DE1643604C - - Google Patents
Info
- Publication number
- DE1643604C DE1643604C DE19671643604 DE1643604A DE1643604C DE 1643604 C DE1643604 C DE 1643604C DE 19671643604 DE19671643604 DE 19671643604 DE 1643604 A DE1643604 A DE 1643604A DE 1643604 C DE1643604 C DE 1643604C
- Authority
- DE
- Germany
- Prior art keywords
- acrylonitrile
- water
- oil phase
- catholyte
- phase
- 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 107
- 239000012071 phase Substances 0.000 claims description 90
- BTGRAWJCKBQKAO-UHFFFAOYSA-N Adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- 239000008346 aqueous phase Substances 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 46
- 239000011780 sodium chloride Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
- FVSKHRXBFJPNKK-UHFFFAOYSA-N Propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 28
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 13
- 239000000839 emulsion Substances 0.000 claims description 8
- 239000003792 electrolyte Chemical class 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 48
- 238000009835 boiling Methods 0.000 description 20
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- 238000000926 separation method Methods 0.000 description 14
- 238000005868 electrolysis reaction Methods 0.000 description 12
- 238000000605 extraction Methods 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- -1 sulfates or halides Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000012527 feed solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N Hexamethylenediamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000003115 supporting electrolyte Substances 0.000 description 2
- TXBULBYASDPNNC-UHFFFAOYSA-L tetraethylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC TXBULBYASDPNNC-UHFFFAOYSA-L 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- BCGCCTGNWPKXJL-UHFFFAOYSA-N 3-(2-cyanoethoxy)propanenitrile Chemical compound N#CCCOCCC#N BCGCCTGNWPKXJL-UHFFFAOYSA-N 0.000 description 1
- VODPCVZDUMBNGI-UHFFFAOYSA-N C(#N)CCO.C(CCCCC(=O)O)(=O)O Chemical compound C(#N)CCO.C(CCCCC(=O)O)(=O)O VODPCVZDUMBNGI-UHFFFAOYSA-N 0.000 description 1
- GHOKNUWKGVICQG-UHFFFAOYSA-N C=C.N#CC#N Chemical compound C=C.N#CC#N GHOKNUWKGVICQG-UHFFFAOYSA-N 0.000 description 1
- VBVOSYCJBPYDGH-UHFFFAOYSA-N C=CC#N.OC(=O)CCCCC(O)=O Chemical compound C=CC#N.OC(=O)CCCCC(O)=O VBVOSYCJBPYDGH-UHFFFAOYSA-N 0.000 description 1
- 210000001072 Colon Anatomy 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 241000282941 Rangifer tarandus Species 0.000 description 1
- 210000003932 Urinary Bladder Anatomy 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical class CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical class COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7508666 | 1966-11-16 | ||
| JP7508666 | 1966-11-16 | ||
| DEA0057345 | 1967-11-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1643604B1 DE1643604B1 (de) | 1972-08-17 |
| DE1643604C true DE1643604C (xx) | 1973-03-15 |
Family
ID=13565998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671643604 Granted DE1643604B1 (de) | 1966-11-16 | 1967-11-11 | Verfahren zum Gewinnen von Adipinsaeuredinitril |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3597331A (xx) |
| BE (1) | BE706573A (xx) |
| BR (1) | BR6794612D0 (xx) |
| CH (1) | CH487126A (xx) |
| DE (1) | DE1643604B1 (xx) |
| ES (1) | ES347183A1 (xx) |
| GB (1) | GB1205046A (xx) |
| LU (1) | LU54857A1 (xx) |
| NL (1) | NL6715362A (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3674653A (en) * | 1969-05-01 | 1972-07-04 | Asahi Chemical Ind | Method of the purification of catholytes |
| US4623447A (en) * | 1985-08-02 | 1986-11-18 | Pennzoil Company | Breaking middle phase emulsions |
| CN102400174B (zh) * | 2011-11-30 | 2014-07-16 | 青岛双瑞海洋环境工程股份有限公司 | 电解丙烯腈二聚制备己二腈的新型装置 |
| CA3163244A1 (en) * | 2019-12-30 | 2021-07-08 | Sanjay Dube | Process for recovering adiponitrile |
| CN112663078A (zh) * | 2020-11-03 | 2021-04-16 | 重庆大学 | 一种丙烯腈电解二聚制备己二腈的装置和方法 |
-
1967
- 1967-11-07 US US681203A patent/US3597331A/en not_active Expired - Lifetime
- 1967-11-10 BR BR194612/67A patent/BR6794612D0/pt unknown
- 1967-11-11 DE DE19671643604 patent/DE1643604B1/de active Granted
- 1967-11-13 NL NL6715362A patent/NL6715362A/xx unknown
- 1967-11-13 LU LU54857D patent/LU54857A1/xx unknown
- 1967-11-15 CH CH1597567A patent/CH487126A/de not_active IP Right Cessation
- 1967-11-15 ES ES347183A patent/ES347183A1/es not_active Expired
- 1967-11-16 GB GB52219/67A patent/GB1205046A/en not_active Expired
- 1967-11-16 BE BE706573D patent/BE706573A/xx not_active IP Right Cessation
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