CN108358802A - A kind of preparation method of fat acidyl glycine salt surfactant - Google Patents
A kind of preparation method of fat acidyl glycine salt surfactant Download PDFInfo
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- CN108358802A CN108358802A CN201810010563.7A CN201810010563A CN108358802A CN 108358802 A CN108358802 A CN 108358802A CN 201810010563 A CN201810010563 A CN 201810010563A CN 108358802 A CN108358802 A CN 108358802A
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- 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
Abstract
The present invention relates to a kind of preparation methods of fat acidyl glycine salt surfactant.Step is：It is first 1 by molar ratio:2~5 grease is added to amino-acid salt in reactor；The reactor mating need to be provided with heating system and external circulating system；Secondly it after catalyst is added needs that solid-liquid heterogeneous reaction system adequately shear and stir；Then, heating response device heating controls reaction temperature at 130 DEG C~190 DEG C, and reaction carries out 2~8 hours；Reaction temperature is finally cooled to 60~90 DEG C, neutralizer is added, pH value is adjusted to 7~8, obtains product；Measure fat-based amino-acid salt content, product yield.The present invention is with technique green is simple and direct, reaction condition is mild, synthesis under normal pressure is easy to operate, is easily industrialized production, product purity is high, at low cost and eco-friendly, and good surface activity, synthesis is raw materials used to be easy to get, the advantages such as production process cleanliness without any pollution.
Description
Technical field
The invention belongs to organic compound synthesis technical fields, and in particular to a kind of fat acidyl glycine salt surface-active
The preparation method of agent.
Technical background
The sweet amino acid surfactant of acyl group be by soaps carry out structure of modification prepared by, be common soap more
New regeneration product is the mild surfactants of a protein species, since reactant used in synthesis is all the structure of organism
At part, there is good biocompatibility and biological degradability, safe.And with excellent hard water resistance property, chelating
Functions, the especially low irritant such as property, inhibition rust-preventing characteristic, biocidal property, hypotoxicity, mildness and to preferable compatibility of human body etc.
Feature becomes the hot spot of surfactant field research application and commercialization.
Acylglycine class surfactant is the quality raw materials of detergent and personal cleanliness's articles for use, is suitable for preparing high-grade
Soap, skin care item, shampoo, bath foam, mildy wash, hand cleanser, toothpaste etc., product acid-base property is moderate, keeps skin thoughts and feelings comfortable, soft and smooth,
And, irritation is low, safe to use to skin action temperature；It is especially compounded with soaps, improves the stability in hard water and water solubility of product,
And it can effectively reduce the irritation of soap base in formula.Acylglycine class surfactant can also be used for medicine, food additives
Etc. in industries.
Up to the present, the preparation of acyl amino acid surfactant has chloride method, fatty acid anhydride method, Arneel SD hydrolysis
Method, amide carbonylation method, enzyme process etc..Though fatty acid anhydride method, Arneel SD Hydrolyze method, amide carbonylation method, enzyme process these four methods
There is research more, but since there are various disadvantages, does not obtain industrial application.Industrially produce such surfactant at present
Method be chloride method, this synthetic method use Xiao Dun-Bao Man（Schotlen-Banmann）Condensation reaction.
And using this technique due to the use of having strong corrosive and irritating raw material, such as phosphorus trichloride or thionyl chloride and
Fat acyl chloride, environmental pollution is serious, higher to equipment requirement.It is and very high to acyl chlorides quality requirement in condensation, it is necessary to completely cut off
Moisture is stored, and to reduce its hydrolysis, after otherwise hydrolysate introduces product, removing is extremely difficult, and also by-product is more, produces
Product shade deviation simultaneously has the shortcomings that peculiar smell, limits application of the product in the fields such as food, medicine and cosmetics.And to acyl chlorides
Quality requirement is very high, has the shortcomings that by-product is more, product color is poor, has peculiar smell, to limit product in food, medicine and change
Application in the fields such as cosmetic.
Invention content
The object of the invention is that in view of the deficiencies of the prior art and provides a kind of fat acidyl glycine salt surface-active
The preparation method of agent, with technique green is simple and direct, reaction condition is mild, synthesis under normal pressure is easy to operate, is easily industrialized life
Production, product purity is high, at low cost and eco-friendly, and good surface activity, and synthesis is raw materials used to be easy to get, and production process cleans
The advantages such as pollution-free are a kind of very promising new synthetic methods.
Realize that the technical solution of above-mentioned purpose of the present invention is：
A kind of preparation method of fat acidyl glycine salt surfactant of the present invention, method and step are as follows：
It is first 1 by molar ratio:2~5 grease is added to amino-acid salt in reactor；The reactor needs mating setting
There are heating system and external circulating system；
Secondly it after catalyst is added needs that solid-liquid heterogeneous reaction system adequately shear and stir；Then, it heats
Reactor heating controls reaction temperature at 130 DEG C~190 DEG C（These technological parameters include following respectively marking red parameter and preferably becoming
Change, preferably and present parameter area is different）, reaction progress 2~8 hours；
Reaction temperature is finally cooled to 60~90 DEG C, neutralizer is added, pH value is adjusted to 7~8, obtains product；Measure grease
Base amino-acid salt content, product yield.
Catalyst of the present invention is the single or mixture of pyrovinic acid, metilsulfate.The addition of catalyst
For the 0.1wt%-0.5wt% of reactant；The neutralizer is one or both of citric acid, ethylenediamine tetra-acetic acid, phosphoric acid
The above mixture.
Grease provided by the present invention can be vegetable fat, have soya-bean oil, corn oil, cottonseed oil, coconut oil, palm oil,
Brown paulownia benevolence oil, castor oil, rice bran oil, olive oil or ethereal fruit oil etc.；It may be animal fat, there is butter, sheep oil, lard, skin
Oil or animal oil etc..
Amino-acid salt provided by the invention can be sarcosine, glutamic acid, alanine, leucine, isoleucine, sweet ammonia
The metal salt of acid, proline, lysine, serine, arginine etc. or organic ammonia salt, preferably sodium salt or sylvite.
Beneficial effects of the present invention are：
（1）The present invention substitutes traditional raw material with green material and designs and develops the technology of clean and effective using new exclusive catalyst
It is prepared by route, the green for realizing N-fat acidyl glycine salt.Present invention process according to the boiling point of grease and amino-acid salt,
Fusing point and thermal stability select suitable molar ratio and reaction temperature, improve substrate grease conversion ratio, reduce the viscous of reactant
Degree increases mass-transfer efficiency, reduces the color and luster of product.
（2）Efficient special-purpose catalyst induced reaction technology；
Since reactant reaction cardinal principle is by the dissolving of reaction mass grease, the mixing to reach solid liquid phase has come
At catalyst increases heterogeneous contact surface at a certain temperature, accelerates reaction speed by induced reaction, reduces side reaction
The generation of glycinate improves target product yield.
（3）Using the stirring technique of shearing and stirring simultaneously for solid-liquid phase System Design, adequately shearing and stirring
It can make to be contacted well between reactant, solve high viscosity and multiphase（It is heterogeneous）Mass transfer, heat transfer and the reaction speed of system
Degree can also make reaction temperature uniformly or export reaction heat in time, be conducive to reaction and carry out, shorten the reaction time.It is same to increase
External circulating system and increase the measures such as external heating system, make glycinate be not easy to be deposited on reactor bottom form dead angle and
Coking substantially increases mass transfer, the heat-transfer effect of solid-liquid two-phase, accelerates reaction speed, shorten the reaction time.
Specific implementation mode
The present invention is further explained in the light of specific embodiments：
Embodiment 1：
0.1mol coconut oil and 0.35mol sodium glutamates are added to the normal pressure reactor with heating, stirring and register
In, add the sodium methanesulfonate of the 0.3wt% of reactant（Catalyst）, 140 DEG C are gradually heating to after being sufficiently stirred, reaction 5
Hour, 80 DEG C of citric acids for being incorporated as reactant weight 0.08wt% are cooled to, pH value 7~8 is adjusted, reaction terminates to be produced
Product.Finally measure material Glutamic Acid sodium content 0.3%, product N- sodium cocoyl glutamates yield 98.7%.
Embodiment 2：
0.1mol lauric acid and 0.12mol potassium glutamates are added to the normal pressure reactor with heating, stirring and register
In, add the pyrovinic acid potassium of the 0.2wt% of reactant（Catalyst）, 150 DEG C are gradually heating to after being sufficiently stirred, reaction 5
Hour, 80 DEG C of citric acids for being incorporated as reactant weight 0.05wt% are cooled to, pH value 7~8 is adjusted, reaction terminates to be produced
Product.Measure material Glutamic Acid potassium content 0.2%, product lauroyl glutamate potassium yield 99.2%.
Embodiment 3：
0.1mol palm oils and 0.33mol sodium sarcosinates are added to the normal pressure reactor with heating, stirring and register
In, add the pyrovinic acid of the 0.2wt% of reactant（Catalyst）, 150 DEG C are gradually heating to after being sufficiently stirred, reaction 6 is small
When, 70 DEG C of ethylenediamine tetra-acetic acids for being incorporated as reactant weight 0.03wt% are cooled to, pH value 7~8 is adjusted, reaction terminates to obtain
Product.Measure sodium sarcosinate content 0.2% in material, product N- palm oil-base sodium sarcosinates yield 99.0%.
It is chloride method preparation process and preparation process contrast table of the present invention below
As can be seen from the above table, the preparation method industrially commonly used is chloride method, which reacts for two-step method, from acyl chlorides
To have prepared for flow be considerably long；Severe reaction conditions need nitrogen protection, complex process；Conversion ratio only reaches
75%；Product yield is low；Raw material PCl3 is needed in reaction process（Or SOCl2）Irritation is big；There are HCl generations in production process, corrodes
Property it is big, generating a large amount of spent acid needs to handle, and operating procedure is complicated, there are environmental pollutions；And in condensation to acyl chlorides quality requirement
It is very high, it is necessary to completely cut off moisture storage, to reduce its hydrolysis, after otherwise hydrolysate introduces product, removing is extremely difficult, but also
Have the shortcomings that by-product is more, product color is poor and has peculiar smell, limits product answering in the fields such as food, medicine and cosmetics
With being only used for washing and metal-working industry, use scope is restricted.
Preparation method of the present invention has the following advantages compared with chloride method：The technique is the direct amidation condensation of one-step method
Reaction, technological process are short；Reaction condition is mild, is not required to nitrogen protection, and synthesis under normal pressure is simple for process；Conversion ratio is only up to 98%；
Product yield is high；Synthesize it is raw materials used be easy to get, production process cleanliness without any pollution；Products obtained therefrom purity is high, product color is shallow, surface
Activity is good, mild safe, is widely used in cosmetics, detergent, food additives, intermetallic composite coating, oil exploitation, biology
The various fields such as product and medicine preparation.
Claims (5)
1. a kind of preparation method of fat acidyl glycine salt surfactant, it is characterised in that：Steps are as follows for this method：
It is first 1 by molar ratio:2~5 grease is added to amino-acid salt in reactor；The reactor needs mating setting
There are heating system and external circulating system；
Secondly it after catalyst is added needs that solid-liquid heterogeneous reaction system adequately shear and stir；
Then, heating response device heats up and controls reaction temperature at 130 DEG C~190 DEG C, and reaction carries out 2~8 hours；
Reaction temperature is finally cooled to 60~90 DEG C, appropriate neutralizer is added, pH value is adjusted to 7~8, obtains product；It measures
Fat-based amino-acid salt content, product yield.
2. a kind of preparation method of fat acidyl glycine salt surfactant according to claim 1, it is characterised in that：
The catalyst is the single or mixture of pyrovinic acid, metilsulfate；The addition of catalyst is reactant
0.1wt%-0.5wt%。
3. a kind of preparation method of fat acidyl glycine salt surfactant according to claim 1, it is characterised in that：
The neutralizer is one or more of citric acid, ethylenediamine tetra-acetic acid, phosphoric acid mixture.
4. a kind of preparation method of fat-based amino-acid salt series of surfactants according to claim 1, feature exist
In：Grease is vegetable fat, have soya-bean oil, corn oil, cottonseed oil, coconut oil, palm oil, brown paulownia benevolence oil, castor oil, rice bran oil,
One of olive oil or ethereal fruit oil；Or be animal fat, there are one of butter, sheep oil, lard, skin oil or animal oil；
The amino-acid salt be sarcosine, glutamic acid, alanine, leucine, isoleucine, glycine, proline, lysine,
One of serine, arginic metal salt or one of organic ammonia salt.
5. a kind of preparation method of fat-based amino-acid salt series of surfactants according to claim 4, feature exist
In：The amino-acid salt is sodium salt or sylvite.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810010563.7A CN108358802A (en) | 2018-01-05 | 2018-01-05 | A kind of preparation method of fat acidyl glycine salt surfactant |
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| CN201810010563.7A CN108358802A (en) | 2018-01-05 | 2018-01-05 | A kind of preparation method of fat acidyl glycine salt surfactant |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262276A (en) * | 2021-12-28 | 2022-04-01 | 赞宇科技集团股份有限公司 | Method for directly synthesizing fatty acyl alanine salt from fatty acid |
| CN114621833A (en) * | 2022-03-08 | 2022-06-14 | 河北源清环保科技有限公司 | Liquid phosphorus-free alkaline membrane cleaning agent and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102266737A (en) * | 2011-06-16 | 2011-12-07 | 北京工商大学 | Method for preparing N-fatty acyl amino acid type surfactant by fat |
| DE102011107503A1 (en) * | 2011-07-15 | 2012-03-01 | Clariant International Ltd. | Preparing acylglycinate compound useful in a composition, which is used as a surfactant in a cosmetic preparation, comprises reacting glycine with fatty acid chloride in water and in the presence of a basic alkali metal compound |
| CN103772227A (en) * | 2014-01-13 | 2014-05-07 | 石家庄菠莉亚日用化工有限公司 | Preparation method for grease-based amino acid salt-series surfactant |
| CN104607098A (en) * | 2015-01-30 | 2015-05-13 | 北京工商大学 | Method for preparing grease acyl sodium leucine and surface active agent composition containing grease acyl sodium leucine in phase-transfer catalysis way |
| CN104607097A (en) * | 2015-01-30 | 2015-05-13 | 北京工商大学 | Method for preparing oil-acyl lysine sodium and composition comprising surfactant through phase-transfer catalysis |
-
2018
- 2018-01-05 CN CN201810010563.7A patent/CN108358802A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102266737A (en) * | 2011-06-16 | 2011-12-07 | 北京工商大学 | Method for preparing N-fatty acyl amino acid type surfactant by fat |
| DE102011107503A1 (en) * | 2011-07-15 | 2012-03-01 | Clariant International Ltd. | Preparing acylglycinate compound useful in a composition, which is used as a surfactant in a cosmetic preparation, comprises reacting glycine with fatty acid chloride in water and in the presence of a basic alkali metal compound |
| CN103772227A (en) * | 2014-01-13 | 2014-05-07 | 石家庄菠莉亚日用化工有限公司 | Preparation method for grease-based amino acid salt-series surfactant |
| CN104607098A (en) * | 2015-01-30 | 2015-05-13 | 北京工商大学 | Method for preparing grease acyl sodium leucine and surface active agent composition containing grease acyl sodium leucine in phase-transfer catalysis way |
| CN104607097A (en) * | 2015-01-30 | 2015-05-13 | 北京工商大学 | Method for preparing oil-acyl lysine sodium and composition comprising surfactant through phase-transfer catalysis |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262276A (en) * | 2021-12-28 | 2022-04-01 | 赞宇科技集团股份有限公司 | Method for directly synthesizing fatty acyl alanine salt from fatty acid |
| CN114621833A (en) * | 2022-03-08 | 2022-06-14 | 河北源清环保科技有限公司 | Liquid phosphorus-free alkaline membrane cleaning agent and preparation method thereof |
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Application publication date: 20180803 |
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