CN109369475A - A kind of preparation method of double taurine based surfactants - Google Patents
A kind of preparation method of double taurine based surfactants Download PDFInfo
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- CN109369475A CN109369475A CN201811492416.4A CN201811492416A CN109369475A CN 109369475 A CN109369475 A CN 109369475A CN 201811492416 A CN201811492416 A CN 201811492416A CN 109369475 A CN109369475 A CN 109369475A
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- taurine
- methyltaurine
- reaction
- fatty alcohol
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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
- C07C303/22—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 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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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
- C07C303/32—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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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
Abstract
The present invention relates to a kind of preparation methods of double taurine based surfactants.Specially a kind of method for synthesizing long-chain ester group taurine N-methyltaurine surfactant, belongs to surfactant preparation technical field.The present invention is from MOLECULE DESIGN, reaction raw materials are in optimized selection, acyl chlorides raw material poisonous and harmful, that risk is big has been abandoned, and select mild fatty alcohol, product is obtained by esterification and sulfonating reaction, poisonous and hazardous solvent is not used simultaneously, and equipment is simple, easy to operate, reaction condition is mild, it is easily industrialized production, obtained product can also change its hydrophilic and oleophilic ability, superior performance according to actual needs.
Description
Technical field
The present invention relates to a kind of preparation methods of double taurine based surfactants.Specially a kind of synthesis long-chain ester group ox
The method of sulfonic acid methyl taurine surfactant.
Background technique
Taurine (Taurine) is also known as β-aminoethanesulfonic acid, earliest by separating in cow-bezoar, therefore gains the name, and is a kind of non-
Argine Monohydrochloride is also widely present in human body, closely related with the metabolism of human body；N methyl taurine is taurine ammonia
Hydrogen atom on base has the property similar with taurine by methyl substituted product, so containing taurine and methyl ox sulphur
The surfactant of acid has preferable compatibility with human body, and degreasing power is mild, and skin irritation is small, applied to washing for hair
Low to the fissility of hair cuticula when washing, irritation is low, and residual is few, and can inhibit the generation of dandruff.Currently on the market
Such surfactant has good biological degradability and a safety mainly based on fatty acyl group N-methyltaurine, hypotoxicity,
Low irritant, stronger foaming power extremely soft to skin have frank sense after washing, do not have thick existing for conventional washing agent
Astringent sense and slippery feeling, resistance to hard water are the primary raw materials of high-grade shampoo and shower cream.But the practice for passing through people finds have
Double taurine based surfactants of taurine N-methyltaurine have more powerful performance advantage, so-called double taurine bases
Surfactant is exactly the surfactant containing taurine and N-methyltaurine structure simultaneously in the molecular structure, such table
Face activating agent is due to weak cationic characteristic, so that product has certain hair conditioning, simultaneously as cationic weaker, institute
Not will increase its irritation, the characteristics of being provided with a kind of unique amphoteric surfactant instead, thus in terms of mildness,
More traditional fatty acyl group N-methyltaurine sodium has impayable advantage, especially such table activating agent and other class surfaces
Activating agent compound property is excellent, while can also reduce the irritation of other surfaces activating agent, improves the mildness of formula, thus quilt
It is widely used in shampoo, facial cleanser, bath oil, soap, detergent, shaving cream, toothpaste and industrial products.
The long chain hydrophobic group of double taurine surfactants of taurine N-methyltaurine class is amide structure at present, such
Surfactant is generally made by two methods of direct method and indirect method, and direct method is with fatty acid or aliphatic ester and N- methyl
Sodium taurocholate/sodium taurocholate carries out the technique of condensation reaction, is all fat as described in CN105175290A, CN106588710A
Acid is condensed with N- acyl taurines；Indirect rule is mainly Xiao Dun-Bao Man reaction process, it is hydrolyzing either acylated with Arneel SD
It is synthesized under basic catalyst effect at fat acyl chloride, fat acyl chloride and N methyl taurine sodium, such as
All technique thus described in CN102875422, CN207031310U, CN1680305A.
Direct synthesis fatty acyl group N-methyltaurine/sodium taurocholate, required equipment is complex, and nitrogen is needed to protect
Shield, solvent type reaction need separating-purifying, even if solvent recovery cycle utilizes, also will cause pressure to environment；No-solvent type is anti-
Then higher device should be needed to require, and yield is lower.Indirect method synthctic fat sulfonylmethyl sodium taurocholate/sodium taurocholate needs to use
To fat acyl chloride, fat acyl chloride is larger to the harm of environment, safety, belongs to hazardous chemical, is more toxic.
Summary of the invention
In order to improve the synthetic method of the double taurine surfactants of taurine N-methyltaurine class, solving synthesis process makes
Raw material environmental pollution and the excessive problem of human injury, the present invention provide a kind of novel taurine N-methyltaurine class
Double taurine surfactant preparation methods, it is characterised in that with maleic anhydride, fatty alcohol, taurine, N-methyltaurine
Sodium (40%), 32% liquid alkaline are raw material, are obtained by esterification, sulfonating reaction, and this method is easy to get with raw material, rational technology,
Feature easy to operate.
In order to achieve the above objectives, the present invention adopts the following technical scheme:
(1) check that synthesis reaction vessel cleans up, dry anhydrous, temperature in the kettle≤40 DEG C；
(2) maleic anhydride is put into reaction kettle, is to slowly warm up to 60~70 DEG C of temperature, watery fusion, to material
After melting, stirring, 50~60RPM of revolving speed are started；
(3) fatty alcohol of liquid condition is squeezed into reaction kettle, nitrogen is replaced 2~3 times；It opens steam and is warming up to 70~90
DEG C, and insulation reaction 2~6 hours at such a temperature, then it is cooled to 60~70 DEG C；
(4) under stirring, it is slowly added to the hydroxide for the taurine N-methyltaurine that mass percent is 20~25% contents
Sodium solution, is added speed control in 30~60min, and process temperature control is at 70~100 DEG C, pH=8~10；
(5) after the completion of being added, continue 70~100 DEG C insulation reaction 2~10 hours, to system acid value≤10mgKOH/g, stop
It only reacts, adjusts system pH=5~7, the finished product of blowing.
The obtained product has the following structure:
It is H or CH3 that wherein R1, which is R3,；R2 is the straight chain or branched alkyl of the saturation with 8~16 carbon atoms.
The molar ratio of the maleic anhydride and fatty alcohol is 1:1.05.
The fatty alcohol is one or more of C8~C16.
The molar ratio of the maleic anhydride and taurine N-methyltaurine is 1:1.05~3.0.
Taurine percentage ratio is 0.1~99.9 in the taurine N-methyltaurine.
Acid value≤10mgKOH/g of the product.
Compared with prior art, the present invention having the advantages that following prominent and good effect:
The present invention is in optimized selection reaction raw materials from MOLECULE DESIGN, and it is big to have abandoned poisonous and harmful, risk
Acyl chlorides raw material, and mild fatty alcohol is selected, product is obtained by esterification and sulfonating reaction, while without using poisonous and hazardous
Solvent, equipment is simple, easy to operate, and reaction condition is mild, it is easy to accomplish industrialized production, obtained product also can be according to reality
Demand changes its hydrophilic and oleophilic ability, superior performance.
Specific embodiment
The present invention will be further described below with reference to examples, but should not be limited the scope of the invention with this.
Embodiment 1
It checks that taurine N-methyltaurine head tank can be used for feeding intake, puts into the deionized water of 1330kg, stir lower throw
Enter the taurine of 450kg, the N-methyltaurine sodium (40%) of 60kg, it is equal to stir mixing in 1~2 hour for 32% liquid alkaline of 450kg
It is even, for use.
Check that synthesis reaction vessel cleans up, dry anhydrous, temperature in the kettle≤40 DEG C；350kg maleic anhydride is thrown
Entering in reaction kettle, is to slowly warm up to 60~70 DEG C of temperature, watery fusion starts stirring after material melts, revolving speed 50~
60RPM；
The 664kg lauryl alcohol of bakingization is squeezed into reaction kettle, nitrogen is replaced 2~3 times；It opens steam and is warming up to 75 DEG C, close
Steam, temperature is increased to 85 DEG C within about 0.5 hour；It is adjusted by steam, so that reaction temperature control at 85 DEG C, under stirring, is kept the temperature
Reaction 2.5 hours, is then cooled to 70 DEG C；
Under stirring, it is slowly added to the sodium hydroxide solution for the taurine N-methyltaurine that front prepares, by ox in 30min
The sodium hydroxide solution addition of sulfonic acid methyl taurine finishes, and process temperature control is at 85 DEG C, pH=9~10；
After the completion of the sodium hydroxide solution of taurine N-methyltaurine is added, continue 85 DEG C of insulation reactions 3 hours, middle control body
It is acid value 5.6mgKOH/g, stops reaction, adjust system pH=6.5, blowing obtains finished product.
Claims (7)
1. a kind of preparation method of double taurine based surfactants, it is characterised in that adopt the following technical scheme that obtained:
(1) check that synthesis reaction vessel cleans up, dry anhydrous, temperature in the kettle≤40 DEG C；
(2) maleic anhydride is put into reaction kettle, is to slowly warm up to 60~70 DEG C of temperature, watery fusion, to material melts
Afterwards, stirring, 50~60RPM of revolving speed are started；
(3) fatty alcohol of liquid condition is squeezed into reaction kettle, nitrogen is replaced 2~3 times；It opens steam and is warming up to 70~90 DEG C, and
Then insulation reaction 2~6 hours at such a temperature are cooled to 60~70 DEG C；
(4) under stirring, it is slowly added to the sodium hydroxide solution of the taurine N-methyltaurine of 20~25% contents, speed control is added
System is in 30~60min, and process temperature control is at 70~100 DEG C, pH=8~10；
(5) after the completion of being added, continue 70~100 DEG C insulation reaction 2~10 hours, to system acid value≤10mgKOH/g, stop anti-
It answers, adjusts system pH=5~7, the finished product of blowing.
2. obtained product has the following structure as described in claim 1:
It is H or CH3 that wherein R1, which is R3,；R2 is the straight chain or branched alkyl of the saturation with 8~16 carbon atoms.
3. the molar ratio of maleic anhydride as described in claim 1 and fatty alcohol is 1:1.05.
4. the fatty alcohol is one or more of C8~C16.
5. the molar ratio of maleic anhydride as described in claim 1 and taurine N-methyltaurine is 1:1.05~3.0.
6. taurine percentage ratio is 0.1~99.9 in taurine N-methyltaurine as described in claim 1.
7. acid value≤10mgKOH/g of product as described in claim 1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811492416.4A CN109369475A (en) | 2018-12-07 | 2018-12-07 | A kind of preparation method of double taurine based surfactants |
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| CN201811492416.4A CN109369475A (en) | 2018-12-07 | 2018-12-07 | A kind of preparation method of double taurine based surfactants |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004157A (en) * | 2019-12-23 | 2020-04-14 | 张家港格瑞特化学有限公司 | Preparation method of acyl amino acid surfactant containing ester group |
| CN111072524A (en) * | 2019-12-23 | 2020-04-28 | 张家港格瑞特化学有限公司 | Method for preparing fatty acyl amino acid surfactant by adopting high-temperature crystallization |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102126984A (en) * | 2010-12-30 | 2011-07-20 | 上海奥利实业有限公司 | Condensation production process and special device of N-long-chain acyl amino acid salt |
| CN103752210A (en) * | 2014-01-22 | 2014-04-30 | 湖南师范大学 | Monosuccinate amino acid surfactant containing functionalized amino group and preparation method of surfactant |
| CN106631919A (en) * | 2015-10-29 | 2017-05-10 | 中国石油天然气股份有限公司 | Branched chain sodium taurate surfactant, preparation method and applications thereof |
-
2018
- 2018-12-07 CN CN201811492416.4A patent/CN109369475A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102126984A (en) * | 2010-12-30 | 2011-07-20 | 上海奥利实业有限公司 | Condensation production process and special device of N-long-chain acyl amino acid salt |
| CN103752210A (en) * | 2014-01-22 | 2014-04-30 | 湖南师范大学 | Monosuccinate amino acid surfactant containing functionalized amino group and preparation method of surfactant |
| CN106631919A (en) * | 2015-10-29 | 2017-05-10 | 中国石油天然气股份有限公司 | Branched chain sodium taurate surfactant, preparation method and applications thereof |
Non-Patent Citations (2)
| Title |
|---|
| QI YAN ET AL.: "Near-instant surface-selective fluorogenic protein", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 * |
| 乔卫红等: "一种富马酸类可聚合乳化剂的合成及其乳液性能研究", 《精细化工》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004157A (en) * | 2019-12-23 | 2020-04-14 | 张家港格瑞特化学有限公司 | Preparation method of acyl amino acid surfactant containing ester group |
| CN111072524A (en) * | 2019-12-23 | 2020-04-28 | 张家港格瑞特化学有限公司 | Method for preparing fatty acyl amino acid surfactant by adopting high-temperature crystallization |
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