[go: up one dir, main page]

CN118388363A - High-purity lauroyl lysine and preparation method thereof - Google Patents

High-purity lauroyl lysine and preparation method thereof Download PDF

Info

Publication number
CN118388363A
CN118388363A CN202410500766.XA CN202410500766A CN118388363A CN 118388363 A CN118388363 A CN 118388363A CN 202410500766 A CN202410500766 A CN 202410500766A CN 118388363 A CN118388363 A CN 118388363A
Authority
CN
China
Prior art keywords
acid
lysine
hydroxide
solution
lauroyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202410500766.XA
Other languages
Chinese (zh)
Inventor
毛顺聪
李洋
黄成英
李忠军
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Guangzhou Longjiu Biotechnology Co ltd
Original Assignee
Guangzhou Longjiu Biotechnology Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Guangzhou Longjiu Biotechnology Co ltd filed Critical Guangzhou Longjiu Biotechnology Co ltd
Priority to CN202410500766.XA priority Critical patent/CN118388363A/en
Publication of CN118388363A publication Critical patent/CN118388363A/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The application provides high-purity lauroyl lysine and a preparation method thereof. The preparation method of the high-purity lauroyl lysine comprises the following steps: dissolving lauric acid in ethanol, adding aqueous solution of inorganic base or organic base, removing the solution by a rotary evaporator after reaction, and vacuum drying to obtain laurate; dissolving L-lysine in water, adding an aqueous solution of an inorganic acid or an organic acid, removing the solution by a rotary evaporator after the reaction, and drying in vacuum to obtain L-lysine salt; dissolving laurate and L-lysine salt in glycol, carrying out reflux reaction, removing the solution by using a rotary evaporator, and vacuum drying to obtain lauroyl L-lysine crude product; dissolving the lauroyl L-lysine crude product in inorganic acid or organic acid solution, neutralizing with inorganic alkali or organic alkali solution, collecting precipitated crystals, washing with water, and vacuum drying to obtain high-purity lauroyl L-lysine.

Description

High-purity lauroyl lysine and preparation method thereof
Technical Field
The application relates to the technical field of chemical industry, in particular to high-purity lauroyl lysine and a preparation method thereof.
Background
Various methods for producing lauroyl lysine have been reported, and the common problems are: 1, the yield is low; 2, the purity is low. The existing preparation method is difficult to provide an industrial production preparation process and is also difficult to obtain a high-quality applicable product.
Disclosure of Invention
The embodiment of the application provides high-purity lauroyl lysine and a preparation method thereof, which are used for solving the problems of the related technology, and the technical scheme is as follows:
In a first aspect, an embodiment of the present application provides a method for preparing high-purity lauroyl lysine, including:
Dissolving lauric acid in ethanol, adding aqueous solution of inorganic base or organic base, removing the solution by a rotary evaporator after reaction, and vacuum drying to obtain laurate;
Dissolving L-lysine in water, adding an aqueous solution of an inorganic acid or an organic acid, removing the solution by a rotary evaporator after the reaction, and drying in vacuum to obtain L-lysine salt;
Dissolving laurate and L-lysine salt in glycol, carrying out reflux reaction, removing the solution by using a rotary evaporator, and vacuum drying to obtain lauroyl L-lysine crude product;
dissolving the lauroyl L-lysine crude product in inorganic acid or organic acid solution, neutralizing with inorganic alkali or organic alkali solution, collecting precipitated crystals, washing with water, and vacuum drying to obtain high-purity lauroyl L-lysine.
In one embodiment, 0.35 mol of lauric acid is dissolved in 200m l ethanol and an aqueous solution of an inorganic or organic base is added, wherein water is 150m l, 0.35 mol of inorganic or organic base; the reaction was carried out at 25-60℃for 1-4 hours, the solution was removed at 50-90℃by a rotary evaporator, and vacuum-dried at 100℃for 12 hours to obtain laurate.
In one embodiment, 0.35 mol of L-lysine is dissolved in 200m L water and an aqueous solution of an inorganic or organic acid is added, wherein water 200m L, 1.40 mol of inorganic or organic acid; the reaction is carried out at 30-80℃for 3-7 hours, the solution is removed at 80-110℃by a rotary evaporator, and the solution is dried at 100℃for 12 hours under vacuum to obtain the L-lysine salt.
In one embodiment, 0.25mol of laurate and 0.25mol of L-lysine salt are dissolved in 5000m L ethylene glycol, reflux reaction is performed at 100 to 200℃for 5 to 15 hours, the solution is removed at 80 to 110℃by a rotary evaporator, and vacuum drying is performed at 120℃for 12 hours to obtain crude lauroyl L-lysine.
In one embodiment, 0.25 mol of lauroyl L-lysine crude product is dissolved in an inorganic acid or organic acid solution, and the solution is neutralized to pH2-5 with an inorganic base or organic base solution, and precipitated crystals are collected, washed with water to pH7, and vacuum-dried at 100 ℃ for 12 hours to obtain high-purity lauroyl L-lysine.
In one embodiment, the inorganic base comprises one or more of sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, lithium hydroxide, magnesium hydroxide, zinc hydroxide, copper hydroxide, iron hydroxide, lead hydroxide, cobalt hydroxide, chromium hydroxide, zirconium hydroxide, nickel hydroxide, ammonium hydroxide, anhydrous sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate.
In one embodiment, the organic base comprises one or more of methylamine, ethylamine, dimethylamine, diethylamine, pyridine, quinoline, 1- (3-methyl-benzofuranyl) ethanone, acetone, butanone, pentanone, hexanone, heptanone, octanone, arbitrary ketone, sodium methoxide, potassium ethoxide, potassium tert-butoxide, an alkyllithium reagent, a grignard reagent, a quaternary ammonium hydroxide, butyllithium, phenyllithium, lithium diisopropylamide, lithium hexamethyldisilazide, a quaternary ammonium base, a quaternary phosphonium base, sulfonium ions, guanidine compounds, sodium methoxide, potassium ethoxide, potassium tert-butoxide.
In one embodiment, the inorganic acid comprises one or more of hydrobromic acid, hypobromous acid, hydroiodic acid, hypophosphorous acid, polyphosphoric acid, phosphorous acid, hydrofluoric acid, iodic acid, fluosilicic acid, phosphoric acid, phosphomolybdic acid, periodic acid, nitric acid, perbromic acid, perrhenic acid, sulfuric acid, boric acid, hypofluoric acid, hydrofluoric acid, aluminate acid, silicic acid, metaphosphoric acid, pyrophosphoric acid, perchloric acid, silicotungstic acid, selenoic acid, sulfonic acid, phosphotungstic acid, hydrochloric acid, carbonic acid, phosphomolybdic acid, perphosphoric acid, hydrobromic acid, phosphoric acid, hydrogen sulfuric acid, arsenic acid, boric acid, tetraboric acid, metaboric acid, perboric acid, meta arsenite, arsenical acid, pyroarsenite.
In one embodiment, the organic acid comprises one or more of formic acid, acetic acid, propionic acid, butyric acid, caprylic acid, adipic acid, oxalic acid, malonic acid, succinic acid, maleic acid, tartaric acid, benzoic acid, phenylacetic acid, phthalic acid, terephthalic acid, valeric acid, caproic acid, capric acid, stearic acid, palmitic acid, acrylic acid, citric acid, malic acid, ascorbic acid, lactic acid, succinic acid, fumaric acid, quinic acid, shikimic acid, chlorogenic acid, ellagic acid, myristic acid, diterpenoid carboxylic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid.
In a second aspect, an embodiment of the present application provides a high-purity lauroyl lysine, which is prepared by the method for preparing high-purity lauroyl lysine described in any one of the above.
The advantages or beneficial effects in the technical scheme at least comprise:
The method for preparing high-purity lauroyl lysine of the application not only protects and activates the activity of functional groups, so that positive reaction is easy to carry out, but also inhibits side reaction, namely, carboxylic acid groups are changed into specific salts by using specific alkali, and when the carboxylic acid groups encounter other alkaline substances again, other salts are not regenerated, which is extremely important for enhancing the activity of the carboxylic acid groups and improving the specificity of the next reaction. Similarly, when an amino group is changed to a specific salt with a specific acid, when the amino group encounters another acidic substance, another salt is not regenerated, and this is extremely important for enhancement of the activity of the amino group and enhancement of the specificity of the reaction in the next step. The purpose of facilitating the forward reaction and inhibiting the occurrence of side reactions can be achieved. In addition, lauroyl lysine is directly prepared from lauric acid and lysine, so that the problems of low product yield, low purity, complex process and the like caused by side reactions due to poor stability of derivatives such as lauroyl chloride are avoided. The preparation method has simple and convenient process, simple equipment and conventional and easily-controlled operation conditions, can achieve high yield and obtain high-purity products, and is suitable for industrial production.
The foregoing summary is for the purpose of the specification only and is not intended to be limiting in any way. In addition to the illustrative aspects, embodiments, and features described above, further aspects, embodiments, and features of the present application will become apparent by reference to the drawings and the following detailed description.
Drawings
It is appreciated that these drawings depict only some embodiments according to the disclosure and are not therefore to be considered limiting of its scope.
FIG. 1 is a nuclear magnetic resonance spectrum of an example.
Detailed Description
Hereinafter, only certain exemplary embodiments are briefly described. As will be recognized by those of skill in the pertinent art, the described embodiments may be modified in various different ways without departing from the spirit or scope of the present application. Accordingly, the drawings and description are to be regarded as illustrative in nature and not as restrictive.
In a first aspect, an embodiment of the present application provides a method for preparing high-purity lauroyl lysine, including:
Step S1, lauric acid is dissolved in ethanol, and an aqueous solution of inorganic alkali or organic alkali is added, after the reaction, a rotary evaporator is used for removing the solution, and vacuum drying is carried out to obtain laurate;
S2, dissolving L-lysine in water, adding an aqueous solution of an inorganic acid or an organic acid, removing the solution by a rotary evaporator after the reaction, and drying in vacuum to obtain L-lysine salt;
s3, dissolving laurate and L-lysine salt in glycol, carrying out reflux reaction, removing the solution by using a rotary evaporator, and carrying out vacuum drying to obtain a lauroyl L-lysine crude product;
and S4, dissolving the lauroyl L-lysine crude product in an inorganic acid or organic acid solution, neutralizing with an inorganic base or organic alkali solution, collecting precipitated crystals, washing with water, and drying in vacuum to obtain the lauroyl L-lysine with high purity.
In one embodiment, the inorganic base comprises one or more of sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, lithium hydroxide, magnesium hydroxide, zinc hydroxide, copper hydroxide, iron hydroxide, lead hydroxide, cobalt hydroxide, chromium hydroxide, zirconium hydroxide, nickel hydroxide, ammonium hydroxide, anhydrous sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate.
In one embodiment, the organic base comprises one or more of methylamine, ethylamine, dimethylamine, diethylamine, pyridine, quinoline, 1- (3-methyl-benzofuranyl) ethanone, acetone, butanone, pentanone, hexanone, heptanone, octanone, arbitrary ketone, sodium methoxide, potassium ethoxide, potassium tert-butoxide, an alkyllithium reagent, a grignard reagent, a quaternary ammonium hydroxide, butyllithium, phenyllithium, lithium diisopropylamide, lithium hexamethyldisilazide, a quaternary ammonium base, a quaternary phosphonium base, sulfonium ions, guanidine compounds, sodium methoxide, potassium ethoxide, potassium tert-butoxide.
In one embodiment, the inorganic acid comprises one or more of hydrobromic acid, hypobromous acid, hydroiodic acid, hypophosphorous acid, polyphosphoric acid, phosphorous acid, hydrofluoric acid, iodic acid, fluosilicic acid, phosphoric acid, phosphomolybdic acid, periodic acid, nitric acid, perbromic acid, perrhenic acid, sulfuric acid, boric acid, hypofluoric acid, hydrofluoric acid, aluminate acid, silicic acid, metaphosphoric acid, pyrophosphoric acid, perchloric acid, silicotungstic acid, selenoic acid, sulfonic acid, phosphotungstic acid, hydrochloric acid, carbonic acid, phosphomolybdic acid, perphosphoric acid, hydrobromic acid, phosphoric acid, hydrogen sulfuric acid, arsenic acid, boric acid, tetraboric acid, metaboric acid, perboric acid, meta arsenite, arsenical acid, pyroarsenite.
In one embodiment, the organic acid comprises one or more of formic acid, acetic acid, propionic acid, butyric acid, caprylic acid, adipic acid, oxalic acid, malonic acid, succinic acid, maleic acid, tartaric acid, benzoic acid, phenylacetic acid, phthalic acid, terephthalic acid, valeric acid, caproic acid, capric acid, stearic acid, palmitic acid, acrylic acid, citric acid, malic acid, ascorbic acid, lactic acid, succinic acid, fumaric acid, quinic acid, shikimic acid, chlorogenic acid, ellagic acid, myristic acid, diterpenoid carboxylic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid.
Examples
Step 101, dissolving 0.35 mol of lauric acid in 200m l ethanol, and adding an aqueous solution of inorganic base or organic base, wherein water is 150m l, the inorganic base is 0.35 mol, sodium hydroxide, sodium carbonate and carbonic acid are preferably selected as the inorganic base in the embodiment, and ethylamine, butanone, sodium methoxide and other organic bases can be preferably selected as the inorganic base in other embodiments; the reaction was carried out at 25-60℃for 1-4 hours, the solution was removed at 50-90℃by rotary evaporator and dried at 100℃for 12 hours under vacuum to give 69.12g of laurate in yield: 98.58%. The reaction formula of the step is as follows:
Step 102, dissolving 0.35 mol L-lysine in 200m L water, and adding aqueous solution of inorganic acid, preferably inorganic acid: hydrobromic acid, sulfuric acid and boric acid, and in other embodiments organic acids such as acetic acid, lactic acid and oleic acid may be preferably selected, wherein water 200m l, inorganic acid 1.40 mol; reacting at 30-80 ℃ for 3-7 hours, removing the solution at 80-110 ℃ by a rotary evaporator, and vacuum drying at 100 ℃ for 12 hours to obtain 50.20g L-lysine salt, yield: 98.10%. The reaction formula of the step is as follows:
Step 103, dissolving 0.25mol of laurate and 0.25mol of L-lysine salt in 5000m L glycol, carrying out reflux reaction at 100-200 ℃ for 5-15 hours, removing the solution at 80-110 ℃ by a rotary evaporator, and drying in vacuum at 120 ℃ for 12 hours to obtain 83.12g of lauroyl L-lysine crude product, and obtaining the yield: 96.04%. The reaction formula of the step is as follows:
step 104, dissolving 0.25 mol of lauroyl L-lysine crude product in an inorganic acid solution (preferably inorganic acid such as hydrobromic acid, sulfuric acid and boric acid in the embodiment, and preferably organic acid such as acetic acid, lactic acid and oleic acid in other embodiments), neutralizing to pH2-5 with an inorganic alkali solution (preferably inorganic alkali such as sodium hydroxide, sodium carbonate and carbonic acid in the embodiment, and preferably organic alkali such as ethylamine, butanone and sodium methoxide in other embodiments), collecting precipitated crystals, washing the precipitated crystals to pH7, and vacuum-drying at 100 ℃ for 12 hours to obtain 78.24g of high-purity lauroyl L-lysine, yield: 94.13%, purity: 100%. The reaction formula of the step is as follows:
The applicant entrusts the detection mechanism to detect the high-purity lauroyl lysine prepared in the embodiment, and respectively detects the melting point and the purity, and the detection results are shown in table 1 and table 2:
TABLE 1
TABLE 2
As is clear from the results of the examination in Table 1, the melting point of the high-purity lauroyl lysine obtained in this example was 229 to 231℃and the melting point literature value of the high-purity lauroyl lysine was 229.5 to 230.5 ℃and the high-purity lauroyl lysine obtained in this example clearly meets the characteristics of the high-purity lauroyl lysine.
As is clear from the results of the examination in Table 2, the product having a purity of almost 100% was obtained by HPLC (high pressure liquid chromatography), which means that the purity of lauroyl lysine obtained in this example was very high, exceeding the average level of lauroyl lysine purity in the prior art.
In addition, the applicant also carried out Nuclear Magnetic Resonance (NMR) detection of the high purity lauroyl lysine obtained in this example, and the obtained spectrum is shown in fig. 1.
CH3(CH2)10CONH(CH2)4CH(NH2)COOH
1H NMR(400MHz,CD3OD)δ0.60～0.85(t,3H CH3(CH2)10CONH),1.05～1.35(s,18H CH3(CH2)9CH2CONH),1.36～1.65(m,6H CH3(CH2)10CONHCH2(CH2)3CH(NH2),2.01～2.21(t,2H CH2(CH2)3CH(NH2),2.95～3.09(t,2H CH3(CH2)8CH2CH2CONH),3.10～3.17(t,1H CONH(CH2)4CH(NH2)COOH).
By means of the NMR spectrum, it is clearly seen that the molecular structure of lauroyl lysine has been successfully formed, achieving the desired aim. The theory and practice of the present application agree.
In a second aspect, the embodiment of the application provides a high-purity lauroyl lysine, which is prepared by the preparation method of the high-purity lauroyl lysine.
The Chinese patent application No. 201210070584.0 discloses a preparation method of epsilon-N-lauroyl lysine, which takes lysine or salt thereof and lauroyl chloride as raw materials, firstly forms chelate with divalent metal ions to form protection of alpha-amino and carboxyl, then makes the chelate and lauroyl chloride undergo amidation reaction, finally breaks the chelate structure through acidolysis to deprotect the alpha-amino and carboxyl, and thus epsilon-N-lauroyl lysine is obtained. The patent uses lauroyl chloride as a starting material, i.e., lauroyl chloride, in order to enhance its reactivity. The fatal weakness is that acid chlorides are extremely sensitive to moisture and decompose upon contact with moisture (the degree of sensitivity of acid chlorides to moisture: opening the reagent bottle cap and immediately decomposing without immediate placement in a dry, closed environment), i.e., lauroyl chloride is decomposed into lauric acid. In this way, it is very difficult to obtain a high purity product. It is impossible to achieve high yields because of the inability to control the side reactions (decomposition) of the acid chloride.
The method for preparing high-purity lauroyl lysine of the application not only protects and activates the activity of functional groups, so that positive reaction is easy to carry out, but also inhibits side reaction, namely, carboxylic acid groups are changed into specific salts by using specific alkali, and when the carboxylic acid groups encounter other alkaline substances again, other salts are not regenerated, which is extremely important for enhancing the activity of the carboxylic acid groups and improving the specificity of the next reaction. Similarly, when an amino group is changed to a specific salt with a specific acid, when the amino group encounters another acidic substance, another salt is not regenerated, and this is extremely important for enhancement of the activity of the amino group and enhancement of the specificity of the reaction in the next step. The purpose of facilitating the forward reaction and inhibiting the occurrence of side reactions can be achieved. In addition, lauroyl lysine is directly prepared from lauric acid and lysine, so that the problems of low product yield, low purity, complex process and the like caused by side reactions due to poor stability of derivatives such as lauroyl chloride are avoided. The preparation method has simple and convenient process, simple equipment and conventional and easily-controlled operation conditions, can achieve high yield and obtain high-purity products, and is suitable for industrial production. Based on the document retrieval range, the preparation method of the application has not been reported yet.
In the description of the present specification, a description referring to terms "one embodiment," "some embodiments," "examples," "specific examples," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present application. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, the different embodiments or examples described in this specification and the features of the different embodiments or examples may be combined and combined by those skilled in the art without contradiction.
Furthermore, the terms "first," "second," and the like, are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include at least one such feature. In the description of the present application, the meaning of "a plurality" is two or more, unless explicitly defined otherwise.
The foregoing is merely illustrative of the present application, and the present application is not limited thereto, and any person skilled in the art will readily recognize that various changes and substitutions are possible within the scope of the present application. Therefore, the protection scope of the application is subject to the protection scope of the claims.

Claims (10)

1. A method for preparing high-purity lauroyl lysine, comprising the steps of:
Dissolving lauric acid in ethanol, adding aqueous solution of inorganic base or organic base, removing the solution by a rotary evaporator after reaction, and vacuum drying to obtain laurate;
Dissolving L-lysine in water, adding an aqueous solution of an inorganic acid or an organic acid, removing the solution by a rotary evaporator after the reaction, and drying in vacuum to obtain L-lysine salt;
Dissolving laurate and L-lysine salt in glycol, carrying out reflux reaction, removing the solution by using a rotary evaporator, and vacuum drying to obtain lauroyl L-lysine crude product;
dissolving the lauroyl L-lysine crude product in inorganic acid or organic acid solution, neutralizing with inorganic alkali or organic alkali solution, collecting precipitated crystals, washing with water, and vacuum drying to obtain high-purity lauroyl L-lysine.
2. The method for producing high-purity lauroyl lysine according to claim 1, wherein 0.35mol of lauric acid is dissolved in 200ml of ethanol, and an aqueous solution of an inorganic base or an organic base is added, wherein 150ml of water, 0.35mol of inorganic base or organic base; the reaction was carried out at 25-60℃for 1-4 hours, the solution was removed at 50-90℃by a rotary evaporator, and vacuum-dried at 100℃for 12 hours to obtain laurate.
3. The method for producing high-purity lauroyl lysine according to claim 2, wherein 0.35mol of L-lysine is dissolved in 200ml of water, and an aqueous solution of an inorganic acid or an organic acid is added, wherein 200ml of water, 1.40mol of an inorganic acid or an organic acid; the reaction is carried out at 30-80℃for 3-7 hours, the solution is removed at 80-110℃by a rotary evaporator, and the solution is dried at 100℃for 12 hours under vacuum to obtain the L-lysine salt.
4. The method for producing high-purity lauroyl lysine according to claim 3, wherein 0.25mol of laurate and 0.25mol of L-lysine salt are dissolved in 5000ml of ethylene glycol, reflux reaction is performed at 100 to 200℃for 5 to 15 hours, the solution is removed at 80 to 110℃by a rotary evaporator, and vacuum drying is performed at 120℃for 12 hours to obtain crude lauroyl L-lysine.
5. The method for producing high-purity lauroyl lysine according to claim 4, wherein 0.25mol of lauroyl L-lysine crude product is dissolved in an inorganic acid or an organic acid solution, neutralized to pH2-5 with an inorganic base or an organic base solution, precipitated crystals are collected, washed to pH7 with water, and vacuum-dried at 100℃for 12 hours to obtain high-purity lauroyl L-lysine.
6. The method for producing high-purity lauroyl lysine according to any one of claims 1 to 5, wherein the inorganic base comprises one or more of sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, lithium hydroxide, magnesium hydroxide, zinc hydroxide, copper hydroxide, iron hydroxide, lead hydroxide, cobalt hydroxide, chromium hydroxide, zirconium hydroxide, nickel hydroxide, ammonium hydroxide, anhydrous sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate.
7. The method for preparing high purity lauroyl lysine according to any of claims 1 to 5, wherein the organic base comprises one or more of methylamine, ethylamine, dimethylamine, diethylamine, pyridine, quinoline, 1- (3-methyl-benzofuranyl) ethanone, acetone, butanone, pentanone, hexanone, heptanone, octanone, arbitrary ketone, sodium methoxide, potassium ethoxide, potassium tert-butoxide, alkyl lithium reagent, grignard reagent, quaternary ammonium hydroxide, butyl lithium, phenyl lithium, lithium diisopropylamide, lithium hexamethyldisilamide, quaternary ammonium base, quaternary phosphonium base, sulfonium ion, guanidine compound, sodium methoxide, potassium ethoxide, potassium tert-butoxide.
8. The method for producing high purity lauroyl lysine according to any one of claims 1 to 5, wherein the inorganic acid comprises one or more of hydrobromic acid, hypobromous acid, hydroiodic acid, hypophosphorous acid, polyphosphoric acid, phosphorous acid, hydrofluoric acid, iodic acid, fluosilicic acid, phosphoric acid, phosphomolybdic acid, periodic acid, nitric acid, hydrobromic acid, perrhenic acid, pyrosulfuric acid, sulfuric acid, boric acid, hypofluoric acid, hydrofluoric acid, aluminate acid, silicic acid, metaphosphoric acid, pyrophosphoric acid, silicotungstic acid, selenoic acid, sulfonic acid, phosphotungstic acid, hydrochloric acid, carbonic acid, phosphomolybdic acid, perphosphoric acid, hydrobromic acid, phosphoric acid, hydrogen sulfuric acid, arsenic acid, boric acid, tetraboric acid, metaboric acid, perboric acid, meta arsenite, arsenite.
9. The method for producing high purity lauroyl lysine according to any one of claims 1 to 5, wherein the organic acid comprises one or more of formic acid, acetic acid, propionic acid, butyric acid, caprylic acid, adipic acid, oxalic acid, malonic acid, succinic acid, maleic acid, tartaric acid, benzoic acid, phenylacetic acid, phthalic acid, terephthalic acid, valeric acid, capric acid, stearic acid, palmitic acid, acrylic acid, citric acid, malic acid, ascorbic acid, lactic acid, succinic acid, fumaric acid, quinic acid, shikimic acid, chlorogenic acid, ellagic acid, myristic acid, diterpene carboxylic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid.
10. A high purity lauroyl lysine prepared by the method of any one of claims 1-9.
CN202410500766.XA 2024-04-24 2024-04-24 High-purity lauroyl lysine and preparation method thereof Pending CN118388363A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202410500766.XA CN118388363A (en) 2024-04-24 2024-04-24 High-purity lauroyl lysine and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202410500766.XA CN118388363A (en) 2024-04-24 2024-04-24 High-purity lauroyl lysine and preparation method thereof

Publications (1)

Publication Number Publication Date
CN118388363A true CN118388363A (en) 2024-07-26

Family

ID=92000794

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202410500766.XA Pending CN118388363A (en) 2024-04-24 2024-04-24 High-purity lauroyl lysine and preparation method thereof

Country Status (1)

Country Link
CN (1) CN118388363A (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102617390A (en) * 2012-03-16 2012-08-01 张家港市华昌药业有限公司 Preparation method of epsilon-N-lauroyl lysine
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
US20180230502A1 (en) * 2015-11-12 2018-08-16 Ajinomoto Co., Inc. METHOD FOR PRODUCING N Epsilon-ACYL-L-LYSINE
CN114933545A (en) * 2022-03-02 2022-08-23 上海常丰生物医药科技有限公司 Method for synthesizing lauroyl lysine
CN117164470A (en) * 2023-08-09 2023-12-05 长沙普济生物科技股份有限公司 High-purity N ε Synthesis method of lauroyl lysine

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102617390A (en) * 2012-03-16 2012-08-01 张家港市华昌药业有限公司 Preparation method of epsilon-N-lauroyl lysine
US20180230502A1 (en) * 2015-11-12 2018-08-16 Ajinomoto Co., Inc. METHOD FOR PRODUCING N Epsilon-ACYL-L-LYSINE
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
CN114933545A (en) * 2022-03-02 2022-08-23 上海常丰生物医药科技有限公司 Method for synthesizing lauroyl lysine
CN117164470A (en) * 2023-08-09 2023-12-05 长沙普济生物科技股份有限公司 High-purity N ε Synthesis method of lauroyl lysine

Similar Documents

Publication Publication Date Title
TWI546311B (en) Method for producing grass killing P free acid
CN103922968B (en) Preparation method of hydroxamic acid or hydroxamic acid salt
KR100966627B1 (en) Method for preparing L-α-glycerophosphoryl choline
JP5918670B2 (en) Method for producing acetylated sulfonium compound
US20110295035A1 (en) Method for producing phenylacetamide compound
CN104693114A (en) Improved method for preparing betrixaban
KR890001883B1 (en) Process for the preparation of ethyleneglycol and prophyeneglycol
CN101616890A (en) Preparation does not contain method, its synthetic intermediate and a kind of new crystalline form of the Entacapone of Z-isomer substantially
US20170275247A1 (en) Method for producing methionine
CN109897070B (en) Preparation method of tetraamminepalladium acetate (II)
US9776953B2 (en) Isolation and purification of 6-aminocaproic acid
CN118388363A (en) High-purity lauroyl lysine and preparation method thereof
JPWO2007145278A1 (en) Method for producing glycidol
US20230295078A1 (en) Method for preparing guanidino acetic acid
CN112831090A (en) Preparation method of epoxidized calcium zinc oleate for PVC heat stabilizer
US9758471B2 (en) Process for the preparation of 4-dimethylaminocrotonic acid
JP5412669B2 (en) Method for producing 4,4'-dihydroxydiphenyl ether
EP0926140B1 (en) Method for preparing 2-mercaptothiazole
CN101987837B (en) Preparation method of 1,2,4-thiadiazole oximido acetic acid compound
CN104557561A (en) Method for preparing N1,N1-diisoprylamino ethylamine or salts of N1,N1-diisoprylamino ethylamine
JP3931737B2 (en) Method for producing quaternary ammonium halide salt
US20040002618A1 (en) Process for producing a calcium carboxylate
JP5648327B2 (en) Method for producing high purity o-tolidine sulfone
CN111763152B (en) Preparation method of acetamido substance
CN118843622A (en) Preparation method of lebol Lei Sheng and intermediate compound thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination