JP4921964B2 - アルケノンの簡略化した製法 - Google Patents
アルケノンの簡略化した製法 Download PDFInfo
- Publication number
- JP4921964B2 JP4921964B2 JP2006508186A JP2006508186A JP4921964B2 JP 4921964 B2 JP4921964 B2 JP 4921964B2 JP 2006508186 A JP2006508186 A JP 2006508186A JP 2006508186 A JP2006508186 A JP 2006508186A JP 4921964 B2 JP4921964 B2 JP 4921964B2
- Authority
- JP
- Japan
- Prior art keywords
- alkenone
- reaction
- process according
- carried out
- vinyl ether
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000003381 stabilizer Substances 0.000 claims abstract description 17
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 8
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 8
- -1 carboxylic acid halide Chemical class 0.000 claims abstract description 4
- 230000008030 elimination Effects 0.000 claims abstract description 4
- 238000003379 elimination reaction Methods 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 26
- 239000002516 radical scavenger Substances 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 abstract description 3
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002989 phenols Chemical group 0.000 description 3
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 3
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000007858 starting material 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
- 238000011282 treatment Methods 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- YKYIFUROKBDHCY-UHFFFAOYSA-N 4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCOC=CC(=O)C(F)(F)F YKYIFUROKBDHCY-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10325715.2 | 2003-06-06 | ||
| DE10325715A DE10325715A1 (de) | 2003-06-06 | 2003-06-06 | Vereinfachte Herstellung von Alkenonen |
| PCT/EP2004/005466 WO2004108647A2 (de) | 2003-06-06 | 2004-05-21 | Verfahren zur herstellung von alkenonethern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006527170A JP2006527170A (ja) | 2006-11-30 |
| JP2006527170A5 JP2006527170A5 (enExample) | 2007-06-07 |
| JP4921964B2 true JP4921964B2 (ja) | 2012-04-25 |
Family
ID=33482641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006508186A Expired - Fee Related JP4921964B2 (ja) | 2003-06-06 | 2004-05-21 | アルケノンの簡略化した製法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7405328B2 (enExample) |
| EP (1) | EP1644306B2 (enExample) |
| JP (1) | JP4921964B2 (enExample) |
| CN (1) | CN100471830C (enExample) |
| AT (1) | ATE518821T1 (enExample) |
| DE (1) | DE10325715A1 (enExample) |
| DK (1) | DK1644306T3 (enExample) |
| ES (1) | ES2370173T3 (enExample) |
| PL (1) | PL1644306T3 (enExample) |
| PT (1) | PT1644306E (enExample) |
| WO (1) | WO2004108647A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008270648B2 (en) * | 2007-06-29 | 2013-08-22 | Corteva Agriscience Llc | 4-Chloro-4-alkoxy-1,1,1-trifluoro-2-butanones, their preparation and their use in preparing 4-alkoxy-1,1,1-trifluoro-3-buten-2-ones |
| CN101801906A (zh) | 2007-08-16 | 2010-08-11 | 索尔维公司 | 制备4-氟取代的3-氧代-烷酸酯的方法 |
| DK2315750T3 (da) * | 2008-07-01 | 2013-02-18 | Dow Agrosciences Llc | Forbedret fremgangsmåde til fremstilling af 2-trifluormethyl-5-(1-substituerede) alkylpyridiner |
| US8519195B2 (en) | 2008-07-04 | 2013-08-27 | Solvay Sa | Process for the manufacture of alkenones |
| CA2735921C (en) * | 2008-09-30 | 2017-03-21 | Solvay Sa | Process for the synthesis of halogenated cyclic compounds |
| GB0903749D0 (en) * | 2009-03-04 | 2009-04-15 | Syngenta Participations Ag | Chemical process |
| DK2451764T3 (en) * | 2009-07-06 | 2016-03-29 | Solvay | Method for producing alkenoner |
| WO2011003854A1 (en) | 2009-07-06 | 2011-01-13 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones in the presence of a solvent |
| US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
| BR112012000279A2 (pt) * | 2009-07-06 | 2016-02-23 | Solvay | processos para preparar e para fabricar um precursor halogenado de uma alquenona, e para preparar uma alquenona |
| WO2012025548A1 (en) | 2010-08-27 | 2012-03-01 | Solvay Sa | Process for the preparation of alkenones |
