CA1122958A - Catalyseur pour la preparation d'anhydride maleique a partir d'hydrocarbures a 4 carbones - Google Patents

Catalyseur pour la preparation d'anhydride maleique a partir d'hydrocarbures a 4 carbones

Info

Publication number: CA1122958A
Authority: CA; Canada
Prior art keywords: catalyst; element selected; group; zinc; arsenic
Prior art date: 1975-08-06
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

CA352,925A

Other languages

English (en)

Inventor

Dev D. Suresh

Noel J. Bremer

Robert K. Grasselli

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.)

Standard Oil Co

Original Assignee

Standard Oil 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.)

1975-08-06

Filing date

1980-05-28

Publication date

1982-05-04

1975-08-06 Priority claimed from US05/602,343 external-priority patent/US4052418A/en

1980-05-28 Application filed by Standard Oil Co filed Critical Standard Oil Co

1980-05-28 Priority to CA352,925A priority Critical patent/CA1122958A/fr

1982-05-04 Application granted granted Critical

1982-05-04 Publication of CA1122958A publication Critical patent/CA1122958A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 57
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title abstract description 10
229930195733 hydrocarbon Natural products 0.000 title abstract description 8
238000002360 preparation method Methods 0.000 title abstract description 4
229910052799 carbon Inorganic materials 0.000 title abstract description 3
239000000203 mixture Substances 0.000 claims abstract description 17
239000010955 niobium Substances 0.000 claims abstract description 7
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052721 tungsten Inorganic materials 0.000 claims abstract description 7
239000010937 tungsten Substances 0.000 claims abstract description 7
229910052758 niobium Inorganic materials 0.000 claims abstract description 6
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052715 tantalum Inorganic materials 0.000 claims abstract description 6
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims abstract description 6
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 5
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052796 boron Inorganic materials 0.000 claims abstract description 4
229910052804 chromium Inorganic materials 0.000 claims abstract description 4
239000011651 chromium Substances 0.000 claims abstract description 4
239000011701 zinc Substances 0.000 claims description 11
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
229910052725 zinc Inorganic materials 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
229910052785 arsenic Inorganic materials 0.000 claims description 8
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 8
229910052684 Cerium Inorganic materials 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
229910052793 cadmium Inorganic materials 0.000 claims description 4
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 4
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
229910052742 iron Inorganic materials 0.000 claims description 4
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 3
229910052776 Thorium Inorganic materials 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
239000011135 tin Substances 0.000 claims description 3
229910052718 tin Inorganic materials 0.000 claims description 3
229910052770 Uranium Inorganic materials 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 4
229910052700 potassium Inorganic materials 0.000 claims 4
239000011591 potassium Substances 0.000 claims 4
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 2
229910052748 manganese Inorganic materials 0.000 claims 2
239000011572 manganese Substances 0.000 claims 2
235000002908 manganese Nutrition 0.000 claims 2
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 8
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract description 8
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 7
229910001882 dioxygen Inorganic materials 0.000 abstract description 7
229910052720 vanadium Inorganic materials 0.000 abstract description 5
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract description 4
229910052787 antimony Inorganic materials 0.000 abstract description 4
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract description 4
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract description 3
230000000694 effects Effects 0.000 abstract description 3
230000003647 oxidation Effects 0.000 abstract description 3
238000007254 oxidation reaction Methods 0.000 abstract description 3
-1 CARBON HYDROCARBONS Chemical class 0.000 abstract description 2
239000012808 vapor phase Substances 0.000 abstract description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
150000002430 hydrocarbons Chemical class 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 5
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 description 2
URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
229940000488 arsenic acid Drugs 0.000 description 1
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 1
229910000149 boron phosphate Inorganic materials 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Landscapes

Catalysts (AREA)

CA352,925A 1975-08-06 1980-05-28 Catalyseur pour la preparation d'anhydride maleique a partir d'hydrocarbures a 4 carbones Expired CA1122958A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA352,925A CA1122958A (fr)	1975-08-06	1980-05-28	Catalyseur pour la preparation d'anhydride maleique a partir d'hydrocarbures a 4 carbones

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/602,343 US4052418A (en)	1975-08-06	1975-08-06	Preparation of maleic anhydride from four-carbon hydrocarbons
CA258,387A CA1086325A (fr)	1975-08-06	1976-08-04	Preparation d'anhydride maleique a partir d'hydrocarbures a chaine de quatre atomes de carbone
CA352,925A CA1122958A (fr)	1975-08-06	1980-05-28	Catalyseur pour la preparation d'anhydride maleique a partir d'hydrocarbures a 4 carbones
US602,343		1984-04-20

Publications (1)

Publication Number	Publication Date
CA1122958A true CA1122958A (fr)	1982-05-04

Family

ID=27164586

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA352,925A Expired CA1122958A (fr)	1975-08-06	1980-05-28	Catalyseur pour la preparation d'anhydride maleique a partir d'hydrocarbures a 4 carbones

Country Status (1)

Country	Link
CA (1)	CA1122958A (fr)

1980
- 1980-05-28 CA CA352,925A patent/CA1122958A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-05-04	MKEX	Expiry

Publication	Publication Date	Title
US4002650A (en)	1977-01-11	Preparation of maleic anhydride from n-butane
CA1086325A (fr)	1980-09-23	Preparation d'anhydride maleique a partir d'hydrocarbures a chaine de quatre atomes de carbone
US3875220A (en)	1975-04-01	Process for the preparation of methacrylic acid from methacrolein
US4017521A (en)	1977-04-12	Process for the manufacture of maleic anhydride using high surface area catalyst
US4217309A (en)	1980-08-12	Process for producing methacrolein
CA1072072A (fr)	1980-02-19	Procede pour la preparation d'acides insatures a partir d'aldehydes insatures
US5191116A (en)	1993-03-02	Process for the preparation of methacrylic acid and methacrolein
US4377534A (en)	1983-03-22	Production of unsaturated nitriles
US3953370A (en)	1976-04-27	Method of activating zinc ferrite oxidative dehydrogenation catalysts
US4165300A (en)	1979-08-21	Oxidation catalysts
US3965163A (en)	1976-06-22	Process for preparing unsaturated carboxylic acids from the corresponding unsaturated aldehydes
US4219484A (en)	1980-08-26	Production of maleic anhydride from four-carbon hydrocarbons using catalysts prepared by water reflux techniques
US4139552A (en)	1979-02-13	Production of unsaturated nitriles
US4292203A (en)	1981-09-29	Oxidation catalysts
US4234461A (en)	1980-11-18	Oxidation catalysts
US4010114A (en)	1977-03-01	Oxidative dehydrogenation catalyst
US4036901A (en)	1977-07-19	Process for producing styrene
US4083805A (en)	1978-04-11	Preparation of methacrylic acid from methacrolein
US4652543A (en)	1987-03-24	Catalysts useful for the manufacture of maleic anhydride having a characteristic X-ray diffraction pattern
US3313856A (en)	1967-04-11	Preparation of acrolein or methacrolein
US4021427A (en)	1977-05-03	Oxidation of 1,3-butadiene to maleic anhydride using a catalyst containing Mo, Sb, V and either one or both of Li and Ce
CA1122958A (fr)	1982-05-04	Catalyseur pour la preparation d'anhydride maleique a partir d'hydrocarbures a 4 carbones
US4293443A (en)	1981-10-06	Oxidation catalysts
US4663479A (en)	1987-05-05	Preparation of aliphatic carboxylic acids and aldehydes by upgrading alpha-hydroxycarboxylic acids
US4093635A (en)	1978-06-06	Preparation of maleic anhydride from four-carbon hydrocarbons