CA1093567A - Obtention d'anhydride maleique - Google Patents

Obtention d'anhydride maleique

Info

Publication number: CA1093567A
Authority: CA; Canada
Prior art keywords: butane; maleic anhydride; reactor; accordance; vanadium
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

CA267,824A

Other languages

English (en)

Inventor

Kiran R. Bakshi

David M. Marquis

Stephen G. Paradis

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 CA1093567A publication Critical patent/CA1093567A/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 40
238000004519 manufacturing process Methods 0.000 title abstract description 4
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 100
239000001273 butane Substances 0.000 claims abstract description 75
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 75
239000003054 catalyst Substances 0.000 claims abstract description 50
238000006243 chemical reaction Methods 0.000 claims abstract description 40
238000000034 method Methods 0.000 claims abstract description 35
230000008569 process Effects 0.000 claims abstract description 32
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 28
239000001301 oxygen Substances 0.000 claims abstract description 28
229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
229910001392 phosphorus oxide Inorganic materials 0.000 claims abstract description 6
238000004064 recycling Methods 0.000 claims abstract description 6
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
239000007789 gas Substances 0.000 claims description 31
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
239000003463 adsorbent Substances 0.000 claims description 12
238000001179 sorption measurement Methods 0.000 claims description 9
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 7
229910052720 vanadium Inorganic materials 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
LJYCJDQBTIMDPJ-UHFFFAOYSA-N [P]=O.[V] Chemical class [P]=O.[V] LJYCJDQBTIMDPJ-UHFFFAOYSA-N 0.000 claims description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
239000011148 porous material Substances 0.000 claims description 4
230000006872 improvement Effects 0.000 claims description 3
JKJKPRIBNYTIFH-UHFFFAOYSA-N phosphanylidynevanadium Chemical compound [V]#P JKJKPRIBNYTIFH-UHFFFAOYSA-N 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
239000002802 bituminous coal Substances 0.000 claims description 2
239000001569 carbon dioxide Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000002250 absorbent Substances 0.000 claims 1
230000002745 absorbent Effects 0.000 claims 1
235000014786 phosphorus Nutrition 0.000 claims 1
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
229940044600 maleic anhydride Drugs 0.000 description 28
238000007254 oxidation reaction Methods 0.000 description 11
230000003647 oxidation Effects 0.000 description 10
239000007800 oxidant agent Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 8
238000003795 desorption Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 6
229960005419 nitrogen Drugs 0.000 description 6
238000011084 recovery Methods 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 5
230000007423 decrease Effects 0.000 description 5
238000010926 purge Methods 0.000 description 5
229940045605 vanadium Drugs 0.000 description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
239000002360 explosive Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000006096 absorbing agent Substances 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000000926 separation method Methods 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 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
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
238000002336 sorption--desorption measurement Methods 0.000 description 2
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
101000837192 Drosophila melanogaster Teneurin-m Proteins 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
DOMWKUIIPQCAJU-LJHIYBGHSA-N Hydroxyprogesterone caproate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)CCCCC)[C@@]1(C)CC2 DOMWKUIIPQCAJU-LJHIYBGHSA-N 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
241000164466 Palaemon adspersus Species 0.000 description 1
241000183024 Populus tremula Species 0.000 description 1
RPENMPUGTSTQSJ-UHFFFAOYSA-N [N].[O].CCCC Chemical compound [N].[O].CCCC RPENMPUGTSTQSJ-UHFFFAOYSA-N 0.000 description 1
XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940057971 butane Drugs 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000008859 change Effects 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
230000002301 combined effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012809 cooling fluid Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
230000001419 dependent effect Effects 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
-1 e.g. Substances 0.000 description 1
239000003546 flue gas Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
239000001307 helium Substances 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000010354 integration Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
230000003319 supportive effect Effects 0.000 description 1
VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 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

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)

CA267,824A 1975-12-31 1976-12-14 Obtention d'anhydride maleique Expired CA1093567A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US64558575A	1975-12-31	1975-12-31
US645,585		1991-01-24

Publications (1)

Publication Number	Publication Date
CA1093567A true CA1093567A (fr)	1981-01-13

Family

ID=24589607

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA267,824A Expired CA1093567A (fr)	1975-12-31	1976-12-14	Obtention d'anhydride maleique

Country Status (8)

Country	Link
JP (1)	JPS5283325A (fr)
BE (1)	BE849981A (fr)
CA (1)	CA1093567A (fr)
DE (1)	DE2658129C2 (fr)
FR (1)	FR2337133A1 (fr)
GB (1)	GB1538610A (fr)
IT (1)	IT1067295B (fr)
NL (1)	NL7614363A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA935853B (en) *	1992-08-21	1994-06-10	Boc Group Inc	Process for producing hydrocarbon partial oxidation products

Family Cites Families (3)

* 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
US3904652A (en) *	1972-11-16	1975-09-09	Standard Oil Co Indiana	Recycle process for oxidation of n-butane to maleic anhydride
DE2544972A1 (de) *	1975-10-08	1977-04-21	Hoechst Ag	Verfahren zur herstellung von maleinsaeureanhydrid

1976
- 1976-12-14 CA CA267,824A patent/CA1093567A/fr not_active Expired
- 1976-12-22 DE DE19762658129 patent/DE2658129C2/de not_active Expired
- 1976-12-22 JP JP15354976A patent/JPS5283325A/ja active Granted
- 1976-12-23 NL NL7614363A patent/NL7614363A/xx not_active Application Discontinuation
- 1976-12-23 FR FR7638980A patent/FR2337133A1/fr active Granted
- 1976-12-29 BE BE173740A patent/BE849981A/fr not_active IP Right Cessation
- 1976-12-30 IT IT3098876A patent/IT1067295B/it active
- 1976-12-31 GB GB5445476A patent/GB1538610A/en not_active Expired

Also Published As

Publication number	Publication date
BE849981A (fr)	1977-04-15
NL7614363A (nl)	1977-07-04
FR2337133A1 (fr)	1977-07-29
JPS5283325A (en)	1977-07-12
FR2337133B1 (fr)	1980-03-14
DE2658129C2 (de)	1985-04-04
GB1538610A (en)	1979-01-24
JPS5532706B2 (fr)	1980-08-26
IT1067295B (it)	1985-03-16
DE2658129A1 (de)	1977-07-14

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
US4231943A (en)	1980-11-04	Maleic anhydride production
US5008414A (en)	1991-04-16	Process for the production of oxides
US5015756A (en)	1991-05-14	Process for the production of nitriles
EP0484136B1 (fr)	1996-01-03	Production de dérivés d'hydrocarbures
KR100622167B1 (ko)	2006-09-07	ｎ-부탄으로부터 말레산 무수물을 제조하는 고생산성 방법
US4870201A (en)	1989-09-26	Process for the production of nitriles
US4849538A (en)	1989-07-18	Process for the production of nitriles
US4987239A (en)	1991-01-22	Process for the production of anhydrides
JPH05117217A (ja)	1993-05-14	石油化学品を製造する方法
US4849537A (en)	1989-07-18	Process for the production of nitriles
US4990632A (en)	1991-02-05	Process for the production of oxides
US4868330A (en)	1989-09-19	Process for the production of nitriles
US5278319A (en)	1994-01-11	Process for the production of hydrocarbon partial oxidation products
US5712313A (en)	1998-01-27	Process for carrying out chemical equilibrium reactions
EP2493840B1 (fr)	2015-07-01	Procédé de production d'acétate d'allyle
CA1093567A (fr)	1981-01-13	Obtention d'anhydride maleique
US5534648A (en)	1996-07-09	Process for continuously producing dimethyl carbonate
JP2969965B2 (ja)	1999-11-02	イソブタンの接触酸化によるメタクリル酸の製造方法
US5008412A (en)	1991-04-16	Process for the production of oxides
JP2937292B2 (ja)	1999-08-23	炭酸ジメチルの連続製造方法
US4943650A (en)	1990-07-24	Process for the production of nitriles
US4259246A (en)	1981-03-31	Maleic anhydride production with recycle treatment
JP2918285B2 (ja)	1999-07-12	ニトリル類の製造法
EP0139423A2 (fr)	1985-05-02	Procédé de production d'hydrogène très pur
JPS6160061B2 (fr)	1986-12-19