Surfactant compositions derived from waste streams, and methods

Abstract

Compositions, such as surfactant compositions, and methods of forming compositions, such as surfactant compositions, which may include a gemini surfactant, said surfactants being ammonium compounds of formulae (I) to (VII). The methods may use a starting material from a stream generated by another process.

Description

FI2156b Attorney Docket No.92230-0341 SURFACTANT COMPOSITIONS DERIVED FROM WASTE STREAMS, AND METHODS

[0001] Technical Field

[0002] The present disclosure generally relates to surfactants, including surfactants derived from one or more waste streams, compositions that include one or more surfactants, and methods for producing surfactants.

[0003] Background

[0004] Gemini surfactants usually include two surfactant molecules chemically bonded together by a spacer. The two terminal hydrocarbon tails of gemini surfactants can be short (e.g., 5 to 15 carbon atoms) or long (e.g., 16 to 30 carbon atoms); the two polar head groups of a gemini surfactant can be cationic, anionic, or nonionic; and the spacer can be short (e.g., 1 to 3 carbon atoms), long (e.g., 4 to 6 carbon atoms), flexible, or rigid, and / or may contain one or more heteroatoms (e.g., nitrogen, oxygen, sulfur, phosphorus, etc.).

[0005] Moreover, components of a gemini surfactant may or may not be symmetrically disposed about the center of the spacer. Some gemini surfactants can self- assemble at much lower concentrations, and / or have improved surface activity compared to conventional surfactants. Due to these options and features, gemini surfactants can be tailored for a number of applications, and / or useful in a number of applications.

[0006] For example, gemini surfactants may be useful in catalysis and adsorption applications, as new synthetic vectors for gene transfection, in analytical separations, in solubilization processes, in nanoscale technologies, in biotechnologies, in enhanced oil recovery, and / or as additives in a number of products, such as paint.

[0007] There remains a need for methods of producing surfactants, including gemini surfactants, that are cost-effective, use starting materials that are readily available and / or inexpensive, or a combination thereof. There also remains a need for compositions, including surfactant compositions, that include a gemini surfactant.

[0008] Brief Summary

[0009] Provided herein are compositions, which may include a gemini surfactant, and methods of forming compositions, such as surfactant compositions, which may use 1 51382236.1FI2156b Attorney Docket No.92230-0341 readily available and / or relatively inexpensive starting materials, such as starting materials that are present in a waste stream from other processes.

[0010] In one aspect, methods of forming compositions, such as surfactant compositions, are provided. In some embodiments, the methods include (i) providing a starting material that includes 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl 3-[2- (dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl methacrylate, or a combination thereof; ;material. The providing of the starting material may include providing a stream, such as a waste stream, and separating from the stream at least a portion of the 2- (dimethylamino)ethyl 3-methoxy-2-methylpropanoate, at least a portion of the methyl 3- [2-(dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2- (dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl methacrylate, or a combination thereof.

[0011] In another aspect, compositions, such as surfactant compositions, are provided. In some embodiments, the compositions include a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), or a combination thereof, and, additionally or alternatively, any one or more products obtained by a hydrolysis, such as an ester hydrolysis, of the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), or the combination thereof: 2 51382236.1FI2156b Attorney Docket No.92230-0341 ;FI2156b Attorney Docket No.92230-0341 wherein R1, R2, R3, R4, R5, R6, R7, and R8are independently selected from the group consisting of a C5-C30hydrocarbyl, formula (a), formula (b), and formula (c);; wherein R9and R10,11 12hydrocarbyl, and R and R , independently, are a C1-C30 hydrocarbyl.

[0012] Additional aspects will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the aspects described herein. The advantages described herein may be realized and attained by means of the elements and combinations particularly pointed out in the listing of embodiments and the appended claims. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive.

[0013] Brief Description of the Drawings

[0014] FIG.1 is a plot of surface tension in deionized water at about 24 °C versus concentration (mmol) for an embodiment of a surfactant composition.

[0015] FIG.2 is a plot of surface tension in deionized water at about 24 °C versus concentration (ppm) for an embodiment of a surfactant composition. 4 51382236.1FI2156b Attorney Docket No.92230-0341

[0016] Detailed Description

[0017] Provided herein are methods of making compositions and compositions, such as surfactant compositions.

[0018] Compositions

[0019] In some embodiments, the compositions include a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), or a combination thereof, and, additionally or alternatively, any one or more products obtained by a hydrolysis, such as an ester hydrolysis, of the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), or the combination thereof:FI2156b Attorney Docket No.92230-0341 CH3H3C CH3;consisting of a C5-C30 hydrocarbyl, formula (a), formula (b), and formula (c); ; wherein R9and R10,hydrocarbyl, and R11and R12, independently, are a C1-C30hydrocarbyl.

[0020] When the formulas or compounds depicted herein include a positively charged moiety or atom, such as a positively charged quaternary nitrogen atom, the formulas or compounds may include any counteranion. In some embodiments, the 6 51382236.1FI2156b Attorney Docket No.92230-0341 compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), and / or the compound of formula (VII) include a counteranion corresponding to each quaternary nitrogen atom. The counteranions may include inorganic ions, such as a halide ion, or organic ions, such as an alkyl sulfonate or an aryl sulfonate.

[0021] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, independently, are a C1-C30hydrocarbyl, C6-C30hydrocarbyl, C6-C28hydrocarbyl, C6-C26hydrocarbyl¸ C6-C24 hydrocarbyl¸ C10-C24 hydrocarbyl¸ C10-C20 hydrocarbyl¸ C14-C24 hydrocarbyl¸ C10-C17hydrocarbyl, or a C18-C24hydrocarbyl. The number of carbon atoms of a hydrocarbyl may be selected to impart one or more desirable characteristics to a composition or a component thereof. When the compositions described herein include a compound of formula (V), R5and R6may be the same or different. For example, (i) R5may be a branched dodecyl group, and R6may be a linear dodecyl group; (ii) R5may be a branched dodecyl group, and R6may be a branched hexyl group; (iii) R5and R6may be identical linear decyl groups; etc.

[0022] In some embodiments, the compositions include a compound of formula (V). The compound of formula (V) may have a structure according to formula (Va): ;according to formula (Vb):

[0024] In some embodiments, the compound of formula (V) has a structure according to formula (Vc): 7 51382236.1FI2156b Attorney Docket No.92230-0341according to formula (Vd):a , , formula (Vc), and formula (Vd), non-linear C5-C30 hydrocarbyl groups are described herein, and may be included in any of these formulas.

[0026] In some embodiments, the compositions include any one or more of the compounds described herein, such as a compound of formula (V), and the compositions have a critical micelle concentration that is at least 6 times, at least 8 times, at least 10 times, at least 12 times, or at least 14 times less than a comparative critical micelle concentration of a comparative composition that includes a single-cation surfactant. For comparison purposes, the critical micelle concentration is measured at a temperature of about 20 °C to about 25 °C.

[0027] In some embodiments, the compositions include any one or more of the compounds described herein, such as a compound of formula (V), and, with regard to corrosion inhibition or biological inhibition, the compositions have a minimal inhibitory concentration that is at least 6 times, at least 8 times, at least 10 times, at least 12 times, or at least 14 times less than a comparative minimal inhibitory concentration of a comparative composition that includes a single-cation surfactant.

[0028] A compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), or a combination thereof may be present at any concentration in the compositions provided herein. For example, a compound of 8 51382236.1FI2156b Attorney Docket No.92230-0341 formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), the hydrolysis products thereof, or a combination thereof may be present in the composition at a concentration of at least 50 %, at least 60 %, at least 70 %, at least 80 %, at least 90 %, at least 95 %, or at least 99 %, by weight, based on the weight of the composition. Therefore, if a composition having a weight of 100 units includes 30 units of a compound of formula (III) and 20 units a compound of formula (IV), then the composition includes 50 %, by weight, of the combination of compounds of formulas (III) and (IV). As a further example, a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), the hydrolysis products thereof, or a combination thereof may be present in a composition at a concentration of about 0.01 % to about 25 %, about 0.01 % to about 20 %, about 0.01 % to about 15 %, about 0.01 % to about 10 %, about 0.01 % to about 7.5 %, about 0.01 % to about 5 %, about 0.01 % to about 3 %, about 0.01 % to about 2 %, or about 0.01 % to about 1 %, by weight, based on the weight of the composition.

[0029] The compositions described herein may be a detergent, a cosmetic, a personal care product, a coating (e.g., a paint), a biocide, a pharmaceutical formulation, an anti- corrosion agent, an enhanced oil recovery fluid, a fabric softener, a leveling agent, a drying agent, a solubilizer, an emulsifier, a dispersant, a foaming agent, a mining fluid, a waste water treatment fluid, an anti-foaming agent, an anti-static agent, or a combination thereof. The compositions described herein may be an additive for a detergent, a cosmetic, a personal care product, a coating (e.g., a paint), a biocide, a pharmaceutical formulation, an anti-corrosion agent, an enhanced oil recovery fluid, a fabric softener, a leveling agent, a drying agent, a solubilizer, an emulsifier, a dispersant, a foaming agent, a mining fluid, a waste water treatment fluid, an anti-foaming agent, an anti-static agent, or a combination thereof. Other uses and applications, however, are envisioned.

[0030] Methods of Forming Compositions

[0031] Also provided herein are methods of forming compositions, such as surfactant compositions. In some embodiments, the methods include providing a starting material that includes 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, methyl 3- [2-(dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl 3-[2- 9 51382236.1FI2156b Attorney Docket No.92230-0341 (dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl methacrylate, or a combination thereof: .from any source. In some embodiments, the providing of the starting material includes (i) providing a stream that includes 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl 3-[2- (dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl methacrylate, or a combination thereof; ;(ii) separating from the stream at least a portion of the 2-(dimethylamino)ethyl 3-methoxy- 2-methylpropanoate, at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2- methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl 3-[2- (dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2- (dimethylamino)ethyl methacrylate, or a combination thereof. The separating of compounds from the stream may be achieved using any known technique. In some 10 51382236.1FI2156b Attorney Docket No.92230-0341 embodiments, the one or more compounds is separated from a stream via distillation or rectification.

[0033] The stream that includes 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2- (dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2- (dimethylamino)ethyl methacrylate, or a combination thereof may be a waste stream. The waste stream may be from a process that produces a polymerizable monomer or a precursor thereof, such as a methacrylate monomer.

[0034] In some embodiments, the methods also include converting at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, at least a portion of the 2- (dimethylamino)ethyl methacrylate, or a combination thereof to 2-(dimethylamino)ethyl 3- [2-(dimethylamino)ethoxy]-2-methyhlpropanoate.

[0035] The 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2- methyhlpropanoate may then be processed as described herein, such as by contacting it with an alkylation agent, subjecting it to hydrolysis, or a combination thereof. The converting of the at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2- methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl methacrylate, or a combination thereof to 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2- methyhlpropanoate may be achieved in any manner. In some embodiments, the converting of the at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2- methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl methacrylate, or a combination thereof to 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2- methyhlpropanoate includes contacting (i) the at least a portion of the methyl 3-[2- (dimethylamino)ethoxy]-2-methylpropanoate, the at least a portion of the 2- (dimethylamino)ethyl 3-methoxy-2-methylpropanoate, the at least a portion of the 2- (dimethylamino)ethyl methacrylate, or a combination thereof, and (ii) a base. The base may be present at any effective amount, such as a catalytic amount. The base may include any of those known in the art, such as a hydroxide, e.g., NaOH, KOH, etc. The contacting may occur in a liquid. The liquid may be any liquid that does not undesirably impact the conversion. The liquid may include an aqueous liquid and / or an organic liquid. The 11 51382236.1FI2156b Attorney Docket No.92230-0341 liquid may include an alcohol, such as an amino alcohol. An “amino alcohol” is a compound that includes at least one alcohol functional group and at least one amine; an example of an amino alcohol is 2-(dimethylamino)ethan-1-ol.

[0036] The streams, such as waste streams, that may be subjected to the methods described herein may include various concentrations of one or more of the starting materials and other components. In some embodiments, methyl 3-[2- (dimethylamino)ethoxy]-2-methylpropanoate is present in the stream at a concentration of about 1 % to about 20 %, about 8 % to about 20 %, or about 10 % to about 15 %, by weight. In some embodiments, 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate is present in the stream at a concentration of about 1 % to about 60 %, about 10 % to about 40 %, about 15 % to about 30 %, or about 20 % to about 25 %, by weight. In some embodiments, 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate is present in the stream at a concentration of about 5 % to about 40 %, about 10 % to about 40%, about 20 % to about 40 %, or about 25 % to about 35 %, by weight. In some embodiments, 2-(dimethylamino)ethyl methacrylate is present in the stream at a concentration of about 1 % to about 25 %, about 10 % to about 20 %, or about 12 % to about 18 %, by weight.

[0037] The starting materials may be contacted with an alkylation agent to form an alkylated material. The alkylation agent may include any of those known in the art, and generally is a compound that is capable of covalently bonding a hydrocarbyl group, directly or via a functional group (such as an amide or ester), to a starting material to form a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), or a combination thereof. In some embodiments, the alkylation agent includes – ,FI2156b Attorney Docket No.92230-0341 ,, or a combination thereof; atom, such as Cl, Br, or I; and wherein R, Ra, Rb, Rc, Rd, Re, Rf,Rg, and independently, are a C1-C30hydrocarbyl, such as a C5-C30hydrocarbyl. In some embodiments, R, Ra, Rb, Rc, Rd, Re, Rf, Rg, and Rh, independently, are a C6-C30 hydrocarbyl, C6-C28hydrocarbyl, C6-C26hydrocarbyl¸ C6-C24hydrocarbyl¸ C10-C24hydrocarbyl¸ C10-C20 hydrocarbyl¸ C14-C24 hydrocarbyl¸ C10-C17 hydrocarbyl, or a C18-C24 hydrocarbyl. R, Ra, Rb, Rc, Rd, Re, Rf, Rg, and Rhmay be selected to impart a desirable property to a composition, such as a desirable hydrophilic-lipophilic balance (HLB).

[0038] A starting material generally may be contacted with any amount of an alkylation agent. In some embodiments, a starting material is contacted with an amount of moles of the alkylation agent that equals or exceeds an amount of moles of tertiary nitrogen atoms in the starting material. In some embodiments, a starting material is contacted with an amount of moles of the alkylation agent that is less than an amount of moles of tertiary nitrogen atoms in the starting material. An amount of alkylation agent that is used may be selected to impart a desirable property to a composition, such as a desirable hydrophilic-lipophilic balance (HLB).

[0039] An alkylated material may be subjected to further reaction, such as a hydrolysis reaction to produce a hydrolyzed material. The hydrolysis reaction may be an ester hydrolysis reaction, which may cleave an ester functional group as depicted in the following scheme:

[0040] include contacting an alkylated material and water, wherein the water has a pH less than 7 or 13 51382236.1FI2156b Attorney Docket No.92230-0341 greater than 7, and the pH is effective to achieve hydrolysis, such as ester hydrolysis. Therefore, a hydrolysis reaction may be a base catalyzed hydrolysis reaction or an acid catalyzed hydrolysis reaction. In some embodiments, the alkylated material includes a compound of formula (V), a compound of formula (Va), a compound of formula (Vb), a compound of formula (Vc), a compound of formula (Vd), or a combination thereof;wherein x, y, and z, independently, are 4 to 29; and R’ and R” , independently, are a C1- C30 hydrocarbyl; R3and R4, independently, are a C5-C30 hydrocarbyl; and wherein the hydrolyzed material includes a compound of formula (V’), a compound of formula (V”), a compound of formula (Va’), a compound of formula (Va”), a compound of formula (Vb’), a compound of formula (Vb”), a compound of formula (Vc’), a compound of formula 14 51382236.1FI2156b Attorney Docket No.92230-0341 (Vc”), a compound of formula (Vd’), a compound of formula (Vd”), or a combination thereof; ; ;FI2156b Attorney Docket No.92230-0341 ;that (i) a substituent or variable at a particular location may be the same or different for each molecule a formula (e.g., (i) a compound of formula (I) may include two molecules of formula (I), with each molecule having the same or a different C5-C30 hydrocarbyl selected for R1; or (ii) two differently labeled substituents or variables selected from the same group of substituents may be the same or different (e.g., R5and R6of formula (V) may both be selected from “a C10-C24hydrocarbyl”, and the C10-C24hydrocarbyls selected for R5and R6may be the same or different).

[0042] The phrases “C1-C30hydrocarbyl,” “C10-C24hydrocarbyl”, and the like, as used herein, generally refer to aliphatic, aryl, or arylalkyl groups containing 1 to 30 carbon atoms, or 10 to 24 carbon atoms, respectively, including substituted derivatives thereof. Examples of aliphatic groups, in each instance, include, but are not limited to, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkadienyl group, a cyclic group, and the like, and includes all substituted, unsubstituted, branched, and / or linear analogs or derivatives thereof, in each instance having, for example, 1 to 30 total carbon atoms or 10 to 24 total carbon atoms for a “C1-C30 hydrocarbyl ” and “C10-C24hydrocarbyl”, respectively. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, isobutyl, pentyl, hexyl, isohexyl, heptyl, 4,4-dimethylpentyl, octyl, 2,2,4-trimethylpentyl, nonyl, decyl, undecyl, and dodecyl. Cycloalkyl moieties may be monocyclic or multicyclic, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl, including any heteroatom substituted derivative thereof. Additional examples of alkyl moieties have linear, branched and / or cyclic portions (e.g., 1-ethyl-4-methyl-cyclohexyl). 16 51382236.1FI2156b Attorney Docket No.92230-0341 Representative alkenyl moieties include vinyl, allyl, 1-butenyl, 2-butenyl, isobutylenyl, 1- pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 2-methyl-2-butenyl, 2,3-dimethyl-2-butenyl, 1- hexenyl, 2-hexenyl, 3-hexenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3- octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 1-decenyl, 2-decenyl, and 3-decenyl. Representative alkynyl moieties include acetylenyl, propynyl, 1-butynyl, 2-butynyl, 1- pentynyl, 2-pentynyl, 3-methyl-1-butynyl, 4-pentynyl, 1-hexynyl, 2-hexynyl, 5-hexynyl, 1-heptynyl, 2-heptynyl, 6-heptynyl, 1-octynyl, 2-octynyl, 7-octynyl, 1-nonynyl, 2- nonynyl, 8-nonynyl, 1-decynyl, 2-decynyl and 9-decynyl. Examples of aryl or arylalkyl moieties include, but are not limited to, anthracenyl, azulenyl, biphenyl, fluorenyl, indan, indenyl, naphthyl, phenanthrenyl, phenyl, 1,2,3,4-tetrahydro-naphthalene, anthracenyl, tolyl, xylyl, mesityl, benzyl, and the like, including any heteroatom substituted derivative thereof.

[0043] Unless otherwise indicated, the term "substituted," when used to describe a chemical structure or moiety, refers to a derivative of that structure or moiety wherein (i) a multi-valent non-carbon atom (e.g., oxygen, nitrogen, sulfur, phosphorus, etc.) is bonded to one or more carbon atoms of the chemical structure or moiety (e.g., a “substituted” C4 hydrocarbyl may include, but is not limited to, a pyrimidinyl moiety, a pyridinyl moiety, a dioxanyl moiety, a diethyl ether moiety, a methyl propionate moiety, an N,N- dimethylacetamide moiety, a butoxy moiety, etc., and a “substituted” aryl C12 hydrocarbyl may include, but is not limited to, an oxydibenzene moiety, a benzophenone moiety, etc.) or (ii) one or more of its hydrogen atoms (e.g., chlorobenzene may be characterized generally as an aryl C6hydrocarbyl “substituted” with a chlorine atom) is substituted with a chemical moiety or functional group such as acyl, alcohol, alkoxy, alkanoyloxy, alkoxycarbonyl, alkenyl, alkyl (e.g., methyl, ethyl, propyl, t-butyl), alkynyl, alkylcarbonyloxy (-OC(O)alkyl), amide (-C(O)NH-alkyl- or -alkylNHC(O)alkyl), primary, secondary, and tertiary amino (such as alkylamino, arylamino, arylalkylamino), aryl, arylalkyl, aryloxy, azo, azido, carbamoyl (-NHC(O)O-alkyl- or -OC(O)NH-alkyl), carbamyl (e.g., CONH2, as well as CONH-alkyl, CONH-aryl, and CONH-arylalkyl), carboxyl, carboxylic acid, cyano, cycloalkyl, cycloalkenyl, ester, ether (e.g., methoxy, ethoxy), halo, haloalkyl (e.g., -CCl3, -CF3, -C(CF3)3), haloalkoxy, trihalomethanesulfonyl, trihalomethanesulfonamido, heteroalkyl, heterocycloalkyl, heteroaryl, heteroarylalkyl, isocyanate, isothiocyanate, nitrile, nitro, oxo, phosphodiester, silyl, sulfide, sulfonamido (e.g., SO2NH2), sulfone, sulfenyl, sulfinyl, sulfonyl (including alkylsulfonyl, arylsulfonyl 17 51382236.1FI2156b Attorney Docket No.92230-0341 and arylalkylsulfonyl), sulfoxide, thiocarbonyl, thiocarbamyl, thiocyanato, thiol (e.g., sulfhydryl, thioether) or urea (-NHCONH-alkyl-).

[0044] All referenced publications are incorporated herein by reference in their entirety. Furthermore, where a definition or use of a term in a reference, which is incorporated by reference herein, is inconsistent or contrary to the definition of that term provided herein, the definition of that term provided herein applies and the definition of that term in the reference does not apply.

[0045] While certain aspects of conventional technologies have been discussed to facilitate disclosure of various embodiments, applicants in no way disclaim these technical aspects, and it is contemplated that the present disclosure may encompass one or more of the conventional technical aspects discussed herein.

[0046] The present disclosure may address one or more of the problems and deficiencies of known methods and processes. However, it is contemplated that various embodiments may prove useful in addressing other problems and deficiencies in a number of technical areas. Therefore, the present disclosure should not necessarily be construed as limited to addressing any of the particular problems or deficiencies discussed herein.

[0047] In this specification, where a document, act or item of knowledge is referred to or discussed, this reference or discussion is not an admission that the document, act or item of knowledge or any combination thereof was at the priority date, publicly available, known to the public, part of common general knowledge, or otherwise constitutes prior art under the applicable statutory provisions; or is known to be relevant to an attempt to solve any problem with which this specification is concerned.

[0048] In the descriptions provided herein, the terms “includes,” “is,” “containing,” “having,” and “comprises” are used in an open-ended fashion, and thus should be interpreted to mean “including, but not limited to.” When compositions or methods are claimed or described in terms of “comprising” various steps or components, the compositions or methods can also “consist essentially of” or “consist of” the various steps or components, unless stated otherwise.

[0049] The terms “a,” “an,” and “the” are intended to include plural alternatives, e.g., at least one. For instance, the disclosure of “a stream”, “an alkylation agent”, and the like, is meant to encompass one, or mixtures or combinations of more than one stream, alkylation agent, and the like, unless otherwise specified. 18 51382236.1FI2156b Attorney Docket No.92230-0341

[0050] Various numerical ranges may be disclosed herein. When Applicant discloses or claims a range of any type, Applicant’s intent is to disclose or claim individually each possible number that such a range could reasonably encompass, including end points of the range as well as any sub-ranges and combinations of sub- ranges encompassed therein, unless otherwise specified. Moreover, all numerical end points of ranges disclosed herein are approximate. As a representative example, Applicant discloses, in some embodiments, that one of several “R” groups may be a C10-C24hydrocarbyl. This range should be interpreted as encompassing a C10 hydrocarbyl and a C24hydrocarbyl, and the further encompasses each of a C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, and C23 hydrocarbyl, including any ranges and sub-ranges between any of these values.

[0051] As used herein, the term “about” means plus or minus 10 % of the numerical value of the number with which it is being used.

[0052] Examples

[0053] The present disclosure is further illustrated by the following examples, which are not to be construed in any way as imposing limitations upon the scope thereof. On the contrary, it is to be clearly understood that resort may be had to various other aspects, embodiments, modifications, and equivalents thereof which, after reading the description herein, may suggest themselves to one of ordinary skill in the art without departing from the spirit of the present disclosure or the scope of the appended claims. Thus, other aspects of this disclosure will be apparent to those skilled in the art from consideration of the specification and practice of the aspects disclosed herein.

[0054] Although the following examples are directed to results obtained from a waste stream of a process that produces acrylates, the same procedures may be applied to waste streams from processes that produce methacrylates, or the procedures, if needed, may be modified, without undue experimentation, to accommodate waste streams from processes that produce methacrylates.

[0055] Example 1 – Preparation of an Embodiment of a Surfactant

[0056] A round bottom reaction flask was charged with 8.35 g (about 35.5 mmol) of 2-(dimethylamino)ethyl 3-(2-(dimethylamino)ethoxy)propanoate, and 18.72 g (about 70 mmol) of dodecyl 2-chloroacetate (n = 9). 19 51382236.1FI2156b Attorney Docket No.92230-0341

[0057] The reaction mixture was stirred at 50 °C for one hour, and this temperature was maintained for 20 hours, without stirring. The reaction likely proceeded according to the following scheme (n = 9):(oxy))bis(ethane-2,1- diyl))bis(2-(dodecyloxy)-N,N-dimethyl-2-oxoethan-1-aminium) dichloride was a colorless waxy solid.

[0059] The product was characterized with1H NMR, and the surface tension of the product was determined in deionized water at about 24 °C at various concentrations. These results are provided at FIG.1 and FIG.2. The critical micelle concentration of the product was about 0.07 mmol to about 0.1 mmol.

[0060] Example 2 – Preparation of an Embodiment of a Surfactant

[0061] A round bottom reaction flask was charged with 11.02 g (about 47 mmol) of 2-(dimethylamino)ethyl 3-(2-(dimethylamino)ethoxy)propanoate, and 36.92 g (about 110 mmol) of 1-bromooctadecane, and 50 mL acetone.

[0062] The reaction mixture was stirred and refluxed for 72 hours at 70 °C. The resulting reaction mixture was a colorless crystal dispersion. The precipitate was filtered, washed with 100 mL of acetone, and refluxed in 100 mL of acetone.

[0063] The reaction likely proceeded according to the following scheme (n = 16):washed with 100 mL of acetone, and dried at room temperature in vacuo.

[0065] The reaction yield was about 75.7 %. The product was N,N'-(((1-oxopropane- 1,3-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(N,N-dimethyloctadecan-1-aminium) dibromide. The product was characterized with1H NMR.

[0066] Example 3 – Preparation of an Embodiment of a Surfactant 20 51382236.1FI2156b Attorney Docket No.92230-0341

[0067] A round bottom reaction flask was charged with 12.07 g (about 52 mmol) of 2-(dimethylamino)ethyl 3-(2-(dimethylamino)ethoxy)propanoate, and 35.0 g (about 100 mmol) of octadecyl 2-chloroacetate.

[0068] The reaction mixture was stirred at 50 °C for one hour, and this temperature was maintained for 20 hours without stirring. The reaction likely proceeded according to the following scheme (n = 15):bis(oxy))bis(ethane-2,1- diyl))bis(2-(octadecyloxy)-N,N-dimethyl-2-oxoethan-1-aminium) dichloride, and was a colorless brittle solid.

[0070] A portion of the product (about 5.12 g) was extracted twice with 50 mL of acetonitrile, while stirring at 50 °C. The first extraction lasted 3 hours, and the second extraction occurred over night. The product, after extraction, was a colorless powder, which was dried under reduced pressure (about 20 mbar) at room temperature for 5 hours. The products were characterized with1H NMR.

[0071] Example 4 – Conversion of Mixed Monoamines

[0072] In this example, the following abbreviations are used – Abbreviation Compound21 51382236.1FI2156b Attorney Docket No.92230-0341 a-MEPAME (anti-MEPAME)p , obtained as a distillation fraction of a waste stream. The starting material included the following monoamines: Monoamine wt%

[0074] In this example, 78.6 g of the foregoing mixed monoamines were placed in a round bottom flask, and 2.5 g of potassium hydroxide in 37.5 g of DMAE were added to the round bottom flask in one portion. The 78.6 g of the mixed monoamines included the following amounts of the monoamines: 22 51382236.1FI2156b Attorney Docket No.92230-0341 Monoamine Mass (g) Moles DMAE 1.88 0.021140 to about 50 mbar at 40 °C for about 2 hours. The reactions of this example were believed to proceed according to the following scheme:adding 8 g of AMBERLYST®15 ion exchange resin (DuPont de Nemours, Inc., USA) in H± form. After the ion exchange resin was separated by filtration, the product was analyzed by gas chromatography-flame ionization detection (GC-FID).

[0077] The results of the analysis are depicted at the following table: Component Starting Material (wt%) Product (wt%)23 51382236.1FI2156b Attorney Docket No.92230-0341

[0078] The data of this table demonstrates the successful conversion of a portion of the monoamines to DMETOADA, because the wt% of ADAME, MEPAME, and a- MEPTAME was less in the Product (due to their conversion and the addition of DMAE), and the wt% of DMETOADA was greater in the Product, despite the addition of DMAE. In summary, the data revealed that the conversion of monoamines to DMETOADAMA, in this example, was greater than 60%.

[0079] Embodiments

[0080] The following is a listing of non-limiting embodiments.

