CN117342966A - Fatty acyl amino acid triethanolamine salt and preparation method and application thereof - Google Patents

Fatty acyl amino acid triethanolamine salt and preparation method and application thereof Download PDF

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CN117342966A
CN117342966A CN202311302994.8A CN202311302994A CN117342966A CN 117342966 A CN117342966 A CN 117342966A CN 202311302994 A CN202311302994 A CN 202311302994A CN 117342966 A CN117342966 A CN 117342966A
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amino acid
chloride
salt
fatty acyl
acyl amino
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陈浩
孔悠华
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Yueyang Keluode Union Chemical Industry Co ltd
Guangzhou Bafeorii Chemical Co ltd
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Yueyang Keluode Union Chemical Industry Co ltd
Guangzhou Bafeorii Chemical Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/22—Amides or hydrazides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/22—Amides or hydrazides
    • C09K23/24—Amides of higher fatty acids with aminoalkylated sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/28—Aminocarboxylic acids

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Abstract

The invention discloses fatty acyl amino acid triethanolamine salt, a preparation method and application thereof, and belongs to the technical field of chemical industry. The method comprises the following steps: the fatty acyl amino acid salt and triethanolamine hydrochloride are reacted in the membrane reaction device, and the chloride in the membrane reaction device is continuously removed while the fatty acyl amino acid salt and the triethanolamine hydrochloride are reacted. The method has the advantages of simple process, mild reaction conditions, no use of strong acid, no need of heating for acidification, no need of complex post-treatment, stable color of the obtained finished product, no easy occurrence of yellowing, and mild smell and no irritation. The fatty acyl amino acid triethanolamine salt can be used in cosmetics, medicine, food, textile or paper.

Description

Fatty acyl amino acid triethanolamine salt and preparation method and application thereof
Technical Field
The invention relates to the technical field of chemical industry, in particular to fatty acyl amino acid triethanolamine salt, and a preparation method and application thereof.
Background
The amino acid surfactant is a surfactant with an amino acid structure, has excellent biodegradability, biocompatibility and physiological activity, and can be used as a detergent, an emulsifier, a dispersing agent, a wetting agent or an antistatic agent, etc.
Fatty acyl amino acid triethanolamine salt is one of amino acid surfactants, and compared with metal salt amino acid surfactants, the fatty acyl amino acid triethanolamine salt has the characteristics of milder temperature resistance and low temperature resistance, and is widely applied to industries such as cosmetics, medicines, foods, textiles, papermaking and the like. Especially in cosmetics, fatty acyl amino acid triethanolamine salt can be used as main component of shampoo, bath lotion, hair conditioner, etc., and has mild cleaning effect, and also has effects of keeping moisture, caring hair, regulating skin acid-base balance, etc.
The conventional preparation method of fatty acyl amino acid triethanolamine salt at present has complex process, needs to be acidified by adding strong acid at high temperature, has harsh reaction conditions, complex post-reaction treatment, and is easy to generate a large amount of waste water and waste, thereby causing environmental pollution. The obtained product is easy to yellow and has pungent smell.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims at solving or improving the technical problems by using fatty acyl amino acid triethanolamine salt and a preparation method and application thereof.
The application can be realized as follows:
in a first aspect, the present application provides a process for the preparation of fatty acyl amino acid triethanolamine salts comprising the steps of: the fatty acyl amino acid salt and triethanolamine hydrochloride are reacted in the membrane reaction device, and the chloride in the membrane reaction device is continuously removed while the fatty acyl amino acid salt and the triethanolamine hydrochloride are reacted.
In alternative embodiments, the conditions under which the fatty acyl amino acid salt is reacted with triethanolamine hydrochloride include at least one of the following features:
characteristic one: the reaction pressure is 0.1-5MPa, preferably 0.2-1MPa;
and the second characteristic is: the reaction temperature is 10-50 ℃, preferably 20-40 ℃;
and (3) the following characteristics: the ratio of the amounts of fatty acyl amino acid salt to triethanolamine hydrochloride material is 1:0.9 to 1:2.5.
