DE69916217T2 - Verfahren zur Herstellung von Maleinsäureanhydrid - Google Patents
Verfahren zur Herstellung von Maleinsäureanhydrid Download PDFInfo
- Publication number
- DE69916217T2 DE69916217T2 DE69916217T DE69916217T DE69916217T2 DE 69916217 T2 DE69916217 T2 DE 69916217T2 DE 69916217 T DE69916217 T DE 69916217T DE 69916217 T DE69916217 T DE 69916217T DE 69916217 T2 DE69916217 T2 DE 69916217T2
- Authority
- DE
- Germany
- Prior art keywords
- hydrocarbon
- reactor
- gas
- concentration
- maleic anhydride
- 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.)
- Expired - Lifetime
Links
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims description 105
- 238000000034 method Methods 0.000 title claims description 85
- 238000002360 preparation method Methods 0.000 title description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 206
- 150000002430 hydrocarbons Chemical class 0.000 claims description 205
- 239000004215 Carbon black (E152) Substances 0.000 claims description 199
- 239000007789 gas Substances 0.000 claims description 175
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 127
- 239000001301 oxygen Substances 0.000 claims description 127
- 229910052760 oxygen Inorganic materials 0.000 claims description 127
- 238000006243 chemical reaction Methods 0.000 claims description 85
- 238000011084 recovery Methods 0.000 claims description 78
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 37
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 239000012495 reaction gas Substances 0.000 claims description 17
- 238000004064 recycling Methods 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 238000001179 sorption measurement Methods 0.000 claims description 11
- 230000001419 dependent effect Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 50
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 41
- 238000004880 explosion Methods 0.000 description 37
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 34
- 239000001273 butane Substances 0.000 description 23
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 23
- 238000004519 manufacturing process Methods 0.000 description 21
- 239000002994 raw material Substances 0.000 description 19
- 239000001569 carbon dioxide Substances 0.000 description 17
- 229910002092 carbon dioxide Inorganic materials 0.000 description 17
- 238000000926 separation method Methods 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229910001868 water Inorganic materials 0.000 description 7
- 239000002360 explosive Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- JKJKPRIBNYTIFH-UHFFFAOYSA-N phosphanylidynevanadium Chemical compound [V]#P JKJKPRIBNYTIFH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- -1 Compound maleic anhydride Chemical class 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LEABNKXSQUTCOW-UHFFFAOYSA-N [O].[P].[V] Chemical compound [O].[P].[V] LEABNKXSQUTCOW-UHFFFAOYSA-N 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 150000003022 phthalic acids Chemical class 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 241000693046 Listeria phage PSA Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 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
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09B—EDUCATIONAL OR DEMONSTRATION APPLIANCES; APPLIANCES FOR TEACHING, OR COMMUNICATING WITH, THE BLIND, DEAF OR MUTE; MODELS; PLANETARIA; GLOBES; MAPS; DIAGRAMS
- G09B9/00—Simulators for teaching or training purposes
- G09B9/02—Simulators for teaching or training purposes for teaching control of vehicles or other craft
- G09B9/04—Simulators for teaching or training purposes for teaching control of vehicles or other craft for teaching control of land vehicles
- G09B9/05—Simulators for teaching or training purposes for teaching control of vehicles or other craft for teaching control of land vehicles the view from a vehicle being simulated
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09B—EDUCATIONAL OR DEMONSTRATION APPLIANCES; APPLIANCES FOR TEACHING, OR COMMUNICATING WITH, THE BLIND, DEAF OR MUTE; MODELS; PLANETARIA; GLOBES; MAPS; DIAGRAMS
- G09B19/00—Teaching not covered by other main groups of this subclass
- G09B19/14—Traffic procedures, e.g. traffic regulations
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Theoretical Computer Science (AREA)
- Business, Economics & Management (AREA)
- Educational Technology (AREA)
- Educational Administration (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Aviation & Aerospace Engineering (AREA)
- Entrepreneurship & Innovation (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33735698 | 1998-11-27 | ||
| JP33735698 | 1998-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69916217D1 DE69916217D1 (de) | 2004-05-13 |
| DE69916217T2 true DE69916217T2 (de) | 2005-04-07 |
Family
ID=18307860
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69916217T Expired - Lifetime DE69916217T2 (de) | 1998-11-27 | 1999-11-26 | Verfahren zur Herstellung von Maleinsäureanhydrid |
| DE69929720T Expired - Lifetime DE69929720T2 (de) | 1998-11-27 | 1999-11-26 | Verfahren zur Herstellung von Maleinsäureanhydrid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69929720T Expired - Lifetime DE69929720T2 (de) | 1998-11-27 | 1999-11-26 | Verfahren zur Herstellung von Maleinsäureanhydrid |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US6310219B1 (en:Method) |
| EP (2) | EP1004567B1 (en:Method) |
| KR (2) | KR100615341B1 (en:Method) |
| DE (2) | DE69916217T2 (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6610917B2 (en) | 1998-05-15 | 2003-08-26 | Lester F. Ludwig | Activity indication, external source, and processing loop provisions for driven vibrating-element environments |
| EP1055670B1 (en) * | 1999-05-25 | 2008-02-20 | Mitsubishi Chemical Corporation | Process for the production of maleic anhydride |
| DE10334582A1 (de) | 2003-07-28 | 2005-02-24 | Basf Ag | Verfahren zur Herstellung von Maleinsäureanhydrid |
| CN101711235A (zh) | 2007-04-16 | 2010-05-19 | 雅培制药有限公司 | 7-未取代的吲哚mcl-1抑制剂 |
| WO2010105143A2 (en) | 2009-03-13 | 2010-09-16 | Natureworks Llc | Methods for producing lactide with recycle of meso-lactide |
| EP2647929B1 (en) * | 2010-12-03 | 2020-01-22 | Mitsubishi Electric Corporation | Part replacement method for refrigeration cycle device and refrigeration cycle device |
| CN108727313B (zh) * | 2018-08-21 | 2023-10-31 | 宁波浙铁江宁化工有限公司 | 顺酐的试反应系统 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3904652A (en) * | 1972-11-16 | 1975-09-09 | Standard Oil Co Indiana | Recycle process for oxidation of n-butane to maleic anhydride |
| DE2403042A1 (de) | 1973-02-05 | 1974-08-08 | Allied Chem | Verfahren zur herstellung von maleinsaeureanhydrid |
| DE2309657A1 (de) | 1973-02-27 | 1974-09-12 | Basf Ag | Verfahren zur herstellung von carbonsaeuren oder dicarbonsaeureanhydriden |
| DE2330841A1 (de) | 1973-06-16 | 1975-01-16 | Basf Ag | Verfahren zur herstellung von carbonsaeuren oder dicarbonsaeureanhydriden |
| US3899516A (en) | 1973-10-17 | 1975-08-12 | Sun Ventures Inc | Oxidation of butane to maleic anhydride using butane-rich feed |
| US4259246A (en) | 1975-12-31 | 1981-03-31 | Chevron Research Company | Maleic anhydride production with recycle treatment |
| 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 |
| EP0029317B1 (en) | 1979-11-20 | 1986-03-19 | Imperial Chemical Industries Plc | Production of maleic anhydride |
| US4342699A (en) | 1981-02-23 | 1982-08-03 | Standard Oil Company (Indiana) | Process for production of maleic anhydride |
| DE3277533D1 (en) | 1982-07-20 | 1987-12-03 | Amoco Corp | Process for production of maleic anhydride |
| US4668802A (en) | 1985-01-18 | 1987-05-26 | E. I. Du Pont De Nemours And Company | Improved vapor phase catalytic oxidation of butane to maleic anhydride |
| US5011945A (en) | 1987-08-31 | 1991-04-30 | Amoco Corporation | Continuous process for the production of maleic anhydride |
| US4868330A (en) | 1988-04-06 | 1989-09-19 | The Boc Group, Inc. | Process for the production of nitriles |
| US4987239A (en) | 1988-04-06 | 1991-01-22 | The Boc Group, Inc. | Process for the production of anhydrides |
| US5126463A (en) | 1990-10-31 | 1992-06-30 | The Boc Group, Inc. | Process for the production of anhydrides |
| US5262547A (en) | 1990-10-31 | 1993-11-16 | The Boc Group, Inc. | Process for the production of petrochemicals |
| HUT58680A (en) * | 1990-11-14 | 1992-03-30 | Boc Group Inc | Process for producing anhydrides and nitriles |
| US5179215A (en) | 1991-02-27 | 1993-01-12 | The Boc Group, Inc. | Process for the production of petrochemicals |
| ZA935853B (en) | 1992-08-21 | 1994-06-10 | Boc Group Inc | Process for producing hydrocarbon partial oxidation products |
| 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 |
| TW338064B (en) | 1995-06-01 | 1998-08-11 | Boc Group Inc | Process for the production of petrochemicals |
| US5646304A (en) | 1995-06-23 | 1997-07-08 | The Boc Group, Inc. | Process for the production of petrochemicals |
| US5726327A (en) | 1996-09-27 | 1998-03-10 | The Boc Group, Inc. | Process for the production of petrochemicals |
| CA2243402A1 (en) | 1997-07-22 | 1999-01-22 | Hideo Suwa | Process for producing maleic anhydride |
| BE1012101A6 (fr) | 1998-06-23 | 2000-05-02 | Pantochim Sa | Procede de conversion a haut rendement de n-butane en anhydride maleique par recyclage des gaz uses. |
-
1999
- 1999-11-26 DE DE69916217T patent/DE69916217T2/de not_active Expired - Lifetime
- 1999-11-26 KR KR1019990053028A patent/KR100615341B1/ko not_active Expired - Fee Related
- 1999-11-26 US US09/450,126 patent/US6310219B1/en not_active Expired - Lifetime
- 1999-11-26 EP EP99123229A patent/EP1004567B1/en not_active Expired - Lifetime
- 1999-11-26 DE DE69929720T patent/DE69929720T2/de not_active Expired - Lifetime
- 1999-11-26 EP EP03015634A patent/EP1359138B1/en not_active Expired - Lifetime
-
2001
- 2001-07-11 US US09/901,686 patent/US6620948B2/en not_active Expired - Lifetime
-
2006
- 2006-01-24 KR KR1020060007177A patent/KR100631315B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69929720D1 (de) | 2006-04-20 |
| DE69916217D1 (de) | 2004-05-13 |
| KR20060012049A (ko) | 2006-02-06 |
| US6620948B2 (en) | 2003-09-16 |
| EP1359138A2 (en) | 2003-11-05 |
| EP1359138B1 (en) | 2006-02-08 |
| DE69929720T2 (de) | 2006-09-21 |
| KR100615341B1 (ko) | 2006-08-25 |
| EP1004567A3 (en) | 2000-11-08 |
| EP1004567B1 (en) | 2004-04-07 |
| EP1004567A2 (en) | 2000-05-31 |
| EP1359138A3 (en) | 2003-11-19 |
| KR100631315B1 (ko) | 2006-10-09 |
| US6310219B1 (en) | 2001-10-30 |
| KR20000047740A (ko) | 2000-07-25 |
| US20020004603A1 (en) | 2002-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8332 | No legal effect for de | ||
| 8370 | Indication of lapse of patent is to be deleted | ||
| 8364 | No opposition during term of opposition |