CN100391585C - Dialkyl glutamic surgar ester surfactant, prepn. method and use thereof - Google Patents
Dialkyl glutamic surgar ester surfactant, prepn. method and use thereof Download PDFInfo
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- CN100391585C CN100391585C CNB2005100192553A CN200510019255A CN100391585C CN 100391585 C CN100391585 C CN 100391585C CN B2005100192553 A CNB2005100192553 A CN B2005100192553A CN 200510019255 A CN200510019255 A CN 200510019255A CN 100391585 C CN100391585 C CN 100391585C
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Abstract
The present invention discloses a dialkyl glutamic surgar ester surfactant, a preparation method thereof and purposes thereof. In the method, firstly, a carbon fixated SnCl4 catalyst is manufactured, fatty alcohol and glutamic acid are mixed according to a certain proportion and added with a certain number of carbon fixated SnCl4 catalysts, and a solventliss mixing catalytic reaction is carried out for a certain time at the temperature of 110 to 130 DEG C.; the mixture is filtered, dehydrated, dissolved in acetone and added with a small amount of concentrated hydrochloric acid or hydrochloric acid gas for precipitation and recrystallization to obtain crystals, and the yield is more than or equal to 98 %; the crystals, gluconolactone and triethylamine are mixed and dissolved in ethyl alcohol according to a certain proportion and stirred for back flow for 2 hours, and the non-traditional dialkyl glutamic surgar ester surfactant is prepared with the yield of 85% through underpressure distillation and recrystallization. The surfactant has the advantages of favorable surface activity efficiency and amphiphilicbase group, can be dissolved in an organic solvent and has a wide application prospect in the fields of double-layer coating liquid films, enzyme immobilization, etc.
Description
Technical field
The present invention relates to a kind of dialkyl glutamic surgar ester surfactant and its production and use, belong to organic synthesis surfactant field.
Background technology
Shortcomings such as the catalyst that strong acid and strong base etc. has high corrosion to equipment is used in the preparation of traditional surfactant more, as the concentrated sulfuric acid etc., environment is seriously influenced, and the reaction complexity, and accessory substance is many, and post processing is loaded down with trivial details.With regard to synthetic, it is at Bc, and the character on the biodegradability is focus, the focus that people are concerned about always.Because the Bc of amino acid and derivative thereof is good, affinity is strong, environment friendly, and recyclability and cheap is that present people carry out biomolecule and free paying the utmost attention to of design preparation surfactant.There is data to show, had amino acid derivativges to be used for cosmetics abroad.But, in representing the building-up process of surface-active agent,, there is not suitable catalyst efficiently owing to do not solve the problem that solvent uses, still exist serious process to pollute.Therefore, the focus direction of a present research is to seek a kind of catalyst efficiently, the synthetic target product of catalysis in solvent-free system.
Summary of the invention
The present invention is directed to the problem of above-mentioned existence, a kind of reusable catalyst is provided, and can make to be reflected at and do not have solvent to have dialkyl glutamic surgar ester surfactant that carries out smoothly down and its production and use.It is cheap and easy to get to have raw material, and Preparation of Catalyst is easy, reacts clean soon, and post processing is simple, productive rate height, characteristics such as environmental pollution is less.
Technical scheme provided by the invention is to adopt following method to prepare dialkyl glutamic surgar ester surfactant:
(1) with active carbon and SnCl
45H
2O refluxes in the capacity absolute ethyl alcohol by 1: 0.5～1: 8 (mass ratio) and prepares the immobilized stannic chloride catalyst of active carbon;
(2) fatty alcohol and glutamic acid are mixed by 1: 2～1: 6 (amount of substance ratio);
(3) get the immobilized stannic chloride catalyst of 1%～15% (mass percent) active carbon and add in the mixed system of step (2),, divide water 110～130 ℃ of stirrings; Reaction finishes, and cooled and filtered reclaims catalyst, and filtrate use the anhydrous sodium sulfate dehydration drying, and moves in the acetone and dissolve, and to wherein dripping a small amount of concentrated hydrochloric acid or feeding hydrogen chloride gas, makes it form hydrochloride and precipitates, be recrystallized the white crystals thing;
(4) get above-mentioned white crystals thing and gluconolactone and mix by 1: 1～1: 6 (amount of substance than) and capacity triethylamine after, backflow made dialkyl glutamic surgar ester in 2 hours in the capacity absolute ethyl alcohol again.
The immobilized stannic chloride catalyst of above-mentioned active carbon is reusable.
Above-mentioned preparation process is used and is divided water to dewater, and is catalytic reaction in solvent-free system.
Above-mentioned glutamic acid is synthesis material.
Above-mentioned dialkyl glutamic surgar ester surfactant can be used for the modification of enzyme.
Main feature of the present invention is:
(1) the immobilized stannic chloride catalyst of the reusable active carbon of preparation, the expendable problem of solution catalyst;
(2) do not re-use benzene, toluene etc. have the solvent of severe contamination to environment, belong to solvent-free catalytic reaction;
(3) raw material is cheap and easy to get, and Preparation of Catalyst is easy, reacts clean soon, and post processing is simple, and reaction effect is good, the productive rate height.
(4) at the double-layer coatings liquid film, fields such as the immobilization of enzyme have broad application prospects.
The specific embodiment
Embodiment 1: get 100gSnCl
45H2O, the 50g active carbon, the 80ml absolute ethyl alcohol and stirring refluxes and makes the immobilized stannic chloride catalyst of active carbon; Get 29.43g glutamic acid, the 111.8g laruyl alcohol mixes, and adds 7% the immobilized tetrachloro catalyst of active carbon again, stirs catalytic reaction in 110 ℃ of following minute water; Cooling afterreaction product is used the anhydrous sodium sulfate dehydration drying, and is dissolved in acetone after filtration, drips a small amount of concentrated hydrochloric acid to acetone soln then and forms hydrochloride, recrystallization hydrochloride, productive rate 98%; With the 100g hydrochloride, the 53.4g gluconolactone after the 100ml triethylamine mixes, refluxed 2 hours at absolute ethyl alcohol again, obtained dialkyl glutamic surgar ester, productive rate 80%.
Embodiment 2: get 90gSnCl
45H2O, the 40g active carbon, the 40ml absolute ethyl alcohol and stirring refluxes and makes the immobilized stannic chloride catalyst of active carbon; Get 22.1g glutamic acid, the 83.9g laruyl alcohol mixes, and adds 6% the immobilized stannic chloride catalyst of active carbon, stirs catalytic reaction in 115 ℃ of following minute water; Cooling afterreaction product is used the anhydrous sodium sulfate dehydration drying, and is dissolved in acetone after filtration, drips a small amount of concentrated hydrochloric acid to acetone soln then and forms hydrochloride, recrystallization hydrochloride, productive rate 99%; With the 77.3g hydrochloride, the 40.1g gluconolactone after the 80ml triethylamine mixes, refluxed 2 hours at absolute ethyl alcohol again, obtained dialkyl glutamic surgar ester, productive rate 85%.
Embodiment 3: get 30gSnCl
45H2O, the 30g active carbon, the 20ml absolute ethyl alcohol and stirring refluxes and makes the immobilized stannic chloride catalyst of active carbon; Get 14.7g glutamic acid, the 55.9g laruyl alcohol mixes, and adds the immobilized stannic chloride catalyst of 5% active carbon, stirs catalytic reaction in 120 ℃ of following minute water; Cooling afterreaction product is used the anhydrous sodium sulfate dehydration drying, and is dissolved in acetone after filtration, drips a small amount of concentrated hydrochloric acid to acetone soln then and forms hydrochloride, recrystallization hydrochloride, productive rate 96%; With the 54g hydrochloride, the 44.5g gluconolactone after the 100ml triethylamine mixes, refluxed 2 hours at absolute ethyl alcohol again, obtained dialkyl glutamic surgar ester, productive rate 85%.
Embodiment 4: get 150gSnCl
45H
2O, the 50g active carbon, the 90ml absolute ethyl alcohol and stirring refluxes and makes the immobilized stannic chloride catalyst of active carbon; Get 73.6g glutamic acid, the 326.1g laruyl alcohol mixes, and adds the catalyst of the immobilized butter of tin of 11% active carbon, stirs catalytic reaction in 130 ℃ of following minute water; Cooling afterreaction product is used the anhydrous sodium sulfate dehydration drying, and is dissolved in acetone after filtration, drips a small amount of concentrated hydrochloric acid to acetone soln then and forms hydrochloride, recrystallization hydrochloride, productive rate 96%; With the 540g hydrochloride, the 142.1g gluconolactone after the 150ml triethylamine mixes, refluxed 2 hours at absolute ethyl alcohol again, obtained dialkyl glutamic surgar ester, productive rate 85%.
Claims (5)
1. dialkyl glutamic surgar ester surfactant is characterized in that making by the method for being prepared as follows:
(1) with active carbon and SnCl
45H
2O presses mass ratio 1: 0.5～1: 8 immobilized stannic chloride catalyst of preparation active carbon that in the capacity absolute ethyl alcohol, refluxes;
(2) fatty alcohol and glutamic acid are mixed than 1: 2～1: 6 by amount of substance;
(3) getting mass percent is that the immobilized stannic chloride catalyst of 1%～15% active carbon adds in the mixed system of step (2), 110～130 ℃ of stirrings, divides water to dewater; Reaction finishes, and cooled and filtered reclaims catalyst, and filtrate use the anhydrous sodium sulfate dehydration drying, and moves in the acetone and dissolve, and to wherein dripping a small amount of concentrated hydrochloric acid or feeding hydrogen chloride gas, makes it form hydrochloride and precipitates, be recrystallized the white crystals thing;
(4) get above-mentioned white crystals thing and gluconolactone and mix than 1: 1～1: 6 and capacity triethylamine by amount of substance after, in the capacity absolute ethyl alcohol, reflux again and made dialkyl glutamic surgar ester in 2 hours.
