GB1574096A - Process for preparing esters from lower homologous ehters or esters - Google Patents
Process for preparing esters from lower homologous ehters or esters Download PDFInfo
- Publication number
- GB1574096A GB1574096A GB31620/77A GB3162077A GB1574096A GB 1574096 A GB1574096 A GB 1574096A GB 31620/77 A GB31620/77 A GB 31620/77A GB 3162077 A GB3162077 A GB 3162077A GB 1574096 A GB1574096 A GB 1574096A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodide
- ruthenium
- esters
- bromide
- reaction
- 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
- 150000002148 esters Chemical class 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 33
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 18
- 150000001735 carboxylic acids Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- -1 alkylaryl iodides Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 229910001505 inorganic iodide Inorganic materials 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
- 229940071870 hydroiodic acid Drugs 0.000 claims description 7
- 229910001503 inorganic bromide Inorganic materials 0.000 claims description 7
- 150000004694 iodide salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 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 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 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 claims description 6
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 6
- 150000001649 bromium compounds Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Chemical class 0.000 claims description 4
- 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 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 150000003303 ruthenium Chemical class 0.000 claims description 2
- WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 claims description 2
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000003842 bromide salts Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002497 iodine compounds Chemical class 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 24
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 20
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229940093499 ethyl acetate Drugs 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 7
- 229940035423 ethyl ether Drugs 0.000 description 7
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical class CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 4
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 4
- 238000005810 carbonylation reaction Methods 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229940017219 methyl propionate Drugs 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241001558496 Talpa caeca Species 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 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
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DUKZZNAMPZKMCO-UHFFFAOYSA-N CC(O)=O.COC(C)=O.CCOC(C)=O Chemical compound CC(O)=O.COC(C)=O.CCOC(C)=O DUKZZNAMPZKMCO-UHFFFAOYSA-N 0.000 description 1
- 101000685083 Centruroides infamatus Beta-toxin Cii1 Proteins 0.000 description 1
- 101000687448 Homo sapiens REST corepressor 1 Proteins 0.000 description 1
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
- 102100024864 REST corepressor 1 Human genes 0.000 description 1
- XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- NZDGNIJHHWDSIW-UHFFFAOYSA-N ethyl acetate;methyl acetate Chemical compound COC(C)=O.CCOC(C)=O NZDGNIJHHWDSIW-UHFFFAOYSA-N 0.000 description 1
- UDOUIRSXTJAWOV-UHFFFAOYSA-N ethyl acetate;propyl acetate Chemical compound CCOC(C)=O.CCCOC(C)=O UDOUIRSXTJAWOV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000012429 reaction media 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
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 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
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1574096A true GB1574096A (en) | 1980-09-03 |
Family
ID=26328132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31620/77A Expired GB1574096A (en) | 1976-07-28 | 1977-07-27 | Process for preparing esters from lower homologous ehters or esters |
Country Status (6)
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 |
| 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 |
| US4334093A (en) * | 1980-06-30 | 1982-06-08 | Texaco, Inc. | Method of preparing aliphatic carboxylic acids |
| FR2488251A1 (fr) * | 1980-08-07 | 1982-02-12 | Rhone Poulenc Ind | Procede d'hydrocarbonylation et/ou de carbonylation de carboxylates d'alkyles |
| FR2488248A1 (fr) | 1980-08-07 | 1982-02-12 | Rhone Poulenc Ind | Procede d'hydrocarbonylation et/ou de carbonylation de carboxylates d'alkyles |
| EP0048173B1 (en) * | 1980-09-16 | 1985-01-16 | Mitsubishi Gas Chemical Company, Inc. | 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 |
| US4362821A (en) * | 1981-10-29 | 1982-12-07 | Texaco Inc. | Process for preparing alkanols from synthesis gas |
| 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 FR FR7722876A patent/FR2359811A1/fr active Granted
- 1977-07-26 DE DE19772733663 patent/DE2733663A1/de active Granted
- 1977-07-27 JP JP8935377A patent/JPS5331612A/ja active Pending
- 1977-07-27 GB GB31620/77A patent/GB1574096A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2733663A1 (de) | 1978-02-02 |
| FR2359811A1 (fr) | 1978-02-24 |
| FR2359811B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-16 |
| DE2733663C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-09-15 |
| JPS5331612A (en) | 1978-03-25 |
| US4189441A (en) | 1980-02-19 |
| NL7708158A (nl) | 1978-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |