CA1072986A - Synthese industrielle en phase liquide d'ethers methyliques tertiaires - Google Patents

Synthese industrielle en phase liquide d'ethers methyliques tertiaires

Info

Publication number: CA1072986A
Authority: CA; Canada
Prior art keywords: catalyst; ether; methyl; liquid phase; methanol
Prior art date: 1975-07-23
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

CA 232057

Other languages

English (en)

Other versions

CA232057S (en

Inventor

Andrew T. Guttmann

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

Filing date

1975-07-23

Publication date

1980-03-04

1975-07-23 Application filed by Standard Oil Co filed Critical Standard Oil Co

1977-06-03 Priority to GB23663/77A priority Critical patent/GB1520726A/en

1977-06-16 Priority to BR7703932A priority patent/BR7703932A/pt

1977-06-17 Priority to BE178554A priority patent/BE855829A/fr

1979-09-04 Priority to US06/071,806 priority patent/US4259533A/en

1980-03-04 Application granted granted Critical

1980-03-04 Publication of CA1072986A publication Critical patent/CA1072986A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 22
230000008569 process Effects 0.000 title claims abstract description 18
239000007791 liquid phase Substances 0.000 title claims abstract description 5
150000002170 ethers Chemical group 0.000 title abstract 3
238000004519 manufacturing process Methods 0.000 title abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
238000002360 preparation method Methods 0.000 claims abstract description 6
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 5
150000001336 alkenes Chemical group 0.000 claims abstract description 5
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052721 tungsten Inorganic materials 0.000 claims abstract description 5
239000011964 heteropoly acid Substances 0.000 claims abstract description 3
229910052720 vanadium Inorganic materials 0.000 claims abstract description 3
239000003054 catalyst Substances 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
229910052698 phosphorus Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052776 Thorium Inorganic materials 0.000 claims description 2
229910052770 Uranium Inorganic materials 0.000 claims description 2
229910052787 antimony Inorganic materials 0.000 claims description 2
229910052785 arsenic Inorganic materials 0.000 claims description 2
229910052796 boron Inorganic materials 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
229910052732 germanium Inorganic materials 0.000 claims description 2
229910052748 manganese Inorganic materials 0.000 claims description 2
229910052702 rhenium Inorganic materials 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims 1
229910052802 copper Inorganic materials 0.000 claims 1
229910052759 nickel Inorganic materials 0.000 claims 1
229910052710 silicon Inorganic materials 0.000 claims 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 abstract description 5
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 abstract description 5
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract description 4
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract description 3
239000011733 molybdenum Substances 0.000 abstract description 3
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract description 3
239000010937 tungsten Substances 0.000 abstract description 3
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
241000282326 Felis catus Species 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
-1 alkyl methyl ether Chemical compound 0.000 description 2
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
239000002638 heterogeneous catalyst Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
241000518994 Conta Species 0.000 description 1
241000220317 Rosa Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA 232057 1975-07-23 1975-07-23 Synthese industrielle en phase liquide d'ethers methyliques tertiaires Expired CA1072986A (fr)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
GB23663/77A GB1520726A (en)	1975-07-23	1977-06-03	Liquid phase process for the manufacture of methyl tertiary alkyl ethers
BR7703932A BR7703932A (pt)	1975-07-23	1977-06-16	Processo em fase liquida para producao de eteres metilicos terciarios
BE178554A BE855829A (fr)	1975-07-23	1977-06-17	Preparation d'ethers methyl-t-alkyliques et produits ainsi obtenus
US06/071,806 US4259533A (en)	1975-07-23	1979-09-04	Liquid phase process for the manufacture of methyl tertiary ethers

Publications (1)

Publication Number	Publication Date
CA1072986A true CA1072986A (fr)	1980-03-04

Family

ID=209489

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 232057 Expired CA1072986A (fr)	1975-07-23	1975-07-23	Synthese industrielle en phase liquide d'ethers methyliques tertiaires

Country Status (1)

Country	Link
CA (1)	CA1072986A (fr)

1975
- 1975-07-23 CA CA 232057 patent/CA1072986A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-03-04	MKEX	Expiry

Publication	Publication Date	Title
CA1048481A (fr)	1979-02-13	Catalyseurs a teneur de chrome servant aux reactions d'oxydation
US3293268A (en)	1966-12-20	Production of maleic anhydride by oxidation of n-butane
US4180678A (en)	1979-12-25	Process for preparing methacrylic acid
US3226421A (en)	1965-12-28	Catalytic process for the preparation of nitriles
US4970348A (en)	1990-11-13	Chromium halogenated coordination complexes for the oxidation of butane to methylethylketone
US7019165B2 (en)	2006-03-28	Polyoxometallate catalysts and catalytic processes
US3347899A (en)	1967-10-17	Catalytic process for the preparation of nitriles
US5191116A (en)	1993-03-02	Process for the preparation of methacrylic acid and methacrolein
US4025565A (en)	1977-05-24	Process for preparing unsaturated aldehyde having three to four carbon atoms
US4052418A (en)	1977-10-04	Preparation of maleic anhydride from four-carbon hydrocarbons
US4225466A (en)	1980-09-30	Catalytic oxide composition for preparing methacrylic acid
US3965163A (en)	1976-06-22	Process for preparing unsaturated carboxylic acids from the corresponding unsaturated aldehydes
US4171316A (en)	1979-10-16	Preparation of maleic anhydride using a crystalline vanadium(IV)bis(metaphosphate) catalyst
JPS5950667B2 (ja)	1984-12-10	種々の金属を助触媒とした触媒を使う不飽和ニトリルの製造法
US4285875A (en)	1981-08-25	Process for preparing carboxylic acids by catalytic oxidation of aldehydes
US3960954A (en)	1976-06-01	Process for preparing oximes and hydroxylamines
CA1072986A (fr)	1980-03-04	Synthese industrielle en phase liquide d'ethers methyliques tertiaires
SU957763A3 (ru)	1982-09-07	Способ получени акрилонитрила
US3576764A (en)	1971-04-27	Catalyst for the oxidation of olefins to unsaturated aldehydes and acids
US4046783A (en)	1977-09-06	Method of olefin epoxidation
US4361709A (en)	1982-11-30	Process for the production of o-alkylated phenols
US4243607A (en)	1981-01-06	Process for the preparation of tetrachloroalkanes
US4259533A (en)	1981-03-31	Liquid phase process for the manufacture of methyl tertiary ethers
US3370083A (en)	1968-02-20	Catalytic process for the preparation of nitriles
US4082785A (en)	1978-04-04	Manufacture of acrylonitrile from propylene, ammonia and oxygen