2. method for preparing dialkyl glutamic surgar ester surfactant is characterized in that preparation process is as follows:
(1) with active carbon and SnCl
45H
2O presses mass ratio 1: 0.5～1: 8 immobilized stannic chloride catalyst of preparation active carbon that in the capacity absolute ethyl alcohol, refluxes;
(2) fatty alcohol and glutamic acid are mixed than 1: 2～1: 6 by amount of substance;
(3) getting mass percent is that the immobilized stannic chloride catalyst of 1%～15% active carbon adds in the mixed system of step (2), 110～130 ℃ of stirrings, divides water to dewater; Reaction finishes, and cooled and filtered reclaims catalyst, and filtrate use the anhydrous sodium sulfate dehydration drying, and moves in the acetone and dissolve, and to wherein dripping a small amount of concentrated hydrochloric acid or feeding hydrogen chloride gas, makes it form hydrochloride and precipitates, be recrystallized the white crystals thing;
(4) get above-mentioned white crystals thing and gluconolactone and mix than 1: 1～1: 6 and capacity triethylamine by amount of substance after, in the capacity absolute ethyl alcohol, reflux again and made dialkyl glutamic surgar ester in 2 hours.
3. a kind of method for preparing dialkyl glutamic surgar ester surfactant according to claim 2, it is characterized in that: the immobilized stannic chloride catalyst of described active carbon is reusable.
4. a kind of method for preparing dialkyl glutamic surgar ester surfactant according to claim 2 is characterized in that: described glutamic acid is synthesis material.
5. the application of the described dialkyl glutamic surgar ester surfactant of claim 1 in the modification of enzyme.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2005100192553A CN100391585C (en) | 2005-08-08 | 2005-08-08 | Dialkyl glutamic surgar ester surfactant, prepn. method and use thereof |
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| CNB2005100192553A CN100391585C (en) | 2005-08-08 | 2005-08-08 | Dialkyl glutamic surgar ester surfactant, prepn. method and use thereof |
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| CN1718276A CN1718276A (en) | 2006-01-11 |
| CN100391585C true CN100391585C (en) | 2008-06-04 |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6096701A (en) * | 1999-06-29 | 2000-08-01 | Colgate Palmolive Company | Antimicrobial multi purpose containing a cationic surfactant |
| CN1410160A (en) * | 2002-11-26 | 2003-04-16 | 南京师范大学 | Carrier loading platinum metal and preparation method of platinum based multielement metal catalyst organic collosol |
| CN1146571C (en) * | 1996-07-19 | 2004-04-21 | 普罗克特和甘保尔公司 | Methods for producing polyol fatty acid polyesters using atmospheric or superatmospheric pressure |
| US20040209795A1 (en) * | 2003-04-21 | 2004-10-21 | Vlad Florin Joseph | VOC-free microemulsions |
| CN1554747A (en) * | 2003-12-26 | 2004-12-15 | 南开大学 | Engineering strain for moducing lipopeptide and its construction method |
| CN1583990A (en) * | 2004-06-01 | 2005-02-23 | 武汉大学 | Chitin betaine surfactant composition and its preparation and agent |
| CN1203071C (en) * | 2000-03-17 | 2005-05-25 | 欧兰德制药有限公司 | Polysaccharidic esters of N-derivatives of glutamic acid |
-
2005
- 2005-08-08 CN CNB2005100192553A patent/CN100391585C/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1146571C (en) * | 1996-07-19 | 2004-04-21 | 普罗克特和甘保尔公司 | Methods for producing polyol fatty acid polyesters using atmospheric or superatmospheric pressure |
| US6096701A (en) * | 1999-06-29 | 2000-08-01 | Colgate Palmolive Company | Antimicrobial multi purpose containing a cationic surfactant |
| CN1203071C (en) * | 2000-03-17 | 2005-05-25 | 欧兰德制药有限公司 | Polysaccharidic esters of N-derivatives of glutamic acid |
| CN1410160A (en) * | 2002-11-26 | 2003-04-16 | 南京师范大学 | Carrier loading platinum metal and preparation method of platinum based multielement metal catalyst organic collosol |
| US20040209795A1 (en) * | 2003-04-21 | 2004-10-21 | Vlad Florin Joseph | VOC-free microemulsions |
| CN1554747A (en) * | 2003-12-26 | 2004-12-15 | 南开大学 | Engineering strain for moducing lipopeptide and its construction method |
| CN1583990A (en) * | 2004-06-01 | 2005-02-23 | 武汉大学 | Chitin betaine surfactant composition and its preparation and agent |
Non-Patent Citations (2)
| Title |
|---|
| Synthesis and Emulsion Properties of a Novel NonionicSurfactant, Dialkyl Glucosylglutamate. Wakako Tsuzuki et al.Journal of Agricultural and Food Chemistry,Vol.41 No.12. 1993 |
| Synthesis and Emulsion Properties of a Novel NonionicSurfactant, Dialkyl Glucosylglutamate. Wakako Tsuzuki et al.Journal of Agricultural and Food Chemistry,Vol.41 No.12. 1993 * |
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