an aqueous fluid containing the organic carbonate may be introduced into a subterranean formation in conjunction with an enhanced oil recovery process.

Description

Technical Field

[0001] The present disclosure relates generally to surfactants and, more particularly, to surfactants that exhibit compatibility with saline environments and are produced from biologically derived materials. Background Art

[0002] Compounds that have both hydrophobic and hydrophilic regions in their molecular structure are amphipathic and can exhibit surface activity. Therefore, these compounds are commonly referred to as "surfactants" or "surfactant compounds". Due to their molecular structure, surfactants tend to reduce the interfacial tension at the interface between two substances. Due to their ability to reduce interfacial tension, and to promote other properties associated therewith (e.g., foaming, emulsification, de-emulsification, surface wetting, etc.), surfactants can be used in a wide range of consumer and industrial products and processes. Among these consumer and industrial products, for example, there are soaps, detergents, cosmetics, medicines, paints and dispersants.

[0003] Surfactants are also commonly used in the oil and gas industry, such as during enhanced hydrocarbon recovery (e.g., enhanced oil recovery, EOR) processes. In EOR and similar downhole processes, surfactants can, as non-limiting examples, change the wettability of a surface to facilitate release of hydrocarbons from the surface, facilitate emulsification or de-emulsification of oleaginous materials, and / or reduce the viscosity of a fluid.

[0004] Although they are widely used, there are difficulties associated with various conventional surfactants. Many common surfactants show poor biodegradability and / or varying degrees of aquatic toxicity. Therefore, these types of surfactants may be subject to the constraints of various environmental and / or other government regulations. In addition, many surfactants are quite expensive, and some surfactants may show limited tolerance to environments with high salinity (e.g., about 5wt% or higher salts, including aqueous salt solutions, seawater and brine). Finally, although surfactants may tend to reduce the interfacial tension at the interface between two substances, some surfactant aqueous solutions themselves may show surface tension values ​​higher than required, especially under critical micelle concentration. Limited salt tolerance may limit the scope of application that many conventional surfactants can effectively use, and when using these surfactants, high interfacial tension values ​​may complicate fluid handling. Summary of the invention

[0005] The various details of the present disclosure are summarized below to provide a basic understanding. The present disclosure is not an exhaustive review of the present invention, and is neither intended to identify certain elements of the present invention nor to limit the scope of the present invention. On the contrary, the main purpose of the present disclosure is to present some concepts of the present disclosure in a simplified form before the more detailed description presented below.

[0006] In various aspects, the present disclosure provides compositions comprising: an organic carbonate comprising an anionic moiety that is a carbonate reaction product of an alkyl glycoside.

[0007] In other aspects, the present disclosure provides methods of treating a subterranean formation, comprising: providing a composition comprising an organic carbonate, the organic carbonate comprising an anionic portion, the anionic portion being a carbonate reaction product of an alkyl glycoside; and introducing the composition into a subterranean formation.

[0008] In other aspects, the present disclosure provides a method for preparing an organic carbonate, comprising: contacting an alkyl glycoside with high-pressure carbon dioxide in the presence of a non-nucleophilic base; and obtaining an organic carbonate, wherein the organic carbonate comprises a cation portion and an anion portion, wherein the cation portion comprises the non-nucleophilic base in a protonated form, and the anion portion is a carbonate reaction product of the alkyl glycoside.

[0009] Any combination of the various embodiments and implementations disclosed herein may be used in another embodiment consistent with the present disclosure.These and other aspects and features may be understood from the following description of certain embodiments presented herein, in light of the present disclosure and the accompanying drawings and claims. BRIEF DESCRIPTION OF THE DRAWINGS

[0010] The following drawings are included to illustrate certain aspects of the present disclosure and should not be considered to be exclusive embodiments. The disclosed subject matter is capable of considerable modification, alteration, combination, and equivalents in form and function without departing from the scope of the present disclosure.

[0011] Figure 1 It is a comparative FTIR spectra of the reaction products of alkyl polyglycoside and alkyl polyglycoside carbonate.

[0012] Figure 2 It is a comparative UV-visible spectrum of the reaction products of alkyl polyglycoside and alkyl polyglycoside carbonate.

[0013] Figure 3 is a graph of the interfacial tension of the reaction product of an alkyl glycoside and an alkyl glycoside carbonate as a function of time. DETAILED DESCRIPTION

[0014] The present disclosure relates generally to surfactants and, more particularly, to surfactants that exhibit compatibility with saline environments and are produced from biologically derived materials.

[0015] As mentioned above, conventional surfactants may have various problems, such as high cost, poor biocompatibility or biodegradability, limited compatibility with environments with high salinity, and high interfacial tension values. One or more of these factors can limit the applicability of these surfactants in various applications. Surfactants incompatible with high salinity environments can precipitate when contacting therewith, while surfactants can remain soluble (compatible) when contacting with water or aqueous fluids with enough low salinity.

[0016] Alkyl glycosides are sugar oligomers or polymers known to be surface active and biodegradable. Alkyl glycosides comprise a sugar polymer backbone having adjacent monosaccharide units linked by glycosidic bonds, wherein the terminal monosaccharide unit is functionalized by a long chain alkyl group on an oxygen atom that would otherwise form a glycosidic bond with another monosaccharide unit. Although alkyl glycosides can be useful nonionic surfactants in a variety of applications, alkyl glycosides may exhibit limited tolerance to aqueous saline solutions. In addition, the alkyl glycosides produced may exhibit unacceptably high interfacial tensions.

[0017] The disclosure shows that the properties of alkyl glycosides can be surprisingly enhanced by chemically converting the parent alkyl glycoside from a neutral surfactant into an anionic surfactant. Especially, by functionalizing at least a portion of the monosaccharide units of the parent alkyl glycoside with organic carbonate groups, particularly as the salt of the organic carbonate groups, the raising of the tolerance to aqueous salt solutions and similar high salinity environments can be achieved. More surprisingly, after the carbonate reaction product functionalization as a salt form, compared with the parent alkyl glycoside of similar concentration in aqueous fluids, the interfacial tension of reduction can be achieved.

[0018] Advantageously, by using carbon dioxide in the presence of a suitable strong base, organic carbonate groups can be easily introduced into alkyl glycosides and converted into salt forms, wherein the strong base can deprotonate the organic carbonate groups to produce salt forms. Not limited by theory or mechanism, it is believed that organic carbonate groups are formed at the primary alcohol position of at least a portion of the monosaccharide units that limit the sugar polymer backbone (in the case where the alkyl glycosides mainly comprise 1,4-glycosidic bonds). Forming organic carbonate groups on the secondary alcohol position of the monosaccharide units in the alkyl glycosides that mainly comprise 1,4-glycosidic bonds is considered to be more difficult due to the increased steric hindrance. In addition, the organic carbonate groups introduced by reacting with carbon dioxide in the presence of a suitable strong base can be different from the cyclic carbonates formed by reacting adjacent hydroxyls with reagents such as phosgene.

[0019] Thus, the composition of the present disclosure may include an organic carbonate having an anionic portion that is a carbonate reaction product of an alkyl glycoside. An alkyl glycoside having all α(1,4) glycosidic bonds between adjacent glucose monomers may have a structure represented by Formula 1 below, wherein

[0020]

[0021] The variable a is 0 or a positive integer, and R is the alkyl group on the terminal glucose monomer unit, which defines the "alkyl" portion of the alkyl glycoside. The molecular weight of the alkyl glycoside can vary within a numerical range, such as about 220 or higher, or about 380 or higher, or about 545 or higher, or 700 or higher. In non-limiting examples, the alkyl group may include C4-C 24 Alkyl, or C6-C 20 Alkyl, or C8-C 18 Alkyl, or C6-C 14 Alkyl, or C 10 -C 16 Alkyl, or C 12 -C 14 Alkyl. It should be understood that a given alkyl glycoside preparation can contain different numbers of monosaccharide units, and different ranges of alkyl group sizes. Therefore, in a non-limiting example, the molecular weight of a suitable alkyl glycoside for use in the disclosure herein can be from about 220 to about 5000, or from about 320 to about 2000, or from about 320 to about 1000, or from about 400 to about 800, or from about 600 to about 1200, or from about 350 to about 750. Before one or more organic carbonate groups are introduced into the parent alkyl glycoside in the form of a salt, there can be as little as one monosaccharide unit in the parent alkyl glycoside, or as many as 2,3,4,5,10,15 or even 20 monosaccharide units. Therefore, it should be understood that the term "alkyl glycoside" used herein can refer to an alkyl monoglucosidase (a monosaccharide unit) or an alkyl polyglucosidase (two or more monosaccharide units). It is further understood that alkyl glycosides having monosaccharide units other than glucose and / or glycosidic bonds other than α(1,4)-glycosidic bonds may also be suitable for use in the disclosure herein. For clarity, Formula 2 shows the IUPAC numbering of a single glucose monomer unit (in the form of an alkyl glycoside).

[0022]

[0023] The organic carbonate of the present disclosure may include at least one monosaccharide unit having a structure represented by the following Formula 3, wherein the C-1 and C-4 alcohol groups may be in the form of a glycosidic bond (in the case of an alkyl polyglycoside), or the C-4 alcohol group of the terminal monosaccharide unit of the alkyl polyglycoside may be alkyl functionalized.

[0024]

[0025] In Formula 3, B is the protonated form of a strong base.

