CS235983B2 - Method of acetic acid production by for mic acid methylester's catalytic re-arrangrment - Google Patents

Method of acetic acid production by for mic acid methylester's catalytic re-arrangrment Download PDF

Info

Publication number: CS235983B2
Authority: CS; Czechoslovakia
Prior art keywords: rhodium; reaction; acetic acid; chromium; catalyst
Prior art date: 1982-10-01

Application number

CS837108A

Other languages

Czech (cs)

English (en)

Inventor

Hans-Ulrich Hoeg

Guenther Bub

Original Assignee

Huels Chemische Werke Ag

Priority date (The priority date 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 date listed.)

1982-10-01

Filing date

1983-09-29

Publication date

1985-05-15

1983-09-29 Application filed by Huels Chemische Werke Ag filed Critical Huels Chemische Werke Ag

1985-05-15 Publication of CS235983B2 publication Critical patent/CS235983B2/cs

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 180
238000000034 method Methods 0.000 title claims abstract description 37
230000003197 catalytic effect Effects 0.000 title claims abstract description 9
238000004519 manufacturing process Methods 0.000 title claims abstract description 7
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 title abstract description 31
238000006243 chemical reaction Methods 0.000 claims abstract description 99
239000003054 catalyst Substances 0.000 claims abstract description 65
239000010948 rhodium Substances 0.000 claims abstract description 61
229910052703 rhodium Inorganic materials 0.000 claims abstract description 57
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 56
229910052751 metal Inorganic materials 0.000 claims abstract description 31
239000002184 metal Substances 0.000 claims abstract description 31
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 25
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 25
230000008569 process Effects 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 21
150000002367 halogens Chemical class 0.000 claims abstract description 21
230000008707 rearrangement Effects 0.000 claims abstract description 13
239000003446 ligand Substances 0.000 claims abstract description 11
239000007791 liquid phase Substances 0.000 claims abstract description 6
150000003284 rhodium compounds Chemical class 0.000 claims abstract description 5
150000003283 rhodium Chemical class 0.000 claims abstract description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 59
235000019253 formic acid Nutrition 0.000 claims description 31
239000011651 chromium Substances 0.000 claims description 27
229910052804 chromium Inorganic materials 0.000 claims description 26
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 23
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 20
230000000737 periodic effect Effects 0.000 claims description 18
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 13
229910052740 iodine Inorganic materials 0.000 claims description 13
239000011630 iodine Substances 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
150000002497 iodine compounds Chemical class 0.000 claims description 9
150000002739 metals Chemical class 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
229910052750 molybdenum Inorganic materials 0.000 claims description 4
239000011733 molybdenum Substances 0.000 claims description 4
239000005078 molybdenum compound Substances 0.000 claims description 3
150000002752 molybdenum compounds Chemical class 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 2
150000002736 metal compounds Chemical class 0.000 abstract description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 16
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
-1 phosphorus organic compound Chemical group 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
239000000047 product Substances 0.000 description 11
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
230000000052 comparative effect Effects 0.000 description 8
239000007789 gas Substances 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
229910052759 nickel Inorganic materials 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 6
239000002253 acid Substances 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000005922 Phosphane Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000004821 distillation Methods 0.000 description 4
229910000043 hydrogen iodide Inorganic materials 0.000 description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
229910000064 phosphane Inorganic materials 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphane group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012263 liquid product Substances 0.000 description 3
238000011068 loading method Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
150000001499 aryl bromides Chemical class 0.000 description 2
229910052797 bismuth Inorganic materials 0.000 description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
238000005810 carbonylation reaction Methods 0.000 description 2
150000001845 chromium compounds Chemical class 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
238000010574 gas phase reaction Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000006872 improvement Effects 0.000 description 2
150000002484 inorganic compounds Chemical class 0.000 description 2
229910010272 inorganic material Inorganic materials 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
150000002897 organic nitrogen compounds Chemical class 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000002407 reforming Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000136406 Comones Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
244000147568 Laurus nobilis Species 0.000 description 1
235000017858 Laurus nobilis Nutrition 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
WVFORMHKBFWUNT-UHFFFAOYSA-N O.O.O.O.[K] Chemical compound O.O.O.O.[K] WVFORMHKBFWUNT-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 description 1
235000005212 Terminalia tomentosa Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001262 acyl bromides Chemical class 0.000 description 1
150000001267 acyl iodides Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001513 alkali metal bromide Inorganic materials 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
ZLMUYRIFFZDBSE-UHFFFAOYSA-H chromium hexafluoride Chemical compound F[Cr](F)(F)(F)(F)F ZLMUYRIFFZDBSE-UHFFFAOYSA-H 0.000 description 1
BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 1
229910021567 chromium(VI) fluoride Inorganic materials 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
UOPIRNHVGHLLDZ-UHFFFAOYSA-L dichlororhodium Chemical compound Cl[Rh]Cl UOPIRNHVGHLLDZ-UHFFFAOYSA-L 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000003546 flue gas Substances 0.000 description 1
229910021478 group 5 element Inorganic materials 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002504 iridium compounds Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
GWKCACMSZXJZEW-UHFFFAOYSA-H rhodium(3+);tricarbonate Chemical compound [Rh+3].[Rh+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GWKCACMSZXJZEW-UHFFFAOYSA-H 0.000 description 1
KXAHUXSHRWNTOD-UHFFFAOYSA-K rhodium(3+);triiodide Chemical compound [Rh+3].[I-].[I-].[I-] KXAHUXSHRWNTOD-UHFFFAOYSA-K 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
150000003304 ruthenium compounds Chemical class 0.000 description 1
238000009958 sewing Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
Materials Engineering (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS837108A 1982-10-01 1983-09-29 Method of acetic acid production by for mic acid methylester's catalytic re-arrangrment CS235983B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823236351 DE3236351A1 (de)	1982-10-01	1982-10-01	Katalysatorsystem und verfahren zur herstellung von essigsaeure durch katalytische umlagerung von ameisensaeuremethylester

Publications (1)

Publication Number	Publication Date
CS235983B2 true CS235983B2 (en)	1985-05-15

Family

ID=6174657

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS837108A CS235983B2 (en)	1982-10-01	1983-09-29	Method of acetic acid production by for mic acid methylester's catalytic re-arrangrment

Country Status (13)

Country	Link
EP (1)	EP0105132B1 (es)
JP (1)	JPS5982947A (es)
KR (1)	KR840006446A (es)
AU (1)	AU1981283A (es)
CS (1)	CS235983B2 (es)
DE (2)	DE3236351A1 (es)
ES (1)	ES8501731A1 (es)
HU (1)	HUT34426A (es)
MY (1)	MY8600706A (es)
PH (1)	PH19591A (es)
PL (1)	PL243916A1 (es)
SU (1)	SU1251795A3 (es)
ZA (1)	ZA837320B (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3333317A1 (de) *	1983-09-15	1985-03-28	Chemische Werke Hüls AG, 4370 Marl	Katalysatorsystem und verfahren zur herstellung von essigsaeure durch katalytische umlagerung von ameisensaeuremethylester
JPS60214756A (ja) *	1984-04-05	1985-10-28	Daicel Chem Ind Ltd	酢酸の製造方法
DE3430663A1 (de) *	1984-08-21	1986-03-06	Hüls AG, 4370 Marl	Katalysatorsystem und verfahren zur herstellung von carbonsaeuren durch umsetzung von carbonsaeureestern mit ameisensaeure

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3717670A (en) *	1968-08-02	1973-02-20	Monsanto Co	Production of carboxylic acids and esters
US4918226A (en) *	1980-08-04	1990-04-17	Exxon Research And Engineering Company	Process for converting formate esters to carboxylic acids

1982
- 1982-10-01 DE DE19823236351 patent/DE3236351A1/de not_active Withdrawn
1983
- 1983-08-06 EP EP83107760A patent/EP0105132B1/de not_active Expired
- 1983-08-06 DE DE8383107760T patent/DE3360126D1/de not_active Expired
- 1983-09-08 PH PH29510A patent/PH19591A/en unknown
- 1983-09-27 PL PL24391683A patent/PL243916A1/xx unknown
- 1983-09-29 CS CS837108A patent/CS235983B2/cs unknown
- 1983-09-30 HU HU833414A patent/HUT34426A/hu unknown
- 1983-09-30 ZA ZA837320A patent/ZA837320B/xx unknown
- 1983-09-30 ES ES526152A patent/ES8501731A1/es not_active Expired
- 1983-09-30 JP JP58180938A patent/JPS5982947A/ja active Pending
- 1983-09-30 SU SU833648253A patent/SU1251795A3/ru active
- 1983-09-30 AU AU19812/83A patent/AU1981283A/en not_active Abandoned
- 1983-09-30 KR KR1019830004647A patent/KR840006446A/ko not_active Withdrawn
1986
- 1986-12-30 MY MY706/86A patent/MY8600706A/xx unknown

Also Published As

Publication number	Publication date
SU1251795A3 (ru)	1986-08-15
EP0105132B1 (de)	1985-04-17
AU1981283A (en)	1984-04-05
EP0105132A1 (de)	1984-04-11
DE3236351A1 (de)	1984-04-12
PL243916A1 (en)	1984-09-10
JPS5982947A (ja)	1984-05-14
MY8600706A (en)	1986-12-31
HUT34426A (en)	1985-03-28
ES526152A0 (es)	1984-12-16
DE3360126D1 (en)	1985-05-23
PH19591A (en)	1986-05-26
ES8501731A1 (es)	1984-12-16
KR840006446A (ko)	1984-11-30
ZA837320B (en)	1984-07-25

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