N-acylaminoalkanesulfonate surfactants and their derivatives

Abstract

The surfactant composition comprises greater than 75% by weight of an N-acylaminoalkanesulfonate of Formula (I). The surfactant composition is substantially free of solvent and NaCl. A method for preparing a mixture comprising an N-acylaminoalkanesulfonate surfactant includes combining (a) an aminoalkanesulfonic acid of Formula (II) or (b) an anhydrous alkali salt of an aminoalkanesulfonic acid of Formula (II), an anhydrous base, and an aliphatic alkyl ester of Formula (III) to form a mixture comprising the N-acylaminoalkanesulfonate of Formula (I). The method further includes increasing the temperature of the mixture to about 190°C or less, preferably about 170°C or less, and more preferably about 160°C or less to form a reaction mixture, and continuously removing the alkyl alcohol from the reaction mixture. [Formula 1] TIFF2025540177000024.tif18128

Description

[Technical Field]

[0001] The present disclosure relates generally to N-acylaminoalkanesulfonate surfactants and derivatives, and in certain embodiments, to N-acylaminoalkanesulfonate surfactant compositions having reduced amounts of impurities. [Background technology]

[0002] Surfactants are the single most important cleaning ingredient in cleaning products. Environmental regulations, consumer habits, and practices are forcing new developments in the surfactant industry to produce lower cost, higher performance, and environmentally friendly products.

[0003] Surfactants are key ingredients that play an important role in various applications and consumer products, such as detergents, hard surface cleaners, fabric softeners, body washes, face washes, shampoo conditioners, conditioning shampoos, and other surfactant-based compositions. Many catalogs and patents describe surfactant options that are too expensive to use. High costs are often due to the starting materials used to make such surfactants, inefficient reaction schemes, and / or complex methods required for their manufacture to meet specific quality attributes. Therefore, there is a need for new methods for producing surfactant compositions containing minimal impurities or additives at low cost.

[0004] N-acyltaurate, or N-acyltauride (and other amino acid-based) surfactants as named by others, can be commercially prepared from the corresponding fatty acid chlorides and amino acids using Schotten Baumann chemistry as shown in Equation 1.

[0005] [ka]

[0006] This amidation reaction is typically carried out in water, although the use of mixed water-solvent systems has been reported. Typically, the resulting sodium N-acylaminoalkanesulfonate surfactant is obtained in the form of an aqueous composition containing 20-30% active material, always along with high levels of undesirable inorganic salts (NaCl). The latter can be removed via an additional post-reaction step, which can add significant cost and process complexity. This surfactant preparation method is expensive and requires the preparation of fatty acid chlorides using chlorinating agents such as phosphorus trichloride (PCl3), phosphorus pentachloride (PCl5), thionyl chloride (SOCl2), oxalyl chloride (COCl2), or phosgene (a toxic gas). These chlorinating agents can be highly reactive and toxic, requiring highly specialized handling and metallurgy. Furthermore, depending on the specific chemistry and process used, the separation of fatty acid chlorides from by-products and the catalysts used has been challenging. Therefore, the product may contain undesirable impurities that can be carried over to the synthesis of the corresponding surfactant.

[0007] The preparation of N-acyltaurates has also been reported via the direct condensation of carboxylic acids with alkali salts of 2-aminoalkanesulfonic acids, as shown in Equation 2. However, this reaction requires the removal of water, high temperatures (190-240°C), and the use of an inert atmosphere. This direct amidation reaction can be carried out in the presence of catalysts such as zinc oxide, hypophosphorous acid, or boric acid, which remain in the surfactant mixture. Decomposition by-products have been reported, resulting in poor product yields and unacceptable product discoloration and odor. Typically, the carboxylic acid is used in a 30 or more molar excess relative to taurine. To produce fatty acid-free N-acyltaurates via this chemical approach, the crude reaction mixture is subjected to additional purification steps, such as distillation, extraction, recrystallization, or a combination thereof.

[0008] [ka]

[0009] Fatty alkyl esters have also been used as starting materials. According to another method, fatty alkyl esters are reacted with taurine in the presence of a polyol solvent, such as glycerin or propylene glycol. The relative molar ratio of polyol to amino compound ranged from about 8:1 to about 1:1. In the primary example included, the resulting product contained 34% glycerol, which remains in the surfactant mixture, making it undesirable for many applications. Summary of the Invention [Problem to be solved by the invention]

[0010] In summary, N-acylaminoalkanesulfonate surfactants made using these methods tend to contain high levels of undesirable by-products, such as salts (NaCl), or solvents, such as methanol, glycerol, and propylene glycol.Therefore, there is a need for N-acylaminoalkanesulfonate surfactant compositions that are made under atmospheric conditions and that are produced with low percentages of by-products and low levels of solvents or additives. [Means for solving the problem]

[0011] The present disclosure provides a surfactant composition comprising greater than 75% by weight of the surfactant composition of an N-acylaminoalkanesulfonate of formula (I),

[0012] [ka] In the formula, R is C5 to C 21The present disclosure seeks to solve one or more of these needs by providing a surfactant composition wherein R1 is an alkyl substituent, R1 represents H or a C1-C4 alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen, wherein the surfactant composition is substantially free of solvent and NaCl. The present disclosure also relates to surfactant compositions that are solid or aqueous liquid compositions.

[0013] The present disclosure further provides a method for preparing a mixture comprising an N-acylaminoalkanesulfonate surfactant, the method comprising: (a) an aminoalkanesulfonic acid of formula (II) or (b) an anhydrous alkali salt of an aminoalkanesulfonic acid of formula (II).

[0014] [ka] wherein R1 represents H or a C1-C4 alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen, an anhydrous base, and an aliphatic alkyl ester of formula (III):

[0015] [ka] (Wherein R is C5 to C 21 alkyl substituents, and R' is a C1 or higher alkyl substituent, preferably methyl), to form an N-acylaminoalkanesulfonate of formula (I):

[0016] [ka] (Wherein R is C5 to C 21wherein R represents H or a C1-C4 alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen; raising the temperature of the mixture to about 190°C or less, preferably to about 170°C or less, and more preferably to about 160°C or less to form a reaction mixture; and continuously removing the alkyl alcohol from the reaction mixture.

[0017] In another aspect, the present disclosure relates to a consumer product cleaning or personal care composition comprising from about 0.001 wt. % to about 99.999 wt. %, or from about 0.1 wt. % to about 80 wt. % of an N-acylaminoalkanesulfonate surfactant described herein, and from about 0.001 wt. % to about 99.999 wt. % of one or more additional cleaning components, or one or more additional personal care components, based on the total weight of the composition. DETAILED DESCRIPTION OF THE INVENTION

[0018] Features and advantages of the present disclosure will become apparent from the following description, including examples, which are intended to give a broad representation of the disclosure. Various modifications will become apparent to those skilled in the art from this specification and practice of the invention. The scope is not intended to be limited to the particular forms disclosed, but rather the present disclosure covers all modifications, equivalents, and alternatives falling within the spirit and scope of the invention as defined by the claims.

[0019] As used herein, the articles including "the," "a," and "an," when used in a claim or the specification, are understood to mean one or more of what is claimed or described.

[0020] As used herein, the terms "include", "includes" and "including" are meant to be open-ended.

[0021] As used herein, the terms "substantially free of" or "substantially free from" refer to either a complete absence or minimal amount of a component simply as an impurity or unintended by-product of another component. A composition "substantially free of" a component means that the composition contains less than about 0.5%, 0.25%, 0.1%, 0.05%, or 0.01%, or even 0%, by weight of the composition, of the component.

[0022] As used herein, the term "solid" includes granule, powder, flake, noodle, needle, extrudate, ribbon, bead, and pellet product forms that contain less than about 0.5%, 0.25%, 0.1%, 0.05%, or 0.01%, or even 0%, water by weight of the composition.

[0023] As used herein, "personal cleansing compositions" includes personal cleansing products such as shampoos, conditioners, conditioning shampoos, shower gels, liquid hand washes, facial cleansers, and other surfactant-based liquid compositions.

[0024] It should be understood that every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitations were expressly written herein. Every minimum numerical limitation given throughout this specification includes every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification will include every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were all expressly written herein.

[0025] In this description, all concentrations are by weight of the composition unless otherwise indicated.

[0026] The dimensions and values ​​disclosed herein should not be understood as being strictly limited to the exact numerical values ​​recited. Instead, unless otherwise indicated, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "about 40 mm."

[0027] N-Acylaminoalkanesulfonate surfactants The N-acylaminoalkanesulfonate surfactants disclosed herein have the following general formula (I):

[0028] [ka] In the formula, R is C5 to C 21 Preferably, R is an alkyl substituent, R represents H or a C1-C4 alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen. 7~17 It is an alkyl substituent. The alkyl substituent may be branched or unbranched.

[0029] The N-acylaminoalkanesulfonate surfactants described herein are typically not single compounds as suggested by their general formula (I), but rather comprise a mixture of several homologs having various chain lengths and molecular weights, as will be readily understood by those skilled in the art. The N-acylaminoalkanesulfonate surfactants described herein can be either saturated or unsaturated.

[0030] The N-acylaminoalkanesulfonate surfactant compositions of the present disclosure comprise at least 50 wt% N-acylaminoalkanesulfonate surfactant by weight of the surfactant composition. For example, the compositions may comprise 65-95 wt%, 70-95 wt%, 75-95 wt%, 80-95 wt%, 85-95 wt%, 90-95 wt%, 65-90 wt%, 70-90 wt%, 75-90 wt%, 80-90 wt%, 85-90 wt%, 65-85 wt%, 70-85 wt%, 75-85 wt%, 80-85 wt%, 65-80 wt%, 70-80 wt%, 75-80 wt%, 65-75 wt%, 70-75 wt%, or 65-70 wt% N-acylaminoalkanesulfonate surfactant by weight of the surfactant composition.

[0031] The surfactant composition may further comprise at least 5 wt%, preferably about 5 to about 15 wt%, more preferably about 8 to about 10 wt%, of an N-acyl-N-methylaminoalkanesulfonate surfactant by weight of the surfactant composition, such as 5-50 wt%, 5-35 wt%, 5-25 wt%, 5-20 wt%, 5-15 wt%, 5-12 wt%, 5-10 wt%, 5-8 wt%, 8-50 wt%, 8-35 wt%, 8-25 wt%, 8-20 wt%, 8-15 wt%, 8-12 wt%, 8-10 wt%, 10-50 wt%, 10-35 wt%, 10-25 wt%, 10 ... The composition may contain up to 20% by weight, 10 to 15% by weight, 10 to 12% by weight, 12 to 50% by weight, 12 to 35% by weight, 12 to 25% by weight, 12 to 20% by weight, 12 to 15% by weight, 15 to 50% by weight, 15 to 35% by weight, 15 to 25% by weight, 15 to 20% by weight, 20 to 50% by weight, 20 to 35% by weight, or 25 to 50% by weight of an N-acyl-N-methylaminoalkanesulfonate surfactant.

[0032] The N-acyl-N-methylaminoalkanesulfonate surfactant compositions of the present disclosure further comprise a fatty acid. The fatty acid can be present as a free fatty acid or in the form of a fatty acid soap. The amount in the composition can range from 1 to about 10% by weight, 2 to 7% by weight, or 3 to 5% by weight, including all values ​​within these ranges and any ranges created thereby.

[0033] Advantageously, the N-acylaminoalkanesulfonate surfactant compositions of the present disclosure may be substantially free of impurities, including water, salt (NaCl), polyol solvents, and methanol. The compositions of the present disclosure may contain less than 5%, less than 2%, less than 1%, less than 0.1%, or may be substantially free, or in some cases, free, of one or any combination of these impurities.

[0034] The present disclosure further encompasses concentrated compositions, often referred to as pastes, as well as solids such as powders and tablets, which can be combined with various adjunct ingredients (e.g., water) to make a variety of detergent products, including personal cleaning compositions and laundry detergents.

[0035] Typically, inorganic salts (NaCl) are added to cleaning formulations made with sulfated surfactants to thicken the product. Surprisingly, it has been found that adding inorganic salts to formulations that are substantially free of sulfated surfactants in the presence of cationic conditioning polymers, and / or using sulfate-free surfactants containing high levels of inorganic salts, can cause product instability due to the formation of gel-like surfactant-polymer complexes in the composition. Therefore, it is desirable to avoid or minimize the addition of NaCl to the formulation and / or use raw materials with low inorganic salt (NaCl) content. Commercially available sulfate-free surfactants, such as sodium methyl cocoyl taurate (cocoyl aminoalkane sulfonate) and other amino acid-based surfactants, typically contain high levels of inorganic salts, such as 5% or more. The use of these high salt (e.g., NaCl) raw materials in sulfate-free surfactant-based cleaning formulations can cause the formation of undesirable gel-like surfactant-polymer complexes in the product before use. The surfactant compositions described herein may enable the formulation of stable cleaning products that are substantially free of sulfated surfactants.

[0036] Method for Making N-Acylaminoalkanesulfonate Surfactants The method described herein allows for the preparation of N-acylaminoalkanesulfonate surfactants with low levels of impurities. The traditional Schotten-Baumann acid chloride route to N-acylaminoalkanesulfonate surfactants produces NaCl and other impurities, resulting in undesirable results. Furthermore, other reactions for making N-acylaminoalkanesulfonate surfactants use low-boiling point solvents and are carried out in sealed reactors under pressure rather than atmospheric conditions. High-pressure reaction conditions are inherently more dangerous, time-consuming, complicated, and expensive, making them undesirable. Others use high-boiling point solvents, such as polyols, glycerol, and propylene glycol, to carry out the reaction under atmospheric conditions, but these difficult-to-remove solvents remain with the surfactant.

[0037] A suitable method for preparing the N-acylaminoalkanesulfonate surfactants disclosed herein is to prepare (a) an aminoalkanesulfonic acid of formula (II), or (b) an anhydrous alkali salt of an aminoalkanesulfonic acid of formula (II).

[0038] [ka] wherein R1 represents H or a C1-C4 alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen, an anhydrous base, and an aliphatic alkyl ester of formula (III):

[0039] [ka] (Wherein R is C5 to C 21 alkyl substituents, and R' is a C1 or higher alkyl substituent, preferably methyl), to form an N-acylaminoalkanesulfonate of formula (I)

[0040] [ka] In the formula, R is C5 to C 21 is an alkyl substituent, R1 represents H or a C1-C4 alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen.

[0041] This method can prepare any of the surfactant compositions previously disclosed.

[0042] The reaction scheme for the formation of the surfactant composition is shown below.

[0043] Amidation Reaction

[0044] [ka]

[0045] Unexpectedly, during the preparation of sodium N-acyltaurate surfactants via the following reaction:

[0046] [ka] It has been discovered that sodium N-acyl-N-methyl taurate surfactants may also be formed as part of the surfactant composition.

[0047] [ka]

[0048] Under the reaction conditions, the following side reaction occurs at temperatures above 150°C, forming sodium N-acyl-N-methyl taurate in the system:

[0049] [ka] This is then believed to react with the fatty acid alkyl ester to form a useful and beneficial co-product, sodium N-acyl-N-methyl taurate surfactant, as shown in the reaction diagram below.

[0050] [ka]

[0051] The combining step may include preparing a suspension of the aminoalkanesulfonic acid salt of Formula (II) by adding the aliphatic alkyl ester of Formula (III) to the anhydrous alkali salt of the aminoalkanesulfonic acid of Formula (II) and contacting the suspension with anhydrous base to form a mixture. Because the amount of methanol provided by the catalytic amount of anhydrous base, sodium methoxide solution, or generated from the amidation reaction is not sufficient to overcome the lack of miscibility / compatibility between the alkali metal salt of the aminoalkanesulfonic acid and the aliphatic alkyl ester, adding a solvent to the process is desirable. The solvent may be the same as or different from methanol, but is preferably the same as that present in the anhydrous base and formed in the amidation reaction. Additionally or alternatively, the combining step may include combining the anhydrous base with the aliphatic alkyl ester of Formula (III) to form a premixture, and then adding (a) the aminoalkanesulfonic acid of Formula (II) or (b) the anhydrous alkali salt of the aminoalkanesulfonic acid of Formula (II) to the premixture to form a mixture. Additionally, or alternatively, the combining step may include preparing a blend of aminoalkanesulfonate salts of Formula (II) by adding an anhydrous base to the anhydrous alkali salt of an aminoalkanesulfonic acid of Formula (II) and contacting the blend with a fatty alkyl ester of Formula (III) to form a mixture. Additionally, or alternatively, the combining step may include preparing a blend of aminoalkanesulfonate salts of Formula (II) by adding an anhydrous base to the aminoalkanesulfonic acid of Formula (II) and contacting the blend with a fatty alkyl ester of Formula (III) to form a mixture.

[0052] When an aminoalkanesulfonic acid is contacted with an anhydrous base alone, a substance resembling a white solid aggregate may form. Therefore, it is believed that a lower conversion rate and yield to the N-acylaminoalkanesulfonate surfactant can be achieved by first adding the aminoalkanesulfonic acid to the anhydrous base (sodium methoxide solution) and then adding the fatty alkyl ester. Therefore, in this method, it is preferred to form the alkali metal salt of the aminoalkanesulfonic acid in situ by adding the aminoalkanesulfonic acid to a mixture of the anhydrous base and the fatty alkyl ester. Additionally or alternatively, this method may include adding the anhydrous base to a suspension of the aminoalkanesulfonic acid in the fatty alkyl ester (FAME). Without being bound by theory, this is advantageous because the resulting alkali metal salt of the aminoalkanesulfonic acid that forms is finely dispersed or soluble in the mixture containing the fatty alkyl ester.

[0053] The method may include adding an N-acylaminoalkanesulfonate surfactant to water to form a surfactant composition comprising greater than 20 wt%, preferably greater than 25 wt%, and more preferably greater than 30 wt% of the N-acylaminoalkanesulfonate surfactant by weight of the surfactant composition. The method may include adding an N-acylaminoalkanesulfonate surfactant to water to form a surfactant composition comprising greater than 20 wt%, preferably greater than 25 wt%, and more preferably greater than 30 wt% of the N-acylaminoalkanesulfonate surfactant by weight of the surfactant composition. The method may include adding an N-acylaminoalkanesulfonate surfactant to water to form a surfactant composition comprising greater than 20 wt%, preferably greater than 25 wt%, and more preferably greater than 30 wt%, of the N-acylaminoalkanesulfonate surfactant by weight of the surfactant composition. ~55wt%, 25~50wt%, 30~95wt%, 30~90wt%, 30~85wt%, 30~80wt%, 30~75wt%, 30~70wt%, 30~65wt%, 30~60wt%, 30~55wt%, 30~50wt%, 40~95wt%, 40~90wt%, 40~85wt%, 40~80wt%, 40~75wt%, 40~70wt%, 40~65wt%, 40~60wt%, 40~55wt%, 40~50wt%, 50~95wt%, 50~90wt %, 50~85wt%, 50~80wt%, 50~75wt%, 50~70wt%, 50~65wt%, 50~60wt%, 50~55wt%, 55~95wt%, 55~90wt%, 55~85wt%, 55~80wt%, 55~75 Weight%, 55~70% by weight, 55~65% by weight, 55~60% by weight, 60~95% by weight, 60~90% by weight, 60~85% by weight, 60~80% by weight, 60~75% by weight, 60~70% by weight, 60~65% by weight, 65~95% by weight, 65~ The composition may contain 90% by weight, 65 to 85% by weight, 65 to 80% by weight, 65 to 75% by weight, 65 to 70% by weight, 70 to 95% by weight, 70 to 90% by weight, 70 to 85% by weight, 70 to 80% by weight, 70 to 75% by weight, 75 to 95% by weight, 75 to 90% by weight, 75 to 85% by weight, 75 to 80% by weight, 80 to 95% by weight, 80 to 90% by weight, 80 to 85% by weight, 85 to 95% by weight, 85 to 90% by weight, or 90 to 95% by weight of an N-acylaminoalkanesulfonate surfactant.

[0054] The method may include increasing the temperature of the mixture to about 190° C. or less, preferably to about 170° C. or less, and more preferably to about 160° C. or less to form a reaction mixture. The increasing step may include increasing the temperature of the mixture to about 65° C. to about 190° C., or preferably to about 90° C. to about 160° C. The method may include continuously removing the alkyl alcohol from the reaction mixture.

[0055] (a) The aminoalkanesulfonic acid of formula (II) may include taurine (2-aminoethanesulfonic acid), homotaurine (3-amino-1-propanesulfonic acid), N-methyltaurine (2-methylaminoethanesulfonic acid), or a combination thereof. (b) The anhydrous alkali salt of the aminoalkanesulfonic acid of formula (II) may include sodium 2-aminoethanesulfonate, sodium N-methyltaurine, sodium 3-aminopropanesulfonate, sodium 3-(N-methylamino)propanesulfonate, and a combination thereof.

[0056] Suitable anhydrous bases for use include alkali metals such as sodium, lithium, and potassium; alloys of two or more alkali metals such as sodium-lithium alloys and sodium-potassium alloys; alkali metal hydrides, e.g., sodium, lithium, and potassium hydrides; and alkali metal alkoxides, particularly those containing from about 1 to about 4 carbon atoms, such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium n-propoxide, potassium n-propoxide, sodium isopropoxide, potassium isopropoxide, sodium butoxide, potassium butoxide, sodium isobutoxide, potassium isobutoxide, sodium sec-butoxide, potassium sec-butoxide, and potassium tert-butoxide. The alkoxides are available in solid form or as a solution in the alcohol from which the alkoxide was derived. The anhydrous base may comprise a C1-C4 alkoxide, preferably sodium methoxide, potassium methoxide, or a combination thereof, in a methanol solution.

[0057] The mixture may contain (a) about 1.00 to about 1.50 moles, preferably about 1.02 to about 1.20 moles, and more preferably about 1.05 to about 1.10 moles of anhydrous base per mole of the aminoalkanesulfonic acid of formula (II).The mixture may contain (b) about 0.01 to about 0.5 moles, preferably about 0.02 to about 0.2 moles, and more preferably about 0.05 to about 0.1 moles of anhydrous base per mole of the anhydrous alkali salt of the aminoalkanesulfonic acid of formula (II).

[0058] The relative molar amount of alkoxide added in step i) may be in the range of 1.00 to 1.50 moles, 1.02 to 1.20 moles, or 1.05 to 1.10 moles per mole of amino acid, including all values ​​within these ranges and any ranges derived therefrom. Any alkoxide not consumed in neutralization catalyzes the reaction between the amino acid salt and the fatty alkyl ester. Thus, in the methods described herein, the amount of alkoxide catalyst may be in the range of 2 to 20 mole percent or 5 to 10 mole percent, including all values ​​within these ranges and any ranges derived therefrom.

[0059] As used herein, the terms "fatty alkyl ester" and "fatty acid ester" refer to any compound from which the alcohol moiety is easily removed, e.g., esters of volatile alcohols, C 1~4 It is intended to include an alcohol (preferably methyl). Volatile alcohols are highly desirable. Methyl esters are the most preferred ester reactants. Suitable ester reactants can be prepared by the reaction of diazoalkanes with fatty acids or can be derived by alcoholysis from fatty acids naturally occurring in fats and oils. Non-limiting examples are methyl octanoate (caprylate), methyl decanoate (caprate), methyl dodecanoate (laurate), methyl tetradecanoate (myristate), methyl hexadecanoate (palmitate), methyl octadecanoate (stearate), methyl oleate, ethyl dodecanoate (laurate), ethyl tetradecanoate (myristate), isopropyl dodecanoate (laurate), isopropyl tetradecanoate (myristate), and mixtures thereof. Suitable fatty acid esters can be derived from synthetic or natural saturated or unsaturated fatty acids. Non-limiting examples of saturated fatty acids include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, and stearic acid. Mixtures of fatty acids derived from coconut oil, cottonseed oil, palm kernel oil, soybean oil, cottonseed oil, rapeseed oil, safflower oil, canola oil (low erucic acid), and corn oil, and mixtures thereof. Coconut oil is most preferred.

[0060] The fatty acid alkyl ester is preferably highly purified to remove color / odor materials, oxidation products, and their precursors. The free fatty acid level may be less than about 0.1% by weight of the ester, preferably less than about 0.05% by weight. In addition, the fatty acid alkyl ester should have the lowest possible water content, since any water present can react with the alkoxide catalyst, inhibit the amidation reaction, and increase the soap level.

[0061] The method may include adding about 0.90 to about 1.50 moles, preferably about 0.95 to about 1.20 moles, or more preferably about 1.00 to about 1.05 moles of fatty alkyl ester per mole of alkali salt of aminoalkanesulfonic acid (specifically, all values ​​within these ranges and any ranges created thereby). As shown in the examples, when (a) the aminoalkanesulfonic acid of formula (II) or (b) the anhydrous alkali salt of aminoalkanesulfonic acid of formula (II) and fatty alkyl ester are used in approximately equimolar amounts, a highly active surfactant composition with low levels of impurities is possible without further processing steps. Use of excess fatty alkyl ester results in a surfactant composition contaminated with unreacted fatty alkyl ester, thus requiring further processing for its removal. It is less desirable to use an excess of (a) the aminoalkanesulfonic acid of formula (II) or (b) the anhydrous alkali salt of the aminoalkanesulfonic acid of formula (II) because (i) it is more expensive than the fatty alkyl esters, (ii) it does not have surface-active properties, and (iii) it is difficult and expensive to recover the unreacted amino acid salt from the surfactant mixture.

[0062] Surprisingly, the reaction between (a) an aminoalkanesulfonic acid of formula (II) or (b) an anhydrous alkali salt of an aminoalkanesulfonic acid of formula (II) and an aliphatic alkyl ester of formula (III) can be carried out under atmospheric or even negative pressure while continuously distilling off the alkyl alcohol (e.g., methanol) from the reaction mixture. Temperature conditions for the amidation reaction can range from about 65°C to about 190°C, or from about 90°C to about 160°C, specifically including all values ​​within these ranges and any ranges created thereby. The progress of the reaction can be monitored and / or quantitatively monitored by monitoring the amount of alkyl alcohol collected. 1 The final high activity N-acylaminoalkanesulfonate surfactant reaction mixture produced under these conditions can be ground, flaked, prilled, pelletized, and / or formed into beads, noodles, needles, and ribbons by methods known to those skilled in the art.

[0063] The reaction may utilize an inert gas headspace to help reduce the level of oxygen available during the reaction. The reduced oxygen level helps reduce the amount of oxidation of the reaction components. Oxidation of the components can cause discoloration. A suitable example of an inert gas that may be utilized is nitrogen.

[0064] Additionally, an advantage of carrying out the reactions described herein at atmospheric pressure or even negative pressure is that the resulting surfactant can be substantially solvent-free (if desired). Additionally, the alkyl alcohol, e.g., methanol, vapor can be condensed and recovered outside the reactor. This collection of alkyl alcohol vapor can be reused to produce more methyl esters. The resulting surfactant can have less than about 5.0 wt. %, less than about 3.0 wt. %, or less than about 2.0 wt. % fatty acid methyl esters, including all values ​​within these ranges and any ranges created thereby.

[0065] One advantage of the process of the present disclosure is that the resulting N-acylaminoalkanesulfonate surfactant of formula (I) can be made substantially solvent-free, of high purity, and without additional purification steps, without using excess reactants.

[0066] To make a pumpable surfactant composition (pumpable below 50°C), the active surfactant mixture without any further purification can be diluted with water in amounts of 20-70% by weight of the surfactant mixture, and about 25-50% by weight of the surfactant mixture. Alternatively, water can be added to the high-active surfactant melt at temperatures below 120°C, or below 100°C, with good mixing. The amount of water required will depend on the target surfactant activity level, target viscosity, and surfactant solubility behavior. Solid forms of surfactants (powders, flakes, pellets, beads, needles, noodles) can also be dissolved in water to make a pumpable surfactant composition for formulators to easily incorporate into cleaning formulations.

[0067] The present method can be carried out in batch, semi-continuous, or continuous mode using a suitable reactor configuration.The N-acylaminoalkanesulfonate surfactant composition disclosed herein can be prepared using a conventional stirred tank batch reactor known to those skilled in the art, equipped with a means for heating the reactants, a vapor column and condenser for collecting volatile alkyl alcohol, an efficient agitator capable of stirring the reaction product mixture, a means for blanketing the reactor contents with nitrogen, and optionally a high vacuum system capable of achieving a high vacuum of less than 20 mm Hg.

[0068] Other reactors useful in the present disclosure are suitably devices capable of mixing a liquid and solid mixture of liquid and solid materials using shear forces. In static housings, movement of the reaction mixture is effected by an internal mechanical stirring or mixing device. The reactor can be a kneader or mixer equipped with a sigma blade, masticator blade, or plow-type agitator. Additional useful devices include horizontal or vertical compulsory mixers equipped with a mixing tool, such as a sigma blade, masticator blade, plow-type agitator, or throwing paddle, in combination with a cutting rotor.

[0069] Suitable horizontal compulsory mixers are those equipped with a mixing tool or a combination of mixing tools, such as sigma blades, masticator blades, or plow-type agitators, in combination with a cutting rotor mounted on a drum, more preferably those operating at Froude numbers of 0.1 to 6, 0.25 to 5, or 0.4 to 4, and equipped with a mixing tool or a combination of mixing tools, such as sigma blades, masticator blades, or plow-type agitators, in combination with a cutting rotor mounted on a drum. Without wishing to be bound by theory, the Froude number (Fr) plays a key role in the processing of the mixing method. This dimensionless quantity indicates the relationship between the inertial force acting on moving particles and gravity, where the following equation is applicable: Fr=v 2 / rg During the ceremony, v=peripheral speed [m / s] r = radius of mixing drum [m] g=gravitational acceleration [m / s 2 ] v=π×D×n / 60 During the ceremony, D = diameter of mixing drum [m] N = shaft rotation speed [rpm]

[0070] The N-acylaminoalkanesulfonate surfactant compositions and methods of making described herein have many advantages over known commercial manufacturing methods, including the following: 1) A highly active surfactant composition that is substantially free of solvents and halide salts such as sodium chloride. 2) High conversions and yields can be achieved while avoiding tedious purification steps and attendant product losses. 3) Fewer chemical engineering unit operations, which can result in significant reductions in energy consumption. 4) As described herein, it does not contain toxic and hazardous reagents, thus eliminating the problems of handling these materials. 5) The resulting surfactant is substantially free of solvents that must be removed through additional post-reaction processing steps, as solvents can limit and / or affect the application and / or formulatability of the surfactant. 6) Producing N-acylaminoalkanesulfonates from aliphatic alkyl esters. 7) Conversion and yield of at least 75%, preferably 80% or more. 8) Lower reaction temperature. 9) There is no need to prepare fatty acid chlorides. 10) Avoid using excess fatty acids (which ultimately contaminate the product and have to be removed later). 11) There is no waste stream and the recovered methanol can be recycled to make fatty alkyl esters. 12) Reaction at atmospheric pressure (not pressurized conditions).

[0071] Because the amount of methanol provided by the catalytic amount of anhydrous base, sodium methoxide solution, or generated from the amidation reaction is not sufficient to overcome the lack of miscibility / compatibility between the aforementioned alkali metal salts of aminoalkanesulfonic acids and the fatty alkyl esters, it is desirable to add a solvent to the process. The solvent may be the same as or different from methanol, but is preferably the same as that present in the anhydrous base and formed in the amidation reaction.

[0072] After contacting the aminoalkanesulfonic acid with the anhydrous base, a substance resembling a white solid aggregate may be formed. Therefore, it is believed that a lower conversion rate and yield to the N-acylaminoalkanesulfonate surfactant can be achieved by first adding the aminoalkanesulfonic acid to the anhydrous base (sodium methoxide solution) and then adding the fatty alkyl ester. Therefore, in this method, it is preferable to form the alkali metal salt of the aminoalkanesulfonic acid in situ by adding the aminoalkanesulfonic acid to a mixture consisting of the anhydrous base and the fatty alkyl ester. Without being bound by theory, this is advantageous because the resulting alkali metal salt of the aminoalkanesulfonic acid that forms is finely dispersed or soluble in the mixture containing the fatty alkyl ester.

[0073] Application and Use In another aspect, the present disclosure relates to a consumer product cleaning or personal care composition comprising, based on the total weight of the composition, from about 0.001% to about 99.999% by weight, or from about 0.1% to about 80% by weight, of an N-acylaminoalkanesulfonate surfactant described herein, and from about 0.001% to about 99.999% by weight of one or more additional cleaning components or one or more additional personal care components. In various embodiments, the at least one cleaning component is selected from the group consisting of surfactants, enzymes, builders, alkali systems, organic polymeric compounds, hueing dyes, bleaching compounds, alkanolamines, soil suspending agents, anti-redeposition agents, corrosion inhibitors, and mixtures thereof. In some cases, the composition is selected from the group consisting of granular detergents, detergent bars, liquid laundry detergents, liquid hand dishwashing compositions, hard surface cleaners, tablets, disinfectants, industrial cleaners, highly compressed liquids, powders, and decontaminants. In one class of cases, the composition is enclosed within a sachet or multi-compartment pouch containing both a solid and a liquid compartment.

[0074] In some embodiments, the at least one personal care component is selected from the group consisting of oils, emollients, moisturizers, carriers, extracts, vitamins, minerals, anti-aging compounds, surfactants, solvents, polymers, preservatives, antibacterial agents, waxes, particles, colorants, dyes, fragrances, and mixtures thereof. In various cases, the composition is a shampoo, hair conditioner, hair treatment, facial soap, body wash, body soap, foam bath, makeup remover, skin care product, acne control product, deodorant, antiperspirant, shaving aid, cosmetic, depilatory, fragrance, and mixtures thereof. In one class of cases, the composition is delivered in a form selected from the group consisting of wipes, cloths, bars, liquids, powders, creams, lotions, sprays, aerosols, foams, mousses, serums, capsules, gels, emulsions, doe feet, roll-on applicators, sticks, sponges, ointments, pastes, emulsion sprays, tonics, cosmetics, and mixtures thereof. In various embodiments, the composition further comprises a product selected from the group consisting of a device, an implement, an applicator, an implement, a comb, a brush, a substrate, and mixtures thereof. In some embodiments, the composition is dispensed from an article selected from the group consisting of a bottle, a jar, a tube, a sachet, a pouch, a container, a bottle, a vial, an ampoule, a compact, a wipe, and mixtures thereof.

[0075] Further Method Embodiments In an embodiment, the method may include an amidation reactor. In this embodiment, an aminoalkanesulfonic acid stream, an anhydrous base stream, and an aliphatic alkyl ester stream are fed to the amidation reactor to produce a first stream having an N-acylaminoalkanesulfonate surfactant and a second stream having alkyl alcohol vapors accompanied by the aliphatic alkyl ester. In this embodiment, an alkyl alcohol recovery step may be added to separate the aliphatic alkyl esters entrained in the second stream (the alkyl alcohol vapor stream) to form a third stream (the aliphatic alkyl ester stream) and recover the alkyl alcohol to produce a fourth stream. The fourth stream is a recovered alkyl alcohol that can be used as is, or optionally after further purification, in another method for making aliphatic alkyl esters or for other uses. The third stream, comprising a composition of aliphatic alkyl esters and alkyl alcohols, may optionally be further purified.

[0076] In an embodiment, a solids handling (cooling-crushing / grinding) unit may be added. In this embodiment, the first stream (N-acylaminoalkanesulfonate surfactant) is then fed to the solids handling unit to form an N-acylaminoalkanesulfonate surfactant product stream. In an embodiment, the N-acylaminoalkanesulfonate surfactant product stream is no longer hot and is substantially free of impurities including water, salt (NaCl), polyol solvent, and alkyl alcohol.

[0077] In an embodiment, a dissolution unit / reactor may be added, in which the first stream (N-acylaminoalkanesulfonate surfactant) is fed to a dissolution unit to produce a stream of aqueous N-acylaminoalkanesulfonate surfactant solution.

[0078] In some embodiments, a second amidation reactor may be added. In some embodiments, the second amidation reactor may operate in parallel or sequentially with the first amidation reactor. In some embodiments, the second amidation reactor operates in parallel with the first amidation reactor, producing a fifth stream having alkyl alcohol vapors with accompanying aliphatic alkyl esters. The fifth stream may be combined with the alkyl alcohol vapor stream from the first amidation reactor and then fed to an alkyl alcohol recovery unit. While not intending to be bound by theory, adding a second amidation reactor increases product production and provides a convenient and effective way to schedule reactor maintenance and / or repairs without increasing the manufacturing plant's footprint and capital expenditures for installing a second alkyl alcohol recovery unit and utilities (such as a hot oil boiler system). [Example]

[0079] Analysis by chromatography / mass spectrometry revealed / confirmed the presence of N-acyl-N-methylaminoalkanesulfonates in the product obtained from the reaction to N-acylaminoalkanesulfonates. A sample was weighed and diluted with 100% MeOH to a concentration of 1 mg / mL (assuming 100% purity). The solution was further diluted with 50 / 50 MeOH / water to 50 ppm. The sample was analyzed by UPLC-CAD-HRMS on a reversed-phase ACQUITY UPLC BEH C18 2.1 x 150 mm (5 μL injection). Full scan and MS2 scan information were both collected in negative ion electrospray mode.

[0080] Further analysis of the sample by 2D NMR experiments further confirmed the presence of N-acyl-N-methylaminoalkanesulfonates and the NMR peaks were assigned.

[0081] Analysis of reaction products 1 1 H NMR analysis was performed.

[0082] The reaction product and internal standard (IS) were weighed in a scintillation vial using a precision balance (0.1 mg readability). A 2:1 v / v solvent mixture of deuterated chloroform and methanol (CDCl3-CD3OD) was added to the vial to completely dissolve the sample and IS (one or two drops of DO may be required to completely dissolve the sample). 1 H NMR spectra were standardized 1 The samples were recorded at 600 MHz using a H pulse sequence, a pulse width of 12.00, a 60-second delay, and an acquisition time of 2.59 seconds. NMR data were processed using MestReNova software version 14.2.1. The weight percent was calculated using the integral of the triplet at δ 3.54-3.56 ppm, assigned to the methylene (-CH2-) group of the N-acylaminoalkanesulfonate surfactant. The weight percent was calculated using the integrals of the peaks at δ 3.73-3.76 and 3.68-3.71, corresponding to the rotamers of the methylene (-CH2-) group of the N-acylaminoalkanesulfonate surfactant. The weight percent was calculated using the integral of the singlet at δ 3.65 ppm, assigned to the methyl (CH3-) of any residual aliphatic methyl esters. The integrals were compared to the integral area of ​​the IS and used in the calculation. The weight percent of each species was calculated using the following equation:

[0083]

number

[0084] The same procedure was repeated, but instead, the sample and IS were dissolved in deuterium oxide (DO). The weight percent was calculated using the integral of the triplet at δ 3.56–3.59 ppm, assigned to the methylene (–CH–) group of the N-acylaminoalkanesulfonate surfactant. The weight percent of fatty acid soap was calculated using the integral of the triplet at δ 2.16–2.18 ppm for the methylene (–CH–C(O)–OM) adjacent to the carboxylate group. The soap peak (–CH–C(O)–OM) partially overlaps with another peak (–CH–C(O)–NH–) corresponding to the surfactant, but not in DO. Therefore, the soap level could not be quantified in the deuterated chloroform-methanol (CDCl–CDOD) solvent system.

[0085] Apparatus: The conversion was carried out using a horizontal forced mixer equipped with a plow-type agitator. The apparatus included a thermocouple attached to the mixing drum with a digital temperature readout, a labyrinth-design heating jacket to ensure uniform flow around the mixing drum, a condenser fitted with a cover secured to a flanged port on the top of the vessel, a receiver on a weighing balance, and an inert gas inlet. A discharge port using a manual ball valve was available at the bottom of the mixing drum. A heating circulator with a heating fluid was used to heat the mixer. The product reactants were discharged onto glass baking trays. The amount of condensed methanol (grams), the temperature of the reaction mixture (°C), and the inlet temperature of the heating fluid (°C) were trended in real time.

[0086] Ingredients used: 2-Aminoethanesulfonic acid (taurine), crystalline solid Sodium methoxide solution - approximately 25% by weight in methanol CE-1270-C 12 and C 14 Methyl esters of lauric / myristic acid 75 / 25 blend Coco fatty acid methyl esters (coco FAMEs) - The carbon chain length distribution range for coco fatty acid methyl esters is shown below: C8=0~10% C 10 =0~7% C 12 =50~65% C 14 =18~22% C 16 =0~10% C 18 =0~10% C 18~1 =0~7%

[0087] Examples 1 to 4 Preparation of sodium C1214 taurate Under nitrogen, CE-1270 (769.0 g, 3.46 mol), sodium methoxide (790.8 g, 3.53 mol), and taurine (413.0 g, 3.30 mol) were charged to a reactor and mixed at a temperature of 22–35°C. The temperature of the reaction mixture was gradually increased. The mixer was operated at a Froude number of 0.4–2, depending on the rheology of the composition. The temperature of the reaction mixture was gradually increased. Methanol began to distill off and condense when the reaction mixture temperature reached 68–69°C and remained stable for a period of time. The temperature of the reaction mixture began to rise steadily when approximately 60% or more of the total theoretical amount of methanol expected had been recovered. The contents of the reactor were heated to 168°C. The reaction mixture was held at 165–168°C for 110 minutes. Methanol formed during the reaction was distilled off from the base and condensed as the temperature increased. The mixer and its contents were then allowed to cool to ambient temperature while the shaft with the plow mixing elements continued to rotate. After opening the ball valve, the powdered product was removed from the mixing drum through the bottom port. Additional product was manually collected after removing the front cover bolted to the mixing drum. A yield of 1,100 g of an off-white solid powder was recovered.

[0088] Other experiments were performed to evaluate the effects of temperature and time and are summarized in Table A. Starting materials and conditions were identical to Experiment 1 except where otherwise noted through footnotes.

[0089] [Table 1]

[0090] As shown in Table A, Example 2 demonstrates that a 10°C decrease in temperature relative to Example 1 results in slightly lower conversion and yield, even with extended time at this temperature. In Example 3, a 20°C increase in temperature and 70 minutes increase in time relative to Example 1 achieves similar conversion and yield, but the product exhibits a relatively darker color as indicated by the APHA and Gardner values. Example 4 demonstrates that the reaction results in a composition containing C8 carbon chains and C 10 Compared to Example 1, which uses a carbon chain-containing FAME, the same temperature but shorter time results in a similar quality product. These experiments show that temperature and time at temperature are important parameters in achieving good conversion and yield, and that there is an optimal range to do so with low color development.

[0091] Examples 5 to 8 Carbon chain length distribution of Coco FAME used in this experiment: C = 8.6%, C 10 =6.2%, C 12 =50.1%, C 14 =18.0, C 16 = 8.8% and C 18:0 =8.1%.

[0092] Preparation of sodium cocoyl taurate Coco FAME (768.5 g, 3.50 mol), sodium methoxide (839.5 g, 3.75 mol), and taurine (438.2 g, 3.50 mol) were charged to a reactor under nitrogen and mixed at a temperature of 22–35°C. The temperature of the reaction mixture was gradually increased. The mixer was operated at a Froude number of 0.4–2, depending on the rheology of the composition. The temperature of the reaction mixture was gradually increased. Methanol began to distill off and condense when the reaction mixture temperature reached 68–69°C and remained stable for a period of time. The temperature of the reaction mixture began to rise steadily when approximately 60% or more of the total theoretical amount of methanol expected had been recovered. The reactor contents were heated to 191°C. The reaction mixture was held at 188–191°C for 120 minutes. Methanol formed during the reaction was distilled off from the base and condensed as the temperature increased. The mixer and its contents were then allowed to cool to ambient temperature while the shaft with the plow mixing elements continued to rotate. After opening the ball valve, the powdered product was removed from the mixing drum through the bottom port. Additional product was manually collected after removing the front cover bolted to the mixing drum.

[0093] The powdered product contained 75.0 wt% sodium cocoyl taurate, 7.3 wt% sodium cocoyl N-methyl taurate, 9.1 wt% fatty acid soap, and 0.5 wt% FAME. A solution of this surfactant (10 wt% active surfactant) showed a Gardner value of 4.7 and an APHA of 104, measured in a Lovibond PFX-i Series, S / N 104146, 100 mm cell path.

[0094] Additional experiments were conducted to evaluate the use of coco FAMEs containing unsaturated C-chains. These are summarized in Table B. The FAME feedstock used had a slightly yellow hue compared to the fully saturated version used in Example 5. The reactants and conditions were identical to Example 5, except where otherwise noted through footnotes. Examples 6 and 8 each produced sodium cocoyl taurate surfactant compositions of similar quality to the fully saturated version of Example 5. However, in Example 8, it can be observed that higher temperatures and longer times cause increased color development. On the other hand, Example 7 indicates that the time at temperature was not long enough to convert the reactants to products, as can be observed with the relatively high levels of FAME in the surfactant composition.

[0095] [Table 2]

[0096] Example 9 Carbon chain length distribution of FAME used in this experiment: C 12 =59.3%, C 14 =21.3, C 16 = 9.1% and C 18:0 =1.3%, C 18:1 =8.2%, C 18:2 =0.6%.

[0097] Preparation of C12-C18 sodium taurates Under nitrogen, FAME (802.9 g, 3.47 mol), sodium methoxide (795.3 g, 3.53 mol), and taurine (413.0 g, 3.30 mol) were charged to a reactor and mixed at a temperature of 22–35°C. The temperature of the reaction mixture was gradually increased. The mixer was operated at a Froude number of 0.4–2, depending on the rheology of the composition. The temperature of the reaction mixture was gradually increased. Methanol began to distill off and condense when the reaction mixture temperature reached 70–71°C and remained stable for a period of time. The temperature of the reaction mixture began to rise steadily when approximately 60% or more of the total theoretical amount of methanol expected had been recovered. The contents of the reactor were heated to 172°C. The reaction mixture was held at 169–172°C for 210 minutes. Methanol formed during the reaction was distilled off from the base and condensed as the temperature increased. The mixer and its contents were then allowed to cool to ambient temperature while the shaft with the plow mixing elements continued to rotate. After opening the ball valve, the pale yellow "granular" product was removed from the mixing drum through the bottom port. Additional product was manually collected after removing the front cover bolted to the mixing drum.

[0098] The powdered product contained 75.5 wt% C1218 sodium taurate, 6.7 wt% N-methyl C1218 sodium taurate, 9.6 wt% fatty acid soap, and 2.2 wt% FAME. A solution of this surfactant (10 wt% active surfactant) showed a Gardner value of 11.3 and an APHA of >505, measured in a Lovibond PFX-i Series, S / N 104146, 100 mm cell path.

[0099] Example 10 Carbon chain length distribution of FAME used in this experiment: C 12 =60.4%, C 14 =21.7, C 16 = 8.5% and C 18:0 =1.0%, C 18:1 =7.4%, C 18:2 =0.5%.

[0100] Preparation of N-methyl C12-C18 sodium taurate A reactor was charged under nitrogen with FAME (809.2 g, 3.50 mol), sodium methoxide (59.4 g, 0.25 mol), 250 mL of methanol, and dry sodium N-methyl taurate (576.6 g, 3.58 mol) and mixed at a temperature between 22 and 35 °C. The temperature of the reaction mixture was gradually increased. The mixer was operated at a Froude number between 0.4 and 2, depending on the rheology of the composition. The temperature of the reaction mixture was gradually increased. Methanol began to distill off and condense when the reaction mixture temperature reached 74 °C and began to rise steadily. The reactor contents were heated to 182 °C. The reaction mixture was held at 179 and 182 °C for 70 minutes. All methanol distilled off and condensed as the temperature increased. The mixer and its contents were then cooled to ambient temperature while the shaft equipped with a plow mixing element continued to rotate. After removing the bolted front cover to the mixing drum, the off-white reaction product was manually collected and contained 55.0 wt.% N-methyl C1218 sodium taurate, 10.3 wt.% fatty acid soap, 13.6 wt.% FAME, and an indeterminate level of N-methyl sodium taurate.

[0101] Example 11 Comparative Example Effect of added glycerin This example shows that the presence of glycerin as a solvent significantly reduces the taurine conversion and surfactant yield.

[0102] Carbon chain length distribution of FAME used in this experiment: C = 6.4%, C 10 =64.9%, C 12 =62.9%, C 14 =22.6, C 16 =2.6%.

[0103] Preparation of C8-C16 sodium taurinate A reactor was charged with FAME (1148.2 g, 5.36 mol), sodium methoxide (1220.4 g, 5.74 mol), glycerin (177.1 g), and taurine (670.9 g, 5.36 mol) under nitrogen and mixed at a temperature of 22-35°C. The temperature of the reaction mixture was gradually increased. The mixer was operated at a Froude number of 0.4-2, depending on the rheology of the composition. The temperature of the reaction mixture was gradually increased. Methanol began to distill off and condense when the reaction mixture temperature reached 68-69°C and remained stable for a period of time. The reactor contents were heated to 157°C. The reaction mixture was held at 155-157°C for 120 minutes. Methanol formed during the reaction distilled off from the base and condensed as the temperature increased. The mixer and its contents were then cooled to ambient temperature while the shaft equipped with a plow mixing element continued to rotate. After removing the bolted front cover from the mixing drum, a paste-like reaction product with a heavy fatty acid methyl ester odor was manually removed from the reactor, containing 24.6 wt% C8-C16 sodium taurinate, 5.6 wt% fatty acid soap, 21.8 wt% FAME, and 26.3 wt% sodium taurinate.

[0104] Example 12 130L reactor size Fatty acid methyl ester CE1270 (methyl laurate / methyl myristate available from P&G Chemicals) (29.0 kg), 25 wt % sodium methoxide solution in methanol available from Sigma-Aldrich (29.1 kg), and 2-aminoethanesulfonic acid (taurine available from Spectrum Chemical Mfg. Corp.) (15.7 kg) were charged under nitrogen into a 130-liter horizontal compulsory mixer (FM-130 Plow Batch Mixer available from B&P Littleford) equipped with a plow-type agitator and a high-temperature heating jacket (hot oil) attached to an industrial digital floor scale, two condensers, two receivers, and an inert gas inlet. The mixture was gradually heated to 150°C over 10 hours, during which time evaporated methanol was condensed outside the mixer. Any fatty acid methyl esters entrained in the methanol vapor were condensed (condenser at approximately 70-80°C) and collected in the first receiver, while the methanol was condensed (condenser at approximately 5-10°C) and collected in the second receiver. The reaction mixture was maintained at 150-160°C for 2 hours. 30.0 kg of methanol was recovered. The mixer and the product mass contained therein were then cooled to ambient temperature while the shaft equipped with the plow mixing element continued to rotate. The powdered product was free-flowing and discharged from the mixer through a discharge port at the bottom of the vessel into a lined fiber drum. A yield of 42.6 kg was collected. The final product had the following composition as determined by NMR analysis: 74.15 wt% C1214 sodium taurate, 7.05 wt% C1214 sodium N-methyl taurate, 7.80 wt% fatty acid soap, and 4.75 wt% FAME. A solution of this surfactant (10 wt. % active surfactant) showed a Gardner value of 0.3 and an APHA of 68.5 when measured with a Lovibond PFX-i Series, S / N 104146, using 10 mm and 100 mm cell paths, respectively. A Bruker Avance III 600 MHz magnetic resonance spectrometer (with SampleJet) was used for NMR analysis. NMR data were processed using MestReNova software version 14.2.1, available from Mestrelab.

[0105] Example 13 130L reactor size Fatty acid methyl ester CE1270 (methyl laurate / methyl myristate available from P&G Chemicals) (36.2 kg), 25 wt % sodium methoxide solution in methanol available from Sigma-Aldrich (36.1 kg), and 2-aminoethanesulfonic acid (taurine available from Spectrum Chemical Mfg. Corp.) (19.5 kg) were charged under nitrogen into a 130-liter horizontal compulsory mixer (FM-130 Plow Batch Mixer available from B&P Littleford) equipped with a plow-type agitator and a high-temperature heating jacket (hot oil) attached to an industrial digital floor scale, two condensers, two receivers, and an inert gas inlet. The mixture was gradually heated to 150°C over 7 hours, during which time evaporated methanol was condensed outside the mixer. Any fatty acid methyl esters entrained in the methanol vapor were condensed (condenser at approximately 70-80°C) and collected in a first receiver, while the methanol was condensed (condenser at approximately 5-10°C) and collected in a second receiver. The reaction mixture was maintained at 150-160°C for 2.5 hours. 37.0 kg of methanol was recovered.

[0106] The mixer and the product mass therein were then cooled to ambient temperature while the shaft, equipped with plow mixing elements, continued to rotate. The powdered product was free-flowing and discharged from the mixer into a lined fiber drum through a discharge port at the bottom of the vessel. A yield of 53.7 kg was collected. The final product had the following analytical results: 72.40 wt% C1214 sodium taurate, 9.10 wt% C1214 sodium N-methyl taurate, 8.85 wt% fatty acid soap, and 3.80 wt% FAME. A solution of this surfactant (10 wt% active surfactant) showed a Gardner value of 0.4 and an APHA of 77.3, measured with a Lovibond PFX-i Series, S / N 104146, using 10 mm and 100 mm cell paths, respectively. A Bruker Avance III 600 MHz magnetic resonance spectrometer equipped with SampleJet was used for NMR analysis. NMR data were processed using MestReNova software version 14.2.1 available from Mestrelab.

[0107] Example 14 Manufacturing and dissolving 130L reactor size Fatty acid methyl ester CE1270 (methyl laurate / methyl myristate available from P&G Chemicals) (41.2 kg), 25 wt % sodium methoxide solution in methanol available from Sigma-Aldrich (40.9 kg), and 2-aminoethanesulfonic acid (taurine available from Spectrum Chemical Mfg. Corp.) (22.2 kg) were charged under nitrogen into a 130-liter horizontal compulsory mixer (FM-130 Plow Batch Mixer available from B&P Littleford) equipped with a plow-type agitator and a high-temperature heating jacket (hot oil) attached to an industrial digital floor scale, two condensers, two receivers, and an inert gas inlet. The mixture was gradually heated to 150°C over 6.5 hours, during which time evaporated methanol was condensed outside the mixer. Any fatty acid methyl esters entrained in the methanol vapor were condensed (in the condenser at approximately 70-80°C) and collected in the first receiver, while the methanol was condensed (in the condenser at approximately 5-10°C) and collected in the second receiver. The reaction mixture was maintained at 150-160°C for 3.5 hours. The hot reaction mass was then removed to a container located below the mixer. The container contained water at ambient temperature and was equipped with an impeller. The top of the container was covered by an enclosure connecting it to a contoured discharge opening located at the bottom of the mixer. A stream of N2 gas was passed through the system to expel air, and the discharge system was blanketed with N2. The hot reaction mass was removed from the mixer by opening the discharge door. While mixing with the impeller, the material was allowed to fall into a water-containing container to dissolve and cool the surfactant, resulting in a concentrated aqueous surfactant solution at 61°C.

[0108] The mixer was relatively clean, and once cooled and inspected, approximately 100 g of residual solid product was found inside. This residual solid was crushed and analyzed as follows: 70.2 wt% C1214 sodium taurate, 4.3 wt% C1214 N-methyl sodium taurate, 8.1 wt% fatty acid soap, and 8.3 wt% FAME. A solution of this surfactant (10 wt% active surfactant) showed a Gardner value of 0.3 and an APHA of 58.9, measured with a Lovibond PFX-i Series, S / N 104146, using 10 mm and 100 mm cell paths, respectively. A Bruker Avance III 600 MHz magnetic resonance spectrometer (with SampleJet) was used for NMR analysis. NMR data were processed using MestReNova software version 14.2.1, available from Mestrelab.

[0109] All documents cited herein, including any cross-referenced or related patents or patent applications, and any patent applications or patents to which this application claims priority or benefit, are incorporated herein by reference in their entirety, unless expressly stated to the contrary. The citation of any document shall not be deemed to be prior art to any subject matter disclosed or claimed herein, or to teach, suggest, or disclose any such subject matter, either alone or in combination with any other reference(s). Furthermore, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall control.

[0110] While particular embodiments of the present disclosure have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the disclosure. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this disclosure.

Claims

1. 1. A surfactant composition comprising: comprising greater than 75% by weight of the surfactant composition of N-acylaminoalkanesulfonate of formula (I); 【Chemistry 1】 During the ceremony, R is C ５ ~C ２１ is an alkyl substituent, R １ is H or C １ ~C ４ represents an alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen; 1. A surfactant composition, wherein the surfactant composition is substantially free of solvent and NaCl.

2. further comprising at least 5%, preferably from about 5 to about 15%, more preferably from about 8 to about 10%, by weight of the surfactant composition, of an N-acyl-N-methylaminoalkanesulfonate surfactant; Preferably, the alkyl substituents are saturated; Preferably, the alkyl substituent is unbranched; Preferably, R is C ７～１７ is an alkyl substituent, 10. The composition of claim 1, wherein the surfactant composition is preferably substantially free of polyol solvents and water.

3. 3. The surfactant composition of claim 1, comprising greater than 85% by weight of the N-acylaminoalkanesulfonate surfactant by weight of the surfactant composition.

4. 4. The surfactant composition of claim 1, further comprising 0 to 1% by weight of the composition of an alkyl alcohol (R'OH).

5. 5. The surfactant composition of any one of claims 1 to 4, comprising less than about 5%, or more preferably less than about 3%, by weight of the surfactant composition of fatty acid methyl esters.

6. the surfactant composition is selected from the group consisting of powders, granules, flakes, noodles, needles, extrudates, ribbons, beads, and pellets, and mixtures thereof; 6. The surfactant composition of any one of claims 1 to 5, wherein the surfactant composition is preferably in a form selected from the group consisting of a granular detergent, a bar detergent, a liquid laundry detergent, a gel detergent, a single-phase or multi-phase unit dose detergent, a single-phase or multi-phase or multi-compartment water-soluble pouched detergent, a liquid hand dish composition, a laundry pre-treatment product, a surfactant contained on or in a porous substrate or a nonwoven sheet, an automatic dishwashing detergent, a hard surface cleaner, a fabric softener composition, a personal care composition, and mixtures thereof.

7. 1. A method for preparing a surfactant composition comprising an N-acylaminoalkanesulfonate surfactant, comprising: (a) an aminoalkanesulfonic acid of formula (II), or (b) an anhydrous alkali salt of an aminoalkanesulfonic acid of formula (II), 【Chemistry 2】 (In the formula, R １ is H or C １ ~C ４ represents an alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen; anhydrous base, and aliphatic alkyl esters of formula (III) 【Transformation 3】 (Wherein R is C ５ ~C ２１ alkyl substituents, and R' is selected from C １ or more alkyl substituents, preferably methyl; N-acylaminoalkanesulfonates of formula (I): 【Chemistry 4】 (In the formula, R is C ５ ~C ２１ is an alkyl substituent, R １ is H or C １ ~C ４ represents an alkyl radical, n is an integer from 1 to 2, and M is a cationic group selected from the group consisting of alkali metal salts and hydrogen; raising the temperature of the mixture to about 190°C or less, preferably to about 170°C or less, and more preferably to about 160°C or less to form a reaction mixture; continuously removing alkyl alcohol from the reaction mixture; A method comprising:

8. 8. The method of claim 7, wherein said surfactant composition further comprises at least 5%, preferably from about 5 to about 15%, more preferably from about 8 to about 10%, by weight of the surfactant composition, of an N-acyl-N-methylaminoalkanesulfonate surfactant.

9. R １ 9. The method of claim 8, wherein is H and the anhydrous base comprises sodium methoxide.

10. The combining step comprises: preparing a suspension of the aminoalkanesulfonic acid salt of formula (II) by adding the aliphatic alkyl ester of formula (III) to the anhydrous alkali salt of the aminoalkanesulfonic acid of formula (II); and contacting the suspension with the anhydrous base to form the mixture.

11. 10. The method of any one of claims 7 to 9, wherein the combining step comprises combining the anhydrous base and the aliphatic alkyl ester of Formula (III) to form a premix, and then adding (a) the aminoalkanesulfonic acid of Formula (II) or (b) the anhydrous alkali salt of the aminoalkanesulfonic acid of Formula (II) to the premix to form the mixture.

12. 12. The method of any one of claims 7 to 11, wherein increasing the temperature of the mixture comprises increasing the temperature of the mixture to about 65°C to about 190°C, preferably about 90°C to about 160°C.

13. (a) the aminoalkanesulfonic acid of formula (II) is selected from taurine (2-aminoethanesulfonic acid), homotaurine (3-amino-1-propanesulfonic acid), and N-methyltaurine (2-methylaminoethanesulfonic acid); (b) the anhydrous alkali salt of aminoalkanesulfonic acid of formula (II) includes sodium 2-aminoethanesulfonate, sodium N-methyltaurine salt, sodium 3-aminopropanesulfonate, sodium 3-(N-methylamino)propanesulfonate, and combinations thereof; The anhydrous base is C １ ~C ４ 13. The method of any one of claims 7 to 12, comprising an alkoxide, preferably sodium methoxide, potassium methoxide, potassium methoxide in methanol solution, or a combination thereof.

14. The mixture from about 0.90 to about 1.50 moles, preferably from about 0.95 to about 1.20 moles, or more preferably from about 1.00 to about 1.05 moles of said fatty alkyl ester per mole of alkali salt of aminoalkanesulfonic acid, and (a) from about 1.00 to about 1.50 moles, preferably from about 1.02 to about 1.20 moles, and more preferably from about 1.05 to about 1.10 moles of said anhydrous base per mole of aminoalkanesulfonic acid of formula (II); (b) from about 0.01 to about 0.5 moles, preferably from about 0.02 to about 0.2 moles, and more preferably from about 0.05 to about 0.1 moles of said anhydrous base per mole of the anhydrous alkali salt of the aminoalkanesulfonic acid of formula (II), or The method according to any one of claims 7 to 13, comprising both.

15. 15. The method of any one of claims 7 to 14, further comprising adding said N-acylaminoalkanesulfonate surfactant to water to form a composition comprising greater than 20%, preferably greater than 25%, more preferably greater than 30% by weight of said N-acylaminoalkanesulfonate surfactant by weight of the composition.

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