DE4422051A1 - Verfahren zur Herstellung von 1,4-Butandiol - Google Patents
Verfahren zur Herstellung von 1,4-ButandiolInfo
- Publication number
- DE4422051A1 DE4422051A1 DE4422051A DE4422051A DE4422051A1 DE 4422051 A1 DE4422051 A1 DE 4422051A1 DE 4422051 A DE4422051 A DE 4422051A DE 4422051 A DE4422051 A DE 4422051A DE 4422051 A1 DE4422051 A1 DE 4422051A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation catalyst
- net
- viiib
- elements
- butanediol
- 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.)
- Withdrawn
Links
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000008569 process Effects 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 25
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000007935 neutral effect Effects 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- 229910052702 rhenium Inorganic materials 0.000 claims description 20
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 15
- 239000012876 carrier material Substances 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 239000010949 copper Substances 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052707 ruthenium Inorganic materials 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 235000012239 silicon dioxide Nutrition 0.000 claims description 7
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 5
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000010457 zeolite Substances 0.000 claims description 5
- 239000000956 alloy Substances 0.000 claims description 4
- 229910045601 alloy Inorganic materials 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 239000004408 titanium dioxide Substances 0.000 claims description 4
- 241001026509 Kata Species 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 150000002739 metals Chemical class 0.000 description 16
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 7
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 4
- 239000007848 Bronsted acid Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003245 coal Substances 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
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000605059 Bacteroidetes Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- IGDGIZKERQBUNG-UHFFFAOYSA-N [Cu].[Ba] Chemical compound [Cu].[Ba] IGDGIZKERQBUNG-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- -1 aluminum silicates Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 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
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010285 flame spraying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical compound P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003281 rhenium Chemical class 0.000 description 1
- 150000003282 rhenium compounds Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Luminescent Compositions (AREA)
- Polyesters Or Polycarbonates (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Photoreceptors In Electrophotography (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4422051A DE4422051A1 (de) | 1994-06-27 | 1994-06-27 | Verfahren zur Herstellung von 1,4-Butandiol |
| AU27930/95A AU2793095A (en) | 1994-06-27 | 1995-06-16 | Method of producing 1,4-butanediol |
| US08/765,577 US5945571A (en) | 1994-06-27 | 1995-06-16 | Preparation of 1,4-butanediol |
| EP95923336A EP0767769B1 (de) | 1994-06-27 | 1995-06-16 | Verfahren zur herstellung von 1,4-butandiol |
| PCT/EP1995/002335 WO1996000203A1 (de) | 1994-06-27 | 1995-06-16 | Verfahren zur herstellung von 1,4-butandiol |
| JP50276096A JP3803372B2 (ja) | 1994-06-27 | 1995-06-16 | １，４−ブタンジオールの製造方法 |
| AT95923336T ATE171930T1 (de) | 1994-06-27 | 1995-06-16 | Verfahren zur herstellung von 1,4-butandiol |
| DE59503861T DE59503861D1 (de) | 1994-06-27 | 1995-06-16 | Verfahren zur herstellung von 1,4-butandiol |
| RU97101182A RU2147298C1 (ru) | 1994-06-27 | 1995-06-16 | Способ получения 1,4-бутандиола |
| CN95194332A CN1071296C (zh) | 1994-06-27 | 1995-06-16 | 1,4-丁二醇的制备方法 |
| ES95923336T ES2124561T3 (es) | 1994-06-27 | 1995-06-16 | Procedimiento para la obtencion de 1,4-butanodiol. |
| CA002194097A CA2194097C (en) | 1994-06-27 | 1995-06-16 | Preparation of 1,4-butanediol |
| KR1019960707490A KR100365462B1 (ko) | 1994-06-27 | 1995-06-16 | 1,4-부탄디올의제조방법 |
| TW084106391A TW300216B (enExample) | 1994-06-27 | 1995-06-21 | |
| FI965228A FI112469B (fi) | 1994-06-27 | 1996-12-27 | Menetelmä 1,4-butaanidiolin valmistamiseksi |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4422051A DE4422051A1 (de) | 1994-06-27 | 1994-06-27 | Verfahren zur Herstellung von 1,4-Butandiol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4422051A1 true DE4422051A1 (de) | 1996-01-04 |
Family
ID=6521360
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4422051A Withdrawn DE4422051A1 (de) | 1994-06-27 | 1994-06-27 | Verfahren zur Herstellung von 1,4-Butandiol |
| DE59503861T Expired - Fee Related DE59503861D1 (de) | 1994-06-27 | 1995-06-16 | Verfahren zur herstellung von 1,4-butandiol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59503861T Expired - Fee Related DE59503861D1 (de) | 1994-06-27 | 1995-06-16 | Verfahren zur herstellung von 1,4-butandiol |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5945571A (enExample) |
| EP (1) | EP0767769B1 (enExample) |
| JP (1) | JP3803372B2 (enExample) |
| KR (1) | KR100365462B1 (enExample) |
| CN (1) | CN1071296C (enExample) |
| AT (1) | ATE171930T1 (enExample) |
| AU (1) | AU2793095A (enExample) |
| CA (1) | CA2194097C (enExample) |
| DE (2) | DE4422051A1 (enExample) |
| ES (1) | ES2124561T3 (enExample) |
| FI (1) | FI112469B (enExample) |
| RU (1) | RU2147298C1 (enExample) |
| TW (1) | TW300216B (enExample) |
| WO (1) | WO1996000203A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0915075A1 (de) * | 1997-11-07 | 1999-05-12 | Degussa Aktiengesellschaft | Verfahren zur intermolekularen Veretherung und zur Etherspaltung |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4422051A1 (de) * | 1994-06-27 | 1996-01-04 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol |
| DE10128205A1 (de) * | 2001-06-11 | 2002-12-12 | Basf Ag | Ruthenium-Katalysatoren |
| JP5577152B2 (ja) * | 2010-05-24 | 2014-08-20 | 本田技研工業株式会社 | 歩行補助装置 |
| WO2015058990A1 (de) * | 2013-10-23 | 2015-04-30 | Basf Se | Verfahren zur herstellung von 1,4-butandiol mit einer apha-farbzahl von weniger als 30 |
| RU2679639C2 (ru) * | 2014-12-04 | 2019-02-12 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения 1,4-бутандиола и тетрагидрофурана из фурана |
| BR112017021642B1 (pt) * | 2015-04-09 | 2020-12-01 | Shell Internationale Research Maatschappij B.V. | processo para a produção de 1,4-butanodiol e tetraidrofurano a partir de furano |
| JP6859657B2 (ja) * | 2016-10-19 | 2021-04-14 | 三菱ケミカル株式会社 | ジオール化合物の製造方法 |
| CN121895546B (zh) * | 2026-03-26 | 2026-06-30 | 上海金发科技发展有限公司 | 一种1,4-丁二醇组合物及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1214648A1 (ru) * | 1983-04-01 | 1986-02-28 | Предприятие П/Я А-7531 | Способ получени 1,4-бутандиола |
| US4475004A (en) * | 1983-12-21 | 1984-10-02 | Ethyl Corporation | Preparation of alkanediols |
| US4476332A (en) * | 1983-12-21 | 1984-10-09 | Ethyl Corporation | Preparation of alkanediols |
| GB8809860D0 (en) * | 1988-04-26 | 1988-06-02 | Ciba Geigy Ag | Process for production of polypeptides |
| US4859801A (en) * | 1988-05-26 | 1989-08-22 | E. I. Du Pont De Nemours And Company | Synthesis of mixtures of butanediols |
| US5254701A (en) * | 1991-05-20 | 1993-10-19 | Eastman Kodak Company | Process for the production of mixtures of 2-hydroxytetrahydrofuran and 4-hydroxybutanal |
| DE4325753A1 (de) * | 1993-07-31 | 1995-02-02 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol |
| DE4422051A1 (de) * | 1994-06-27 | 1996-01-04 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol |
-
1994
- 1994-06-27 DE DE4422051A patent/DE4422051A1/de not_active Withdrawn
-
1995
- 1995-06-16 CN CN95194332A patent/CN1071296C/zh not_active Expired - Fee Related
- 1995-06-16 AT AT95923336T patent/ATE171930T1/de not_active IP Right Cessation
- 1995-06-16 AU AU27930/95A patent/AU2793095A/en not_active Abandoned
- 1995-06-16 JP JP50276096A patent/JP3803372B2/ja not_active Expired - Fee Related
- 1995-06-16 CA CA002194097A patent/CA2194097C/en not_active Expired - Fee Related
- 1995-06-16 RU RU97101182A patent/RU2147298C1/ru not_active IP Right Cessation
- 1995-06-16 US US08/765,577 patent/US5945571A/en not_active Expired - Fee Related
- 1995-06-16 WO PCT/EP1995/002335 patent/WO1996000203A1/de not_active Ceased
- 1995-06-16 DE DE59503861T patent/DE59503861D1/de not_active Expired - Fee Related
- 1995-06-16 KR KR1019960707490A patent/KR100365462B1/ko not_active Expired - Fee Related
- 1995-06-16 EP EP95923336A patent/EP0767769B1/de not_active Expired - Lifetime
- 1995-06-16 ES ES95923336T patent/ES2124561T3/es not_active Expired - Lifetime
- 1995-06-21 TW TW084106391A patent/TW300216B/zh active
-
1996
- 1996-12-27 FI FI965228A patent/FI112469B/fi active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0915075A1 (de) * | 1997-11-07 | 1999-05-12 | Degussa Aktiengesellschaft | Verfahren zur intermolekularen Veretherung und zur Etherspaltung |
| US6218580B1 (en) | 1997-11-07 | 2001-04-17 | Degussa-Huls Aktiengesellschaft | Process for intermolecular etherification and ether cleavage |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10502062A (ja) | 1998-02-24 |
| JP3803372B2 (ja) | 2006-08-02 |
| ES2124561T3 (es) | 1999-02-01 |
| EP0767769A1 (de) | 1997-04-16 |
| RU2147298C1 (ru) | 2000-04-10 |
| ATE171930T1 (de) | 1998-10-15 |
| FI965228A0 (fi) | 1996-12-27 |
| WO1996000203A1 (de) | 1996-01-04 |
| FI112469B (fi) | 2003-12-15 |
| TW300216B (enExample) | 1997-03-11 |
| CN1154100A (zh) | 1997-07-09 |
| CA2194097C (en) | 2005-08-02 |
| EP0767769B1 (de) | 1998-10-07 |
| FI965228L (fi) | 1997-02-26 |
| AU2793095A (en) | 1996-01-19 |
| US5945571A (en) | 1999-08-31 |
| CA2194097A1 (en) | 1996-01-04 |
| DE59503861D1 (de) | 1998-11-12 |
| KR100365462B1 (ko) | 2003-05-22 |
| CN1071296C (zh) | 2001-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0815097B1 (de) | Verfahren zur Herstellung von 1,4-Butandiol und Tetrahydrofuran aus Furan | |
| EP2051972B1 (de) | Verfahren zur einstufigen herstellung von 2-methyltetrahydrofuran aus furfural an zwei katalysatoren in strukturierter schüttung | |
| DE2519817A1 (de) | Verfahren zur herstellung von butandiol-(1.4) | |
| DE19750532A1 (de) | Verfahren zur Herstellung von 1,6-Hexandiol und 6-Hydroxycapronsäure bzw. deren Estern | |
| EP1080061B1 (de) | Verfahren zur herstellung von gemischen aus 1,4-butandiol, tetrahydrofuran und gamma-butyrolacton | |
| DE2605107B2 (de) | Verfahren zur Herstellung von Diolen durch katalytische Hydrierung entsprechenden Dikarbonsäure | |
| EP2089370A1 (de) | Verfahren zur einstufigen herstellung von 2-methyltetrahydrofuran aus furfural an einem katalysator | |
| EP0711267B1 (de) | Verfahren zur herstellung von 1,4-butandiol | |
| EP0767769B1 (de) | Verfahren zur herstellung von 1,4-butandiol | |
| DE2905507A1 (de) | Substituierte aminoaromatische acetylene und verfahren zu ihrer herstellung | |
| EP0729462B1 (de) | Verfahren zur herstellung von gamma-butyrolacton | |
| EP1208094B1 (de) | Verfahren zur herstellung von gamma-butyrolacton | |
| DE68901742T2 (de) | Verfahren zur herstellung von gamma-butyrolacton. | |
| WO1998005631A1 (de) | Verfahren zur herstellung von 6-aminocapronitril | |
| DE19622497A1 (de) | Verfahren zur Herstellung von Tetrahydrofuran aus Dialkoxybutenen | |
| DE1468779C3 (enExample) | ||
| DE10052803A1 (de) | Verfahren zur Herstellung von Mintlacton | |
| EP0794166B1 (de) | Verfahren zur Herstellung von Hydroxymethylcyclopropan | |
| DE4304756C1 (de) | Verfahren zur Darstellung von Salzen, chiraler, alpha-sauerstoffunktionalisierter Carbonsäuren | |
| DE2434991A1 (de) | Verfahren zur herstellung von butandiol-(1,4) | |
| DE2339343C3 (de) | Verfahren zur Herstellung von gamma-Butyrolacton | |
| DE4431743A1 (de) | Verfahren zur Herstellung von 1,4-Butandiol | |
| DD248113A1 (de) | Verfahren zur herstellung von butandiol-1,4 | |
| DD203714A5 (de) | Verfahren zur selektiven spaltung von polyalkylenglykolen | |
| DD265395A1 (de) | Verfahren zur herstellung von butandiol-1,4 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |