JP4138025B2 - 脂肪族アルコールの製法 - Google Patents
脂肪族アルコールの製法 Download PDFInfo
- Publication number
- JP4138025B2 JP4138025B2 JP54989498A JP54989498A JP4138025B2 JP 4138025 B2 JP4138025 B2 JP 4138025B2 JP 54989498 A JP54989498 A JP 54989498A JP 54989498 A JP54989498 A JP 54989498A JP 4138025 B2 JP4138025 B2 JP 4138025B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- catalyst
- hydrogenation
- producing
- acetate
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 title description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 10
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 claims description 9
- BIWVHGWGBMHTTP-UHFFFAOYSA-N 2-methylbutane-1,1-diol Chemical compound CCC(C)C(O)O BIWVHGWGBMHTTP-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 7
- 229940071536 silver acetate Drugs 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- -1 phenylphosphinogold nitrate Chemical compound 0.000 claims description 5
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 229940011182 cobalt acetate Drugs 0.000 claims description 4
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- NMKCXDWVQGGMLX-UHFFFAOYSA-O [N+](=O)([O-])[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Au+2].[N+](=O)([O-])[O-] Chemical compound [N+](=O)([O-])[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Au+2].[N+](=O)([O-])[O-] NMKCXDWVQGGMLX-UHFFFAOYSA-O 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 claims 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052702 rhenium Inorganic materials 0.000 description 8
- 150000002596 lactones Chemical class 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 230000000737 periodic effect Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- IWTBVKIGCDZRPL-LURJTMIESA-N 3-Methylbutanol Natural products CC[C@H](C)CCO IWTBVKIGCDZRPL-LURJTMIESA-N 0.000 description 5
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052747 lanthanoid Inorganic materials 0.000 description 4
- 150000002602 lanthanoids Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- GUWZGMWHDAJAOC-UHFFFAOYSA-N oxoplatinum;hydrate Chemical compound O.[Pt]=O GUWZGMWHDAJAOC-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910000765 intermetallic Inorganic materials 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 description 1
- OGFFNYDWXGFGET-UHFFFAOYSA-N acetic acid;silicic acid Chemical compound CC(O)=O.O[Si](O)(O)O OGFFNYDWXGFGET-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 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
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
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)
- Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19720657.3 | 1997-05-16 | ||
| DE19720657A DE19720657A1 (de) | 1997-05-16 | 1997-05-16 | Verfahren zur Herstellung von aliphatischen Alkoholen |
| PCT/EP1998/002777 WO1998052891A1 (de) | 1997-05-16 | 1998-05-12 | Verfahren zur herstellung von aliphatischen alkoholen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001526670A JP2001526670A (ja) | 2001-12-18 |
| JP2001526670A5 JP2001526670A5 (enExample) | 2005-10-06 |
| JP4138025B2 true JP4138025B2 (ja) | 2008-08-20 |
Family
ID=7829721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54989498A Expired - Fee Related JP4138025B2 (ja) | 1997-05-16 | 1998-05-12 | 脂肪族アルコールの製法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6204417B1 (enExample) |
| EP (1) | EP0983219B1 (enExample) |
| JP (1) | JP4138025B2 (enExample) |
| CN (1) | CN1109009C (enExample) |
| DE (2) | DE19720657A1 (enExample) |
| ES (1) | ES2187029T3 (enExample) |
| WO (1) | WO1998052891A1 (enExample) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0210143D0 (en) | 2002-05-02 | 2002-06-12 | Davy Process Techn Ltd | Process |
| DE10241292A1 (de) * | 2002-09-04 | 2004-03-18 | Basf Ag | Verfahren zur Herstellung optisch aktiver 2-Amino-, 2-Hydroxy oder 2-Alkoxy-1-alkohole |
| JP4034289B2 (ja) * | 2004-04-02 | 2008-01-16 | 花王株式会社 | 脂肪アルコールの製造方法 |
| US20080248540A1 (en) * | 2007-04-03 | 2008-10-09 | The Ohio State University | Methods of producing butanol |
| KR101588052B1 (ko) * | 2008-03-28 | 2016-01-25 | 에스케이이노베이션 주식회사 | 발효액으로부터 부티르산을 추출하고 부티르산을 바이오연료로 화학적으로 전환하는 방법 |
| US8637714B2 (en) | 2008-07-31 | 2014-01-28 | Celanese International Corporation | Process for producing ethanol over catalysts containing platinum and palladium |
| US8357519B2 (en) * | 2008-11-19 | 2013-01-22 | The Ohio State University | Methods and processes for producing esters |
| CN102300635B (zh) * | 2009-10-26 | 2014-10-29 | 国际人造丝公司 | 用于通过将乙酸加氢生产乙醇的包含在含硅载体上的铂-锡的催化剂 |
| US8658843B2 (en) | 2011-10-06 | 2014-02-25 | Celanese International Corporation | Hydrogenation catalysts prepared from polyoxometalate precursors and process for using same to produce ethanol while minimizing diethyl ether formation |
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| CN103282333A (zh) | 2011-12-22 | 2013-09-04 | 国际人造丝公司 | 使用具有无定形载体的加氢催化剂的乙醇方法 |
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| US9000234B2 (en) | 2011-12-22 | 2015-04-07 | Celanese International Corporation | Calcination of modified support to prepare hydrogenation catalysts |
| US8455702B1 (en) | 2011-12-29 | 2013-06-04 | Celanese International Corporation | Cobalt and tin catalysts for producing ethanol |
| US9079172B2 (en) | 2012-03-13 | 2015-07-14 | Celanese International Corporation | Promoters for cobalt-tin catalysts for reducing alkanoic acids |
| US9333496B2 (en) | 2012-02-29 | 2016-05-10 | Celanese International Corporation | Cobalt/tin catalyst for producing ethanol |
| WO2013103392A1 (en) | 2012-01-06 | 2013-07-11 | Celanese International Corporation | Hydrogenation catalyst and process for producing ethanol using the catalyst |
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| US9024086B2 (en) | 2012-01-06 | 2015-05-05 | Celanese International Corporation | Hydrogenation catalysts with acidic sites |
| US8815768B2 (en) | 2012-01-06 | 2014-08-26 | Celanese International Corporation | Processes for making catalysts with acidic precursors |
| US8981164B2 (en) | 2012-01-06 | 2015-03-17 | Celanese International Corporation | Cobalt and tin hydrogenation catalysts |
| US8841230B2 (en) | 2012-01-06 | 2014-09-23 | Celanese International Corporation | Processes for making catalysts with metal halide precursors |
| AU2012363796A1 (en) | 2012-01-06 | 2014-07-03 | Celanese International Corporation | Cobalt-containing hydrogenation catalysts and processes for making same |
| US8980789B2 (en) | 2012-01-06 | 2015-03-17 | Celanese International Corporation | Modified catalyst supports |
| WO2013103393A1 (en) | 2012-01-06 | 2013-07-11 | Celanese International Corporation | Processes for making catalysts comprising precious metal and active metal modified support |
| US8802588B2 (en) | 2012-01-23 | 2014-08-12 | Celanese International Corporation | Bismuth catalyst composition and process for manufacturing ethanol mixture |
| US20130197278A1 (en) | 2012-01-27 | 2013-08-01 | Celanese International Corporation | Process For Manufacturing Ethanol Using A Metallic Catalyst Supported on Titania |
| US9050585B2 (en) | 2012-02-10 | 2015-06-09 | Celanese International Corporation | Chemisorption of ethyl acetate during hydrogenation of acetic acid to ethanol |
| US8729317B2 (en) | 2012-02-15 | 2014-05-20 | Celanese International Corporation | Ethanol manufacturing process over catalyst with cesium and support comprising tungsten or oxides thereof |
| US20130225876A1 (en) | 2012-02-29 | 2013-08-29 | Celanese International Corporation | Hydrogenation Catalyst Using Multiple Impregnations of an Active Metal Solution |
| US9126194B2 (en) | 2012-02-29 | 2015-09-08 | Celanese International Corporation | Catalyst having support containing tin and process for manufacturing ethanol |
| US8927786B2 (en) | 2012-03-13 | 2015-01-06 | Celanese International Corporation | Ethanol manufacturing process over catalyst having improved radial crush strength |
| US8536383B1 (en) | 2012-03-14 | 2013-09-17 | Celanese International Corporation | Rhodium/tin catalysts and processes for producing ethanol |
| US9073042B2 (en) | 2012-03-14 | 2015-07-07 | Celanese International Corporation | Acetic acid hydrogenation over a group VIII metal calcined catalyst having a secondary promoter |
| US9108895B2 (en) | 2012-10-26 | 2015-08-18 | Eastman Chemical Company | Promoted ruthenium catalyst for the improved hydrogenation of carboxylic acids to the corresponding alcohols |
| US8772553B2 (en) | 2012-10-26 | 2014-07-08 | Celanese International Corporation | Hydrogenation reaction conditions for producing ethanol |
| EP2759598A1 (de) * | 2013-01-24 | 2014-07-30 | Evonik Industries AG | Verfahren zur Herstellung von alpha, omega-Alkandiol |
| CN103449971B (zh) * | 2013-08-07 | 2014-12-17 | 青岛俪徕精细化工有限公司 | α,ω-长碳链正构二元醇的生产方法 |
| US10150719B2 (en) | 2013-08-23 | 2018-12-11 | Archer-Daniels-Midland Company | Production of 1,6-hexanediol from adipic acid |
| US9266095B2 (en) | 2014-01-27 | 2016-02-23 | Celanese International Corporation | Hydrogenation catalysts with cobalt and alkaline-earth metal modified supports |
| US9353035B2 (en) | 2014-04-28 | 2016-05-31 | Celanese International Corporation | Process for producing ethanol with zonal catalysts |
| US9073815B1 (en) | 2014-04-28 | 2015-07-07 | Celanese International Corporation | Hydrogenation catalysts comprising a mixed oxide and processes for producing ethanol |
| US9382177B2 (en) | 2014-04-28 | 2016-07-05 | Celanese International Corporation | Hydrogenation catalysts comprising a mixed oxide comprising a promoter metal |
| US9024088B1 (en) | 2014-04-28 | 2015-05-05 | Celanese International Corporation | Hydrogenation catalysts comprising a mixed oxide comprising nickel |
| CN111974388B (zh) * | 2014-05-23 | 2023-10-31 | 三菱化学株式会社 | 负载金属催化剂、负载金属催化剂的保存方法以及醇的制造方法 |
| WO2016122465A1 (en) | 2015-01-27 | 2016-08-04 | Celanese International Corporation | Process for producing ethanol using solid catalysts |
| US9670120B2 (en) | 2015-01-27 | 2017-06-06 | Celanese International Corporation | Process for producing ethanol using a solid catalyst |
| US9540297B2 (en) | 2015-04-27 | 2017-01-10 | Celanese International Corporation | Ruthenium-bismuth mixed oxide hydrogenation catalysts and processes for producing ethanol |
| WO2016175745A1 (en) | 2015-04-27 | 2016-11-03 | Celanese International Corporation | Ruthenium-bismuth mixed oxide hydrogenation catalysts and processes for producing ethanol |
| WO2016175747A1 (en) | 2015-04-27 | 2016-11-03 | Celanese International Corporation | Hydrogenation catalysts comprising a mixed oxide having bismuth and process for producing ethanol |
| US10414858B2 (en) | 2016-04-19 | 2019-09-17 | Regents Of The University Of Minnesota | Methods of forming diol compounds |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE878345C (de) * | 1940-02-07 | 1953-06-01 | Degussa | Katalysator fuer die Oxydation von Ammoniak |
| US3578583A (en) * | 1968-09-10 | 1971-05-11 | Chevron Res | Reforming process with promoted low platinum content catalyst |
| IE34345B1 (en) * | 1969-07-03 | 1975-04-16 | Universal Oil Prod Co | Hydrocarbon conversion process and catalyst therefor |
| FR2102666A5 (enExample) * | 1970-08-14 | 1972-04-07 | Raffinage Cie Francaise | |
| DE2519817A1 (de) | 1975-05-03 | 1976-11-11 | Hoechst Ag | Verfahren zur herstellung von butandiol-(1.4) |
| DE2715667A1 (de) | 1977-04-07 | 1978-10-12 | Hoechst Ag | Verfahren zur herstellung von butandiol-(1.4) |
| DE2715666A1 (de) * | 1977-04-07 | 1978-10-12 | Hoechst Ag | Verfahren zur herstellung von aethylenglykol |
| US4108478A (en) * | 1977-07-05 | 1978-08-22 | Fenix & Scisson, Inc. | Means to prevent relative rotation of threaded together pin and box tool joints |
| US4338221A (en) * | 1981-02-11 | 1982-07-06 | Uop Inc. | Catalyst for the reduction of unsaturated organic acids |
| US4398039A (en) * | 1981-05-18 | 1983-08-09 | The Standard Oil Company | Hydrogenation of carboxylic acids |
| 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 |
| GB8707595D0 (en) * | 1987-03-31 | 1987-05-07 | British Petroleum Co Plc | Chemical process |
| JPH01310738A (ja) * | 1988-06-10 | 1989-12-14 | Toyota Motor Corp | 排ガス浄化用触媒 |
| DD297888A7 (de) * | 1989-12-06 | 1992-01-30 | Leuna-Werke Ag,De | Reformierkatalysator fuer die umwandlung von benzinkohlenwasserstoffen |
| US5254518A (en) * | 1992-07-22 | 1993-10-19 | Exxon Research & Engineering Company | Group IVB oxide addition to noble metal on rare earth modified silica alumina as hydrocarbon conversion catalyst |
-
1997
- 1997-05-16 DE DE19720657A patent/DE19720657A1/de not_active Withdrawn
-
1998
- 1998-05-12 DE DE59806195T patent/DE59806195D1/de not_active Expired - Lifetime
- 1998-05-12 WO PCT/EP1998/002777 patent/WO1998052891A1/de not_active Ceased
- 1998-05-12 US US09/423,876 patent/US6204417B1/en not_active Expired - Lifetime
- 1998-05-12 ES ES98925581T patent/ES2187029T3/es not_active Expired - Lifetime
- 1998-05-12 JP JP54989498A patent/JP4138025B2/ja not_active Expired - Fee Related
- 1998-05-12 CN CN98805932A patent/CN1109009C/zh not_active Expired - Fee Related
- 1998-05-12 EP EP98925581A patent/EP0983219B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2187029T3 (es) | 2003-05-16 |
| US6204417B1 (en) | 2001-03-20 |
| EP0983219A2 (de) | 2000-03-08 |
| EP0983219B1 (de) | 2002-11-06 |
| DE19720657A1 (de) | 1998-11-19 |
| WO1998052891A1 (de) | 1998-11-26 |
| JP2001526670A (ja) | 2001-12-18 |
| CN1109009C (zh) | 2003-05-21 |
| CN1259112A (zh) | 2000-07-05 |
| DE59806195D1 (de) | 2002-12-12 |
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