CN103130675A - Industrial production method of high-purity N-lauroyl-L-alanine surfactant - Google Patents
Industrial production method of high-purity N-lauroyl-L-alanine surfactant Download PDFInfo
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- CN103130675A CN103130675A CN201110375229XA CN201110375229A CN103130675A CN 103130675 A CN103130675 A CN 103130675A CN 201110375229X A CN201110375229X A CN 201110375229XA CN 201110375229 A CN201110375229 A CN 201110375229A CN 103130675 A CN103130675 A CN 103130675A
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Abstract
The invention discloses an industrial production method of a high-purity N-lauroyl-L-alanine surfactant, which comprises the following steps: A, dissolving a certain amount of alanine and a metal inorganic base in a certain amount of mixed solvents of distilled water and organic solvents to prepare an alanine salt; B, slowly and dropwisely adding metered lauroyl chloride into the reaction solution at a certain temperature, dropwisely adding the metal inorganic base solution with a certain concentration to maintain the pH value of the reaction system to be a specified value, after the dropwise addition, continuing to stirring for a specified time to generate an N-lauroyl-L-alanine salt; C, after the reaction is stopped, acidifying the product with dilute hydrochloric acid to obtain a pH of 3-4, precipitating solids, performing suction filtration, stirring and washing the obtained solid with water twice, performing recrystallization of the crude product with a solvent, performing heating reflux, cooling, filtration, and drying to obtain white powdery N-lauroyl-L-alanine with high purity of more than 98%. The method of the invention is simple, practical, low in cost, high in production efficiency, and suitable for industrial production.
Description
Technical field
The present invention relates to the production method of a kind of highly purified N-lauroyl-ALANINE tensio-active agent, particularly a kind of simple and practical, cost is low, produce the industrialized preparing process of the high highly purified N-lauroyl of yield-ALANINE tensio-active agent, belong to amino acid type surfactant preparation of industrialization technical field.
Background technology
Tensio-active agent refers to that those have very strong tensio-active agent, can make the remarkable material that descends of surface tension of liquid.Tensio-active agent scope very extensive (positively charged ion, negatively charged ion, nonionic and both sexes), for concrete the application provides several functions, comprise wetting or anti-stick, emulsification or breakdown of emulsion, foaming or froth breaking and solubilising, disperse, washing, anticorrosion, antistatic etc., that a class is versatile and flexible, broad-spectrum fine chemical product.
Common tensio-active agent, although be widely used in production, life because having good characteristic, its biological degradability and eco-compatibility are poor, can work the mischief to ecotope.Along with people more and more pay close attention to the security, mildness of various product and to the raising of environmental protection requirement, study and develop the main direction that multi-functional high-quality good environment friendly surface promoting agent has become Surfactant Industry.
N-lauroyl-ALANINE tensio-active agent has good wettability, whipability, germ resistance and against corrosion, antistatic effect, almost non-toxic harmless, gentle to skin, therefore its degraded product be amino acid and lipid acid on almost not impact of environment, but also have advantages of with the consistency of other tensio-active agents good.Can be widely used in makeup, as cleansing milk, body wash, shampoo, facial mask etc., washing composition, food, beverage, health care, mineral floating, oil fuel, metal surface cleaning, textile printing and dyeing, agricultural chemicals allotment etc.
Synthetic preparation about N-lauroyl-ALANINE, adopt Xiao Dun-Bao Man (Schotten-Banmann) condensation reaction to prepare industrial at present, be about to lauroyl chloride and ALANINE and make N-lauroyl-ALANINE salt in alkaline aqueous solution or other organic solvent, then in mineral acid with separate to get N-lauroyl-ALANINE crude product.Products obtained therefrom purity is not high, and impurity is also a lot, and is very large to the quality influence of product, needs special methods, and as pure in post analysing just can be purified to purity more than 98%, and troublesome poeration, cost are also high, are difficult to realize industrialized production.
Summary of the invention
The present invention seeks to have proposed in order to overcome the deficiencies in the prior art a kind of simple and practical, cost is low, produces the industrialized preparing process of the high highly purified N-lauroyl of yield-ALANINE tensio-active agent.
For achieving the above object, the technical solution used in the present invention is: the industrialized preparing process of a kind of highly purified N-lauroyl-ALANINE tensio-active agent comprises the following steps:
A, a certain amount of L-Ala and metal inorganic alkali are dissolved in the mixed solvent of a certain amount of distilled water and organic solvent and make L-Ala salt;
B, slowly drip at a certain temperature the lauroyl chloride of metering in the above-mentioned reaction solution, dripping certain density metal inorganic alkaline solution, to keep the pH value of reaction system be prescribed value again, after dropwising, continue to be stirred to the specified time, generate N-lauroyl-ALANINE salt;
After C, stopped reaction, be acidified to PH=3-4 with dilute hydrochloric acid, gradually have solid to separate out, suction filtration, the gained solid washed twice of blunging, with crude product solubilizing agent recrystallization, reflux, cooling, filter, dry, namely get the N-lauroyl-ALANINE of the white powder of high purity more than 98%.
Preferably, described metal inorganic alkali is selected from sodium hydroxide, sodium carbonate, potassium hydroxide, in salt of wormwood one.
Preferably, the molar ratio of described ALANINE and metal inorganic alkali is 1: 1.
Preferably, described organic solvent is selected from the acetone in hydrophilic organic solvent, methyl alcohol, ethanol, acetonitrile, in tetrahydrofuran (THF) one.
Preferably, in described mixed solvent, the volume ratio of water and organic solvent is 0.5-2: 1.
Preferably, described lauroyl chloride and amino acid whose molar ratio are controlled at 1: 1-2.5.
Preferably, described temperature of reaction is chosen 10-30 ℃.
Preferably, described reaction system PH is to being controlled at 8-10.
Preferably, the described reaction times is selected from 1-6 hour.
Preferably, described recrystallization solvent used can be acetone, methyl alcohol, ethanol, acetonitrile, tetrahydrofuran (THF) or above-mentioned solvent and the made mixed solvent of water.
Preferably, described solvent comprises acetone, ethanol and water, and volume ratio is 0.25: 0.25: 1.
Due to the utilization of technique scheme, the present invention compared with prior art has following advantages:
It is Powdered that N-lauroyl-ALANINE that the industrialized preparing process of highly purified N-lauroyl of the present invention-ALANINE tensio-active agent makes is crystalline solid, appearance luster is good and content is high, content reaches more than 98%, excellent product performance, and in cosmetics of everyday use is used, can not produce influence of fluctuations to the pH value of goods, approaching with the mean P H value of skin, effectively improved quality product, to skin and hair action temperature and; And the inventive method is simple and practical, and cost is low, and production efficiency is high, is fit to suitability for industrialized production.
Description of drawings
Below in conjunction with accompanying drawing, technical solution of the present invention is described further:
Accompanying drawing 1 is the chemical equation of the industrialized preparing process of highly purified N-lauroyl of the present invention-ALANINE tensio-active agent;
Wherein, 1. with 2. be connected in figure; M is potassium or sodium.
Embodiment
Embodiment 1:
under normal temperature, in the 1000ml four-hole boiling flask, 89g (1mol) ALANINE is dissolved in 200mL water, adds 40g (1mol) NaOH, then add 200mL acetone to stir, temperature is controlled at 24-26 ℃, slowly at the uniform velocity drip 198.6g (0.9mol) lauroyl chloride, approximately dripped off in 1 hour, splash into again 50% aqueous sodium hydroxide solution approximately about 72mL, carefully control the pH value of reaction solution in 9 left and right, after dripping end, in 24-26 ℃ continue to keep again PH react between 9 left and right 2 hours constant to PH, get white pasty state reactant, stopped reaction, with the hcl acidifying of 0.6mol/L to PH3-4, gradually there is solid to separate out, placed 2 hours under ice bath, filter, the gained solid washed twice of blunging, dry to get N-lauroyl-ALANINE crude product 234g.
Get crude product 100g, be dissolved in the 400mL mixed solvent, described mixed solvent is comprised of 100mL acetone, 100mL ethanol, 200ml water; Heated and stirred extremely refluxes, after crude product all dissolves in mixed solvent, and slow cooling, gradually the adularescent solid generates, stir after 60 minutes under ice bath, have a large amount of white solids to separate out, filter 60 ℃ of oven dry, get white N-lauroyl-ALANINE crystallization 94.5g, total recovery 86.2%, content 99.2%.Chemical equation is seen accompanying drawing 1.
Embodiment 2:
Under normal temperature, in the 1000mL four-hole boiling flask, 89g (1mol) ALANINE is dissolved in 200mL water, adds 56g (1mol) KOH, then add 200mL acetone to stir; Temperature is controlled at 24-26 ℃, slowly at the uniform velocity drip 198.6g (0.9mol) lauroyl chloride, approximately dripped off in 1 hour, splash into again approximately 100mL of the 50%KOH aqueous solution, carefully control the pH value of reaction solution in 9 left and right, after dripping end, in 24-26 ℃ continue to keep again PH react between 9 left and right 2 hours constant to PH, get white pasty state reactant, stopped reaction, with the hcl acidifying of 0.6mol/L to PH 3-4, gradually there is solid to separate out, placed 2 hours under ice bath, filter, the gained solid washed twice of blunging is dried to get N-lauroyl-ALANINE crude product 231.1g.
Get crude product 100g, be dissolved in the 400mL mixed solvent, described mixed solvent is comprised of 100mL acetone, 100mL ethanol, 200mL water, heated and stirred is to refluxing, after crude product all dissolves in mixed solvent, slow cooling, gradually the adularescent solid generates, stir after 60 minutes under ice bath, there are a large amount of white solids to separate out, filter 60 ℃ of oven dry, get white N-lauroyl-ALANINE crystallization 94.3g, content 99.1%.Chemical equation is seen accompanying drawing 1.
Embodiment 3:
Under normal temperature, in the 1000mL four-hole boiling flask, 89g (1mol) ALANINE is dissolved in 200mL water, adds 53g (0.5mol) Na2CO3, then add 200mL acetone to stir; Temperature is controlled at 24-26 ℃, slowly at the uniform velocity drip 198.6g (0.9mol) lauroyl chloride, approximately dripped off in 1 hour, splash into again approximately 95mL of 50% aqueous sodium carbonate, carefully control the pH value of reaction solution in 9 left and right, after dripping end, in 24-26 ℃ continue to keep again PH react between 9 left and right 2 hours constant to PH, get white pasty state reactant, stopped reaction, with the hcl acidifying of 0.6mol/L to PH3-4, gradually there is solid to separate out, placed 2 hours under ice bath, filter, the gained solid washed twice of blunging is dried to get N-lauroyl-ALANINE crude product 226g.
Get crude product 100g, be dissolved in the 400mL mixed solvent, described mixed solvent is comprised of 100mL acetone, 100mL ethanol, 200mL water, heated and stirred extremely refluxes, after crude product all dissolves in mixed solvent, and slow cooling, gradually the adularescent solid generates, stir after 60 minutes under ice bath, have a large amount of white solids to separate out, filter, 60 ℃ of oven dry, get white N-lauroyl-ALANINE crystallization 93.1g, total recovery 81.8%, content 99.3%.Chemical equation is seen accompanying drawing 1.
Embodiment 4:
Under normal temperature, in the 1000mL four-hole boiling flask, 89g (1mol) ALANINE is dissolved in 200mL water, adds 69g (0.5mol) K2CO3, then add 200mL acetone to stir; Temperature is controlled at 24-26 ℃, slowly at the uniform velocity drip 198.6g (0.9mol) lauroyl chloride, approximately dripped off in 1 hour, splash into again approximately 120mL of 50% wet chemical, carefully control the pH value of reaction solution in 9 left and right, after dripping end, in 24-26 ℃ continue to keep again PH react between 9 left and right 2 hours constant to PH, get white pasty state reactant, stopped reaction, with the hcl acidifying of 0.6mol/L to PH3-4, gradually there is solid to separate out, placed 2 hours under ice bath, filter, the gained solid washed twice of blunging is dried to get N-lauroyl-ALANINE crude product 228g.
Get crude product 100g, be dissolved in the 400mL mixed solvent, described mixed solvent is comprised of 100mL acetone, 100mL ethanol, 200mL water, heated and stirred extremely refluxes, after crude product all dissolves in mixed solvent, and slow cooling, gradually the adularescent solid generates, stir after 60 minutes under ice bath, have a large amount of white solids to separate out, filter, 60 ℃ of oven dry, get white N-lauroyl-ALANINE crystallization 93.5g, total recovery 80.7%, content 99.3%.Chemical equation is seen accompanying drawing 1.
Embodiment 5
under normal temperature, in the 1000mL four-hole boiling flask, 89g (1mol) ALANINE is dissolved in 200mL water, adds 40g (1mol) NaOH, then add 200mL acetone to stir, temperature is controlled at 24-26 ℃, slowly at the uniform velocity drip 198.6g (0.9mol) lauroyl chloride, splash into simultaneously 50% aqueous sodium hydroxide solution approximately about 72mL, carefully control the pH value of reaction solution in 9 left and right, approximately dripped off in 1 hour, after dripping end, in 24-26 ℃ continue to keep again PH react between 9 left and right 2 hours constant to PH, get white pasty state reactant, stopped reaction, with the hcl acidifying of 0.6mol/L to PH3-4, gradually there is solid to separate out, placed 2 hours under ice bath, filter, the gained solid is with twice of 50 ℃ of warm water agitator treating, dry to get N-lauroyl-ALANINE crude product 220.5g.
Get crude product 100g, be dissolved in the 400mL mixed solvent, described mixed solvent is comprised of 100mL acetone, 100mL ethanol, 200mL water, heated and stirred extremely refluxes, after crude product all dissolves in mixed solvent, and slow cooling, gradually the adularescent solid generates, stir after 60 minutes under ice bath, have a large amount of white solids to separate out, filter, 60 ℃ of oven dry, get white N-lauroyl-ALANINE crystallization 93.2g, total recovery 79.9%, content 99.0%.Chemical equation is seen accompanying drawing 1.
Due to the utilization of technique scheme, the present invention compared with prior art has following advantages:
It is Powdered that N-lauroyl-ALANINE that the industrialized preparing process of highly purified N-lauroyl of the present invention-ALANINE tensio-active agent makes is crystalline solid, appearance luster is good and content is high, content reaches more than 98%, excellent product performance, and in cosmetics of everyday use is used, can not produce influence of fluctuations to the pH value of goods, approaching with the mean P H value of skin, effectively improved quality product, to skin and hair action temperature and; And the inventive method is simple and practical, and cost is low, and production efficiency is high, is fit to suitability for industrialized production.
Above-described embodiment only is explanation technical conceive of the present invention and characteristics; its purpose is to allow person skilled in the art scholar can understand content of the present invention and be implemented; can not limit protection scope of the present invention with this; all equivalences that spirit is done according to the present invention change or modify, and all should be encompassed in protection scope of the present invention.
Claims (10)
1. the industrialized preparing process of highly purified N-lauroyl-ALANINE tensio-active agent comprises the following steps:
A, a certain amount of L-Ala and metal inorganic alkali are dissolved in the mixed solvent of a certain amount of distilled water and organic solvent and make L-Ala salt;
B, slowly drip at a certain temperature the lauroyl chloride of metering in the above-mentioned reaction solution, dripping certain density metal inorganic alkaline solution, to keep the pH value of reaction system be prescribed value again, after dropwising, continue to be stirred to the specified time, generate N-lauroyl-ALANINE salt;
After C, stopped reaction, be acidified to PH=3-4 with dilute hydrochloric acid, gradually have solid to separate out, suction filtration, the gained solid washed twice of blunging, with crude product solubilizing agent recrystallization, reflux, cooling, filter, dry, namely get the N-lauroyl-ALANINE of the white powder of high purity more than 98%.
2. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: described metal inorganic alkali is selected from sodium hydroxide, sodium carbonate, potassium hydroxide, in salt of wormwood one.
3. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: the molar ratio of described ALANINE and metal inorganic alkali is 1: 1.
4. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: described organic solvent is selected from the acetone in hydrophilic organic solvent, methyl alcohol, ethanol, acetonitrile, in tetrahydrofuran (THF) one.
5. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: in described mixed solvent, the volume ratio of water and organic solvent is 0.5-2: 1.
6. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: described lauroyl chloride and amino acid whose molar ratio are controlled at 1: 1-2.5.
7. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: described temperature of reaction is chosen 10-30 ℃.
8. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: described reaction system PH is to being controlled at 8-10.
9. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent, it is characterized in that: the described reaction times is selected from 1-6 hour.
10. the industrialized preparing process of highly purified N-lauroyl according to claim 1-ALANINE tensio-active agent is characterized in that: described recrystallization solvent used can be acetone, methyl alcohol, ethanol, acetonitrile, tetrahydrofuran (THF) or above-mentioned solvent and the made mixed solvent of water.
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| CN103894105A (en) * | 2014-03-24 | 2014-07-02 | 广东肇庆星湖生物科技股份有限公司 | N-long-chain acyl hydroxy amino acid surfactant and preparation method |
| CN103951581A (en) * | 2014-04-05 | 2014-07-30 | 烟台恒迪克能源科技有限公司 | Synthesis of n-undecane diacyl diaspartic acid-bis-diglycolamine salt |
| CN104649927A (en) * | 2013-11-25 | 2015-05-27 | 刘现梅 | N-undecane diacyl diglutamic acid triethanolamine salt and preparation method thereof |
| CN105001111A (en) * | 2015-06-30 | 2015-10-28 | 广州天赐高新材料股份有限公司 | Preparation method of N-lauroyl-L-alanine saline solution with low inorganic salt content |
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| CN108752228A (en) * | 2018-06-04 | 2018-11-06 | 苏州欧丽特生物医药有限公司 | A kind of preparation method and application of N- lauroyl-l-Alanine |
| WO2019233375A1 (en) * | 2018-06-04 | 2019-12-12 | 苏州欧丽特生物医药有限公司 | Self-assembled amino acid supramolecular polymer, preparation therefor, and application thereof |
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| CN112479916A (en) * | 2020-12-02 | 2021-03-12 | 湖南丽臣奥威实业有限公司 | Method for producing N-lauroyl glycine or salt thereof |
| CN114713152A (en) * | 2022-04-01 | 2022-07-08 | 岳阳科罗德联合化学工业有限公司 | Production system and preparation method for producing salt-free amino acid surfactant by continuous flow |
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| CN104649927A (en) * | 2013-11-25 | 2015-05-27 | 刘现梅 | N-undecane diacyl diglutamic acid triethanolamine salt and preparation method thereof |
| CN104649927B (en) * | 2013-11-25 | 2017-10-31 | 江苏四新界面剂科技有限公司 | A kind of glutamic acid triethanolamine salt of n-undecane diacyl two and preparation method thereof |
| CN103894105A (en) * | 2014-03-24 | 2014-07-02 | 广东肇庆星湖生物科技股份有限公司 | N-long-chain acyl hydroxy amino acid surfactant and preparation method |
| CN103951581A (en) * | 2014-04-05 | 2014-07-30 | 烟台恒迪克能源科技有限公司 | Synthesis of n-undecane diacyl diaspartic acid-bis-diglycolamine salt |
| CN103951581B (en) * | 2014-04-05 | 2016-04-27 | 烟台恒迪克能源科技有限公司 | A kind of synthesis of positive 11 carbon diacyl two aspartic acids-bis--glycol ether amine salt |
| CN105001111A (en) * | 2015-06-30 | 2015-10-28 | 广州天赐高新材料股份有限公司 | Preparation method of N-lauroyl-L-alanine saline solution with low inorganic salt content |
| WO2019233375A1 (en) * | 2018-06-04 | 2019-12-12 | 苏州欧丽特生物医药有限公司 | Self-assembled amino acid supramolecular polymer, preparation therefor, and application thereof |
| CN108752228A (en) * | 2018-06-04 | 2018-11-06 | 苏州欧丽特生物医药有限公司 | A kind of preparation method and application of N- lauroyl-l-Alanine |
| CN108752420A (en) * | 2018-06-04 | 2018-11-06 | 苏州欧丽特生物医药有限公司 | A kind of compound and its preparation method and application |
| WO2019233377A1 (en) * | 2018-06-04 | 2019-12-12 | 苏州欧丽特生物医药有限公司 | Novel self-assembled amino acid supramolecular polymer, preparation method therefor, and application thereof |
| CN108752420B (en) * | 2018-06-04 | 2022-09-13 | 苏州欧丽特生物医药有限公司 | Compound and preparation method and application thereof |
| CN108752228B (en) * | 2018-06-04 | 2022-09-30 | 苏州欧丽特生物医药有限公司 | Preparation method and application of N-lauroyl-L-alanine |
| US11540993B2 (en) | 2018-06-04 | 2023-01-03 | Suzhou Oulit Biopharm Co., Ltd | Self-assembled amino acid supramolecular polymer, preparation method therefor, and application thereof |
| AU2019280295B2 (en) * | 2018-06-04 | 2023-01-19 | Suzhou Oulit Biopharm Co., Ltd | Self-assembled amino acid supramolecular polymer, preparation therefor, and application thereof |
| US11566110B2 (en) | 2018-06-04 | 2023-01-31 | Suzhou Oulit Biopharm Co., Ltd | Self-assembled amino acid supramolecular polymer, preparation therefor, and application thereof |
| CN112479916A (en) * | 2020-12-02 | 2021-03-12 | 湖南丽臣奥威实业有限公司 | Method for producing N-lauroyl glycine or salt thereof |
| CN112479916B (en) * | 2020-12-02 | 2022-09-02 | 湖南丽臣奥威实业有限公司 | Method for producing N-lauroyl glycine or salt thereof |
| CN114713152A (en) * | 2022-04-01 | 2022-07-08 | 岳阳科罗德联合化学工业有限公司 | Production system and preparation method for producing salt-free amino acid surfactant by continuous flow |
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Application publication date: 20130605 |