DE10325715A1 - Vereinfachte Herstellung von Alkenonen - Google Patents
Vereinfachte Herstellung von Alkenonen Download PDFInfo
- Publication number
- DE10325715A1 DE10325715A1 DE10325715A DE10325715A DE10325715A1 DE 10325715 A1 DE10325715 A1 DE 10325715A1 DE 10325715 A DE10325715 A DE 10325715A DE 10325715 A DE10325715 A DE 10325715A DE 10325715 A1 DE10325715 A1 DE 10325715A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- propyl
- alkenone
- alkyl group
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000003381 stabilizer Substances 0.000 claims abstract description 16
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 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 3
- 239000002253 acid Substances 0.000 claims description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 239000002516 radical scavenger Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 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 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 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
- 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 description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 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
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 230000007017 scission Effects 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 230000008030 elimination Effects 0.000 abstract description 3
- 238000003379 elimination reaction Methods 0.000 abstract description 3
- 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 9
- 239000002904 solvent Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000002989 phenols Chemical group 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 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 description 3
- 239000000460 chlorine Substances 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
- 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 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
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 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
- 238000001149 thermolysis Methods 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010626 work up procedure 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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10325715A DE10325715A1 (de) | 2003-06-06 | 2003-06-06 | Vereinfachte Herstellung von Alkenonen |
| PL04739287T PL1644306T3 (pl) | 2003-06-06 | 2004-05-21 | Sposób produkcji alkenonoeterów |
| JP2006508186A JP4921964B2 (ja) | 2003-06-06 | 2004-05-21 | アルケノンの簡略化した製法 |
| CNB2004800157163A CN100471830C (zh) | 2003-06-06 | 2004-05-21 | 烯酮醚的制备方法 |
| EP04739287.3A EP1644306B2 (de) | 2003-06-06 | 2004-05-21 | Verfahren zur herstellung von alkenonethern |
| PT04739287T PT1644306E (pt) | 2003-06-06 | 2004-05-21 | Preparação simplificada de alcenonas |
| DK04739287.3T DK1644306T3 (da) | 2003-06-06 | 2004-05-21 | Fremgangsmåde til fremstilling af alkenonethere |
| PCT/EP2004/005466 WO2004108647A2 (de) | 2003-06-06 | 2004-05-21 | Verfahren zur herstellung von alkenonethern |
| ES04739287T ES2370173T3 (es) | 2003-06-06 | 2004-05-21 | Procedimiento para la preparación de alquenonas. |
| AT04739287T ATE518821T1 (de) | 2003-06-06 | 2004-05-21 | Verfahren zur herstellung von alkenonethern |
| US11/294,371 US7405328B2 (en) | 2003-06-06 | 2005-12-06 | Method for producing alkenone ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10325715A DE10325715A1 (de) | 2003-06-06 | 2003-06-06 | Vereinfachte Herstellung von Alkenonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10325715A1 true DE10325715A1 (de) | 2004-12-23 |
Family
ID=33482641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10325715A Withdrawn DE10325715A1 (de) | 2003-06-06 | 2003-06-06 | Vereinfachte Herstellung von Alkenonen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7405328B2 (https=) |
| EP (1) | EP1644306B2 (https=) |
| JP (1) | JP4921964B2 (https=) |
| CN (1) | CN100471830C (https=) |
| AT (1) | ATE518821T1 (https=) |
| DE (1) | DE10325715A1 (https=) |
| DK (1) | DK1644306T3 (https=) |
| ES (1) | ES2370173T3 (https=) |
| PL (1) | PL1644306T3 (https=) |
| PT (1) | PT1644306E (https=) |
| WO (1) | WO2004108647A2 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2928232C (en) * | 2007-06-29 | 2018-01-16 | Dow Agrosciences 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 |
| WO2009021987A1 (en) | 2007-08-16 | 2009-02-19 | Solvay (Société Anonyme) | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
| MX2011000196A (es) * | 2008-07-01 | 2011-03-24 | Dow Agrosciences Llc | Proceso mejorado para la preparacion de alquilpiridinas 2-trifluorometil-5-(1-sustituidas). |
| KR101652539B1 (ko) * | 2008-07-04 | 2016-08-30 | 솔베이(소시에떼아노님) | 알케논의 제조 방법 |
| CN106083710B (zh) * | 2008-09-30 | 2021-03-12 | 索尔维公司 | 用于合成卤化的环状化合物的方法 |
| GB0903749D0 (en) * | 2009-03-04 | 2009-04-15 | Syngenta Participations Ag | Chemical process |
| CA2765487A1 (en) | 2009-07-06 | 2011-01-13 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones under specific conditions |
| US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
| ES2537676T3 (es) | 2009-07-06 | 2015-06-10 | Solvay Sa | Proceso para la fabricación de precursores halogenados de alquenonas en presencia de un disolvente |
| WO2011003860A1 (en) * | 2009-07-06 | 2011-01-13 | Solvay Sa | Process for the manufacture of alkenones |
| 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 |
| IN2015DN00635A (https=) * | 2012-08-22 | 2015-06-26 | Solvay | |
| 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 |
| US10829456B2 (en) | 2016-01-28 | 2020-11-10 | Solvay Sa | Halogen substituted diketones, pyrazole compounds and processes for the manufacture of pyrazole compounds |
| 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 |
| WO2019043238A1 (en) | 2017-09-04 | 2019-03-07 | Solvay Sa | PROCESS AND INTERMEDIARY FOR MANUFACTURING DIFLUOROACETYL CHLORIDE |
| 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 |
| EP3605699A1 (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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0744400B1 (en) | 1995-05-26 | 2002-09-11 | Ishihara Sangyo Kaisha, Ltd. | Process for producing 4-trifluoromethylnicotinic acid |
| JP3843152B2 (ja) * | 1995-08-08 | 2006-11-08 | 石原産業株式会社 | 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 |
| JP3463876B2 (ja) * | 2000-10-23 | 2003-11-05 | 株式会社日本触媒 | 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 |
| KR100894244B1 (ko) * | 2001-07-13 | 2009-04-20 | 교와 핫꼬 케미칼 가부시키가이샤 | 에테르 화합물의 제조법 |
-
2003
- 2003-06-06 DE DE10325715A patent/DE10325715A1/de not_active Withdrawn
-
2004
- 2004-05-21 AT AT04739287T patent/ATE518821T1/de 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 CN CNB2004800157163A patent/CN100471830C/zh not_active Expired - Lifetime
- 2004-05-21 JP JP2006508186A patent/JP4921964B2/ja not_active Expired - Fee Related
- 2004-05-21 ES ES04739287T patent/ES2370173T3/es not_active Expired - Lifetime
- 2004-05-21 PT PT04739287T patent/PT1644306E/pt unknown
- 2004-05-21 EP EP04739287.3A patent/EP1644306B2/de not_active Expired - Lifetime
- 2004-05-21 DK DK04739287.3T patent/DK1644306T3/da active
-
2005
- 2005-12-06 US US11/294,371 patent/US7405328B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1832911A (zh) | 2006-09-13 |
| PT1644306E (pt) | 2011-10-19 |
| DK1644306T3 (da) | 2011-11-21 |
| US7405328B2 (en) | 2008-07-29 |
| EP1644306A2 (de) | 2006-04-12 |
| PL1644306T3 (pl) | 2011-12-30 |
| US20060084813A1 (en) | 2006-04-20 |
| WO2004108647A3 (de) | 2005-02-24 |
| WO2004108647A2 (de) | 2004-12-16 |
| EP1644306B2 (de) | 2019-12-25 |
| ES2370173T3 (es) | 2011-12-13 |
| CN100471830C (zh) | 2009-03-25 |
| ATE518821T1 (de) | 2011-08-15 |
| JP4921964B2 (ja) | 2012-04-25 |
| EP1644306B1 (de) | 2011-08-03 |
| JP2006527170A (ja) | 2006-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: SOLVAY FLUOR GMBH, 30173 HANNOVER, DE |
|
| 8139 | Disposal/non-payment of the annual fee |