In alternative embodiments, the membranes used in the membrane reactor device comprise microfiltration, ultrafiltration or nanofiltration membranes.
In alternative embodiments, the membrane used in the membrane reactor device is an ultrafiltration membrane or nanofiltration membrane.
In an alternative embodiment, the membrane used in the membrane reactor device is a nanofiltration membrane.
In an alternative embodiment, the preparation of the fatty acyl amino acid salt comprises: at least one of amino acid and amino acid salt and fatty acyl chloride are synthesized into fatty acyl amino acid salt by aqueous phase method under alkaline condition.
In an alternative embodiment, the conditions for synthesizing fatty acyl amino acid salts include one of the following features:
characteristic one: the synthesis temperature is 10-40 ℃;
and the second characteristic is: the pH value in the synthesis process is 9-11;
and (3) the following characteristics: the synthesis time is 4-8h.
In an alternative embodiment, the amino acids and the amino acids salts each independently comprise at least one of sarcosine, glutamic acid, alanine, glycine, aspartic acid, serine, taurine and methyl taurate.
In an alternative embodiment, the amino acid salt comprises at least one of a sodium salt of an amino acid and a potassium salt of an amino acid.
In an alternative embodiment, the amino acid salt comprises at least one of sodium sarcosinate, potassium glycinate, sodium alaninate, sodium glutamate, sodium methyltaurinate and sodium taurate.
In alternative embodiments, the fatty acid chloride is an alkyl acid chloride having 8 to 21 carbon atoms or an alkenyl acid chloride having 8 to 21 carbon atoms.
In alternative embodiments, the fatty acid chloride comprises at least one of octanoyl chloride, isooctanoyl chloride, nonanoyl chloride, isononyl chloride, decanoyl chloride, isodecanoyl chloride, undecanoyl chloride, dodecanoyl chloride, tridecanoyl chloride, tetradecanoyl chloride, pentadecanoyl chloride, hexadecanoyl chloride, heptadecanoyl chloride, octadecanoyl chloride, nonadecanoyl chloride, and eicosanoyl chloride.
In a second aspect, the present application provides a fatty acyl amino acid triethanolamine salt prepared by the preparation method of any one of the previous embodiments.
In an alternative embodiment, the chloride salt is present in the fatty acid triethanolamine salt in an amount of no more than 0.5 weight percent.
In an alternative embodiment, the chloride salt is present in the fatty acid triethanolamine salt in an amount of no more than 0.2 weight percent.
In a third aspect, the present application provides the use of a fatty acyl amino acid triethanolamine salt as in the previous embodiments, for use in cosmetics, medicine, food, textile or paper.
In a fourth aspect, the present application provides a cosmetic comprising the fatty acyl amino acid triethanolamine salt of the foregoing embodiments.
In alternative embodiments, the cosmetic product comprises a shampoo, body wash or hair conditioner.
The beneficial effects of this application include:
according to the preparation method, strong acid is not adopted, high-temperature acidification is not carried out, but the fatty acyl amino acid salt and the triethanolamine hydrochloride are separated and removed through a membrane reactor by a one-pot method to remove small-molecule chloride in a system, so that ion pairs are formed between carboxyl anions in the fatty acyl amino acid of the macromolecules and cations in the triethanolamine hydrochloride of the macromolecules, and the fatty acyl amino acid triethanolamine salt is prepared; at the same time, the low-salt fatty acid triethanolamine salt is prepared by continuously deamidating chloride salt in the process of preparing fatty acid amide salt.
The method avoids the process that the traditional preparation of low-salt fatty acyl amino acid triethanolamine salt needs to be acidified at high temperature to prepare fatty acyl amino acid, salt is removed, and the fatty acyl amino acid and triethanolamine are subjected to salt formation under the condition of solvent or high temperature. The method has higher production efficiency, lower production energy consumption and better atomic economy. The obtained fatty acyl amino acid triethanolamine salt has low content of chloride metal salt, and the product has yellowing resistance, mild smell and no irritation.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the embodiments will be briefly described below, it being understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and other related drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a flow chart of a process for preparing fatty acyl amino acid triethanolamine salts of the present application;
FIG. 2 is a physical diagram of the finished product prepared in example 1 in the test example of the present application;
FIG. 3 is a physical diagram of the final product prepared in comparative example 1 in the test example of the present application.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The fatty acyl amino acid triethanolamine salt provided by the application and a preparation method and application thereof are specifically described below.
The current general preparation method of fatty acyl amino acid triethanolamine salt is as follows: the fatty acyl chloride and the amino acid are condensed and reacted under the condition of an organic solvent to obtain a fatty acyl amino acid surfactant, then inorganic strong acid is added, and the fatty acyl amino acid is prepared by high-temperature acidification and layering, and the fatty acyl amino acid and triethanolamine are prepared into a finished product under the condition of the solvent or the high temperature. Wherein the high temperature acidification and delamination temperature is about 55-80 ℃, and the high temperature conditions of fatty acyl amino acid and triethanolamine are up to 80-90 ℃. Under the above-mentioned acid-added and high-temperature conditions, not only fatty acyl amino acids may turn yellow, but also some amino acids may remain, and furthermore, organic substances tend to generate peculiar smell or decompose to generate other impurity substances under the above-mentioned acid-added and high-temperature conditions.
The present application creatively proposes a method for preparing fatty acyl amino acid triethanolamine salts, which can avoid and solve the above problems. Referring to fig. 1, the method includes the following steps: the fatty acyl amino acid salt and triethanolamine hydrochloride are reacted in the membrane reaction device, and the chloride in the membrane reaction device is continuously removed while the fatty acyl amino acid salt and the triethanolamine hydrochloride are reacted.
As a reference, the pressure at which the fatty acid amide salt is reacted with triethanolamine hydrochloride may be 0.1 to 5MPa, such as 0.1MPa, 0.5MPa, 1MPa, 1.5MPa, 2MPa, 2.5MPa, 3MPa, 3.5MPa, 4MPa, 4.5MPa, or 5MPa, etc., and may be any other value within the range of 0.1 to 5MPa. In some exemplary embodiments, the fatty acid amide salt is reacted with triethanolamine hydrochloride at a pressure of 0.2 to 1MPa, such as 0.2MPa, 0.3MPa, 0.4MPa, 0.5MPa, 0.6MPa, 0.7MPa, 0.8MPa, 0.9MPa, 1MPa, etc.
If the pressure of the reaction of fatty acyl amino acid salt and triethanolamine hydrochloride is less than 0.1MPa, the removal of chloride salt is not facilitated, and the removal speed and the removal rate of the chloride salt are low; if the pressure of the reaction of fatty amide acid salt with triethanolamine hydrochloride is more than 5MPa, the yield tends to be lowered.
The reaction temperature of fatty acyl amino acid salt and triethanolamine hydrochloric acid can be 10-50deg.C, such as 10deg.C, 15deg.C, 20deg.C, 25deg.C, 30deg.C, 35deg.C, 40deg.C, 45deg.C or 50deg.C, etc., or can be any other value within 10-50deg.C. In some typical embodiments, the fatty acid amide salt is reacted with triethanolamine hydrochloride at a temperature of 20-40 ℃, such as 20 ℃, 22 ℃,25 ℃, 28 ℃,30 ℃, 32 ℃, 35 ℃, 38 ℃, 40 ℃, or the like.
If the reaction temperature of fatty acyl amino acid salt and triethanolamine hydrochloride is lower than 10 ℃, the removal of chloride salt is not facilitated, and the removal speed and the removal rate of the chloride salt are low; if the reaction temperature of fatty acyl amino acid salt and triethanolamine hydrochloride is higher than 50 ℃, the yellowing resistance of the product is not good.
The ratio of the amounts of fatty acyl amino acid salt to triethanolamine hydrochloride material may be 1:0.9 to 1:2.5, such as 1:0.9, 1:1, 1:1.2, 1:1.5, 1:1.8, 1:2, 1:2.2, or 1:2.5, etc., as well as any other value in the range of 1:0.9 to 1:2.5.
If the ratio of the amounts of fatty acyl amino acid salt to triethanolamine hydrochloride is less than 1:0.9 (e.g., 1:0.5), the product has poor surface activity; if the ratio of the amounts of fatty acyl amino acid salt to triethanolamine hydrochloride is greater than 1:2.5 (e.g., 1:3), triethanolamine residues are liable to be caused and yellowing resistance is lowered.
In this application, the membranes used in the membrane reactor apparatus include microfiltration, ultrafiltration or nanofiltration membranes. In some preferred embodiments, the membrane used in the membrane reactor device is an ultrafiltration membrane or nanofiltration membrane. In some preferred embodiments, the membrane used in the membrane reactor device is a nanofiltration membrane. In a preferred or more preferred manner, higher chloride removal rates can be achieved to yield low salt fatty acid triethanolamine salts.
By starting the membrane reaction device, under the control of the pressure and the temperature, the chloride salt (such as sodium chloride or potassium chloride) can be continuously separated from the fatty acyl amino acid triethanolamine salt by utilizing the osmotic pressure difference, so as to obtain the low-salt fatty acyl amino acid triethanolamine salt.
In this application, the preparation of fatty acyl amino acid salts includes: at least one of amino acid and amino acid salt and fatty acyl chloride are synthesized into fatty acyl amino acid salt by aqueous phase method under alkaline condition.
The alkaline condition is formed by alkali and water, and can be provided by liquid alkali, specifically, can be formed by compounding NaOH and water.
In some embodiments, the molar amount of fatty acid chloride used to synthesize the fatty acid amide salt to the amino acid and/or amino acid salt used to synthesize the fatty acid amide salt may be 1:1.02-1:1.06 on a molar basis. The liquid base can be used to neutralize HCl produced by the reaction of an amino acid (or amino acid salt) with fatty acid chloride.
As a reference, the temperature at which the fatty acyl amino acid salt is synthesized may be 10 to 40℃such as 10℃C, 15℃C, 20℃C, 25℃C, 30℃C, 35℃C or 40℃C, etc., or may be any other value or any range within the range of 10 to 40 ℃.
The pH during the synthesis of fatty acyl amino acid salt can be 9-11, such as 9, 9.5, 10, 10.5 or 11, etc., or can be any other value or range within 9-11.
The fatty acyl amino acid salt can be synthesized for 4-8h, such as 4h, 4.5h, 5h, 5.5h, 6h, 6.5h, 7h, 7.5h or 8h, and can be any other value within the range of 4-8h.
Wherein each of the amino acids and the amino acid salts independently may include at least one of sarcosine, glutamic acid, alanine, glycine, aspartic acid, serine, taurine, and methyl taurate. In some exemplary embodiments, the amino acid salt comprises at least one of a sodium salt of an amino acid and a potassium salt of an amino acid. In some more typical embodiments, the amino acid salt comprises at least one of sodium sarcosinate, potassium glycinate, sodium alaninate, sodium glutamate, sodium methyltaurinate, and sodium taurate.
The fatty acid chloride may be an alkyl acid chloride having 8 to 21 carbon atoms or an alkenyl acid chloride having 8 to 21 carbon atoms. Illustratively, the alkyl or alkenyl acid chloride may contain 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, or 21 carbon atoms. In some exemplary embodiments, the fatty acid chloride may include at least one of octanoyl chloride, isooctanoyl chloride, nonanoyl chloride, isononyl chloride, decanoyl chloride, isodecanoyl chloride, undecanoyl chloride, dodecanoyl chloride, tridecanoyl chloride, tetradecanoyl chloride, pentadecanoyl chloride, hexadecanoyl chloride, heptadecanoyl chloride, octadecanoyl chloride, nonadecanoyl chloride, and eicosanoyl chloride.
The reaction equation involved in the above reaction process can be referred to, for example, as follows:
it can be understood that: under alkaline condition, amino acid salt and fatty acyl chloride undergo nucleophilic substitution reaction under aqueous condition to produce fatty acyl amino acid salt and hydrogen chloride. Introducing the generated fatty acyl amino acid salt into a membrane reaction device, simultaneously introducing triethanolamine hydrochloride according to a proportion, starting the membrane reaction device, controlling certain pressure and temperature, and separating small-molecular chlorinated metal salt from macromolecular fatty acyl amino acid triethanolamine salt by utilizing osmotic pressure difference to obtain the aqueous solution of the low-salt fatty acyl amino acid triethanolamine salt.
On the contrary, the preparation method does not adopt strong acid, does not carry out high-temperature acidification, but adds triethanolamine hydrochloride directly by a one-pot method without acidification layering treatment, and separates and removes small-molecular chloride salt in the system by a membrane reactor, so that carboxyl anions in the macromolecular fatty acyl amino acid and cations in the macromolecular triethanolamine hydrochloride form ion pairs, thereby preparing fatty acyl amino acid triethanolamine salt; at the same time, the low-salt fatty acid triethanolamine salt is prepared by continuously deamidating chloride salt in the process of preparing fatty acid amide salt.
The method avoids the process that the traditional preparation of low-salt fatty acyl amino acid triethanolamine salt needs to be acidified at high temperature to prepare fatty acyl amino acid, salt is removed, and the fatty acyl amino acid and triethanolamine are subjected to salt formation under the condition of solvent or high temperature. The method has the characteristics of higher production efficiency, lower production energy consumption, better atomic economy, low-temperature reaction in the whole process, yellowing resistance, low odor, low irritation and the like.
Correspondingly, the application also provides fatty acyl amino acid triethanolamine salt which is prepared by the preparation method. The obtained fatty acyl amino acid triethanolamine salt has low content of chloride metal salt, and the product has yellowing resistance, mild smell and no irritation.
In some embodiments, the chloride salt content of the fatty acid triethanolamine salt produced is no more than 0.5wt%. In some preferred embodiments, the chloride salt is present in the fatty acid triethanolamine salt in an amount of no more than 0.2wt%.
In addition, the application also provides application of the fatty acyl amino acid triethanolamine salt, such as application in cosmetics, medicines, foods, textiles or papermaking.
Correspondingly, the application also provides a cosmetic, and the composition of the cosmetic comprises the fatty acyl amino acid triethanolamine salt. The cosmetic may include, by way of example and not limitation, a shampoo, a body wash, a hair conditioner, or the like, which can provide a good use effect to the cosmetic by using a fatty acid triethanolamine salt as one of the ingredients.
The features and capabilities of the present invention are described in further detail below in connection with the examples.
Example 1
This example provides a fatty acyl amino acid triethanolamine salt (lauroyl alanine triethanolamine salt) prepared by the following steps:
into a four-necked flask, 36.6g (0.4108 mol) of alanine, 16g (0.4 mol) of sodium hydroxide and 310.3g of water were charged, followed by stirring well and clearing. The system temperature was controlled at 25-40℃and 86.4g (0.3950 mol) of lauroyl chloride was initially pumped uniformly from 4 hours by peristaltic pump and 25wt% aqueous sodium hydroxide (about 84 g) was pumped to control the pH of the system to 9.5-11, after which the material was pumped in and stirred continuously for 30min at 25-40℃to obtain fatty acyl amino acid salt.
Transferring fatty acyl amino acid salt (533.3G, 0.3792 mol) into a membrane reactor (the membrane is a nanofiltration membrane, the membrane reactor is purchased from Hangzhou Ruina RNM-18G), adding 77.4G (0.4171 mol) triethanolamine hydrochloride into the reactor in 3 batches at the temperature of 25-28 ℃, after dissolving, supplementing 576.2G water until the solid content is 20%, controlling the pressure of the membrane reactor to be 0.2Mpa, the temperature to be 35 ℃, continuously separating sodium chloride, and obtaining 521.2G lauroyl alanine triethanolamine salt after the system chloride ion content is less than 0.2%, the solid content is adjusted to be 30%.
The sodium chloride content of the obtained product was 0.15wt%, the triethanolamine content was about 9.73% and the product yield was 98.12% (theoretical product amount 531.2 g).
Example 2
This example provides a fatty acyl amino acid triethanolamine salt (lauroyl glycine triethanolamine salt) prepared by the following steps:
into a four-necked flask, 40g (0.5328 mol) of glycine, 20g (0.5 mol) of sodium hydroxide and 401.3g of water were charged, and the mixture was stirred well and dissolved. The system temperature is controlled between 25 ℃ and 30 ℃, 112.07g (0.5123 mol) of lauroyl chloride is pumped in evenly from 6 hours by a peristaltic pump, and 30wt% sodium hydroxide aqueous solution (90.85 g) is pumped in to control the pH value of the system between 10 and 11, and after the material is pumped in, stirring is continued for 30min at 25 ℃ to 30 ℃ to obtain fatty acyl amino acid salt.
Transferring fatty acyl amino acid salt (664.18 g,0.4867 mol) into a membrane reactor (same as in example 1), adding 99.38g (0.5353 mol) triethanolamine hydrochloride into the reactor in 3 batches at room temperature of 25-30 ℃, after dissolving, supplementing 729.6g water until the solid content of the system is 20%, controlling the pressure of the membrane reactor to be 0.6Mpa and the temperature to be 30 ℃, continuously separating sodium chloride until the chloride ion content of the system is less than 0.2%, adjusting the solid content to be 30%, and discharging to obtain 644.9g of laurylglycine triethanolamine salt.
The sodium chloride content of the obtained product was 0.18wt%, the triethanolamine content was about 10.10%, and the product yield was 97.85% (theoretical product amount 659.1 g).
Example 3
This example provides a fatty acyl amino acid triethanolamine salt (octanoyl glutamic acid triethanolamine salt), which is prepared by the following steps:
55g (0.3738 mol) of glutamic acid, 30g (0.75 mol) of sodium hydroxide and 334.74g of water are added into a four-necked flask, and the mixture is stirred uniformly and dissolved. The system temperature is controlled to be 10-20 ℃, 58.46g (0.3594 mol) of octanoyl chloride is pumped in uniformly from 5 hours by a peristaltic pump, and 30wt% sodium hydroxide aqueous solution (63 g) is pumped in to control the pH value of the system to be 9-10, and after the material is pumped in, stirring is continued for 40min at the temperature of 10-20 ℃ to obtain fatty acyl amino acid salt.
Transferring fatty acyl amino acid salt (541.2 g,0.3414 mol) into a membrane reactor (same as in example 1), adding 69.7g (0.3756 mol) triethanolamine hydrochloride into the reactor in batches at the room temperature of 20-25 ℃, after dissolving, supplementing water (549.5 g) until the solid content in the system is 20%, controlling the pressure of the membrane reactor to be 1Mpa and the temperature to be 20 ℃, continuously separating sodium chloride until the chloride ion content of the system is less than 0.2%, adjusting the solid content to be 30%, and discharging to obtain 455.1g of octanoyl chloride triethanolamine glutamate.
The sodium chloride content of the obtained product was 0.14wt%, the triethanolamine content was about 8.91%, and the product yield was 94.69% (theoretical product amount 480.6 g).
Example 4
This example provides a fatty acyl amino acid triethanolamine salt (triethanolamine lauroyl taurate salt) prepared by the following steps:
into a four-necked flask, 58g (0.3942 mol) of sodium taurate, 15.7g (0.3925 mol) of sodium hydroxide and 351.9g of water were charged, and the mixture was stirred well and dissolved. The system temperature is controlled between 30 ℃ and 40 ℃, 82.9g (0.379 mol) of lauroyl chloride is pumped in evenly from 4 hours by a peristaltic pump, and 25wt% sodium hydroxide aqueous solution (80.6 g) is pumped in to control the pH value of the system between 10.5 and 11, and after the material is pumped in, stirring is continued for 20 minutes at 30 ℃ to 40 ℃ to obtain fatty acyl amino acid salt.
Transferring fatty acyl amino acid salt (589 g,0.36 mol) into a membrane reactor (same as in example 1), adding 73.5g (0.396 mol) triethanolamine hydrochloride into the reactor in batches of 3 at room temperature of 30-35 ℃, after dissolving, supplementing water (588.6 g) until the solid content in the system is 20%, controlling the pressure of the membrane reactor to be 5Mpa and the temperature to be 40 ℃, continuously separating sodium chloride until the chloride ion content of the system is less than 0.2%, adjusting the solid content to be 30%, and discharging to obtain 528.8g triethanolamine lauroyl taurate.
The sodium chloride content of the obtained product was 0.14wt%, the triethanolamine content was about 9.80%, and the product yield was 96.36% (theoretical product amount 548.8 g).
Example 5
This embodiment differs from embodiment 1 in that: the reaction temperature in the membrane reactor was 10 ℃.
Example 6
This embodiment differs from embodiment 1 in that: the reaction temperature in the membrane reactor was 50 ℃.
Example 7
This embodiment differs from embodiment 1 in that: the membrane used in the membrane reactor device is an ultrafiltration membrane.
Example 8
This embodiment differs from embodiment 1 in that: the membrane used in the membrane reactor device is a microfiltration membrane.
Comparative example 1
This comparative example provides a cocoyl alanine triethanolamine salt (commercial product flavored plain ACT-12).
Comparative example 2
This comparative example provides a lauroyl glycine triethanolamine salt prepared as in example 1 of CN 201510907035.8.
Comparative example 3
The difference between this comparative example and example 1 is that: the reaction pressure in the membrane reactor was 0.05MPa.
Comparative example 4
The difference between this comparative example and example 1 is that: the reaction pressure in the membrane reactor was 6MPa.
Comparative example 5
The difference between this comparative example and example 1 is that: the reaction temperature in the membrane reactor was 5 ℃.
Comparative example 6
The difference between this comparative example and example 1 is that: the reaction temperature in the membrane reactor was 85 ℃.
Comparative example 7
The difference between this comparative example and example 1 is that: the ratio of the amounts of fatty acyl amino acid salt to triethanolamine hydrochloride material was 1:0.6.
Comparative example 8
The difference between this comparative example and example 1 is that: the ratio of the amounts of fatty acyl amino acid salt to triethanolamine hydrochloride material was 1:3.
Test examples
(1) In the example of example 1 and comparative example 1, the physical diagrams of the products prepared by the two are shown in fig. 2 and 3 respectively after being placed in a 60 ℃ incubator for 72 hours.
As can be seen from fig. 2 and 3: the finished product prepared in example 1 was good in color, did not undergo yellowing, and the finished product of comparative example 1 was significantly yellowing.
(2) The results of comparing the odor and the component content of the products obtained in examples 1 to 8 and comparative examples 2 to 8 are shown in Table 1.
Table 1 comparative results
As can be seen from Table 1, the method provided by the embodiment of the application can prepare fatty acyl amino acid triethanolamine salt with yellowing resistance, mild smell, low content of chlorinated metal salt and high yield.
In conclusion, the preparation method of fatty acyl amino acid triethanolamine salt provided by the application is simple in process, mild in reaction condition, free of strong acid, free of heating and acidification, free of complex post-treatment, stable in color, unlikely to cause yellowing, mild in smell, free of irritation, low in chloride metal salt content and high in yield.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. A method for preparing fatty acyl amino acid triethanolamine salt, which is characterized by comprising the following steps: the fatty acyl amino acid salt and triethanolamine hydrochloride are reacted in a membrane reaction device, and the chloride in the membrane reaction device is continuously removed while the fatty acyl amino acid salt and the triethanolamine hydrochloride are reacted.
2. The method of claim 1, wherein the conditions under which the fatty acyl amino acid salt reacts with the triethanolamine hydrochloride comprise at least one of the following characteristics:
characteristic one: the reaction pressure is 0.1-5MPa, preferably 0.2-1MPa;
and the second characteristic is: the reaction temperature is 10-50 ℃, preferably 20-40 ℃;
and (3) the following characteristics: the ratio of the amount of the fatty acyl amino acid salt to the amount of the triethanolamine hydrochloride material is 1:0.9 to 1:2.5.
3. The method of claim 1, wherein the membrane used in the membrane reactor device comprises a microfiltration membrane, an ultrafiltration membrane or a nanofiltration membrane;
preferably, the membrane used in the membrane reactor device is an ultrafiltration membrane or a nanofiltration membrane;
more preferably, the membrane used in the membrane reactor device is a nanofiltration membrane.
4. A process according to any one of claims 1 to 3, wherein the preparation of the fatty acyl amino acid salt comprises: at least one of an amino acid and an amino acid salt is synthesized with fatty acyl chloride by an aqueous phase method under alkaline conditions.
5. The method of claim 4, wherein the conditions for synthesizing the fatty acyl amino acid salt include one of the following features:
characteristic one: the synthesis temperature is 10-40 ℃;
and the second characteristic is: the pH value in the synthesis process is 9-11;
and (3) the following characteristics: the synthesis time is 4-8h.
6. The method according to claim 4, wherein the amino acid and the amino acid in the amino acid salt each independently comprise at least one of sarcosine, glutamic acid, alanine, glycine, aspartic acid, serine, taurine and methyl taurate;
preferably, the amino acid salt comprises at least one of an amino acid sodium salt and an amino acid potassium salt;
preferably, the amino acid salt includes at least one of sodium sarcosinate, potassium glycinate, sodium alaninate, sodium glutamate, sodium methyltaurinate and sodium taurinate.
7. The method according to claim 4, wherein the fatty acid chloride is an alkyl acid chloride having 8 to 21 carbon atoms or an alkenyl acid chloride having 8 to 21 carbon atoms;
preferably, the fatty acyl chloride includes at least one of octanoyl chloride, isononyl chloride, decanoyl chloride, isodecanoyl chloride, undecanoyl chloride, dodecanoyl chloride, tridecanoyl chloride, tetradecanoyl chloride, pentadecanoyl chloride, hexadecanoyl chloride, heptadecanoyl chloride, octadecanoyl chloride, nonadecanoyl chloride and eicosanoyl chloride.
8. A fatty acyl amino acid triethanolamine salt prepared by the preparation method of any one of claims 1 to 7;
preferably, the fatty acyl amino acid triethanolamine salt contains no more than 0.5 wt.% of chloride;
more preferably, the chloride salt content of the fatty acyl amino acid triethanolamine salt is not more than 0.2wt%.
9. Use of the fatty acid triethanolamine salt according to claim 8, characterized in that the fatty acid triethanolamine salt is used in cosmetics, medicine, food, textile or paper.
10. A cosmetic product characterized in that the ingredients of the cosmetic product comprise the fatty acyl amino acid triethanolamine salt according to claim 8;
preferably, the cosmetic comprises a shampoo, a body wash or a hair conditioner.
CN202311302994.8A 2023-10-10 2023-10-10 Fatty acyl amino acid triethanolamine salt and preparation method and application thereof Pending CN117342966A (en)

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