CN110922288A - Post-treatment purification method of high-boiling-point biphenyl liquid crystal material - Google Patents
Post-treatment purification method of high-boiling-point biphenyl liquid crystal material Download PDFInfo
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- CN110922288A CN110922288A CN201811097720.9A CN201811097720A CN110922288A CN 110922288 A CN110922288 A CN 110922288A CN 201811097720 A CN201811097720 A CN 201811097720A CN 110922288 A CN110922288 A CN 110922288A
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- boiling
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- crystal material
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000746 purification Methods 0.000 title claims abstract description 19
- 235000010290 biphenyl Nutrition 0.000 title claims abstract description 17
- 239000004305 biphenyl Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 title claims abstract description 15
- 238000004440 column chromatography Methods 0.000 claims abstract description 14
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000926 separation method Methods 0.000 claims abstract description 11
- 239000000741 silica gel Substances 0.000 claims abstract description 11
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 7
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012535 impurity Substances 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000012043 crude product Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- KOYFRWHBYJOGGO-UHFFFAOYSA-N 1-heptyl-4-(4-methylphenyl)benzene Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C)C=C1 KOYFRWHBYJOGGO-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- -1 4-methyl-4' -butenyl biphenyl Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000003321 amplification Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention provides a post-treatment purification method of a high-boiling-point biphenyl liquid crystal material, which comprises the following steps: and (3) carrying out column chromatography separation on the crude biphenyl products with high boiling points by using four or more than four chromatographic columns, and collecting the products, wherein the stationary phases of the four or more than four chromatographic columns are one or more of silica gel, alumina, activated carbon and aluminum silicate. The post-treatment purification method of the high-boiling-point biphenyl liquid crystal material achieves the purification purpose by utilizing different polarities of a plurality of organic solvents and adopting a multi-column series column chromatography method, and has the advantages of high purification precision, less impurities and low cost.
Description
Technical Field
The invention relates to a purification method, in particular to a post-treatment purification method of a biphenyl liquid crystal material with a high boiling point.
Background
The column chromatography is also called column chromatography. Chromatographic separation technology has been used for centuries, and is a physical and chemical separation and analysis method, column chromatography is also a kind of chromatographic separation, and when two phases move relatively, solute is balanced between the two phases for many times by utilizing the difference of acting force (distribution, adsorption, ion exchange, etc.) between different solutes (samples) and stationary and mobile phases, so that the solutes are separated from each other.
The column chromatography is mainly used for adsorbing small molecular organic impurities and ionic impurities. The liquid crystal material is balanced for many times between the two phases through different acting forces of the mobile phase and the stationary phase, so that the separation effect is achieved. The current chromatographic column filler is silica gel and alumina, and the column pressure is normal pressure. The separation effect and the efficiency are not satisfactory.
High Performance Liquid Chromatography (HPLC) is currently the most popular chromatographic technique, has extremely wide application in analytical chemistry, and is now a common or even standard analytical technique. However, due to the complex and expensive equipment, difficult process amplification and other factors, the preparative liquid chromatography technology is more applied in the field of biomedicine, but is less used in the traditional field, particularly in the separation of products produced in large scale.
Disclosure of Invention
The invention aims to provide a post-treatment purification method of high-boiling-point biphenyl liquid crystal materials, which has high purification precision and convenient operation.
The technical scheme of the invention is as follows:
a post-treatment purification method of high-boiling-point biphenyl liquid crystal materials comprises the following steps: and (3) carrying out column chromatography separation on the crude biphenyl products with high boiling points by using four or more than four chromatographic columns, and collecting the products, wherein the stationary phases of the four or more than four chromatographic columns are one or more of silica gel, alumina, activated carbon and aluminum silicate.
The stationary phase of the four or more than four chromatographic columns is one or more of silica gel, alumina, active carbon and aluminum silicate.
The mobile phase comprises a component A and a component B, wherein the component A is selected from one or more of methanol, isopropanol and ethyl acetate, and the component B is selected from one or more of petroleum ether, n-hexane and isopentane.
The volume ratio of the component A to the component B is 1: 5-1: 10.
And applying pressure in the column chromatography separation process.
The pressurizing pressure is 0.3-0.5 Mpa.
The diameter-height ratio of the chromatographic column is 1: 5-1: 15.
the chromatographic columns are connected in series.
Has the advantages that: the invention utilizes the principle that organic solvents have different polarities, and performs column chromatography separation by using four or more than four chromatographic columns, thereby increasing the separation times, improving the purity of purification, reducing the cost and being convenient to operate.
Detailed Description
Example 1
1. Preparing 400mg of 4-methyl-4' -heptyl biphenyl crude product into a solution by using methanol, filtering to remove insoluble substances, and concentrating;
2. the mass ratio of the crude product to the crude product is 5: 1, taking a petroleum ether ethyl acetate mixed solvent as a mobile phase, wherein the diameter-height ratio is 3 cm: using silica gel, silica gel and active carbon as stationary phases for 18cm four chromatographic columns respectively, using the columns in series, adding 0.3Mpa pressure column for chromatography, and collecting 4-methyl-4' -heptyl biphenyl products. Purity by HPLC was 99.7%.
Example 2
1. Preparing 400mg of 4-methyl-4' -heptyl biphenyl crude product into a solution by using methanol, filtering to remove insoluble substances, and concentrating;
2. the crude product takes petroleum ether ethyl acetate mixed solvent with the mass ratio of 8:1 as a mobile phase, and the diameter-height ratio is 2 cm: silica gel, aluminum silicate and active carbon are used as stationary phases of four chromatography columns of 14cm respectively, the stationary phases are used in series, a pressure column chromatography of 0.3Mpa is added, and a 4-methyl-4' -heptyl biphenyl product is collected. Purity by HPLC was 99.8%.
Example 3
1. Preparing 4-methyl-4' -heptyl biphenyl crude product 1g into a solution by using methanol, filtering to remove insoluble substances, and concentrating;
2. the crude product uses a mixed solvent of isopentane and isopropanol with a mass ratio of 6:1 as a mobile phase, and the diameter-height ratio is 2 cm: silica gel, alumina and active carbon are used as stationary phases of 22cm four chromatographic columns respectively, the four chromatographic columns are used in series, 0.4MPa pressure column chromatography is added, and 4-methyl-4' -heptyl biphenyl products are collected. Purity by HPLC was 99.5%.
Example 4
1. Preparing 4-methyl-4' -butenyl biphenyl crude product 2g into solution with propanol, filtering to remove insoluble substances, and concentrating;
2. the crude product uses a mixed solvent of petroleum ether and methanol with a mass ratio of 9:1 as a mobile phase, and the diameter-height ratio is 2 cm: using silica gel, alumina and active carbon as stationary phases for four chromatographic columns of 16cm respectively, using the stationary phases in series, adding 0.4Mpa pressure column chromatography, and collecting 4-methyl-4' -butenyl biphenyl products. Purity by HPLC was 99.9%.
Example 5
1. Preparing 4-methyl-4' -butenyl biphenyl crude product 3g into solution with propanol, filtering to remove insoluble substances, and concentrating;
2. the crude product uses a mixed solvent of petroleum ether and methanol with a mass ratio of 7:1 as a mobile phase, and the diameter-height ratio is 3 cm: using silica gel, aluminum silicate and active carbon as stationary phases for 21cm four chromatographic columns respectively, connecting in series, adding 0.5Mpa pressure column for chromatography, and collecting 4-methyl-4' -butenyl biphenyl product. Purity by HPLC was 99.8%.
Claims (7)
1. A post-treatment purification method of a high-boiling-point biphenyl liquid crystal material is characterized by comprising the following steps: carrying out column chromatography separation on the crude biphenyl products with high boiling points by four or more than four chromatographic columns, and collecting the products;
the stationary phase of the four or more than four chromatographic columns is one or more of silica gel, alumina, active carbon and aluminum silicate.
2. The method for post-treatment purification of high-boiling-point biphenyl liquid crystal material according to claim 1, wherein the mobile phase comprises component A and component B, wherein component A is selected from one or more of methanol, isopropanol and ethyl acetate, and component B is selected from one or more of petroleum ether, n-hexane and isopentane.
3. The method for post-treatment purification of high-boiling-point biphenyl liquid crystal material according to claim 2, wherein the volume ratio of the component A to the component B is 1:5 to 1: 10.
4. The method for post-treatment purification of high-boiling-point biphenyl liquid crystal material according to any one of claims 1 to 3, wherein pressure is applied during the column chromatography separation process.
5. The method for post-treatment purification of high boiling point biphenyl liquid crystal material according to any of claims 1 to 3, wherein the pressure of the pressurization is 0.3 to 0.5 MPa.
6. The method for post-treatment purification of high-boiling-point biphenyl liquid crystal material according to any one of claims 1 to 3, wherein the chromatography column has a diameter-height ratio of 1: 5-1: 15.
7. the method for post-treatment purification of high-boiling-point biphenyl liquid crystal materials according to any one of claims 1 to 3, wherein the chromatographic columns are connected in series.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811097720.9A CN110922288A (en) | 2018-09-20 | 2018-09-20 | Post-treatment purification method of high-boiling-point biphenyl liquid crystal material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811097720.9A CN110922288A (en) | 2018-09-20 | 2018-09-20 | Post-treatment purification method of high-boiling-point biphenyl liquid crystal material |
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| CN110922288A true CN110922288A (en) | 2020-03-27 |
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| CN201811097720.9A Pending CN110922288A (en) | 2018-09-20 | 2018-09-20 | Post-treatment purification method of high-boiling-point biphenyl liquid crystal material |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367741A (en) * | 2008-09-24 | 2009-02-18 | 上海大学 | 4'-methoxy-2-amino--5-acetyl biphenyl and synthesis thereof |
| CN104311377A (en) * | 2014-08-29 | 2015-01-28 | 浙江工业大学 | Synthesis method of biphenyl compounds |
| CN106674022A (en) * | 2015-11-10 | 2017-05-17 | 深圳超多维光电子有限公司 | Liquid crystal intermediate and preparation method of liquid crystal material |
| CN106966979A (en) * | 2017-04-22 | 2017-07-21 | 桂林理工大学 | The synthetic method of benzophenanthrene benzyloxy alkynes biphenyl alkynes benzene Qiao Lian perylene list imines dihexyls |
-
2018
- 2018-09-20 CN CN201811097720.9A patent/CN110922288A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367741A (en) * | 2008-09-24 | 2009-02-18 | 上海大学 | 4'-methoxy-2-amino--5-acetyl biphenyl and synthesis thereof |
| CN104311377A (en) * | 2014-08-29 | 2015-01-28 | 浙江工业大学 | Synthesis method of biphenyl compounds |
| CN106674022A (en) * | 2015-11-10 | 2017-05-17 | 深圳超多维光电子有限公司 | Liquid crystal intermediate and preparation method of liquid crystal material |
| CN106966979A (en) * | 2017-04-22 | 2017-07-21 | 桂林理工大学 | The synthetic method of benzophenanthrene benzyloxy alkynes biphenyl alkynes benzene Qiao Lian perylene list imines dihexyls |
Non-Patent Citations (1)
| Title |
|---|
| 武汉大学化学与分子科学学院实验中心: "有机化学实验", vol. 2017, 武汉大学出版社, pages: 113 * |
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Application publication date: 20200327 |