CA1037054A - Catalyst with mo, v, ta and process for preparing unsaturated acids - Google Patents
Catalyst with mo, v, ta and process for preparing unsaturated acidsInfo
- Publication number
- CA1037054A CA1037054A CA210,975A CA210975A CA1037054A CA 1037054 A CA1037054 A CA 1037054A CA 210975 A CA210975 A CA 210975A CA 1037054 A CA1037054 A CA 1037054A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- unsaturated aliphatic
- alumina
- elements
- grams
- Prior art date
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 81
- 239000002253 acid Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 5
- 150000007513 acids Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 20
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 20
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 19
- 230000003647 oxidation Effects 0.000 claims abstract description 17
- -1 unsaturated aliphatic aldehydes Chemical class 0.000 claims abstract description 14
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 8
- 239000012808 vapor phase Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 31
- 238000001035 drying Methods 0.000 claims description 24
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical group C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 20
- 229910052715 tantalum Inorganic materials 0.000 claims description 19
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 17
- 150000001299 aldehydes Chemical class 0.000 claims description 14
- 230000003197 catalytic effect Effects 0.000 claims description 14
- 239000002002 slurry Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 5
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 125000004429 atom Chemical group 0.000 description 34
- 239000000243 solution Substances 0.000 description 30
- 229910001220 stainless steel Inorganic materials 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- 238000001704 evaporation Methods 0.000 description 23
- 239000000463 material Substances 0.000 description 23
- 239000010935 stainless steel Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 10
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- OSYUGTCJVMTNTO-UHFFFAOYSA-D oxalate;tantalum(5+) Chemical compound [Ta+5].[Ta+5].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O OSYUGTCJVMTNTO-UHFFFAOYSA-D 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 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 5
- 239000011733 molybdenum Substances 0.000 description 5
- 229910052758 niobium Inorganic materials 0.000 description 5
- 239000010955 niobium Substances 0.000 description 5
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 5
- 150000003891 oxalate salts Chemical class 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Inorganic materials [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000004251 Ammonium lactate Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229940059265 ammonium lactate Drugs 0.000 description 2
- 235000019286 ammonium lactate Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003892 tartrate salts Chemical class 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229940037003 alum Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- GDFLGQIOWFLLOC-UHFFFAOYSA-N azane;2-hydroxypropanoic acid;titanium Chemical compound [NH4+].[Ti].CC(O)C([O-])=O GDFLGQIOWFLLOC-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- MKNZTJIHKCVUHC-UHFFFAOYSA-N iron(3+);triazide Chemical compound [N-]=[N+]=N[Fe](N=[N+]=[N-])N=[N+]=[N-] MKNZTJIHKCVUHC-UHFFFAOYSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ALTWGIIQPLQAAM-UHFFFAOYSA-N metavanadate Chemical compound [O-][V](=O)=O ALTWGIIQPLQAAM-UHFFFAOYSA-N 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 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
- 150000002822 niobium compounds Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 150000003482 tantalum compounds Chemical class 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 229910001935 vanadium 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40841773A | 1973-10-23 | 1973-10-23 | |
| US05/505,783 US4410725A (en) | 1973-10-23 | 1974-09-13 | Process for preparing unsaturated acids with Mo, V, Ta-containing catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037054A true CA1037054A (en) | 1978-08-22 |
Family
ID=27020269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA210,975A Expired CA1037054A (en) | 1973-10-23 | 1974-10-08 | Catalyst with mo, v, ta and process for preparing unsaturated acids |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4410725A (https=) |
| JP (1) | JPS5755457B2 (https=) |
| CA (1) | CA1037054A (https=) |
| DE (1) | DE2449993C3 (https=) |
| FR (1) | FR2248260B1 (https=) |
| GB (1) | GB1488024A (https=) |
| IT (1) | IT1025097B (https=) |
| NL (1) | NL7413818A (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56113726A (en) * | 1980-02-08 | 1981-09-07 | Standard Oil Co | Manufacture of aldehyde and carboxylic acid |
| DE3628664A1 (de) * | 1986-08-23 | 1988-03-03 | Degussa | Verfahren zur herstellung von 1,12-dodecandisaeure ii |
| DE3628662A1 (de) * | 1986-08-23 | 1988-03-03 | Degussa | Verfahren zur herstellung von 1,12-dodecandisaeure i |
| DE4132263A1 (de) * | 1991-09-27 | 1993-04-01 | Basf Ag | Verfahren zur katalytischen gasphasenoxidation von acrolein zu acrylsaeure |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532734A (en) * | 1966-03-25 | 1970-10-06 | Eastman Kodak Co | Manufacture of acrylonitrile |
| US3445521A (en) * | 1966-11-17 | 1969-05-20 | Standard Oil Co | Promoted antimony-iron oxidation catalyst |
| US3557199A (en) * | 1967-02-21 | 1971-01-19 | Grace W R & Co | Oxidation of acrolein and methacrolein |
| US3525101A (en) * | 1967-12-06 | 1970-08-18 | Eastman Kodak Co | Method for the preparation of nitriles |
| FR2016707A1 (https=) * | 1968-08-31 | 1970-05-08 | Degussa | |
| US3545624A (en) * | 1968-10-09 | 1970-12-08 | George Krikorian | Wire shelving and basket having snap-in surface forming members |
| BE758269A (fr) * | 1969-10-31 | 1971-04-30 | Montedison Spa | Procede de preparation d'acide acetique par oxydation catalytique d'olefines en phase gazeuse |
| US3546139A (en) * | 1969-11-03 | 1970-12-08 | Eastman Kodak Co | Molybdenum,niobium,tantalum,arsenic in catalysts for vapor phase production of alpha,beta-unsaturated acids |
| US3853792A (en) * | 1971-04-27 | 1974-12-10 | Nippon Catalytic Chem Ind | Catalytic metal oxide |
| US4014927A (en) * | 1972-09-07 | 1977-03-29 | Mitsubishi Petrochemical Company Limited | Process for production of unsaturated acids from corresponding unsaturated aldehydes |
-
1974
- 1974-09-13 US US05/505,783 patent/US4410725A/en not_active Expired - Lifetime
- 1974-10-08 CA CA210,975A patent/CA1037054A/en not_active Expired
- 1974-10-22 JP JP49121090A patent/JPS5755457B2/ja not_active Expired
- 1974-10-22 DE DE2449993A patent/DE2449993C3/de not_active Expired
- 1974-10-22 FR FR7435427A patent/FR2248260B1/fr not_active Expired
- 1974-10-22 IT IT28667/74A patent/IT1025097B/it active
- 1974-10-22 NL NL7413818A patent/NL7413818A/xx active Search and Examination
- 1974-10-22 GB GB45553/74A patent/GB1488024A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4410725A (en) | 1983-10-18 |
| JPS5755457B2 (https=) | 1982-11-24 |
| JPS5078584A (https=) | 1975-06-26 |
| NL7413818A (nl) | 1975-04-25 |
| IT1025097B (it) | 1978-08-10 |
| DE2449993B2 (de) | 1977-08-04 |
| DE2449993A1 (de) | 1975-04-24 |
| FR2248260A1 (https=) | 1975-05-16 |
| DE2449993C3 (de) | 1978-04-06 |
| FR2248260B1 (https=) | 1978-04-28 |
| GB1488024A (en) | 1977-10-05 |
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