DE1768959C3 - Verfahren zur gleichzeitigen Herstellung von Acrylnitril und Methacrylnitril - Google Patents
Verfahren zur gleichzeitigen Herstellung von Acrylnitril und MethacrylnitrilInfo
- Publication number
- DE1768959C3 DE1768959C3 DE19681768959 DE1768959A DE1768959C3 DE 1768959 C3 DE1768959 C3 DE 1768959C3 DE 19681768959 DE19681768959 DE 19681768959 DE 1768959 A DE1768959 A DE 1768959A DE 1768959 C3 DE1768959 C3 DE 1768959C3
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- acrylonitrile
- methacrylonitrile
- isobutylene
- ammonia
- 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
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 7
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 title claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 230000003647 oxidation Effects 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
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 description 15
- 150000002825 nitriles Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic nitriles Chemical class 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65436267A | 1967-07-19 | 1967-07-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1768959A1 DE1768959A1 (de) | 1972-01-05 |
| DE1768959B2 DE1768959B2 (de) | 1978-02-23 |
| DE1768959C3 true DE1768959C3 (de) | 1978-10-19 |
Family
ID=24624549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768959 Expired DE1768959C3 (de) | 1967-07-19 | 1968-07-17 | Verfahren zur gleichzeitigen Herstellung von Acrylnitril und Methacrylnitril |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA806220A (enrdf_load_stackoverflow) |
| DE (1) | DE1768959C3 (enrdf_load_stackoverflow) |
| FR (1) | FR1576005A (enrdf_load_stackoverflow) |
| GB (2) | GB1238347A (enrdf_load_stackoverflow) |
| IT (1) | IT840404A (enrdf_load_stackoverflow) |
| NL (1) | NL6809591A (enrdf_load_stackoverflow) |
-
0
- IT IT840404D patent/IT840404A/it unknown
- GB GBC33777D patent/GB190333777A/en active Active
- CA CA806220A patent/CA806220A/en not_active Expired
-
1968
- 1968-07-05 NL NL6809591A patent/NL6809591A/xx unknown
- 1968-07-11 FR FR1576005D patent/FR1576005A/fr not_active Expired
- 1968-07-16 GB GB1238347D patent/GB1238347A/en not_active Expired
- 1968-07-17 DE DE19681768959 patent/DE1768959C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1238347A (enrdf_load_stackoverflow) | 1971-07-07 |
| FR1576005A (enrdf_load_stackoverflow) | 1969-07-25 |
| IT840404A (enrdf_load_stackoverflow) | |
| DE1768959B2 (de) | 1978-02-23 |
| DE1768959A1 (de) | 1972-01-05 |
| NL6809591A (enrdf_load_stackoverflow) | 1969-01-21 |
| CA806220A (en) | 1969-02-11 |
| GB190333777A (enrdf_load_stackoverflow) |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |