DE2139565C3 - Verfahren zur Herstellung von Acrylnitril bzw. Methacrylnitril aus Propylen bzw. Isobutylen - Google Patents
Verfahren zur Herstellung von Acrylnitril bzw. Methacrylnitril aus Propylen bzw. IsobutylenInfo
- Publication number
- DE2139565C3 DE2139565C3 DE2139565A DE2139565A DE2139565C3 DE 2139565 C3 DE2139565 C3 DE 2139565C3 DE 2139565 A DE2139565 A DE 2139565A DE 2139565 A DE2139565 A DE 2139565A DE 2139565 C3 DE2139565 C3 DE 2139565C3
- Authority
- DE
- Germany
- Prior art keywords
- oxygen
- catalyst
- compositions
- tellurium
- catalysts
- 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims description 16
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims description 16
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 title claims 2
- 239000003054 catalyst Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052721 tungsten Inorganic materials 0.000 claims description 9
- 239000010937 tungsten Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 2
- 229910052714 tellurium Inorganic materials 0.000 claims 7
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims 7
- 238000001354 calcination Methods 0.000 claims 2
- 239000005078 molybdenum compound Substances 0.000 claims 2
- 150000002752 molybdenum compounds Chemical class 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 241001026509 Kata Species 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000000975 co-precipitation Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000001125 extrusion Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 150000002505 iron Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000001694 spray drying Methods 0.000 claims 1
- 210000002105 tongue Anatomy 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 238000000844 transformation Methods 0.000 claims 1
- 150000003657 tungsten Chemical class 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 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
- B01J23/84—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
- B01J23/888—Tungsten
-
- 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
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/30—Tungsten
-
- 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
-
- 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
-
- 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)
- Catalysts (AREA)
- Sheets, Magazines, And Separation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2840470 | 1970-08-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2139565A1 DE2139565A1 (de) | 1972-02-10 |
| DE2139565B2 DE2139565B2 (https=) | 1974-11-28 |
| DE2139565C3 true DE2139565C3 (de) | 1975-07-17 |
Family
ID=11223535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2139565A Expired DE2139565C3 (de) | 1970-08-07 | 1971-08-06 | Verfahren zur Herstellung von Acrylnitril bzw. Methacrylnitril aus Propylen bzw. Isobutylen |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT322529B (https=) |
| BE (1) | BE770965A (https=) |
| CA (1) | CA970348A (https=) |
| CH (1) | CH550775A (https=) |
| DE (1) | DE2139565C3 (https=) |
| ES (1) | ES394600A1 (https=) |
| FR (1) | FR2101990A5 (https=) |
| GB (1) | GB1367134A (https=) |
| LU (1) | LU63674A1 (https=) |
| NL (1) | NL7110914A (https=) |
| NO (1) | NO132319C (https=) |
| SE (1) | SE401824B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5057946A (https=) * | 1973-07-17 | 1975-05-20 |
-
1971
- 1971-07-26 CA CA119,137A patent/CA970348A/en not_active Expired
- 1971-08-04 GB GB3669771A patent/GB1367134A/en not_active Expired
- 1971-08-04 FR FR7128626A patent/FR2101990A5/fr not_active Expired
- 1971-08-05 NO NO2943/71A patent/NO132319C/no unknown
- 1971-08-05 BE BE770965A patent/BE770965A/xx unknown
