CS215020B2 - Method of making the metacryl acid - Google Patents

Method of making the metacryl acid Download PDF

Info

Publication number: CS215020B2
Authority: CS; Czechoslovakia
Prior art keywords: catalyst; isobutylene; methacrolein; heteropolyacid; reaction
Prior art date: 1979-03-22

Application number

CS801954A

Other languages

Czech (cs)

English (en)

Inventor

Mutsumi Matsumoto

Kouichi Wada

Original Assignee

Nippon Kayaku Kk

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.)

1979-03-22

Filing date

1980-03-21

Publication date

1982-06-25

1980-03-21 Application filed by Nippon Kayaku Kk filed Critical Nippon Kayaku Kk

1982-06-25 Publication of CS215020B2 publication Critical patent/CS215020B2/cs

Links

238000004519 manufacturing process Methods 0.000 title claims description 11
239000002253 acid Substances 0.000 title description 10
239000003054 catalyst Substances 0.000 claims abstract description 62
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 40
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims abstract description 34
239000011964 heteropoly acid Substances 0.000 claims abstract description 33
238000000034 method Methods 0.000 claims abstract description 29
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 25
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 25
238000007254 oxidation reaction Methods 0.000 claims abstract description 23
230000003647 oxidation Effects 0.000 claims abstract description 15
229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 10
239000001301 oxygen Substances 0.000 claims abstract description 10
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
239000012808 vapor phase Substances 0.000 claims abstract description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 7
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052802 copper Inorganic materials 0.000 claims abstract description 7
239000010949 copper Substances 0.000 claims abstract description 7
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 7
239000011733 molybdenum Substances 0.000 claims abstract description 7
239000011574 phosphorus Substances 0.000 claims abstract description 7
229910052720 vanadium Inorganic materials 0.000 claims abstract description 7
239000007789 gas Substances 0.000 claims abstract description 6
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 13
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
229910052785 arsenic Inorganic materials 0.000 claims description 6
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 6
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
229910052797 bismuth Inorganic materials 0.000 claims description 4
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 4
229910052732 germanium Inorganic materials 0.000 claims description 4
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
229910052702 rhenium Inorganic materials 0.000 claims description 4
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 4
229910052718 tin Inorganic materials 0.000 claims description 4
229910052726 zirconium Inorganic materials 0.000 claims description 4
229910052742 iron Inorganic materials 0.000 claims description 3
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
229910052776 Thorium Inorganic materials 0.000 claims description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
229910052792 caesium Inorganic materials 0.000 claims description 2
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
239000011133 lead Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052701 rubidium Inorganic materials 0.000 claims description 2
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
229910052716 thallium Inorganic materials 0.000 claims description 2
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
229910052719 titanium Inorganic materials 0.000 claims description 2
239000010936 titanium Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
229910052774 Proactinium Inorganic materials 0.000 claims 1
229910052727 yttrium Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 description 14
230000000052 comparative effect Effects 0.000 description 11
230000000694 effects Effects 0.000 description 8
238000002441 X-ray diffraction Methods 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
239000007858 starting material Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
208000012839 conversion disease Diseases 0.000 description 4
239000000243 solution Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
238000001354 calcination Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
239000005751 Copper oxide Substances 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-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
230000015572 biosynthetic process Effects 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
229910000431 copper oxide Inorganic materials 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
125000005395 methacrylic acid group Chemical group 0.000 description 2
JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910001935 vanadium oxide Inorganic materials 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
239000011609 ammonium molybdate Substances 0.000 description 1
229940010552 ammonium molybdate Drugs 0.000 description 1
235000018660 ammonium molybdate Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229940000488 arsenic acid Drugs 0.000 description 1
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
229910000416 bismuth oxide Inorganic materials 0.000 description 1
229910002090 carbon oxide Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910000428 cobalt oxide Inorganic materials 0.000 description 1
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
229940112669 cuprous oxide Drugs 0.000 description 1
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
-1 for example Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 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
239000007788 liquid Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-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
DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910003449 rhenium oxide Inorganic materials 0.000 description 1
229930195734 saturated hydrocarbon Natural products 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
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
229910003452 thorium oxide Inorganic materials 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—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
- B01J23/88—Molybdenum
- B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8877—Vanadium, tantalum, niobium or polonium
- 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
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
- B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS801954A 1979-03-22 1980-03-21 Method of making the metacryl acid CS215020B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3232379A JPS55124734A (en)	1979-03-22	1979-03-22	Preparation of methacrylic acid

Publications (1)

Publication Number	Publication Date
CS215020B2 true CS215020B2 (en)	1982-06-25

Family

ID=12355725

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS801954A CS215020B2 (en)	1979-03-22	1980-03-21	Method of making the metacryl acid

Country Status (11)

Country	Link
US (1)	US4652673A (de)
JP (1)	JPS55124734A (de)
BE (1)	BE882303A (de)
CS (1)	CS215020B2 (de)
DE (1)	DE3010434A1 (de)
ES (1)	ES490544A0 (de)
FR (1)	FR2451907B1 (de)
GB (1)	GB2046252B (de)
IT (1)	IT1195265B (de)
NL (1)	NL8001507A (de)
SU (1)	SU1246889A3 (de)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
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JPS59115750A (ja) *	1982-12-22	1984-07-04	Nippon Shokubai Kagaku Kogyo Co Ltd	メタクリル酸合成用触媒
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DE3508649A1 (de) *	1985-03-12	1986-09-18	Röhm GmbH, 6100 Darmstadt	Heteropolysaeure h(pfeil abwaerts)8(pfeil abwaerts)pmo(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)0(pfeil abwaerts)vo(pfeil abwaerts)3(pfeil abwaerts)(pfeil abwaerts)9(pfeil abwaerts), deren anhydrid pmo(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)0(pfeil abwaerts)vo(pfeil abwaerts)3(pfeil abwaerts)(pfeil abwaerts)5(pfeil abwaerts)und ihre verwendung
JPH0791212B2 (ja) *	1988-07-11	1995-10-04	三菱レイヨン株式会社	メタクリル酸の製造法
DE3844087A1 (de) *	1988-12-28	1990-07-05	Basf Ag	Verfahren zur herstellung von methacrylsaeure durch oxidation von methacrolein
EP0415347B2 (de) *	1989-08-29	2002-06-05	Nippon Shokubai Kagaku Kogyo Co. Ltd.	Katalysator zur Herstellung von Methacrylsäure
DE4113423A1 (de) *	1991-04-25	1992-10-29	Roehm Gmbh	Mit makroporen durchsetzter oxidationskatalysator
DE4240085A1 (de) *	1992-11-28	1994-06-01	Roehm Gmbh	Katalytische Oxidation von Isobutan zu Methacrylsäure und Methacrolein
MY144325A (en) *	2003-02-20	2011-08-29	Nippon Kayaku Kk	Catalyst for producing methacrylic acid and preparation method thereof
JP4421558B2 (ja) *	2003-05-30	2010-02-24	日本化薬株式会社	メタクリル酸製造用触媒の製造方法
US7851397B2 (en) *	2005-07-25	2010-12-14	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
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
US7732367B2 (en) *	2005-07-25	2010-06-08	Saudi Basic Industries Corporation	Catalyst for methacrolein oxidation and method for making and using same
KR100807972B1 (ko) *	2005-08-10	2008-02-28	주식회사 엘지화학	아크릴산 선택성이 높은 복합 금속 산화물 촉매
US7799946B2 (en) *	2007-02-14	2010-09-21	Saudi Basic Industries Corporation	Process for separating methacrolein from methacrylic acid in a gas phase product from the partial oxidation of isobutene
EP1995232B1 (de)	2007-05-25	2018-01-03	Evonik Röhm GmbH	Verwendung von Hilfsstoffzusammensetzungen bei der Herstellung von Methacrlysäure durch Oxidation
EP2085376B1 (de)	2008-01-30	2012-09-05	Evonik Röhm GmbH	Verfahren zur Herstellung hochreiner Methacrylsäure
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
JP5892826B2 (ja) *	2012-03-27	2016-03-23	住友化学株式会社	メタクリル酸の製造方法
WO2013163806A1 (en)	2012-05-03	2013-11-07	Evonik Industries Ag	Process for preparation of highly pure, non-yellowing methacrylic acid
JP2016516732A (ja)	2013-03-18	2016-06-09	エボニックレームゲゼルシャフトミットベシュレンクテルハフツングＥｖｏｎｉｋＲｏｅｈｍＧｍｂＨ	メタクリル酸及びメタクリル酸エステルの製造方法
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DD148728A5 (de) *	1978-12-13	1981-06-10	Nippon Kayaku Kk	Verfahren zur herstellung eines katalysators mit heteropolysaeurestruktur

1979
- 1979-03-22 JP JP3232379A patent/JPS55124734A/ja active Pending
1980
- 1980-03-06 GB GB8007725A patent/GB2046252B/en not_active Expired
- 1980-03-13 NL NL8001507A patent/NL8001507A/nl not_active Application Discontinuation
- 1980-03-19 DE DE19803010434 patent/DE3010434A1/de not_active Ceased
- 1980-03-19 FR FR8006172A patent/FR2451907B1/fr not_active Expired
- 1980-03-19 BE BE0/199849A patent/BE882303A/fr not_active IP Right Cessation
- 1980-03-21 ES ES490544A patent/ES490544A0/es active Granted
- 1980-03-21 CS CS801954A patent/CS215020B2/cs unknown
- 1980-03-21 IT IT20829/80A patent/IT1195265B/it active
- 1980-03-21 SU SU802896304A patent/SU1246889A3/ru active
1983
- 1983-05-18 US US06/484,620 patent/US4652673A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS55124734A (en)	1980-09-26
FR2451907A1 (fr)	1980-10-17
FR2451907B1 (fr)	1986-10-24
ES8103014A1 (es)	1981-02-16
GB2046252B (en)	1983-05-11
NL8001507A (nl)	1980-09-24
IT1195265B (it)	1988-10-12
US4652673A (en)	1987-03-24
BE882303A (fr)	1980-09-19
GB2046252A (en)	1980-11-12
ES490544A0 (es)	1981-02-16
SU1246889A3 (ru)	1986-07-23
IT8020829A0 (it)	1980-03-21
DE3010434A1 (de)	1980-11-20

Publication	Publication Date	Title
CS215020B2 (en)	1982-06-25	Method of making the metacryl acid
CA1125785A (en)	1982-06-15	Process for producing methacrolein and methacrylic acid
EP0043100B2 (de)	1989-01-25	Oxidationskatalysator und Verfahren zu seiner Herstellung
US6169202B1 (en)	2001-01-02	Wells-Dawson type heteropolyacids, their preparation and use as oxidation catalysts
US4180678A (en)	1979-12-25	Process for preparing methacrylic acid
EP0006248A1 (de)	1980-01-09	Verfahren zur Herstellung von Methacrylsäure und Katalysator
US4467113A (en)	1984-08-21	Process for producing methacrylic acid
EP0771781B1 (de)	2000-04-05	Umwandlung von Alkanen zu ungesättigten Carboxylsäuren
US4273676A (en)	1981-06-16	Process for producing methacrylic acid and a catalyst
US4225466A (en)	1980-09-30	Catalytic oxide composition for preparing methacrylic acid
JPS5827255B2 (ja)	1983-06-08	不飽和脂肪酸の製造方法
JPS5826329B2 (ja)	1983-06-02	フホウワシボウサンノセイゾウホウ
EP0424900B1 (de)	1994-06-08	Verfahren zur Herstellung von Katalysatoren zur Herstellung der Methacrylsäure
KR840000985B1 (ko)	1984-07-13	비스무스―함유 메타크롤레인 산화용 촉매조성물
KR0131336B1 (ko)	1998-04-13	메타크릴산의 제조방법
US4172051A (en)	1979-10-23	Catalyst for producing methacrylic acid
EP0005769A1 (de)	1979-12-12	Verfahren zur Herstellung von Methacrolein und Methacrylsäure
JPS6230177B2 (de)	1987-07-01
JP2558036B2 (ja)	1996-11-27	メタクロレインおよび／またはメタクリル酸の製造方法
JP3316881B2 (ja)	2002-08-19	メタクリル酸製造用触媒の製造方法
US4347163A (en)	1982-08-31	Te-containing methacrolein oxidation catalysts and their use
JPS6033539B2 (ja)	1985-08-03	酸化用触媒およびその調製法
EP0634210B1 (de)	1998-06-17	Verfahren zur Herstellung eines Katalysators für die Zubereitung von Methacrylsäure
US4358610A (en)	1982-11-09	Process for the production of methacrylic acid from isobutyraldehyde
JPH029014B2 (de)	1990-02-28