TWI453185B - Purification of acetonitrile - Google Patents
Purification of acetonitrile Download PDFInfo
- Publication number
- TWI453185B TWI453185B TW102110542A TW102110542A TWI453185B TW I453185 B TWI453185 B TW I453185B TW 102110542 A TW102110542 A TW 102110542A TW 102110542 A TW102110542 A TW 102110542A TW I453185 B TWI453185 B TW I453185B
- Authority
- TW
- Taiwan
- Prior art keywords
- column
- reboiler
- acetonitrile
- distillation column
- pressure
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title claims description 390
- 238000000746 purification Methods 0.000 title claims description 35
- 238000004821 distillation Methods 0.000 claims description 134
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- 230000018044 dehydration Effects 0.000 claims description 21
- 238000006297 dehydration reaction Methods 0.000 claims description 21
- 239000012071 phase Substances 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 11
- 239000008346 aqueous phase Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 description 173
- 238000000926 separation method Methods 0.000 description 171
- 239000000047 product Substances 0.000 description 83
- 239000007788 liquid Substances 0.000 description 45
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000012535 impurity Substances 0.000 description 23
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 21
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
- 239000000498 cooling water Substances 0.000 description 10
- 238000012546 transfer Methods 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 238000005265 energy consumption Methods 0.000 description 8
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000003507 refrigerant Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000002411 adverse Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 102000053602 DNA Human genes 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 2
- 230000006820 DNA synthesis Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000895 extractive distillation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical group C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- -1 magnetic Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical group CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/007—Energy recuperation; Heat pumps
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012070086 | 2012-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201343616A TW201343616A (zh) | 2013-11-01 |
| TWI453185B true TWI453185B (zh) | 2014-09-21 |
Family
ID=49259862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102110542A TWI453185B (zh) | 2012-03-26 | 2013-03-25 | Purification of acetonitrile |
Country Status (7)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3012140B1 (fr) * | 2013-10-18 | 2016-08-26 | Arkema France | Unite et procede pour la purification de methacrylate de methyle brut |
| US10336690B2 (en) * | 2014-02-24 | 2019-07-02 | Honeywell International Inc. | Methods and systems for processing an acetonitrile waste stream |
| CN104193651B (zh) * | 2014-08-15 | 2017-01-18 | 江苏九天高科技股份有限公司 | 一种用于醋酸氨化合成乙腈的精制方法及装置 |
| CN106496069B (zh) * | 2015-09-06 | 2024-05-03 | 中国石油化工股份有限公司 | 乙腈精制系统的节能装置和节能方法 |
| CN114870421A (zh) * | 2015-11-16 | 2022-08-09 | 英尼奥斯欧洲股份公司 | 头馏分塔泵循环 |
| CN109704990B (zh) * | 2017-10-26 | 2022-02-01 | 中国石油化工股份有限公司 | 高纯乙腈的精制方法 |
| CN107812393A (zh) * | 2017-10-27 | 2018-03-20 | 烟台国邦化工机械科技有限公司 | 一种甲醇三效精馏系统及工艺 |
| CN110437079A (zh) * | 2019-08-26 | 2019-11-12 | 山东齐鲁石化工程有限公司 | 从废水中回收二乙胺和三乙胺的工艺系统 |
| CN111359247A (zh) * | 2020-03-24 | 2020-07-03 | 常州工程职业技术学院 | 一种计算间歇精馏分离所需理论塔板数的方法 |
| EP4208439A1 (en) * | 2020-09-04 | 2023-07-12 | Ascend Performance Materials Operations LLC | Acetonitrile separation process |
| CN114213282B (zh) * | 2021-12-21 | 2024-07-30 | 山东博苑医药化学股份有限公司 | 一种含酸乙腈废溶剂的乙腈回收方法 |
| CN115180756A (zh) * | 2022-06-10 | 2022-10-14 | 武汉北湖云峰环保科技有限公司 | 一种乙腈废液的纯化回收装置及方法 |
| CN116855274A (zh) * | 2023-08-21 | 2023-10-10 | 天津奥展兴达化工技术有限公司 | 一种石油常减压蒸馏装置及其工艺 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308108A (en) * | 1979-03-28 | 1981-12-29 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for purification of crude acetonitrile |
| CN1524849A (zh) * | 2003-01-14 | 2004-09-01 | 纯化丙烯腈的方法中冷凝的骤冷塔顶馏出物的循环 | |
| CN101171233A (zh) * | 2005-05-10 | 2008-04-30 | 旭化成化学株式会社 | 高纯度乙腈及其制造方法 |
| CN101648888A (zh) * | 2009-09-21 | 2010-02-17 | 浙江新化化工股份有限公司 | 一种乙腈的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55143949A (en) * | 1979-04-26 | 1980-11-10 | Asahi Chem Ind Co Ltd | Recovery of purified acetonitrile |
| JPS55153757A (en) | 1979-05-18 | 1980-11-29 | Asahi Chem Ind Co Ltd | Purification of crude acetonitrile by dehydration |
| JPS55129257A (en) * | 1979-03-28 | 1980-10-06 | Asahi Chem Ind Co Ltd | Purification of acetonitrile containing hydrogen cyanide |
| JPH03246269A (ja) | 1990-02-21 | 1991-11-01 | Asahi Chem Ind Co Ltd | アセトニトリルの増収方法 |
| TW402583B (en) * | 1996-04-10 | 2000-08-21 | Standard Oil Co | Purification of acetonitrile by a distillative recovery/ion exchange resin treatment process |
| JPH1135542A (ja) * | 1997-07-09 | 1999-02-09 | Standard Oil Co:The | 蒸留回収／イオン交換樹脂処理プロセスによるアセトニトリルの精製 |
| JP2000086592A (ja) * | 1998-09-04 | 2000-03-28 | Daicel Chem Ind Ltd | 炭酸ジエステルの精製方法および精製装置 |
| JP2000136154A (ja) * | 1998-10-30 | 2000-05-16 | Mitsubishi Chemicals Corp | １，２−ジクロロエタンの精製方法 |
| CN101890249A (zh) * | 2010-07-22 | 2010-11-24 | 蓝仁水 | 一种三馏分精馏分离的节能工艺方法 |
| KR101524956B1 (ko) * | 2010-08-25 | 2015-06-01 | 유오피 엘엘씨 | 중질 탄화수소 증류에서의 에너지 보존 |
| CN102516119B (zh) * | 2011-12-15 | 2014-04-30 | 惠生工程（中国）有限公司 | 一种连续低能耗的乙腈精制工艺 |
-
2013
- 2013-03-22 IN IN7599DEN2014 patent/IN2014DN07599A/en unknown
- 2013-03-22 WO PCT/JP2013/058368 patent/WO2013146609A1/ja active Application Filing
- 2013-03-22 KR KR1020147020166A patent/KR101648653B1/ko active Active
- 2013-03-22 CN CN201380014926.XA patent/CN104203909B/zh active Active
- 2013-03-22 JP JP2014507830A patent/JP6143744B2/ja active Active
- 2013-03-22 SG SG11201405296QA patent/SG11201405296QA/en unknown
- 2013-03-25 TW TW102110542A patent/TWI453185B/zh active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308108A (en) * | 1979-03-28 | 1981-12-29 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for purification of crude acetonitrile |
| CN1524849A (zh) * | 2003-01-14 | 2004-09-01 | 纯化丙烯腈的方法中冷凝的骤冷塔顶馏出物的循环 | |
| CN101171233A (zh) * | 2005-05-10 | 2008-04-30 | 旭化成化学株式会社 | 高纯度乙腈及其制造方法 |
| CN101648888A (zh) * | 2009-09-21 | 2010-02-17 | 浙江新化化工股份有限公司 | 一种乙腈的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104203909A (zh) | 2014-12-10 |
| TW201343616A (zh) | 2013-11-01 |
| JP6143744B2 (ja) | 2017-06-07 |
| WO2013146609A1 (ja) | 2013-10-03 |
| IN2014DN07599A (enrdf_load_stackoverflow) | 2015-05-15 |
| SG11201405296QA (en) | 2014-11-27 |
| KR101648653B1 (ko) | 2016-08-16 |
| CN104203909B (zh) | 2016-07-20 |
| KR20140112522A (ko) | 2014-09-23 |
| JPWO2013146609A1 (ja) | 2015-12-14 |
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