DE2102886B2 - Verfahren zur Gewinnung von reinem Acetonitril - Google Patents
Verfahren zur Gewinnung von reinem AcetonitrilInfo
- Publication number
- DE2102886B2 DE2102886B2 DE2102886A DE2102886A DE2102886B2 DE 2102886 B2 DE2102886 B2 DE 2102886B2 DE 2102886 A DE2102886 A DE 2102886A DE 2102886 A DE2102886 A DE 2102886A DE 2102886 B2 DE2102886 B2 DE 2102886B2
- Authority
- DE
- Germany
- Prior art keywords
- acetonitrile
- distillation
- water
- extraction
- benzene
- 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.)
- Granted
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title claims description 162
- 238000000034 method Methods 0.000 title claims description 23
- 238000004821 distillation Methods 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- 238000000605 extraction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 150000008359 benzonitriles Chemical class 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- ADSJBTFAOIZAAQ-UHFFFAOYSA-N acetonitrile;benzene;hydrate Chemical compound O.CC#N.C1=CC=CC=C1 ADSJBTFAOIZAAQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000358 iron sulfate Inorganic materials 0.000 claims description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- SNZXMAHBUQXQSE-UHFFFAOYSA-N acetonitrile;benzene Chemical compound CC#N.C1=CC=CC=C1 SNZXMAHBUQXQSE-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- -1 n-pentane Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MXUPILKWZJJDFH-UHFFFAOYSA-N acetonitrile;prop-2-enenitrile Chemical compound CC#N.C=CC#N MXUPILKWZJJDFH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/03—Acrylonitrile
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2102886A DE2102886B2 (de) | 1971-01-22 | 1971-01-22 | Verfahren zur Gewinnung von reinem Acetonitril |
| NL7115835A NL7115835A (OSRAM) | 1971-01-22 | 1971-11-17 | |
| FR7145309A FR2122858A5 (OSRAM) | 1971-01-22 | 1971-12-16 | |
| GB165572A GB1377232A (en) | 1971-01-22 | 1972-01-13 | Production of pure acetonitrile |
| US217843A US3870746A (en) | 1971-01-22 | 1972-01-14 | Process for recovery of pure acetonitrile |
| JP754672A JPS5328413B1 (OSRAM) | 1971-01-22 | 1972-01-19 | |
| BE778325A BE778325A (fr) | 1971-01-22 | 1972-01-20 | Procede pour l'obtention d'acetonitrile pur |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2102886A DE2102886B2 (de) | 1971-01-22 | 1971-01-22 | Verfahren zur Gewinnung von reinem Acetonitril |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2102886A1 DE2102886A1 (de) | 1972-08-10 |
| DE2102886B2 true DE2102886B2 (de) | 1974-03-14 |
| DE2102886C3 DE2102886C3 (OSRAM) | 1974-11-07 |
Family
ID=5796597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2102886A Granted DE2102886B2 (de) | 1971-01-22 | 1971-01-22 | Verfahren zur Gewinnung von reinem Acetonitril |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3870746A (OSRAM) |
| JP (1) | JPS5328413B1 (OSRAM) |
| BE (1) | BE778325A (OSRAM) |
| DE (1) | DE2102886B2 (OSRAM) |
| FR (1) | FR2122858A5 (OSRAM) |
| GB (1) | GB1377232A (OSRAM) |
| NL (1) | NL7115835A (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141826A (en) * | 1977-03-30 | 1979-02-27 | The Standard Oil Company | Treatment of acrylonitrile waste water with activated carbon |
| WO1993023366A1 (en) * | 1992-05-21 | 1993-11-25 | Cryodyne Technologies Inc. | Method for purification of acetonitrile |
| US5426208A (en) * | 1992-05-21 | 1995-06-20 | Cryodyne Technologies, Inc. | Method of purification of acetonitrile |
| JP4750345B2 (ja) * | 2000-07-18 | 2011-08-17 | イネオス・ユーエスエイ・エルエルシー | 改良されたアセトニトリルの精製及び回収方法 |
| US20120073954A1 (en) * | 2010-09-28 | 2012-03-29 | Romas Cesas | Recovery of acetonitrile from a waste stream |
| CN109052774A (zh) * | 2018-06-21 | 2018-12-21 | 天津中昊天久工程技术有限公司 | 溶剂可循环高效乙腈废水回收系统 |
| CN113461568A (zh) * | 2021-06-24 | 2021-10-01 | 索闻特环保科技(上海)有限公司 | 处理乙腈废液中甲苯的方法 |
| CN114634423B (zh) * | 2022-02-25 | 2024-08-27 | 国药集团威奇达药业有限公司 | 从7-act合成产生的乙腈母液中连续回收乙腈的方法 |
| JP2025512885A (ja) | 2022-03-30 | 2025-04-22 | ドナルドソン カンパニー，インコーポレイティド | 溶媒を再利用するためのシステム及び方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2463629A (en) * | 1946-10-30 | 1949-03-08 | American Cyanamid Co | Azeotropic distillation of acetonitrile-trichloracetonitrile mixtures |
| NL262785A (OSRAM) * | 1960-04-07 | |||
| DE1212962B (de) * | 1960-08-12 | 1966-03-24 | Knapsack Ag | Verfahren zur Abtrennung und Gewinnung von Acrylsaeurenitril und Ammoniak aus gasfoermigen Gemischen durch Auswaschen |
| US3281450A (en) * | 1963-09-27 | 1966-10-25 | Goodrich Co B F | Purification of acetonitrile |
| US3451899A (en) * | 1965-12-21 | 1969-06-24 | Badger Co | Purification of acetonitrile by an azeotropic distillation method |
-
1971
- 1971-01-22 DE DE2102886A patent/DE2102886B2/de active Granted
- 1971-11-17 NL NL7115835A patent/NL7115835A/xx not_active Application Discontinuation
- 1971-12-16 FR FR7145309A patent/FR2122858A5/fr not_active Expired
-
1972
- 1972-01-13 GB GB165572A patent/GB1377232A/en not_active Expired
- 1972-01-14 US US217843A patent/US3870746A/en not_active Expired - Lifetime
- 1972-01-19 JP JP754672A patent/JPS5328413B1/ja active Pending
- 1972-01-20 BE BE778325A patent/BE778325A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2102886C3 (OSRAM) | 1974-11-07 |
| NL7115835A (OSRAM) | 1972-07-25 |
| JPS5328413B1 (OSRAM) | 1978-08-15 |
| US3870746A (en) | 1975-03-11 |
| BE778325A (fr) | 1972-05-16 |
| GB1377232A (en) | 1974-12-11 |
| DE2102886A1 (de) | 1972-08-10 |
| FR2122858A5 (OSRAM) | 1972-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |