JP2023511462A - 塩のイオン交換法を用いた親環境高効率エステル化反応基盤のエステル化合物の製造方法およびその化合物 - Google Patents
塩のイオン交換法を用いた親環境高効率エステル化反応基盤のエステル化合物の製造方法およびその化合物 Download PDFInfo
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- -1 Ester compound Chemical class 0.000 title claims abstract description 47
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 28
- 150000003839 salts Chemical class 0.000 title claims abstract description 12
- 238000005342 ion exchange Methods 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 17
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 16
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 15
- 229940041616 menthol Drugs 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- AKGWUHIOEVNNPC-LURJTMIESA-N Arg-OEt Chemical compound CCOC(=O)[C@@H](N)CCCNC(N)=N AKGWUHIOEVNNPC-LURJTMIESA-N 0.000 claims description 12
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 10
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 235000005985 organic acids Nutrition 0.000 claims description 6
- 150000003138 primary alcohols Chemical class 0.000 claims description 6
- 150000003333 secondary alcohols Chemical class 0.000 claims description 6
- 239000005639 Lauric acid Substances 0.000 claims description 5
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 claims description 4
- 229940074391 gallic acid Drugs 0.000 claims description 4
- 235000004515 gallic acid Nutrition 0.000 claims description 4
- 229940072056 alginate Drugs 0.000 claims description 3
- 235000010443 alginic acid Nutrition 0.000 claims description 3
- 229920000615 alginic acid Polymers 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
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- 238000006460 hydrolysis reaction Methods 0.000 abstract description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract description 8
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- 235000019341 magnesium sulphate Nutrition 0.000 abstract description 4
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- 239000000376 reactant Substances 0.000 abstract description 2
- 231100001261 hazardous Toxicity 0.000 abstract 1
- 230000002085 persistent effect Effects 0.000 abstract 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 36
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 239000003377 acid catalyst Substances 0.000 description 11
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 9
- 239000003205 fragrance Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000001605 (5-methyl-2-propan-2-ylcyclohexyl) acetate Substances 0.000 description 7
- XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 7
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004262 Ethyl gallate Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- CUBZMGWLVMQKNE-LMOVPXPDSA-N ethyl (2s)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate;hydrochloride Chemical compound Cl.CCCCCCCCCCCC(=O)N[C@H](C(=O)OCC)CCCNC(N)=N CUBZMGWLVMQKNE-LMOVPXPDSA-N 0.000 description 4
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 4
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- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005792 Geraniol Substances 0.000 description 3
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000013566 allergen Substances 0.000 description 3
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- 238000009835 boiling Methods 0.000 description 3
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- 238000003912 environmental pollution Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229940113087 geraniol Drugs 0.000 description 3
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- 241000894006 Bacteria Species 0.000 description 2
- 238000007309 Fischer-Speier esterification reaction Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000002009 allergenic effect Effects 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
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- OMLOJNNKKPNVKN-UHFFFAOYSA-N 2-chloro-4-methyl-1-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(C)CC1Cl OMLOJNNKKPNVKN-UHFFFAOYSA-N 0.000 description 1
- IUTKPPDDLYYMBE-UHFFFAOYSA-N 3,4,5-trihydroxybenzoic acid;hydrate Chemical compound O.OC(=O)C1=CC(O)=C(O)C(O)=C1 IUTKPPDDLYYMBE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
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- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000005305 alkyl chloride derivatives Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940097942 gallic acid monohydrate Drugs 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- FXBYOMANNHFNQV-UHFFFAOYSA-L magnesium;hydrogen sulfate Chemical compound [Mg+2].OS([O-])(=O)=O.OS([O-])(=O)=O FXBYOMANNHFNQV-UHFFFAOYSA-L 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
以上より、本発明の技術的核心となる[反応式1]と[反応式2]について説明したが、以下では、具体的な実施例により本発明を説明することとする。下記5つの実施例は、多様な有機酸と2種のアルコールを出発物質として、各目的に合う化合物を製造することを示しており、製造された物質を適用したさらに他の高付加価値のエステル化合物を製造する方法を示す。
2.20分間撹拌した後、Menthol 20g(天然物から抽出された非精製原料)とNa2SO4 97gを加え、H2SO4 33mLをゆっくり加える。
2.20分間撹拌した後、Na2SO4 83gを加え、H2SO4 28mLをゆっくり加える。
2.20分間撹拌した後、Na2SO4 135gを加え、H2SO4 46mLをゆっくり加える。
2.Na2CO3 23.1gとNaHCO3 1.8gが蒸留水200mLに溶解した水溶液を加え、EA 350mLを加える。
Claims (7)
- 前記エステル化反応は、エチルアセテート(Ethyl Acetate)溶媒をさらに含むことを特徴とする請求項1に記載の塩のイオン交換法を用いたエステル化反応基盤のエステル化合物の製造方法。
- 前記カルボン酸とアルコールは、それぞれラウリン酸とエタノールであることを特徴とする請求項1に記載の塩のイオン交換法を用いたエステル化反応基盤のエステル化合物の製造方法。
- 前記カルボン酸とアルコールは、それぞれ酢酸とメントールであることを特徴とする請求項2に記載の塩のイオン交換法を用いたエステル化反応基盤のエステル化合物の製造方法。
- 前記カルボン酸とアルコールは、それぞれ没食子酸とエタノールであることを特徴とする請求項1に記載の塩のイオン交換法を用いたエステル化反応基盤のエステル化合物の製造方法。
- 前記カルボン酸とアルコールは、それぞれアルギニンとエタノールであることを特徴とする請求項1に記載の塩のイオン交換法を用いたエステル化反応基盤のエステル化合物の製造方法。
- 請求項6に記載の方法により製造された極性エステル化合物であるアルギニンエチルエステル;およびラウロイルクロライド;を処理したアシルァ反応を通して生成されるエチルラウロイルアルギネートハイドロクロライド。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63154643A (ja) * | 1986-12-17 | 1988-06-27 | Daicel Chem Ind Ltd | 低級カルボン酸エステルの製法 |
JP2009222710A (ja) * | 2008-02-19 | 2009-10-01 | Sanyo Chem Ind Ltd | ヘモグロビン安定化剤及びヘモグロビンの安定化方法 |
CN110938020A (zh) * | 2019-10-25 | 2020-03-31 | 浙江圣达生物研究院有限公司 | 一种月桂酰精氨酸乙酯盐酸盐的制备工艺 |
KR20200108764A (ko) * | 2019-03-11 | 2020-09-21 | 고려대학교 산학협력단 | 비천연 아미노산 기반의 항균 항생 방부제의 친환경적 제조방법 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB591421A (en) * | 1945-03-15 | 1947-08-18 | Wolf Ltd Victor | Improvements in treatment and production of esters |
EP0331280A1 (en) * | 1988-01-29 | 1989-09-06 | Pitman-Moore, Inc. | Method for esterifying hindered carboxylic acids |
JPH03223233A (ja) * | 1990-01-26 | 1991-10-02 | Sumikin Chem Co Ltd | ナフタレンカルボン酸エステルの製造方法 |
CA2083346A1 (en) * | 1991-12-13 | 1993-06-14 | Eric G. Lundquist | A catalyzed esterification process |
KR101141856B1 (ko) * | 2005-01-28 | 2012-05-08 | 닛신 오일리오그룹 가부시키가이샤 | 에스테르화 반응 생성물 및 화장료 |
US8278478B2 (en) * | 2009-09-30 | 2012-10-02 | Vishwas Sadhu Ghare | Process for the synthesis of hydrochloride salt of N-fatty acylsubstituted amino acid ethyl esters |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63154643A (ja) * | 1986-12-17 | 1988-06-27 | Daicel Chem Ind Ltd | 低級カルボン酸エステルの製法 |
JP2009222710A (ja) * | 2008-02-19 | 2009-10-01 | Sanyo Chem Ind Ltd | ヘモグロビン安定化剤及びヘモグロビンの安定化方法 |
KR20200108764A (ko) * | 2019-03-11 | 2020-09-21 | 고려대학교 산학협력단 | 비천연 아미노산 기반의 항균 항생 방부제의 친환경적 제조방법 |
CN110938020A (zh) * | 2019-10-25 | 2020-03-31 | 浙江圣达生物研究院有限公司 | 一种月桂酰精氨酸乙酯盐酸盐的制备工艺 |
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