JP2003511428A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003511428A5 JP2003511428A5 JP2001530080A JP2001530080A JP2003511428A5 JP 2003511428 A5 JP2003511428 A5 JP 2003511428A5 JP 2001530080 A JP2001530080 A JP 2001530080A JP 2001530080 A JP2001530080 A JP 2001530080A JP 2003511428 A5 JP2003511428 A5 JP 2003511428A5
- Authority
- JP
- Japan
- Prior art keywords
- maleic anhydride
- hydrogenation
- maleic
- stream
- feed
- 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.)
- Granted
Links
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 53
- 238000005984 hydrogenation reaction Methods 0.000 description 38
- 238000000034 method Methods 0.000 description 37
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 27
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 15
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000011976 maleic acid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000005233 alkylalcohol group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical group COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 4
- 235000011087 fumaric acid Nutrition 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 C 4 compound Chemical class 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical group COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LJYCJDQBTIMDPJ-UHFFFAOYSA-N [P]=O.[V] Chemical compound [P]=O.[V] LJYCJDQBTIMDPJ-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- ANSWCYTXKAIJOK-UHFFFAOYSA-N dibutyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCOC(=O)C1CCCCC1C(=O)OCCCC ANSWCYTXKAIJOK-UHFFFAOYSA-N 0.000 description 1
- AIACXWOETVLBIA-UHFFFAOYSA-N dimethyl cyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCCCC1C(=O)OC AIACXWOETVLBIA-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 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 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000001145 hydrido group Chemical class *[H] 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 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
- 238000010926 purge Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99308020.9 | 1999-10-12 | ||
| EP99308020 | 1999-10-12 | ||
| PCT/GB2000/003805 WO2001027058A1 (en) | 1999-10-12 | 2000-10-04 | Process for the simultaneous production of maleic anhydride and its hydrogenated derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004221745A Division JP4933037B2 (ja) | 1999-10-12 | 2004-07-29 | 無水マレイン酸およびその水素化誘導体の同時生成方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003511428A JP2003511428A (ja) | 2003-03-25 |
| JP2003511428A5 true JP2003511428A5 (enExample) | 2007-11-29 |
| JP4933011B2 JP4933011B2 (ja) | 2012-05-16 |
Family
ID=8241667
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001530080A Expired - Fee Related JP4933011B2 (ja) | 1999-10-12 | 2000-10-04 | 無水マレイン酸およびその水素化誘導体の同時生成方法 |
| JP2004221745A Expired - Fee Related JP4933037B2 (ja) | 1999-10-12 | 2004-07-29 | 無水マレイン酸およびその水素化誘導体の同時生成方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004221745A Expired - Fee Related JP4933037B2 (ja) | 1999-10-12 | 2004-07-29 | 無水マレイン酸およびその水素化誘導体の同時生成方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | USRE39794E1 (enExample) |
| EP (2) | EP1428812B1 (enExample) |
| JP (2) | JP4933011B2 (enExample) |
| KR (2) | KR100549732B1 (enExample) |
| CN (2) | CN1241887C (enExample) |
| AR (2) | AR025798A1 (enExample) |
| AT (2) | ATE300511T1 (enExample) |
| AU (1) | AU775354C (enExample) |
| BR (2) | BR0017431B1 (enExample) |
| CA (1) | CA2387268C (enExample) |
| DE (2) | DE60021632T2 (enExample) |
| ES (2) | ES2226920T3 (enExample) |
| MX (1) | MXPA02003676A (enExample) |
| MY (2) | MY122525A (enExample) |
| NO (2) | NO327782B1 (enExample) |
| SG (1) | SG144711A1 (enExample) |
| TW (2) | TWI232213B (enExample) |
| WO (1) | WO2001027058A1 (enExample) |
| ZA (1) | ZA200202572B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY122525A (en) * | 1999-10-12 | 2006-04-29 | Kvaerner Process Tech Ltd | Process for the simultaneous production of maleic anyhydride and its hydrogenated derivatives |
| GB0325526D0 (en) | 2003-10-31 | 2003-12-03 | Davy Process Techn Ltd | Process |
| GB0421928D0 (en) | 2004-10-01 | 2004-11-03 | Davy Process Techn Ltd | Process |
| JP2006321995A (ja) * | 2005-04-22 | 2006-11-30 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
| DE102006024903A1 (de) * | 2006-05-24 | 2007-11-29 | Basf Ag | Verfahren zur Vermeidung von Fumarsäureablagerungen bei der Herstellung von Maleinsäureanhydrid |
| US20080009652A1 (en) * | 2006-07-05 | 2008-01-10 | Huntsman Petrochemical Corporation | Process of Making Butyric Acid |
| 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 |
| CN104096376B (zh) * | 2014-06-27 | 2016-03-09 | 常州瑞华化工工程技术有限公司 | 一种防止顺酐装置氧化产物冷凝器堵塞的方法和装置 |
| EP3559156A1 (en) * | 2016-12-20 | 2019-10-30 | SABIC Global Technologies B.V. | Utilization of normal carbon 4 (nc4) recycle stream for secondary and tertiary products |
| EP3969465B1 (en) * | 2019-07-16 | 2024-09-04 | Thirumalai Chemicals Limited | Production of malic acid |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2574644A (en) * | 1948-07-06 | 1951-11-13 | Chempatents Inc | Recovery of polycarboxylic acid anhydrides |
| US3741993A (en) * | 1970-02-03 | 1973-06-26 | Tenneco Chem | Maleic anhydride process |
| US3904652A (en) * | 1972-11-16 | 1975-09-09 | Standard Oil Co Indiana | Recycle process for oxidation of n-butane to maleic anhydride |
| GB2207914A (en) | 1987-07-30 | 1989-02-15 | Davy Mckee | Process for the production of a mixture of butane 1,4-diol gamma-butyrolactone and tetrahydrofuran |
| TW341568B (en) * | 1995-12-27 | 1998-10-01 | Akzo Nobel Nv | Process for manufacturing Gamma-butyrolactone and its use |
| ZA973972B (en) | 1996-05-14 | 1998-03-23 | Kvaerner Process Tech Ltd | A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran. |
| ZA973971B (en) | 1996-05-15 | 1998-03-23 | Kvaerner Process Tech Ltd | A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran. |
| JP3873464B2 (ja) * | 1997-07-22 | 2007-01-24 | 三菱化学株式会社 | 無水マレイン酸の製造方法 |
| CA2243402A1 (en) * | 1997-07-22 | 1999-01-22 | Hideo Suwa | Process for producing maleic anhydride |
| IT1297120B1 (it) * | 1997-12-16 | 1999-08-03 | Sigma Tau Ind Farmaceuti | Procedimento per la produzione di (r)-3-idrossi-4-butirrolattone utile nella preparazione della (r)-carnitina |
| BE1012342A6 (fr) * | 1998-01-08 | 2000-10-03 | Pantochim Sa | Procede de production de butanediol par hydrogenation en phase liquide. |
| US5972174A (en) * | 1998-01-13 | 1999-10-26 | Huntsman Petrochemical Corporation | Process for the purification of maleic anhydride |
| IT1298535B1 (it) * | 1998-02-02 | 2000-01-12 | Lonza Spa | Procedimento per la produzione di gamma-butirrolattone |
| DE69800886T2 (de) * | 1998-03-23 | 2001-10-11 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol, Butyrolacton und Tetrahydrofuran |
| BE1012274A7 (fr) * | 1998-11-10 | 2000-08-01 | Pantochim Sa | Procede a haute productivite pour la preparation de gamma butyrolactone et de tetrahydrofurane. |
| MY122525A (en) * | 1999-10-12 | 2006-04-29 | Kvaerner Process Tech Ltd | Process for the simultaneous production of maleic anyhydride and its hydrogenated derivatives |
| KR100344962B1 (ko) * | 2000-04-10 | 2002-07-20 | 한국에너지기술연구원 | 무수말레인산을 원료로 한 감마 부티로락톤 제조방법 |
| EP1167361A3 (en) * | 2000-06-19 | 2002-01-23 | Haldor Topsoe A/S | Process and catalyst for the production of y-butyrolactones |
-
2000
- 2000-09-15 MY MYPI20004305A patent/MY122525A/en unknown
- 2000-09-15 MY MYPI20041088A patent/MY139259A/en unknown
- 2000-09-27 AR ARP000105077A patent/AR025798A1/es active IP Right Grant
- 2000-10-04 US US11/229,446 patent/USRE39794E1/en not_active Expired - Lifetime
- 2000-10-04 AT AT04006321T patent/ATE300511T1/de not_active IP Right Cessation
- 2000-10-04 US US10/110,444 patent/US6620949B1/en not_active Ceased
- 2000-10-04 AT AT00964500T patent/ATE274487T1/de not_active IP Right Cessation
- 2000-10-04 KR KR1020027004658A patent/KR100549732B1/ko not_active Expired - Fee Related
- 2000-10-04 ES ES00964500T patent/ES2226920T3/es not_active Expired - Lifetime
- 2000-10-04 CN CNB008142076A patent/CN1241887C/zh not_active Expired - Fee Related
- 2000-10-04 JP JP2001530080A patent/JP4933011B2/ja not_active Expired - Fee Related
- 2000-10-04 DE DE60021632T patent/DE60021632T2/de not_active Expired - Lifetime
- 2000-10-04 MX MXPA02003676A patent/MXPA02003676A/es active IP Right Grant
- 2000-10-04 ES ES04006321T patent/ES2245773T3/es not_active Expired - Lifetime
- 2000-10-04 KR KR1020047004807A patent/KR100578997B1/ko not_active Expired - Fee Related
- 2000-10-04 DE DE60013311T patent/DE60013311T2/de not_active Expired - Lifetime
- 2000-10-04 CA CA002387268A patent/CA2387268C/en not_active Expired - Fee Related
- 2000-10-04 EP EP04006321A patent/EP1428812B1/en not_active Expired - Lifetime
- 2000-10-04 AU AU75431/00A patent/AU775354C/en not_active Ceased
- 2000-10-04 WO PCT/GB2000/003805 patent/WO2001027058A1/en not_active Ceased
- 2000-10-04 SG SG200402002-0A patent/SG144711A1/en unknown
- 2000-10-04 BR BRPI0017431-9A patent/BR0017431B1/pt not_active IP Right Cessation
- 2000-10-04 EP EP00964500A patent/EP1220822B1/en not_active Expired - Lifetime
- 2000-10-04 BR BR0014696-0A patent/BR0014696A/pt not_active Application Discontinuation
- 2000-10-04 CN CNB2004100325955A patent/CN100355741C/zh not_active Expired - Fee Related
- 2000-11-02 TW TW093114988A patent/TWI232213B/zh not_active IP Right Cessation
- 2000-11-02 TW TW089123115A patent/TWI228502B/zh not_active IP Right Cessation
-
2002
- 2002-04-02 ZA ZA200202572A patent/ZA200202572B/en unknown
- 2002-04-11 NO NO20021715A patent/NO327782B1/no not_active IP Right Cessation
-
2004
- 2004-04-23 AR ARP040101386A patent/AR044073A2/es active IP Right Grant
- 2004-04-26 NO NO20041707A patent/NO329594B1/no not_active IP Right Cessation
- 2004-07-29 JP JP2004221745A patent/JP4933037B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100464610B1 (ko) | 감마-부티로락톤,부탄-1,4-디올및테트라하이드로푸란의제조방법 | |
| JP2003511428A5 (enExample) | ||
| JP2000510837A (ja) | 1,4―ブタンジオール、ガンマ―ブチロラクトン及びテトラヒドロフランを製造する方法 | |
| FI106796B (fi) | Menetelmä karboksyylihappojen tai niiden estereiden valmistamiseksi tyydyttymättömien rasvahappojen tai niiden estereiden hapettavalla pilkkomisella | |
| JP4933011B2 (ja) | 無水マレイン酸およびその水素化誘導体の同時生成方法 | |
| JP2002507587A5 (enExample) | ||
| JP4268335B2 (ja) | ブタン−1,4−ジオール、ガンマ−ブチロラクトン及びテトラヒドロフランの製造方法 | |
| CN101448808B (zh) | 防止富马酸在马来酸酐生产中沉积的方法 | |
| Hiroshi et al. | Synthesis of (+)-5, 6, 7-trinor-4, 8-inter-m-phenylene PGI2 | |
| CN101868449B (zh) | 制备四氢呋喃的方法 | |
| US6329532B1 (en) | Method for separating maleic anhydride from maleic anhydride-containing mixtures by stripping | |
| AU2004201511B2 (en) | Process for the simultaneous production of maleic anhydride and its hydrogenated derivatives | |
| JPS63156737A (ja) | エタノ−ルの精製法 |