WO2003104175A1 - Zweistufiges verfahren zur herstellung von butandiol mit zwischenabtrennung von bernsteinsäureanhydrid - Google Patents
Zweistufiges verfahren zur herstellung von butandiol mit zwischenabtrennung von bernsteinsäureanhydrid Download PDFInfo
- Publication number
- WO2003104175A1 WO2003104175A1 PCT/EP2003/006100 EP0306100W WO03104175A1 WO 2003104175 A1 WO2003104175 A1 WO 2003104175A1 EP 0306100 W EP0306100 W EP 0306100W WO 03104175 A1 WO03104175 A1 WO 03104175A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrogenation
- catalyst
- reactor
- stage
- phthalate
- Prior art date
Links
- 238000000926 separation method Methods 0.000 title claims abstract description 9
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229940014800 succinic anhydride Drugs 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 18
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 title description 73
- 239000003054 catalyst Substances 0.000 claims abstract description 173
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 132
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 85
- 238000000034 method Methods 0.000 claims abstract description 76
- 239000000047 product Substances 0.000 claims abstract description 28
- 239000006227 byproduct Substances 0.000 claims abstract description 15
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 6
- 239000013067 intermediate product Substances 0.000 claims abstract description 5
- 239000007789 gas Substances 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 45
- 230000008569 process Effects 0.000 claims description 45
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- 239000010949 copper Substances 0.000 claims description 28
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- 239000007858 starting material Substances 0.000 claims description 27
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 10
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- 238000009835 boiling Methods 0.000 claims description 8
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- 230000002829 reductive effect Effects 0.000 claims description 8
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 7
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 239000000543 intermediate Substances 0.000 claims description 6
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- 125000005498 phthalate group Chemical class 0.000 claims description 5
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- 125000003118 aryl group Chemical group 0.000 claims description 3
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- LMIDQHXGBYBMLR-UHFFFAOYSA-N 1,4-dimethylcyclohexane-1,4-dicarboxylic acid Chemical compound OC(=O)C1(C)CCC(C)(C(O)=O)CC1 LMIDQHXGBYBMLR-UHFFFAOYSA-N 0.000 claims description 2
- KTZXIELULAGNJC-UHFFFAOYSA-N 1,4-dimethylnaphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C(C)=C(C(O)=O)C(C(O)=O)=C(C)C2=C1 KTZXIELULAGNJC-UHFFFAOYSA-N 0.000 claims description 2
- CAZKHBNCZSWFFM-UHFFFAOYSA-N 2-undecoxycarbonylbenzoic acid Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(O)=O CAZKHBNCZSWFFM-UHFFFAOYSA-N 0.000 claims description 2
- QWDBCIAVABMJPP-UHFFFAOYSA-N Diisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)C QWDBCIAVABMJPP-UHFFFAOYSA-N 0.000 claims description 2
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- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 2
- 229960001826 dimethylphthalate Drugs 0.000 claims description 2
- MQHNKCZKNAJROC-UHFFFAOYSA-N dipropyl phthalate Chemical group CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 claims description 2
- QQVHEQUEHCEAKS-UHFFFAOYSA-N diundecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCC QQVHEQUEHCEAKS-UHFFFAOYSA-N 0.000 claims description 2
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- 230000004048 modification Effects 0.000 claims description 2
- CXJOEMLCEGZVPL-UHFFFAOYSA-N monoisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(O)=O CXJOEMLCEGZVPL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
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- 238000004064 recycling Methods 0.000 claims description 2
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000007792 gaseous phase Substances 0.000 abstract 3
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
- 239000011651 chromium Substances 0.000 description 28
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- 239000012071 phase Substances 0.000 description 17
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- 239000011787 zinc oxide Substances 0.000 description 13
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- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052728 basic metal Inorganic materials 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
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- RNCXCPUOPDATPU-UHFFFAOYSA-N chromium(3+) oxocopper oxygen(2-) Chemical compound [O-2].[Cr+3].[Cu]=O.[O-2].[O-2].[Cr+3] RNCXCPUOPDATPU-UHFFFAOYSA-N 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WCCJDBZJUYKDBF-UHFFFAOYSA-N copper silicon Chemical compound [Si].[Cu] WCCJDBZJUYKDBF-UHFFFAOYSA-N 0.000 description 1
- VODBHXZOIQDDST-UHFFFAOYSA-N copper zinc oxygen(2-) Chemical compound [O--].[O--].[Cu++].[Zn++] VODBHXZOIQDDST-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 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
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052726 zirconium 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
- C07C29/132—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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/516,922 US7271299B2 (en) | 2002-06-11 | 2003-06-11 | Two-stage method for producing butanediol with intermediated separation of succinic anhydride |
JP2004511245A JP2005534657A (ja) | 2002-06-11 | 2003-06-11 | 無水コハク酸の中間分離を行いブタンジオールを2工程で製造する方法 |
KR20047020099A KR20050007603A (ko) | 2002-06-11 | 2003-06-11 | 숙신산 무수물의 중간 분리를 포함하는 부탄디올의 2 단계제조 방법 |
EP03757057A EP1515933A1 (de) | 2002-06-11 | 2003-06-11 | Zweistufiges verfahren zur herstellung von butandiol mit zwischenabtrennung von bernsteinsäureanhydrid |
AU2003242665A AU2003242665A1 (en) | 2002-06-11 | 2003-06-11 | Two-stage method for producing butane diol with intermediate separation of succinic anhydride |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10225929.1 | 2002-06-11 | ||
DE10225929A DE10225929A1 (de) | 2002-06-11 | 2002-06-11 | Zweistufiges Verfahren zur Herstellung von Butandiol mit Zwischenabtrennung von Bernsteinsäureanhydrid |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003104175A1 true WO2003104175A1 (de) | 2003-12-18 |
Family
ID=29594385
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/006100 WO2003104175A1 (de) | 2002-06-11 | 2003-06-11 | Zweistufiges verfahren zur herstellung von butandiol mit zwischenabtrennung von bernsteinsäureanhydrid |
Country Status (8)
Country | Link |
---|---|
US (1) | US7271299B2 (de) |
EP (1) | EP1515933A1 (de) |
JP (1) | JP2005534657A (de) |
KR (1) | KR20050007603A (de) |
CN (1) | CN100463889C (de) |
AU (1) | AU2003242665A1 (de) |
DE (1) | DE10225929A1 (de) |
WO (1) | WO2003104175A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010007327A2 (fr) * | 2008-07-18 | 2010-01-21 | Arkema France | Fabrication d'anhydride maleique a partir de matieres renouvelables, anhydride maleique obtenu et utilisations |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10357715A1 (de) * | 2003-12-09 | 2005-07-14 | Basf Ag | Verfahren zur Herstellung von definierten Gemischen aus THF, BDO und GBL durch Gasphasenhydierung |
BRPI0913770B1 (pt) * | 2008-12-18 | 2017-09-12 | China Petroleum & Chemical Corporation | Process for the production of ethylene glycol from an oxalate |
WO2011022511A2 (en) * | 2009-08-19 | 2011-02-24 | Strategic Enzyme Applications, Inc. | Methods of reducing lignin and products thereof |
GB201318175D0 (en) | 2013-10-14 | 2013-11-27 | Johnson Matthey Davy Technologies Ltd | Process |
CN104368358B (zh) * | 2014-10-11 | 2017-06-06 | 中国科学院青岛生物能源与过程研究所 | 一种适用于琥珀酸加氢反应的催化剂及其制备和加氢反应方法 |
ES2730109T3 (es) * | 2015-01-09 | 2019-11-08 | Basf Se | Procedimiento para la preparación de tetrahidrofurano, 1,4-butanodiol o gamma-butirolactona |
CN114904584B (zh) * | 2022-06-21 | 2024-04-12 | 万华化学集团股份有限公司 | 一种丁二酸二烷基酯加氢生产1,4-丁二醇的催化剂及其制备方法和应用 |
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WO1997043234A1 (en) * | 1996-05-15 | 1997-11-20 | Kvaerner Process Technology Limited | Process for preparing gamma-butyrolactone, butane-1,4-diol and tetrahydrofuran |
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-
2002
- 2002-06-11 DE DE10225929A patent/DE10225929A1/de not_active Withdrawn
-
2003
- 2003-06-11 WO PCT/EP2003/006100 patent/WO2003104175A1/de active Application Filing
- 2003-06-11 CN CNB038165333A patent/CN100463889C/zh not_active Expired - Fee Related
- 2003-06-11 US US10/516,922 patent/US7271299B2/en not_active Expired - Fee Related
- 2003-06-11 AU AU2003242665A patent/AU2003242665A1/en not_active Abandoned
- 2003-06-11 EP EP03757057A patent/EP1515933A1/de not_active Withdrawn
- 2003-06-11 KR KR20047020099A patent/KR20050007603A/ko active IP Right Grant
- 2003-06-11 JP JP2004511245A patent/JP2005534657A/ja active Pending
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DE2043349A1 (en) * | 1970-09-01 | 1972-03-09 | Geo2/sb catalyst for colourless polyesters | |
US4048196A (en) * | 1974-11-23 | 1977-09-13 | Basf Aktiengesellschaft | Manufacture of butanediol and/or tetrahydrofuran from maleic and/or succinic anhydride via γ- butyrolactone |
US5196602A (en) * | 1991-12-30 | 1993-03-23 | The Standard Oil Company | Two-stage maleic anhydride hydrogenation process for 1,4-butanediol synthesis |
WO1997043234A1 (en) * | 1996-05-15 | 1997-11-20 | Kvaerner Process Technology Limited | Process for preparing gamma-butyrolactone, butane-1,4-diol and tetrahydrofuran |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010007327A2 (fr) * | 2008-07-18 | 2010-01-21 | Arkema France | Fabrication d'anhydride maleique a partir de matieres renouvelables, anhydride maleique obtenu et utilisations |
WO2010007327A3 (fr) * | 2008-07-18 | 2010-08-26 | Arkema France | Fabrication d'anhydride maleique a partir de matieres renouvelables, anhydride maleique obtenu et utilisations |
Also Published As
Publication number | Publication date |
---|---|
US7271299B2 (en) | 2007-09-18 |
DE10225929A1 (de) | 2003-12-24 |
EP1515933A1 (de) | 2005-03-23 |
AU2003242665A1 (en) | 2003-12-22 |
US20060167323A1 (en) | 2006-07-27 |
KR20050007603A (ko) | 2005-01-19 |
CN1668560A (zh) | 2005-09-14 |
CN100463889C (zh) | 2009-02-25 |
JP2005534657A (ja) | 2005-11-17 |
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