- 1971-08-06 NL NL7110914A patent/NL7110914A/xx not_active Application Discontinuation
- 1971-08-06 LU LU63674D patent/LU63674A1/xx unknown
- 1971-08-06 AT AT691971A patent/AT322529B/de not_active IP Right Cessation
- 1971-08-06 CH CH1161071A patent/CH550775A/fr not_active IP Right Cessation
- 1971-08-06 ES ES394600A patent/ES394600A1/es not_active Expired
- 1971-08-06 SE SE7110104A patent/SE401824B/xx unknown
- 1971-08-06 DE DE2139565A patent/DE2139565C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES394600A1 (es) | 1974-09-16 |
| CA970348A (en) | 1975-07-01 |
| DE2139565B2 (https=) | 1974-11-28 |
| NO132319C (https=) | 1975-10-22 |
| FR2101990A5 (https=) | 1972-03-31 |
| SE401824B (sv) | 1978-05-29 |
| GB1367134A (en) | 1974-09-18 |
| AT322529B (de) | 1975-05-26 |
| LU63674A1 (https=) | 1971-12-14 |
| NO132319B (https=) | 1975-07-14 |
| BE770965A (fr) | 1971-12-16 |
| NL7110914A (https=) | 1972-02-09 |
| DE2139565A1 (de) | 1972-02-10 |
| CH550775A (fr) | 1974-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3300044C2 (de) | Katalysator für die Oxidation von Propylen | |
| DE69012450T2 (de) | Verfahren zur Herstellung von Eisen-Phosphor und Antimon enthaltenden Metalloxid-Oxidationskatalysatoren. | |
| DE69216390T2 (de) | Katalysator und Verfahren zur Oxidation oder Ammoxidation von Olefinen | |
| DE69001365T2 (de) | Verfahren zur herstellung von molybdaenhaltigem metalloxid-fliessbettkatalysator. | |
| DE2038749C3 (https=) | ||
| DE2943707A1 (de) | Oxidationskatalysator, seine herstellung und verwendung (ii) | |
| DE69105890T2 (de) | Eisen-Antimon enthaltender Katalysator sowie Verfahren zur Herstellung desselben. | |
| DE2203709B2 (de) | Oxydationskatalysator und seine Verwendung zur Herstellung von Acrylnitril und Methacrylnitril | |
| DE69101865T2 (de) | Katalysator, Verfahren zu seiner Herstellung und seine Verwendung. | |
| DE2635031C2 (de) | Katalysator zur Herstellung einer α,β-ungesättigten aliphatischen Carbonsäure und Verwendung dieses Katalysators | |
| DE2147480C2 (de) | Verfahren zur Herstellung von Acrylnitril und Methacrylnitril | |
| DE2704991B2 (de) | Verfahren zur Herstellung von Methacrylsäure | |
| DE2529537C3 (de) | Verfahren zur Herstellung von Metharcrylsäure durch katalytische Gasphasenoxidation von Methacrolein | |
| DE68907642T2 (de) | Verfahren zur herstellung von cyanwasserstoff durch katalytische ammoxidierung in der gasphase von methanol. | |
| DE2523757B2 (de) | Verfahren zur Herstellung von Methacrylsäure durch katalytische Oxidation von Methacrolein mit Sauerstoff | |
| DE69112262T2 (de) | Verfahren zur Herstellung von Katalysatoren für die Herstellung von Methacrylsäure. | |
| DE3886103T2 (de) | Verfahren zur Ammoxidation von Paraffinen und Katalysatorzusammensetzung dafür. | |
| DE69502949T2 (de) | Zusammensetzungen des schalenkatalysator-typus, enthaltend wismut, nickel, kobalt, eisen und molybdän, und deren verwendung zur herstellung von ungesättigten aldehyden | |
| DE2344956A1 (de) | Verfahren zur herstellung ungesaettigter saeuren aus entsprechenden ungesaettigten aldehyden | |
| DE2139565C3 (de) | Verfahren zur Herstellung von Acrylnitril bzw. Methacrylnitril aus Propylen bzw. Isobutylen | |
| DE1493290A1 (de) | Verfahren zur Herstellung von ungesaettigten Nitrilen | |
| DE2000425C3 (https=) | ||
| DE2321150A1 (de) | Verfahren zur herstellung von methacrylnitril | |
| DE2429095A1 (de) | Verfahren zur herstellung von methacrylsaeure | |
| DE2039497C3 (de) | Verfahren zur Herstellung von Antimon enthaltenden Katalysatoren und Verwendung der Katalysatoren für die Herstellung von aromatischen und heteroaromatischen Nitrilen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |