CN111249991A - Production method of fatty alcohol-polyoxyethylene ether sulfuric acid triethanolamine salt containing amino acid groups - Google Patents
Production method of fatty alcohol-polyoxyethylene ether sulfuric acid triethanolamine salt containing amino acid groups Download PDFInfo
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- CN111249991A CN111249991A CN202010049024.1A CN202010049024A CN111249991A CN 111249991 A CN111249991 A CN 111249991A CN 202010049024 A CN202010049024 A CN 202010049024A CN 111249991 A CN111249991 A CN 111249991A
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- fatty alcohol
- polyoxyethylene ether
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- triethanolamine
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- 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
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- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
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- 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
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
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- 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
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
Abstract
The invention provides a production method of fatty alcohol-polyoxyethylene ether sulfate triethanolamine salt containing amino acid groups, which comprises the following steps: adding fatty alcohol-polyoxyethylene ether into a reaction container, slowly adding chlorosulfonic acid while stirring, and continuously vacuumizing during the reaction process to remove hydrochloric acid generated by the reaction; adding triethanolamine water solution for neutralization reaction; and adding amino acid for further neutralization reaction to obtain the fatty alcohol-polyoxyethylene ether triethanolamine sulfate containing amino acid groups. According to the production method of the fatty alcohol-polyoxyethylene ether triethanolamine sulfate salt containing the amino acid groups, the reaction steps are adjusted, and the amino acid is added in the reaction process, so that the amino acid groups are introduced into the fatty alcohol-polyoxyethylene ether triethanolamine sulfate salt product, and the amino acid groups have the characteristics of hydrophilicity and lipophobicity, so that the oil removal performance of the product can be improved, the operation is simple, and the production cost is low.
Description
Technical Field
The invention relates to the field of surfactant production, and particularly relates to a production method of fatty alcohol-polyoxyethylene ether triethanolamine sulfate containing amino acid groups.
Background
Fatty alcohol-polyoxyethylene ether triethanolamine sulfate is a common anionic surfactant, and is often applied to washing products such as shampoos, bath liquids, children's detergents and the like due to the characteristics of low irritation and toxicity, abundant foam, strong detergency, excellent wetting power and good dispersing power. But the oil removing capability is weak, and other hydrophilic and oleophobic surfactants are generally required to be compounded for use. Therefore, the problem that the characteristic of the fatty alcohol-polyoxyethylene ether sulfate triethanolamine salt is improved and the fatty alcohol-polyoxyethylene ether sulfate triethanolamine salt has excellent oil removal performance needs to be solved urgently.
Disclosure of Invention
Aiming at the problems, the invention provides a production method of fatty alcohol-polyoxyethylene ether triethanolamine sulfate containing amino acid groups.
In order to achieve the purpose, the invention is solved by the following technical scheme:
a production method of fatty alcohol-polyoxyethylene ether sulfuric triethanolamine salt containing amino acid groups comprises the following steps:
s1, adding fatty alcohol-polyoxyethylene ether into a reaction container, preheating to 25-27 ℃, slowly adding chlorosulfonic acid while stirring, wherein the reaction time is 2.5-3.5 hours, and simultaneously continuously vacuumizing in the reaction process to remove hydrochloric acid generated by the reaction, wherein the molar mass ratio of the fatty alcohol-polyoxyethylene ether to the chlorosulfonic acid is 1: 1.05-1.1;
s2, raising the temperature to 38-42 ℃, adding a triethanolamine aqueous solution for a neutralization reaction for 1.5-2 hours, wherein the molar mass ratio of triethanolamine to fatty alcohol-polyoxyethylene ether is 0.5-0.8: 1;
s3, raising the temperature to 50-55 ℃, adding amino acid for further neutralization reaction for 1.5-2 h to obtain fatty alcohol polyoxyethylene ether triethanolamine sulfate containing amino acid groups, wherein the molar mass ratio of the amino acid to the fatty alcohol polyoxyethylene ether is 0.25-0.55: 1;
s4, adjusting the pH value of the fatty alcohol-polyoxyethylene ether triethanolamine sulfate salt containing amino acid groups to 6.5-7 by using amino acid to obtain the product.
In particular, the fatty alcohol is represented by R1Is represented by R1Is one selected from C10-C18.
In particular, the amino acid is represented by R2COOH represents R2Is selected from CH3-CH(NH2)-、HN＝C(NH2)-NH-(CH2)3-CH(NH2)-、H2N-CO-CH2-CH(NH2)-、HOOC-CH2-CH(NH2)-、HS-CH2-CH(NH2)-、H2N-CO-(CH2)2-CH(NH2)-、HOOC-(CH2)2-CH(NH2)-、NH2-CH2-、NH-CH＝N-CH＝C-CH2-CH(NH2)-、CH3-CH2-CH(CH3)-CH(NH2)-、(CH3)2-CH-CH2-CH(NH2)-、H2N-(CH2)4-CH(NH2)-、CH3-S-(CH2)2-CH(NH2)-、Ph-CH2-CH(NH2)-、NH-(CH2)3-CH-、HO-CH2-CH(NH2)-、CH3-CH(OH)-CH(NH2)-、Ph-NH-CH＝C-CH2-CH(NH2)-、HO-p-Ph-CH2-CH(NH2)-、(CH3)2-CH-CH(NH2) -one or more of (a) and (b).
Specifically, the vacuum degree in the vacuumizing process is 0.5-2.5 Pa.
Specifically, the triethanolamine aqueous solution is a triethanolamine aqueous solution with a mass fraction of 30%.
The invention has the beneficial effects that:
according to the production method of the fatty alcohol-polyoxyethylene ether triethanolamine sulfate salt containing the amino acid groups, the reaction steps are adjusted, and the amino acid is added in the reaction process, so that the amino acid groups are introduced into the fatty alcohol-polyoxyethylene ether triethanolamine sulfate salt product, and the amino acid groups have the characteristics of hydrophilicity and lipophobicity, so that the oil removal performance of the product can be improved, the operation is simple, and the production cost is low.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments in order to provide a further understanding of the nature and technical means of the invention, as well as the specific objects and functions attained by the invention.
Example 1
A production method of fatty alcohol-polyoxyethylene ether sulfuric triethanolamine salt containing amino acid groups comprises the following steps:
s1, adding fatty alcohol-polyoxyethylene ether into a reaction container, preheating to 25-27 ℃, slowly adding chlorosulfonic acid while stirring, wherein the reaction time is 2.5-3.5 h, simultaneously, continuously vacuumizing in the reaction process, and the vacuum degree is 0.5-2.5 Pa in the vacuumizing process to remove hydrochloric acid generated by the reaction, wherein in order to enable the fatty alcohol-polyoxyethylene ether to completely react, the molar mass ratio of the fatty alcohol-polyoxyethylene ether to the chlorosulfonic acid is 1: 1.05-1.1.
The main reaction process is as follows:
s2, raising the temperature to 38-42 ℃, adding 30% triethanolamine aqueous solution for neutralization reaction for 1.5-2 h, wherein in order to introduce amino acid groups in the subsequent reaction, the molar mass ratio of triethanolamine to fatty alcohol-polyoxyethylene ether is 0.5-0.8: 1.
The main reaction process is as follows:
however, in the above reaction process, since the molar mass ratio of triethanolamine to fatty alcohol-polyoxyethylene ether is less than 1, one, two or three hydroxyl groups in the triethanolamine in the obtained product do not react, that is, the following side reactions, only some of which are listed below, occur.
The reaction process of the first side reaction is as follows:
the reaction process of the side reaction II is as follows:
the reaction process of the side reaction III is as follows:
s3, raising the temperature to 50-55 ℃, adding amino acid for further neutralization reaction for 1.5-2 h to obtain the fatty alcohol-polyoxyethylene ether triethanolamine sulfate containing amino acid groups, wherein the molar mass ratio of the amino acid to the fatty alcohol-polyoxyethylene ether is 0.25-0.55: 1, and the obtained side reaction product continues to further neutralize with the amino acid, so that the following subsequent reaction is carried out, and only part of the following subsequent reactions are listed.
The reaction process of the subsequent reaction I is as follows:
the reaction process of the subsequent reaction II is as follows:
the reaction process of the subsequent reaction III is as follows:
s4, adjusting the pH value of the fatty alcohol-polyoxyethylene ether triethanolamine sulfate salt containing amino acid groups to 6.5-7 by using amino acids to remove unreacted hydroxyl groups, and obtaining the product.
In the above reaction, n is an integer of 1 or more.
In the above reaction, the fatty alcohol is represented by R1Is represented by R1Is one selected from C10-C18.
In the above reaction, the amino acid may be selected fromOne or more of alanine, arginine, asparagine, aspartic acid, methionine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine and valine, wherein corresponding amino acid is R2COOH represents R2Is selected from CH3-CH(NH2)-、HN＝C(NH2)-NH-(CH2)3-CH(NH2)-、H2N-CO-CH2-CH(NH2)-、HOOC-CH2-CH(NH2)-、HS-CH2-CH(NH2)-、H2N-CO-(CH2)2-CH(NH2)-、HOOC-(CH2)2-CH(NH2)-、NH2-CH2-、NH-CH＝N-CH＝C-CH2-CH(NH2)-、CH3-CH2-CH(CH3)-CH(NH2)-、(CH3)2-CH-CH2-CH(NH2)-、H2N-(CH2)4-CH(NH2)-、CH3-S-(CH2)2-CH(NH2)-、Ph-CH2-CH(NH2)-、NH-(CH2)3-CH-、HO-CH2-CH(NH2)-、CH3-CH(OH)-CH(NH2)-、Ph-NH-CH＝C-CH2-CH(NH2)-、HO-p-Ph-CH2-CH(NH2)-、(CH3)2-CH-CH(NH2) -one or more of (a) and (b).
The above examples only show 1 embodiment of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (5)
1. A production method of fatty alcohol-polyoxyethylene ether sulfate triethanolamine salt containing amino acid groups is characterized by comprising the following steps:
s1, adding fatty alcohol-polyoxyethylene ether into a reaction container, preheating to 25-27 ℃, slowly adding chlorosulfonic acid while stirring, wherein the reaction time is 2.5-3.5 hours, and simultaneously continuously vacuumizing in the reaction process to remove hydrochloric acid generated by the reaction, wherein the molar mass ratio of the fatty alcohol-polyoxyethylene ether to the chlorosulfonic acid is 1: 1.05-1.1;
s2, raising the temperature to 38-42 ℃, adding a triethanolamine aqueous solution for a neutralization reaction for 1.5-2 hours, wherein the molar mass ratio of triethanolamine to fatty alcohol-polyoxyethylene ether is 0.5-0.8: 1;
s3, raising the temperature to 50-55 ℃, adding amino acid for further neutralization reaction for 1.5-2 h to obtain fatty alcohol polyoxyethylene ether triethanolamine sulfate containing amino acid groups, wherein the molar mass ratio of the amino acid to the fatty alcohol polyoxyethylene ether is 0.25-0.55: 1;
s4, adjusting the pH value of the fatty alcohol-polyoxyethylene ether triethanolamine sulfate salt containing amino acid groups to 6.5-7 by using amino acid to obtain the product.
2. The method for producing the fatty alcohol-polyoxyethylene ether triethanolamine sulfate according to claim 1, wherein the fatty alcohol is represented by R1Is represented by R1Is one selected from C10-C18.
3. The method for producing the fatty alcohol-polyoxyethylene ether triethanolamine sulfate according to claim 1, wherein the amino acid is represented by R2COOH represents R2Is selected from CH3-CH(NH2)-、HN＝C(NH2)-NH-(CH2)3-CH(NH2)-、H2N-CO-CH2-CH(NH2)-、HOOC-CH2-CH(NH2)-、HS-CH2-CH(NH2)-、H2N-CO-(CH2)2-CH(NH2)-、HOOC-(CH2)2-CH(NH2)-、NH2-CH2-、NH-CH＝N-CH＝C-CH2-CH(NH2)-、CH3-CH2-CH(CH3)-CH(NH2)-、(CH3)2-CH-CH2-CH(NH2)-、H2N-(CH2)4-CH(NH2)-、CH3-S-(CH2)2-CH(NH2)-、Ph-CH2-CH(NH2)-、NH-(CH2)3-CH-、HO-CH2-CH(NH2)-、CH3-CH(OH)-CH(NH2)-、Ph-NH-CH＝C-CH2-CH(NH2)-、HO-p-Ph-CH2-CH(NH2)-、(CH3)2-CH-CH(NH2) -one or more of (a) and (b).
4. The method for producing the fatty alcohol-polyoxyethylene ether triethanolamine sulfate containing amino acid groups according to claim 1, wherein the degree of vacuum in the vacuum pumping process is 0.5 to 2.5 Pa.
5. The method for producing the fatty alcohol-polyoxyethylene ether triethanolamine sulfate according to claim 1, wherein the aqueous solution of triethanolamine is 30% by weight.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111732525A (en) * | 2020-07-31 | 2020-10-02 | 湖南丽臣奥威实业有限公司 | Method for preparing non-aqueous system fatty alcohol ether sulfuric acid organic alkanolamine salt product |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111732525A (en) * | 2020-07-31 | 2020-10-02 | 湖南丽臣奥威实业有限公司 | Method for preparing non-aqueous system fatty alcohol ether sulfuric acid organic alkanolamine salt product |
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