CN107382850A - A kind of 2 methylquinoline and its isomer and the separation method of isoquinolin - Google Patents
A kind of 2 methylquinoline and its isomer and the separation method of isoquinolin Download PDFInfo
- Publication number
- CN107382850A CN107382850A CN201710872582.6A CN201710872582A CN107382850A CN 107382850 A CN107382850 A CN 107382850A CN 201710872582 A CN201710872582 A CN 201710872582A CN 107382850 A CN107382850 A CN 107382850A
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- CN
- China
- Prior art keywords
- methylquinolines
- methylquinoline
- isomer
- isoquinolin
- purity
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of 2 methylquinoline and its isomer and the separation method of isoquinolin, belong to technical field of petrochemical industry.Tarry distillate containing 2 methylquinolines is removed into isoquinolin by rectification under vacuum, obtains 2 methylquinoline cuts of higher degree；After vacuum distillation, at the uniform velocity heat up, continue to be evaporated under reduced pressure, obtain 2 methylquinoline cuts of high-purity；2 methylquinoline cuts of above-mentioned high-purity and the chain compound containing amino are subjected to complex reaction in a two-phase system, according to the complexing coefficient of complex compound, the isomer of 2 methylquinolines removed；Again by hydrolysis, you can obtain 2 methylquinoline cuts.The present invention is removed containing the nitrogen heterocyclic in tar using first rectifying, is then again separated 2 methylquinolines with its isomer with chemical method, and so as to realize that improving 2 methylquinoline purity can reach more than 93%, yield can bring up to more than 86%.
Description
Technical field
The invention belongs to technical field of petrochemical industry, and in particular to a kind of 2- methylquinolines and its isomer and isoquinoline
The separation method of quinoline.
Background technology
Coal tar is the main source of China's quinoline, isoquinolin and a variety of methylquinolines.In the last few years, quinoline on medical industry
The newtype drug of quinoline, isoquinolin and a variety of methylquinolines is increasingly developed out.From initial antimalarial agent to local anesthetic
Thing, from antibacterium, antifungal to antitumor, resistant to infection medicine；Agriculturally from herbicide to bactericide, insecticide, not only
Effectively and toxicity and residual are relatively low.In addition, quinoline, isoquinolin and methylquinoline or rubber anti-ageing agent, photosensitive agent,
Anticorrosive metal agent etc., it is widely used.But quinoline and a variety of methylquinolines are extracted in isoquinolin raffinate, while obtain quinoline
Quinoline, the method for isoquinolin product and technique are very limited, and main cause is that physicochemical property is too close to.Such as：2- methylquinolines and 8-
The boiling point of methylquinoline is only poor 0.5 DEG C, and the boiling point of isoquinolin and 8- methylquinolines is also only poor 5 DEG C, it is difficult to be divided with rectification method
From extraction.And -22 DEG C of 6- methylquinolines fusing point, -2 DEG C of 2- methylquinolines fusing point, -8 DEG C of fusing point, the 3- methylquinoline fusing points of quinoline
15 DEG C, the proximity of 9-10 DEG C of 4- methylquinolines fusing point disturb freezing and crystallizing partition method again.
Although can separate 2- methylquinolines and isoquinolin, 2- methylquinolines and itself isomer can not be had
Effect separation.If directly 2- methylquinolines and the isomer of its own are separated without rectifying, due to isoquinolin
Presence and influence, analytical effect is excessively poor.
The content of the invention
The defects of to overcome present in prior art, the present invention provide a kind of 2- methylquinolines and its isomer and different
The separation method of quinoline, can solve the problem that above-mentioned technical problem.
Technical scheme is used by the invention solves its technical problem：It is different with dividing with it to design a kind of 2- methylquinolines
The separation method of structure body and isoquinolin, carry out successively as steps described below：
Step 1：Tarry distillate containing 2- methylquinolines is removed into isoquinolin by rectification under vacuum, obtains the 2- of higher degree
Methylquinoline cut；After vacuum distillation, at the uniform velocity heat up, continue to be evaporated under reduced pressure, obtain the 2- methylquinoline cuts of high-purity；
Step 2：The 2- methylquinolines cut of above-mentioned high-purity is carried out in a two-phase system with the chain compound containing amino
Complex reaction, according to the complexing coefficient of complex compound, the isomer of 2- methylquinolines is removed；Again by hydrolysis, you can obtain
Obtain 2- methylquinoline cuts.
Preferably, the 2- methylquinolines cut of the higher degree described in step 1 is 50%-60%；Described in step 1
The 2- methylquinolines cut of high-purity is 61%-80%.
Preferably, the chain compound containing amino described in step 2 is R- (- NH2)2, wherein R=CO, CS or other
Small molecule chain-like groups；x=1、2.
Preferably, the organic phase in two systems described in step 2 is one kind or one kind in benzene,toluene,xylene
More than.
Preferably, the 2- methylquinolines purity described in step 2 is more than 93%.
Beneficial effect is possessed by the present invention：
1st, the present invention is removed containing the nitrogen heterocyclic in tar using first rectifying, then again with chemical method by 2- methylquinolines and
Its isomer separates, and so as to realize that improving 2- methylquinoline purity can reach more than 93%, yield can bring up to more than 86%.
Embodiment
Embodiment one
A kind of 2- methylquinolines and its isomer and the separation method of isoquinolin, are carried out successively as steps described below：
Step 1：Tarry distillate containing 2- methylquinolines is removed into isoquinolin by rectification under vacuum, obtains the 2- of higher degree
Methylquinoline cut；After vacuum distillation, at the uniform velocity heat up, continue to be evaporated under reduced pressure, obtain the 2- methylquinoline cuts of high-purity；
Step 2：The 2- methylquinolines cut of above-mentioned high-purity is carried out in a two-phase system with the chain compound containing amino
Complex reaction, according to the complexing coefficient of complex compound, the isomer of 2- methylquinolines is removed；Again by hydrolysis, you can obtain
Obtain 2- methylquinoline cuts.
The 2- methylquinolines cut of higher degree described in step 1 is 50%；The 2- of high-purity described in step 1
Methylquinoline cut is 61%.
The chain compound containing amino described in step 2 is R- (- NH2)2, wherein R=CO, CS or other small molecule
Chain-like groups；x=1、2.
The organic phase in two systems described in step 2 is the one or more in benzene,toluene,xylene.
2- methylquinolines purity described in step 2 is 93%.
Embodiment two
A kind of 2- methylquinolines and its isomer and the separation method of isoquinolin, are carried out successively as steps described below：
Step 1：Tarry distillate containing 2- methylquinolines is removed into isoquinolin by rectification under vacuum, obtains the 2- of higher degree
Methylquinoline cut；After vacuum distillation, at the uniform velocity heat up, continue to be evaporated under reduced pressure, obtain the 2- methylquinoline cuts of high-purity；
Step 2：The 2- methylquinolines cut of above-mentioned high-purity is carried out in a two-phase system with the chain compound containing amino
Complex reaction, according to the complexing coefficient of complex compound, the isomer of 2- methylquinolines is removed；Again by hydrolysis, you can obtain
Obtain 2- methylquinoline cuts.
The 2- methylquinolines cut of higher degree described in step 1 is 55%；The 2- of high-purity described in step 1
Methylquinoline cut is 70%.
The chain compound containing amino described in step 2 is R- (- NH2)2, wherein R=CO, CS or other small molecule
Chain-like groups；x=1、2.
The organic phase in two systems described in step 2 is the one or more in benzene,toluene,xylene.
2- methylquinolines purity described in step 2 is 95%.
Embodiment three
A kind of 2- methylquinolines and its isomer and the separation method of isoquinolin, are carried out successively as steps described below：
Step 1：Tarry distillate containing 2- methylquinolines is removed into isoquinolin by rectification under vacuum, obtains the 2- of higher degree
Methylquinoline cut；After vacuum distillation, at the uniform velocity heat up, continue to be evaporated under reduced pressure, obtain the 2- methylquinoline cuts of high-purity；
Step 2：The 2- methylquinolines cut of above-mentioned high-purity is carried out in a two-phase system with the chain compound containing amino
Complex reaction, according to the complexing coefficient of complex compound, the isomer of 2- methylquinolines is removed；Again by hydrolysis, you can obtain
Obtain 2- methylquinoline cuts.
The 2- methylquinolines cut of higher degree described in step 1 is 60%；The 2- of high-purity described in step 1
Methylquinoline cut is 80%.
The chain compound containing amino described in step 2 is R- (- NH2)2, wherein R=CO, CS or other small molecule
Chain-like groups；x=1、2.
The organic phase in two systems described in step 2 is the one or more in benzene,toluene,xylene.
2- methylquinolines purity described in step 2 is 98%.
Claims (5)
1. a kind of 2- methylquinolines and its isomer and the separation method of isoquinolin, it is characterised in that：As steps described below
Carry out successively：
Step 1：Tarry distillate containing 2- methylquinolines is removed into isoquinolin by rectification under vacuum, obtains the 2- of higher degree
Methylquinoline cut；After vacuum distillation, at the uniform velocity heat up, continue to be evaporated under reduced pressure, obtain the 2- methylquinoline cuts of high-purity；
Step 2：The 2- methylquinolines cut of above-mentioned high-purity is carried out in a two-phase system with the chain compound containing amino
Complex reaction, according to the complexing coefficient of complex compound, the isomer of 2- methylquinolines is removed；Again by hydrolysis, you can obtain
Obtain 2- methylquinoline cuts.
2. a kind of 2- methylquinolines according to claim 1 and its isomer and the separation method of isoquinolin, it is special
Sign is：The 2- methylquinolines cut of higher degree described in step 1 is 50%-60%；High-purity described in step 1
2- methylquinolines cut is 61%-80%.
3. a kind of 2- methylquinolines according to claim 1 and its isomer and the separation method of isoquinolin, it is special
Sign is：The chain compound containing amino described in step 2 is R- (- NH2)2, wherein R=CO, CS or other small molecule chain
Shape group；x=1、2.
4. a kind of 2- methylquinolines according to claim 1 and its isomer and the separation method of isoquinolin, it is special
Sign is：The organic phase in two systems described in step 2 is the one or more in benzene,toluene,xylene.
5. a kind of 2- methylquinolines according to claim 1 and its isomer and the separation method of isoquinolin, it is special
Sign is：2- methylquinolines purity described in step 2 is more than 93%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108395400A (en) * | 2017-02-08 | 2018-08-14 | 鞍钢股份有限公司 | A kind of technique of industrialized production 2- methylquinoline fractions |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB736589A (en) * | 1951-11-20 | 1955-09-14 | Midland Tar Distillers Ltd | Improvements in the separation of quinaldine from other bases |
| JPS5636459A (en) * | 1979-09-03 | 1981-04-09 | Nippon Steel Chem Co Ltd | Separation of isoquinoline |
| CN1253133A (en) * | 1998-11-04 | 2000-05-17 | 拉特格斯Vft公开股份有限公司 | Method for purifying isoquinoline |
| CN102372671A (en) * | 2011-10-26 | 2012-03-14 | 上海煦旻化工科技发展有限公司 | Preparation method for 2-methylquinoline |
| CN104230797A (en) * | 2014-08-22 | 2014-12-24 | 山西永东化工股份有限公司 | Preparation method of quinolone, isoquinoline and methylquinolines |
| CN104788371A (en) * | 2015-04-20 | 2015-07-22 | 黄骅市信诺立兴精细化工股份有限公司 | Method for extracting 2-methylquinoline from isoquinoline stillage residual liquor |
-
2017
- 2017-09-25 CN CN201710872582.6A patent/CN107382850A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB736589A (en) * | 1951-11-20 | 1955-09-14 | Midland Tar Distillers Ltd | Improvements in the separation of quinaldine from other bases |
| JPS5636459A (en) * | 1979-09-03 | 1981-04-09 | Nippon Steel Chem Co Ltd | Separation of isoquinoline |
| CN1253133A (en) * | 1998-11-04 | 2000-05-17 | 拉特格斯Vft公开股份有限公司 | Method for purifying isoquinoline |
| CN102372671A (en) * | 2011-10-26 | 2012-03-14 | 上海煦旻化工科技发展有限公司 | Preparation method for 2-methylquinoline |
| CN104230797A (en) * | 2014-08-22 | 2014-12-24 | 山西永东化工股份有限公司 | Preparation method of quinolone, isoquinoline and methylquinolines |
| CN104788371A (en) * | 2015-04-20 | 2015-07-22 | 黄骅市信诺立兴精细化工股份有限公司 | Method for extracting 2-methylquinoline from isoquinoline stillage residual liquor |
Non-Patent Citations (2)
| Title |
|---|
| 吕苗.: "用精馏法从喹啉残油中提取异喹啉", 《燃料与化工》 * |
| 杨丽荣.: "喹啉合成工艺研究", 《当代化工研究》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108395400A (en) * | 2017-02-08 | 2018-08-14 | 鞍钢股份有限公司 | A kind of technique of industrialized production 2- methylquinoline fractions |
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Effective date of registration: 20180928 Address after: 056500 North Village of Chen Zhuang village, Cixian village, Handan, Hebei (Cixian Coal Chemical Industry Park) Applicant after: Hebei Sinochem Xinbao Chemical Technology Co., Ltd. Address before: 056000 North Village of Chen Zhuang village, Cixian village, Handan, Hebei (Cixian Coal Chemical Industry Park) Applicant before: Jia Hailiang |
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Application publication date: 20171124 |