CN114933545A - Method for synthesizing lauroyl lysine - Google Patents
Method for synthesizing lauroyl lysine Download PDFInfo
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- CN114933545A CN114933545A CN202210203415.3A CN202210203415A CN114933545A CN 114933545 A CN114933545 A CN 114933545A CN 202210203415 A CN202210203415 A CN 202210203415A CN 114933545 A CN114933545 A CN 114933545A
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- Prior art keywords
- lauroyl lysine
- water
- lysine
- alkali
- alcohol
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention provides a method for synthesizing lauroyl lysine, which is characterized by comprising the following steps: under the condition of alkali, L-lysine hydrochloride and lauric acid are used as raw materials, isopropanol is used as an accelerating agent, and a target product is obtained after reaction, water separation and post-treatment. The invention adopts new experimental conditions, improves the yield, obtains products with higher content and solves the problem of large sewage production quantity at present. The solvent is recycled and reused, the production cost is reduced, and the method is more suitable for industrial production.
Description
Technical Field
The invention relates to the technical field of lubricant preparation, in particular to a novel process and a novel method for preparing lauroyl lysine.
Background
Lauroyl lysine is an amino acid derivative, and its raw material is derived from natural product, and has good biodegradability and high safety. As a novel lubricant, lauroyl lysine has the characteristics of high lubricity, smooth skin feel, low friction coefficient, antistatic property, oxidation resistance, insolubility in water, most organic solvents and the like, is widely used in products such as hair and skin conditioners, foundation emulsion, blush liquid, high-end facial cleansing products and the like, can be added into the products to help the solvents to be gelatinized and improve the texture of the products, and can also be used for surface treatment of mica powder and TiO 2.
However, at present, the lauroyl lysine is mainly produced by a chemical synthesis method and an enzyme-catalyzed synthesis method, and the traditional chemical method uses a large amount of water and has large sewage quantity, so that the method is not suitable for industrial production. The enzymatic synthesis method is difficult to industrialize because lysine acylase is expensive and not easily available.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of lauroyl lysine, and solving the problem of large wastewater amount and large production in the prior art.
In order to realize the purpose, the invention adopts the technical scheme that:
the invention provides a method for synthesizing lauroyl lysine, which is characterized by comprising the following steps:
under the condition of alkali, L-lysine hydrochloride and lauric acid are used as raw materials, isopropanol is used as an accelerating agent, and a target product is obtained after reaction, water separation and post-treatment.
The above process can be expressed by the following general formula:
the invention provides a method for synthesizing lauroyl lysine, which is further characterized by comprising the following steps: the molar ratio of the L-lysine hydrochloride to the lauric acid is 1: 0.8-1.3.
The invention provides a method for synthesizing lauroyl lysine, which is further characterized by comprising the following steps: the molar ratio of the alkali to the L-lysine hydrochloride is 1: 0.8-1.2.
The invention provides a method for synthesizing lauroyl lysine, which is further characterized by comprising the following steps: the molar ratio of the isopropanol to the L-lysine hydrochloride is 1: 1.2-1.8.
The method for synthesizing the lauroyl lysine is also characterized by comprising the following steps: the alkali is selected from one or more of alkali metal hydroxide salts.
The invention provides a method for synthesizing lauroyl lysine, which is further characterized by comprising the following specific process steps:
s1, stirring water and alkali to dissolve clear solution for 15-60 min;
s2, adding L-lysine hydrochloride and lauric acid;
s3, adding isopropanol, heating to 55-65 ℃, and stirring for 1-2.5 hours;
s4, carrying out reduced pressure water distillation until the water is dried;
s5, adding chlorobenzene for reflux water diversion;
in the research of the invention, the specific heat capacity of water is large, the water is difficult to vaporize, the water can form azeotropy with the water after the chlorobenzene is added, the situation of local temperature overheating cannot occur in the process of carrying away the water, the reaction speed can be accelerated when the water carrying speed is high, meanwhile, the chlorobenzene has good solubility to materials, the reaction is quicker, and the flash point is high and safe.
S6, after decompression and concentration, cooling to below 20 ℃, adding alcohol and alkali, and stirring for 1-3 hours;
s7, adjusting the pH value of the system to be neutral, and filtering to obtain a wet product.
The invention provides a method for synthesizing lauroyl lysine, which is further characterized by comprising the following steps: the reagent for adjusting pH in S7 is an inorganic acid.
In the research of the invention, the inorganic acid such as hydrochloric acid is used for carrying out the pH adjustment process, the cost is lower, the acidity is better than that of hydrochloric acid than that of organic acid such as acetic acid, the reaction speed is higher, and the result that the target effect can be achieved without heating reflux can be realized.
The invention provides a method for synthesizing lauroyl lysine, which is further characterized by comprising the following steps: the refining process of the wet product comprises the following steps:
s7-1, adding the wet product into a mixed solution of alcohol and alkali, stirring for 1-3 hours, adjusting the pH value to be neutral, and filtering again to obtain a wet product;
s7-2, adding the wet product obtained in the step S7-1 into a mixed solution of methanol and water, stirring for 1-3 hours, and filtering and drying to obtain a target product.
The invention provides a method for synthesizing lauroyl lysine, which is further characterized by comprising the following steps:
in step S7, the ratio of alcohol to base is 8-10g base per 1L alcohol;
in step S7-1, the ratio of alcohol to base is 12.5-15g base per 1L alcohol.
The method for synthesizing the lauroyl lysine is also characterized by comprising the following steps:
in S7-2, the volume ratio of alcohol to water is 2: 1-2.
The beneficial effects created by the invention are as follows:
the invention adopts new experimental conditions, improves the yield, obtains products with higher content and solves the problem of large sewage production quantity at present. The solvent is recycled and reused, the production cost is reduced, and the method is more suitable for industrial production.
The research of the invention finds that the L-lysine hydrochloride is cheap and easy to obtain when being used as the raw material.
The isopropanol is adopted to effectively promote the dissolution of materials, increase the reaction temperature and accelerate the reaction process, and is superior to other traditional solvents.
Detailed Description
In order to make the technical means, the original characteristics, the achieved purposes and the effects of the invention easy to understand, the invention is further described with the specific embodiments, but the invention includes but is not limited to the embodiment.
Example 1
The first step of reaction operation process:
267.5g of water and 60g (1.5mol) of sodium hydroxide were added to a three-necked flask, and stirred for thirty minutes to dissolve, then 250g (1.37mol) of L-lysine hydrochloride and 250g of lauric acid (1.25mol) were added, and 50g of isopropyl alcohol (0.67mol) was further added, and the mixture was heated to 60 ℃ and stirred for 2 hours. The water is distilled under reduced pressure, 2L of chlorobenzene is added after the water is distilled to dryness, and the temperature is raised until reflux is carried out to divide water.
The second step of reaction operation process:
after the reaction is divided, the concentration is reduced, after the reaction is evaporated to dryness, the temperature is reduced to 20 ℃, 5.5L of methanol and 53.6g of sodium hydroxide are added, the mixture is stirred and dissolved for 2 hours, hydrochloric acid is added dropwise to adjust the pH value to 7, and a wet product is obtained by filtration;
adding the wet product into 4L of methanol and 53.6g of sodium hydroxide, stirring and dissolving for 2 hours, dropwise adding hydrochloric acid to adjust the pH value to 7, and filtering to obtain a wet product; adding the wet product into 2L of methanol and 1L of water, stirring for 1 hour, filtering to obtain a wet product, and drying to obtain 348.5g of lauroyl lysine with yield of 85% and purity of 99.5%.
Example 2
The first step of reaction operation process:
267.5g of water and 60g of sodium hydroxide were added to a three-necked flask, and stirred for thirty minutes to dissolve, and then 220g L-lysine hydrochloride and 240g of lauric acid were added, and 70g of isopropyl alcohol was further added, and the mixture was heated to 60 ℃ and stirred for 2.5 hours. And (3) evaporating water under reduced pressure, adding 2L of chlorobenzene after evaporation to dryness, and heating to reflux for water diversion.
The second step of reaction operation process:
after the reaction is divided, the concentration is reduced, after the reaction is evaporated to dryness, the temperature is reduced to 20 ℃, 5L of methanol and 53.6g of sodium hydroxide are added, the mixture is stirred and dissolved for 2 hours, hydrochloric acid is added dropwise to adjust the pH value to 7, and a wet product is obtained by filtration;
adding the wet product into 4L methanol and 50g sodium hydroxide, stirring and dissolving for 3 hours, dropwise adding hydrochloric acid to adjust the pH value to 7, and filtering to obtain a wet product; adding the wet product into 2L of methanol and 2L of water, stirring for 2 hours, filtering to obtain a wet product, and drying to obtain 348.5g of lauroyl lysine, wherein the yield is 88 percent, and the purity is 99.1 percent.
Example 3
The first step of reaction operation process:
267.5g of water and 60g of sodium hydroxide were added to a three-necked flask, and stirred for thirty minutes to dissolve, 265g L-lysine hydrochloride and 330g of lauric acid were added, 88g of isopropyl alcohol was further added, the temperature was raised to 60 ℃, and stirring was carried out for 2 hours. And (3) evaporating water under reduced pressure, adding 2L of chlorobenzene after evaporation to dryness, and heating to reflux for water diversion.
The second step of reaction operation process:
after reaction water separation is finished, concentration is reduced, after evaporation to dryness, the temperature is reduced to 20 ℃, 5.5L of methanol and 53.6g of sodium hydroxide are added, stirring and dissolving are carried out for 2 hours, hydrochloric acid is dripped to adjust the pH value to 7, and a wet product is obtained by filtration;
adding the wet product into 4L of methanol and 53.6g of sodium hydroxide, stirring and dissolving for 1 hour, dropwise adding hydrochloric acid to adjust the pH value to 7, and filtering to obtain a wet product; adding the wet product into 2L of methanol and 1.5L of water, stirring for 2 hours, filtering to obtain a wet product, and drying to obtain 348.5g of lauroyl lysine with the yield of 81% and the purity of 99.6%.
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, but that various changes and modifications may be made without departing from the spirit and scope of the invention, and such changes and modifications are within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. A method for synthesizing lauroyl lysine is characterized by comprising the following steps:
under the condition of alkali, L-lysine hydrochloride and lauric acid are used as raw materials, isopropanol is used as an accelerating agent, and a target product is obtained after reaction, water separation and post-treatment.
2. The method for synthesizing lauroyl lysine according to claim 1, wherein:
the molar ratio of the L-lysine hydrochloride to the lauric acid is 1: 0.8-1.3.
3. The method for synthesizing lauroyl lysine according to claim 1, wherein:
the molar ratio of the alkali to the L-lysine hydrochloride is 1: 0.8-1.2.
4. The method for synthesizing lauroyl lysine according to claim 1, wherein:
the molar ratio of the isopropanol to the L-lysine hydrochloride is 1: 1.2-2.1.
5. The method for synthesizing lauroyl lysine according to claim 1, wherein:
the alkali is selected from one or more of alkali metal hydroxide salts.
6. The method for synthesizing lauroyl lysine according to any one of claims 1 to 5, comprising the following specific process steps:
s1, stirring water and alkali to dissolve clear solution for 15-60 min;
s2, adding L-lysine hydrochloride and lauric acid;
s3, adding isopropanol, heating to 55-65 ℃, and stirring for 1-2.5 hours;
s4, carrying out reduced pressure water distillation until the water is dried;
s5, adding chlorobenzene for reflux water diversion;
s6, after decompression and concentration, cooling to below 20 ℃, adding alcohol and alkali, and stirring for 1-3 hours;
s7, adjusting the pH value of the system to be neutral, and filtering to obtain a wet product.
7. The method for synthesizing lauroyl lysine in accordance with claim 6, wherein:
the reagent for adjusting the pH in the S7 is an inorganic acid.
8. The method for synthesizing lauroyl lysine in accordance with claim 6, wherein:
the wet product has the following refining process:
s7-1, adding the wet product into a mixed solution of alcohol and alkali, stirring for 1-3 hours, adjusting the pH value to be neutral, and filtering again to obtain a wet product;
s7-2, adding the wet product obtained in the step S7-1 into a mixed solution of methanol and water, stirring for 1-3 hours, and filtering and drying to obtain a target product.
9. The method for synthesizing lauroyl lysine in accordance with claim 6, wherein:
in step S7, the ratio of alcohol to base is 8-10g base per 1L alcohol;
in step S7-1, the alcohol and the base are added in a ratio of 12.5 to 15g of the base to 1L of the alcohol.
10. The method for synthesizing lauroyl lysine according to claim 6, wherein:
in S7-2, the volume ratio of alcohol to water is 2: 1-2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210203415.3A CN114933545A (en) | 2022-03-02 | 2022-03-02 | Method for synthesizing lauroyl lysine |
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| CN202210203415.3A CN114933545A (en) | 2022-03-02 | 2022-03-02 | Method for synthesizing lauroyl lysine |
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| CN114933545A true CN114933545A (en) | 2022-08-23 |
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| CN202210203415.3A Pending CN114933545A (en) | 2022-03-02 | 2022-03-02 | Method for synthesizing lauroyl lysine |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3897466A (en) * | 1972-04-25 | 1975-07-29 | Ajinomoto Kk | Method of preparing N{302 -acyl basic amino acids |
| CN107417561A (en) * | 2017-05-15 | 2017-12-01 | 山东科信生物化学有限公司 | A kind of preparation method of N lauroyl L lysines |
| CN107488130A (en) * | 2017-08-22 | 2017-12-19 | 上海鲍林化工有限公司 | A kind of preparation method of lauroyl lysine |
-
2022
- 2022-03-02 CN CN202210203415.3A patent/CN114933545A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3897466A (en) * | 1972-04-25 | 1975-07-29 | Ajinomoto Kk | Method of preparing N{302 -acyl basic amino acids |
| CN107417561A (en) * | 2017-05-15 | 2017-12-01 | 山东科信生物化学有限公司 | A kind of preparation method of N lauroyl L lysines |
| CN107488130A (en) * | 2017-08-22 | 2017-12-19 | 上海鲍林化工有限公司 | A kind of preparation method of lauroyl lysine |
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