DE1296622B - Verfahren zur Herstellung von Acrylsaeurenitril oder Methacrylsaeurenitril durch Umsetzung von Propylen oder Isobutylen mit Sauerstoff und Ammoniak - Google Patents
Verfahren zur Herstellung von Acrylsaeurenitril oder Methacrylsaeurenitril durch Umsetzung von Propylen oder Isobutylen mit Sauerstoff und AmmoniakInfo
- Publication number
- DE1296622B DE1296622B DET23107A DET0023107A DE1296622B DE 1296622 B DE1296622 B DE 1296622B DE T23107 A DET23107 A DE T23107A DE T0023107 A DET0023107 A DE T0023107A DE 1296622 B DE1296622 B DE 1296622B
- Authority
- DE
- Germany
- Prior art keywords
- ammonia
- acid nitrile
- vanadium
- propylene
- isobutylene
- 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.)
- Pending
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims description 24
- 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 20
- 238000000034 method Methods 0.000 title claims description 15
- 229910021529 ammonia Inorganic materials 0.000 title claims description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 acrylic acid nitrile Chemical class 0.000 title description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title description 6
- 239000001301 oxygen Substances 0.000 title description 6
- 229910052760 oxygen Inorganic materials 0.000 title description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052797 bismuth Inorganic materials 0.000 claims description 7
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 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
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000008262 pumice Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 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 6
- 239000000243 solution Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910015902 Bi 2 O 3 Inorganic materials 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 229910052810 boron oxide Inorganic materials 0.000 description 3
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 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
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 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
- 150000002739 metals Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910002554 Fe(NO3)3·9H2O Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- QUEDYRXQWSDKKG-UHFFFAOYSA-M [O-2].[O-2].[V+5].[OH-] Chemical compound [O-2].[O-2].[V+5].[OH-] QUEDYRXQWSDKKG-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 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
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(III) oxide Inorganic materials O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QTJRBZRWKMPYDC-UHFFFAOYSA-N boron;oxomolybdenum Chemical compound [B].[Mo]=O QTJRBZRWKMPYDC-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- CJJMLLCUQDSZIZ-UHFFFAOYSA-N oxobismuth Chemical class [Bi]=O CJJMLLCUQDSZIZ-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material 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
- 230000009466 transformation Effects 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
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
-
- 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
- B01J23/847—Vanadium, niobium or tantalum or polonium
- B01J23/8472—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4263861 | 1961-11-30 | ||
| JP4263761 | 1961-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1296622B true DE1296622B (de) | 1969-06-04 |
Family
ID=26382356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET23107A Pending DE1296622B (de) | 1961-11-30 | 1962-11-30 | Verfahren zur Herstellung von Acrylsaeurenitril oder Methacrylsaeurenitril durch Umsetzung von Propylen oder Isobutylen mit Sauerstoff und Ammoniak |
Country Status (4)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL121947C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-04-01 | |||
| IL22742A (en) * | 1964-01-10 | 1968-09-26 | Princeton Chemical Res Inc | Production of nitriles |
| US3386923A (en) * | 1964-06-15 | 1968-06-04 | Eastman Kodak Co | Catalyst and process for the preparation of unsaturated nitriles |
| US3383329A (en) * | 1964-06-15 | 1968-05-14 | Eastman Kodak Co | Preparation of unsaturated nitriles by a catalytic process |
| CA794856A (en) * | 1965-10-29 | 1968-09-17 | Th. A. Huibers Derk | Preparation of nitriles |
| DE1276620B (de) * | 1965-11-26 | 1968-09-05 | Huels Chemische Werke Ag | Verfahren zur Herstellung von gesaettigten aliphatischen Alkoholen |
| IT859097A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-11-28 | |||
| US4000176A (en) * | 1970-05-18 | 1976-12-28 | Nitto Chemical Industry Co., Ltd. | Process for simultaneously producing methacrylo-nitrile and butadiene by vapor-phase catalytic oxidation of mixed butenes |
| JPS5117537B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-03-12 | 1976-06-03 | ||
| GB1426254A (en) * | 1972-10-06 | 1976-02-25 | Sumitomo Chemical Co | Process for preparing hydrogen cyanide |
| JPS52136122A (en) * | 1976-05-11 | 1977-11-14 | Ube Ind Ltd | Preparation of acrylonitrile |
| US4528277A (en) * | 1979-04-04 | 1985-07-09 | Union Oil Company Of California | Catalyst for oxidizing hydrogen sulfide |
| US4444908A (en) * | 1979-04-04 | 1984-04-24 | Union Oil Company Of California | Catalyst and process for oxidizing hydrogen sulfide |
| US4444742A (en) * | 1979-04-04 | 1984-04-24 | Union Oil Company Of California | Catalyst and process for oxidizing hydrogen sulfide |
| US4576814A (en) * | 1979-04-04 | 1986-03-18 | Union Oil Company Of California | Catalyst and process for oxidizing hydrogen sulfide |
| US4444741A (en) * | 1979-04-04 | 1984-04-24 | Union Oil Company Of California | Catalyst and process for oxidizing hydrogen sulfide |
| US4473506A (en) * | 1982-10-18 | 1984-09-25 | The Standard Oil Company | Iron selenium tellurium oxide catalysts |
Citations (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE603031A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-04-26 | |||
| BE603033A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-04-26 | |||
| DE897560C (de) * | 1950-12-30 | 1953-11-23 | Distillers Company | Verfahren zur Herstellung von ungesaettigten Nitrilen |
| FR1098400A (fr) * | 1953-04-13 | 1955-07-25 | Bataafsche Petroleum | Procédé de préparation des nitriles non saturés |
| DE941428C (de) * | 1952-10-09 | 1956-04-12 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von ª,ª-ungesaettigten Carbonsaeurenitrilen |
| US2904580A (en) * | 1959-02-24 | 1959-09-15 | Standard Oil Co | Process for the manufacture of acrylonitrile |
| DE1070170B (de) * | 1959-12-03 | The Distillers Company Limited, Edinburgh (Großbritannien) | Verfahren zur Herstellung von ungesättigten Nitrilen | |
| FR1248313A (fr) * | 1959-02-14 | 1960-12-09 | Distillers Co Yeast Ltd | Procédé de production d'acrylonitrile ou de méthacrylonitrile |
| FR1255121A (fr) * | 1959-02-16 | 1961-03-03 | Asahi Chemical Ind | Procédé de production de nitriles non saturés |
| BE598511A (fr) * | 1960-01-02 | 1961-04-14 | Knapsack Ag | Procede de preparation des nitriles non satures notamment l'acrylonitrile |
| FR1261568A (fr) * | 1962-12-08 | 1961-05-19 | Distillers Co Yeast Ltd | Procédé de production d'acrylonitrile ou de méthacrylonitrile |
| FR1268383A (fr) * | 1960-03-09 | 1961-07-28 | Asahi Chemical Ind | Procédé de préparation de nitriles aliphatiques non saturés |
| FR1268324A (fr) * | 1960-09-27 | 1961-07-28 | Union Chimique Belge Sa | Catalyseurs d'oxydation |
| FR1269382A (fr) * | 1959-07-18 | 1961-08-11 | Bayer Ag | Procédé de préparation d'acrylonitrile et de méthacrylonitrile |
| FR1272358A (fr) * | 1960-10-28 | 1961-09-22 | Shell Int Research | Perfectionnements aux procédés d'oxydation des hydrocarbures |
| FR1272309A (fr) * | 1960-10-27 | 1961-09-22 | Eickhoff Geb | Couteau ou pic haveur, en particulier pour haveuses à chaîne |
| FR1280525A (fr) * | 1960-02-26 | 1961-12-29 | Asahi Chemical Ind | Procédé de préparation de l'acrylonitrile |
| BE607031A (nl) * | 1960-08-10 | 1962-02-08 | Shell Int Research | Werkwijze voor de bereiding van acrylonitril of methacrylonitril |
| FR1292673A (fr) * | 1960-06-21 | 1962-05-04 | Asahi Chemical Ind | Procédé de préparation d'acrylonitrile |
| FR1301077A (fr) * | 1961-08-08 | 1962-08-10 | Shell Int Research | Procédé de préparation des nitriles non saturés |
| FR1310841A (fr) * | 1960-12-07 | 1962-11-30 | Knapsack Ag | Procédé de préparation de nitriles non saturés |
| FR1311683A (fr) * | 1961-01-23 | 1962-12-07 | Eastman Kodak Co | Procédé de préparation de nitriles aliphatiques non saturés et nouveau catalyseur pour ce procédé |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2481826A (en) * | 1947-02-28 | 1949-09-13 | Allied Chem & Dye Corp | Process for making aliphatic nitriles |
| US2830026A (en) * | 1954-01-29 | 1958-04-08 | Shapiro Isadore | Process for producing boron-metal oxide catalyst |
| US2805244A (en) * | 1954-11-29 | 1957-09-03 | Escambia Chem Corp | Production of acrylonitrile |
| US2820812A (en) * | 1955-06-10 | 1958-01-21 | Derives De L Acetylene Soc Ind | Manufacture of acrylic nitrile |
| US2809987A (en) * | 1956-03-30 | 1957-10-15 | Pure Oil Co | Preparation of acrylonitrile and ethylene |
| US2938001A (en) * | 1956-12-13 | 1960-05-24 | Universal Oil Prod Co | Catalyst composite |
| CA619497A (en) * | 1958-04-16 | 1961-05-02 | The Distillers Company Limited | Production of aliphatic nitriles from olefins |
| NL262141A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-03-09 | |||
| CA676881A (en) * | 1961-05-31 | 1963-12-24 | Shell Oil Company | Production of lower aliphatic nitriles |
-
0
- IT IT701822D patent/IT701822A/it unknown
-
1962
- 1962-11-27 GB GB44888/62A patent/GB1025676A/en not_active Expired
- 1962-11-30 DE DET23107A patent/DE1296622B/de active Pending
- 1962-11-30 US US244538A patent/US3232978A/en not_active Expired - Lifetime
Patent Citations (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1070170B (de) * | 1959-12-03 | The Distillers Company Limited, Edinburgh (Großbritannien) | Verfahren zur Herstellung von ungesättigten Nitrilen | |
| DE897560C (de) * | 1950-12-30 | 1953-11-23 | Distillers Company | Verfahren zur Herstellung von ungesaettigten Nitrilen |
| DE941428C (de) * | 1952-10-09 | 1956-04-12 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von ª,ª-ungesaettigten Carbonsaeurenitrilen |
| FR1098400A (fr) * | 1953-04-13 | 1955-07-25 | Bataafsche Petroleum | Procédé de préparation des nitriles non saturés |
| DE1165015B (de) * | 1959-02-14 | 1964-03-12 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von Acrylsaeurenitril oder Methacrylsaeurenitril aus Propylen oder Isobutylen |
| FR1248313A (fr) * | 1959-02-14 | 1960-12-09 | Distillers Co Yeast Ltd | Procédé de production d'acrylonitrile ou de méthacrylonitrile |
| FR1255121A (fr) * | 1959-02-16 | 1961-03-03 | Asahi Chemical Ind | Procédé de production de nitriles non saturés |
| US2904580A (en) * | 1959-02-24 | 1959-09-15 | Standard Oil Co | Process for the manufacture of acrylonitrile |
| DE1127351B (de) * | 1959-02-24 | 1962-04-12 | Standard Oil Co | Verfahren zur Herstellung von ª, ª-ungesaettigten aliphatischen Nitrilen durch Umsetzen von Olefinen mit Ammoniak und Sauerstoff |
| FR1269382A (fr) * | 1959-07-18 | 1961-08-11 | Bayer Ag | Procédé de préparation d'acrylonitrile et de méthacrylonitrile |
| BE598511A (fr) * | 1960-01-02 | 1961-04-14 | Knapsack Ag | Procede de preparation des nitriles non satures notamment l'acrylonitrile |
| FR1278289A (fr) * | 1960-01-02 | 1961-12-08 | Knapsack Ag | Procédé de préparation des nitriles non saturés, notamment de l'acrylonitrile |
| FR1280525A (fr) * | 1960-02-26 | 1961-12-29 | Asahi Chemical Ind | Procédé de préparation de l'acrylonitrile |
| FR1268383A (fr) * | 1960-03-09 | 1961-07-28 | Asahi Chemical Ind | Procédé de préparation de nitriles aliphatiques non saturés |
| BE603033A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-04-26 | |||
| BE603031A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-04-26 | |||
| FR1292673A (fr) * | 1960-06-21 | 1962-05-04 | Asahi Chemical Ind | Procédé de préparation d'acrylonitrile |
| BE607031A (nl) * | 1960-08-10 | 1962-02-08 | Shell Int Research | Werkwijze voor de bereiding van acrylonitril of methacrylonitril |
| FR1268324A (fr) * | 1960-09-27 | 1961-07-28 | Union Chimique Belge Sa | Catalyseurs d'oxydation |
| FR1272309A (fr) * | 1960-10-27 | 1961-09-22 | Eickhoff Geb | Couteau ou pic haveur, en particulier pour haveuses à chaîne |
| FR1272358A (fr) * | 1960-10-28 | 1961-09-22 | Shell Int Research | Perfectionnements aux procédés d'oxydation des hydrocarbures |
| FR1310841A (fr) * | 1960-12-07 | 1962-11-30 | Knapsack Ag | Procédé de préparation de nitriles non saturés |
| FR1311683A (fr) * | 1961-01-23 | 1962-12-07 | Eastman Kodak Co | Procédé de préparation de nitriles aliphatiques non saturés et nouveau catalyseur pour ce procédé |
| FR1301077A (fr) * | 1961-08-08 | 1962-08-10 | Shell Int Research | Procédé de préparation des nitriles non saturés |
| FR1261568A (fr) * | 1962-12-08 | 1961-05-19 | Distillers Co Yeast Ltd | Procédé de production d'acrylonitrile ou de méthacrylonitrile |
Also Published As
| Publication number | Publication date |
|---|---|
| US3232978A (en) | 1966-02-01 |
| IT701822A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| GB1025676A (en) | 1966-04-14 |
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