CN114685362A - 一种2-甲基吡啶的分离方法 - Google Patents
一种2-甲基吡啶的分离方法 Download PDFInfo
- Publication number
- CN114685362A CN114685362A CN202011634048.XA CN202011634048A CN114685362A CN 114685362 A CN114685362 A CN 114685362A CN 202011634048 A CN202011634048 A CN 202011634048A CN 114685362 A CN114685362 A CN 114685362A
- Authority
- CN
- China
- Prior art keywords
- separation
- tower
- methylpyridine
- modulating agent
- separation method
- 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.)
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- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 title claims abstract description 105
- 238000000926 separation method Methods 0.000 title claims abstract description 83
- 239000002994 raw material Substances 0.000 claims abstract description 38
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 238000009835 boiling Methods 0.000 claims abstract description 16
- 239000003607 modifier Substances 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 55
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- RMQHJMMCLSJULX-UHFFFAOYSA-N 2,2,3,3-tetramethylhexane Chemical group CCCC(C)(C)C(C)(C)C RMQHJMMCLSJULX-UHFFFAOYSA-N 0.000 claims description 4
- VRVRZZWPKABUOE-UHFFFAOYSA-N 3,3,5-Trimethylheptane Chemical group CCC(C)CC(C)(C)CC VRVRZZWPKABUOE-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 25
- 238000004939 coking Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000000571 coke Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical group CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- 101000723939 Mus musculus Transcription factor HIVEP3 Proteins 0.000 description 1
- 229910017971 NH4BF4 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN202011634048.XA CN114685362B (zh) | 2020-12-31 | 2020-12-31 | 一种2-甲基吡啶的分离方法 |
Applications Claiming Priority (1)
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---|---|---|---|
CN202011634048.XA CN114685362B (zh) | 2020-12-31 | 2020-12-31 | 一种2-甲基吡啶的分离方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN114685362A true CN114685362A (zh) | 2022-07-01 |
CN114685362B CN114685362B (zh) | 2024-05-03 |
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Family Applications (1)
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CN202011634048.XA Active CN114685362B (zh) | 2020-12-31 | 2020-12-31 | 一种2-甲基吡啶的分离方法 |
Country Status (1)
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CN (1) | CN114685362B (zh) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5424482A (en) * | 1991-08-08 | 1995-06-13 | Elf Atochem N.A., Inc. | Process for preparing color-stable tertiary butyldiethanolamine |
US5738763A (en) * | 1996-07-08 | 1998-04-14 | Berg; Lloyd | Separation of 2-methyl-1-propanol from 2-methyl-1-butanol by extractive distillation |
JP2001172230A (ja) * | 1999-12-20 | 2001-06-26 | Sumitomo Chem Co Ltd | ジアリールアミン類の製造方法 |
CN1347871A (zh) * | 2001-10-30 | 2002-05-08 | 中国石化集团南京化工厂 | 连续精馏精制4-氨基二苯胺的办法 |
CN1403181A (zh) * | 2002-10-16 | 2003-03-19 | 南京师范大学 | 萃取蒸馏分离2-氯-5-甲基吡啶和2一氯-3-甲基吡啶的方法 |
CN107286025A (zh) * | 2017-07-12 | 2017-10-24 | 安徽广信农化股份有限公司 | 一种多菌灵主要原料邻苯二胺提纯的方法 |
US10577326B1 (en) * | 2018-10-30 | 2020-03-03 | Zhejiang Avilive Chemical, Co., Ltd. | Method for preparing 2-chloro-6-trichloromethylpyridine through liquid phase photochlorination of 2-methylpyridine |
-
2020
- 2020-12-31 CN CN202011634048.XA patent/CN114685362B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5424482A (en) * | 1991-08-08 | 1995-06-13 | Elf Atochem N.A., Inc. | Process for preparing color-stable tertiary butyldiethanolamine |
US5738763A (en) * | 1996-07-08 | 1998-04-14 | Berg; Lloyd | Separation of 2-methyl-1-propanol from 2-methyl-1-butanol by extractive distillation |
JP2001172230A (ja) * | 1999-12-20 | 2001-06-26 | Sumitomo Chem Co Ltd | ジアリールアミン類の製造方法 |
CN1347871A (zh) * | 2001-10-30 | 2002-05-08 | 中国石化集团南京化工厂 | 连续精馏精制4-氨基二苯胺的办法 |
CN1403181A (zh) * | 2002-10-16 | 2003-03-19 | 南京师范大学 | 萃取蒸馏分离2-氯-5-甲基吡啶和2一氯-3-甲基吡啶的方法 |
CN107286025A (zh) * | 2017-07-12 | 2017-10-24 | 安徽广信农化股份有限公司 | 一种多菌灵主要原料邻苯二胺提纯的方法 |
US10577326B1 (en) * | 2018-10-30 | 2020-03-03 | Zhejiang Avilive Chemical, Co., Ltd. | Method for preparing 2-chloro-6-trichloromethylpyridine through liquid phase photochlorination of 2-methylpyridine |
Non-Patent Citations (2)
Title |
---|
MIGUEL AYUSO ET AL.: "Separation of benzene from methylcycloalkanes by extractive distillation with cyano-based ionic liquids: Experimental and CPA EoS modelling", 《SEPARATION AND PURIFICATION TECHNOLOGY》, vol. 234, 24 September 2019 (2019-09-24), pages 1 - 12, XP085851572, DOI: 10.1016/j.seppur.2019.116128 * |
谷小会: "煤焦油分离方法及组分性质研究现状与展望", 《洁净煤技术》, vol. 24, no. 4, 30 April 2018 (2018-04-30), pages 1 - 6 * |
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CN114685362B (zh) | 2024-05-03 |
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TA01 | Transfer of patent application right |
Effective date of registration: 20240111 Address after: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Applicant after: CHINA PETROLEUM & CHEMICAL Corp. Applicant after: Sinopec (Dalian) Petrochemical Research Institute Co.,Ltd. Address before: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Applicant before: CHINA PETROLEUM & CHEMICAL Corp. Applicant before: DALIAN RESEARCH INSTITUTE OF PETROLEUM AND PETROCHEMICALS, SINOPEC Corp. |
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