CN107286059A - A kind of preparation method of lauroyl arginine ethyl ester hydrochloride - Google Patents
A kind of preparation method of lauroyl arginine ethyl ester hydrochloride Download PDFInfo
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- CN107286059A CN107286059A CN201710355160.1A CN201710355160A CN107286059A CN 107286059 A CN107286059 A CN 107286059A CN 201710355160 A CN201710355160 A CN 201710355160A CN 107286059 A CN107286059 A CN 107286059A
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- CN
- China
- Prior art keywords
- lauroyl
- arginine
- ethyl ester
- ester hydrochloride
- organic solvent
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- XTJKNGLLPGBHHO-HNNXBMFYSA-N (2s)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCCN=C(N)N XTJKNGLLPGBHHO-HNNXBMFYSA-N 0.000 title claims abstract description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003960 organic solvent Substances 0.000 claims abstract description 28
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000000047 product Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000012043 crude product Substances 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 239000004475 Arginine Substances 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000005119 centrifugation Methods 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000012046 mixed solvent Substances 0.000 claims abstract description 11
- 239000012044 organic layer Substances 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 5
- 230000033228 biological regulation Effects 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 25
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 13
- KWTQSFXGGICVPE-UHFFFAOYSA-N 2-amino-5-(diaminomethylideneamino)pentanoic acid;hydron;chloride Chemical compound Cl.OC(=O)C(N)CCCN=C(N)N KWTQSFXGGICVPE-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 12
- 229960003121 arginine Drugs 0.000 claims description 10
- 235000009697 arginine Nutrition 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 235000011181 potassium carbonates Nutrition 0.000 claims description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000011736 potassium bicarbonate Substances 0.000 claims description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- CGKQZIULZRXRRJ-UHFFFAOYSA-N Butylone Chemical compound CCC(NC)C(=O)C1=CC=C2OCOC2=C1 CGKQZIULZRXRRJ-UHFFFAOYSA-N 0.000 claims 1
- GUUNMTFSWQFNCZ-UHFFFAOYSA-I C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.[K+].[C+4].C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O Chemical compound C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.[K+].[C+4].C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O GUUNMTFSWQFNCZ-UHFFFAOYSA-I 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 12
- 239000002537 cosmetic Substances 0.000 abstract description 6
- 235000013305 food Nutrition 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000003755 preservative agent Substances 0.000 description 10
- 230000002335 preservative effect Effects 0.000 description 10
- AKGWUHIOEVNNPC-LURJTMIESA-N Arg-OEt Chemical compound CCOC(=O)[C@@H](N)CCCNC(N)=N AKGWUHIOEVNNPC-LURJTMIESA-N 0.000 description 9
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000010586 diagram Methods 0.000 description 6
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 5
- 235000019082 Osmanthus Nutrition 0.000 description 5
- 241000333181 Osmanthus Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 4
- 229940070765 laurate Drugs 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- KWTQSFXGGICVPE-WCCKRBBISA-N Arginine hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCCN=C(N)N KWTQSFXGGICVPE-WCCKRBBISA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000001408 fungistatic effect Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 239000005452 food preservative Substances 0.000 description 2
- 235000019249 food preservative Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000013580 sausages Nutrition 0.000 description 2
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- FPZYYTJCVCQSTI-RGMNGODLSA-N C(=O)(OCC)Cl.C(CC)N[C@@H](CCO)C(=O)O Chemical compound C(=O)(OCC)Cl.C(CC)N[C@@H](CCO)C(=O)O FPZYYTJCVCQSTI-RGMNGODLSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NWSBNVVOFKKFNV-UHFFFAOYSA-N chloroform;oxolane Chemical compound ClC(Cl)Cl.C1CCOC1 NWSBNVVOFKKFNV-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000007247 enzymatic mechanism Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000021472 generally recognized as safe Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3526—Organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
The invention discloses a kind of preparation method of lauroyl arginine ethyl ester hydrochloride, belong to technical field of organic synthesis.This method includes：L arginine monohydrochlorides react in the in the mixed solvent that water and organic solvent A are constituted with lauroyl chloride, after the completion of reaction, and regulation pH value centrifuges to 59, is dried to obtain lauroyl arginine；Lauroyl arginine and ethanol and thionyl chloride are reacted, is evaporated after the completion of reaction and obtains crude product；Crude product is dissolved in organic solvent B, plus alkaline aqueous solution adjusts pH value to 58, stirring, standing take organic layer, lauroyl arginine ethyl ester hydrochloride fine work are obtained after decrease temperature crystalline, centrifugation and drying.The preparation method that the present invention is provided has few, easily separated easy to operate, accessory substance, easy drying and easily crushing etc., major impurity in product is effectively removed in preparation process, the fine grained lauroyl arginine ethyl ester hydrochloride of high-purity can be obtained, it is adapted to large-scale production, product is widely used in foods and cosmetics industry.
Description
Technical field
The invention belongs to organic synthesis field, and in particular to a kind of preparation method of lauroyl arginine ethyl ester hydrochloride,
More particularly to a kind of preparation method of lauroyl arginine ethyl ester hydrochloride available for foods and cosmetics preservative.
Background technology
Lauroyl arginine ethyl ester hydrochloride is a kind of new antiseptic, it was found that lauroyl arginine ethyl ester hydrochloric acid
Salt has very strong fungistatic effect to Gram-negative and gram-positive bacterium, yeast and mould.Its mechanism of action is the moon
Osmanthus acyl arginine ethyl ester hydrochloride is a kind of cationic surfactant, and it can influence film negatively charged in bacterial cell membrane
Albumen and enzymatic mechanism, change membrane passage, reach the growth for suppressing microorganism or make microorganism deactivated effect.
Lauroyl arginine ethyl ester hydrochloride has fabulous security, its mesostate in human body and final
Product is all native endogenous substances, and it is by experimental results demonstrate being a kind of low toxicity, safety, efficient preservative, in food and
Cosmetic industry has a wide range of applications, wide market, there is potential commercial value.
2005, U.S. FDA endorsed letter without demur, announces lauroyl arginine ethyl ester hydrochloride and is eaten by generally recognized as safe
Product certification, while United States Department of Agriculture also allows its use in meat product and birds food.
2009, European Union ratified lauroyl arginine ethyl ester hydrochloride as preservative and used in cosmetics first.
2013, pest management office of Her Majesty the Queen in right of Canada as represented by the minister of Healt was issued on lauroyl arginine ethyl ester hydrochloride conduct
Various standardization and the motion of nonstandardized technique food preservative.
2014, the issue committee of European Union regulations approval lauroyl arginine ethyl ester hydrochloride was used for hot-working meat as preservative
Product（Except Emulsification Sausages, summer sausage and Liver paste）.
2016, European Union is newly-increased to allow lauroyl arginine ethyl ester hydrochloride as preservative for mouthwash.
Analyzed by global cosmetics preservative frequency of use in recent years, the use total amount of preservative has obvious falling tendency,
And ascendant trend is integrally presented in foodstuff preservative.As new legislation is used methylisothiazolinone and oxybenzene esters preservative
Limitation because it is safe and efficient the characteristics of, will obtain more next as the lauroyl arginine ethyl ester hydrochloride of new food preservative
More applications.Therefore it provides a kind of raw material is easy to get, technique is simple, and accessory substance is few, the high lauroyl arginine ethyl ester salt of purity
The preparation method of hydrochlorate, is significant.
At present, the preparation method in document on lauroyl arginine ethyl ester hydrochloride mainly has following several：
(1) Vishwas etc. is using arginine ethyl ester hydrochloride as raw material, using water as solvent, and sodium hydroxide makees alkali, exists with lauroyl chloride
Acylation reaction obtains lauroyl arginine ethyl ester hydrochloride under weak basic condition.(2) Dilip using arginine ethyl ester hydrochloride as
Raw material, using organic solvents, chloroform tetrahydrofuran as solvent, triethylamine makees alkali, with lauroyl chloride under weak basic condition acylation reaction
Obtain lauroyl arginine ethyl ester hydrochloride.The thinking is using arginine ethyl ester hydrochloride as raw material, and cost is higher, is unfavorable for industry
Metaplasia is produced.(3) Francisco is using arginine as raw material, and ethanol is solvent, and thionyl chloride is catalyst, is first esterified at room temperature anti-
Should generate arginine ethyl ester hydrochloride, it is post-treated after first step crude product is dissolved in after water, then adjust pH with sodium hydroxide solution,
Lauroyl arginine ethyl ester hydrochloride is obtained with lauroyl chloride acylation reaction.This method uses arginine monohydrochloride instead for raw material, into
This is relatively low, and beneficial to industrialized production, but the reaction is carried out in strong alkali aqueous solution, and lauroyl chloride is under aqueous basic conditions
Facile hydrolysis is laurate, and lauroyl arginine ethyl ester hydrochloride crystal formation in water is bad, and wet product contains substantial amounts of water after centrifugation,
Remaining raw material and impurity arginine, arginine ethyl ester, ethyl laurate and the sodium chloride of generation etc. all will be with course of reaction
Water is remained in the product, causes the content and purity of product not high（Purity only has 90% or so）, add lauroyl arginine ethyl ester
HCI m. p is 50-58 DEG C, and being separated from the water when obtained lauroyl arginine ethyl ester hydrochloride is dried that temperature is slightly higher will
There is melting water rem oval under phenomenon, low temperature very low, it is dry difficult.In addition, Xavier is proved by Bioexperiment, lauroyl essence
The fungistatic effect of propylhomoserin carbethoxy hydrochloride is relevant with its granularity：Product granularity is smaller, and antibacterial effect is better, and isolated in water
Lauroyl arginine ethyl ester hydrochloride granularity is generally larger after being pulverized.
The content of the invention
, should the invention provides a kind of preparation method of lauroyl arginine ethyl ester hydrochloride in order to solve the above problems
The basic ideas of method are first to prepare lauroyl arginine using L-arginine hydrochloride and lauroyl chloride, then are esterified, and are located
Lauroyl arginine ethyl ester hydrochloride is obtained after reason.Wherein, lauroyl arginine has preferable crystal formation in the mixed solvent, it is easy to
The impurity such as sodium chloride or potassium chloride that centrifugation, the complete arginine of unreacted and reaction are produced are dissolved in water, can realize effectively removal；Month
The laurate that osmanthus acyl chlorides hydrolysis is produced generates ethyl laurate in esterif iotacation step, is dissolved in organic solvent and is easy to separate with product, ester
Processing stage after change, water-solubility impurity arginine, arginine ethyl ester and sodium chloride or potassium chloride are water-soluble, further reduce
The content of impurity in product, final products are separated out in the volatile organic solvent of low boiling, can be achieved under low temperature quick dry
It is dry, and granularity is smaller after crushing, there is more preferable antibacterial effect.This method has that easy to operate, accessory substance is few, easily separated, Yi Gan
Major impurity in the advantages of dry and easy crushing, product is effectively removed in preparation process, can obtain the granule of high-purity
Lauroyl arginine ethyl ester hydrochloride is spent, is adapted to industrialized production.Its technical scheme is as follows：
The embodiments of the invention provide a kind of preparation method of lauroyl arginine ethyl ester hydrochloride, this method includes following step
Suddenly：
(1) L-arginine hydrochloride reacts in the in the mixed solvent that water and organic solvent A are constituted with lauroyl chloride, reaction condition
For：Plus alkali regulation pH is 7-12, reaction temperature is -5 DEG C -30 DEG C, and the mol ratio of L-arginine hydrochloride and lauroyl chloride is 1：
0.8-1.2；After the completion of reaction, acid adding（Such as watery hydrochloric acid）PH value is adjusted to 5-9（It is easy to lauroyl arginine preferably to precipitate）, from
The heart, it is dried to obtain lauroyl arginine.
(2) the lauroyl arginine for obtaining step (1) is reacted with ethanol and thionyl chloride, and ethanol is evaporated after the completion of reaction
Crude product is obtained with thionyl chloride.
(3) crude product for obtaining step (2) is dissolved in organic solvent B, plus alkaline aqueous solution adjusts pH value to 5-8, stirs,
Stand, take organic layer, lauroyl arginine ethyl ester hydrochloride fine work is obtained after decrease temperature crystalline, centrifugation, dry and crushing.
Wherein, in step (1), the one kind of organic solvent A in acetone, butanone, ethyl acetate and butyl acetate etc.
Or it is a variety of.
Wherein, in step (1), the mass ratio of mixed solvent and L-arginine hydrochloride is 5-15：1, water with it is organic molten
Agent A mass ratio is 1：0.25-4.
Wherein, in step (1), plus pH is adjusted to 7-12 by alkali.Specifically, alkali is selected from sodium hydroxide solution, hydroxide
Potassium solution, sodium bicarbonate solution, potassium bicarbonate solution, sodium carbonate liquor or solution of potassium carbonate etc..
Wherein, in step (2), reaction condition is：The mol ratio of lauroyl arginine and thionyl chloride is 1：0.5-
2.0, the weight ratio of lauroyl arginine and ethanol is 1：2-8, reaction temperature is -5 DEG C and extremely flowed back that the reaction time is that 3-10 is small
When.
Wherein, in step (3), organic solvent B is 2-10 with the arginic mass ratio of lauroyl：1, organic solvent B choosing
One or more from ethyl acetate, butyl acetate, dichloromethane, petroleum ether, tetrahydrofuran and n-hexane etc..
Wherein, in step (3), it is molten that alkaline aqueous solution is selected from sodium hydroxide solution, potassium hydroxide solution, sodium acid carbonate
Liquid, potassium bicarbonate solution, sodium carbonate liquor or solution of potassium carbonate etc..
Further, the preparation method for the lauroyl arginine ethyl ester hydrochloride that the present invention is provided comprises the following steps：
(1) L-arginine hydrochloride is dissolved in the in the mixed solvent that water is constituted with organic solvent A, lauroyl chloride, temperature control is added dropwise
System is at -5 DEG C -30 DEG C, plus alkali controls pH in 7-12, is added dropwise to complete latter stirring reaction 1-5 hours, after the completion of reaction, acid adding（Salt
Acid）PH value is adjusted to 5-9, centrifuges, be dried to obtain lauroyl arginine.Wherein, the matter of mixed solvent and L-arginine hydrochloride
Amount is than being 5-15：1, the mass ratio of water and organic solvent A is 1：0.25-4, organic solvent A is selected from acetone, butanone, ethyl acetate
With the one or more in butyl acetate etc., alkali is selected from sodium hydroxide solution, potassium hydroxide solution, sodium bicarbonate solution, carbonic acid
Hydrogen potassium solution, sodium carbonate liquor or solution of potassium carbonate etc..Referring to Fig. 1, left side is lauroyl arginine ethyl ester salt in the prior art
The crystallization schematic diagram of hydrochlorate, right side is the arginic crystallization schematic diagram of lauroyl obtained using the present invention, can from figure
Go out obtained lauroyl arginine of the invention to be easily isolated.
(2) the lauroyl arginine for obtaining step (1) is added in ethanol, adds thionyl chloride, and reaction temperature is -5
DEG C to flow back, the reaction time be 3-10 hours, ethanol is evaporated after the completion of reaction and thionyl chloride obtains crude product；Wherein, lauroyl
The mol ratio of arginine and thionyl chloride is 1：The weight ratio of 0.5-2.0, lauroyl arginine and ethanol is 1：2-8.
(3) crude product obtained in step (2) is added in organic solvent B, plus alkaline aqueous solution adjusts pH value to 5-8,
Stirring, standing, take organic layer, and organic layer obtains lauroyl arginine ethyl ester hydrochloric acid after decrease temperature crystalline, centrifugation, dry and crushing
Salt fine work；Wherein, organic solvent B and the arginic mass ratio of lauroyl are 2-10：1, organic solvent B is selected from ethyl acetate, second
One or more in acid butyl ester, dichloromethane, petroleum ether, tetrahydrofuran and n-hexane etc., alkaline aqueous solution is selected from hydroxide
Sodium solution, potassium hydroxide solution, sodium bicarbonate solution, potassium bicarbonate solution, sodium carbonate liquor or solution of potassium carbonate etc..Wherein,
Lauroyl arginine ethyl ester hydrochloride crystallization effect in this step is with the right side of Fig. 1, and crystallization effect is good, it is easy to separate.Referring to figure
2, left side is the granular size schematic diagram of lauroyl arginine ethyl ester hydrochloride in the prior art, and right side is to be obtained using the present invention
Lauroyl arginine ethyl ester hydrochloride granular size schematic diagram, as can be seen from the figure the obtained particle of the present invention is more existing
Technology is much smaller, can have more preferable fungistatic effect, be more suitable for foods and cosmetics preservative etc..
Compared with prior art, the present invention has advantages below：
(1) it is initiation material from L-arginine hydrochloride cheap and easy to get, cost is relatively low.
(2) the major impurity laurate produced in system is converted into liquid ethyl laurate during the course of the reaction, can be smooth
Realize and separate with product.
(3) impurity arginine, arginine ethyl ester and sodium chloride or potassium chloride for being produced in system etc. are in processing procedure
Into water layer, it can smoothly realize and separate with product.
(4) product is separated out and separated in recrystallisation solvent, and solvent is easy to remove in drying process.
(5) lauroyl arginine is good in the crystallization effect of in the mixed solvent, it is easy to which impurity is separated, it is to avoid impurity is brought into subsequently
Reaction, and in product crystallization process, the crystallization effect of product is equally fine, is also easy to impurity separation；The then impurity in product
Laurate, arginine, arginine ethyl ester and sodium chloride or potassium chloride etc. are separated in preparation process with product, and product purity is non-
Chang Gao, high purity more than 98%.
(6) product is separated out in recrystallisation solvent, and preferably, the product granularity finally given is smaller for crystal formation.
Brief description of the drawings
Fig. 1 is the lauroyl arginine knot that the lauroyl arginine ethyl ester hydrochloride that prior art is obtained is obtained with this patent
Brilliant situation comparison diagram；
Fig. 2 is the granular size comparison diagram for the lauroyl arginine ethyl ester hydrochloride that prior art is obtained with the present invention.
Embodiment
To make the object, technical solutions and advantages of the present invention clearer, the present invention is made into one below in conjunction with accompanying drawing
It is described in detail on step ground.
Embodiment 1：
It is pumped into 60kg water and 60kg acetone successively into 200L reactors, arginine monohydrochloride 21kg is added in reactor,
Stirring and dissolving, is cooled to 5 DEG C, adjusts pH value to 10 using 20wt% sodium hydrate aqueous solution, the 21.9kg months are added dropwise into system
Osmanthus acyl chlorides, while 20wt% sodium hydrate aqueous solution is added dropwise, makes pH maintain 10, temperature maintains 5 DEG C, treats that lauroyl chloride drips
Plus after the completion of, stir 2 hours, using 6mol/L salt acid for adjusting pH to 7, centrifugation, dry lauroyl arginine.By gained month
In the acyl arginine input 200L reactors of osmanthus, plus ethanol 100kg, thionyl chloride 11.9kg, flow back 5 hours, decompression steams ethanol
Crude product is obtained, ethyl acetate 150kg is added into reactor, 5wt% sodium bicarbonate aqueous solution 30kg is added, stirs, is stood
Layering, discards water layer, and organic layer cooling separates out product, and centrifugation dry, pulverize to obtain high-purity lauroyl arginine ethyl ester hydrochloride
35.8kg, purity is more than 98%, and yield is 85.2%.
Embodiment 2：
It is pumped into 60kg water and 70kg ethyl acetate successively into 200L reactors, arginine monohydrochloride 21kg is added to reactor
In, stirring and dissolving is cooled to 10 DEG C, adjusts pH value to 9 using 20wt% aqueous sodium carbonate, 21.9kg is added dropwise into system
Lauroyl chloride, while 20wt% aqueous sodium carbonate is added dropwise, makes pH maintain 9, temperature maintains 10 DEG C, treats that lauroyl chloride drips
Plus after the completion of, stir 5 hours, using 6mol/L salt acid for adjusting pH to 5, centrifugation, dry lauroyl arginine.By gained month
In the acyl arginine input 200L reactors of osmanthus, plus ethanol 80kg, thionyl chloride 13kg, 30 DEG C are reacted 9 hours, and decompression steams ethanol
Crude product is obtained, butyl acetate 150kg is added into reactor, 10wt% aqueous sodium carbonate 30kg is added, stirs, is stood
Layering, discards water layer, and organic layer cooling separates out product, and centrifugation dry, pulverize to obtain high-purity lauroyl arginine ethyl ester hydrochloride
35.2kg, purity is more than 98%, and yield is 86.2%.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent substitution and improvements made etc. should be included in the scope of the protection.
Claims (7)
1. a kind of preparation method of lauroyl arginine ethyl ester hydrochloride, it is characterised in that the described method comprises the following steps：
(1) L-arginine hydrochloride reacts in the in the mixed solvent that water and organic solvent A are constituted with lauroyl chloride, reaction condition
For：PH is 7-12, and reaction temperature is -5 DEG C -30 DEG C, and the mol ratio of the L-arginine hydrochloride and lauroyl chloride is 1：0.8-
1.2；After the completion of reaction, regulation pH value centrifuges to 5-9, is dried to obtain lauroyl arginine；
(2) the lauroyl arginine for obtaining step (1) reacts with ethanol and thionyl chloride, is evaporated after the completion of reaction and obtains thick
Product；
(3) crude product for obtaining step (2) is dissolved in organic solvent B, plus alkaline aqueous solution adjusts pH value to 5-8, stirs, quiet
Put, take organic layer, lauroyl arginine ethyl ester hydrochloride fine work is obtained through decrease temperature crystalline, centrifugation and after drying.
2. the preparation method of lauroyl arginine ethyl ester hydrochloride according to claim 1, it is characterised in that in step
(1) in, one or more of the organic solvent A in acetone, butanone, ethyl acetate and butyl acetate.
3. the preparation method of lauroyl arginine ethyl ester hydrochloride according to claim 1, it is characterised in that in step
(1) in, the mass ratio of the mixed solvent and L-arginine hydrochloride is 5-15：1, the mass ratio of the water and organic solvent A
For 1：0.25-4.
4. the preparation method of lauroyl arginine ethyl ester hydrochloride according to claim 1, it is characterised in that in step
(1) in, plus pH is adjusted to 7-12 by alkali, and the alkali is selected from sodium hydroxide solution, potassium hydroxide solution, sodium bicarbonate solution, carbon
Potassium hydrogen phthalate solution, sodium carbonate liquor or solution of potassium carbonate.
5. the preparation method of lauroyl arginine ethyl ester hydrochloride according to claim 1, it is characterised in that in step
(2) in, reaction condition is：The mol ratio of the lauroyl arginine and thionyl chloride is 1：0.5-2.0, the smart ammonia of the lauroyl
The weight ratio of acid and ethanol is 1：2-8, reaction temperature is -5 DEG C and extremely flowed back.
6. the preparation method of lauroyl arginine ethyl ester hydrochloride according to claim 1, it is characterised in that in step
(3) in, the organic solvent B is 2-10 with the arginic mass ratio of lauroyl：1, the organic solvent B be selected from ethyl acetate,
One or more in butyl acetate, dichloromethane, petroleum ether, tetrahydrofuran and n-hexane.
7. the preparation method of lauroyl arginine ethyl ester hydrochloride according to claim 1, it is characterised in that methods described
Specifically include following steps：
(1) L-arginine hydrochloride is dissolved in the in the mixed solvent that water is constituted with organic solvent A, lauroyl chloride, temperature control is added dropwise
System is at -5 DEG C -30 DEG C, plus alkali controls pH after the completion of 7-12, reaction, plus acid for adjusting pH value is to 5-9, centrifuges, be dried to obtain bay
Acyl arginine；The mass ratio of the mixed solvent and L-arginine hydrochloride is 5-15：1, the quality of the water and organic solvent A
Than for 1：0.25-4, one or more of the organic solvent A in acetone, butanone, ethyl acetate and butyl acetate are described
Alkali is selected from sodium hydroxide solution, potassium hydroxide solution, sodium bicarbonate solution, potassium bicarbonate solution, sodium carbonate liquor or potassium carbonate
Solution；
(2) the lauroyl arginine for obtaining step (1) is added in ethanol, add thionyl chloride, reaction temperature be -5 DEG C extremely
Backflow, is evaporated after the completion of reaction and obtains crude product, and the mol ratio of the lauroyl arginine and thionyl chloride is 1：0.5-2.0, institute
The weight ratio for stating lauroyl arginine and ethanol is 1：2-8；
(3) crude product obtained in step (2) is added in organic solvent B, plus alkaline aqueous solution adjusts pH value to 5-8, stirs,
Stand, take organic layer, organic layer obtains lauroyl arginine ethyl ester hydrochloride fine work, institute through decrease temperature crystalline, centrifugation and after drying
It is 2-10 that organic solvent B, which is stated, with the arginic mass ratio of lauroyl：1, the organic solvent B be selected from ethyl acetate, butyl acetate,
One or more in dichloromethane, petroleum ether, tetrahydrofuran and n-hexane.
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| CN107814754A (en) * | 2017-11-16 | 2018-03-20 | 中国日用化学工业研究院 | A kind of preparation method of lauroyl arginine ethyl ester hydrochloride |
| CN108101812A (en) * | 2018-01-02 | 2018-06-01 | 成都傲飞生物化学品有限责任公司 | A kind of production purifying process of lauroyl arginine ethyl ester hydrochloride |
| CN110279603A (en) * | 2019-07-16 | 2019-09-27 | 伊乐生物科技（广州）有限公司 | A kind of Compositional antiseptic agent and preparation method for cosmetics |
| CN110393674A (en) * | 2019-08-22 | 2019-11-01 | 南京华狮新材料有限公司 | Amino acid antibacterial agent synergy hexamidine bactericidal composition |
| CN110960445A (en) * | 2019-12-30 | 2020-04-07 | 福建恒安集团有限公司 | Anticorrosion system for baby wet tissue immersion liquid and preparation method thereof |
| WO2020184797A1 (en) * | 2019-03-11 | 2020-09-17 | 고려대학교 산학협력단 | Eco-friendly method for preparing unnatural amino acid-based antibacterial and antibiotic preservative |
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| CN110960445A (en) * | 2019-12-30 | 2020-04-07 | 福建恒安集团有限公司 | Anticorrosion system for baby wet tissue immersion liquid and preparation method thereof |
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