JP4828701B2 - 選択的水素化脱ハロゲン化方法 - Google Patents
選択的水素化脱ハロゲン化方法 Download PDFInfo
- Publication number
- JP4828701B2 JP4828701B2 JP2000588098A JP2000588098A JP4828701B2 JP 4828701 B2 JP4828701 B2 JP 4828701B2 JP 2000588098 A JP2000588098 A JP 2000588098A JP 2000588098 A JP2000588098 A JP 2000588098A JP 4828701 B2 JP4828701 B2 JP 4828701B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- fluorine
- acid
- metal
- aqueous phase
- 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
- 238000000034 method Methods 0.000 title claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000000758 substrate Substances 0.000 claims abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000008346 aqueous phase Substances 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 239000012071 phase Substances 0.000 claims abstract description 8
- 239000007789 gas Substances 0.000 claims abstract description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical group 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 238000005695 dehalogenation reaction Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 abstract description 30
- 229910052799 carbon Inorganic materials 0.000 abstract description 22
- 239000011737 fluorine Substances 0.000 abstract description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 21
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 13
- 239000003054 catalyst Substances 0.000 abstract description 6
- 150000002431 hydrogen Chemical class 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000009396 hybridization Methods 0.000 abstract 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 24
- 125000000524 functional group Chemical group 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 150000001787 chalcogens Chemical group 0.000 description 3
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- -1 perfluoro compound Chemical class 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- PFYAMVWLZDZJOQ-UHFFFAOYSA-M sodium;2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)F PFYAMVWLZDZJOQ-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 235000011162 ammonium carbonates Nutrition 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical group OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- DPYMFVXJLLWWEU-UHFFFAOYSA-N desflurane Chemical compound FC(F)OC(F)C(F)(F)F DPYMFVXJLLWWEU-UHFFFAOYSA-N 0.000 description 1
- 229960003537 desflurane Drugs 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-M difluoroacetate Chemical compound [O-]C(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical group C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9815684A FR2787107B1 (fr) | 1998-12-11 | 1998-12-11 | Procede d'hydrogenodeshalogenation selective |
| FR98/15684 | 1998-12-11 | ||
| PCT/FR1999/003031 WO2000035834A1 (fr) | 1998-12-11 | 1999-12-07 | Procede d'hydrogenodeshalogenation selective |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002532442A JP2002532442A (ja) | 2002-10-02 |
| JP2002532442A5 JP2002532442A5 (enExample) | 2010-09-24 |
| JP4828701B2 true JP4828701B2 (ja) | 2011-11-30 |
Family
ID=9533885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000588098A Expired - Fee Related JP4828701B2 (ja) | 1998-12-11 | 1999-12-07 | 選択的水素化脱ハロゲン化方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6509495B1 (enExample) |
| EP (1) | EP1137615B1 (enExample) |
| JP (1) | JP4828701B2 (enExample) |
| KR (1) | KR100635844B1 (enExample) |
| CN (1) | CN1269775C (enExample) |
| AT (1) | ATE318252T1 (enExample) |
| AU (1) | AU1566200A (enExample) |
| CA (1) | CA2354159A1 (enExample) |
| DE (1) | DE69929997T2 (enExample) |
| ES (1) | ES2255319T3 (enExample) |
| FR (1) | FR2787107B1 (enExample) |
| WO (1) | WO2000035834A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1574496A1 (de) * | 2004-03-08 | 2005-09-14 | Solvay Fluor GmbH | Herstellung von Verbindungen mit der CHF2- oder CHF-Gruppe |
| WO2007020816A1 (ja) * | 2005-08-12 | 2007-02-22 | Central Glass Company, Limited | ジフルオロ酢酸塩の製造方法 |
| FR2928919B1 (fr) | 2008-03-19 | 2011-07-29 | Rhodia Operations | Procede de preparation de l'acide difluoroacetique et de ses sels |
| FR2933693B1 (fr) | 2008-07-10 | 2010-09-03 | Rhodia Operations | Procede de separation d'un acide carboxylique sous forme salifiee porteur d'au moins un atome d'halogene |
| FR2947264B1 (fr) * | 2009-06-30 | 2012-08-10 | Rhodia Operations | Procedure de preparation de l'acide difluoroacetique |
| CN108568304B (zh) * | 2017-10-12 | 2020-10-09 | 湖南大学 | 一种电催化脱卤催化剂 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0267235A (ja) * | 1988-05-20 | 1990-03-07 | E I Du Pont De Nemours & Co | １，１，１，２‐テトラフルオロエタンの製造方法 |
| JPH07196577A (ja) * | 1993-12-10 | 1995-08-01 | Bayer Ag | 脂肪族のω−ジフルオロカルボキシル化合物の製法 |
| JPH08198804A (ja) * | 1995-01-31 | 1996-08-06 | Dai Ichi Seiyaku Co Ltd | ２−フルオロシクロプロパンカルボン酸類の製法 |
| JPH08268956A (ja) * | 1995-01-31 | 1996-10-15 | Sumitomo Chem Co Ltd | ２−フルオロシクロプロパンカルボン酸類の製造法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2060041C3 (de) * | 1970-12-05 | 1973-10-25 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Herstellung von fluorierten Kohlenwasserstoffen |
| GB1364496A (en) * | 1971-12-14 | 1974-08-21 | Rank Organisation Ltd | Display apparatus |
| US5770767A (en) * | 1995-01-31 | 1998-06-23 | Sumitomo Chemical Company Limited. | Process for producing 2-fluorocyclopropancecarboxlic acid |
-
1998
- 1998-12-11 FR FR9815684A patent/FR2787107B1/fr not_active Expired - Fee Related
-
1999
- 1999-12-07 CN CNB998143332A patent/CN1269775C/zh not_active Expired - Fee Related
- 1999-12-07 ES ES99958253T patent/ES2255319T3/es not_active Expired - Lifetime
- 1999-12-07 DE DE69929997T patent/DE69929997T2/de not_active Expired - Lifetime
- 1999-12-07 EP EP99958253A patent/EP1137615B1/fr not_active Expired - Lifetime
- 1999-12-07 AT AT99958253T patent/ATE318252T1/de not_active IP Right Cessation
- 1999-12-07 CA CA002354159A patent/CA2354159A1/fr not_active Abandoned
- 1999-12-07 KR KR1020017007104A patent/KR100635844B1/ko not_active Expired - Fee Related
- 1999-12-07 AU AU15662/00A patent/AU1566200A/en not_active Abandoned
- 1999-12-07 JP JP2000588098A patent/JP4828701B2/ja not_active Expired - Fee Related
- 1999-12-07 US US09/857,678 patent/US6509495B1/en not_active Expired - Lifetime
- 1999-12-07 WO PCT/FR1999/003031 patent/WO2000035834A1/fr not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0267235A (ja) * | 1988-05-20 | 1990-03-07 | E I Du Pont De Nemours & Co | １，１，１，２‐テトラフルオロエタンの製造方法 |
| JPH07196577A (ja) * | 1993-12-10 | 1995-08-01 | Bayer Ag | 脂肪族のω−ジフルオロカルボキシル化合物の製法 |
| JPH08198804A (ja) * | 1995-01-31 | 1996-08-06 | Dai Ichi Seiyaku Co Ltd | ２−フルオロシクロプロパンカルボン酸類の製法 |
| JPH08268956A (ja) * | 1995-01-31 | 1996-10-15 | Sumitomo Chem Co Ltd | ２−フルオロシクロプロパンカルボン酸類の製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100635844B1 (ko) | 2006-10-18 |
| KR20010082329A (ko) | 2001-08-29 |
| CN1330617A (zh) | 2002-01-09 |
| FR2787107A1 (fr) | 2000-06-16 |
| FR2787107B1 (fr) | 2003-11-14 |
| DE69929997D1 (de) | 2006-04-27 |
| CN1269775C (zh) | 2006-08-16 |
| EP1137615B1 (fr) | 2006-02-22 |
| AU1566200A (en) | 2000-07-03 |
| JP2002532442A (ja) | 2002-10-02 |
| WO2000035834A1 (fr) | 2000-06-22 |
| ES2255319T3 (es) | 2006-06-16 |
| DE69929997T2 (de) | 2006-07-27 |
| CA2354159A1 (fr) | 2000-06-22 |
| US6509495B1 (en) | 2003-01-21 |
| EP1137615A1 (fr) | 2001-10-04 |
| ATE318252T1 (de) | 2006-03-15 |
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