CN108277019A - A kind of preparation method of trans cvclohexvl base class liquid-crystal compounds - Google Patents
A kind of preparation method of trans cvclohexvl base class liquid-crystal compounds Download PDFInfo
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- CN108277019A CN108277019A CN201711125767.7A CN201711125767A CN108277019A CN 108277019 A CN108277019 A CN 108277019A CN 201711125767 A CN201711125767 A CN 201711125767A CN 108277019 A CN108277019 A CN 108277019A
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- 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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- 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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C09K19/00—Liquid crystal materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-Ph
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Abstract
The invention discloses one kind having general formula
Description
Technical field
The present invention relates to liquid crystal materials, and in particular to a kind of preparation method of trans cvclohexvl base class liquid-crystal compounds.
Background technology
Liquid crystal material is partial order, anisotropic liquid, between three-dimensional order solid and isotropic liquid.
G.Friedel and F.Grand-jean of France etc. have done detailed research to the structure and optical property of liquid crystal, and in 1922
Year completes the work of liquid crystal classification, and liquid crystal is divided into：Smectic phase, nematic phase and cholesteric phase.G.H.Heilmeir is made
First liquid crystal display (LCD) in the world.T.L.Fergason in 1971 etc. proposes twisted nematic (Twisted
Nematic：TN) pattern, W.Helfrich and M.Schadt utilize the electrooptic effect and integrated circuit phase of twisted nematic liquid crystal
In conjunction with being made into display device, realized the industrialization of liquid crystal material, be still the liquid crystal of most mainstream in the market at present
Show device pattern.
As liquid crystal display is widely applied, the requirement to its performance is also constantly improving, in terms of high image quality
It is required that wider array of operating temperature, faster response speed and higher contrast, and require power consumption lower and lower, it means that more
Low driving voltage, higher light transmittance.
Currently, the trans cvclohexvl base class liquid-crystal compounds with general formula I is with preferable performance：
The trans cvclohexvl base class liquid-crystal compounds is mainly used from the cis-compound of the general formula structure and trans-ization
The method for closing Crystallization Separation in the mixture of object obtains, since the trans- dicyclohexyl class of this in cis-trans-isomer mixture liquid-crystalizes
It closes object content and there was only 50% or so, therefore, the transreflective liquid crystal compound synthesis yield with general formula I is low.
Invention content
The purpose of the present invention is to provide a kind of systems for the trans cvclohexvl base class liquid-crystal compounds that can greatly improve yield
Preparation Method solves the problems, such as that trans cvclohexvl base class liquid-crystal compounds yield is low.
Technical solution：The present invention provides a kind of preparation method of trans cvclohexvl base class liquid-crystal compounds, the trans-cycloh
Class liquid-crystal compounds has general formula I：
In general formula I, R and R ' are each independently the straight chained alkyl with 1~9 carbon atom；M is 0 or 1, and n is 0 or 1,
And m, n cannot be 0 simultaneously；
The preparation method of the trans cvclohexvl base class liquid-crystal compounds includes：Using trifluoromethanesulfonic acid as transition reagent, make tool
Have general formula I cis-trans-isomer mixture (by with general formula I trans cvclohexvl base class liquid-crystal compounds and with the suitable of general formula I
Formula hexamethylene base class compound is constituted) transition, the trans cvclohexvl base class liquid-crystal compounds with general formula I is made.
Advantageous effect：The present invention trans cvclohexvl base class liquid-crystal compounds preparation method, using trifluoromethanesulfonic acid as
Make the transition reagent, can greatly improve the transition yield of the liquid-crystal compounds of base class containing trans cvclohexvl so that trans- in product：Cis ratio
95: 5 or more, efficiently solve the problems, such as that the transition yield containing the transreflective liquid crystal compound of alkoxy and cyclohexyl structure is low.
Specific implementation mode
It should be noted that in the absence of conflict, the features in the embodiments and the embodiments of the present application can phase
Mutually combination.Below in conjunction with embodiment, the present invention will be described in detail.
In a kind of typical embodiment of the present invention, a kind of preparation side of trans cvclohexvl base class liquid-crystal compounds is provided
Method, the trans cvclohexvl base class liquid-crystal compounds are with general formula I, general formula I：
In general formula I, R and R ' are each independently the straight chained alkyl with 1~9 carbon atom；M is 0 or 1, and n is 0 or 1,
And when m, n difference be 0；
The preparation method of the trans cvclohexvl base class liquid-crystal compounds includes, using trifluoromethanesulfonic acid as transition reagent, making tool
There is the cis-compound of general formula I to make the transition, the transreflective liquid crystal compound with general formula I is made.
The preparation method uses trifluoromethanesulfonic acid substance as transition reagent, makes the transition to cis-trans-isomer mixture
When, the yield of the transreflective liquid crystal compound containing alkoxy and cyclohexyl structure can be greatly improved.
Preferably, the cis-compound with general formula I is the cis- chemical combination in the cis-trans-isomer mixture with general formula I
Object can directly obtain the higher trans cvclohexvl base class of purity using the cis-trans-isomer mixture with general formula I as raw material in this way
Liquid-crystal compounds, it is convenient that raw material obtains, to make the manufacturing cost of trans cvclohexvl base class liquid-crystal compounds reduce.
Preferably, the specific method of above-mentioned transition is：Cis-trans-isomer mixture with general formula I is dissolved in dichloromethane
Or in dichloroethanes, under inert gas shielding, after -25~-30 DEG C are stirred 1~3h with trifluoromethanesulfonic acid, sealing and standing mistake
Night (time is 10~15h)；The ratio between amount of substance of cis-trans-isomer mixture and trifluoromethanesulfonic acid with general formula I is 1:
0.8~1.5.
Above-mentioned transition condition can make the transition yield that there is the cis-compound of general formula I to be transformed into trans-compound into one
Step improves.
Preferably, obtained product is purified after the step that makes the transition, it is higher with general formula I that purity can be obtained in this way
The transreflective liquid crystal compound of structure.
It is further preferred that above-mentioned purification process is：The mixed solvent of n-hexane and water is added into transition product, stands
Layering, it is neutrality to detach organic phase and organic phase is washed to pH, is concentrated, dry, recrystallization.In the mixed solvent, n-hexane and
The volume ratio of water is 1: 5~10.
The transreflective liquid crystal compound with general formula I that purity is further enhanced can be obtained in above-mentioned purification process.
The above-mentioned cis-trans-isomer mixture with general formula I may be used any means known in the art and prepare.It is preferred that
The preparation method on ground, the cis-trans-isomer mixture with general formula I of the invention includes the following steps：
1) makeIt reacts, prepares with magnesium metal
2) make step 1) obtainedWithGrignard reaction is carried out, is prepared
3) obtained to step 2)It is dehydrated, adds hydrogen, trans cvclohexvl base class is made
Liquid-crystal compounds；
In step 1)~step 3), R and R ' are each independently the straight chained alkyl with 1~9 carbon atom；M is 0 or 1,
N is 0 or 1, and is 0 when m, n difference.
Since what the preparation method obtained has general formulaCis-trans-isomer mixture
Yield it is higher, can further improve the ultimate yield of target product trans cvclohexvl base class liquid-crystal compounds of the present invention.
Above-mentioned steps 1)~3) involved in each step, may be selected to carry out using condition known in the art and method real
It is existing.
The synthetic route of the liquid-crystal compounds of the present invention is as follows：
Preferably,
Above-mentioned steps 1) in, it,, will under inert atmosphere protection using iodine as initiator using ether solvent as reaction dissolventSolution is added in magnesium metal, in 40~50 DEG C of 1~2h of back flow reaction, is prepared
Molar ratio with magnesium metal is 1: 0.95~1.25, preferably 1: 1.05~1.1；Ether solvent is anhydrous ether or tetrahydrochysene furan
It mutters；Back flow reaction temperature is preferably 45 DEG C.
Above-mentioned steps 2) in, it, will at 25~30 DEG C under inert atmosphere protectionAnhydrous ether
Solution is added toIn, 1~2h is reacted at 40~50 DEG C, is prepared WithMolar ratio be 1: 1.0~1.5, preferably 1: 1.1~1.2.
Above-mentioned steps 3) in, dehydration be using toluene as solvent,, will under inert atmosphere protection using acidic dehydration agentRefluxing toluene is carried out at 100~110 DEG C divides water 1~2h, is made
It is, with Pd/C or Raney's nickel (Raney Ni) for catalyst, dehydration to be made using toluene, ethyl alcohol or tetrahydrofuran as solvent to add hydrogen
Under the conditions of temperature is 20~50 DEG C and pressure is 0.5~5Mpa reaction 8~
The cis-trans-isomer mixture with general formula I is made in 20h.
Acidic dehydration agent is phosphorus pentoxide, potassium acid sulfate or p-methyl benzenesulfonic acid；Add in hydrogen with the mixed of toluene and ethyl alcohol
Solution is closed as solvent, using 5%Pd/C as catalyst, pressure is 0.5~1.5Mpa.
Above-mentioned reaction condition can further increase the trans cvclohexvl base class liquid-crystal compounds with general formula I of the present invention
Yield and purity, it is trans- in product before purification：Cis ratio is finally obtained anti-with general formula I after purification 95: 5 or more
The purity of formula hexamethylene base class liquid-crystal compounds is 99.95% or more.
Below with reference to embodiment and comparative example, the advantageous effect that further illustrates the present invention.
Embodiment 1
- 4 '-propyl -1 of trans- 4- (4- methoxyphenyls), 1 '-bis- (hexamethylenes)
Preparation method be：
The preparation of step 1, grignard reagent
500ml four-hole bottles are taken, thermometer, mechanical agitation, constant pressure funnel are installed, leads to nitrogen, is added into system
7.2g magnesium chips, a small amount of anhydrous ether, 1~2 iodine heat initiation reaction, the color fade of iodine are waited for, after initiation, into reaction system
The mixed solution of 51.5g para-bromoanisole and 150ml anhydrous ethers is added dropwise, 55 DEG C of temperature control is finished hereinafter, dripping, and about 1 is kept the temperature at 45 DEG C
~1.5h, heat preservation are finished, cooling for use.
Step 2, grignard reaction and dehydration
The preparation of step 1 grignard reagent finishes, and reaction system is cooled to 10 DEG C or so, 55.6g is added dropwise into reaction system
The mixed solution of propyl dicyclohexyl ketone and 500ml anhydrous ethers, 25~30 DEG C of temperature control.Drop finishes, and after 45 DEG C are stirred to react 2h, adds
10% dilute hydrochloric acid hydrolyzes, stratification, and organic phase is washed to neutrality, after desolventizing, after adding 300ml toluene to dissolve, goes back to reaction
Bottle, is added 3g p-methyl benzenesulfonic acids, and agitating and heating stops reaction after reacting 1~2h at 100~110 DEG C, after cooling, adds water
Stratification, washing organic phase to neutrality concentrate desolventizing after anhydrous magnesium sulfate drying.
Step 3, hydrogenation reaction
Product made from step 2 is dissolved in 200ml toluene and 100ml ethyl alcohol, with 3g 5%Pd/C, at 45 DEG C,
Under 1Mpa plus hydrogen is to no pressure drop, and gained reaction solution, which is crossed, filters out Pd/C, removes solvent, and basic suitable inverse proportion is 45: 55 in product.
Step 4, isomerization
500ml four-hole bottles, install thermometer, mechanical agitation, and the low liquid funnel of constant pressure leads to nitrogen, is added into system
The dichloromethane of product and 250ml made from 25.12g steps 3, is cooled to -25~-30 DEG C, and 18g fluoroforms are added dropwise into system
Sulfonic acid, temperature control -25~-30 DEG C, drop finishes, quiet overnight after stir about 1h, reaches 5: 95 along inverse ratio, adds n-hexane and water, stands and divide
Layer, organic phase are washed to neutrality, concentrate and take off dry solvent, are recrystallized with n-hexane, obtain the trans- fine work of 99.95% or more 16g
(white crystal).
It is analyzed using GC-MS obtaining product, the m/z of product is 314.2.The performance parameter of liquid-crystal compounds：TNI-
ext：223 DEG C, TCN=80 DEG C, △ n-ext：0.1155.Wherein, TNIIndicate clearing point, TCNIndicate fusing point；△ n indicate that optics is each
Anisotropy (△ n=ne-no, 589nm, 25 DEG C of measuring temperature)；And using dsc measurement TNI、TCN；△ is measured using abbe refractometers
n。
Embodiment 2
Trans- 1- methoxyl groups -4- (4- (3- propyl cyclopenta) cyclohexyl) benzene
Preparation
The preparation of step 1, grignard reagent
500ml four-hole bottles are taken, thermometer, mechanical agitation, constant pressure funnel are installed, leads to nitrogen, is added into system
7.2g magnesium chips, a small amount of anhydrous ether heat initiation reaction with 1~2 iodine, the color fade of iodine are waited for, after initiation, to reaction system
The middle mixed solution that 51.5g para-bromoanisole and 150ml anhydrous ethers is added dropwise, 55 DEG C of temperature control are finished hereinafter, dripping, are kept the temperature about at 45 DEG C
1~1.5h, heat preservation are finished, cooling for use.
Step 2, grignard reaction and dehydration
The preparation of step 1 grignard reagent finishes, and reaction system is cooled to 10 DEG C or so, 55.6g is added dropwise into reaction system
The mixed solution of 4- (3- propyl cyclopenta) cyclohexanone and 500ml anhydrous ethers, 25~30 DEG C of temperature control.Drop finishes, and 45 DEG C of stirrings are anti-
After answering 2h, 10% dilute hydrochloric acid is added to hydrolyze, stratification, organic phase is washed to neutrality, after desolventizing, after adding 300ml toluene to dissolve,
Reaction bulb is gone back to, 3g p-methyl benzenesulfonic acids are added, agitating and heating stops reaction, cooling after reacting 1~2h at 100~110 DEG C
Afterwards, water stratification, washing organic phase to neutrality is added to concentrate desolventizing after anhydrous magnesium sulfate drying.
Step 3, hydrogenation reaction
Product made from step 2 is dissolved in 200ml toluene and 100ml ethyl alcohol, with 3g 5%Pd/C, at 45 DEG C,
Under 1Mpa plus hydrogen is to no pressure drop, and gained reaction solution, which is crossed, filters out Pd/C, removes solvent, and basic suitable inverse proportion is 45 in obtained product:
55。
Step 4, isomerization
500ml four-hole bottles, install thermometer, mechanical agitation, and the low liquid funnel of constant pressure leads to nitrogen, 24g is added into system
The dichloromethane of product made from step 3 and 250ml is cooled to -25~-30 DEG C, and 18g trifluoromethanesulfonic acids are added dropwise into system,
Temperature control -25~-30 DEG C, drop finish, and after stir about 3h overnight, reach 5: 95 along inverse ratio, add n-hexane and water, stratification organic
It is mutually washed to neutrality, concentrates and takes off dry solvent, recrystallized with n-hexane, obtain the trans- fine work of 99.95% or more 15g.
It is analyzed using GC-MS obtaining product, the m/z of product is 300.2.The performance parameter of liquid-crystal compounds：TNI-
ext：73 DEG C, TCN=56 DEG C, △ n-ext：0.1057.Wherein, TNIIndicate clearing point, TCNIndicate fusing point；△ n indicate that optics is each
Anisotropy (△ n=ne-no, 589nm, 25 DEG C of measuring temperature)；And using dsc measurement TNI、TCN；△ is measured using abbe refractometers
n。
With reference to utilization embodiment 1,2 similar preparation methods, it may be convenient to prepare following negative dielectric anisotropy liquid crystal
Compound：
In addition to this, though the preparation method of the claimed transreflective liquid crystal compound of the non-limit of the embodiment of the present invention,
Those skilled in the art will envision that on the basis of published above-described embodiment, the professional knowledge only in conjunction with itself is
Other similar compounds can be obtained without making the creative labor.Representative embodiment is only enumerated herein.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, any made by repair
Change, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of trans cvclohexvl base class liquid-crystal compounds, which has general formula I,
The general formula I is：
In general formula I, R and R ' are each independently the straight chained alkyl with 1~9 carbon atom；M is 0 or 1, and n is 0 or 1, and m, n
It is asynchronously 0；
It is characterized in that, the preparation method of the trans cvclohexvl base class liquid-crystal compounds includes, using trifluoromethanesulfonic acid as transition
Reagent makes to have the cis-compound of general formula I to make the transition, the trans cvclohexvl base class liquid-crystal compounds is made.
2. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 1, which is characterized in that described to have
The cis-compound of general formula I is the cis-compound in the cis-trans-isomer mixture with general formula I.
3. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 2, which is characterized in that the transition
Method be：Cis-trans-isomer mixture with general formula I is dissolved in dichloromethane or dichloroethanes, inert gas shielding
Under, stand 10~15h after being mixed and stirred for 1~3h with trifluoromethanesulfonic acid at -25~-30 DEG C；The suitable anteiso- with general formula I
The molar ratio of structure body mixture and trifluoromethanesulfonic acid is 1: 0.8~1.5.
4. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 2, which is characterized in that described trans-
The preparation method of hexamethylene base class liquid-crystal compounds further includes the steps that being purified to transition product.
5. the preparation method of the transreflective liquid crystal compound according to claim 4 containing alkoxy and cyclohexyl structure, special
Sign is that the purifying includes：The mixed solvent of n-hexane and water is added into transition product, stratification detaches organic phase
And organic phase is washed, concentrated, dried and is recrystallized to get the trans cvclohexvl base class liquid-crystal compounds.
6. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 2, which is characterized in that described to have
The preparation method of the cis-trans-isomer mixture of general formula I includes the following steps：
1) makeIt reacts, prepares with magnesium metal
2) make step 1) obtainedWithGrignard reaction is carried out, is prepared
3) obtained to step 2)It is dehydrated, adds hydrogen, the trans- ring is made
Hexyl class liquid-crystal compounds；
In step 1)~step 3), R and R ' are each independently the straight chained alkyl with 1~9 carbon atom；M is 0 or 1, n 0
Or 1, and be 0 when m, n difference.
7. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 6, which is characterized in that step 1)
In, it,, will under inert atmosphere protection using iodine as initiator using ether solvent as reaction dissolventSolution is added
Into magnesium metal, in 40~50 DEG C of 1~2h of back flow reaction, prepareIt is describedWith the metal
The molar ratio of magnesium is 1: 0.95~1.25, preferably 1: 1.05~1.1；The ether solvent is anhydrous ether or tetrahydrofuran.
8. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 6, which is characterized in that step 2)
In, it, will at 25~30 DEG C under inert atmosphere protectionAnhydrous ether solution be added to
In, then 40~50 DEG C of 1~2h of reaction are added dilute acid hydrolysis, prepareIt is describedWith it is describedMolar ratio be 1: 1.0~1.5, preferably 1: 1.1~1.2.
9. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 6, which is characterized in that described in step 3)
Dehydration, using acidic dehydration agent, under inert atmosphere protection, is incited somebody to action using toluene as solvent
Refluxing toluene is carried out at 100~110 DEG C divides water 1~2h, is madeIt is described to add
Hydrogen, using Pd/C or RaneyNi as catalyst, is incited somebody to action using toluene, ethyl alcohol or tetrahydrofuran as solventUnder the conditions of temperature is 20~50 DEG C and pressure is 0.5~5Mpa reaction 8~
The cis-trans-isomer mixture with general formula I is made in 20h.
10. the preparation method of trans cvclohexvl base class liquid-crystal compounds according to claim 9, which is characterized in that the acid
Property dehydrating agent be phosphorus pentoxide, potassium acid sulfate or p-methyl benzenesulfonic acid；Described plus hydrogen is made with the mixed solution of toluene and ethyl alcohol
For solvent, using Pd/C as catalyst, pressure is 0.5~1.5Mpa.
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| CN108913158A (en) * | 2018-08-23 | 2018-11-30 | 京东方科技集团股份有限公司 | Liquid-crystal composition and preparation method thereof, display panel and display device |
| CN110964538A (en) * | 2019-12-18 | 2020-04-07 | 江苏创拓新材料有限公司 | Transposition method of 1-cyclohexyl-2, 3-difluorobenzene |
| CN110964538B (en) * | 2019-12-18 | 2022-01-04 | 江苏创拓新材料有限公司 | Transposition method of 1-cyclohexyl-2, 3-difluorobenzene |
| CN114890857A (en) * | 2022-06-21 | 2022-08-12 | 中节能万润股份有限公司 | Method for preparing cycloalkane from cyclic alcohol in one step through molecular sieve |
| CN114890857B (en) * | 2022-06-21 | 2023-04-07 | 中节能万润股份有限公司 | Method for preparing cycloalkane from cyclic alcohol in one step through molecular sieve |
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Application publication date: 20180713 |