CN1962580A - Method for preparing dicyclohexyl monomer liquid crystal by utilizing Grignard reaction - Google Patents
Method for preparing dicyclohexyl monomer liquid crystal by utilizing Grignard reaction Download PDFInfo
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- CN1962580A CN1962580A CN 200610070271 CN200610070271A CN1962580A CN 1962580 A CN1962580 A CN 1962580A CN 200610070271 CN200610070271 CN 200610070271 CN 200610070271 A CN200610070271 A CN 200610070271A CN 1962580 A CN1962580 A CN 1962580A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 32
- 239000000178 monomer Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000003747 Grignard reaction Methods 0.000 title claims abstract description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000009413 insulation Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000007818 Grignard reagent Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 150000004795 grignard reagents Chemical class 0.000 claims description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001263 acyl chlorides Chemical class 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 claims description 2
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 210000003608 fece Anatomy 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 238000009776 industrial production Methods 0.000 abstract description 3
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- -1 bicyclic hexane class Chemical class 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing a dicyclohexyl monomer liquid crystal, belonging to the technical field of preparation methods of monomer liquid crystals. A method for preparing a dicyclohexyl monomer liquid crystal by utilizing a Grignard reaction has a structural formula as follows: (FIG. I), wherein the synthetic route is (FIG. II) wherein R1，R2＝C2～C10，R3＝C1～C9The linear alkyl group of (1); x is Cl or Br or I; a ═ C2H4Or cyclohexane; n is 0 or 1. The preparation method has the characteristics of low requirement on production equipment, simple process, low production cost and environmental friendliness, so thatIs particularly suitable for the industrial production of 4, 4' -alkyl substituted bicyclohexane monomer liquid crystal.
Description
Technical field:
The present invention relates to a kind of method for preparing the dicyclic hexane monomer liquid crystal, especially a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal belongs to preparation method's technical field of monomer liquid crystal.
Background technology:
4,4 '-alkyl substituted bicyclic hexane class monomer liquid crystal generally all has the mesomorphic phase interval of broad, very low viscosity, and very high specific inductivity, and good consistency is arranged with other liquid crystal, be applied in STN widely, in the TFT dispensing liquid crystal.Synthetic method below Merck company discloses in patent DE19528085 and US4868341:
The defective of these two kinds of methods is inevitably to exist in the resulting product impurity of a large amount of hexanaphthene cis-configurations, greatly influenced the yield of product, caused high production cost, and wherein first method has been used expensive platinum catalyst, and carry out owing to be reflected under the high temperature, pressure, requirement to production unit is very high, and this also causes this method to be difficult to actual production.
Merck company discloses another synthetic method again in patent DE332173 subsequently:
Though this method has avoided generating too much hexanaphthene cis-configuration impurity, because long decline of product yield and raw materials cost and the production cost of also will causing of route rises.
The objective of the invention is to overcome the shortcoming that above-mentioned prior art exists, provide a kind of and can reduce raw materials cost and production cost, simplify the production unit requirement, satisfy 4 of industrial production needs, the preparation method of 4 '-alkyl substituted bicyclic hexane class monomer liquid crystal.
Purpose of the present invention can reach by following measure
Summary of the invention
A kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal, the structure representative formula of this dicyclic hexane monomer liquid crystal is
, R wherein
1=C
2～C
10Straight chained alkyl; R
2=C
2～C
10Straight chained alkyl; A=C
2H
4Perhaps cyclohexyl; N=0 or 1, its special character are that the preparation method of this dicyclic hexane monomer liquid crystal is for adopting
As the Grignard reagent prepared in reaction ketone of starting raw material and straight chain haloalkane, cherish by Wu Erfu-Kai again receive-Huang Min-lon reduction reaction makes the dicyclic hexane monomer liquid crystal.Synthetic route is as follows:
R wherein
1, R
2=C
2～C
10, R
3=C
1～C
9Straight chained alkyl; X is Cl or Br or I; A=C
2H
4, perhaps hexanaphthene; N=0 or 1;
The halides of grignard reaction is an alkyl chloride, bromoalkane, idoalkane, wherein preferred bromoalkane; The consumption of Grignard reagent is 100%～150% of an acyl chlorides mole number, wherein preferred 100-110%; The reaction solvent for use is an ether, THF, inertia ether solvents such as dioxane, wherein preferred THF; Temperature of reaction is-70～60 ℃, wherein preferred 20-30 ℃; Reaction times is 0.5～8 hour, wherein preferred 2-3 hour.
The present invention compared with prior art has following positively effect:
(1) avoided having reduced cost to a great extent because of in product, introducing the decline significantly of the product yield that a large amount of hexanaphthene cis-configuration isomer caused.
(2) reduced reactions steps, avoided with acyl chlorides be converted into acid amides dewater again the system nitrile process, shortened synthesis cycle, thereby reduced production cost.
(3) avoided using the above press device of 200 normal atmosphere of pressure-bearing, reduced the production unit requirement, on industrial production, possessed feasibility more.
Disclosed by the invention 4, the preparation method of 4 '-alkyl substituted bicyclic hexane class monomer liquid crystal is applicable to following monomer liquid crystal:
(anti-, anti-)-4-alkyl-4 '-alkyl-1,1 '-bis cyclohexane [structural formula:
R
1, R
2=C
2～C
10Straight chained alkyl]
1-(anti--the 4-alkyl-cyclohexyl)-2-(anti--4 '-alkyl-cyclohexyl) ethane [structural formula:
, R
1, R
2=C
2～C
10Straight chained alkyl]
(anti-, anti-, anti-)-4-alkyl-4 "-alkyl-[1,1 ', 4 ', 1 "] three hexanaphthenes [structural formula:
, R
1, R
2=C
2～C
10Straight chained alkyl]
Embodiment
Below provide the specific embodiment of the present invention, be used for that the invention will be further described, but the present invention is not limited to following embodiment.
Embodiment 1
(anti-, anti-)-4-ethyl-4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
] preparation
With 128g (0.5mol) (anti-, anti-)-4-(4 '-ethyl cyclohexyl) cyclohexyl formyl chloride, 400ml toluene is put in 2 liters of reaction flasks, the water-bath cooling, and temperature drips 0.5mol C for 20 ℃ in keeping
3H
7The 500ml THF solution of MgBr dropwises the back in 20 ℃ of insulations 2 hours, adds 700ml water and 20ml concentrated hydrochloric acid then, tells organic phase, washes 3 times to neutral, sloughs toluene, obtains the 133g white solid.Change in 2 liters of there-necked flasks, add the 640ml glycol ether, 98g potassium hydroxide, 125g hydrazine hydrate, be warming up to 130 ℃ of insulations 3 hours, heating up then is distilled to 200 ℃ of insulations 3 hours, cools to below 100 ℃, adds 400ml toluene and 700ml water, stirred 10 minutes, leave standstill phase-splitting, water extracts once with 150ml toluene, and organic phase is washed to neutrality with 600ml * 4, take off most solvent, make the solvent column chromatography with sherwood oil, obtain the 112g colourless liquid, the ethyl alcohol recrystallization of usefulness 1.5ml/g once, vacuum-drying, obtain 78g (anti-, anti-)-4-propyl group-4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
], mp:-3.4～3.0 ℃, cp:68.0～68.2 ℃, GC:99.9%.
Use similar preparation method, can obtain following monomer liquid crystal:
(anti-, anti-)-4-ethyl-4 '-amyl group-1,1 '-bis cyclohexane [structural formula:
], GC:99.9%, mp:16 ℃, cp:77 ℃.
Embodiment 2
(anti-, anti-)-4-propyl group-4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
] preparation
With 135g (0.5mol) (anti-, anti-)-4-(4 '-propyl group cyclohexyl) cyclohexyl formyl chloride, 400ml toluene is put in 2 liters of reaction flasks, the water-bath cooling, and temperature drips 0.5mol C for 20 ℃ in keeping
3H
7The 500ml THF solution of MgBr dropwises the back in 20 ℃ of insulations 2 hours, adds 700ml water and 20ml concentrated hydrochloric acid then, tell organic phase, wash 3 times, slough toluene to neutral, obtain the 140g white solid, change in 2 liters of there-necked flasks, add the 600ml glycol ether, 92g potassium hydroxide, the 125g hydrazine hydrate is warming up to 130 ℃ of insulations 3 hours, heat up then and be distilled to 200 ℃ of insulations 3 hours, cool to below 100 ℃, add 400ml toluene and 700ml water, stirred 10 minutes, leave standstill phase-splitting, water extracts once with 150ml toluene, and organic phase is washed to neutrality with 600ml * 4, takes off most solvent, make the solvent column chromatography with sherwood oil, obtain the 112g white solid, with the sherwood oil recrystallization of 0.5ml/g once, vacuum-drying, it is (anti-to obtain 87.5g, instead)-and the 4-propyl group, 4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
], mp:63.8～64.3 ℃, cp:81.6～81.8 ℃.GC：99.9％。
Use similar preparation method, can obtain following monomer liquid crystal
(anti-, anti-)-4-propyl group-4 '-butyl-1,1 '-bis cyclohexane [structural formula:
] GC:99.9%, mp:-8 ℃, cp:94 ℃.
(anti-, anti-)-4-propyl group-4 '-amyl group-1,1 '-bis cyclohexane [structural formula:
] GC:99.9%, mp:22 ℃, cp:56 ℃.
Embodiment 3
Operation is adopted anti--4-(2-(anti--4 '-ethyl cyclohexyl) ethyl) cyclohexyl formyl chloride and C with embodiment 2
4H
9MgBr be raw material can make 1-(anti--4-ethyl cyclohexyl)-2-(anti--4 '-amyl group cyclohexyl) ethane [structural formula:
].GC：99.9％，mp：2.5℃，cp：76℃。
Embodiment 4
Operation is with embodiment 2, adopts anti--4-(4 '-(4 "-butyl cyclohexyl) cyclohexyl) cyclohexyl formyl chloride and C
3H
7MgBr is that raw material can make (anti-, anti-, anti-)-4,4 "-dibutyl-[1,1 ', 4 ', 1 "] three hexanaphthenes [structural formula:
].GC：99.9％，mp：104℃，cp：265℃。
Claims (9)
1, a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal, the structure representative formula of this dicyclic hexane monomer liquid crystal is
R wherein
1=C
2～C
10Straight chained alkyl; R
2=C
2～C
10Straight chained alkyl; A=C
2H
4Perhaps cyclohexyl; N=0 or 1 is characterized in that the preparation method is employing
As the Grignard reagent prepared in reaction ketone of starting raw material and straight chain haloalkane, cherish by Wu Erfu-Kai again receive-Huang Min-lon reduction reaction makes the dicyclic hexane monomer liquid crystal,
Synthetic route is
R wherein
1, R
2=C
2～C
10, R
3=C
1～C
9Straight chained alkyl; X is Cl or Br or I; A=C
2H
4, perhaps hexanaphthene; N=0 or 1.
2, by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of claim 1, the halides that it is characterized in that being used for grignard reaction is alkyl chloride or bromoalkane or idoalkane.
3, by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of claim 1, the consumption of Grignard reagent is 100%～150% of an acyl chlorides mole number in it is characterized in that reacting.
4, by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of claim 3, the consumption of Grignard reagent is the 100-110% of acyl chlorides mole number in it is characterized in that reacting.
5, by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of claim 1, it is characterized in that reacting solvent for use is ether or THF or dioxane inertia ether solvent.
6,, it is characterized in that temperature of reaction is-70～60 ℃ by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of claim 1; Reaction times is 0.5～8 hour.
7,, it is characterized in that temperature of reaction is 20～30 ℃ by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of claim 6; Reaction times is 2～3 hours.
8, by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of arbitrary claim among the claim 1-6, it is characterized in that (anti-, anti-)-4-ethyl-4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
Preparation
Will (anti-, instead)-4-(4 '-ethyl cyclohexyl) cyclohexyl formyl chloride, toluene is put in the reaction flask, water-bath cooling, 20 ℃ of droppings of temperature C in keeping
3H
7The THF solution of MgBr dropwises the back in 20 ℃ of insulations 2 hours, adds entry and concentrated hydrochloric acid then, tells organic phase, washes 3 times to neutral, sloughs toluene, obtains white solid;
Change in the bottle, add glycol ether, potassium hydroxide, hydrazine hydrate, be warming up to 130 ℃ of insulations 3 hours, heating up then is distilled to 200 ℃ of insulations 3 hours, cools to below 100 ℃, adds toluene and water, stirred 10 minutes, and left standstill phase-splitting, water with the toluene extraction once, organic phase washes with water to neutrality, takes off most solvent, makes the solvent column chromatography with sherwood oil, obtain colourless liquid, with ethyl alcohol recrystallization once, vacuum-drying, obtain (anti-, anti-)-4-ethyl-4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
9, by the described a kind of method of utilizing grignard reaction to prepare the dicyclic hexane monomer liquid crystal of arbitrary claim among the claim 1-6, it is characterized in that (anti-, anti-)-4-propyl group-4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
Preparation
Will (anti-, instead)-4-(4 '-propyl group cyclohexyl) cyclohexyl formyl chloride, toluene is put in the reaction flask, water-bath cooling, 20 ℃ of droppings of temperature C in keeping
3H
7The THF solution of MgBr dropwises the back in 20 ℃ of insulations 2 hours, adds entry and concentrated hydrochloric acid then, tell organic phase, wash 3 times, slough toluene to neutral, obtain white solid, change in the there-necked flask, add glycol ether, potassium hydroxide, hydrazine hydrate is warming up to 130 ℃ of insulations 3 hours, heat up then and be distilled to 200 ℃ of insulations 3 hours, cool to below 100 ℃, add toluene and water, stirred 10 minutes, leave standstill phase-splitting, water extracts once with toluene, and organic phase washes with water to neutrality, takes off most solvent, make the solvent column chromatography with sherwood oil, obtain white solid, with the sherwood oil recrystallization once, vacuum-drying, obtain (anti-, instead)-and the 4-propyl group, 4 '-propyl group-1,1 '-bis cyclohexane [structural formula:
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610070271 CN1962580A (en) | 2006-11-20 | 2006-11-20 | Method for preparing dicyclohexyl monomer liquid crystal by utilizing Grignard reaction |
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|---|---|---|---|
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ID=38081831
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060641A (en) * | 2009-11-13 | 2011-05-18 | Dic株式会社 | Preparing method of compound with trans-1,4-cyclohexylidene structure |
| CN102101815A (en) * | 2009-12-17 | 2011-06-22 | 默克专利股份有限公司 | Isomerization method |
| CN102101813A (en) * | 2009-12-17 | 2011-06-22 | 默克专利股份有限公司 | Isomerization method |
| CN101580714B (en) * | 2009-06-19 | 2011-11-30 | 江苏广域化学有限公司 | Preparation method of dicyclic hexane liquid crystal monomer |
| EP2532638A1 (en) | 2011-06-07 | 2012-12-12 | Merck Patent GmbH | Isomerisation method |
| EP2532637A1 (en) | 2011-06-07 | 2012-12-12 | Merck Patent GmbH | Isomerisation method |
| CN104447171A (en) * | 2014-12-24 | 2015-03-25 | 威海德润显示材料有限公司 | Preparation method of bicyclohexyl bialkyl liquid crystal compound |
| CN111233605A (en) * | 2020-01-19 | 2020-06-05 | 西安瑞联新材料股份有限公司 | Synthesis method of (trans ) -4-alkyl-4 '-alkyl-1, 1' -bicyclohexane |
| CN113024335A (en) * | 2021-03-12 | 2021-06-25 | 烟台盛华液晶材料有限公司 | Synthesis method of trans, trans-4-alkyl-4' -pentyl-3 (E) -alkene-bicyclohexane liquid crystal monomer |
| CN113880680A (en) * | 2021-11-10 | 2022-01-04 | 湖南经世新材料有限责任公司 | Synthesis method of trans, trans-4, 4' -disubstituted bicyclohexane compound |
| CN114349586A (en) * | 2021-12-29 | 2022-04-15 | 阜阳欣奕华材料科技有限公司 | Preparation method of trans-alkyl bicyclohexyl liquid crystal monomer |
-
2006
- 2006-11-20 CN CN 200610070271 patent/CN1962580A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101580714B (en) * | 2009-06-19 | 2011-11-30 | 江苏广域化学有限公司 | Preparation method of dicyclic hexane liquid crystal monomer |
| CN102060641A (en) * | 2009-11-13 | 2011-05-18 | Dic株式会社 | Preparing method of compound with trans-1,4-cyclohexylidene structure |
| CN102060641B (en) * | 2009-11-13 | 2014-11-05 | Dic株式会社 | Preparing method of compound with trans-1,4-cyclohexylidene structure |
| CN102101815B (en) * | 2009-12-17 | 2015-05-27 | 默克专利股份有限公司 | Isomerization method |
| CN102101815A (en) * | 2009-12-17 | 2011-06-22 | 默克专利股份有限公司 | Isomerization method |
| CN102101813A (en) * | 2009-12-17 | 2011-06-22 | 默克专利股份有限公司 | Isomerization method |
| CN102101813B (en) * | 2009-12-17 | 2015-10-14 | 默克专利股份有限公司 | Isomerization method |
| EP2532638A1 (en) | 2011-06-07 | 2012-12-12 | Merck Patent GmbH | Isomerisation method |
| EP2532637A1 (en) | 2011-06-07 | 2012-12-12 | Merck Patent GmbH | Isomerisation method |
| CN104447171A (en) * | 2014-12-24 | 2015-03-25 | 威海德润显示材料有限公司 | Preparation method of bicyclohexyl bialkyl liquid crystal compound |
| CN111233605A (en) * | 2020-01-19 | 2020-06-05 | 西安瑞联新材料股份有限公司 | Synthesis method of (trans ) -4-alkyl-4 '-alkyl-1, 1' -bicyclohexane |
| CN111233605B (en) * | 2020-01-19 | 2023-02-10 | 西安瑞联新材料股份有限公司 | Synthesis method of (trans ) -4-alkyl-4 '-alkyl-1, 1' -bicyclohexane |
| CN113024335A (en) * | 2021-03-12 | 2021-06-25 | 烟台盛华液晶材料有限公司 | Synthesis method of trans, trans-4-alkyl-4' -pentyl-3 (E) -alkene-bicyclohexane liquid crystal monomer |
| CN113024335B (en) * | 2021-03-12 | 2024-04-23 | 烟台盛华液晶材料有限公司 | Synthesis method of trans, trans-4-alkyl-4' -amyl-3 (E) -alkene-bicyclohexane liquid crystal monomer |
| CN113880680A (en) * | 2021-11-10 | 2022-01-04 | 湖南经世新材料有限责任公司 | Synthesis method of trans, trans-4, 4' -disubstituted bicyclohexane compound |
| CN113880680B (en) * | 2021-11-10 | 2024-08-20 | 湖南经世新材料有限责任公司 | Synthesis method of trans, trans-4, 4' -disubstituted dicyclohexyl compound |
| CN114349586A (en) * | 2021-12-29 | 2022-04-15 | 阜阳欣奕华材料科技有限公司 | Preparation method of trans-alkyl bicyclohexyl liquid crystal monomer |
| CN114349586B (en) * | 2021-12-29 | 2023-10-20 | 阜阳欣奕华材料科技有限公司 | Preparation method of trans-alkyl bicyclohexane liquid crystal monomer |
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