CH493474A - Verfahren zur Reinigung von Malonsäuredinitril - Google Patents
Verfahren zur Reinigung von MalonsäuredinitrilInfo
- Publication number
- CH493474A CH493474A CH938368A CH938368A CH493474A CH 493474 A CH493474 A CH 493474A CH 938368 A CH938368 A CH 938368A CH 938368 A CH938368 A CH 938368A CH 493474 A CH493474 A CH 493474A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogenation
- malononitrile
- dinitrile
- fumaric
- dependent
- Prior art date
Links
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- 239000001384 succinic acid Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH938368A CH493474A (de) | 1968-06-24 | 1968-06-24 | Verfahren zur Reinigung von Malonsäuredinitril |
| DE19691921662 DE1921662C3 (de) | 1968-05-09 | 1969-04-28 | Verfahren zur Reinigung von Malonsäuredinitril |
| CS308669A CS157061B2 (pl) | 1968-05-09 | 1969-04-30 | |
| RO59900A RO56619A (pl) | 1968-05-09 | 1969-05-06 | |
| ES366851A ES366851A1 (es) | 1968-05-09 | 1969-05-06 | Procedimiento para la preparacion de dinitrilo de acido ma-lonico puro. |
| US822724A US3655721A (en) | 1968-05-09 | 1969-05-07 | Process for the production of malonic acid dinitrile and purification thereof |
| YU1127/69A YU32949B (en) | 1968-05-09 | 1969-05-07 | Postupak za proizvodnju cistog dinitrila malonske kiseline |
| BE732687D BE732687A (pl) | 1968-05-09 | 1969-05-07 | |
| FR6914577A FR2008128A1 (pl) | 1968-05-09 | 1969-05-07 | |
| AT654770A AT296953B (de) | 1968-05-09 | 1969-05-07 | Verfahren zur Herstellung von reinem Malonsäuredinitril |
| SE7115883A SE385473B (sv) | 1968-05-09 | 1969-05-08 | Sett att rena propandinitril genom avlegsnande av den vid framstellningen av propandinitril ur acetonnitril och klorcyan erhallna cis- och transbutendinitrilen ur reaktionsblandningen, vid diels-alder- m.m. |
| NO1898/69A NO130584C (pl) | 1968-05-09 | 1969-05-08 | |
| SE7115884A SE385474B (sv) | 1968-05-09 | 1969-05-08 | Sett att rena propandinitril genom avlegsnande av den vid omsettningen av acetonitril och klorcyan till propandinitril som biprodukt erhallna cis- och transbutendinitrilen genom selektiv hydrering |
| JP44034898A JPS50646B1 (pl) | 1968-05-09 | 1969-05-08 | |
| PL15712369A PL78198B1 (pl) | 1968-06-24 | 1969-05-08 | |
| GB23712/69A GB1222343A (en) | 1968-05-09 | 1969-05-09 | Process for the production of pure malonic acid dinitrile |
| NL6907129.A NL164553C (nl) | 1968-05-09 | 1969-05-09 | Werkwijze voor het opwerken van een malonzuur- dinitrileprodukt. |
| DK369570A DK122955B (da) | 1968-05-09 | 1970-07-16 | Fremgangsmåde til fremstilling af rent malonsyredinitril. |
| US00137593A US3742020A (en) | 1968-05-09 | 1971-04-26 | Process for the production of malonic acid dinitrile and purification thereof |
| US05/137,592 US4105688A (en) | 1968-05-09 | 1971-04-26 | Process for the production of malonic acid dinitrile and purification thereof |
| YU68174A YU35579B (en) | 1968-06-24 | 1974-03-13 | Process for the purification of malonic acid dinitrile |
| NL8004516A NL8004516A (nl) | 1968-05-09 | 1980-08-07 | Werkwijze voor het opwerken van een malonzuurdinitrile- produkt. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH938368A CH493474A (de) | 1968-06-24 | 1968-06-24 | Verfahren zur Reinigung von Malonsäuredinitril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH493474A true CH493474A (de) | 1970-07-15 |
Family
ID=4351416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH938368A CH493474A (de) | 1968-05-09 | 1968-06-24 | Verfahren zur Reinigung von Malonsäuredinitril |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH493474A (pl) |
| PL (1) | PL78198B1 (pl) |
| YU (1) | YU35579B (pl) |
-
1968
- 1968-06-24 CH CH938368A patent/CH493474A/de not_active IP Right Cessation
-
1969
- 1969-05-08 PL PL15712369A patent/PL78198B1/pl unknown
-
1974
- 1974-03-13 YU YU68174A patent/YU35579B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU68174A (en) | 1980-10-31 |
| YU35579B (en) | 1981-04-30 |
| PL78198B1 (pl) | 1975-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |