DE1593014C - - Google Patents
Info
- Publication number
- DE1593014C DE1593014C DE19661593014 DE1593014A DE1593014C DE 1593014 C DE1593014 C DE 1593014C DE 19661593014 DE19661593014 DE 19661593014 DE 1593014 A DE1593014 A DE 1593014A DE 1593014 C DE1593014 C DE 1593014C
- Authority
- DE
- Germany
- Prior art keywords
- solution
- salt
- acrylonitrile
- weight
- percent
- 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
- 239000011780 sodium chloride Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 24
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 19
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 17
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 16
- BTGRAWJCKBQKAO-UHFFFAOYSA-N Adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 230000003165 hydrotropic Effects 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000012266 salt solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000003792 electrolyte Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- HIFXHEXRVMWOAG-UHFFFAOYSA-M phenylmethanesulfonate;tetramethylazanium Chemical compound C[N+](C)(C)C.[O-]S(=O)(=O)CC1=CC=CC=C1 HIFXHEXRVMWOAG-UHFFFAOYSA-M 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- -1 propionic acid nitrile Chemical class 0.000 description 4
- 230000002378 acidificating Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M Tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008360 acrylonitriles Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HCWMUANODLPMEO-UHFFFAOYSA-M ethyl sulfate;tetraethylazanium Chemical compound CCOS([O-])(=O)=O.CC[N+](CC)(CC)CC HCWMUANODLPMEO-UHFFFAOYSA-M 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NTFJXDRAVMOYBG-UHFFFAOYSA-N 2-(2,2-dicyanoethoxymethyl)propanedinitrile Chemical compound N#CC(C#N)COCC(C#N)C#N NTFJXDRAVMOYBG-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N Propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45474065 | 1965-05-10 | ||
| US454740A US3335162A (en) | 1965-05-10 | 1965-05-10 | Polymeric impurity removal from an aqueous quaternary ammonium salt solution |
| DEM0069445 | 1966-05-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1593014A1 DE1593014A1 (de) | 1970-04-16 |
| DE1593014C true DE1593014C (US20030204162A1-20031030-M00001.png) | 1973-06-28 |
Family
ID=23805877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593014 Granted DE1593014A1 (de) | 1965-05-10 | 1966-05-10 | Verfahren zur Entfernung bestimmter organischer Verunreinigungen |
Country Status (11)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3402112A (en) * | 1965-07-26 | 1968-09-17 | Monsanto Co | Process for reducing anode corrosion in an acrylonitrile hydrodimerization cell |
| US3493597A (en) * | 1967-05-25 | 1970-02-03 | Monsanto Co | Purification of aqueous quaternary ammonium salt solutions |
| NL7006700A (US20030204162A1-20031030-M00001.png) * | 1969-05-08 | 1970-11-10 | ||
| US4072713A (en) * | 1972-07-27 | 1978-02-07 | Phillips Petroleum Company | Method for separating tetraalkylammonium salts |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3193481A (en) * | 1962-10-05 | 1965-07-06 | Monsanto Co | Electrolytic hydrodimerization alpha, beta-olefinic nitriles |
-
1965
- 1965-05-10 US US454740A patent/US3335162A/en not_active Expired - Lifetime
-
1966
- 1966-05-03 IL IL25695A patent/IL25695A/en unknown
- 1966-05-03 LU LU51019A patent/LU51019A1/xx unknown
- 1966-05-03 GB GB19571/66A patent/GB1153194A/en not_active Expired
- 1966-05-05 BE BE680551D patent/BE680551A/xx unknown
- 1966-05-09 DK DK236266AA patent/DK117696B/da unknown
- 1966-05-09 AT AT435566A patent/AT265234B/de active
- 1966-05-09 NL NL6606313A patent/NL6606313A/xx unknown
- 1966-05-10 CH CH674366A patent/CH469654A/de unknown
- 1966-05-10 JP JP41029162A patent/JPS496296B1/ja active Pending
- 1966-05-10 DE DE19661593014 patent/DE1593014A1/de active Granted
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE19710510C2 (de) | Verfahren zum Reinigen einer elektrolytischen Kupferlösung | |
| DE19600620C1 (de) | Verfahren zur Darstellung einer besonders reinen Glykolsäure | |
| DE1643469A1 (de) | Elektrolytisches Verfahren zur Herstellung von quarternaeren Ammoniumhydroxyden | |
| DE1593034A1 (de) | Verfahren zur Entfernung von Verunreinigungen aus einem Katholyt | |
| DE1593014C (US20030204162A1-20031030-M00001.png) | ||
| DE1543196A1 (de) | Verfahren zur selektiven Abtrennung von Adipinsaeurenitril und quarternaerem Ammoniumsalz | |
| DE3841590C2 (de) | Verfahren zur Raffination einer Eisenion-haltigen sauren Lösung | |
| EP0381134B1 (de) | Verfahren zur Entsalzung von lösemittelhaltigen Elektrolytlösungen durch Elektrodialyse | |
| DE2404560B2 (de) | Verfahren zur Herstellung von Sebacinsäure | |
| DE2248178A1 (de) | Verfahren zur aufloesung von molybdaen und/oder rhenium | |
| DE1593014B (de) | Verfahren zur Entfernung von teilweise hydrolysiertem Polyacrylnitril | |
| DE60104879T2 (de) | Verfahren zur erhöhung der reinheit von quaternären ammoniumhydroxiden mittels elektrolyse | |
| DE2748279C3 (de) | Verfahren zur Herstellung vonretaer Phosphorsäure aus Naßphosphorsäure | |
| DE1954707C3 (de) | Verfahren zur Wiedergewinnung von Metallkatalysatoren | |
| US3335162A (en) | Polymeric impurity removal from an aqueous quaternary ammonium salt solution | |
| DE2119979A1 (US20030204162A1-20031030-M00001.png) | ||
| AT265235B (de) | Verfahren zur Entfernung von Verunreinigungen aus einem Katholyten für die Elektrohydrodimerisation von Acrylonitril zu Adiponitril | |
| DE3104578A1 (de) | Verfahren zum entfernen von metallen aus metallsalzloesungen | |
| DE1768625A1 (de) | Verfahren zur gewinnung eines quarternaeren ammoniumsalzes aus dem ausfluss einer acrylnitrilelektrohydrodimerisation | |
| DE2022654C3 (de) | Verfahren zur Gewinnung von Adipinsäuredinitril | |
| DE2252036A1 (de) | Verfahren zum elektroraffinieren von rohem kupfer mit hohem antimongehalt | |
| DE2119883C3 (de) | Verfahren zur Reinigung des Elektrolyten bei der elektrolytischen Hydrodimerisierung von Acrylnitril | |
| DE1793568B1 (de) | Verfahren zur Herstellung von paraffinischen Dicarbonsaeure- oder Teracarbonsaeureamiden | |
| AT163426B (de) | Verfahren zur Gewinnung von in sauren Elektrolyten kolloid gelösten bzw. dispers verteilten Eiweißstoffen | |
| AT265213B (de) | Verfahren zum Konzentrieren von Lösungen und Vorrichtung zur Durchführung dieses Verfahrens |
