NO772723L - Fremgangsm}te ved fremstilling av methacrylderivater frai t-butylholdige forbindelser - Google Patents

Fremgangsm}te ved fremstilling av methacrylderivater frai t-butylholdige forbindelser

Info

Publication number: NO772723L
Authority: NO; Norway
Prior art keywords: butyl; isobutylene; mixtures; catalyst; containing compound
Prior art date: 1976-08-02

Application number

NO772723A

Other languages

English (en)

Norwegian (no)

Inventor

Harley Foch Hardman

Robert Karl Grasselli

James Louis Callahan

Original Assignee

Standard Oil Co Ohio

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.)

1976-08-02

Filing date

1977-08-01

Publication date

1978-02-03

1977-08-01 Application filed by Standard Oil Co Ohio filed Critical Standard Oil Co Ohio

1978-02-03 Publication of NO772723L publication Critical patent/NO772723L/no

Links

238000000034 method Methods 0.000 title claims description 31
150000001875 compounds Chemical class 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title description 10
-1 METHACRYL Chemical class 0.000 title 1
239000003054 catalyst Substances 0.000 claims description 35
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 32
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 24
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
229910021529 ammonia Inorganic materials 0.000 claims description 12
239000013638 trimer Substances 0.000 claims description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
229910052787 antimony Inorganic materials 0.000 claims description 6
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 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 compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
229910001882 dioxygen Inorganic materials 0.000 claims description 6
229910052759 nickel Inorganic materials 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 5
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
229910052684 Cerium Inorganic materials 0.000 claims description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
229910052776 Thorium Inorganic materials 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
229910052785 arsenic Inorganic materials 0.000 claims description 3
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
229910052788 barium Inorganic materials 0.000 claims description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
229910052796 boron Inorganic materials 0.000 claims description 3
229910052793 cadmium Inorganic materials 0.000 claims description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
229910052792 caesium Inorganic materials 0.000 claims description 3
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 3
229910052804 chromium Inorganic materials 0.000 claims description 3
239000011651 chromium Substances 0.000 claims description 3
239000010949 copper Substances 0.000 claims description 3
229910052802 copper Inorganic materials 0.000 claims description 3
229910052732 germanium Inorganic materials 0.000 claims description 3
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
229910052738 indium Inorganic materials 0.000 claims description 3
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
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 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910052758 niobium Inorganic materials 0.000 claims description 3
239000010955 niobium Substances 0.000 claims description 3
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 3
229910052701 rubidium Inorganic materials 0.000 claims description 3
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 3
229910052709 silver Inorganic materials 0.000 claims description 3
239000004332 silver Substances 0.000 claims description 3
229910052712 strontium Inorganic materials 0.000 claims description 3
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 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
229910052718 tin Inorganic materials 0.000 claims description 3
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
229910052721 tungsten Inorganic materials 0.000 claims description 3
239000010937 tungsten Substances 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
229910052726 zirconium Inorganic materials 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
239000007858 starting material Substances 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
239000000243 solution Substances 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003570 air Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000001354 calcination Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
229910002016 Aerosil® 200 Inorganic materials 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000005201 scrubbing Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 1
LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
DTDQFVRSJWCWNK-UHFFFAOYSA-N [Fe].[Bi].[Mo] Chemical compound [Fe].[Bi].[Mo] DTDQFVRSJWCWNK-UHFFFAOYSA-N 0.000 description 1
150000004645 aluminates Chemical class 0.000 description 1
VIJYFGMFEVJQHU-UHFFFAOYSA-N aluminum oxosilicon(2+) oxygen(2-) Chemical compound [O-2].[Al+3].[Si+2]=O VIJYFGMFEVJQHU-UHFFFAOYSA-N 0.000 description 1
QGAVSDVURUSLQK-UHFFFAOYSA-N ammonium heptamolybdate Chemical compound N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 description 1
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
239000001273 butane Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-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
239000003701 inert diluent Substances 0.000 description 1
229910052816 inorganic phosphate Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
150000004760 silicates 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
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002912 waste gas Substances 0.000 description 1
229910001928 zirconium oxide Inorganic materials 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
- B01J23/88—Molybdenum
- B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8876—Arsenic, antimony or bismuth
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- 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
- 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
- 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
- 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
- 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
- C07C45/37—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 >C—O—functional groups to >C=O 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
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol 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
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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

NO772723A 1976-08-02 1977-08-01 Fremgangsm}te ved fremstilling av methacrylderivater frai t-butylholdige forbindelser NO772723L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/711,014 US4065507A (en)	1976-08-02	1976-08-02	Preparation of methacrylic derivatives from tertiary butyl-containing compounds

Publications (1)

Publication Number	Publication Date
NO772723L true NO772723L (no)	1978-02-03

Family

ID=24856442

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO772723A NO772723L (no)	1976-08-02	1977-08-01	Fremgangsm}te ved fremstilling av methacrylderivater frai t-butylholdige forbindelser

Country Status (19)

Country	Link
US (1)	US4065507A (de)
JP (1)	JPS5318508A (de)
AT (1)	AT358002B (de)
BE (1)	BE857324A (de)
BR (1)	BR7704883A (de)
CA (1)	CA1113498A (de)
CH (2)	CH635056A5 (de)
CS (2)	CS194845B2 (de)
DD (2)	DD132860A5 (de)
DE (1)	DE2732952C2 (de)
ES (2)	ES461227A1 (de)
FR (1)	FR2360545A1 (de)
GB (1)	GB1564459A (de)
IT (1)	IT1085664B (de)
MX (1)	MX147440A (de)
NL (1)	NL7708493A (de)
NO (1)	NO772723L (de)
PT (1)	PT66875B (de)
YU (1)	YU190277A (de)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4111984A (en) *	1973-06-11	1978-09-05	Mitsubishi Rayon Co., Ltd.	Process for producing unsaturated aldehydes, and unsaturated fatty acids
IL55073A (en) *	1977-07-28	1982-01-31	Standard Oil Co	Catalysts for the oxidation and ammoxidation of olefins
CA1133505A (en) *	1977-07-28	1982-10-12	Andrew T. Guttmann	Process for the oxidation of olefins
US4230640A (en) *	1977-11-01	1980-10-28	Halcon International, Inc.	Process for the preparation of acrolein and methacrolein
JPS584691B2 (ja) *	1977-11-07	1983-01-27	宇部興産株式会社	メタクロレインの製造方法
GB2033775B (en) *	1978-10-13	1983-02-09	Asahi Chemical Ind	Catalysts and process for the production of methacrolein catalysts
US4230639A (en) *	1979-01-19	1980-10-28	Halcon International, Inc.	Process for the preparation of methacrolein
US4306090A (en) *	1979-10-12	1981-12-15	Rohm And Haas Company	Catalyst compositions and their use for the preparation of methacrolein
US4358622A (en) *	1979-10-12	1982-11-09	Rohm And Haas Company	Preparation of methacrolein and methacrylonitrile from tert-butyl alkanoates
US4280928A (en) *	1979-10-12	1981-07-28	Rohm And Haas Company	Catalyst compositions and their use for the preparation of methacrolein
JPS56166140A (en) *	1980-05-24	1981-12-21	Asahi Chem Ind Co Ltd	Preparation of methacrolein
US4446328A (en) *	1980-05-19	1984-05-01	Asahi Kasei Kogyo Kabushiki Kaisha	Process for producing methacrolein
JPS5728012A (en) *	1980-07-25	1982-02-15	Mitsubishi Gas Chem Co Inc	Preparation of tertiary olefin
US4443383A (en) *	1981-03-19	1984-04-17	Rohm And Haas Company	Preparation of methacrolein and methacrylonitrile from tert-butyl alkanoates
US4537998A (en) *	1981-04-27	1985-08-27	Atlantic Richfield Company	Process for the oxidation of isobutylene oxide to methacrolein
US4558154A (en) *	1981-04-27	1985-12-10	Atlantic Richfield Company	Oxidation of isobutylene oxide to methacrylic acid and methacrolein
US4474997A (en) *	1982-07-06	1984-10-02	E. I. Du Pont De Nemours And Company	Oxidation process and catalyst therefor
JPS6122040A (ja) *	1984-07-10	1986-01-30	Mitsubishi Rayon Co Ltd	メタクロレイン及びメタクリル酸の製造法
JPH07116070B2 (ja) *	1987-08-26	1995-12-13	株式会社日本触媒	メチルタ−シャリ−ブチルエ−テルからメタクロレインおよびメタクリル酸の製法
JP2520279B2 (ja) *	1988-03-03	1996-07-31	日東化学工業株式会社	アクリロニトリルの製造方法
US7732367B2 (en)	2005-07-25	2010-06-08	Saudi Basic Industries Corporation	Catalyst for methacrolein oxidation and method for making and using same
US7649112B2 (en)	2005-07-25	2010-01-19	Saudi Basic Industries Corporation	Integrated plant for producing 2-ethyl-hexanol and methacrylic acid and a method based thereon
US7851397B2 (en)	2005-07-25	2010-12-14	Saudi Basic Industries Corporation	Catalyst for methacrolein oxidation and method for making and using same
US7649111B2 (en)	2005-07-25	2010-01-19	Saudi Basic Industries Corporation	Catalyst for the oxidation of a mixed aldehyde feedstock to methacrylic acid and methods for making and using same
US8921257B2 (en)	2011-12-02	2014-12-30	Saudi Basic Industries Corporation	Dual function partial oxidation catalyst for propane to acrylic acid conversion
US8722940B2 (en)	2012-03-01	2014-05-13	Saudi Basic Industries Corporation	High molybdenum mixed metal oxide catalysts for the production of unsaturated aldehydes from olefins

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1018799A (fr) *	1949-03-25	1953-01-13	Distillers Co Yeast Ltd	Nouveaux composés organiques oxygénés
US3470239A (en) *	1968-06-07	1969-09-30	Halcon International Inc	Process for preparing methacrylic acid and its esters from isobutane
US3642930A (en) *	1968-12-30	1972-02-15	Standard Oil Co Ohio	Process for the manufacture of isoprene from isoamylenes and methyl butanols and catalyst therefor
BE755422A (fr) *	1969-09-08	1971-03-01	Inst Francais Du Petrole	Fabrication de catalyseurs du type molybdate de fer utilisablesnotamment pour l'oxydation catalytique des alcools en
JPS5112603B1 (de) *	1971-05-26	1976-04-21
US3972920A (en) *	1973-06-11	1976-08-03	Mitsubishi Rayon Co., Ltd.	Process for producing unsaturated aldehydes, unsaturated fatty acids or conjugated dienes
JPS5163112A (en) *	1974-11-27	1976-06-01	Nippon Kayaku Kk	Metakuroreinno seizoho
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
JPS5939413B2 (ja) *	1975-04-08	1984-09-22	三菱レイヨン株式会社	メタクロレインとメタクリル酸の製造方法

1976
- 1976-08-02 US US05/711,014 patent/US4065507A/en not_active Expired - Lifetime
1977
- 1977-07-15 CA CA282,896A patent/CA1113498A/en not_active Expired
- 1977-07-21 DE DE2732952A patent/DE2732952C2/de not_active Expired
- 1977-07-25 GB GB31076/77A patent/GB1564459A/en not_active Expired
- 1977-07-26 BR BR7704883A patent/BR7704883A/pt unknown
- 1977-07-27 JP JP9024177A patent/JPS5318508A/ja active Pending
- 1977-07-28 AT AT555377A patent/AT358002B/de not_active IP Right Cessation
- 1977-07-29 CS CS782906A patent/CS194845B2/cs unknown
- 1977-07-29 CS CS775036A patent/CS194814B2/cs unknown
- 1977-07-29 FR FR7723447A patent/FR2360545A1/fr active Pending
- 1977-07-29 DD DD7700200356A patent/DD132860A5/de unknown
- 1977-07-29 CH CH942877A patent/CH635056A5/de not_active IP Right Cessation
- 1977-07-29 BE BE179784A patent/BE857324A/xx not_active IP Right Cessation
- 1977-07-29 DD DD77207071A patent/DD137582A5/de unknown
- 1977-08-01 NO NO772723A patent/NO772723L/no unknown
- 1977-08-01 PT PT66875A patent/PT66875B/pt unknown
- 1977-08-01 IT IT26381/77A patent/IT1085664B/it active
- 1977-08-01 ES ES461227A patent/ES461227A1/es not_active Expired
- 1977-08-01 NL NL7708493A patent/NL7708493A/xx not_active Application Discontinuation
- 1977-08-01 MX MX170061A patent/MX147440A/es unknown
- 1977-08-02 YU YU01902/77A patent/YU190277A/xx unknown
- 1977-10-06 ES ES462969A patent/ES462969A1/es not_active Expired
1982
- 1982-02-18 CH CH103082A patent/CH635315A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
YU190277A (en)	1983-01-21
JPS5318508A (en)	1978-02-20
FR2360545A1 (fr)	1978-03-03
IT1085664B (it)	1985-05-28
ES462969A1 (es)	1978-06-16
CS194845B2 (en)	1979-12-31
DE2732952C2 (de)	1987-02-12
BE857324A (fr)	1977-11-14
CS194814B2 (en)	1979-12-31
DD137582A5 (de)	1979-09-12
AT358002B (de)	1980-08-11
PT66875B (en)	1979-01-23
ATA555377A (de)	1980-01-15
PT66875A (en)	1977-09-01
GB1564459A (en)	1980-04-10
NL7708493A (nl)	1978-02-06
US4065507A (en)	1977-12-27
MX147440A (es)	1982-12-03
DE2732952A1 (de)	1978-02-09
BR7704883A (pt)	1978-06-13
CH635056A5 (de)	1983-03-15
ES461227A1 (es)	1978-12-01
CH635315A5 (de)	1983-03-31
CA1113498A (en)	1981-12-01
DD132860A5 (de)	1978-11-15

Publication	Publication Date	Title
NO772723L (no)	1978-02-03	Fremgangsm}te ved fremstilling av methacrylderivater frai t-butylholdige forbindelser
US3642930A (en)	1972-02-15	Process for the manufacture of isoprene from isoamylenes and methyl butanols and catalyst therefor
US5134105A (en)	1992-07-28	Catalyst for propylene ammoxidation to acrylonitrile
Sofranko et al.	1988	Catalytic oxidative coupling of methane over sodium-promoted Mn/SiO2 and Mn/MgO
US4155938A (en)	1979-05-22	Oxidation of olefins
US5235088A (en)	1993-08-10	Process and catalyst for propylene ammoxidation to acrylonitrile
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
US4182907A (en)	1980-01-08	Process for the oxidation of olefins to aldehydes and acids
JPH0149542B2 (de)	1989-10-25
NO328001B1 (no)	2009-11-09	Fremgangsmate og katalysator for selektiv fremstilling av eddiksyre ved katalytisk oksydasjon av etan og/eller etylen
US4620035A (en)	1986-10-28	Production of acrylic acid by oxidation of acrolein
US4323703A (en)	1982-04-06	Process for the oxidation of olefins to aldehydes and acids
US4323520A (en)	1982-04-06	Preparation of methacrylic derivatives from tertiary-butyl-containing compounds
US3576764A (en)	1971-04-27	Catalyst for the oxidation of olefins to unsaturated aldehydes and acids
JP2013121559A (ja)	2013-06-20	１，３−ブタジエン及びメタクロレイン同時製造用触媒、並びにそれを用いた１，３−ブタジエン及びメタクロレインの製造方法
NO147068B (no)	1982-10-18	Fremgangsmaate for fremstilling av akrylsyre og metakrylsyre ved omsetning av propylen eller isobutylen med molekylaer oksygen
NO148936B (no)	1983-10-03	Dampfelle med frittflytende flottoer
JPS6048496B2 (ja)	1985-10-28	メタクリル酸の製造方法
JPS5838424B2 (ja)	1983-08-23	オレフインアンモニアオヨビサンソカラフホウワニトリルオセイゾウスルセツシヨクホウ
JPH0678251B2 (ja)	1994-10-05	メタクリル酸および／またはメタクロレインの製造方法
Guo et al.	2008	One-step synthesis of methylmethacrylate from methacrolein over Keggin-type heteropoly compounds
US4255602A (en)	1981-03-10	Stilbene formation by means of toluene dehydrocoupling using a cobalt-lanthanide catalyst
US3259652A (en)	1966-07-05	Oxidation of acrolein or methacrolein to the corresponding acid in the presence of an sn-sb-mo catalyst
USRE32484E (en)	1987-08-25	Oxidation catalysts