CA2301061A1 - High productivity process to produce maleic anhydride from n-butane - Google Patents
High productivity process to produce maleic anhydride from n-butane Download PDFInfo
- Publication number
- CA2301061A1 CA2301061A1 CA002301061A CA2301061A CA2301061A1 CA 2301061 A1 CA2301061 A1 CA 2301061A1 CA 002301061 A CA002301061 A CA 002301061A CA 2301061 A CA2301061 A CA 2301061A CA 2301061 A1 CA2301061 A1 CA 2301061A1
- Authority
- CA
- Canada
- Prior art keywords
- carbon dioxide
- butane
- process according
- oxygen
- reaction
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 77
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 title claims abstract description 75
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 152
- 239000007789 gas Substances 0.000 claims abstract description 102
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 76
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 76
- 239000001273 butane Substances 0.000 claims abstract description 70
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 70
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 238000004064 recycling Methods 0.000 claims abstract description 40
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
- 239000001301 oxygen Substances 0.000 claims abstract description 32
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 230000003647 oxidation Effects 0.000 claims abstract description 25
- 238000010521 absorption reaction Methods 0.000 claims abstract description 24
- 239000011541 reaction mixture Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000012808 vapor phase Substances 0.000 claims abstract description 3
- 238000010926 purge Methods 0.000 claims description 31
- 239000006096 absorbing agent Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910001868 water Inorganic materials 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 12
- 238000011084 recovery Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000005201 scrubbing Methods 0.000 claims description 8
- 239000012528 membrane Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000003795 desorption Methods 0.000 claims description 5
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- 229910001882 dioxygen Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- -1 phosphorus compound Chemical class 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229960002380 dibutyl phthalate Drugs 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- JKJKPRIBNYTIFH-UHFFFAOYSA-N phosphanylidynevanadium Chemical compound [V]#P JKJKPRIBNYTIFH-UHFFFAOYSA-N 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 238000006555 catalytic reaction Methods 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- JCVAWLVWQDNEGS-UHFFFAOYSA-N 1-(2-hydroxypropylamino)propan-2-ol;thiolane 1,1-dioxide;hydrate Chemical compound O.O=S1(=O)CCCC1.CC(O)CNCC(C)O JCVAWLVWQDNEGS-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- PXXKQOPKNFECSZ-UHFFFAOYSA-N platinum rhodium Chemical compound [Rh].[Pt] PXXKQOPKNFECSZ-UHFFFAOYSA-N 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 8
- 150000008064 anhydrides Chemical class 0.000 description 43
- 230000001590 oxidative effect Effects 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 238000001354 calcination Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical group [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- 239000002826 coolant Substances 0.000 description 2
- 238000004200 deflagration Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 101100219264 Petunia hybrida C4H2 gene Proteins 0.000 description 1
- DLXAZYQCSSNEPD-UHFFFAOYSA-N [O-2].[Mn+2].[Cu]=O Chemical compound [O-2].[Mn+2].[Cu]=O DLXAZYQCSSNEPD-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000012384 transportation and delivery Methods 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9800475 | 1998-06-23 | ||
| BE9800475A BE1012101A6 (fr) | 1998-06-23 | 1998-06-23 | Procede de conversion a haut rendement de n-butane en anhydride maleique par recyclage des gaz uses. |
| PCT/EP1999/004300 WO1999067194A1 (en) | 1998-06-23 | 1999-06-21 | High productivity process to produce maleic anhydride from n-butane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2301061A1 true CA2301061A1 (en) | 1999-12-29 |
Family
ID=3891316
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002301061A Abandoned CA2301061A1 (en) | 1998-06-23 | 1999-06-21 | High productivity process to produce maleic anhydride from n-butane |
| CA002301048A Abandoned CA2301048A1 (en) | 1998-06-23 | 1999-06-21 | Process for the preparation of improved vanadium-phosphorus catalysts and use thereof for the production of maleic anhydride |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002301048A Abandoned CA2301048A1 (en) | 1998-06-23 | 1999-06-21 | Process for the preparation of improved vanadium-phosphorus catalysts and use thereof for the production of maleic anhydride |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6040460A (https=) |
| EP (2) | EP1011859A1 (https=) |
| JP (2) | JP2002518172A (https=) |
| KR (2) | KR100622167B1 (https=) |
| CN (2) | CN1205162C (https=) |
| AT (1) | ATE235452T1 (https=) |
| AU (2) | AU4775399A (https=) |
| BE (1) | BE1012101A6 (https=) |
| BR (2) | BR9906553B1 (https=) |
| CA (2) | CA2301061A1 (https=) |
| DE (1) | DE69906224T2 (https=) |
| ES (1) | ES2196826T3 (https=) |
| WO (2) | WO1999067194A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6281378B1 (en) * | 1995-06-08 | 2001-08-28 | Nippon Shokubai Co., Ltd. | Vanadium-containing catalysts, process for manufacturing and use of the same |
| DE69916217T2 (de) | 1998-11-27 | 2005-04-07 | Mitsubishi Chemical Corp. | Verfahren zur Herstellung von Maleinsäureanhydrid |
| EP1055670B1 (en) * | 1999-05-25 | 2008-02-20 | Mitsubishi Chemical Corporation | Process for the production of maleic anhydride |
| US6858561B2 (en) * | 2003-05-15 | 2005-02-22 | Scientific Design Company, Inc. | Phosphorus/vanadium catalyst preparation |
| DE10334582A1 (de) * | 2003-07-28 | 2005-02-24 | Basf Ag | Verfahren zur Herstellung von Maleinsäureanhydrid |
| US7399456B2 (en) * | 2005-02-25 | 2008-07-15 | Conocophillips Company | Process for the removal of heavy metals from gases, and compositions therefor and therewith |
| JP5140674B2 (ja) * | 2006-09-05 | 2013-02-06 | ハンツマン ペトロケミカル エルエルシー | 改善されたマレイン酸無水物触媒およびその製造方法 |
| WO2009055406A2 (en) * | 2007-10-22 | 2009-04-30 | Huntsman Petrochemical Corporation | Improved oxidation catalyst for maleic anhydride production |
| JP5360834B2 (ja) * | 2008-03-25 | 2013-12-04 | バブコック日立株式会社 | 鉄化合物の影響を抑制した排ガス浄化触媒 |
| DE102008025834A1 (de) * | 2008-05-29 | 2009-12-03 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Maleinsäureanhydrid |
| US7972415B2 (en) * | 2008-12-11 | 2011-07-05 | Spx Corporation | Membrane-based compressed air breathing system |
| CN101531650B (zh) * | 2009-03-19 | 2010-04-21 | 江苏钟腾化工有限公司 | 一种从含顺酐气体中回收顺酐的部分冷凝工艺 |
| EP2470301A1 (de) | 2009-08-26 | 2012-07-04 | Basf Se | Katalysator-precursor für die herstellung von maleinsäureanhydrid und verfahren zu dessen herstellung |
| FR2958185B1 (fr) | 2010-03-30 | 2012-04-20 | Arkema France | Procede d'oxydation selective de monoxyde de carbone |
| CN106622317A (zh) * | 2010-09-10 | 2017-05-10 | 亨斯迈石油化学有限责任公司 | 用于生产马来酸酐的具有低钒氧化态的改进型 vpo催化剂 |
| 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 |
| CN104177317B (zh) * | 2014-07-31 | 2017-04-19 | 常州瑞华化工工程技术有限公司 | 防止顺酐循环尾气露点腐蚀的方法 |
| CN105001185A (zh) * | 2015-07-21 | 2015-10-28 | 宁波浙铁江宁化工有限公司 | 一种顺酐尾气处理设备及其工艺 |
| CN105617959A (zh) * | 2016-01-15 | 2016-06-01 | 湖南弘润化工科技有限公司 | 甲苯液相空气氧化法连续生产苯甲酸的反应装置 |
| US11289700B2 (en) | 2016-06-28 | 2022-03-29 | The Research Foundation For The State University Of New York | KVOPO4 cathode for sodium ion batteries |
| GB201616119D0 (en) * | 2016-09-22 | 2016-11-09 | Johnson Matthey Davy Technologies Limited | Process |
| CN109046412B (zh) * | 2018-08-23 | 2021-05-25 | 常州新日催化剂股份有限公司 | 一种正丁烷氧化制顺酐催化剂及其制备方法 |
| WO2022058188A1 (en) | 2020-09-17 | 2022-03-24 | Basf Se | Process for the production of glyoxal |
| CN119327376A (zh) * | 2023-07-20 | 2025-01-21 | 中国石化工程建设有限公司 | 一种正戊烷氧化制顺酐和苯酐的系统和方法 |
| WO2025062466A1 (en) | 2023-09-19 | 2025-03-27 | Conser Spa | Gas recycle maleic anydride process for high productivity and low carbon emissions |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3293268A (en) | 1964-03-23 | 1966-12-20 | Princeton Chemical Res Inc | Production of maleic anhydride by oxidation of n-butane |
| US3864280A (en) * | 1972-06-19 | 1975-02-04 | Chevron Res | Catalyst for a n-butane oxidation to maleic anhydride |
| US4132670A (en) | 1974-11-06 | 1979-01-02 | Chevron Research Company | Method of preparing vanadium (IV) phosphate composition with high intrinsic surface area |
| US3904652A (en) * | 1972-11-16 | 1975-09-09 | Standard Oil Co Indiana | Recycle process for oxidation of n-butane to maleic anhydride |
| US3899516A (en) * | 1973-10-17 | 1975-08-12 | Sun Ventures Inc | Oxidation of butane to maleic anhydride using butane-rich feed |
| US4064070A (en) | 1974-12-23 | 1977-12-20 | Chevron Research Company | Catalyst for producing maleic anhydride |
| US4222945A (en) * | 1978-01-30 | 1980-09-16 | Imperial Chemical Industries Limited | Production of maleic anhydride |
| DE2966881D1 (en) | 1978-01-30 | 1984-05-17 | Ici Plc | Production of carboxylic acid anhydrides and catalysts therefor |
| US4231943A (en) * | 1979-05-31 | 1980-11-04 | Chevron Research Company | Maleic anhydride production |
| US4247419A (en) * | 1979-12-13 | 1981-01-27 | Atlantic Richfield Company | Single phase vanadium(IV)bis(metaphosphate) oxidation catalyst with improved intrinsic surface area |
| US4312787A (en) | 1979-12-17 | 1982-01-26 | Standard Oil Company | Coated catalysts containing high loading of active phase, particularly useful in the preparation of maleic anhydride |
| US4333853A (en) | 1980-05-05 | 1982-06-08 | The Standard Oil Company | Mixed vanadium phosphorus oxide catalysts and preparation thereof |
| US4315864A (en) | 1980-10-22 | 1982-02-16 | Standard Oil Company (Ohio) | Preparation of maleic anhydride |
| US4317778A (en) * | 1980-12-29 | 1982-03-02 | Standard Oil Company (Sohio) | Preparation of maleic anhydride using fluidized catalysts |
| US4342699A (en) * | 1981-02-23 | 1982-08-03 | Standard Oil Company (Indiana) | Process for production of maleic anhydride |
| US4392986A (en) | 1981-10-08 | 1983-07-12 | Exxon Research & Engineering Co. | Catalyst for carboxylic anhydride production |
| US4562268A (en) | 1983-12-28 | 1985-12-31 | Monsanto Company | Process for producing maleic anhydride |
| US4632915A (en) | 1985-10-28 | 1986-12-30 | Monsanto Company | Iron/lithium--promoted catalysts for the production of maleic anhydride |
| US5011945A (en) * | 1987-08-31 | 1991-04-30 | Amoco Corporation | Continuous process for the production of maleic anhydride |
| IT1253698B (it) * | 1990-05-31 | 1995-08-23 | Sisas Spa | Procedimento per il recupero di anidride maleica da miscele di reazione |
| US5262547A (en) * | 1990-10-31 | 1993-11-16 | The Boc Group, Inc. | Process for the production of petrochemicals |
| US5126463A (en) * | 1990-10-31 | 1992-06-30 | The Boc Group, Inc. | Process for the production of anhydrides |
| HUT58680A (en) * | 1990-11-14 | 1992-03-30 | Boc Group Inc | Process for producing anhydrides and nitriles |
| US5137860A (en) | 1991-06-27 | 1992-08-11 | Monsanto Company | Process for the transformation of vanadium/phosphorus mixed oxide catalyst precursors into active catalysts for the production of maleic anhydride |
| BE1008103A3 (fr) * | 1994-04-22 | 1996-01-16 | Pantochim Sa | Procede de preparation de catalyseurs au vanadium et phosphore et leur utilisation pour la production d'anhydride maleique. |
| IT1269970B (it) * | 1994-06-30 | 1997-04-16 | Sisas Spa | Procedimento di riciclo di gas esausti nel processo di conversione di n-butano ad anidride maleica |
| IT1290407B1 (it) * | 1996-04-29 | 1998-12-03 | Lonza Spa | Procedimento per la trasformazione di un precursore di catalizzatore a base di ossido misto di vanadio/fosforo nel catalizzatore attivo |
-
1998
- 1998-06-23 BE BE9800475A patent/BE1012101A6/fr not_active IP Right Cessation
-
1999
- 1999-06-21 WO PCT/EP1999/004300 patent/WO1999067194A1/en not_active Ceased
- 1999-06-21 EP EP99932707A patent/EP1011859A1/en not_active Withdrawn
- 1999-06-21 CA CA002301061A patent/CA2301061A1/en not_active Abandoned
- 1999-06-21 EP EP99931128A patent/EP1007499B1/en not_active Expired - Lifetime
- 1999-06-21 CN CNB998012084A patent/CN1205162C/zh not_active Expired - Fee Related
- 1999-06-21 BR BRPI9906553-3A patent/BR9906553B1/pt not_active IP Right Cessation
- 1999-06-21 CA CA002301048A patent/CA2301048A1/en not_active Abandoned
- 1999-06-21 CN CN99801207A patent/CN1119205C/zh not_active Expired - Fee Related
- 1999-06-21 ES ES99931128T patent/ES2196826T3/es not_active Expired - Lifetime
- 1999-06-21 BR BR9906554-1A patent/BR9906554A/pt not_active Application Discontinuation
- 1999-06-21 WO PCT/EP1999/004301 patent/WO1999067021A1/en not_active Ceased
- 1999-06-21 AU AU47753/99A patent/AU4775399A/en not_active Abandoned
- 1999-06-21 AU AU48998/99A patent/AU745774B2/en not_active Ceased
- 1999-06-21 AT AT99931128T patent/ATE235452T1/de not_active IP Right Cessation
- 1999-06-21 KR KR1020007001856A patent/KR100622167B1/ko not_active Expired - Fee Related
- 1999-06-21 JP JP2000555698A patent/JP2002518172A/ja not_active Withdrawn
- 1999-06-21 DE DE69906224T patent/DE69906224T2/de not_active Expired - Fee Related
- 1999-06-21 JP JP2000555850A patent/JP2002518466A/ja active Pending
- 1999-06-21 KR KR1020007001850A patent/KR20010023221A/ko not_active Withdrawn
- 1999-06-22 US US09/337,542 patent/US6040460A/en not_active Expired - Lifetime
- 1999-06-22 US US09/337,541 patent/US6174833B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1119205C (zh) | 2003-08-27 |
| KR20010023227A (ko) | 2001-03-26 |
| EP1007499A1 (en) | 2000-06-14 |
| WO1999067021A1 (en) | 1999-12-29 |
| BE1012101A6 (fr) | 2000-05-02 |
| CN1205162C (zh) | 2005-06-08 |
| AU4899899A (en) | 2000-01-10 |
| ES2196826T3 (es) | 2003-12-16 |
| EP1007499B1 (en) | 2003-03-26 |
| EP1011859A1 (en) | 2000-06-28 |
| DE69906224T2 (de) | 2003-12-11 |
| KR20010023221A (ko) | 2001-03-26 |
| WO1999067194A1 (en) | 1999-12-29 |
| JP2002518466A (ja) | 2002-06-25 |
| DE69906224D1 (de) | 2003-04-30 |
| US6040460A (en) | 2000-03-21 |
| CA2301048A1 (en) | 1999-12-29 |
| CN1274343A (zh) | 2000-11-22 |
| AU745774B2 (en) | 2002-03-28 |
| BR9906553A (pt) | 2000-08-15 |
| ATE235452T1 (de) | 2003-04-15 |
| AU4775399A (en) | 2000-01-10 |
| US6174833B1 (en) | 2001-01-16 |
| CN1274301A (zh) | 2000-11-22 |
| BR9906553B1 (pt) | 2010-09-08 |
| JP2002518172A (ja) | 2002-06-25 |
| BR9906554A (pt) | 2000-08-15 |
| KR100622167B1 (ko) | 2006-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1007499B1 (en) | High productivity process to produce maleic anhydride from n-buthane | |
| KR100609203B1 (ko) | 에탄 또는 에틸렌 산화로부터 비닐 아세테이트 단량체의제조방법 | |
| AU652186B2 (en) | Production of hydrocarbon derivatives | |
| KR100995792B1 (ko) | 알켄 분리 방법 | |
| EP1989161B1 (en) | Integrated process for the production of acetic acid and vinyl acetate | |
| US4987239A (en) | Process for the production of anhydrides | |
| US4990632A (en) | Process for the production of oxides | |
| US5688970A (en) | Process to recycle exhaust gases from n-butane conversion into maleic anhydride | |
| US5126463A (en) | Process for the production of anhydrides | |
| KR100191187B1 (ko) | 이소부탄의 촉매 산화에 의한 메타크릴산의 제조방법 | |
| US5008412A (en) | Process for the production of oxides | |
| KR20080096686A (ko) | 에탄-기재 공정에서 에탄으로부터 에틸렌을 분리하여 아세트산을 제조하기 위한 화학 반응의 용도 | |
| CA2640677C (en) | Butane absorption system for vent control and ethylene purification | |
| JP3258394B2 (ja) | 亜酸化窒素の製造方法 | |
| JPH0327350A (ja) | ニトリル類の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |