IE44306B1 - Production of alcohols by catalytic hydrogenation of carboxyhlic acids,lactones or anhydrides - Google Patents
Production of alcohols by catalytic hydrogenation of carboxyhlic acids,lactones or anhydridesInfo
- Publication number
- IE44306B1 IE44306B1 IE27677A IE27677A IE44306B1 IE 44306 B1 IE44306 B1 IE 44306B1 IE 27677 A IE27677 A IE 27677A IE 27677 A IE27677 A IE 27677A IE 44306 B1 IE44306 B1 IE 44306B1
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- catalyst
- hydrogenation
- process according
- acids
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 23
- 150000008064 anhydrides Chemical class 0.000 title claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000002596 lactones Chemical class 0.000 title claims description 4
- 150000001298 alcohols Chemical class 0.000 title description 5
- 150000007513 acids Chemical class 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 43
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 10
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 6
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- 239000001361 adipic acid Substances 0.000 claims description 12
- 235000011037 adipic acid Nutrition 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 3
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 229940107700 pyruvic acid Drugs 0.000 claims description 2
- 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 3
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009183 running Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000004063 acid-resistant material Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect 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
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
Classifications
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/656—Manganese, technetium or rhenium
- B01J23/6567—Rhenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762605107 DE2605107C3 (de) | 1976-02-10 | 1976-02-10 | Verfahren zur Herstellung von Diolen durch katalytische Hydrierung der entsprechenden Dicarbonsäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44306L IE44306L (en) | 1977-08-10 |
| IE44306B1 true IE44306B1 (en) | 1981-10-07 |
Family
ID=5969470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE27677A IE44306B1 (en) | 1976-02-10 | 1977-02-09 | Production of alcohols by catalytic hydrogenation of carboxyhlic acids,lactones or anhydrides |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5297901A (enExample) |
| BE (1) | BE851227A (enExample) |
| DE (1) | DE2605107C3 (enExample) |
| DK (1) | DK54577A (enExample) |
| FR (1) | FR2340922A1 (enExample) |
| GB (1) | GB1534232A (enExample) |
| IE (1) | IE44306B1 (enExample) |
| IT (1) | IT1076160B (enExample) |
| LU (1) | LU76717A1 (enExample) |
| NL (1) | NL7701342A (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2519817A1 (de) * | 1975-05-03 | 1976-11-11 | Hoechst Ag | Verfahren zur herstellung von butandiol-(1.4) |
| DE2715666A1 (de) * | 1977-04-07 | 1978-10-12 | Hoechst Ag | Verfahren zur herstellung von aethylenglykol |
| DE2938656C3 (de) * | 1979-09-25 | 1987-06-19 | Beiersdorf Ag, 2000 Hamburg | Verfahren zur Herstellung von Wollwachsalkoholen und deren Verwendung als Emulgatoren |
| US4317918A (en) * | 1979-11-05 | 1982-03-02 | Sumitomo Chemical Co., Ltd. | Process for preparing alcohols |
| JPS5681306A (en) * | 1979-12-06 | 1981-07-03 | Nippon Zeon Co Ltd | Hydrogenation of conjugated diene type polymer |
| US4550185A (en) * | 1983-12-22 | 1985-10-29 | E. I. Du Pont De Nemours And Company | Process for making tetrahydrofuran and 1,4-butanediol using Pd/Re hydrogenation catalyst |
| US4609636A (en) * | 1983-12-22 | 1986-09-02 | E. I. Du Pont De Nemours And Company | Pd/Re hydrogenation catalyst for making tetrahydrofuran and 1,4-butanediol |
| GB8509530D0 (en) * | 1985-04-13 | 1985-05-15 | Bp Chem Int Ltd | Hydrogenation of carboxylic acids |
| GB8707595D0 (en) * | 1987-03-31 | 1987-05-07 | British Petroleum Co Plc | Chemical process |
| US5149680A (en) * | 1987-03-31 | 1992-09-22 | The British Petroleum Company P.L.C. | Platinum group metal alloy catalysts for hydrogenation of carboxylic acids and their anhydrides to alcohols and/or esters |
| US4837367A (en) * | 1987-08-03 | 1989-06-06 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds |
| US4837368A (en) * | 1988-02-01 | 1989-06-06 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds and supported catalysts therefor |
| GB8811009D0 (en) * | 1988-05-10 | 1988-06-15 | Bp Chem Int Ltd | Chemical process |
| JP2666151B2 (ja) * | 1988-12-14 | 1997-10-22 | 東燃株式会社 | １，４−ブタンジオールの製造法 |
| DE19500783A1 (de) * | 1995-01-13 | 1996-07-18 | Bayer Ag | Verfahren zur Herstellung von aliphatischen alpha,omega-Diolen |
| US5473086A (en) * | 1995-01-17 | 1995-12-05 | The Standard Oil Co. | Process for the hydrogenation of maleic acid to 1,4-butanediol |
| US5698749A (en) * | 1995-09-06 | 1997-12-16 | The Standard Oil Company | Catalysts for the hydrogenation of aqueous maleic acid to 1,4-butanediol |
| GB2310206A (en) * | 1996-01-31 | 1997-08-20 | Procter & Gamble | Disulfated cleaning agent synthesis |
| DE19754788A1 (de) * | 1997-12-10 | 1999-06-17 | Bayer Ag | Verfahren zur Herstellung von aliphatischen alpha,omega-Diolen |
| DE102004007499A1 (de) * | 2004-02-13 | 2005-09-01 | Basf Ag | Verfahren zur Herstellung optisch aktiver Alkohole oder Carbonsäuren |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235879B (de) * | 1964-03-17 | 1967-03-09 | Basf Ag | Verfahren zur Herstellung von Alkoholen durch katalytische Hydrierung von Carbonsaeuren |
| FR2041421A5 (en) * | 1969-04-23 | 1971-01-29 | Inst Francais Du Petrole | Tetramethyl dinitriles prepn |
| DE1921467B2 (de) * | 1969-04-26 | 1974-09-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zum katalytischer! Hydrieren von organischen Verbindungen |
-
1976
- 1976-02-10 DE DE19762605107 patent/DE2605107C3/de not_active Expired
-
1977
- 1977-02-03 GB GB449777A patent/GB1534232A/en not_active Expired
- 1977-02-08 LU LU76717A patent/LU76717A1/xx unknown
- 1977-02-09 DK DK54577A patent/DK54577A/da not_active Application Discontinuation
- 1977-02-09 FR FR7703643A patent/FR2340922A1/fr active Granted
- 1977-02-09 BE BE174764A patent/BE851227A/xx unknown
- 1977-02-09 NL NL7701342A patent/NL7701342A/xx not_active Application Discontinuation
- 1977-02-09 JP JP1256177A patent/JPS5297901A/ja active Pending
- 1977-02-09 IE IE27677A patent/IE44306B1/en unknown
- 1977-02-09 IT IT2008777A patent/IT1076160B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2605107C3 (de) | 1983-12-29 |
| BE851227A (fr) | 1977-05-31 |
| LU76717A1 (enExample) | 1977-06-30 |
| GB1534232A (en) | 1978-11-29 |
| FR2340922B1 (enExample) | 1981-03-06 |
| FR2340922A1 (fr) | 1977-09-09 |
| DE2605107B2 (de) | 1980-05-22 |
| IE44306L (en) | 1977-08-10 |
| DK54577A (da) | 1977-08-11 |
| NL7701342A (nl) | 1977-08-12 |
| IT1076160B (it) | 1985-04-27 |
| DE2605107A1 (de) | 1977-08-11 |
| JPS5297901A (en) | 1977-08-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE44306B1 (en) | Production of alcohols by catalytic hydrogenation of carboxyhlic acids,lactones or anhydrides | |
| EP0198681B1 (en) | Alcohols production by hydrogenation of carboxylic acids | |
| US4973717A (en) | Production of alcohols and ethers by the catalysed hydrogenation of esters | |
| US20080207953A1 (en) | Catalyst and Method for Hyrogenating Carbonyl Compounds | |
| JP4741073B2 (ja) | １，６−ヘキサンジオールおよび６−ヒドロキシカプロン酸またはそのエステルの製造方法 | |
| US4609636A (en) | Pd/Re hydrogenation catalyst for making tetrahydrofuran and 1,4-butanediol | |
| JPS62155231A (ja) | ラクトンのグリコ−ルへの水素化法 | |
| JPS61106528A (ja) | アルコ−ル及び／又はエステルの気相形成法 | |
| KR19980703190A (ko) | 푸란으로부터 1,4-부탄디올 및 테트라히드로푸란을 제조하는 방법 | |
| EP0319116B1 (en) | Hydrogenation catalyst | |
| US4885410A (en) | Hydrogenation catalyst | |
| JPH01168346A (ja) | 水素化触媒及びその製造方法並びに該触媒を使用する接触方法 | |
| US6787677B2 (en) | Hydrogenation of carbonyl compounds | |
| US3344196A (en) | Hydrogenation of alkanoic dicarboxylic acids using sintered cobalt catalyst | |
| EP0277562A2 (en) | Hydrogenation of citric acid and substituted citric acids to 3-substituted tetrahydrofuran, 3- and 4-substituted butyrolactones and mixtures thereof | |
| US5969194A (en) | Process for preparing 1, 6-hexanediol | |
| RU2119905C1 (ru) | Способ получения 1,4-бутандиола | |
| US3169975A (en) | Production of saturated cyclic dicarboxylic anhydrides | |
| JP2000007596A (ja) | １，４−シクロヘキサンジメタノールの製造方法 | |
| US20010029302A1 (en) | Preparation of gamma-butyrolactone by catalytic hydrogenation of maleic anhydride | |
| KR100365462B1 (ko) | 1,4-부탄디올의제조방법 | |
| US5118821A (en) | Process for the production of gamma-butyrolactone | |
| US3994928A (en) | Process for the production of γ-butyrolactone | |
| US3769331A (en) | Process for the preparation of acetates of 1,3-propanediol | |
| US4025534A (en) | Continuous process for producing gamma-butyrolactone by catalytic hydrogenation of maleic anhydride |