CA1196000A - Process for production of methyl 2- tetradecylglycidate - Google Patents
Process for production of methyl 2- tetradecylglycidateInfo
- Publication number
- CA1196000A CA1196000A CA000443451A CA443451A CA1196000A CA 1196000 A CA1196000 A CA 1196000A CA 000443451 A CA000443451 A CA 000443451A CA 443451 A CA443451 A CA 443451A CA 1196000 A CA1196000 A CA 1196000A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- tetradecylglycidate
- reaction
- formaldehyde
- percent
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- RSSDZUNGAWCFPT-UHFFFAOYSA-N methyl 2-tetradecyloxirane-2-carboxylate Chemical compound CCCCCCCCCCCCCCC1(C(=O)OC)CO1 RSSDZUNGAWCFPT-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 7
- 229920002866 paraformaldehyde Polymers 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- -1 methyl -chloropalmitate Chemical compound 0.000 description 6
- 235000019256 formaldehyde Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007862 dimeric product Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FGIJQXGDQVNWKH-UHFFFAOYSA-N 2-tetradecyloxirane-2-carboxylic acid Chemical compound CCCCCCCCCCCCCCC1(C(O)=O)CO1 FGIJQXGDQVNWKH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XVZPQSMKKWHEPI-UHFFFAOYSA-N O.O.O1C(C1)C(=O)OC(C)CCCCCCCCCCCC Chemical compound O.O.O1C(C1)C(=O)OC(C)CCCCCCCCCCCC XVZPQSMKKWHEPI-UHFFFAOYSA-N 0.000 description 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 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
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006053 organic reaction Methods 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- QZQAQNFAVGKWLG-UHFFFAOYSA-N tetradecyl oxirane-2-carboxylate Chemical compound CCCCCCCCCCCCCCOC(=O)C1CO1 QZQAQNFAVGKWLG-UHFFFAOYSA-N 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 |
|---|---|---|---|
| US459,750 | 1983-01-21 | ||
| US06/459,750 US4499294A (en) | 1983-01-21 | 1983-01-21 | Process for production of methyl 2-tetradecylgycidate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1196000A true CA1196000A (en) | 1985-10-29 |
Family
ID=23826006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000443451A Expired CA1196000A (en) | 1983-01-21 | 1983-12-15 | Process for production of methyl 2- tetradecylglycidate |
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) |
Families Citing this family (4)
| 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 |
| EP1764359A1 (en) * | 2005-09-16 | 2007-03-21 | DSM IP Assets B.V. | Process for the preparation of glycidic ester and an aldehyde |
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
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 |
| EP0115406A1 (en) | 1984-08-08 |
| KR910000239B1 (ko) | 1991-01-23 |
| ATE23156T1 (de) | 1986-11-15 |
| JPS59137478A (ja) | 1984-08-07 |
| EP0115406B1 (en) | 1986-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |