ZA200605821B - Process for the production of ethers - Google Patents
Process for the production of ethers Download PDFInfo
- Publication number
- ZA200605821B ZA200605821B ZA200605821A ZA200605821A ZA200605821B ZA 200605821 B ZA200605821 B ZA 200605821B ZA 200605821 A ZA200605821 A ZA 200605821A ZA 200605821 A ZA200605821 A ZA 200605821A ZA 200605821 B ZA200605821 B ZA 200605821B
- Authority
- ZA
- South Africa
- Prior art keywords
- zone
- process according
- hydrogen
- feed material
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 72
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 150000002170 ethers Chemical class 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims description 83
- 239000003054 catalyst Substances 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 73
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 62
- 239000000463 material Substances 0.000 claims description 44
- 239000000047 product Substances 0.000 claims description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- 239000007789 gas Substances 0.000 claims description 37
- 238000009834 vaporization Methods 0.000 claims description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 31
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims description 27
- 150000008064 anhydrides Chemical class 0.000 claims description 22
- 239000006227 byproduct Substances 0.000 claims description 19
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 150000002596 lactones Chemical class 0.000 claims description 16
- 150000002009 diols Chemical class 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 230000032050 esterification Effects 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 3
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 2
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 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
- 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
- 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 1
- 229940074369 monoethyl fumarate Drugs 0.000 claims 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 38
- 238000005984 hydrogenation reaction Methods 0.000 description 26
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000007670 refining Methods 0.000 description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 238000007327 hydrogenolysis reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229930188620 butyrolactone Natural products 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 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
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
- 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
- 230000008901 benefit Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- 239000005751 Copper oxide Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl maleate Chemical compound 0.000 description 3
- 229910000431 copper oxide Inorganic materials 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- NMPJHMFXHISVBR-UHFFFAOYSA-N 4-(oxolan-2-yloxy)butan-1-ol Chemical compound OCCCCOC1CCCO1 NMPJHMFXHISVBR-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-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
- 230000002378 acidificating effect Effects 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
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 101100048480 Vaccinia virus (strain Western Reserve) UNG gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- WERYXYBDKMZEQL-CQDYUVAPSA-N butane-1,4-diol Chemical group O[13CH2]CC[13CH2]O WERYXYBDKMZEQL-CQDYUVAPSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003889 chemical engineering Methods 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
- 238000007796 conventional method Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0329152.3A GB0329152D0 (en) | 2003-12-16 | 2003-12-16 | Process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605821B true ZA200605821B (en) | 2008-05-28 |
Family
ID=30471165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605821A ZA200605821B (en) | 2003-12-16 | 2004-12-01 | Process for the production of ethers |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7598404B2 (pt) |
| EP (1) | EP1694661B1 (pt) |
| JP (1) | JP5013876B2 (pt) |
| KR (1) | KR101144761B1 (pt) |
| CN (1) | CN100577654C (pt) |
| AR (1) | AR047147A1 (pt) |
| AT (1) | ATE465155T1 (pt) |
| AU (1) | AU2004299317B2 (pt) |
| BR (1) | BRPI0417625B1 (pt) |
| CA (1) | CA2548372C (pt) |
| DE (1) | DE602004026773D1 (pt) |
| EA (1) | EA010589B1 (pt) |
| ES (1) | ES2344565T3 (pt) |
| GB (1) | GB0329152D0 (pt) |
| MX (1) | MXPA06006780A (pt) |
| MY (1) | MY143519A (pt) |
| NO (1) | NO20063214L (pt) |
| TW (1) | TWI338005B (pt) |
| WO (1) | WO2005058855A1 (pt) |
| ZA (1) | ZA200605821B (pt) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0421928D0 (en) | 2004-10-01 | 2004-11-03 | Davy Process Techn Ltd | Process |
| GB0803663D0 (en) * | 2008-02-28 | 2008-04-09 | Davy Process Techn Ltd | Process |
| CN102190582B (zh) * | 2010-03-19 | 2014-06-18 | 上海焦化有限公司 | 一种同时生产丁二酸二甲酯和1，4-丁二醇的方法 |
| MY157438A (en) | 2010-09-24 | 2016-06-15 | Basf Se | Process for the production of tetrahydrofuran |
| US9186599B2 (en) | 2010-09-24 | 2015-11-17 | Basf Se | Process for isolating tetrahydrofuran |
| CN102001939B (zh) * | 2010-10-26 | 2013-08-14 | 中国科学院山西煤炭化学研究所 | 一种丁二酸二羧酸酯的制备方法 |
| WO2013076747A1 (en) | 2011-11-25 | 2013-05-30 | Conser Spa | Process for producing 1,4- butanediol by hydrogenating dialkyl maleate in mixed liquid/vapor phase |
| US20130296585A1 (en) | 2012-03-30 | 2013-11-07 | Basf Corporation | Catalyst For Tetrahydrofuran Synthesis |
| GB201318175D0 (en) | 2013-10-14 | 2013-11-27 | Johnson Matthey Davy Technologies Ltd | Process |
| WO2021115813A1 (de) | 2019-12-10 | 2021-06-17 | Basf Se | Verfahren zur herstellung von 1,4-butandiol, gamma-butyrolacton und tetrahydrofuran in der gasphase unter vermeidung von polymeren ablagerungen |
| KR20230156824A (ko) | 2021-03-12 | 2023-11-14 | 꼰세르 엣세.삐.아. | 2개의 스테이지들에서 디알킬 말리에이트를 수소화함으로써 디알킬 숙시네이트 및 1,4-부탄디올의 공생산을 위한 공정 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4830272A (pt) * | 1971-08-21 | 1973-04-21 | ||
| JPS5318988B2 (pt) * | 1972-05-26 | 1978-06-17 | ||
| DE2455617C3 (de) * | 1974-11-23 | 1982-03-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Butandiol und/oder Tetrahydrofuran über die Zwischenstufe des γ-Butyrolactons |
| EP0204730A1 (en) | 1984-11-21 | 1986-12-17 | DAVY McKEE (LONDON) LIMITED | Process for the production of butane-1,4-diol |
| US4626604A (en) * | 1985-09-11 | 1986-12-02 | Davy Mckee (London) Limited | Hydrogenation process |
| BE1011698A6 (fr) * | 1998-01-08 | 1999-12-07 | Pantochim Sa | Procede de production de tetrahydrofuranne, de gamma-butyrolactone et de butanediol. |
| BE1011699A6 (fr) * | 1998-01-08 | 1999-12-07 | Pantochim Sa | Procede de production de tetrahydrofuranne et de gamma-butyrolactone. |
| EP1108702A1 (en) * | 1999-12-13 | 2001-06-20 | Kvaerner Process Technology Limited | Process for the co-production of aliphatic diols and cyclic ethers |
| GB0117090D0 (en) * | 2001-07-12 | 2001-09-05 | Kvaerner Process Tech Ltd | Process |
-
2003
- 2003-12-16 GB GBGB0329152.3A patent/GB0329152D0/en not_active Ceased
-
2004
- 2004-11-26 TW TW093136631A patent/TWI338005B/zh not_active IP Right Cessation
- 2004-12-01 ES ES04801255T patent/ES2344565T3/es active Active
- 2004-12-01 MX MXPA06006780A patent/MXPA06006780A/es active IP Right Grant
- 2004-12-01 WO PCT/GB2004/005054 patent/WO2005058855A1/en active Application Filing
- 2004-12-01 CA CA2548372A patent/CA2548372C/en not_active Expired - Fee Related
- 2004-12-01 JP JP2006544534A patent/JP5013876B2/ja not_active Expired - Fee Related
- 2004-12-01 KR KR1020067012060A patent/KR101144761B1/ko not_active IP Right Cessation
- 2004-12-01 BR BRPI0417625-1B1A patent/BRPI0417625B1/pt not_active IP Right Cessation
- 2004-12-01 ZA ZA200605821A patent/ZA200605821B/en unknown
- 2004-12-01 DE DE602004026773T patent/DE602004026773D1/de active Active
- 2004-12-01 AU AU2004299317A patent/AU2004299317B2/en not_active Ceased
- 2004-12-01 US US10/582,370 patent/US7598404B2/en not_active Expired - Fee Related
- 2004-12-01 AT AT04801255T patent/ATE465155T1/de not_active IP Right Cessation
- 2004-12-01 CN CN200480035623A patent/CN100577654C/zh active Active
- 2004-12-01 EA EA200600972A patent/EA010589B1/ru not_active IP Right Cessation
- 2004-12-01 EP EP04801255A patent/EP1694661B1/en not_active Not-in-force
- 2004-12-03 MY MYPI20045021A patent/MY143519A/en unknown
- 2004-12-16 AR ARP040104689A patent/AR047147A1/es active IP Right Grant
-
2006
- 2006-07-11 NO NO20063214A patent/NO20063214L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI338005B (en) | 2011-03-01 |
| BRPI0417625B1 (pt) | 2013-12-03 |
| MXPA06006780A (es) | 2006-08-23 |
| MY143519A (en) | 2011-05-31 |
| ATE465155T1 (de) | 2010-05-15 |
| AU2004299317B2 (en) | 2010-07-22 |
| NO20063214L (no) | 2006-07-11 |
| WO2005058855A1 (en) | 2005-06-30 |
| KR101144761B1 (ko) | 2012-05-10 |
| CA2548372A1 (en) | 2005-06-30 |
| TW200535133A (en) | 2005-11-01 |
| EP1694661A1 (en) | 2006-08-30 |
| JP5013876B2 (ja) | 2012-08-29 |
| ES2344565T3 (es) | 2010-08-31 |
| EA010589B1 (ru) | 2008-10-30 |
| AU2004299317A1 (en) | 2005-06-30 |
| CN100577654C (zh) | 2010-01-06 |
| AR047147A1 (es) | 2006-01-11 |
| CA2548372C (en) | 2012-02-28 |
| BRPI0417625A (pt) | 2007-03-27 |
| GB0329152D0 (en) | 2004-01-21 |
| US20070088169A1 (en) | 2007-04-19 |
| JP2007516978A (ja) | 2007-06-28 |
| DE602004026773D1 (de) | 2010-06-02 |
| CN1890230A (zh) | 2007-01-03 |
| EP1694661B1 (en) | 2010-04-21 |
| EA200600972A1 (ru) | 2006-10-27 |
| US7598404B2 (en) | 2009-10-06 |
| KR20060111584A (ko) | 2006-10-27 |
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