CA1093566A - Production d'anhydride maleique avec recyclage - Google Patents

Production d'anhydride maleique avec recyclage

Info

Publication number: CA1093566A
Authority: CA; Canada
Prior art keywords: maleic anhydride; reactor; effluent; acids; butane
Prior art date: 1975-12-31
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

Application number

CA267,822A

Other languages

English (en)

Inventor

Kiran R. Bakshi

Stephen G. Paradis

David M. Marquis

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology Co

Priority date (The priority date 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 date listed.)

1975-12-31

Filing date

1976-12-14

Publication date

1981-01-13

1976-12-14 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1981-01-13 Application granted granted Critical

1981-01-13 Publication of CA1093566A publication Critical patent/CA1093566A/fr

Status Expired legal-status Critical Current

Links

FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 31
238000004519 manufacturing process Methods 0.000 title abstract description 3
239000002253 acid Substances 0.000 claims abstract description 35
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 30
150000007513 acids Chemical class 0.000 claims abstract description 29
239000003054 catalyst Substances 0.000 claims abstract description 19
238000000034 method Methods 0.000 claims abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 13
229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 13
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
238000006243 chemical reaction Methods 0.000 claims abstract description 11
238000005201 scrubbing Methods 0.000 claims abstract description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
229910001392 phosphorus oxide Inorganic materials 0.000 claims abstract description 7
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 5
239000011976 maleic acid Substances 0.000 claims abstract description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 5
229910001935 vanadium oxide Inorganic materials 0.000 claims abstract description 5
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims abstract description 4
238000004064 recycling Methods 0.000 claims abstract description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 3
239000002250 absorbent Substances 0.000 claims description 4
230000002745 absorbent Effects 0.000 claims description 4
239000001273 butane Substances 0.000 abstract description 20
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract description 20
239000003518 caustics Substances 0.000 abstract description 2
230000003647 oxidation Effects 0.000 description 11
238000007254 oxidation reaction Methods 0.000 description 11
238000012360 testing method Methods 0.000 description 11
239000007789 gas Substances 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000000356 contaminant Substances 0.000 description 5
229960005419 nitrogen Drugs 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000006096 absorbing agent Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000002939 deleterious effect Effects 0.000 description 3
239000002360 explosive Substances 0.000 description 3
239000013505 freshwater Substances 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910052720 vanadium Inorganic materials 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
241000022563 Rema Species 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229910002090 carbon oxide Inorganic materials 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
-1 e.g. Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
LJYCJDQBTIMDPJ-UHFFFAOYSA-N [P]=O.[V] Chemical compound [P]=O.[V] LJYCJDQBTIMDPJ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
150000008366 benzophenones Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
JKJKPRIBNYTIFH-UHFFFAOYSA-N phosphanylidynevanadium Chemical compound [V]#P JKJKPRIBNYTIFH-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000010025 steaming Methods 0.000 description 1
VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 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
- 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
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein

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)

CA267,822A 1975-12-31 1976-12-14 Production d'anhydride maleique avec recyclage Expired CA1093566A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US64558475A	1975-12-31	1975-12-31
US645,584		1975-12-31

Publications (1)

Publication Number	Publication Date
CA1093566A true CA1093566A (fr)	1981-01-13

Family

ID=24589605

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA267,822A Expired CA1093566A (fr)	1975-12-31	1976-12-14	Production d'anhydride maleique avec recyclage

Country Status (8)

Country	Link
JP (1)	JPS6055513B2 (fr)
BE (1)	BE849980A (fr)
CA (1)	CA1093566A (fr)
DE (1)	DE2658191C2 (fr)
FR (1)	FR2337132A1 (fr)
GB (1)	GB1516430A (fr)
IT (1)	IT1067952B (fr)
NL (1)	NL187747C (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0099431B1 (fr) *	1982-07-20	1987-10-28	Amoco Corporation	Procédé de production d'anhydride maléique
JPS62286824A (ja) *	1986-06-06	1987-12-12	Diesel Kiki Co Ltd	車室内送風装置
US6194587B1 (en) *	1999-08-19	2001-02-27	Scientific Design Company, Inc.	Production of maleic anhydride

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3741993A (en) *	1970-02-03	1973-06-26	Tenneco Chem	Maleic anhydride process
US3864280A (en) *	1972-06-19	1975-02-04	Chevron Res	Catalyst for a n-butane oxidation to maleic anhydride
JPS5144141B2 (fr) *	1972-07-29	1976-11-26
US3904652A (en) *	1972-11-16	1975-09-09	Standard Oil Co Indiana	Recycle process for oxidation of n-butane to maleic anhydride
GB1528451A (en) *	1974-10-03	1978-10-11	Atomic Energy Authority Uk	Manufacture of bags

1976
- 1976-12-14 CA CA267,822A patent/CA1093566A/fr not_active Expired
- 1976-12-22 DE DE19762658191 patent/DE2658191C2/de not_active Expired
- 1976-12-22 JP JP51153548A patent/JPS6055513B2/ja not_active Expired
- 1976-12-23 NL NL7614362A patent/NL187747C/xx not_active IP Right Cessation
- 1976-12-23 FR FR7638912A patent/FR2337132A1/fr active Granted
- 1976-12-29 BE BE173739A patent/BE849980A/fr not_active IP Right Cessation
- 1976-12-30 IT IT3098976A patent/IT1067952B/it active
- 1976-12-31 GB GB5445576A patent/GB1516430A/en not_active Expired

Also Published As

Publication number	Publication date
GB1516430A (en)	1978-07-05
NL7614362A (nl)	1977-07-04
FR2337132B1 (fr)	1980-08-08
NL187747C (nl)	1992-01-02
DE2658191C2 (de)	1985-01-31
BE849980A (fr)	1977-04-15
FR2337132A1 (fr)	1977-07-29
JPS5283324A (en)	1977-07-12
DE2658191A1 (de)	1977-07-14
IT1067952B (it)	1985-03-21
JPS6055513B2 (ja)	1985-12-05
NL187747B (nl)	1991-08-01

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
US4329493A (en)	1982-05-11	Process for producing terephthalic acid
US5262547A (en)	1993-11-16	Process for the production of petrochemicals
EP0318205A1 (fr)	1989-05-31	Procédé pour la production de nitriles et d'anhydrides
KR100622167B1 (ko)	2006-09-07	ｎ-부탄으로부터 말레산 무수물을 제조하는 고생산성 방법
US4987239A (en)	1991-01-22	Process for the production of anhydrides
US4868330A (en)	1989-09-19	Process for the production of nitriles
JPH04288023A (ja)	1992-10-13	石油化学製品の製造方法
EP0325446B1 (fr)	1993-05-05	Elimination d'impuretés dans des courants contenant du monoxyde de carbone et/ou d'hydrogène
US5126463A (en)	1992-06-30	Process for the production of anhydrides
US5532384A (en)	1996-07-02	Process for producing hydrocarbon partial oxidation products
JPH08301818A (ja)	1996-11-19	炭酸ジメチルの連続製造方法
EP0013100B1 (fr)	1982-05-19	Récupération du brome des gaz effluents de l'oxydation catalytique à l'aide de brome
US4259246A (en)	1981-03-31	Maleic anhydride production with recycle treatment
JP2937292B2 (ja)	1999-08-23	炭酸ジメチルの連続製造方法
US3646239A (en)	1972-02-29	Enzymatic treatment of hydrocarbon dehydrogenation effluent
US5177225A (en)	1993-01-05	Process for the production of alkylene oxide
EP1359138B1 (fr)	2006-02-08	Procédé pour la préparation de l'anhydride maléique
US8598402B2 (en)	2013-12-03	Butane absorption system for vent control and ethylene purification
JPS61146318A (ja)	1986-07-04	ガス混合物の処理
DE2544972A1 (de)	1977-04-21	Verfahren zur herstellung von maleinsaeureanhydrid
DE2658191C2 (de)	1985-01-31	Verfahren zur Herstellung von Maleinsäureanhydrid
US1716028A (en)	1929-06-04	Effluent-gas treatment
CA1093567A (fr)	1981-01-13	Obtention d'anhydride maleique
JP3206340B2 (ja)	2001-09-10	炭酸ジメチルの連続的製造方法
GB2556668A (en)	2018-06-06	Process