TWI488834B - Purification of acetonitrile - Google Patents
Purification of acetonitrile Download PDFInfo
- Publication number
- TWI488834B TWI488834B TW102131116A TW102131116A TWI488834B TW I488834 B TWI488834 B TW I488834B TW 102131116 A TW102131116 A TW 102131116A TW 102131116 A TW102131116 A TW 102131116A TW I488834 B TWI488834 B TW I488834B
- Authority
- TW
- Taiwan
- Prior art keywords
- acetonitrile
- column
- line
- liquid
- mass
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title claims description 601
- 238000000746 purification Methods 0.000 title claims description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 135
- 238000006243 chemical reaction Methods 0.000 claims description 88
- 239000007788 liquid Substances 0.000 claims description 64
- 230000018044 dehydration Effects 0.000 claims description 58
- 238000006297 dehydration reaction Methods 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 39
- 239000003513 alkali Substances 0.000 claims description 36
- 238000004821 distillation Methods 0.000 claims description 22
- 239000008346 aqueous phase Substances 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 18
- 239000012295 chemical reaction liquid Substances 0.000 claims description 17
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 238000009835 boiling Methods 0.000 description 50
- 238000000926 separation method Methods 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 229910001868 water Inorganic materials 0.000 description 37
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 32
- 238000000354 decomposition reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 20
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 19
- 239000012535 impurity Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000004065 wastewater treatment Methods 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- 239000012071 phase Substances 0.000 description 12
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000945 filler Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 6
- 239000003507 refrigerant Substances 0.000 description 6
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 229960005489 paracetamol Drugs 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 acetic acid Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000000895 extractive distillation Methods 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 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
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration 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
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 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
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/03—Mononitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012192215 | 2012-08-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201414706A TW201414706A (zh) | 2014-04-16 |
| TWI488834B true TWI488834B (zh) | 2015-06-21 |
Family
ID=50183315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102131116A TWI488834B (zh) | 2012-08-31 | 2013-08-29 | Purification of acetonitrile |
Country Status (8)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104058994B (zh) * | 2014-07-02 | 2016-07-06 | 中国计量科学研究院 | 高纯乙腈及其制备方法和装置 |
| 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 |
| KR102256553B1 (ko) * | 2015-08-26 | 2021-05-25 | 차이나 페트로리움 앤드 케미컬 코포레이션 | 아세토니트릴의 정제 방법과 그 시스템 및 산성 폐수의 재활용 방법 |
| CN106316882B (zh) * | 2016-07-27 | 2018-01-30 | 中国计量科学研究院 | 一种电子级乙腈的制备方法 |
| CN109374795A (zh) * | 2018-09-20 | 2019-02-22 | 福建中医药大学 | 一种降低乙腈蒸发光散射检测器噪音的方法 |
Citations (2)
| 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 |
| JP2000128847A (ja) * | 1998-10-20 | 2000-05-09 | Asahi Chem Ind Co Ltd | アルカリの再使用方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4881816A (enrdf_load_stackoverflow) * | 1972-02-12 | 1973-11-01 | ||
| 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 |
| GB2249308B (en) * | 1990-10-30 | 1994-05-18 | G K Analytical Sciences Limite | Solvent purification |
| CN1102575C (zh) * | 2000-06-15 | 2003-03-05 | 中国石油化工集团公司 | 高纯乙腈精制中微量氢氰酸脱除方法 |
| CN101171233B (zh) * | 2005-05-10 | 2011-04-20 | 旭化成化学株式会社 | 高纯度乙腈及其制造方法 |
-
2013
- 2013-08-21 JP JP2014532954A patent/JP6038157B2/ja active Active
- 2013-08-21 WO PCT/JP2013/072323 patent/WO2014034500A1/ja active Application Filing
- 2013-08-21 SG SG11201501216XA patent/SG11201501216XA/en unknown
- 2013-08-21 CN CN201380045429.6A patent/CN104603101B/zh active Active
- 2013-08-21 IN IN1264DEN2015 patent/IN2015DN01264A/en unknown
- 2013-08-21 KR KR1020157002483A patent/KR101779678B1/ko active Active
- 2013-08-29 TW TW102131116A patent/TWI488834B/zh active
-
2015
- 2015-02-26 SA SA515360073A patent/SA515360073B1/ar unknown
Patent Citations (2)
| 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 |
| JP2000128847A (ja) * | 1998-10-20 | 2000-05-09 | Asahi Chem Ind Co Ltd | アルカリの再使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104603101A (zh) | 2015-05-06 |
| KR101779678B1 (ko) | 2017-09-18 |
| SG11201501216XA (en) | 2015-05-28 |
| JP6038157B2 (ja) | 2016-12-07 |
| JPWO2014034500A1 (ja) | 2016-08-08 |
| SA515360073B1 (ar) | 2016-02-13 |
| IN2015DN01264A (enrdf_load_stackoverflow) | 2015-07-03 |
| TW201414706A (zh) | 2014-04-16 |
| CN104603101B (zh) | 2017-03-01 |
| KR20150027281A (ko) | 2015-03-11 |
| WO2014034500A1 (ja) | 2014-03-06 |
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