NO327888B1 - Fremgangsmate for samproduksjon av butan-1,4-diol og tetrahydrofuran - Google Patents
Fremgangsmate for samproduksjon av butan-1,4-diol og tetrahydrofuran Download PDFInfo
- Publication number
- NO327888B1 NO327888B1 NO20022804A NO20022804A NO327888B1 NO 327888 B1 NO327888 B1 NO 327888B1 NO 20022804 A NO20022804 A NO 20022804A NO 20022804 A NO20022804 A NO 20022804A NO 327888 B1 NO327888 B1 NO 327888B1
- Authority
- NO
- Norway
- Prior art keywords
- catalyst
- hydrogenation
- hydrogenation zone
- tetrahydrofuran
- stream
- Prior art date
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 64
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims abstract description 58
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 149
- 239000003054 catalyst Substances 0.000 claims abstract description 133
- 239000000463 material Substances 0.000 claims abstract description 66
- -1 aliphatic diester Chemical class 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000006227 byproduct Substances 0.000 claims abstract description 23
- NMPJHMFXHISVBR-UHFFFAOYSA-N 4-(oxolan-2-yloxy)butan-1-ol Chemical compound OCCCCOC1CCCO1 NMPJHMFXHISVBR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 230000002378 acidificating effect Effects 0.000 claims abstract description 22
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims abstract description 16
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims abstract description 16
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 239000012467 final product Substances 0.000 claims abstract description 14
- 239000013067 intermediate product Substances 0.000 claims abstract description 14
- 150000004292 cyclic ethers Chemical class 0.000 claims abstract description 7
- 150000002009 diols Chemical class 0.000 claims abstract description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 43
- 239000011148 porous material Substances 0.000 claims description 42
- 239000007788 liquid Substances 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 21
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims description 20
- 238000009826 distribution Methods 0.000 claims description 20
- 229910052748 manganese Inorganic materials 0.000 claims description 14
- 239000011572 manganese Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 7
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 5
- LOLKAJARZKDJTD-UHFFFAOYSA-N 4-Ethoxy-4-oxobutanoic acid Chemical compound CCOC(=O)CCC(O)=O LOLKAJARZKDJTD-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims description 4
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 3
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 claims description 2
- JDRMYOQETPMYQX-UHFFFAOYSA-M 4-methoxy-4-oxobutanoate Chemical compound COC(=O)CCC([O-])=O JDRMYOQETPMYQX-UHFFFAOYSA-M 0.000 claims description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000005751 Copper oxide Substances 0.000 claims description 2
- RHQKKJPJCHGKQO-UHFFFAOYSA-N [Cu+2].[O-][Cr]([O-])=O Chemical class [Cu+2].[O-][Cr]([O-])=O RHQKKJPJCHGKQO-UHFFFAOYSA-N 0.000 claims description 2
- JDRMYOQETPMYQX-UHFFFAOYSA-N butanedioic acid monomethyl ester Natural products COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910000431 copper oxide Inorganic materials 0.000 claims description 2
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 claims description 2
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 claims description 2
- 229960004419 dimethyl fumarate Drugs 0.000 claims description 2
- 229940074369 monoethyl fumarate Drugs 0.000 claims description 2
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims description 2
- 229940005650 monomethyl fumarate Drugs 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 24
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 150000002596 lactones Chemical class 0.000 abstract description 3
- 150000005690 diesters Chemical class 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 230000000875 corresponding effect Effects 0.000 description 15
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 15
- 238000005516 engineering process Methods 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000032050 esterification Effects 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000007655 standard test method Methods 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 101100048480 Vaccinia virus (strain Western Reserve) UNG gene Proteins 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/177—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99310003A EP1108702A1 (en) | 1999-12-13 | 1999-12-13 | Process for the co-production of aliphatic diols and cyclic ethers |
| PCT/GB2000/004758 WO2001044148A1 (en) | 1999-12-13 | 2000-12-12 | Process for the co-production of aliphatic diols and cyclic ethers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20022804D0 NO20022804D0 (no) | 2002-06-12 |
| NO20022804L NO20022804L (no) | 2002-06-27 |
| NO327888B1 true NO327888B1 (no) | 2009-10-12 |
Family
ID=8241808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20022804A NO327888B1 (no) | 1999-12-13 | 2002-06-12 | Fremgangsmate for samproduksjon av butan-1,4-diol og tetrahydrofuran |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6844452B2 (ko) |
| EP (2) | EP1108702A1 (ko) |
| JP (1) | JP4892152B2 (ko) |
| KR (1) | KR100610723B1 (ko) |
| CN (1) | CN1188378C (ko) |
| AT (1) | ATE276989T1 (ko) |
| AU (1) | AU783452B2 (ko) |
| BR (1) | BR0016363B1 (ko) |
| CA (1) | CA2394270C (ko) |
| DE (1) | DE60014155T2 (ko) |
| ES (1) | ES2225286T3 (ko) |
| GC (1) | GC0000158A (ko) |
| MX (1) | MXPA02005880A (ko) |
| MY (1) | MY137657A (ko) |
| NO (1) | NO327888B1 (ko) |
| TW (1) | TW539663B (ko) |
| WO (1) | WO2001044148A1 (ko) |
| ZA (1) | ZA200204292B (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10061553A1 (de) * | 2000-12-11 | 2002-06-13 | Basf Ag | Poröser Katalysator für die Hydrierung von Maleinsäureanhydrid zu Tetrahydrofuran |
| GB0117090D0 (en) * | 2001-07-12 | 2001-09-05 | Kvaerner Process Tech Ltd | Process |
| GB2401804B (en) * | 2003-05-19 | 2006-09-27 | Phoenix Chemicals Ltd | Reactor |
| GB0329152D0 (en) * | 2003-12-16 | 2004-01-21 | Davy Process Techn Ltd | Process |
| GB0421928D0 (en) * | 2004-10-01 | 2004-11-03 | Davy Process Techn Ltd | Process |
| US8094630B2 (en) * | 2005-12-16 | 2012-01-10 | Airvana Network Solutions, Inc. | Radio frequency dragging prevention |
| GB0803663D0 (en) * | 2008-02-28 | 2008-04-09 | Davy Process Techn Ltd | Process |
| US20110112326A1 (en) * | 2009-08-07 | 2011-05-12 | Jean-Paul Lange | Process for hydrogenation |
| WO2013005750A1 (ja) * | 2011-07-04 | 2013-01-10 | 三菱化学株式会社 | テトラヒドロフランの製造方法 |
| GB201119871D0 (en) * | 2011-11-17 | 2011-12-28 | Davy Process Techn Ltd | Process |
| EP2782893B1 (en) | 2011-11-25 | 2017-08-23 | Conser SPA | Process for producing 1,4-butanediol, gamma-butyrolactone and tetrahydrofuran by hydrogenating dialkyl maleate in mixed liquid/vapor phase |
| WO2016113758A1 (en) | 2015-01-15 | 2016-07-21 | Council Of Scientific & Industrial Research | Catalytic hydrogenation process for the synthesis of terminal diols from terminal dialkyl aliphatic esters |
| GB201615385D0 (en) * | 2016-09-09 | 2016-10-26 | Intensichem Group Ltd | Hydrogenation process |
| CN111018669B (zh) * | 2018-10-09 | 2022-10-04 | 中国石油化工股份有限公司 | 一种1,4-丁二醇连续化制备方法 |
| EP4073052A1 (de) * | 2019-12-10 | 2022-10-19 | Basf Se | Verfahren zur herstellung von 1,4-butandiol, gamma-butyrolacton und tetrahydrofuran in der gasphase unter vermeidung von polymeren ablagerungen |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4032458A (en) * | 1975-08-08 | 1977-06-28 | Petro-Tex Chemical Corporation | Production of 1,4-butanediol |
| GB1577633A (en) * | 1976-12-17 | 1980-10-29 | Degussa | Acyl derivatives of hellebrigenin |
| JPS5432409A (en) * | 1977-08-03 | 1979-03-09 | Mitsubishi Chem Ind Ltd | Preparation of ciol and cyclic ether |
| JPS5845410B2 (ja) * | 1978-12-12 | 1983-10-08 | ジェイエスアール株式会社 | テトラヒドロフラン及び１，４↓−ブタンジオ−ルの製造方法 |
| GB8331793D0 (en) * | 1983-11-29 | 1984-01-04 | Davy Mckee Ltd | Process |
| WO1986003189A1 (en) * | 1984-11-21 | 1986-06-05 | Davy Mckee (London) Limited | Process for the production of butane-1,4-diol |
| GB8618888D0 (en) * | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| US4810807A (en) * | 1987-10-13 | 1989-03-07 | The Standard Oil Company | Hydrogenation of maleic anhydride to tetrahydrofuran |
| GB8917864D0 (en) * | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| GB8917862D0 (en) * | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| GB9324753D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
-
1999
- 1999-12-13 EP EP99310003A patent/EP1108702A1/en not_active Withdrawn
-
2000
- 2000-12-12 US US10/149,199 patent/US6844452B2/en not_active Expired - Lifetime
- 2000-12-12 EP EP00985546A patent/EP1237833B1/en not_active Expired - Lifetime
- 2000-12-12 ES ES00985546T patent/ES2225286T3/es not_active Expired - Lifetime
- 2000-12-12 DE DE60014155T patent/DE60014155T2/de not_active Expired - Lifetime
- 2000-12-12 AT AT00985546T patent/ATE276989T1/de not_active IP Right Cessation
- 2000-12-12 MX MXPA02005880A patent/MXPA02005880A/es active IP Right Grant
- 2000-12-12 WO PCT/GB2000/004758 patent/WO2001044148A1/en active IP Right Grant
- 2000-12-12 CN CNB008181225A patent/CN1188378C/zh not_active Expired - Fee Related
- 2000-12-12 BR BRPI0016363-5B1A patent/BR0016363B1/pt not_active IP Right Cessation
- 2000-12-12 CA CA2394270A patent/CA2394270C/en not_active Expired - Fee Related
- 2000-12-12 JP JP2001545238A patent/JP4892152B2/ja not_active Expired - Fee Related
- 2000-12-12 AU AU21958/01A patent/AU783452B2/en not_active Ceased
- 2000-12-12 KR KR1020027007563A patent/KR100610723B1/ko not_active IP Right Cessation
- 2000-12-13 MY MYPI20005843A patent/MY137657A/en unknown
- 2000-12-13 GC GCP20001098 patent/GC0000158A/xx active
-
2001
- 2001-01-08 TW TW090100359A patent/TW539663B/zh not_active IP Right Cessation
-
2002
- 2002-05-29 ZA ZA200204292A patent/ZA200204292B/en unknown
- 2002-06-12 NO NO20022804A patent/NO327888B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60014155D1 (de) | 2004-10-28 |
| ZA200204292B (en) | 2003-05-29 |
| EP1237833B1 (en) | 2004-09-22 |
| CA2394270C (en) | 2010-02-16 |
| TW539663B (en) | 2003-07-01 |
| BR0016363B1 (pt) | 2013-11-05 |
| MXPA02005880A (es) | 2002-10-23 |
| KR20020062337A (ko) | 2002-07-25 |
| DE60014155T2 (de) | 2005-02-03 |
| ATE276989T1 (de) | 2004-10-15 |
| JP2003517028A (ja) | 2003-05-20 |
| MY137657A (en) | 2009-02-27 |
| WO2001044148A1 (en) | 2001-06-21 |
| CA2394270A1 (en) | 2001-06-21 |
| NO20022804D0 (no) | 2002-06-12 |
| GC0000158A (en) | 2005-06-29 |
| CN1188378C (zh) | 2005-02-09 |
| AU2195801A (en) | 2001-06-25 |
| JP4892152B2 (ja) | 2012-03-07 |
| CN1414934A (zh) | 2003-04-30 |
| EP1108702A1 (en) | 2001-06-20 |
| NO20022804L (no) | 2002-06-27 |
| BR0016363A (pt) | 2002-10-01 |
| AU783452B2 (en) | 2005-10-27 |
| KR100610723B1 (ko) | 2006-08-09 |
| EP1237833A1 (en) | 2002-09-11 |
| US6844452B2 (en) | 2005-01-18 |
| US20030100777A1 (en) | 2003-05-29 |
| ES2225286T3 (es) | 2005-03-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4889860B2 (ja) | 酢酸エチルの製造用プロセス | |
| NO327888B1 (no) | Fremgangsmate for samproduksjon av butan-1,4-diol og tetrahydrofuran | |
| CA2345992C (en) | Process for recovery of ethyl acetate | |
| EP0656339B1 (en) | Process for the production of cyclohexanedimethanol, with preponderance of the trans-isomer | |
| EP1117630A1 (en) | Process for purification of alkyl alkanoate | |
| EP0656336A1 (en) | Process for the production of hydroxy compounds by hydrogenation of oxygenates | |
| KR101984335B1 (ko) | 1,4-부탄디올을 포함하는 스트림의 정제 방법 | |
| US5414159A (en) | Process | |
| US7598404B2 (en) | Process for the production of ethers | |
| NO328297B1 (no) | Fremgangsmate til fremstilling av etere, typisk THF | |
| US9975828B2 (en) | Process for producing ethanol | |
| US5395986A (en) | Process for the production of cyclohexanedimethanol | |
| NO327782B1 (no) | Fremgangsmate for simultan fremstilling av maleinsyreanhydrid og dets hydrogenerte derivater | |
| MXPA94009271A (en) | Process for the production of 1,4-cyclohexanedimethanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |