CA2382248C - Production of maleic anhydride - Google Patents
Production of maleic anhydride Download PDFInfo
- Publication number
- CA2382248C CA2382248C CA002382248A CA2382248A CA2382248C CA 2382248 C CA2382248 C CA 2382248C CA 002382248 A CA002382248 A CA 002382248A CA 2382248 A CA2382248 A CA 2382248A CA 2382248 C CA2382248 C CA 2382248C
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- maleic anhydride
- butane
- gas mixture
- 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.)
- Expired - Lifetime
Links
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000007789 gas Substances 0.000 claims abstract description 49
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000012495 reaction gas Substances 0.000 claims description 10
- 238000005201 scrubbing Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 22
- 238000007254 oxidation reaction Methods 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 11
- 230000000153 supplemental effect Effects 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 230000008901 benefit Effects 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000013022 venting Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910000975 Carbon steel Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 239000010962 carbon steel Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- KPYCVQASEGGKEG-UHFFFAOYSA-N 3-hydroxyoxolane-2,5-dione Chemical compound OC1CC(=O)OC1=O KPYCVQASEGGKEG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 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
- 238000010276 construction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- NLPVCCRZRNXTLT-UHFFFAOYSA-N dioxido(dioxo)molybdenum;nickel(2+) Chemical compound [Ni+2].[O-][Mo]([O-])(=O)=O NLPVCCRZRNXTLT-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- NRUSYECJYOYVQB-UHFFFAOYSA-L potassium disodium nitrate dinitrite Chemical compound N(=O)[O-].[K+].N(=O)[O-].[Na+].[N+](=O)([O-])[O-].[Na+] NRUSYECJYOYVQB-UHFFFAOYSA-L 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910000634 wood's metal Inorganic materials 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/377,589 | 1999-08-19 | ||
| US09/377,589 US6194587B1 (en) | 1999-08-19 | 1999-08-19 | Production of maleic anhydride |
| PCT/US2000/021962 WO2001014359A1 (en) | 1999-08-19 | 2000-08-11 | Production of maleic anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2382248A1 CA2382248A1 (en) | 2001-03-01 |
| CA2382248C true CA2382248C (en) | 2008-10-28 |
Family
ID=23489730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002382248A Expired - Lifetime CA2382248C (en) | 1999-08-19 | 2000-08-11 | Production of maleic anhydride |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6194587B1 (enExample) |
| EP (1) | EP1212310B1 (enExample) |
| JP (1) | JP4753515B2 (enExample) |
| KR (1) | KR100715705B1 (enExample) |
| CN (1) | CN1142925C (enExample) |
| AT (1) | ATE277029T1 (enExample) |
| AU (1) | AU777861B2 (enExample) |
| BR (1) | BR0013398B1 (enExample) |
| CA (1) | CA2382248C (enExample) |
| DE (1) | DE60014120T2 (enExample) |
| ES (1) | ES2226901T3 (enExample) |
| MX (1) | MXPA02001725A (enExample) |
| WO (1) | WO2001014359A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4648515B2 (ja) * | 2000-05-02 | 2011-03-09 | 株式会社日本触媒 | 反応器のスタートアップ方法 |
| DE10235355A1 (de) * | 2002-08-02 | 2004-02-19 | Basf Ag | Verfahren zur Herstellung von Maleinsäureanhydrid |
| US7619099B2 (en) * | 2006-04-17 | 2009-11-17 | Scientific Design Company, Inc. | Reduction of acrylic acid in the production of maleic anhydride |
| US7589217B2 (en) * | 2006-04-24 | 2009-09-15 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Yield improvement in the production of maleic anhydride |
| DE102008025834A1 (de) | 2008-05-29 | 2009-12-03 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Maleinsäureanhydrid |
| CN104356100A (zh) * | 2014-11-14 | 2015-02-18 | 常州新日催化剂有限公司 | 正丁烷氧化制顺丁烯二酸酐的方法 |
| CN108786683B (zh) * | 2018-08-21 | 2023-10-03 | 宁波浙铁江宁化工有限公司 | 顺酐的试反应装置 |
| IT201900013167A1 (it) | 2019-07-29 | 2021-01-29 | Polynt S P A | Letto catalitico multistrato per l'ossidazione parziale di n-butano ad anidride maleica. |
| CN117999125A (zh) | 2021-09-14 | 2024-05-07 | 意大利波林股份有限公司 | 用于将正丁烷部分氧化成马来酸酐的催化剂 |
| DE102022004204A1 (de) | 2022-11-12 | 2024-05-23 | Hans-Jürgen Eberle | Vefahren zur Herstellung von Maleinsäureanhydrid |
| CN116020344A (zh) * | 2022-12-08 | 2023-04-28 | 西安陕鼓动力股份有限公司 | 用于马来酸酐制备系统的汽电双驱的空气供应装置的运行方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2638481A (en) * | 1950-05-26 | 1953-05-12 | Hercules Powder Co Ltd | Maleic acid manufacture |
| CA1093566A (en) * | 1975-12-31 | 1981-01-13 | Kiran R. Bakshi | Maleic anhydride production with recycle treatment |
| US4231943A (en) * | 1979-05-31 | 1980-11-04 | Chevron Research Company | Maleic anhydride production |
| DE69203909T2 (de) * | 1991-04-05 | 1995-12-07 | Scient Design Co | Zweistufiges Verfahren zur Herstellung von Malein-Säureanhydrid aus Butan. |
| KR930017610A (ko) * | 1992-02-17 | 1993-09-20 | 셀 인터나쵸 나아레 레사아치 마아츠샤피 비이부이 | 화학적 전환을 수행하기 위한 방법 및 장치 |
| JPH10330335A (ja) * | 1997-05-27 | 1998-12-15 | Mitsubishi Chem Corp | Ｄｌ−アスパラギン酸の製造方法 |
| US5885919A (en) | 1997-07-30 | 1999-03-23 | Scientific Design Company, Inc. | Phosphorus/vanadium catalyst preparation |
| GB9724004D0 (en) * | 1997-11-13 | 1998-10-21 | Kvaerner Process Tech Ltd | Process |
-
1999
- 1999-08-19 US US09/377,589 patent/US6194587B1/en not_active Expired - Lifetime
-
2000
- 2000-08-11 CA CA002382248A patent/CA2382248C/en not_active Expired - Lifetime
- 2000-08-11 EP EP00953969A patent/EP1212310B1/en not_active Expired - Lifetime
- 2000-08-11 CN CNB008113734A patent/CN1142925C/zh not_active Expired - Lifetime
- 2000-08-11 ES ES00953969T patent/ES2226901T3/es not_active Expired - Lifetime
- 2000-08-11 DE DE60014120T patent/DE60014120T2/de not_active Expired - Lifetime
- 2000-08-11 BR BRPI0013398-1A patent/BR0013398B1/pt not_active IP Right Cessation
- 2000-08-11 JP JP2001518446A patent/JP4753515B2/ja not_active Expired - Lifetime
- 2000-08-11 MX MXPA02001725A patent/MXPA02001725A/es active IP Right Grant
- 2000-08-11 WO PCT/US2000/021962 patent/WO2001014359A1/en not_active Ceased
- 2000-08-11 AT AT00953969T patent/ATE277029T1/de active
- 2000-08-11 AU AU66329/00A patent/AU777861B2/en not_active Expired
- 2000-08-11 KR KR1020027002016A patent/KR100715705B1/ko not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1212310B1 (en) | 2004-09-22 |
| DE60014120T2 (de) | 2006-02-23 |
| EP1212310A4 (en) | 2002-09-25 |
| KR100715705B1 (ko) | 2007-05-08 |
| CA2382248A1 (en) | 2001-03-01 |
| ES2226901T3 (es) | 2005-04-01 |
| JP4753515B2 (ja) | 2011-08-24 |
| BR0013398B1 (pt) | 2011-06-14 |
| DE60014120D1 (de) | 2004-10-28 |
| KR20020033460A (ko) | 2002-05-06 |
| AU6632900A (en) | 2001-03-19 |
| AU777861B2 (en) | 2004-11-04 |
| JP2003507464A (ja) | 2003-02-25 |
| CN1142925C (zh) | 2004-03-24 |
| US6194587B1 (en) | 2001-02-27 |
| WO2001014359A1 (en) | 2001-03-01 |
| MXPA02001725A (es) | 2002-10-23 |
| CN1368968A (zh) | 2002-09-11 |
| EP1212310A1 (en) | 2002-06-12 |
| ATE277029T1 (de) | 2004-10-15 |
| BR0013398A (pt) | 2002-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20200811 |