SK282381B6 - Spôsob výroby čistých alkylesterov kyseliny alkylacetoctovej - Google Patents
Spôsob výroby čistých alkylesterov kyseliny alkylacetoctovej Download PDFInfo
- Publication number
- SK282381B6 SK282381B6 SK286-97A SK28697A SK282381B6 SK 282381 B6 SK282381 B6 SK 282381B6 SK 28697 A SK28697 A SK 28697A SK 282381 B6 SK282381 B6 SK 282381B6
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- ester
- formula
- acetic acid
- methyl
- Prior art date
Links
- 125000005907 alkyl ester group Chemical group 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 239000006227 byproduct Substances 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- -1 alkyl acetic acid Chemical compound 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000012535 impurity Substances 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- HAGXFSMJELVHFJ-UHFFFAOYSA-N methyl oct-3-enoate Chemical compound CCCCC=CCC(=O)OC HAGXFSMJELVHFJ-UHFFFAOYSA-N 0.000 description 5
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012455 biphasic mixture Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- AHLBNYSZXLDEJQ-UHFFFAOYSA-N N-formyl-L-leucylester Natural products CCCCCCCCCCCC(OC(=O)C(CC(C)C)NC=O)CC1OC(=O)C1CCCCCC AHLBNYSZXLDEJQ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JATSQKRPKKYPHB-UHFFFAOYSA-N methyl 2-acetylhex-3-enoate Chemical compound CCC=CC(C(C)=O)C(=O)OC JATSQKRPKKYPHB-UHFFFAOYSA-N 0.000 description 1
- PYYFKCZKDCTZBH-UHFFFAOYSA-N methyl 2-acetylhexanoate Chemical compound CCCCC(C(C)=O)C(=O)OC PYYFKCZKDCTZBH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229960001243 orlistat Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH65596 | 1996-03-13 | ||
| CH108796 | 1996-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK28697A3 SK28697A3 (en) | 1997-12-10 |
| SK282381B6 true SK282381B6 (sk) | 2002-01-07 |
Family
ID=25685276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK286-97A SK282381B6 (sk) | 1996-03-13 | 1997-03-05 | Spôsob výroby čistých alkylesterov kyseliny alkylacetoctovej |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5786501A (zh) |
| EP (1) | EP0795538B1 (zh) |
| JP (1) | JP3981998B2 (zh) |
| KR (1) | KR100465142B1 (zh) |
| CN (1) | CN1116272C (zh) |
| AT (1) | ATE184588T1 (zh) |
| CA (1) | CA2198837C (zh) |
| CZ (1) | CZ293618B6 (zh) |
| DE (1) | DE59700429D1 (zh) |
| DK (1) | DK0795538T3 (zh) |
| ES (1) | ES2138409T3 (zh) |
| HU (1) | HU216549B (zh) |
| NO (1) | NO307044B1 (zh) |
| PL (1) | PL187309B1 (zh) |
| SK (1) | SK282381B6 (zh) |
| TW (1) | TW349938B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT407249B (de) * | 1997-12-29 | 2001-01-25 | Chemie Linz Gmbh | Verbessertes verfahren zur herstellung von 2-acetylcarbonsäureestern |
| CN114920646B (zh) * | 2022-05-13 | 2023-10-27 | 安徽英瑞骐生物科技有限公司 | 一种2-正丁基乙酰乙酸乙酯的新合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2900311A (en) * | 1952-10-11 | 1959-08-18 | Union Carbide Corp | Purification of acetoacetic esters by distillation |
| US2843623A (en) * | 1954-10-01 | 1958-07-15 | Nat Distillers Chem Corp | Production of ethyl acetoacetate |
| BE760034A (fr) * | 1969-12-08 | 1971-06-08 | Ici Ltd | Production d'esters |
| DE3227388A1 (de) * | 1982-07-22 | 1984-01-26 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (alpha)-substituierten ss-dicarbonyl-, ss-cyancarbonyl- und ss-dicyanverbindungen |
-
1997
- 1997-02-25 US US08/806,051 patent/US5786501A/en not_active Expired - Fee Related
- 1997-02-28 CA CA002198837A patent/CA2198837C/en not_active Expired - Fee Related
- 1997-03-04 TW TW086102538A patent/TW349938B/zh active
- 1997-03-05 SK SK286-97A patent/SK282381B6/sk not_active IP Right Cessation
- 1997-03-07 KR KR1019970007701A patent/KR100465142B1/ko not_active IP Right Cessation
- 1997-03-07 JP JP05297197A patent/JP3981998B2/ja not_active Expired - Lifetime
- 1997-03-12 NO NO971148A patent/NO307044B1/no not_active IP Right Cessation
- 1997-03-12 ES ES97104180T patent/ES2138409T3/es not_active Expired - Lifetime
- 1997-03-12 AT AT97104180T patent/ATE184588T1/de not_active IP Right Cessation
- 1997-03-12 HU HU9700580A patent/HU216549B/hu not_active IP Right Cessation
- 1997-03-12 DK DK97104180T patent/DK0795538T3/da active
- 1997-03-12 EP EP97104180A patent/EP0795538B1/de not_active Expired - Lifetime
- 1997-03-12 DE DE59700429T patent/DE59700429D1/de not_active Expired - Fee Related
- 1997-03-12 CZ CZ1997748A patent/CZ293618B6/cs not_active IP Right Cessation
- 1997-03-12 PL PL97318927A patent/PL187309B1/pl not_active IP Right Cessation
- 1997-03-13 CN CN97103475A patent/CN1116272C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SK28697A3 (en) | 1997-12-10 |
| CA2198837C (en) | 2004-10-26 |
| HUP9700580A3 (en) | 1998-01-28 |
| CN1116272C (zh) | 2003-07-30 |
| CA2198837A1 (en) | 1997-09-14 |
| ATE184588T1 (de) | 1999-10-15 |
| US5786501A (en) | 1998-07-28 |
| CZ293618B6 (cs) | 2004-06-16 |
| DK0795538T3 (da) | 1999-12-20 |
| PL187309B1 (pl) | 2004-06-30 |
| NO971148L (no) | 1997-09-15 |
| NO307044B1 (no) | 2000-01-31 |
| HU216549B (hu) | 1999-07-28 |
| NO971148D0 (no) | 1997-03-12 |
| DE59700429D1 (de) | 1999-10-21 |
| HU9700580D0 (en) | 1997-04-28 |
| EP0795538B1 (de) | 1999-09-15 |
| KR100465142B1 (ko) | 2005-04-06 |
| PL318927A1 (en) | 1997-09-15 |
| HUP9700580A2 (en) | 1997-12-29 |
| ES2138409T3 (es) | 2000-01-01 |
| TW349938B (en) | 1999-01-11 |
| EP0795538A1 (de) | 1997-09-17 |
| CN1163260A (zh) | 1997-10-29 |
| CZ74897A3 (cs) | 1998-05-13 |
| JP3981998B2 (ja) | 2007-09-26 |
| JPH101456A (ja) | 1998-01-06 |
| KR970069972A (ko) | 1997-11-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3860234B2 (ja) | メタクリル酸エステルの高収率製造方法 | |
| IL207408A (en) | Process for Preparation of Alkyl-2-Methyl Alkoxy-4,4-Dipluoro-3-Oxo Butyrate | |
| CA2030107A1 (en) | Process for the production of 1-(aminomethyl)cyclohexane acetic acid | |
| US4740613A (en) | Preparation of 4-pentenoates | |
| SK282381B6 (sk) | Spôsob výroby čistých alkylesterov kyseliny alkylacetoctovej | |
| EP0346852B1 (de) | Verfahren zur Herstellung von 4-chlor-3-alkoxy-but-2E-en-säurealkylester | |
| EP0051233B1 (de) | Verfahren zur Herstellung von 13-Oxabicyclo(10.3.0)-pentadecan | |
| CA2339997C (en) | Method for producing atropic acid ethyl ester | |
| CN109824605B (zh) | 瑞舒伐他汀钙的合成方法 | |
| JP3396097B2 (ja) | ４−イソプロピルシクロヘキサンカルボン酸エステル誘導体の製法 | |
| JPH11322665A (ja) | 光学活性α−トリフルオロメチル乳酸の精製方法 | |
| RU2058281C1 (ru) | Способ рацемизации нерацемической 3-оксоциклопентан-или-гексанкарбоновой кислоты или ее сложного эфира с низшим алифатическим спиртом | |
| US5436365A (en) | Process for the preparation of pimelic esters | |
| EP0389876B1 (en) | New process for the synthesis of the n-methyl-3,4-dimethoxyphenylethylamine | |
| KR100529703B1 (ko) | 키랄 중간체의 제조방법 및 그를 이용한 아토바스타틴의제조방법 | |
| JP4071633B2 (ja) | アルキルベンゾイルアクリレートの製造方法 | |
| US6143920A (en) | Process for the preparation of methoxyacetic acid esters | |
| US5118834A (en) | Process for the preparation of butyl 2-phenylcyclopropanecarboxylates | |
| WO2005023768A1 (en) | An improved process for the preparation of pure nisoldipine | |
| SK104698A3 (en) | Method for the preparation of 1-pyruvyl-l-proline | |
| JPH1095760A (ja) | シアノ酢酸エステルの製造法 | |
| JPH11240869A (ja) | ラクタムカルボン酸誘導体およびその製法、ならびにそれを用いたピペリジン誘導体の製法 | |
| JP2001048833A (ja) | マロン酸モノアルキルエステルのアルカリ金属塩の製造法 | |
| US20010021787A1 (en) | Process for preparing cyanoacetamide | |
| JP2003246762A (ja) | シクロペンテノロン類の精製方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20100305 |