DE2733663C2 - - Google Patents
Info
- Publication number
- DE2733663C2 DE2733663C2 DE2733663A DE2733663A DE2733663C2 DE 2733663 C2 DE2733663 C2 DE 2733663C2 DE 2733663 A DE2733663 A DE 2733663A DE 2733663 A DE2733663 A DE 2733663A DE 2733663 C2 DE2733663 C2 DE 2733663C2
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- reaction
- mpa
- catalyst
- methyl
- 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
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 20
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 14
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 229910001505 inorganic iodide Inorganic materials 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 claims description 3
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 229910052707 ruthenium Inorganic materials 0.000 description 21
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- JTDNNCYXCFHBGG-UHFFFAOYSA-L tin(ii) iodide Chemical compound I[Sn]I JTDNNCYXCFHBGG-UHFFFAOYSA-L 0.000 description 9
- 235000019260 propionic acid Nutrition 0.000 description 7
- 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 7
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- -1 aliphatic carboxylic acids Alcohols Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229940017219 methyl propionate Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910001503 inorganic bromide Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- IYWJIYWFPADQAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;ruthenium Chemical compound [Ru].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O IYWJIYWFPADQAN-LNTINUHCSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NNFJGOVHCOUFBN-UHFFFAOYSA-N C(C)CC(=O)O.C(C)(=O)OCC.C(C)(=O)O Chemical compound C(C)CC(=O)O.C(C)(=O)OCC.C(C)(=O)O NNFJGOVHCOUFBN-UHFFFAOYSA-N 0.000 description 1
- OKIIEJOIXGHUKX-UHFFFAOYSA-L Cadmium iodide Inorganic materials [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021584 Cobalt(II) iodide Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021579 Iron(II) iodide Inorganic materials 0.000 description 1
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910021588 Nickel(II) iodide Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- UAYWVJHJZHQCIE-UHFFFAOYSA-L Zinc iodide Inorganic materials I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 description 1
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- IBSOYFJDSVROOT-UHFFFAOYSA-L diiodonickel;hexahydrate Chemical compound O.O.O.O.O.O.I[Ni]I IBSOYFJDSVROOT-UHFFFAOYSA-L 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- RCYSGAYIEFAJTG-UHFFFAOYSA-N methyl acetate;propanoic acid Chemical compound CCC(O)=O.COC(C)=O RCYSGAYIEFAJTG-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J25/00—Transit-time tubes, e.g. klystrons, travelling-wave tubes, magnetrons
- H01J25/02—Tubes with electron stream modulated in velocity or density in a modulator zone and thereafter giving up energy in an inducing zone, the zones being associated with one or more resonators
- H01J25/04—Tubes having one or more resonators, without reflection of the electron stream, and in which the modulation produced in the modulator zone is mainly density modulation, e.g. Heaff tube
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2578276A IT1062144B (it) | 1976-07-28 | 1976-07-28 | Procedimento per la preparazione di esteri da eteri od esteri omologhi inferiori |
| IT2222377A IT1115644B (it) | 1977-04-07 | 1977-04-07 | Procedimento per la preparazione di esteri da eteri od esteri omologhi inferiori |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2733663A1 DE2733663A1 (de) | 1978-02-02 |
| DE2733663C2 true DE2733663C2 (en, 2012) | 1988-09-15 |
Family
ID=26328132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772733663 Granted DE2733663A1 (de) | 1976-07-28 | 1977-07-26 | Verfahren zur herstellung von carbonsaeureestern und katalysator zur durchfuehrung desselben |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4189441A (en, 2012) |
| JP (1) | JPS5331612A (en, 2012) |
| DE (1) | DE2733663A1 (en, 2012) |
| FR (1) | FR2359811A1 (en, 2012) |
| GB (1) | GB1574096A (en, 2012) |
| NL (1) | NL7708158A (en, 2012) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1138898A (en) * | 1978-04-04 | 1983-01-04 | Jimmy Peress | Phenylethyl alcohol preparation with mixed feeds |
| DE2941232A1 (de) * | 1979-10-11 | 1981-04-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 1,1-diacetoxiethan |
| FR2471965A1 (fr) * | 1979-12-21 | 1981-06-26 | Rhone Poulenc Ind | Procede de preparation de carboxylates d'alkyles a partir de leurs homologues inferieurs |
| ZA811979B (en) * | 1980-03-31 | 1982-04-28 | Union Carbide Corp | Process for producing methanol from synthesis gas |
| US4540712A (en) * | 1980-03-31 | 1985-09-10 | Union Carbide Corporation | Process for producing methanol from synthesis gas |
| CA1173059A (en) * | 1980-04-21 | 1984-08-21 | David W. Smith | Manufacture of oxygenated compounds |
| JPS5925776B2 (ja) * | 1980-06-09 | 1984-06-21 | 三菱瓦斯化学株式会社 | カルボン酸アルキルエステルの製造法 |
| US4334093A (en) * | 1980-06-30 | 1982-06-08 | Texaco, Inc. | Method of preparing aliphatic carboxylic acids |
| US4334094A (en) * | 1980-06-30 | 1982-06-08 | Texaco Inc. | Method of preparing aliphatic carboxylic acids |
| US4334092A (en) * | 1980-06-30 | 1982-06-08 | Texaco Inc. | Method of preparing aliphatic carboxylic acids |
| FR2488248A1 (fr) * | 1980-08-07 | 1982-02-12 | Rhone Poulenc Ind | Procede d'hydrocarbonylation et/ou de carbonylation de carboxylates d'alkyles |
| FR2488251A1 (fr) * | 1980-08-07 | 1982-02-12 | Rhone Poulenc Ind | Procede d'hydrocarbonylation et/ou de carbonylation de carboxylates d'alkyles |
| DE3168329D1 (en) * | 1980-09-16 | 1985-02-28 | Mitsubishi Gas Chemical Co | One step process for producing vinyl acetate |
| JPS57114550A (en) * | 1981-01-07 | 1982-07-16 | Mitsubishi Chem Ind Ltd | Preparation of carboxylic acid ester |
| IT1144698B (it) * | 1981-04-06 | 1986-10-29 | Giuseppe Braca | Processo di produzione all'acetato di etile mediante omologazione dell'acetato di metile |
| US4897473A (en) * | 1981-05-01 | 1990-01-30 | Union Carbide Chemicals And Plastics Company Inc. | Homologation of carbonyloxy containing compounds |
| FR2507597B1 (fr) * | 1981-06-12 | 1985-12-13 | Rhone Poulenc Chim Base | Procede de carbonylation de l'acetate de methyle |
| US4366259A (en) * | 1981-10-29 | 1982-12-28 | Texaco, Inc. | Production of acetic acid and propionic acid and their esters |
| US4640802A (en) * | 1981-12-10 | 1987-02-03 | Shell Oil Company | Process for the co-production of carboxylic acids and carboxylic acid esters |
| US4664851A (en) * | 1981-12-30 | 1987-05-12 | Shell Oil Company | Process for the co-production of carboxylic acids and carboxylic acid esters |
| US4414410A (en) * | 1982-01-13 | 1983-11-08 | Texaco Inc. | Process for preparing alkyl esters by homologation of the next lower alkyl ester |
| US4480115A (en) * | 1983-03-17 | 1984-10-30 | Celanese Corporation | Direct hydrogenation of carboxylic acids to alcohol and esters |
| IT1161942B (it) * | 1983-06-15 | 1987-03-18 | Consiglio Nazionale Ricerche | Processo per la produzione di acetato di etile per omologazione di acetato di metile |
| US4625051A (en) * | 1983-06-23 | 1986-11-25 | Chevron Research Company | Carboxylic acid ester homologation using a sulfided cobalt catalyst |
| US4628114A (en) * | 1983-06-23 | 1986-12-09 | Chevron Research Company | Carboxylic acid ester homologation using a sulfided nickel catalyst |
| US4625050A (en) * | 1983-06-23 | 1986-11-25 | Chevron Research Company | Ether homologation to esters and alcohols using a heterogeneous sulfided catalyst |
| US4519956A (en) * | 1983-07-21 | 1985-05-28 | Texaco Inc. | Process for selectively preparing acetic anhydride by carbonylation of methyl acetate in the presence of an iodide-free catalyst system |
| US4511741A (en) * | 1983-12-02 | 1985-04-16 | Union Carbide Corporation | Production of aldehydes from organic acid esters |
| US9700177B2 (en) | 2013-03-01 | 2017-07-11 | Whirlpool Corporation | Food processing device jar lock |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855307A (en) * | 1967-02-20 | 1974-12-17 | Monsanto Co | Catalysis |
| FR2023002A1 (fr) * | 1968-11-11 | 1970-08-07 | Shell Int Research | Procede de preparation d esters |
-
1977
- 1977-07-22 NL NL7708158A patent/NL7708158A/xx not_active Application Discontinuation
- 1977-07-25 US US05/818,857 patent/US4189441A/en not_active Expired - Lifetime
- 1977-07-26 DE DE19772733663 patent/DE2733663A1/de active Granted
- 1977-07-26 FR FR7722876A patent/FR2359811A1/fr active Granted
- 1977-07-27 GB GB31620/77A patent/GB1574096A/en not_active Expired
- 1977-07-27 JP JP8935377A patent/JPS5331612A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2733663A1 (de) | 1978-02-02 |
| GB1574096A (en) | 1980-09-03 |
| JPS5331612A (en) | 1978-03-25 |
| FR2359811B1 (en, 2012) | 1980-05-16 |
| US4189441A (en) | 1980-02-19 |
| NL7708158A (nl) | 1978-01-31 |
| FR2359811A1 (fr) | 1978-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2733663C2 (en, 2012) | ||
| DE69407846T2 (de) | Verfahren zur Herstellung von Carbonsäuren oder ihrer Ester in gegenwart des auf Iridium basierten Katalysators | |
| DE2828041C2 (de) | Verfahren zur Herstellung von Arylbrenztraubensäuren | |
| CH623556A5 (en, 2012) | ||
| DE2259072A1 (de) | Verfahren zur herstellung von arylessigsaeuren | |
| DE2462444B2 (de) | Verfahren zur Herstellung von Monocarbonsäureester« | |
| DE2749955C2 (de) | Verfahren zur Herstellung niedrigmolekularer Alkanmonocarbonsäuren | |
| DE69007256T3 (de) | Verfahren zur Herstellung von Ibuprofen und dessen Alkylester. | |
| DE2749954C2 (de) | Verfahren zur Herstellung niedrigmolekularer Alkanmonocarbonsäuren | |
| DE69328591T2 (de) | Hydroformylierungsverfahren mit einem bimetallischen Katalysator | |
| DE69308888T2 (de) | Verfahren zur herstellung von octadienolen | |
| DE2148156A1 (de) | Verfahren zur Herstellung von eine Octadienyl-Kohlenwasserstoffkette enthaltenden Äthern oder Alkoholen | |
| DE3037280C2 (de) | Verfahren zur Herstellung von niedrigmolekularen Monocarbonsäureanhydriden | |
| DE2303271C3 (de) | Verfahren zur Herstellung von Essigsäure oder deren Gemischen mit Methylacetat | |
| DE3335595C2 (en, 2012) | ||
| EP0170965A2 (de) | Verfahren zur gemeinsamen Herstellung von Carbonsäuren und Carbonsäureanhydriden sowie gegebenenfalls Carbonsäureestern | |
| DD155319A5 (de) | Verfahren zur herstellung von carbonsaeurealkylestern | |
| DE2240398C3 (de) | Verfahren zur Herstellung von Arylessigsäurealkylestern | |
| EP0084833B1 (de) | Verfahren zur Herstellung von Ethanol und n-Propanol aus Methanol und Synthesegas | |
| DE2846709C2 (de) | Verfahren zur Herstellung einer aliphatischen Carbonsäure | |
| DE3034019C2 (de) | Verfahren zur gleichzeitigen Herstellung von Estern von Alkanolen und vicinalen Glykolen | |
| DE3879937T2 (de) | Nickel enthaltender katalysator. | |
| DE68907050T2 (de) | Verfahren zur carbonylierung von aromatischen jodverbindungen. | |
| DE2750719C2 (en, 2012) | ||
| DE3046481A1 (de) | Verfahren zur herstellung von ethanol und n-propanol aus methanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |