CA1046491A - Catalyseur d'oxydation et procede de preparation d'acides insatures et d'aldehydes - Google Patents

Catalyseur d'oxydation et procede de preparation d'acides insatures et d'aldehydes

Info

Publication number: CA1046491A
Authority: CA; Canada
Prior art keywords: catalyst; alpha; elements; silica; beta unsaturated
Prior art date: 1974-09-03
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

CA234,438A

Other languages

English (en)

Other versions

CA234438S (en

Inventor

Abraham N. Kurtz

Erlind M. Thorsteinson

Harry J. Decker

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1974-09-03

Filing date

1975-08-28

Publication date

1979-01-16

1975-08-25 Priority claimed from US05/606,973 external-priority patent/US4034008A/en

1975-08-28 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1979-01-16 Application granted granted Critical

1979-01-16 Publication of CA1046491A publication Critical patent/CA1046491A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 73
238000007254 oxidation reaction Methods 0.000 title claims abstract description 15
230000003647 oxidation Effects 0.000 title claims abstract description 14
238000004519 manufacturing process Methods 0.000 title claims 2
239000002253 acid Substances 0.000 title description 7
150000001299 aldehydes Chemical class 0.000 title description 6
150000007513 acids Chemical class 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 18
229910052742 iron Inorganic materials 0.000 claims abstract description 8
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 8
229910052759 nickel Inorganic materials 0.000 claims abstract description 6
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 5
239000012808 vapor phase Substances 0.000 claims abstract description 5
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
238000001354 calcination Methods 0.000 claims description 9
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 8
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
229910052787 antimony Inorganic materials 0.000 claims description 5
-1 unsaturated aliphatic aldehyde Chemical class 0.000 claims description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
229910052797 bismuth Inorganic materials 0.000 claims description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
239000004711 α-olefin Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 22
150000005673 monoalkenes Chemical class 0.000 abstract description 8
229910052710 silicon Inorganic materials 0.000 abstract description 4
230000001590 oxidative effect Effects 0.000 abstract description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
239000000203 mixture Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 12
150000002500 ions Chemical class 0.000 description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
239000007789 gas Substances 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 7
238000012360 testing method Methods 0.000 description 7
150000001336 alkenes Chemical class 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
239000008119 colloidal silica Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
229910001030 Iron–nickel alloy Inorganic materials 0.000 description 2
241000286904 Leptothecata Species 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
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 2
VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
150000002823 nitrates Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000003891 oxalate salts Chemical class 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000011148 porous material Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
JQPURQFIKQEPAR-UHFFFAOYSA-N C(C=CC)(=O)O.CC=CC Chemical compound C(C=CC)(=O)O.CC=CC JQPURQFIKQEPAR-UHFFFAOYSA-N 0.000 description 1
UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
101100091152 Mus musculus Rnf41 gene Proteins 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
238000012217 deletion Methods 0.000 description 1
230000037430 deletion Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
239000011551 heat transfer agent Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
SZQUEWJRBJDHSM-UHFFFAOYSA-N iron(3+);trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SZQUEWJRBJDHSM-UHFFFAOYSA-N 0.000 description 1
RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
239000005078 molybdenum compound Substances 0.000 description 1
150000002752 molybdenum compounds Chemical class 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
229940074096 monoolein Drugs 0.000 description 1
AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 1
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229940061319 ovide Drugs 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000007934 α,β-unsaturated carboxylic acids Chemical class 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
- B01J23/70—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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8993—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with chromium, molybdenum or tungsten
- 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
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
- 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)

CA234,438A 1974-09-03 1975-08-28 Catalyseur d'oxydation et procede de preparation d'acides insatures et d'aldehydes Expired CA1046491A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US50255074A	1974-09-03	1974-09-03
US05/606,973 US4034008A (en)	1975-08-25	1975-08-25	Process for preparing unsaturated acids and aldehydes

Publications (1)

Publication Number	Publication Date
CA1046491A true CA1046491A (fr)	1979-01-16

Family

ID=27054198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA234,438A Expired CA1046491A (fr)	1974-09-03	1975-08-28	Catalyseur d'oxydation et procede de preparation d'acides insatures et d'aldehydes

Country Status (7)

