DK2451765T3 - Fremgangsmåde til fremstilling af halogenerede precursorer af alkenoner under specifikke betingelser - Google Patents
Fremgangsmåde til fremstilling af halogenerede precursorer af alkenoner under specifikke betingelser Download PDFInfo
- Publication number
- DK2451765T3 DK2451765T3 DK10736998.5T DK10736998T DK2451765T3 DK 2451765 T3 DK2451765 T3 DK 2451765T3 DK 10736998 T DK10736998 T DK 10736998T DK 2451765 T3 DK2451765 T3 DK 2451765T3
- Authority
- DK
- Denmark
- Prior art keywords
- reaction medium
- carboxylic acid
- alkenone
- acid halide
- vinyl ether
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 66
- 239000002243 precursor Substances 0.000 title claims description 58
- 238000002360 preparation method Methods 0.000 title description 5
- 239000012429 reaction media Substances 0.000 claims description 83
- 239000007788 liquid Substances 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 50
- -1 carboxylic acid halide Chemical class 0.000 claims description 49
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 239000012433 hydrogen halide Substances 0.000 claims description 20
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 20
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical group FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229960000834 vinyl ether Drugs 0.000 description 35
- 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 32
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- 238000001149 thermolysis Methods 0.000 description 24
- MPYKDYSKCIRYRA-UHFFFAOYSA-N 4-chloro-4-ethoxy-1,1,1-trifluorobutan-2-one Chemical group CCOC(Cl)CC(=O)C(F)(F)F MPYKDYSKCIRYRA-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- 238000004821 distillation Methods 0.000 description 13
- 230000008030 elimination Effects 0.000 description 13
- 238000003379 elimination reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000002516 radical scavenger Substances 0.000 description 10
- 239000000919 ceramic Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 150000001266 acyl halides Chemical class 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- KURKJXZWCPWPFX-UHFFFAOYSA-N 2,2-difluoroacetyl chloride Chemical group FC(F)C(Cl)=O KURKJXZWCPWPFX-UHFFFAOYSA-N 0.000 description 2
- GGKAAPYKPQEJOK-UHFFFAOYSA-N 3-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCOC(=C)C(=O)C(F)(F)F GGKAAPYKPQEJOK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229960004424 carbon dioxide Drugs 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012528 membrane 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
- 238000003786 synthesis reaction Methods 0.000 description 2
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 1
- DCEPGADSNJKOJK-UHFFFAOYSA-N 2,2,2-trifluoroacetyl fluoride Chemical group FC(=O)C(F)(F)F DCEPGADSNJKOJK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AZPWOLJQERBBBM-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetyl chloride Chemical group FC(F)(Cl)C(Cl)=O AZPWOLJQERBBBM-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- GETLJJKPKIDEIZ-UHFFFAOYSA-N 4,4,4-trifluoro-3-oxobutanoyl fluoride Chemical group FC(=O)CC(=O)C(F)(F)F GETLJJKPKIDEIZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 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
-
- 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
-
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/175—Saturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Fremgangsmåde til fremstilling af en halogeneret precursor af en alkenon, der svarer til formel (I): R1-C(0)-CH2-CH(X)-0R2 (I), hvor X er fluor, chlor eller brom, og RI er en fluoreret Cl-C4-alkylgruppe, eller RI er CF3C(0)CH2, og R2 er aryl, substitueret aryl eller en Cl-C10-alkylgruppe, der eventuelt er substitueret med mindst ét halogenatom, som omfatter reaktion af et carboxylsyrehalid, der svarer til formel (II): R1-C(0)X (II), med en vinylether, der svarer til formel (III): CH2=C(H)-0R2 (III), i fravær eller i det væsentlige fravær af et syrefjernende middel i et væskeformigt reaktionsmedium, og hvor reaktionsmediet er i turbulent tilstand, hvor reaktionen udføres i en kontinuert omrørt tankreaktor, og hvor udtrykket "i det væsentlige" angiver et indhold af syrefjernende middel, der er lig med eller mindre end 1 vægt-% i forhold til den samlede vægt af reaktionsblandingen.
2. Fremgangsmåde ifølge krav 1, hvor RI er en fluoreret Cl-C4-alkylgruppe.
3. Fremgangsmåde ifølge krav 2, hvor RI er en CF3-gruppe.
4. Fremgangsmåde ifølge krav 2 eller 3, hvor R2 er en C1-C4- alkylgruppe, fortrinsvis en methyl- eller ethylgruppe.
5. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 4, hvor carboxylsyrehalidet er trifluoracetylchlorid.
6. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5, hvor vinyletheren og carboxylsyrehalidet tilføres det væskeformige reaktionsmedium via en koncentrisk dyse med et indre tilførselsrør og et ydre tilførselsrør, hvor vinyletheren tilføres via det indre tilførselsrør, og carboxylsyrehalidet tilføres via det ydre tilførselsrør.
7. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 6, hvor fremgangsmåden udføres kontinuert.
8. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 7, hvor den turbulente tilstand er tilstrækkelig til at undgå dannelse af "hot spots".
9. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 8, hvor det væskeformige reaktionsmedium indeholder fra 1 vægt-%, fortrinsvis fra 5 vægt-% til mindre end 20 vægt-% carboxylsyrehalid.
10. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 9, hvor vinyletheren tilføres det væskeformige reaktionsmedium ved en hastighed fra 0,01 til 2 mol/time/mol carboxylsyrehalid.
11. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 10, hvor reaktionen udføres ved en temperatur fra 0 °C til 40 °C.
12. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 11, der yderligere omfatter udtagning af mindst en del af det væskeformige reaktionsmedium og yderligere reaktion af delen i en stempelstrømningsreaktor.
13. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 12, hvor mindst en del af carboxylsyrehalidet tilføres reaktionsmediet i en væskeformig tilstand.
14. Fremgangsmåde til fremstilling af en alkenon, der omfatter (a) reaktion af et carboxylsyrehalid med en vinylether til frembringelse af en halogeneret precursor af alkenonen ifølge et hvilket som helst af kravene 1 til 13 og (b) fjernelse af hydrogenhalid fra precursoren til frembringelse af alkenonen.
15. Fremgangsmåde ifølge krav 5, hvor trifluoracetylchlorid tilføres reaktionsmediet i væskeform.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2009/058525 WO2010000871A2 (en) | 2008-07-04 | 2009-07-06 | Process for the manufacture of alkenones |
| EP10150229 | 2010-01-07 | ||
| PCT/EP2010/059549 WO2011003856A1 (en) | 2009-07-06 | 2010-07-05 | Process for the manufacture of halogenated precursors of alkenones under specific conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2451765T3 true DK2451765T3 (da) | 2017-04-03 |
Family
ID=42236932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10736998.5T DK2451765T3 (da) | 2009-07-06 | 2010-07-05 | Fremgangsmåde til fremstilling af halogenerede precursorer af alkenoner under specifikke betingelser |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8552221B2 (da) |
| EP (1) | EP2451765B1 (da) |
| JP (1) | JP2012532182A (da) |
| KR (1) | KR20120038997A (da) |
| CN (1) | CN102471201A (da) |
| AU (1) | AU2010270359A1 (da) |
| BR (1) | BR112012000279A2 (da) |
| CA (1) | CA2765487A1 (da) |
| DK (1) | DK2451765T3 (da) |
| ES (1) | ES2620405T3 (da) |
| IL (1) | IL216941A0 (da) |
| MX (1) | MX2012000381A (da) |
| PT (1) | PT2451765T (da) |
| WO (1) | WO2011003856A1 (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2181087B1 (en) | 2007-08-16 | 2015-10-14 | Solvay Sa | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
| 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 |
| JP5939980B2 (ja) | 2009-07-06 | 2016-06-29 | ソルヴェイ（ソシエテ アノニム） | 溶媒の存在下でのアルケノンのハロゲン化前駆体の製造方法 |
| EP2607343A1 (en) * | 2011-12-22 | 2013-06-26 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones and of alkenones |
| DK2888219T3 (da) * | 2012-08-22 | 2019-05-13 | Solvay | Fremgangsmåde til fremstilling af alkenoner |
| JP2014162751A (ja) * | 2013-02-25 | 2014-09-08 | Dic Corp | 化合物、液晶組成物、及び表示装置 |
| WO2015004035A1 (en) * | 2013-07-09 | 2015-01-15 | Lonza Ltd | Method for preparation of 4-alkoxy-1,1,1-trifluorobut-3-en-2-ones from trifluoroacetylacetic acid |
| MX2016017019A (es) | 2014-06-26 | 2017-05-12 | Lonza Ag | Metodo para la preparacion de 4-alcoxi-1,1,1-trifluorobut-3-en-2-o nas de 1,1,1 trifluoroacetona. |
| CN110526810A (zh) * | 2018-05-25 | 2019-12-03 | 浙江蓝天环保高科技股份有限公司 | 一种1,1,1-三氟-4-乙氧基戊-3-烯-2-酮的制备方法 |
| CN109438237B (zh) * | 2018-12-12 | 2021-05-28 | 浙江华方药业股份有限公司 | 一种3-乙氧基丙烯酸乙酯的制备方法 |
Family Cites Families (12)
| 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 |
| DE19711020A1 (de) | 1997-03-17 | 1998-09-24 | Basf Ag | Polymerisationsreaktor |
| FR2796311B1 (fr) | 1999-07-16 | 2001-09-14 | Atofina | Reacteur multietage, ses applications et procede de fabrication du peroxyde d'hydrogene |
| WO2003066558A2 (de) | 2002-02-08 | 2003-08-14 | Solvay Fluor Und Derivate Gmbh | Herstellung von alkenonen |
| KR20020070914A (ko) | 2002-07-29 | 2002-09-11 | 배은우 | 색표와 추를 이용한 색채선별방법 및 그 방법을 이용한색채치료 보조기구 |
| DE10325715A1 (de) * | 2003-06-06 | 2004-12-23 | Solvay Fluor Und Derivate Gmbh | Vereinfachte Herstellung von Alkenonen |
| DE102007029506B4 (de) | 2007-06-25 | 2009-04-02 | Heraeus Quarzglas Gmbh & Co. Kg | Verfahren zur Herstellung eines Zylinders aus Quarzglas unter Einsatz einer Haltevorrichtung sowie geeignete Haltevorrichtung zur Durchführung des Verfahrens |
| WO2009006217A1 (en) * | 2007-06-29 | 2009-01-08 | 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 |
| WO2010003768A1 (de) | 2008-06-16 | 2010-01-14 | Rhein Chemie Rheinau Gmbh | Protonenleitfähigkeitverleihendes material |
| CH699078A1 (de) | 2008-07-02 | 2010-01-15 | Kistler Holding Ag | Zündkerze im Grundaufbau mit Drucksensor. |
| CA2735679C (en) | 2009-06-29 | 2016-08-23 | Tts Tooltechnic Systems Ag & Co. Kg | Stackable container assembly with reciprocal locking of the stacked containers |
| US8459495B2 (en) | 2009-06-29 | 2013-06-11 | Tts Tooltechnic Systems Ag & Co. Kg | Portable container |
-
2010
- 2010-07-05 DK DK10736998.5T patent/DK2451765T3/da active
- 2010-07-05 PT PT107369985T patent/PT2451765T/pt unknown
- 2010-07-05 AU AU2010270359A patent/AU2010270359A1/en not_active Abandoned
- 2010-07-05 CA CA2765487A patent/CA2765487A1/en not_active Abandoned
- 2010-07-05 WO PCT/EP2010/059549 patent/WO2011003856A1/en active Application Filing
- 2010-07-05 MX MX2012000381A patent/MX2012000381A/es unknown
- 2010-07-05 KR KR1020127003110A patent/KR20120038997A/ko not_active Application Discontinuation
- 2010-07-05 US US12/999,730 patent/US8552221B2/en not_active Expired - Fee Related
- 2010-07-05 EP EP10736998.5A patent/EP2451765B1/en not_active Not-in-force
- 2010-07-05 CN CN2010800301348A patent/CN102471201A/zh active Pending
- 2010-07-05 ES ES10736998.5T patent/ES2620405T3/es active Active
- 2010-07-05 JP JP2012518942A patent/JP2012532182A/ja active Pending
- 2010-07-05 BR BR112012000279A patent/BR112012000279A2/pt not_active IP Right Cessation
-
2011
- 2011-12-13 IL IL216941A patent/IL216941A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2620405T3 (es) | 2017-06-28 |
| EP2451765A1 (en) | 2012-05-16 |
| IL216941A0 (en) | 2012-02-29 |
| AU2010270359A1 (en) | 2012-02-02 |
| BR112012000279A2 (pt) | 2016-02-23 |
| EP2451765B1 (en) | 2016-12-28 |
| KR20120038997A (ko) | 2012-04-24 |
| CN102471201A (zh) | 2012-05-23 |
| PT2451765T (pt) | 2017-04-03 |
| JP2012532182A (ja) | 2012-12-13 |
| WO2011003856A1 (en) | 2011-01-13 |
| MX2012000381A (es) | 2012-03-07 |
| US20120101305A1 (en) | 2012-04-26 |
| US8552221B2 (en) | 2013-10-08 |
| CA2765487A1 (en) | 2011-01-13 |
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