CH428695A - Verfahren zur Herstellung von Acrolein oder Methacrolein durch katalytische Oxydation von Propylen oder Isobutylen - Google Patents

Verfahren zur Herstellung von Acrolein oder Methacrolein durch katalytische Oxydation von Propylen oder Isobutylen

Info

Publication number: CH428695A
Authority: CH; Switzerland
Prior art keywords: catalyst; antimony; vanadium; acrolein; propylene
Prior art date: 1961-03-06

Application number

CH265562A

Other languages

German (de)

English (en)

Inventor

Phielix Bernard

Bonnema Jentje

Original Assignee

Stamicarbon

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.)

1961-03-06

Filing date

1962-03-05

Publication date

1967-01-31

1962-03-05 Application filed by Stamicarbon filed Critical Stamicarbon

1962-10-29 Priority to CH1269562A priority Critical patent/CH453326A/de

1967-01-31 Publication of CH428695A publication Critical patent/CH428695A/de

Links

HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims description 44
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims description 21
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims description 21
238000000034 method Methods 0.000 title claims description 20
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 title claims description 19
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 17
238000007254 oxidation reaction Methods 0.000 title claims description 12
230000003647 oxidation Effects 0.000 title claims description 11
230000003197 catalytic effect Effects 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title claims description 5
239000003054 catalyst Substances 0.000 claims description 64
239000007789 gas Substances 0.000 claims description 30
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 22
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 22
229910052787 antimony Inorganic materials 0.000 claims description 19
229910052720 vanadium Inorganic materials 0.000 claims description 17
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
229910052797 bismuth Inorganic materials 0.000 claims description 13
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
229910052698 phosphorus Inorganic materials 0.000 claims description 13
239000011574 phosphorus Substances 0.000 claims description 13
229910001392 phosphorus oxide Inorganic materials 0.000 claims description 7
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 7
229910001935 vanadium oxide Inorganic materials 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 4
229910010271 silicon carbide Inorganic materials 0.000 claims description 4
150000001462 antimony Chemical class 0.000 claims description 3
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 claims description 2
150000001621 bismuth Chemical class 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
229910000416 bismuth oxide Inorganic materials 0.000 claims 1
TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 31
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
229910002092 carbon dioxide Inorganic materials 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229910000410 antimony oxide Inorganic materials 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
230000000284 resting effect Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 3
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 3
WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(iii) oxide Chemical compound O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
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 3
230000001590 oxidative effect Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
229910002012 Aerosil® Inorganic materials 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
QORUGWXKGWRLBB-UHFFFAOYSA-N 2-methylprop-1-ene;2-methylprop-2-enoic acid Chemical compound CC(C)=C.CC(=C)C(O)=O QORUGWXKGWRLBB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
-1 B. by known methods Chemical compound 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
LQCUOGOFJLPCNN-UHFFFAOYSA-N acetaldehyde prop-1-ene Chemical compound O=CC.C=CC LQCUOGOFJLPCNN-UHFFFAOYSA-N 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
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 1
229910000149 boron phosphate Inorganic materials 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
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 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
CJJMLLCUQDSZIZ-UHFFFAOYSA-N oxobismuth Chemical class [Bi]=O CJJMLLCUQDSZIZ-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
WQIJNCUKAOHNPM-UHFFFAOYSA-L silver selenite Chemical compound [Ag+].[Ag+].[O-][Se]([O-])=O WQIJNCUKAOHNPM-UHFFFAOYSA-L 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- B01J23/835—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 germanium, tin or lead
- 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
- B01J23/20—Vanadium, niobium or tantalum
- B01J23/22—Vanadium
- 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
- 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)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CH265562A 1961-03-06 1962-03-05 Verfahren zur Herstellung von Acrolein oder Methacrolein durch katalytische Oxydation von Propylen oder Isobutylen CH428695A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1269562A CH453326A (de)	1962-03-05	1962-10-29	Verfahren zur Herstellung von Methacrolein durch katalytische Oxydation von Isobutylen

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL262006		1961-03-06
NL273489		1962-01-12

Publications (1)

Publication Number	Publication Date
CH428695A true CH428695A (de)	1967-01-31

Family

ID=26641764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH265562A CH428695A (de)	1961-03-06	1962-03-05	Verfahren zur Herstellung von Acrolein oder Methacrolein durch katalytische Oxydation von Propylen oder Isobutylen

Country Status (5)

Country	Link
BE (1)	BE614584A (fr)
CH (1)	CH428695A (fr)
DE (1)	DE1177628B (fr)
ES (1)	ES275172A1 (fr)
GB (1)	GB969369A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1238891B (de) *	1962-07-09	1967-04-20	Chemical Investors Sa	Verfahren zur Herstellung von Methacrolein
DE1243664B (de) *	1962-10-31	1967-07-06	Edison Soc	Verfahren zur Herstellung ungesaettigter Aldehyde durch katalytische Oxydation von Olefinkohlenwasserstoffen
GB991085A (en) *	1963-06-11	1965-05-05	Distillers Co Yeast Ltd	Improvements in or relating to the production of unsaturated aliphatic aldehydes
WO2005113138A1 (fr) *	2004-05-13	2005-12-01	E.I. Dupont De Nemours And Company	Phosphate d'antimoine vanadium
WO2013137934A1 (fr) *	2012-03-13	2013-09-19	Celanese International Corporation	Catalyseur pour produire des acides acryliques et des acrylates

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1070612B (de) *		1959-12-10	Arum.: N. V. De Bataafsche Petroleum Maat'schappij, Den Haag; Ventr.: Dt K. Schwarzhans, Pat.-Anw., München 19	Verfahren zur Herstellung eines Katalysators für die Oxydation von olefinischen Kohlenwasserstoffen zu olefinischen Carbonylverbindungen
US2451485A (en) *	1947-09-27	1948-10-19	Shell Dev	Production of unsaturated carbonylic compounds
US2941007A (en) *	1957-06-10	1960-06-14	Standard Oil Co	Process for the oxidation of olefins
GB839808A (en) *	1957-06-21	1960-06-29	Bayer Ag	Process for the production of acrolein
DE1079615B (de) *	1957-06-21	1960-04-14	Bayer Ag	Verfahren zur Herstellung von Acrolein

1962
- 1962-03-01 BE BE614584A patent/BE614584A/fr unknown
- 1962-03-01 DE DE1962ST018918 patent/DE1177628B/de active Pending
- 1962-03-05 CH CH265562A patent/CH428695A/de unknown
- 1962-03-05 ES ES0275172A patent/ES275172A1/es not_active Expired
- 1962-03-06 GB GB869262A patent/GB969369A/en not_active Expired

Also Published As

Publication number	Publication date
BE614584A (fr)	1962-09-03
ES275172A1 (es)	1963-03-01
GB969369A (en)	1964-09-09
DE1177628B (de)	1964-09-10

Publication	Publication Date	Title
DE2759531C2 (fr)	1990-10-18
DE69210288T2 (de)	1996-10-10	Verfahren zur Herstellung von Methanolein und Verfahren zur Herstellung eines Katalysators zur Verwendung in dem Methacrolein-Verfahren
DE2704991C3 (de)	1981-07-02	Verfahren zur Herstellung von Methacrylsäure
DE2203709A1 (fr)	1972-08-17
DE2441109A1 (de)	1975-03-06	Verfahren zur katalytischen oxydation von tert.-butylalkohol in der dampfphase
DE2456100A1 (de)	1975-06-05	Verfahren zur herstellung von akrylsaeure durch katalytische oxydation von akrolein
DE2523757B2 (de)	1978-05-03	Verfahren zur Herstellung von Methacrylsäure durch katalytische Oxidation von Methacrolein mit Sauerstoff
DE2203710C3 (de)	1988-05-26	Verfahren zur Herstellung von ungesättigten Aldehyden und Säuren
DE69112262T2 (de)	1996-02-01	Verfahren zur Herstellung von Katalysatoren für die Herstellung von Methacrylsäure.
EP0255639B1 (fr)	1989-05-31	Mélanges d'hétéropolymolybdates et leur utilisation comme catalyseurs
DE2420281C2 (de)	1983-08-04	Verfahren zur Herstellung von Acrylsäure
DE2353131C3 (de)	1980-02-14	Katalysator fur die Gasphasenoxydation von ungesättigten Aldehyden zu ungesättigten Carbonsäuren
CH428695A (de)	1967-01-31	Verfahren zur Herstellung von Acrolein oder Methacrolein durch katalytische Oxydation von Propylen oder Isobutylen
DE1518729C3 (de)	1979-05-03	Verfahren zur Herstellung eines Gemisches aus Acrylsäure und Acrolein
DE1543294C3 (de)	1975-08-28	Verfahren zur Herstellung von Acrylsäure bzw. Methacrylsäure
DE2228989C3 (de)	1978-04-13	Molybdän, Eisen, Wismut, Nickel, Thallium sowie gegebenenfalls Magnesium, Mangan, Kobalt und Phosphor enthaltender Oxid-Trägerkatalysator und seine Verwendung zur Herstellung von Acrolein
DE2422796C2 (de)	1982-12-09	Verfahren zur Herstellung von Methyl- oder Äthylestern der Acryl- oder Methacrylsäure
DE1293736B (de)	1969-04-30	Verfahren zur Herstellung von Adipinsaeure
DE2203439B2 (de)	1975-05-07	Verfahren zur Herstellung von Acrylnitril aus Propylen
AT231418B (de)	1964-01-27	Verfahren zur Herstellung von Akrolein durch katalytische Oxydation von Propylen
DE1668335C3 (fr)	1974-07-18
AT235817B (de)	1964-09-25	Verfahren zur Herstellung von Essigsäure durch katalytische Oxydation von Propylen
AT225685B (de)	1963-02-11	Verfahren zur Herstellung von Maleinsäureanhydrid
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