[0026] Alkyl glycosides that undergo further functionalization to produce organic carbonates according to the disclosure herein can be commercially available or synthesized in any suitable manner. In a non-limiting example, suitable alkyl glycosides can be synthesized by reacting monosaccharides (e.g., glucose) or oligosaccharides (e.g., multiple glucose monomer units connected by α (1,4)-glycosidic bonds) with fatty alcohols or fatty alcohol mixtures in the presence of a suitable acid catalyst. The acid catalyst can promote the oligomerization (or further oligomerization) of monosaccharide units, wherein the glycosidic bond position of the terminal monosaccharide unit (i.e., C-4 alcohol group in the case of glucose) is etherified by the alkyl of the fatty alcohol to form a variety of alkyl glycosides. The various alkyl glycosides can have a range of monosaccharide units connected by glycosidic bonds, each alkyl glycoside having a terminal monosaccharide unit functionalized with an alkyl group. When a mixture of fatty alcohols is used, a range of alkyl group sizes can be present. Alkyl glycosides formed by other synthetic methods may also be applicable to the disclosure herein.

[0027] As used herein, the term "fatty alcohol" refers to an alcohol having an optional degree of unsaturation and containing 4 or more carbon atoms, such as about 4 to about 26 carbon atoms, or about 6 to about 24 carbon atoms, or about 8 to about 20 carbon atoms, or about 10 to about 18 carbon atoms, or about 6 to about 14 carbon atoms. The fatty alcohol (or mixture of fatty alcohols) used to prepare the alkyl glycoside can be formed by reducing a fatty acid or a fatty acid ester (preferably a straight-chain fatty acid or a fatty acid ester). Therefore, according to various embodiments, the alkyl glycosides disclosed herein may be free of or substantially free of branched alkyl groups. Fatty acids can be directly reduced to the corresponding fatty alcohols using known techniques. Fatty esters (including fats or oils) can be directly reduced to the corresponding fatty alcohols using known techniques, or the fatty esters can be first hydrolyzed to fatty acids before reduction. Therefore, the alkyl glycosides used herein may contain an alkyl group of comparable size to the fatty acid or fatty ester used to prepare the fatty alcohols.

[0028] Exemplary fatty acids (or fatty acids in fatty esters) from which corresponding fatty alcohols can be derived by various techniques include, for example, butyric acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, nonadecanoic acid, arachidic acid, heneicosanoic acid, behenic acid, tricosanoic acid, lignoceric acid, pentacosanoic acid, cerotic acid, crotonic acid, docosahexaenoic acid, linoleic acid, trans-linoleic acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, sappenic acid, hexadecano ... acid), vaccenic acid, guarana acid, oleic acid, pinoleic acid, octadecatetraenoic acid, eleostearic acid, elaidic acid, gondoic acid, gadoleic acid, erucic acid, eicosenoic acid, eicosadienoic acid, eicosatrienoic acid, eicosatetraenoic acid, docosadienoic acid, neuraminic acid, mead acid, adrenic acid, etc., and any combination thereof.

[0029] In a non-limiting example, glycerides may include a fatty ester source for obtaining fatty alcohols to form alkyl glycosides suitable for use herein. Suitable glycerides from which a mixture of one or more fatty alcohols may be obtained by a suitable reduction technique include any vegetable oil, animal oil, vegetable fat, animal fat, or any combination thereof containing one or more desired fatty acids. Suitable glycerides can be found in plant or animal sources, including, for example, soybean oil, grapeseed oil, olive oil, palm oil, rice bran oil, safflower oil, corn oil, coconut oil, sunflower seed oil, canola oil, rapeseed oil, peanut oil, cottonseed oil, hazelnut oil, tea seed oil, linseed oil, sesame oil, acai oil, almond oil, beech oil, Brazil nut oil, cashew oil, macadamia oil, pecan oil, pine nut oil, pistachio oil, walnut oil, pumpkin seed oil, apricot oil, avocado oil, grapefruit oil, lemon oil, orange oil, mango oil, linseed oil, fish oil, cocoa butter, castor oil, tall oil, fish oil, beef fat, buffalo oil, sheep oil, goat oil, duck oil, lard, poultry oil, and any combination thereof.

[0030] As mentioned above, the formation of the organic carbonate can be carried out by reaction with carbon dioxide in the presence of a suitable base. Suitable bases may include non-nucleophilic bases, preferably with a pK a is a non-nucleophilic strong base of about 10 or greater. More preferably, the non-nucleophilic base may include an amidine, preferably a cyclic or bicyclic amidine. Examples of suitable amidines that can promote the formation of organic carbonates include, but are not limited to, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) and any combination thereof. Therefore, in some embodiments, the cationic portion of the organic carbonate of the present disclosure may include DBU or DBN, particularly a protonated form of DBU or DBN.

[0031] Compositions disclosed herein can be further prepared with aqueous fluids, wherein organic carbonates are at least partially dissolved and preferably completely dissolved. Aqueous fluids that may be present in compositions disclosed herein include, but are not limited to, mixtures of water, salt water, water and water-miscible organic solvents, brine, seawater, produced water, or any combination thereof. As used herein, term "brine" refers to any aqueous salt solution having a greater amount of total dissolved salt than seawater, including saturated aqueous salt solutions. Oil fields or industrial production water containing high salt content can be appropriately used, including produced water from wellbore. Compositions disclosed herein can be prepared with aqueous fluids already having high salt content (e.g., based on the total mass of aqueous fluids, greater than 5wt% salt), while still maintaining tolerance (stable preparation) in the presence of high salt content. Alternatively, compositions disclosed herein can be prepared with aqueous fluids that do not contain dissolved salts or are not considered to constitute the amount of dissolved salts of high salt content. In addition, when contacting with another aqueous fluid with high salt content, the composition can maintain tolerance (stable preparation). The tolerance of the composition to high salinity aqueous fluids can be demonstrated by lack of precipitation or reduced transparency.

[0032] In the compositions of the present disclosure, the organic carbonate may be present in the aqueous fluid at a concentration of about 20 wt % or less, or about 10 wt % or less, or about 5 wt % or less, for example, from about 1 wt % to about 10 wt %, or from about 3 wt % to about 8 wt %, each concentration based on the total mass of the composition.

[0033] When in contact with an oily substance, the composition of the present disclosure can promote its emulsification, preferably as an oil-in-water emulsion. Advantageously, the emulsion can spontaneously break within about 24 hours, or within about 12 hours, or within about 8 hours, or within about 4 hours, or within about 2 hours, or within about 1 hour, or within about 30 minutes, or within about 20 minutes, or within about 10 minutes, or within about 5 minutes. Optionally, demulsification can be promoted by introducing a separate demulsifier.

[0034] The oleaginous substance that can be emulsified when contacting the composition of the present disclosure (including under high salinity conditions) is believed to be not particularly limited. Exemplary oleaginous substances may include, for example, petroleum, refined petroleum, diesel, natural gas, vegetable oil, vegetable oil, oilfield fluid or its component, or any combination thereof.

[0035] Advantageously, the composition of the present disclosure can show low interfacial tension values. At least, the composition of the present disclosure can show an interfacial tension lower than the corresponding alkyl glycoside before being converted into organic carbonate. That is to say, when prepared in an aqueous fluid with substantially the same concentration, the organic carbonate of alkyl glycoside can show an interfacial tension lower than the corresponding unfunctionalized (parent) alkyl glycoside. In a non-limiting example, the interfacial tension of the organic carbonate can be reduced by at least 5 times relative to unfunctionalized alkyl glycoside. More preferably, relative to unfunctionalized alkyl glycoside, the interfacial tension can be reduced by at least 10 times, or at least 15 times, or at least 20 times, or at least 30 times, or at least 40 times, or at least 50 times. Alternatively, at a concentration of 0.5 wt % or less, or 0.2 wt % or less, the interfacial tension value of the organic carbonate described herein may be about 0.3 mN / m or less, or about 0.25 mN / m or less, or about 0.2 mN / m or less, or about 0.15 mN / m or less, or about 0.1 mN / m or less, or about 0.05 mN / m or less, or about 0.01 mN / m or less.

[0036] As described above, the composition of the present disclosure can be obtained by contacting an alkyl glycoside with high-pressure carbon dioxide in the presence of a non-nucleophilic strong base (preferably an amidine, such as DBU or DBN), and obtaining an organic carbonate comprising a cation portion containing a protonated form of the non-nucleophilic base and an anion portion as a carbonate reaction product of the alkyl glycoside.

[0037] Preferably, the contact of the alkyl glycoside with carbon dioxide can be carried out in an aprotic organic solvent (reaction solvent) under heating. In a non-limiting example, suitable aprotic organic solvents may include, for example, dimethylformamide, dimethyl sulfoxide, dimethyl propylene urea, etc., or any combination thereof. In some or other non-limiting examples, heating may be carried out at a temperature higher than room temperature (25°C), up to about 100°C, or up to about 90°C, or up to about 80°C, up to about 70°C, or up to about 60°C. The suitable elevated pressure of carbon dioxide may be in the range of about 2atm to about 10atm, or about 2.5atm to about 7.5atm, or about 3atm to about 5atm, or about 4atm to about 6atm.

[0038] After obtaining organic carbonate by contacting alkyl glycoside with carbon dioxide, the method of the present disclosure may further include separating organic carbonate from reaction solvent. In a non-limiting example, organic carbonate can be separated using, for example, techniques such as (but not limited to) filtration, sedimentation, decantation, centrifugation or any combination thereof. After separating organic carbonate, the separated organic carbonate can be further washed with a washing solvent to remove the reaction solvent. Suitable washing solvents may include those with a low boiling point, and the organic carbonate is insoluble therein, but the reaction solvent is at least partially soluble therein. In a non-limiting example, suitable washing solvents may include, but are not limited to, hydrocarbon solvents, such as hexane. Optionally, the organic carbonate can be further freeze-dried or dried under vacuum and / or heating to further remove washing solvent, residual carbon dioxide, residual reaction solvent or any combination thereof.

[0039] After obtaining organic carbonate according to above, organic carbonate can be further dissolved in aqueous fluid.Suitable aqueous fluid can include those described above.The concentration of organic carbonate in aqueous fluid can include those specified above.In specific example, aqueous fluid can include at least one salt (for example, salt water, aqueous salt solution, seawater etc.).

[0040] Compositions of the present disclosure can be used in any application requiring surface activity. In non-limiting examples, the composition can be used to recover hydrocarbons from underground formations, for example, in combination with enhanced oil recovery processes. In some or other non-limiting examples, the composition can be introduced into underground formations to promote the emulsification of downhole oily substances or to promote the demulsification of existing emulsions downhole. Alternatively, the composition can be emulsified with oily substances before being introduced into the underground formations. In another example, the composition can be used to change the surface wetting properties (wettability) of a given surface downhole (for example, a fracture surface in a formation matrix or an underground formation). The specific use of the composition and its performance can depend on the conditions that exist or are expected to exist downhole.

[0041] In a specific example, the composition of the present disclosure can be used in combination with enhanced oil recovery (EOR) operations. When used in combination with EOR operations, the organic carbonate of the present disclosure can change the surface wettability in the underground formation to promote the recovery of hydrocarbons therefrom. For example, by changing the surface wettability of the underground formation, the release of hydrocarbons from the formation matrix can occur more easily and / or the hydrocarbons can be moved to the production well more easily. The above can be promoted by a variety of mechanisms, such as including oil swelling, viscosity reduction and wettability changes. The above process is generally referred to as the third stage of hydrocarbon production, wherein one or more chemical or physical interactions are changed in the underground formation using an injection fluid to promote production. The third stage of hydrocarbon production is usually used after the initial production caused by natural reservoir pressurization (primary production) or induced reservoir pressurization (secondary production) has been exhausted. Those of ordinary skill in the art will be familiar with other details about enhanced oil recovery technology.

[0042] Embodiments disclosed herein include:

[0043] A. Compositions formed from alkyl glycosides. The composition comprises: an organic carbonate comprising an anionic moiety, wherein the anionic moiety is a carbonate ester reaction product of an alkyl glycoside.

[0044] B. A method for treating a subterranean formation. The method comprises: providing the composition of A; and introducing the composition into a subterranean formation.

[0045] C. A method for forming an organic carbonate of an alkyl glycoside, comprising: contacting an alkyl glycoside with high-pressure carbon dioxide in the presence of a non-nucleophilic base; obtaining an organic carbonate comprising a cation portion containing a protonated non-nucleophilic base and an anion portion as a carbonate reaction product of the alkyl glycoside.

[0046] Embodiments A, B, and C may include one or more of the following additional embodiments in any combination.

[0047] Element 1: wherein the alkyl glycoside is an alkyl polyglycoside.

[0048] Element 2: wherein the alkyl polysaccharide comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in the form of a salt, and the terminal monosaccharide unit of the at least two monosaccharide units is alkylated.

[0049] Element 3: wherein the at least two monosaccharide units are linked by an α-1,4-glycosidic bond.

[0050] Element 4: wherein the organic carbonate comprises a cationic portion, and the cationic portion comprises a non-nucleophilic base in a protonated form.

[0051] Element 5: wherein the pK of the non-nucleophilic base isa is about 10 or more.

[0052] Element 6: wherein the non-nucleophilic base comprises an amidine.

[0053] Element 7: wherein the cationic portion comprises a protonated form of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU).

[0054] Element 8: wherein the alkyl glycoside comprises a terminal alkyl group containing about 4 to about 24 carbon atoms.

[0055] Element 9: wherein the carbonate reaction product comprises an organic carbonate group in the form of a salt located at the primary alcohol position of at least one monosaccharide unit of the alkyl glycoside.

[0056] Element 10: wherein the composition further comprises an aqueous fluid in which the organic carbonate is dissolved.

[0057] Element 11: wherein the aqueous fluid comprises at least one salt.

[0058] Element 12: wherein the composition is introduced into a subterranean formation in conjunction with an enhanced hydrocarbon recovery process.

[0059] Element 13: wherein the composition contacts a saline fluid in an underground formation, the aqueous fluid comprises at least one salt, or any combination of the above.

[0060] Element 14: wherein the method further comprises contacting the composition with an oily substance in an underground formation; and emulsifying the oily substance in the aqueous fluid in the presence of the organic carbonate.

[0061] Element 15: wherein, when the composition is introduced into an underground formation, the composition is emulsified with an oily substance.

[0062] Element 16: wherein the contacting is carried out in an aprotic organic solvent under heating.

[0063] Element 17: wherein the heating is carried out at a temperature of up to about 100°C.

[0064] Element 18: wherein the high pressure is about 3 atm to about 5 atm.

[0065] As non-limiting examples, exemplary combinations suitable for A, B, and C include, but are not limited to: 1 and 2, and 3; 1 and 2, and 4, 5, 6, or 7; 1 and 2, and 8; 1 and 2, and 9; 1 and 2, and 10; 1 and 2, and 10 and 11; 3, and 4, 5, 6, or 7; 3 and 8; 3 and 9; 3 and 10; 3, 10, and 11; 4, 5, 6, or 7, and 8; 4, 5, 6, or 7, and 9; 4, 5, 6, or 7 and 10; 4, 5, 6, or 7, and 10 and 11; 8 and 9; 8 and 10; 8, 10, and 11; 9 and 10; and 9-11. With respect to B and C, any of the foregoing may be further combined with one or more of 12-18. Other exemplary combinations suitable for B include, but are not limited to, 12 and 13; 12 and 14; 12 and 15; and 13 and 14. Other exemplary combinations suitable for C include, but are not limited to, 16 and 17; 16 and 18; 17 and 18; and 16-18.

[0066] The present disclosure also relates to the following non-limiting sub-items:

[0067] Sub-item 1. A composition comprising:

[0068] An organic carbonate comprising an anionic moiety which is a carbonate reaction product of an alkyl glycoside.

[0069] Sub-item 2. The composition according to sub-item 1, wherein the alkyl glycoside is an alkyl polyglycoside.

[0070] Subitem 3. The composition according to subitem 2, wherein the alkyl polysaccharide comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in salt form, and the terminal monosaccharide unit of the at least two monosaccharide units is alkylated.

[0071] Item 4. The composition according to item 3, wherein the at least two monosaccharide units are linked by an α-1,4-glycosidic bond.

[0072] Subitem 5. The composition of any one of Subitems 1 to 4, wherein the organic carbonate comprises a cationic portion comprising a non-nucleophilic base in a protonated form.

[0073] Sub-item 6. The composition of sub-item 5, wherein the pK of the non-nucleophilic base is a is about 10 or more.

[0074] Subitem 7. The composition of subitem 5 or 6, wherein the non-nucleophilic base comprises an amidine.

[0075] Subitem 8. The composition of any one of Subitems 5 to 7, wherein the cationic moiety comprises a protonated form of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU).

[0076] Subitem 9. The composition of any one of subitems 1 to 8, wherein the alkyl glycoside comprises a terminal alkyl group containing from about 4 to about 24 carbon atoms.

[0077] Subitem 10. The composition of any one of Subitems 1 to 9, wherein the carbonate reaction product comprises an organic carbonate group in salt form located at the primary alcohol position of at least one monosaccharide unit of the alkyl glycoside.

[0078] Sub-item 11. The composition according to any one of sub-items 1 to 10, further comprising:

[0079] An aqueous fluid having the organic carbonate dissolved therein.

[0080] Sub-item 12. A method comprising:

[0081] Providing the composition according to item 11; and

[0082] The composition is introduced into a subterranean formation.

[0083] Subitem 13. The method of subitem 12, wherein the composition is introduced into the subterranean formation in conjunction with an enhanced hydrocarbon recovery process.

[0084] Subitem 14. The method of subitem 12 or 13, wherein the composition contacts a saline fluid in a subterranean formation, the aqueous fluid comprising at least one salt, or any combination thereof.

[0085] Sub-item 15. The method according to any one of sub-items 12 to 14, further comprising:

[0086] contacting the composition with an oleaginous substance in a subterranean formation; and

[0087] An oily substance is emulsified in an aqueous fluid in the presence of the organic carbonate.

[0088] Subclause 16. The method of any one of subclauses 12 to 14, wherein the composition is emulsified with an oleaginous substance when the composition is introduced into a subterranean formation.

[0089] Sub-item 17. A method comprising:

[0090] contacting the alkyl glycoside with high pressure carbon dioxide in the presence of a non-nucleophilic base; and

[0091] An organic carbonate is obtained, the organic carbonate comprising a cationic portion comprising a non-nucleophilic base in a protonated form and an anionic portion being a carbonate reaction product of an alkyl glycoside.

[0092] Item 18. The method according to Item 17, wherein the contacting is performed in an aprotic organic solvent under heating.

[0093] Subitem 19. The method according to subitem 18, wherein the heating is performed at a temperature of up to about 100°C.

[0094] Subitem 20. The method of any one of subitems 17 to 19, wherein the elevated pressure is from about 3 atm to about 5 atm.

[0095] Subitem 21. The method according to any one of subitems 17 to 20, wherein the alkyl glycoside is an alkyl polyglycoside.

[0096] Sub-item 22. The method according to sub-item 21, wherein the alkyl polysaccharide comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in salt form, and the terminal monosaccharide unit of the at least two monosaccharide units is alkylated.

[0097] Item 23. The method according to item 22, wherein the at least two monosaccharide units are linked by an α-1,4-glycosidic bond.

[0098] Sub-item 24. The method according to any one of sub-items 17 to 23, wherein the pK of the non-nucleophilic base is a is about 10 or more.

[0099] Subitem 25. The method of any one of subitems 17 to 24, wherein the non-nucleophilic base cation comprises an amidine.

[0100] Subitem 26. The method of any one of subitems 17 to 25, wherein the cationic moiety comprises a protonated form of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU).

[0101] Subitem 27. The method of any one of subitems 17 to 26, wherein the alkyl glycoside comprises a terminal alkyl group containing from about 4 to about 24 carbon atoms.

[0102] Subitem 28. The method of any one of subitems 17 to 27, wherein the carbonate reaction product comprises an organic carbonate group in salt form located at a primary alcohol position of at least one monosaccharide unit of the alkyl glycoside.

[0103] Sub-item 29. The method according to any one of sub-items 17 to 28, further comprising:

[0104] The carbonate reaction product is dissolved in an aqueous fluid.

[0105] Subitem 30. The method of subitem 29, wherein the aqueous fluid comprises at least one salt.

[0106] In order to facilitate a better understanding of the disclosure herein, the following examples of various representative embodiments are given. The following examples should not be construed as limiting or defining the scope of the present invention.

[0107] Example

[0108] Reaction of alkyl polysaccharide with CO2 in the presence of DBU. Commercially available alkyl polysaccharide (APG1214, Shanghai Fakai Chemical Co., Ltd., 2-3 glucose units, C 12 -C 14 Alkyl) was freeze-dried and used after removing the residual moisture. In a glass reaction vessel, 5 grams of alkyl polyglycoside were dissolved in 100 mL of dimethyl sulfoxide, and a molar excess (3.1-4.3 g) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) was added. The reaction mixture was sealed and heated at a temperature of 50-60°C while stirring. Carbon dioxide was then introduced into the sealed reaction vessel until a pressure of 3-5 bar was reached. The reaction was continued for several hours under heating conditions, during which a white solid was formed. The white solid was then separated by centrifugation. The product was redissolved in deionized water and the product was isolated by freeze drying.

[0109] Spectroscopic Characterization. The carbonate reaction products were characterized by infrared and UV-visible spectroscopy. Figure 1 The FTIR spectra of the reaction products of alkyl polyglycoside and alkyl polyglycoside carbonate are shown in Figure 2. Compared with the alkyl polyglycoside raw material, the reaction product has a -1 There is a peak near 2600cm, which is broadened and contains a new fine structure. The new peak is characteristic of the introduction of carbonate groups. -1 Nearby, the peak associated with adsorbed CO2 is also evident. Figure 2 1 is a comparative UV-visible spectrum of the alkyl polyglycoside and the alkyl polyglycoside carbonate reaction product. As shown in the figure, the UV-visible absorbance increases after the carbonate reaction product is formed. The increase in UV-visible absorbance is believed to be caused by the DBU cation.

[0110] Salt tolerance. The carbonate reaction product was dissolved at a concentration of 0.2 wt% in a solution containing 57,670 ppm total dissolved solids (18,300 ppm Na + 、650ppm Ca2+ 、2,110ppm Mg 2+ 、4,290ppm SO4 2- 、32,200ppm Cl - 、120ppmHCO3 - ) in high-salinity water. The solution remained transparent at both 25°C and 90°C, indicating that no precipitation occurred in the presence of high salt concentrations.

[0111] Emulsification properties. An aqueous solution of the carbonate reaction product in high-salinity water was mixed with crude oil in a 1:1 volume ratio and emulsified by shaking the mixture by hand. An oil-in-water emulsion was readily formed under agitation, and after standing for 30 minutes or less, the emulsion separated into discrete oil and water phases. In contrast, an emulsion formed solely from high-salinity water and crude oil did not undergo demulsification within the same time frame.

[0112] Interfacial tension: The interfacial tension of the high-salinity aqueous solution was tested using a spinning drop tensiometer (SVT 20, Dataphysics) at a rotation speed of 5000 rpm. Figure 3 is a graph of the interfacial tension of the alkyl polyglycoside and alkyl polyglycoside carbonate reaction products as a function of time. As shown, the interfacial tension of the alkyl polyglycoside carbonate reaction product is about 10 times lower than the interfacial tension of the parent alkyl polyglycoside. In addition, the interfacial tension of the carbonate reaction product remains relatively constant over time, unlike the parent alkyl polyglycoside, which shows an increase in interfacial tension over time.

[0113] The directional terms used herein are for convention and reference purposes only and should not be construed as limiting. However, it should be recognized that these terms may be used with reference to an operator or user. Therefore, no limitation is implied or inferred. In addition, the use of ordinal numbers (e.g., first, second, third, etc.) is for distinction rather than counting. For example, the use of "third" does not mean that there must be a corresponding "first" or "second". In addition, if used herein, the term "coupled" or "coupled to" or "connected" or "connected to" or "attached" or "attached to" may indicate the establishment of a direct or indirect connection, and is not limited to any one unless explicitly mentioned as such.

[0114] Although the present disclosure has described several exemplary embodiments, it will be understood by those skilled in the art that various changes may be made and that equivalents may be substituted for its elements without departing from the spirit and scope of the present invention. In addition, it will be understood by those skilled in the art that many modifications will adapt specific instruments, situations or materials to embodiments of the present invention without departing from the essential scope of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed, or the best mode for implementing the present invention, but the present invention will include all embodiments falling within the scope of the appended claims. In addition, references in the appended claims to a device or system or a component of a device or system that is suitable for, arranged to, capable of, configured to, enabled to, operable to, or operated to perform a specific function include the device, system or component, whether or not it or the specific function is activated, turned on or unlocked, as long as the device, system or component is so debugged, arranged, capable of, configured to, capable of, operable or operated.

[0115] While the present disclosure has been described with reference to a limited number of embodiments, those skilled in the art having benefit of this disclosure will appreciate that other embodiments can be designed which do not depart from the scope of the present disclosure as described herein. Accordingly, the scope of the present disclosure should be limited only by the claims appended hereto.

[0116] All documents described herein are incorporated herein by reference for the purpose of all jurisdictions allowing such practice, including any priority documents and / or test procedures, as long as they do not contradict this article. As is apparent from the general description and specific embodiments above, although the form of the present disclosure has been illustrated and described, various modifications can be made without departing from the thought and scope of the present disclosure. Therefore, it is not intended to limit the present disclosure thereby. For example, the composition described herein may not contain any component or composition not explicitly listed or disclosed herein. Any method may lack any step not listed or disclosed herein. Similarly, the term "including" is considered to be synonymous with the term "comprising". As long as there is a transitional phrase "including" before a method, composition, element or element group, it should be understood that we also contemplate that the same composition or element group has a transitional phrase "substantially consisting of...", "consisting of...", "selected from a group consisting of..." or "is", before the narration of the composition, element or multiple elements, and vice versa.

[0117] Unless otherwise indicated, all numbers expressing quantities of ingredients, properties such as molecular weight, reaction conditions, and the like used in the specification and the associated claims are to be understood as being modified in all instances by the term "about". Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and the appended claims are approximations that may vary depending upon the desired properties sought to be obtained by one or more of the embodiments described herein. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

Claims

1. A composition comprising: An organic carbonate comprising an anionic moiety which is a carbonate reaction product of an alkyl glycoside.

2. The composition according to claim 1, wherein The alkyl glycoside is an alkyl polyglycoside.

3. The composition according to claim 2, wherein The alkyl polyglycoside comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in salt form, and the terminal monosaccharide unit of the at least two monosaccharide units is alkylated.

4. The composition according to claim 3, wherein The at least two monosaccharide units are linked via an α-1,4-glycosidic bond.

5. The composition according to claim 1, wherein The organic carbonate includes a cationic portion that includes a non-nucleophilic base in a protonated form.

6. The composition according to claim 5, wherein The pK of the non-nucleophilic base a is about 10 or more.

7. The composition according to claim 5, wherein Such non-nucleophilic bases include amidines.

8. The composition according to claim 7, wherein The cationic moiety includes 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) in protonated form.

9. The composition according to claim 1, wherein The alkyl glycosides include a terminal alkyl group containing from about 4 to about 24 carbon atoms.

10. The composition according to claim 1, wherein The carbonate reaction product includes an organic carbonate group in salt form located at the primary alcohol position of at least one monosaccharide unit of the alkyl glycoside.

11. The composition according to claim 1, further comprising: An aqueous fluid having the organic carbonate dissolved therein.

12. A method comprising: Providing the composition of claim 11; as well as The composition is introduced into a subterranean formation.

13. The method according to claim 12, wherein: The composition is introduced into the subterranean formation in conjunction with an enhanced hydrocarbon recovery process.

14. The method according to claim 12, wherein: The composition contacts a saline fluid in the subterranean formation, the aqueous fluid comprising at least one salt, or any combination thereof.

15. The method according to claim 12, further comprising: contacting the composition with an oleaginous substance in the underground formation; as well as The oily substance is emulsified in the aqueous fluid in the presence of the organic carbonate.

16. The method according to claim 12, wherein: When the composition is introduced into the underground formation, the composition is emulsified with an oily substance.

17. A method comprising: contacting the alkyl glycoside with high pressure carbon dioxide in the presence of a non-nucleophilic base; as well as An organic carbonate is obtained, the organic carbonate comprising a cationic portion and an anionic portion, the cationic portion comprising the non-nucleophilic base in a protonated form, the anionic portion being a carbonate reaction product of the alkyl glycoside.

18. The method according to claim 17, wherein: The contacting is performed in an aprotic organic solvent under heating.

19. The method according to claim 18, wherein: The heating is carried out at a temperature of up to about 100°C.

20. The method according to claim 17, wherein: The high pressure is about 3 atm to about 5 atm.

21. The method according to claim 17, wherein: The alkyl glycoside is an alkyl polyglycoside.

22. The method according to claim 21, wherein: The alkyl polyglycoside comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in salt form, and the terminal monosaccharide unit of the at least two monosaccharide units is alkylated.

23. The method according to claim 22, wherein: The at least two monosaccharide units are linked via an α-1,4-glycosidic bond.

24. The method of claim 17, wherein: The non-nucleophilic base cations include amidines.

25. The method according to claim 24, wherein: The cationic moiety includes 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) in protonated form.

26. The method of claim 17, wherein: The alkyl glycosides include a terminal alkyl group containing from about 4 to about 24 carbon atoms.

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