Country	Link
JP (1)	JPS5152114A (fr)
CA (1)	CA1046491A (fr)
DE (1)	DE2539060C3 (fr)
FR (1)	FR2329638A1 (fr)
GB (1)	GB1510854A (fr)
IT (1)	IT1044619B (fr)
NL (1)	NL182399C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0814959D0 (en) *	2008-08-15	2008-09-24	Pegler Ltd	Compact control head for a thermostatic valve
CN110280256A (zh) *	2019-07-10	2019-09-27	兰州科润化工技术有限公司	一种用于制备丙烯醛的催化剂及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2125032C3 (de) *	1970-05-26	1979-11-22	Nippon Catalytic Chem Ind	Verfahren zur Herstellung von (Meth) Acrolein neben geringen Mengen (Meth) Acrylsäure
DE2161471C3 (de) *	1970-12-26	1982-05-13	Nippon Shokubai Kagaku Kogyo Co. Ltd., Osaka	Verfahren zur Herstellung von Acrolein und Acrylsäure

1975
- 1975-08-28 CA CA234,438A patent/CA1046491A/fr not_active Expired
- 1975-09-03 DE DE19752539060 patent/DE2539060C3/de not_active Expired
- 1975-09-03 FR FR7527066A patent/FR2329638A1/fr active Granted
- 1975-09-03 NL NL7510393A patent/NL182399C/xx not_active IP Right Cessation
- 1975-09-03 JP JP10608775A patent/JPS5152114A/ja active Pending
- 1975-09-03 IT IT2689475A patent/IT1044619B/it active
- 1975-09-03 GB GB3623275A patent/GB1510854A/en not_active Expired

Also Published As

Publication number	Publication date
NL7510393A (nl)	1976-03-05
FR2329638B1 (fr)	1980-01-11
DE2539060A1 (de)	1976-03-11
JPS5152114A (ja)	1976-05-08
DE2539060C3 (de)	1982-06-16
FR2329638A1 (fr)	1977-05-27
GB1510854A (en)	1978-05-17
NL182399B (nl)	1987-10-01
NL182399C (nl)	1988-03-01
IT1044619B (it)	1980-04-21
DE2539060B2 (de)	1981-04-16

Publication	Publication Date	Title
US5017542A (en)	1991-05-21	Catalyst for the oxidation and ammonoxidation of α-, β-unsaturated hydrocarbons
US6429332B1 (en)	2002-08-06	Catalyst for production of acrylic acid and method for production of acrylic acid by the use of the catalyst
US4339355A (en)	1982-07-13	Catalytic oxide of molybdenum, vanadium, niobium and optional 4th metal
US4066704A (en)	1978-01-03	Catalytic oxidation
KR100210642B1 (ko)	1999-07-15	메타크릴산 제조용촉매 및 이 촉매를 이용한 메타크릴산의 제조방법
US7009075B2 (en)	2006-03-07	Process for the selective conversion of alkanes to unsaturated carboxylic acids
US4052450A (en)	1977-10-04	Catalytic oxidation of α-olefins
JP3287066B2 (ja)	2002-05-27	アクリル酸の製造方法
US3761516A (en)	1973-09-25	Process for producing unsaturated acids from the corresponding unsaturated aldehydes
EP2117706A1 (fr)	2009-11-18	Catalyseur pour l'oxydation d'aldéhydes saturés et insaturés en acide carboxylique insaturé, procédé de marquage et son procédé d'utilisation
US4560804A (en)	1985-12-24	Catalytic process for the manufacture of ketones
US4034008A (en)	1977-07-05	Process for preparing unsaturated acids and aldehydes
US4415482A (en)	1983-11-15	Oxidation and ammoxidation catalyst
KR100635890B1 (ko)	2006-10-18	메틸벤젠류 산화용 촉매 및 방향족 알데히드의 제조방법
JP4269437B2 (ja)	2009-05-27	メタクリル酸の製造方法
JP2988849B2 (ja)	1999-12-13	アクリル酸製造用触媒およびこの触媒を用いたアクリル酸の製造方法
US4552978A (en)	1985-11-12	Oxidation of unsaturated aldehydes
CA1046491A (fr)	1979-01-16	Catalyseur d'oxydation et procede de preparation d'acides insatures et d'aldehydes
CA1045106A (fr)	1978-12-26	Catalyseur au mo, v et ti, et procede pour la preparation d'acides insatures
JPS6231609B2 (fr)	1987-07-09
GB2029721A (en)	1980-03-26	Catalytic oxidation of methacrolein
US3287394A (en)	1966-11-22	Catalytic synthesis of unsaturated nitriles
JP3855298B2 (ja)	2006-12-06	アルケンおよび／または含酸素化合物の製造方法
US3836586A (en)	1974-09-17	Process for producing acrolein or methacrolein
JP3737028B2 (ja)	2006-01-18	メチルベンゼン類酸化用触媒及び芳香族アルデヒドの製造方法