JPS59137478A - メチル−２−テトラデシルグリシデ−トの製法 - Google Patents
メチル−２−テトラデシルグリシデ−トの製法Info
- Publication number
- JPS59137478A JPS59137478A JP59006395A JP639584A JPS59137478A JP S59137478 A JPS59137478 A JP S59137478A JP 59006395 A JP59006395 A JP 59006395A JP 639584 A JP639584 A JP 639584A JP S59137478 A JPS59137478 A JP S59137478A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetradecylglycidate
- reaction
- formaldehyde
- tetradecyl
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- RSSDZUNGAWCFPT-UHFFFAOYSA-N methyl 2-tetradecyloxirane-2-carboxylate Chemical compound CCCCCCCCCCCCCCC1(C(=O)OC)CO1 RSSDZUNGAWCFPT-UHFFFAOYSA-N 0.000 title abstract description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 11
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- -1 decyl glycidate Chemical compound 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 5
- NYTGXUXRZXHXQK-UHFFFAOYSA-N methyl 2-chlorohexadecanoate Chemical compound CCCCCCCCCCCCCCC(Cl)C(=O)OC NYTGXUXRZXHXQK-UHFFFAOYSA-N 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000010 aprotic solvent Substances 0.000 abstract description 2
- 239000003472 antidiabetic agent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LDQUHRSWFMWRNG-UHFFFAOYSA-N 2-chlorohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(Cl)C(O)=O LDQUHRSWFMWRNG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CWORPBBZESDYBS-UHFFFAOYSA-N O.O.[Na].CCCCCCCCCCCCC(C)OC(=O)C1CO1 Chemical compound O.O.[Na].CCCCCCCCCCCCC(C)OC(=O)C1CO1 CWORPBBZESDYBS-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/459,750 US4499294A (en) | 1983-01-21 | 1983-01-21 | Process for production of methyl 2-tetradecylgycidate |
| US459750 | 1983-01-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59137478A true JPS59137478A (ja) | 1984-08-07 |
| JPH0452272B2 JPH0452272B2 (en, 2012) | 1992-08-21 |
Family
ID=23826006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59006395A Granted JPS59137478A (ja) | 1983-01-21 | 1984-01-19 | メチル−２−テトラデシルグリシデ−トの製法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4499294A (en, 2012) |
| EP (1) | EP0115406B1 (en, 2012) |
| JP (1) | JPS59137478A (en, 2012) |
| KR (1) | KR910000239B1 (en, 2012) |
| AT (1) | ATE23156T1 (en, 2012) |
| AU (1) | AU556591B2 (en, 2012) |
| CA (1) | CA1196000A (en, 2012) |
| DE (1) | DE3461089D1 (en, 2012) |
| HU (1) | HU190224B (en, 2012) |
| PH (1) | PH19280A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009512630A (ja) * | 2005-09-16 | 2009-03-26 | ディーエスエム アイピー アセッツ ビー．ブイ． | エポキシ化合物およびアルデヒドの調製方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545672A (en) * | 1993-02-11 | 1996-08-13 | The University Of Texas System | Treatment of insulin resistance and type 2 diabetes mellitus with a thiol protease inhibitor |
| CA2308514A1 (en) * | 2000-05-12 | 2001-11-12 | Mcgill University | Method of hydrogen generation for fuel cell applications and a hydrogen-generating system |
| US7160921B2 (en) * | 2002-01-29 | 2007-01-09 | The Gillette Company | Reduction of hair growth |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2939872A (en) * | 1958-10-29 | 1960-06-07 | Dow Chemical Co | Ethyl 3-(2, 4-dichlorophenyl) glycidate |
| FR1472119A (fr) * | 1965-12-17 | 1967-03-10 | Rhone Poulenc Sa | Procédé de préparation d'époxydes |
| US3933864A (en) * | 1974-12-10 | 1976-01-20 | The Upjohn Company | Process for preparing glycidonitriles |
| US4196300A (en) * | 1975-09-22 | 1980-04-01 | Mcneilabs, Inc. | α-Alkyl-substituted glycidates and thioglycidates |
| GB1551078A (en) * | 1975-09-22 | 1979-08-22 | Mcneilab Inc | Alkyl-substituted glycidates and thioglycidates |
| JPS55153777A (en) * | 1979-05-17 | 1980-11-29 | Nisshin Flour Milling Co Ltd | Improved method of preparation of 3-methyl-3-(substituted phenyl)-glycidic ester |
-
1983
- 1983-01-21 US US06/459,750 patent/US4499294A/en not_active Expired - Lifetime
- 1983-12-15 CA CA000443451A patent/CA1196000A/en not_active Expired
-
1984
- 1984-01-19 JP JP59006395A patent/JPS59137478A/ja active Granted
- 1984-01-20 AT AT84300344T patent/ATE23156T1/de not_active IP Right Cessation
- 1984-01-20 KR KR1019840000243A patent/KR910000239B1/ko not_active Expired
- 1984-01-20 PH PH30138A patent/PH19280A/en unknown
- 1984-01-20 EP EP84300344A patent/EP0115406B1/en not_active Expired
- 1984-01-20 HU HU84249A patent/HU190224B/hu not_active IP Right Cessation
- 1984-01-20 AU AU23669/84A patent/AU556591B2/en not_active Ceased
- 1984-01-20 DE DE8484300344T patent/DE3461089D1/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009512630A (ja) * | 2005-09-16 | 2009-03-26 | ディーエスエム アイピー アセッツ ビー．ブイ． | エポキシ化合物およびアルデヒドの調製方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2366984A (en) | 1984-07-26 |
| DE3461089D1 (en) | 1986-12-04 |
| PH19280A (en) | 1986-03-04 |
| AU556591B2 (en) | 1986-11-13 |
| JPH0452272B2 (en, 2012) | 1992-08-21 |
| KR840007405A (ko) | 1984-12-07 |
| US4499294A (en) | 1985-02-12 |
| HU190224B (en) | 1986-08-28 |
| CA1196000A (en) | 1985-10-29 |
| EP0115406A1 (en) | 1984-08-08 |
| KR910000239B1 (ko) | 1991-01-23 |
| ATE23156T1 (de) | 1986-11-15 |
| EP0115406B1 (en) | 1986-10-29 |
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