[0081] Embodiment 1. A composition, such as a surfactant composition, comprising, consisting essentially of, or consisting of a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), or a combination thereof, and, additionally or alternatively, any one or more products obtained by a hydrolysis, such as an ester hydrolysis, of the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), or the combination thereof:24 51382236.1FI2156b Attorney Docket No.92230-0341the group consisting of a C5-C30 hydrocarbyl, formula (a), and formula (b), formula (c); 25 51382236.1FI2156b Attorney Docket No.92230-0341

[0083] such as a C5-C30 hydrocarbyl, and are a and / or R1, R2, R3, R4, R5, R6, R7, and R8, independently, are derived from one or more of the following alkylation agents – , 51382236.1FI2156b Attorney Docket No.92230-0341

[0084] wherein Hal is a halogen atom, such as Cl, Br, or I; and wherein R, Ra, Rb, Rc, Rd, Re, Rf, Rg, and Rh, independently, are a C1-C30 hydrocarbyl.

[0085] Embodiment 2. The composition of Embodiment 1, wherein the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI) the compound of formula (VII), or the combination thereof comprise a counteranion, such as a counteranion corresponding to each quaternary nitrogen atom.

[0086] Embodiment 3. The composition of any of the preceding Embodiments, wherein the counteranion comprises an inorganic ion, for example, a halide ion, such as Cl- or Br-.

[0087] Embodiment 4. The composition of any of the preceding Embodiments, wherein the counteranion comprises an organic ion, such as an alkyl sulfonate (for example, methane sulfonate), or an aryl sulfonate (for example, toluene sulfonate).

[0088] Embodiment 5. The composition of any of the preceding Embodiments, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, Ra, Rb, Rc, Rd, Re, Rf, Rg, and Rh, independently, are a C6-C30 hydrocarbyl, a C6-C28 hydrocarbyl, a C6-C26 hydrocarbyl¸ a C6-C24 hydrocarbyl¸ a C10-C24 hydrocarbyl¸ a C10-C20 hydrocarbyl¸ a C14-C24 hydrocarbyl¸ a C10-C17 hydrocarbyl, or a C18-C24 hydrocarbyl.

[0089] Embodiment 6. The composition of any of the preceding Embodiments, wherein the compound of formula (V) has a structure according to formula (Va):wherein x, independently, is 4 to 29.

[0090] Embodiment 7. The composition of any of the preceding Embodiments, wherein the compound of formula (V) has a structure according to formula (Vb):27 51382236.1FI2156b Attorney Docket No.92230-0341

[0091] Embodiment 8. The composition of any of the preceding Embodiments, wherein the compound of formula (V) has a structure according to formula (Vc):are a

[0092] Embodiment 9. The composition of any of the preceding Embodiments, wherein the composition comprises, consists essentially of, or consists of –

[0093] (i) the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), one or more hydrolysis products thereof, or the combination thereof; or

[0094] (ii) the compound of formula (V), one or more hydrolysis products thereof, or a combination thereof; or

[0095] (iii) the compound of formula (Va), the compound of formula (Vb), the compound of formula (Vc), the compound of formula (Vd), one or more hydrolysis products thereof, or a combination thereof; and

[0096] the composition has a critical micelle concentration that is at least 6 times, at least 8 times, at least 10 times, at least 12 times, or at least 14 times less than a comparative critical micelle concentration of a comparative composition comprising a single-cation surfactant.

[0097] Embodiment 10. The composition of any of the preceding Embodiments, wherein, with regard to corrosion inhibition or biological inhibition, the composition comprises, consists essentially of, or consists of – 28 51382236.1FI2156b Attorney Docket No.92230-0341

[0098] (i) the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), one or more hydrolysis products thereof, or the combination thereof; or

[0099] (ii) the compound of formula (V), one or more hydrolysis products thereof, or a combination thereof; or

[0100] (iii) the compound of formula (Va), the compound of formula (Vb), the compound of formula (Vc), the compound of formula (Vd), one or more hydrolysis products thereof, or a combination thereof; and

[0101] the composition has a minimal inhibitory concentration that is at least 6 times, at least 8 times, at least 10 times, at least 12 times, or at least 14 times less than a comparative minimal inhibitory concentration of a comparative composition comprising a single-cation surfactant.

[0102] Embodiment 11. The composition of any of the preceding Embodiments, wherein the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), the one or more hydrolysis products thereof, or the combination thereof is present in the composition at a concentration of at least 50 %, at least 60 %, at least 70 %, at least 80 %, at least 90 %, at least 95 %, or at least 99 %, by weight, based on the weight of the composition.

[0103] Embodiment 12. The composition of any of the preceding Embodiments, wherein the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), the one or more hydrolysis products thereof, or the combination thereof is present in the composition at a concentration of about 0.01 % to about 25 %, about 0.01 % to about 20 %, about 0.01 % to about 15 %, about 0.01 % to about 10 %, about 0.01 % to about 7.5 %, about 0.01 % to about 5 %, about 0.01 % to about 3 %, about 0.01 % to about 2 %, or about 0.01 % to about 1 %, by weight, based on the weight of the composition.

[0104] Embodiment 13. The composition of any of the preceding Embodiments, wherein the composition is—or is an additive for—a detergent, a cosmetic, a personal care product, a coating (e.g., a paint), a biocide, a pharmaceutical formulation, an anti- corrosion agent, an enhanced oil recovery fluid, a fabric softener, a leveling agent, a 29 51382236.1FI2156b Attorney Docket No.92230-0341 drying agent, a solubilizer, an emulsifier, a dispersant, a foaming agent, a mining fluid, a waste water treatment fluid, an anti-foaming agent, an anti-static agent, or a combination thereof.

[0105] Embodiment 14. A method of forming a composition, such as a surfactant composition, the method comprising (i) providing a starting material comprising, consisting essentially of, or consisting of 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2- (dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2- (dimethylamino)ethyl methacrylate, or a combination thereof: analkylated material.

[0107] Embodiment 15. The method of Embodiment 14, wherein the alkylation agent comprises, consists essentially of, or consists of – ,FI2156b Attorney Docket No.92230-0341 , or a combination thereof; is a halogen atom, such as Cl, Br, or I; and wherein R, Ra, Rb,independently, are a C1-C30 hydrocarbyl, such as a C5-C30 hydrocarbyl.

[0109] Embodiment 16. The method of any of the preceding Embodiments, wherein R, Ra, Rb, Rc, Rd, Re, Rf, Rg, and Rh, independently, are a C6-C30hydrocarbyl, a C6-C28hydrocarbyl, a C6-C26 hydrocarbyl¸ a C6-C24 hydrocarbyl¸ a C10-C24 hydrocarbyl¸ a C10- C20hydrocarbyl¸ a C14-C24hydrocarbyl¸ a C10-C17hydrocarbyl, or a C18-C24hydrocarbyl and R4is C1-C30 hydrocarbyl.

[0110] Embodiment 17. The method of any of the preceding Embodiments, wherein the starting material is contacted with an amount of moles of the alkylation agent that (i) equals or exceeds an amount of moles of tertiary nitrogen atoms in the starting material, or (ii) is less than an amount of moles of tertiary nitrogen atoms in the starting material.

[0111] Embodiment 18. The method of any of Embodiments 14 to 17, wherein the providing of the starting material comprises (i) providing a stream that comprises, consists essentially of, or consists of 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl 3-[2- (dimethylamino)ethoxy]-2-methylpropanoate, 2-(dimethylamino)ethyl methacrylate, or a combination thereof;least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, at least a portion 31 51382236.1FI2156b Attorney Docket No.92230-0341 of the methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl methacrylate, or a combination thereof.

[0113] Embodiment 19. The method of Embodiment 18, wherein the stream is a waste stream.

[0114] Embodiment 20. The method of any of the preceding Embodiments, wherein the waste stream is from a process that produces a polymerizable monomer or a precursor thereof, such as a methacrylate monomer.

[0115] Embodiment 21. The method of any of the preceding Embodiments, further comprising converting at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2- methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl methacrylate, or a combination thereof to 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2- methyhlpropanoate; wherein, optionally, the converting of the at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, the at least a portion of the 2- (dimethylamino)ethyl 3-methoxy-2-methylpropanoate, the at least a portion of the 2- (dimethylamino)ethyl methacrylate, or the combination thereof to 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methyhlpropanoate comprises, consists essentially of, or consists of contacting (i) the at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]- 2-methylpropanoate, the at least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, the at least a portion of the 2-(dimethylamino)ethyl methacrylate, or the combination thereof, and (ii) a base (e.g., KOH), such as a catalytic amount of the base, wherein, optionally, the contacting occurs in a liquid, which may be an aqueous liquid and / or an organic liquid, wherein, optionally, the liquid comprises an alcohol, such as an amino alcohol (e.g., 2-(dimethylamino)ethan-1-ol); and wherein, optionally, at least 40 mol%, at least 50 mol%, at least 60 mol%, at least 70 mol%, or at least 80 mol% of the methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, at least 40 mol%, at least 50 mol%, at least 60 mol%, at least 70 mol%, or at least 80 mol% of the 2- (dimethylamino)ethyl 3-methoxy-2-methylpropanoate, and / or at least 40 mol%, at least 50 mol%, at least 60 mol%, at least 70 mol%, or at least 80 mol% of the 2- (dimethylamino)ethyl methacrylate is converted to 2-(dimethylamino)ethyl 3-[2- (dimethylamino)ethoxy]-2-methyhlpropanoate. 32 51382236.1FI2156b Attorney Docket No.92230-0341

[0116] Embodiment 22. The method of any of the preceding Embodiments, wherein (i) the methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate is present in the stream at a concentration of about 1 % to about 20 %, about 8 % to about 20 %, or about 10 % to about 15 %, by weight; (ii) the 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate is present in the stream at a concentration of about 1 % to about 60 %, about 10 % to about 40 %, about 15 % to about 30 %, or about 20 % to about 25 %, by weight; (iii) the 2- (dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate is present in the stream at a concentration of about 5 % to about 40 %, about 10 % to about 40%, about 20 % to about 40 %, or about 25 % to about 35 %, by weight; (iv) the 2-(dimethylamino)ethyl methacrylate is present in the stream at a concentration of about 1 % to about 25 %, about 10 % to about 20 %, or about 12 % to about 18 %, by weight; or (v) any combination thereof.

[0117] Embodiment 23. The method of any of the preceding Embodiments, further comprising subjecting the alkylated material to a hydrolysis reaction to produce a hydrolyzed material.

[0118] Embodiment 24. The method of any of the preceding Embodiments, wherein the hydrolysis reaction comprises contacting the alkylated material and water, wherein the water has a pH less than 7 or greater than 7, and the pH is effective to achieve ester hydrolysis.

[0119] Embodiment 25. The method of any of the preceding Embodiments, wherein the alkylated material comprises, consists essentially of, or consists of a compound of formula (V), a compound of formula (Va), a compound of formula (Vb), a compound of formula (Vc), a compound of formula (Vd), or a combination thereof; formula (V);33 51382236.1FI2156b Attorney Docket No.92230-0341

[0120] wherein x, y, and z, independently, are 4 to 29; and R’ and R”, independently, are a C1-C30hydrocarbyl; R3and R4, independently, are a C1-C30hydrocarbyl, such as a C5-C30 hydrocarbyl.

[0121] Embodiment 26. The method of any of the preceding Embodiments, wherein the hydrolyzed material (or the one or more hydrolysis products of the compositions of the preceding Embodiments) comprises, consists essentially of, or consists of a compound of formula (V’), a compound of formula (V”), a compound of formula (Va’), a compound of formula (Va”), a compound of formula (Vb’), a compound of formula (Vb”), a compound of formula (Vc’), a compound of formula (Vc”), a compound of formula (Vd’), a compound of formula (Vd”), or a combination thereof; ;FI2156b Attorney Docket No.92230-0341 ; ;FI2156b Attorney Docket No.92230-0341 formula (Vd”); are 4 to 29; and R’ and R” ,are a and R4, independently, are a C5-C30 hydrocarbyl.

[0123] Embodiment 27. The method of any of the preceding Embodiments, wherein a product of the method comprises, consists essentially of, or consists of a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), the compound of formula (VI), the compound of formula (VII), one or more hydrolysis products of the compound of formula (I), one or more hydrolysis products of the compound of formula (II), one or more hydrolysis products of the compound of formula (III), one or more hydrolysis products of the compound of formula (IV), one or more hydrolysis products of the compound of formula (V), one or more hydrolysis products of the compound of formula (VI), one or more hydrolysis products of the compound of formula (VII), or a combination thereof, as defined by any of the preceding Embodiments. 36 51382236.1

Claims

FI2156b Attorney Docket No.92230-0341 We claim – 1. A method of forming a composition, the method comprising: (i) providing a starting material comprising 2-(dimethylamino)ethyl 3- methoxy-2-methylpropanoate, methyl 3-[2-(dimethylamino)ethoxy]-2- methylpropanoate, 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2- methylpropanoate, 2-(dimethylamino)ethyl methacrylate, or a combination thereof,alkylated material.

2. The method claim 1, wherein the providing of the starting material comprises: (i) providing a stream comprising 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2- (dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, 2- (dimethylamino)ethyl methacrylate, or a combination thereof; ; and(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, at least a portion of the 37 51382236.1FI2156b Attorney Docket No.92230-0341 methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, at least a portion of the 2-(dimethylamino)ethyl methacrylate, or a combination thereof.

3. The method of claim 2, wherein the stream is from a process that produces a polymerizable monomer or a precursor thereof.

4. The method of claim 2, further comprising converting the at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, the at least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, the at least a portion of the 2-(dimethylamino)ethyl methacrylate, or a combination thereof to 2- (dimethylamino)ethyl 3-[2-(dimethylamino)ethoxy]-2-methyhlpropanoate; wherein the converting comprises contacting (i) a base and (ii) the at least a portion of the methyl 3-[2-(dimethylamino)ethoxy]-2-methylpropanoate, the at least a portion of the 2-(dimethylamino)ethyl 3-methoxy-2-methylpropanoate, the at least a portion of the 2-(dimethylamino)ethyl methacrylate, or the combination thereof; and wherein at least 40 mol% of the methyl 3-[2-(dimethylamino)ethoxy]-2- methylpropanoate, at least 40 mol% of the 2-(dimethylamino)ethyl 3-methoxy-2- methylpropanoate, and / or at least 40 mol% of the 2-(dimethylamino)ethyl methacrylate is converted to 2-(dimethylamino)ethyl 3-[2- (dimethylamino)ethoxy]-2-methyhlpropanoate.

5. The method of claim 1, wherein the alkylation agent comprises – ,FI2156b Attorney Docket No.92230-0341 a combination thereof;independently, are a C1-C30 hydrocarbyl.

6. The method of claim 1, further comprising subjecting the alkylated material to a hydrolysis reaction to produce a hydrolyzed material.

7. The method of claim 6, wherein the alkylated material comprises a compound of formula (V), and the hydrolyzed material comprises a compound of formula (V’) and a compound of formula (V”): ;wherein R3and R4are independently selected from the group consisting of a C5-C30 hydrocarbyl, formula (a), and formula (b), formula (c); 39 51382236.1FI2156b Attorney Docket No.92230-0341 are a C5-C30 hydrocarbyl, and R11andR12, are a 8. A composition comprising a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), or a combination thereof: CH3O R140 51382236.1FI2156b Attorney Docket No.92230-0341the group consisting of a C5-C30 hydrocarbyl, formula (a), and formula (b), formula (c); 41 51382236.1FI2156b Attorney Docket No.92230-0341 are a C5-C30 hydrocarbyl, and R11andR12, are a 9. The composition of claim 8, wherein the composition comprises the compound of formula (V), wherein the compound of formula (V) has a structure according to formula (Va), formula (Vb), formula (Vc), or formula (Vd):FI2156b Attorney Docket No.92230-0341independently, are a C1-C30 hydrocarbyl.

10. The composition of claim 8, wherein the composition comprises the compound of formula (V), one or more hydrolysis products of the compound of formula (V), or a combination thereof, and the composition has a critical micelle concentration that is at least 6 times less than a comparative critical micelle concentration of a comparative composition comprising a single-cation surfactant.

11. The composition of claim 8, wherein the composition comprises the compound of formula (V), one or more hydrolysis products of the compound of formula (V), or a combination thereof, and the composition has a critical micelle concentration that is at least 10 times less than a comparative critical micelle concentration of a comparative composition comprising a single-cation surfactant.

12. The composition of claim 8, wherein the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), the compound of formula (VI), the compound of formula (VII), one or more hydrolysis products thereof, or a combination thereof is present in the composition at a concentration of at least 50 %, by weight, based on the weight of the composition.

13. The composition of claim 12, wherein the composition is an additive for a cosmetic, a personal care product, a coating, a biocide, a pharmaceutical formulation, an anti-corrosion agent, or an enhanced oil recovery fluid, a fabric softener, a leveling agent, a drying agent, a solubilizer, an emulsifier, a dispersant, a foaming agent, a mining fluid, a waste water treatment fluid, an anti-foaming agent, or an anti-static agent. 43 51382236.1FI2156b Attorney Docket No.92230-0341 14. The composition of claim 8, wherein the compound of formula (I), the compound of formula (II), the compound of formula (III), the compound of formula (IV), the compound of formula (V), one or more hydrolysis products thereof, or a combination thereof is present in the composition at a concentration of about 0.01 % to about 15 %, by weight, based on the weight of the composition.

15. The composition of claim 14, wherein the composition is a detergent, a cosmetic, a personal care product, a coating, a biocide, a pharmaceutical formulation, an anti- corrosion agent, an enhanced oil recovery fluid, a fabric softener, a leveling agent, a drying agent, a solubilizer, an emulsifier, a dispersant, a foaming agent, a mining fluid, a waste water treatment fluid, an anti-foaming agent, or an anti-static agent. 44 51382236.1

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