IL25695A - Polymeric impurity removal from an aqueous quaternary ammonium salt solution used in electrohydrodimerization of acrylonitrile - Google Patents
Polymeric impurity removal from an aqueous quaternary ammonium salt solution used in electrohydrodimerization of acrylonitrileInfo
- Publication number
- IL25695A IL25695A IL25695A IL2569566A IL25695A IL 25695 A IL25695 A IL 25695A IL 25695 A IL25695 A IL 25695A IL 2569566 A IL2569566 A IL 2569566A IL 25695 A IL25695 A IL 25695A
- Authority
- IL
- Israel
- Prior art keywords
- quaternary ammonium
- ammonium salt
- solution
- salt
- acrylonitrile
- Prior art date
Links
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims description 26
- 239000012266 salt solution Substances 0.000 title claims description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title description 20
- 239000012535 impurity Substances 0.000 title description 11
- 150000003839 salts Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 17
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 230000003165 hydrotropic effect Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- HCWMUANODLPMEO-UHFFFAOYSA-M ethyl sulfate;tetraethylazanium Chemical group CCOS([O-])(=O)=O.CC[N+](CC)(CC)CC HCWMUANODLPMEO-UHFFFAOYSA-M 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 3
- -1 tetraalkylammonium alkyl sulfate Chemical class 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 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 4
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 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 hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 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
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LNLFLMCWDHZINJ-UHFFFAOYSA-N hexane-1,3,6-tricarbonitrile Chemical compound N#CCCCC(C#N)CCC#N LNLFLMCWDHZINJ-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/29—Coupling reactions
- C25B3/295—Coupling reactions hydrodimerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US454740A US3335162A (en) | 1965-05-10 | 1965-05-10 | Polymeric impurity removal from an aqueous quaternary ammonium salt solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL25695A true IL25695A (en) | 1970-02-19 |
Family
ID=23805877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25695A IL25695A (en) | 1965-05-10 | 1966-05-03 | Polymeric impurity removal from an aqueous quaternary ammonium salt solution used in electrohydrodimerization of acrylonitrile |
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 |
| GB1311354A (en) * | 1969-05-08 | 1973-03-28 | Asahi Chemical Ind | Electrolytic hydrodimerization of acrylonitrile |
| 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 LU LU51019A patent/LU51019A1/xx unknown
- 1966-05-03 GB GB19571/66A patent/GB1153194A/en not_active Expired
- 1966-05-03 IL IL25695A patent/IL25695A/en unknown
- 1966-05-05 BE BE680551D patent/BE680551A/xx unknown
- 1966-05-09 NL NL6606313A patent/NL6606313A/xx unknown
- 1966-05-09 AT AT435566A patent/AT265234B/de active
- 1966-05-09 DK DK236266AA patent/DK117696B/da unknown
- 1966-05-10 DE DE19661593014 patent/DE1593014A1/de active Granted
- 1966-05-10 JP JP41029162A patent/JPS496296B1/ja active Pending
- 1966-05-10 CH CH674366A patent/CH469654A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6606313A (enrdf_load_stackoverflow) | 1966-11-11 |
| AT265234B (de) | 1968-10-10 |
| JPS496296B1 (enrdf_load_stackoverflow) | 1974-02-13 |
| CH469654A (de) | 1969-03-15 |
| GB1153194A (en) | 1969-05-29 |
| BE680551A (enrdf_load_stackoverflow) | 1966-11-07 |
| DE1593014A1 (de) | 1970-04-16 |
| US3335162A (en) | 1967-08-08 |
| LU51019A1 (enrdf_load_stackoverflow) | 1966-11-03 |
| DK117696B (da) | 1970-05-25 |
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