WO2001017939A1 - Process for the production of fluorocarboxylic acid anhydrides - Google Patents
Process for the production of fluorocarboxylic acid anhydrides Download PDFInfo
- Publication number
- WO2001017939A1 WO2001017939A1 PCT/US2000/022188 US0022188W WO0117939A1 WO 2001017939 A1 WO2001017939 A1 WO 2001017939A1 US 0022188 W US0022188 W US 0022188W WO 0117939 A1 WO0117939 A1 WO 0117939A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tfa
- anhydride
- reactive distillation
- tfaa
- ketene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 65
- 230000008569 process Effects 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 150000008065 acid anhydrides Chemical class 0.000 title claims abstract description 9
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims abstract description 141
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 128
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 81
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 81
- HINSMVRGSUGPBM-UHFFFAOYSA-N acetyl 2,2,2-trifluoroacetate Chemical compound CC(=O)OC(=O)C(F)(F)F HINSMVRGSUGPBM-UHFFFAOYSA-N 0.000 claims abstract description 59
- 238000009835 boiling Methods 0.000 claims abstract description 49
- 238000000066 reactive distillation Methods 0.000 claims abstract description 49
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims abstract description 36
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 238000004821 distillation Methods 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 8
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- UFFSXJKVKBQEHC-UHFFFAOYSA-N heptafluorobutyric anhydride Chemical class FC(F)(F)C(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)C(F)(F)F UFFSXJKVKBQEHC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 26
- 239000012263 liquid product Substances 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000007323 disproportionation reaction Methods 0.000 description 12
- -1 fluoro-substituted carboxylic acid Chemical class 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical class ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000004075 acetic anhydrides Chemical class 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000002547 anomalous effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- HDYQLGLEPPGPEV-UHFFFAOYSA-N benzyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OCC1=CC=CC=C1 HDYQLGLEPPGPEV-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 238000005515 capillary zone electrophoresis Methods 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method 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
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical class OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60012337T DE60012337T2 (en) | 1999-09-03 | 2000-08-14 | Process for the preparation of fluorocarboxylic acid anhydrides |
JP2001521686A JP2003508507A (en) | 1999-09-03 | 2000-08-14 | Method for producing fluorocarboxylic anhydride |
MXPA02002210A MXPA02002210A (en) | 1999-09-03 | 2000-08-14 | Process for the production of fluorocarboxylic acid anhydrides. |
BR0013692-1A BR0013692A (en) | 1999-09-03 | 2000-08-14 | Process for the co-production of symmetrical fluorocarboxylic acid anhydride and acetic anhydride, trifluoroacetic anhydride, and carboxylic anhydride, and, process for the production of trifluoroacetic anhydride |
EP00954037A EP1208074B1 (en) | 1999-09-03 | 2000-08-14 | Process for the production of fluorocarboxylic acid anhydrides |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15229099P | 1999-09-03 | 1999-09-03 | |
US60/152,290 | 1999-09-03 | ||
US09/520,526 US6248923B1 (en) | 1999-09-03 | 2000-03-08 | Process for the production of fluorocarboxylic acid anhydrides |
US09/520,526 | 2000-03-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001017939A1 true WO2001017939A1 (en) | 2001-03-15 |
Family
ID=26849423
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/022188 WO2001017939A1 (en) | 1999-09-03 | 2000-08-14 | Process for the production of fluorocarboxylic acid anhydrides |
Country Status (8)
Country | Link |
---|---|
US (1) | US6248923B1 (en) |
EP (1) | EP1208074B1 (en) |
JP (1) | JP2003508507A (en) |
CN (1) | CN1384813A (en) |
BR (1) | BR0013692A (en) |
DE (1) | DE60012337T2 (en) |
MX (1) | MXPA02002210A (en) |
WO (1) | WO2001017939A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6911561B2 (en) | 2001-06-05 | 2005-06-28 | Regents Of The University Of Minnesota | Compositions including fluorinated peroxides, methods of making, and the use thereof |
US7135597B2 (en) | 2002-10-11 | 2006-11-14 | Akzo Nobel N.V. | Process for the preparation of monochloroacetic acid |
WO2017129759A1 (en) | 2016-01-28 | 2017-08-03 | Solvay Sa | Halogen substituted diketones, pyrazole compounds and processes for the manufacture of pyrazole compounds |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60329305D1 (en) * | 2002-09-25 | 2009-10-29 | Du Pont | PROCESS FOR THE PREPARATION OF FLUORO CARBON SOLUTIONS |
EP1546081B1 (en) * | 2002-09-30 | 2012-12-19 | Daikin Industries, Ltd. | Process for preparing fluorocarboxylic acids |
CN101108797B (en) * | 2007-08-03 | 2010-04-14 | 申厚宝 | Technique of manufacturing trifluoro acetic anhydride |
FR2996147B1 (en) * | 2012-10-03 | 2015-05-29 | Rhodia Operations | PROCESS FOR TREATING FLUID ACID |
CN104529965B (en) * | 2014-12-03 | 2017-05-24 | 江苏尚莱特医药化工材料有限公司 | Hexafluoro dianhydride preparation method |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4595541A (en) * | 1984-06-13 | 1986-06-17 | Rhone Poulenc Specialties Chimiques | Process for the preparation of trifluoroacetic anhydride |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4538Y1 (en) | 1965-04-28 | 1970-01-06 |
-
2000
- 2000-03-08 US US09/520,526 patent/US6248923B1/en not_active Expired - Lifetime
- 2000-08-14 JP JP2001521686A patent/JP2003508507A/en active Pending
- 2000-08-14 EP EP00954037A patent/EP1208074B1/en not_active Expired - Lifetime
- 2000-08-14 BR BR0013692-1A patent/BR0013692A/en not_active Application Discontinuation
- 2000-08-14 WO PCT/US2000/022188 patent/WO2001017939A1/en active IP Right Grant
- 2000-08-14 CN CN00815032A patent/CN1384813A/en active Pending
- 2000-08-14 DE DE60012337T patent/DE60012337T2/en not_active Expired - Lifetime
- 2000-08-14 MX MXPA02002210A patent/MXPA02002210A/en unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4595541A (en) * | 1984-06-13 | 1986-06-17 | Rhone Poulenc Specialties Chimiques | Process for the preparation of trifluoroacetic anhydride |
Non-Patent Citations (3)
Title |
---|
A. FERRIS AND W. EMMONS: "Metathetical Reactions of Silver Salts in Solution. I The Synthesis of Acyl Trifluoroacetates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 75, 1952, pages 232 - 233, XP002153773 * |
K. NAGAYAMA, I. SHIMIZU AND A. YAMAMOTO: "Oxidative addition of aryl and benzyl trifluoroacetates to zerovalent palladium complexes with two modes of C-O bond cleavage processes", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 72, 1999, pages 799 - 803, XP002153775 * |
P. BLAKE AND M. VAYJOOEE: "Reactions of keten. Part VI. Kinetics of gas-phase reactions with halogenated and unsaturated acids, formic acid and acetic-2H-acid", JOURNAL OF THE CHEMICAL SOCIETY (B), 1976, pages 1533 - 1536, XP002153774 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6911561B2 (en) | 2001-06-05 | 2005-06-28 | Regents Of The University Of Minnesota | Compositions including fluorinated peroxides, methods of making, and the use thereof |
US7135597B2 (en) | 2002-10-11 | 2006-11-14 | Akzo Nobel N.V. | Process for the preparation of monochloroacetic acid |
WO2017129759A1 (en) | 2016-01-28 | 2017-08-03 | Solvay Sa | Halogen substituted diketones, pyrazole compounds and processes for the manufacture of pyrazole compounds |
US10829456B2 (en) | 2016-01-28 | 2020-11-10 | Solvay Sa | Halogen substituted diketones, pyrazole compounds and processes for the manufacture of pyrazole compounds |
Also Published As
Publication number | Publication date |
---|---|
DE60012337T2 (en) | 2004-12-02 |
EP1208074B1 (en) | 2004-07-21 |
DE60012337D1 (en) | 2004-08-26 |
US6248923B1 (en) | 2001-06-19 |
CN1384813A (en) | 2002-12-11 |
EP1208074A1 (en) | 2002-05-29 |
BR0013692A (en) | 2002-05-07 |
MXPA02002210A (en) | 2002-09-30 |
JP2003508507A (en) | 2003-03-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1083600A (en) | Continuous production of 2-ethyl-hexyl acrylate free from dioctylether | |
EP1208074B1 (en) | Process for the production of fluorocarboxylic acid anhydrides | |
CA1062647A (en) | Purification of formic acid | |
US4824997A (en) | Method for preparation of alkyl glycolates | |
JPS6125013B2 (en) | ||
EP0209157B1 (en) | Process for the production of alkyl trifluoroacetates | |
US2858334A (en) | Preparation of phthalic acids | |
US4595541A (en) | Process for the preparation of trifluoroacetic anhydride | |
US20070110701A1 (en) | Acyloxyacetic acid polymer and process for producing the same | |
JPH0511101B2 (en) | ||
US4789755A (en) | Process for the preparation of stilbenedicarboxylate derivatives | |
EP1394143A1 (en) | Process for the production of fluorocarboxylic acid anhydrides | |
IE62516B1 (en) | Method for removing hydrogen fluoride from mixtures comprising aromatic ketones | |
EP0060719B1 (en) | Process for the production of methyl acetate by esterifying methanol with acetic acid | |
US6235924B1 (en) | Continuous process for preparing benzoic acid esters | |
US20030125578A1 (en) | Method for producing carboxylic acid benzyl esters | |
EP0068080B1 (en) | Liquid phase synthesis of hexafluoroisobutylene | |
US4038310A (en) | Acid anhydride to react with impurities in the production of perfluorocarboxylic acids | |
EP0630363A1 (en) | Recovery of acetyl values from ethylidene diacetate | |
JPS5967244A (en) | Preparation of ethyl acrylate | |
US20020183544A1 (en) | Continuous process for tertiary butyl esters | |
US4847407A (en) | Diphenyl ester derivative of stilbenedicarboxylic acid | |
JPH04182452A (en) | Production of aliphatic dicarboxylic acid monoester | |
JP2756373B2 (en) | Method for producing 1,1,1-trifluoro-3-nitro-2-propene | |
JPH0491055A (en) | Production of succinic diester and its derivative |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): BR CN JP MX |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2000954037 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2002/002210 Country of ref document: MX |
|
ENP | Entry into the national phase |
Ref country code: JP Ref document number: 2001 521686 Kind code of ref document: A Format of ref document f/p: F |
|
WWE | Wipo information: entry into national phase |
Ref document number: 00815032X Country of ref document: CN |
|
WWP | Wipo information: published in national office |
Ref document number: 2000954037 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 2000954037 Country of ref document: EP |