| EP2607343A1 (en) * | 2011-12-22 | 2013-06-26 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones and of alkenones |
| EP2888219B1 (en) | 2012-08-22 | 2019-02-06 | Solvay Sa | Process for the manufacture of alkenones |
| WO2015011728A1 (en) | 2013-07-26 | 2015-01-29 | Srf Limited | Method for producing alkenone ethers |
| WO2016079122A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | A method for producing a chemical compound and apparatus therefor |
| KR20180108695A (ko) | 2016-01-28 | 2018-10-04 | 솔베이(소시에떼아노님) | 할로겐 치환된 디케톤, 피라졸 화합물 및 피라졸 화합물의 제조 방법 |
| EP3199522A1 (en) | 2016-02-01 | 2017-08-02 | Solvay SA | Aminothioate derivatives, production thereof and use |
| EP3246313A1 (en) | 2016-05-19 | 2017-11-22 | Solvay Sa | Process for the manufacture of 2-substituted-5-(1-methylthio)alkylpyridines |
| EP3679007A1 (en) | 2017-09-04 | 2020-07-15 | Solvay SA | Process and intermediate for the manufacture of difluoroacetyl chloride |
| EP3605699A1 (en) | 2018-07-31 | 2020-02-05 | Solvay Sa | New components for electrolyte compositions |
| EP3605698A1 (en) | 2018-07-31 | 2020-02-05 | Solvay Sa | New components for electrolyte compositions |
| WO2020025499A1 (en) | 2018-07-31 | 2020-02-06 | Solvay Sa | New components for electrolyte compositions |
| EP3605700A1 (en) | 2018-07-31 | 2020-02-05 | Solvay Sa | New components for electrolyte compositions |
| EP3632855A1 (en) | 2018-10-02 | 2020-04-08 | Solvay Sa | A method for providing aqueous compositions with reduced content of organic fluorinated compounds |
| CN112979443A (zh) * | 2019-12-13 | 2021-06-18 | 浙江蓝天环保高科技股份有限公司 | 一种三氟甲基丁烯酮类衍生物的连续制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09132554A (ja) * | 1995-08-08 | 1997-05-20 | Ishihara Sangyo Kaisha Ltd | ４−アルコキシ−１，１，１−トリフルオロ−３−ブテン−２−オンの製造方法 |
| JP2002201161A (ja) * | 2000-10-23 | 2002-07-16 | Nippon Shokubai Co Ltd | ビニルエーテル基含有（メタ）アクリル酸エステル組成物及びその製造方法 |
| WO2003006407A1 (en) * | 2001-07-13 | 2003-01-23 | Kyowa Yuka Co., Ltd. | Process for producing ether compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2332037T3 (es) | 1995-05-26 | 2010-01-25 | Ishihara Sangyo Kaisha, Ltd. | Procedimiento para la produccion de 1,1,1-trifluoro-3-buten-2-ona sustituidos. |
-
2003
- 2003-06-06 DE DE10325715A patent/DE10325715A1/de not_active Withdrawn
-
2004
- 2004-05-21 ES ES04739287T patent/ES2370173T3/es not_active Expired - Lifetime
- 2004-05-21 AT AT04739287T patent/ATE518821T1/de active
- 2004-05-21 JP JP2006508186A patent/JP4921964B2/ja not_active Expired - Fee Related
- 2004-05-21 PT PT04739287T patent/PT1644306E/pt unknown
- 2004-05-21 DK DK04739287.3T patent/DK1644306T3/da active
- 2004-05-21 WO PCT/EP2004/005466 patent/WO2004108647A2/de not_active Ceased
- 2004-05-21 PL PL04739287T patent/PL1644306T3/pl unknown
- 2004-05-21 EP EP04739287.3A patent/EP1644306B2/de not_active Expired - Lifetime
- 2004-05-21 CN CNB2004800157163A patent/CN100471830C/zh not_active Expired - Lifetime
-
2005
- 2005-12-06 US US11/294,371 patent/US7405328B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09132554A (ja) * | 1995-08-08 | 1997-05-20 | Ishihara Sangyo Kaisha Ltd | ４−アルコキシ−１，１，１−トリフルオロ−３−ブテン−２−オンの製造方法 |
| JP2002201161A (ja) * | 2000-10-23 | 2002-07-16 | Nippon Shokubai Co Ltd | ビニルエーテル基含有（メタ）アクリル酸エステル組成物及びその製造方法 |
| WO2003006407A1 (en) * | 2001-07-13 | 2003-01-23 | Kyowa Yuka Co., Ltd. | Process for producing ether compound |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1644306A2 (de) | 2006-04-12 |
| JP2006527170A (ja) | 2006-11-30 |
| EP1644306B2 (de) | 2019-12-25 |
| PT1644306E (pt) | 2011-10-19 |
| CN1832911A (zh) | 2006-09-13 |
| PL1644306T3 (pl) | 2011-12-30 |
| US7405328B2 (en) | 2008-07-29 |
| DK1644306T3 (da) | 2011-11-21 |
| CN100471830C (zh) | 2009-03-25 |
| DE10325715A1 (de) | 2004-12-23 |
| EP1644306B1 (de) | 2011-08-03 |
| WO2004108647A2 (de) | 2004-12-16 |
| WO2004108647A3 (de) | 2005-02-24 |
| ATE518821T1 (de) | 2011-08-15 |
| US20060084813A1 (en) | 2006-04-20 |
| ES2370173T3 (es) | 2011-12-13 |
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