CA1058146A - Method of manufacturing methacrylic acid and an oxidation catalyst - Google Patents

Method of manufacturing methacrylic acid and an oxidation catalyst

Info

Publication number: CA1058146A
Authority: CA; Canada
Prior art keywords: value; range; catalyst; methacrolein; reaction
Prior art date: 1974-09-24
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

CA236,080A

Other languages

English (en)

French (fr)

Inventor

Masanobu Ogawa

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.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co Ltd

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.)

1974-09-24

Filing date

1975-09-23

Publication date

1979-07-10

1974-09-24 Priority claimed from JP49108890A external-priority patent/JPS5136417A/ja

1974-09-24 Priority claimed from JP10888974A external-priority patent/JPS5136416A/ja

1975-09-23 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1979-07-10 Application granted granted Critical

1979-07-10 Publication of CA1058146A publication Critical patent/CA1058146A/en

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 63
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 17
238000007254 oxidation reaction Methods 0.000 title claims abstract description 14
230000003647 oxidation Effects 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title claims abstract description 8
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims abstract description 32
239000000203 mixture Substances 0.000 claims abstract description 18
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 15
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052788 barium Inorganic materials 0.000 claims abstract description 10
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052797 bismuth Inorganic materials 0.000 claims abstract description 10
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052787 antimony Inorganic materials 0.000 claims abstract description 8
229910052804 chromium Inorganic materials 0.000 claims abstract description 8
239000011651 chromium Substances 0.000 claims abstract description 8
229910052763 palladium Inorganic materials 0.000 claims abstract description 8
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052770 Uranium Inorganic materials 0.000 claims abstract description 7
229910017052 cobalt Inorganic materials 0.000 claims abstract description 7
239000010941 cobalt Substances 0.000 claims abstract description 7
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052742 iron Inorganic materials 0.000 claims abstract description 7
239000011133 lead Substances 0.000 claims abstract description 7
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 abstract description 7
229910052759 nickel Inorganic materials 0.000 claims abstract description 7
229910052718 tin Inorganic materials 0.000 claims abstract description 7
239000011135 tin Substances 0.000 claims abstract description 7
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims abstract 3
238000000034 method Methods 0.000 claims description 17
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
229910001882 dioxygen Inorganic materials 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000007789 gas Substances 0.000 description 15
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
229910052760 oxygen Inorganic materials 0.000 description 8
206010001497 Agitation Diseases 0.000 description 7
238000013019 agitation Methods 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 6
229910002092 carbon dioxide Inorganic materials 0.000 description 6
239000001569 carbon dioxide Substances 0.000 description 6
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 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
229910002091 carbon monoxide Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 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
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 3
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000001354 calcination Methods 0.000 description 3
239000011363 dried mixture Substances 0.000 description 3
229910052750 molybdenum Inorganic materials 0.000 description 3
239000011733 molybdenum Substances 0.000 description 3
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 3
239000011369 resultant mixture Substances 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-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
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
NLSCHDZTHVNDCP-UHFFFAOYSA-N caesium nitrate Chemical compound [Cs+].[O-][N+]([O-])=O NLSCHDZTHVNDCP-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000002131 composite material Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000002708 enhancing effect Effects 0.000 description 2
239000007792 gaseous phase Substances 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
125000005395 methacrylic acid group Chemical group 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000010703 silicon Substances 0.000 description 2
239000005049 silicon tetrachloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
MVWDJLOUEUAWIE-UHFFFAOYSA-N O=C=O.O=C=O Chemical compound O=C=O.O=C=O MVWDJLOUEUAWIE-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000002950 deficient Effects 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
FYWSTUCDSVYLPV-UHFFFAOYSA-N nitrooxythallium Chemical compound [Tl+].[O-][N+]([O-])=O FYWSTUCDSVYLPV-UHFFFAOYSA-N 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
-1 oxides Chemical class 0.000 description 1
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
RTHYXYOJKHGZJT-UHFFFAOYSA-N rubidium nitrate Inorganic materials [Rb+].[O-][N+]([O-])=O RTHYXYOJKHGZJT-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 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
239000004575 stone Substances 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
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
KHAUBYTYGDOYRU-IRXASZMISA-N trospectomycin Chemical compound CN[C@H]([C@H]1O2)[C@@H](O)[C@@H](NC)[C@H](O)[C@H]1O[C@H]1[C@]2(O)C(=O)C[C@@H](CCCC)O1 KHAUBYTYGDOYRU-IRXASZMISA-N 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
- 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
- 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
- B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
- B01J27/1856—Phosphorus; Compounds thereof with iron group metals or platinum group metals with platinum group metals
- 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

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)

CA236,080A 1974-09-24 1975-09-23 Method of manufacturing methacrylic acid and an oxidation catalyst Expired CA1058146A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP49108890A JPS5136417A (en)	1974-09-24	1974-09-24	Metakurirusan no seizoho
JP10888974A JPS5136416A (en)	1974-09-24	1974-09-24	Metakurirusan no seizoho

Publications (1)

Publication Number	Publication Date
CA1058146A true CA1058146A (en)	1979-07-10

Family

ID=26448702

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,080A Expired CA1058146A (en)	1974-09-24	1975-09-23	Method of manufacturing methacrylic acid and an oxidation catalyst

Country Status (7)

Country	Link
US (1)	US4042623A (2)
CA (1)	CA1058146A (2)
DE (1)	DE2541571C3 (2)
FR (1)	FR2285925A1 (2)
GB (1)	GB1521118A (2)
IT (1)	IT1042809B (2)
NL (1)	NL163767C (2)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5182215A (en) *	1975-01-16	1976-07-19	Nippon Kayaku Kk	Metakurirusan mataha akurirusanno seizoho
JPS5949215B2 (ja) *	1976-11-27	1984-12-01	日本化薬株式会社	メタクリル酸又はアクリル酸の製造方法
JPS58109442A (ja) *	1981-12-22	1983-06-29	Toa Nenryo Kogyo Kk	カルボニル化合物の製造方法
US4720474A (en) *	1985-09-24	1988-01-19	Catalytica Associates	Olefin oxidation catalyst system
US6337424B1 (en) *	2000-04-28	2002-01-08	Saudi Basic Industries Corporation	Catalysts oxidation of lower olefins to unsaturated aldehydes, methods of making and using the same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2438164A (en) *	1946-03-28	1948-03-23	Socony Vacuum Oil Co Inc	Process for the production of methacrylic acid
US3087964A (en) *	1959-05-25	1963-04-30	Du Pont	Vapor phase oxidation of acrolein to acrylic acid
US3541143A (en) *	1966-09-07	1970-11-17	Mitsubishi Petrochemical Co	Process for the preparation of acrylic acid
US3646127A (en) *	1968-08-01	1972-02-29	Japanese Geon Co Ltd	Process for the preparation of unsaturated carboxylic acid
US3792086A (en) *	1971-11-10	1974-02-12	Nat Distillers Chem Corp	Process for the preparation of acrylic and methacrylic acids
US3875220A (en) *	1973-10-11	1975-04-01	Standard Oil Co Ohio	Process for the preparation of methacrylic acid from methacrolein

1975
- 1975-09-16 US US05/613,921 patent/US4042623A/en not_active Expired - Lifetime
- 1975-09-18 DE DE2541571A patent/DE2541571C3/de not_active Expired
- 1975-09-19 FR FR7528730A patent/FR2285925A1/fr active Granted
- 1975-09-23 CA CA236,080A patent/CA1058146A/en not_active Expired
- 1975-09-23 NL NL7511186.A patent/NL163767C/xx not_active IP Right Cessation
- 1975-09-24 IT IT27570/75A patent/IT1042809B/it active
- 1975-09-24 GB GB39159/75A patent/GB1521118A/en not_active Expired

Also Published As

Publication number	Publication date
US4042623A (en)	1977-08-16
IT1042809B (it)	1980-01-30
NL163767B (nl)	1980-05-16
DE2541571C3 (de)	1980-09-11
DE2541571B2 (de)	1980-01-03
DE2541571A1 (de)	1976-04-01
FR2285925A1 (fr)	1976-04-23
FR2285925B1 (2)	1979-02-02
NL163767C (nl)	1980-10-15
GB1521118A (en)	1978-08-09
NL7511186A (nl)	1976-03-26

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EP0286448B2 (en)	1997-04-23	Process for the preparation of phthalic anhydride
US4051179A (en)	1977-09-27	Catalytic process for the preparation of unsaturated carboxylic acids
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