CA1133505A - Methode d'oxydation de olefines - Google Patents

Methode d'oxydation de olefines

Info

Publication number: CA1133505A
Authority: CA; Canada
Prior art keywords: catalyst; mixtures; catalysts; propylene; isobutylene
Prior art date: 1977-07-28
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

CA306,381A

Other languages

English (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

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.)

1977-07-28

Filing date

1978-06-28

Publication date

1982-10-12

1978-06-28 Application filed by Standard Oil Co filed Critical Standard Oil Co

1982-10-12 Application granted granted Critical

1982-10-12 Publication of CA1133505A publication Critical patent/CA1133505A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 26
230000003647 oxidation Effects 0.000 title claims abstract description 12
238000007254 oxidation reaction Methods 0.000 title claims abstract description 12
150000001336 alkenes Chemical class 0.000 title abstract description 12
239000003054 catalyst Substances 0.000 claims abstract description 77
239000002253 acid Substances 0.000 claims abstract description 11
150000001299 aldehydes Chemical class 0.000 claims abstract description 11
150000007513 acids Chemical class 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 20
229910052721 tungsten Inorganic materials 0.000 claims description 18
229910052804 chromium Inorganic materials 0.000 claims description 17
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
229910052732 germanium Inorganic materials 0.000 claims description 15
229910052748 manganese Inorganic materials 0.000 claims description 15
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 15
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 15
229910052698 phosphorus Inorganic materials 0.000 claims description 13
229910052718 tin Inorganic materials 0.000 claims description 13
229910052802 copper Inorganic materials 0.000 claims description 9
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052759 nickel Inorganic materials 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052749 magnesium Inorganic materials 0.000 claims description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
229910052797 bismuth Inorganic materials 0.000 claims description 6
229910017052 cobalt Inorganic materials 0.000 claims description 6
239000010941 cobalt Substances 0.000 claims description 6
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
229910001882 dioxygen Inorganic materials 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910052701 rubidium Inorganic materials 0.000 claims description 6
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
229910052788 barium Inorganic materials 0.000 claims description 4
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
229910052790 beryllium Inorganic materials 0.000 claims description 4
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical group [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 4
229910052793 cadmium Inorganic materials 0.000 claims description 4
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical group [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 4
229910052792 caesium Inorganic materials 0.000 claims description 4
229910052791 calcium Inorganic materials 0.000 claims description 4
239000011575 calcium Chemical group 0.000 claims description 4
229910052705 radium Inorganic materials 0.000 claims description 4
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical group [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims description 4
229910052712 strontium Inorganic materials 0.000 claims description 4
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 4
229910052714 tellurium Inorganic materials 0.000 claims description 4
239000012808 vapor phase Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Chemical group 0.000 claims description 4
229910052684 Cerium Inorganic materials 0.000 claims description 3
229910052777 Praseodymium Inorganic materials 0.000 claims description 3
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
229910052709 silver Inorganic materials 0.000 claims description 3
239000004332 silver Substances 0.000 claims description 3
229910052716 thallium Inorganic materials 0.000 claims description 3
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
229940058494 beryllium Drugs 0.000 claims 3
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims 3
-1 B is Co Inorganic materials 0.000 claims 1
230000003197 catalytic effect Effects 0.000 abstract description 7
238000006243 chemical reaction Methods 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
229910052782 aluminium Inorganic materials 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
229910052787 antimony Inorganic materials 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
229910052681 coesite Inorganic materials 0.000 description 3
229910052906 cristobalite Inorganic materials 0.000 description 3
230000007423 decrease Effects 0.000 description 3
229910052733 gallium Inorganic materials 0.000 description 3
229910052738 indium Inorganic materials 0.000 description 3
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
229910052746 lanthanum Inorganic materials 0.000 description 3
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910052682 stishovite Inorganic materials 0.000 description 3
229910052905 tridymite Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
229910052745 lead Inorganic materials 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
239000011733 molybdenum Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000011591 potassium Substances 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910019614 (NH4)6 Mo7 O24.4H2 O Inorganic materials 0.000 description 1
229910000608 Fe(NO3)3.9H2O Inorganic materials 0.000 description 1
FIXLYHHVMHXSCP-UHFFFAOYSA-H azane;dihydroxy(dioxo)molybdenum;trioxomolybdenum;tetrahydrate Chemical compound N.N.N.N.N.N.O.O.O.O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O FIXLYHHVMHXSCP-UHFFFAOYSA-H 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
QGUAJWGNOXCYJF-UHFFFAOYSA-N cobalt dinitrate hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QGUAJWGNOXCYJF-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(II) nitrate Inorganic materials [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/888—Tungsten
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/888—Tungsten
- B01J23/8885—Tungsten containing also molybdenum
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8993—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with chromium, molybdenum or tungsten
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/057—Selenium or tellurium; Compounds thereof
- B01J27/0576—Tellurium; Compounds thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
- 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA306,381A 1977-07-28 1978-06-28 Methode d'oxydation de olefines Expired CA1133505A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81973377A	1977-07-09	1977-07-09
US819,733		1977-07-28

Publications (1)

Publication Number	Publication Date
CA1133505A true CA1133505A (fr)	1982-10-12

Family

ID=25228904

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA306,381A Expired CA1133505A (fr)	1977-07-28	1978-06-28	Methode d'oxydation de olefines

Country Status (13)

Country	Link
EP (1)	EP0000663B1 (fr)
AT (1)	AT359055B (fr)
BR (1)	BR7804848A (fr)
CA (1)	CA1133505A (fr)
DD (1)	DD140034A5 (fr)
DE (1)	DE2861192D1 (fr)
ES (1)	ES472082A1 (fr)
IN (1)	IN148201B (fr)
IT (1)	IT1118241B (fr)
NO (1)	NO151083C (fr)
PT (1)	PT68313A (fr)
RO (1)	RO75319A (fr)
YU (1)	YU182978A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1127137A (fr) *	1977-12-20	1982-07-06	Dev D. Suresh	Ammoxydation d'olefines sur de nouveaux catalyseurs a l'antimonate
GB2077257B (en) *	1980-05-19	1984-06-27	Asahi Chemical Ind	Process for producing methacrolein
US4532365A (en) *	1982-09-20	1985-07-30	The Halcon Sd Group, Inc.	Conversion of alkanes to unsaturated aldehydes
EP0279374B1 (fr) *	1987-02-17	1992-01-02	Nippon Shokubai Kagaku Kogyo Co., Ltd	Catalyseur d'oxydation d'oléfines ou d'alcool tertiaire et procédé pour sa préparation
US5162578A (en) *	1987-06-12	1992-11-10	Union Carbide Chemicals & Plastics Technology Corporation	Acetic acid from ethane, ethylene and oxygen

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5112603B1 (fr) *	1971-05-26	1976-04-21
CA1049553A (fr) *	1973-04-30	1979-02-27	The Standard Oil Company	Synthese d'acide acrylique ou methacrylique a partir de propylene ou d'isobutylene
GB1456752A (en) *	1973-05-10	1976-11-24	Japan Synthetic Rubber Co Ltd	Catalyst and process for the production of unsaturated carbonyl compounds
US3972920A (en) *	1973-06-11	1976-08-03	Mitsubishi Rayon Co., Ltd.	Process for producing unsaturated aldehydes, unsaturated fatty acids or conjugated dienes
US4001317A (en) *	1974-07-22	1977-01-04	Standard Oil Company	Process for the oxidation of olefins using catalysts containing various promoter elements
GB1523772A (en) *	1974-07-22	1978-09-06	Standard Oil Co	Oxidation catalysts
GB1489559A (en) *	1975-03-03	1977-10-19	Mitsubishi Rayon Co	Catalytic process for the preparation of acrylic acid or methacrylic acid
GB1490683A (en) *	1975-03-12	1977-11-02	Mitsubishi Rayon Co	Process and a catalyst for producing unsaturated aldehydes unsaturated carboxylic acids or conjugated diene
IN142430B (fr) *	1975-04-21	1977-07-09	Standard Oil Co
US4118419A (en) *	1975-12-03	1978-10-03	Mitsubishi Rayon Company, Ltd.	Catalytic process for the preparation of an unsaturated carboxylic acid
DE2626887B2 (de) *	1976-06-16	1978-06-29	Basf Ag, 6700 Ludwigshafen	Katalysator für die Oxadation von (Methacrolein zu (Meth)Acrylsäure
US4065507A (en) *	1976-08-02	1977-12-27	Standard Oil Company	Preparation of methacrylic derivatives from tertiary butyl-containing compounds

1978
- 1978-06-28 CA CA306,381A patent/CA1133505A/fr not_active Expired
- 1978-07-11 IN IN516/DEL/78A patent/IN148201B/en unknown
- 1978-07-18 PT PT68313A patent/PT68313A/pt unknown
- 1978-07-24 DD DD78206895A patent/DD140034A5/de unknown
- 1978-07-25 DE DE7878300199T patent/DE2861192D1/de not_active Expired
- 1978-07-25 EP EP78300199A patent/EP0000663B1/fr not_active Expired
- 1978-07-26 IT IT26141/78A patent/IT1118241B/it active
- 1978-07-27 RO RO7894818A patent/RO75319A/fr unknown
- 1978-07-27 BR BR7804848A patent/BR7804848A/pt unknown
- 1978-07-27 NO NO782583A patent/NO151083C/no unknown
- 1978-07-27 ES ES472082A patent/ES472082A1/es not_active Expired
- 1978-07-28 AT AT551778A patent/AT359055B/de not_active IP Right Cessation
- 1978-07-28 YU YU01829/78A patent/YU182978A/xx unknown

Also Published As

Publication number	Publication date
AT359055B (de)	1980-10-27
NO151083C (no)	1985-02-06
RO75319A (fr)	1980-11-30
ATA551778A (de)	1980-03-15
NO782583L (no)	1979-01-30
IT1118241B (it)	1986-02-24
NO151083B (no)	1984-10-29
EP0000663A1 (fr)	1979-02-07
YU182978A (en)	1982-08-31
BR7804848A (pt)	1979-04-10
DD140034A5 (de)	1980-02-06
ES472082A1 (es)	1979-04-16
PT68313A (en)	1978-08-01
EP0000663B1 (fr)	1981-10-21
DE2861192D1 (en)	1981-12-24
IN148201B (fr)	1980-11-29
IT7826141A0 (it)	1978-07-26

Legal Events

Date	Code	Title	Description
1999-10-12	MKEX	Expiry

Publication	Publication Date	Title
US4001317A (en)	1977-01-04	Process for the oxidation of olefins using catalysts containing various promoter elements
US3875220A (en)	1975-04-01	Process for the preparation of methacrylic acid from methacrolein
US3956181A (en)	1976-05-11	Oxidation catalyst
US3932551A (en)	1976-01-13	Process for the preparation of diolefins from olefins
EP0437056B2 (fr)	1998-04-15	Catalyseur et procédé pour la production d'acrylonitrile et de méthycrylonitrile
US3642930A (en)	1972-02-15	Process for the manufacture of isoprene from isoamylenes and methyl butanols and catalyst therefor
US4155938A (en)	1979-05-22	Oxidation of olefins
CA2417987C (fr)	2007-10-23	Catalyseur ameliore destine a la fabrication d'acrylonitrile
US4556731A (en)	1985-12-03	Process for the oxidation of olefins using catalysts containing various promoter elements
US3522299A (en)	1970-07-28	Process for the oxidation of olefins to aldehydes and acids and catalyst therefor
US4052450A (en)	1977-10-04	Catalytic oxidation of α-olefins
US4560804A (en)	1985-12-24	Catalytic process for the manufacture of ketones
GB1564459A (en)	1980-04-10	Preparation of methacrylic derivatives
US4280928A (en)	1981-07-28	Catalyst compositions and their use for the preparation of methacrolein
US4354044A (en)	1982-10-12	Method for preparing methacrolein
US4190608A (en)	1980-02-26	Process for the oxidation of olefins using catalysts containing various promoter elements
US4306090A (en)	1981-12-15	Catalyst compositions and their use for the preparation of methacrolein
US4101448A (en)	1978-07-18	Catalyst compositions especially useful for preparation of unsaturated acids
US4316855A (en)	1982-02-23	Multiply promoted Sn-Sb oxide catalysts
US4174354A (en)	1979-11-13	Oxidative dehydrogenation using chromium-containing catalysts
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
US4558029A (en)	1985-12-10	Antimony-containing C4 oxidation catalysts
US4178464A (en)	1979-12-11	Process for producing methacrylic acid
US4209640A (en)	1980-06-24	Catalysts for the oxidation of unsaturated aldehydes
US4245118A (en)	1981-01-13	Oxidation of unsaturated aldehydes