DE1618497A1 - Verfahren zur Herstellung von aromatischen Polynitrilen - Google Patents
Verfahren zur Herstellung von aromatischen PolynitrilenInfo
- Publication number
- DE1618497A1 DE1618497A1 DE19671618497 DE1618497A DE1618497A1 DE 1618497 A1 DE1618497 A1 DE 1618497A1 DE 19671618497 DE19671618497 DE 19671618497 DE 1618497 A DE1618497 A DE 1618497A DE 1618497 A1 DE1618497 A1 DE 1618497A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- aromatic
- xylene
- hydrocarbons
- ammoxidation
- 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
- 238000000034 method Methods 0.000 title claims description 24
- 125000003118 aryl group Chemical group 0.000 title claims description 14
- 229920005554 polynitrile Polymers 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 28
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 17
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 3
- 239000011949 solid catalyst Substances 0.000 claims description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241001292396 Cirrhitidae Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 238000013021 overheating Methods 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 compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 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
- C07C253/28—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing six-membered aromatic rings, e.g. styrene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53323766A | 1966-03-10 | 1966-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618497A1 true DE1618497A1 (de) | 1971-01-14 |
Family
ID=24125089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618497 Pending DE1618497A1 (de) | 1966-03-10 | 1967-03-10 | Verfahren zur Herstellung von aromatischen Polynitrilen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3497545A (enrdf_load_stackoverflow) |
| BE (1) | BE694694A (enrdf_load_stackoverflow) |
| CH (1) | CH471086A (enrdf_load_stackoverflow) |
| DE (1) | DE1618497A1 (enrdf_load_stackoverflow) |
| ES (1) | ES337833A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1181391A (enrdf_load_stackoverflow) |
| IL (1) | IL27564A (enrdf_load_stackoverflow) |
| LU (1) | LU53090A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6701607A (enrdf_load_stackoverflow) |
| NO (1) | NO121660B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927007A (en) * | 1970-08-08 | 1975-12-16 | God Und Silber Scheideanstalt | Catalysts for the production of aromatic and heteroaromatic nitriles |
| BE844340A (fr) * | 1976-07-20 | 1977-01-20 | Procede de preparation de benzonitrile, et produit ainsi obtenu | |
| NL178870C (nl) * | 1979-03-06 | 1986-06-02 | Inst Neftekhim Protsessov | Werkwijze voor de bereiding van ftalonitrillen, alsmede de daarbij te gebruiken katalysator. |
| JPS56139444A (en) * | 1980-04-01 | 1981-10-30 | Takeda Chem Ind Ltd | Production of aromatic nitrile |
| CH686133A5 (de) * | 1993-02-23 | 1996-01-15 | Basf Ag | Verfahren zur Herstellung von Dicyanobenzolen mittels Ammonoxidation. |
| US20030126073A1 (en) * | 2001-03-20 | 2003-07-03 | David Lawrence | Charitable transaction risk management clearinghouse |
| US7161021B2 (en) * | 2001-12-13 | 2007-01-09 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a polynitrile compound |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA619842A (en) * | 1961-05-09 | F. Hardy George | Production of phthalonitriles | |
| CA512864A (en) * | 1955-05-17 | K. Dixon James | Preparation of nitriles | |
| GB645754A (en) * | 1943-11-10 | 1950-11-08 | Socony Vacuum Oil Co Inc | Production of nitriles |
| US2496661A (en) * | 1947-11-28 | 1950-02-07 | Socony Vacuum Oil Co Inc | Production of nitriles |
| US2838558A (en) * | 1955-09-27 | 1958-06-10 | Distillers Co Yeast Ltd | Catalytic production of aromatic nitriles and imides |
| US2833807A (en) * | 1956-06-26 | 1958-05-06 | Allied Chem & Dye Corp | Production of phthalonitriles |
| DE1141274B (de) * | 1960-08-20 | 1962-12-20 | Bayer Ag | Verfahren zur Herstellung von aromatischen Nitrilen |
| US3231600A (en) * | 1962-02-02 | 1966-01-25 | Socony Mobil Oil Co Inc | Synthesis of aromatic nitriles |
-
1966
- 1966-03-10 US US533237A patent/US3497545A/en not_active Expired - Lifetime
-
1967
- 1967-02-02 NL NL6701607A patent/NL6701607A/xx unknown
- 1967-02-27 BE BE694694D patent/BE694694A/xx unknown
- 1967-03-01 LU LU53090D patent/LU53090A1/xx unknown
- 1967-03-06 GB GB00500/67A patent/GB1181391A/en not_active Expired
- 1967-03-09 IL IL27564A patent/IL27564A/xx unknown
- 1967-03-09 CH CH345667A patent/CH471086A/fr not_active IP Right Cessation
- 1967-03-09 NO NO167204A patent/NO121660B/no unknown
- 1967-03-10 ES ES337833A patent/ES337833A1/es not_active Expired
- 1967-03-10 DE DE19671618497 patent/DE1618497A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL27564A (en) | 1970-09-17 |
| GB1181391A (en) | 1970-02-18 |
| NL6701607A (enrdf_load_stackoverflow) | 1967-09-11 |
| BE694694A (enrdf_load_stackoverflow) | 1967-08-28 |
| LU53090A1 (enrdf_load_stackoverflow) | 1968-12-09 |
| NO121660B (enrdf_load_stackoverflow) | 1971-03-29 |
| CH471086A (fr) | 1969-04-15 |
| ES337833A1 (es) | 1968-03-01 |
| US3497545A (en) | 1970-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1180739B (de) | Verfahren zur Herstellung von Acrylsaeurenitril durch Umsetzen von Propylen mit Ammoniak und Sauerstoff | |
| DE1518502C3 (de) | Verfahren zur Herstellung von alpha,beta olefinisch ungesättigten aliphatischen Mononitnlen | |
| DE1618497A1 (de) | Verfahren zur Herstellung von aromatischen Polynitrilen | |
| DE2812151A1 (de) | Verfahren zur herstellung von organischen nitrilen | |
| DE1930880B2 (de) | Verfahren zur Herstellung von Iso- und/oder Terephthalsäuredinitrilen | |
| DE1205962B (de) | Verfahren zur Herstellung von Acrylsaeurenitril unter gleichzeitiger Gewinnung von Blausaeure aus dem bei der Umsetzung als Nebenprodukt entstandenen Acetonitril | |
| DE2703070A1 (de) | Verfahren zur herstellung von 3-methylpyridin | |
| DE2500650A1 (de) | Katalytisches verfahren zur herstellung ungesaettigter nitrile | |
| DE1961722C3 (de) | Verfahren zur Herstellung von Dimethylstyrolen | |
| DE2323867B2 (de) | Verfahren zur Herstellung von olefinisch ungesättigten Aktehydcyanhydrlnen | |
| DE1005954B (de) | Verfahren zur Herstellung von Polyencarbonsaeureestern bzw. -nitrilen | |
| DE2102263A1 (de) | Verfahren zur kontinuierlichen Herstellung ungesättigter Nitrile | |
| DE1286002B (de) | Verfahren zur Herstellung von aromatischen Nitrilen | |
| DE1805355A1 (de) | Verfahren zur Herstellung von Ketonen aus Olefinen | |
| DE2933314C2 (de) | Verfahren zur Herstellung von Nitrosobenzol | |
| DE1468429C (de) | Verfahren zur Herstellung von Acryl bzw Methacrvlsaure | |
| DE1493465A1 (de) | Verfahren zur Herstellung von Propylendiamin und Dipropylentriamin | |
| DE2264529A1 (de) | Verfahren zur synthese von diolefinen | |
| DE2545698A1 (de) | Verfahren zur herstellung von butendioldiacetaten | |
| DE2256039C3 (de) | Herstellung von 1,4-Dicyanbutenen | |
| DE2026043A1 (enrdf_load_stackoverflow) | ||
| DE1049853B (de) | Verfahren zur Herstellung von Alkylidenalkenylaminen | |
| DE1793446A1 (de) | Verfahren zur Herstellung von Dichloracetylchlorid | |
| DE1545750A1 (de) | Verfahren zur Herstellung von Pyridin | |
| DE2355182C3 (de) | Verfahren zur Herstellung von Stickstoffderivaten aromatischer Carbonsäuren |