CN1308271C - Preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene - Google Patents
Preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene Download PDFInfo
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- CN1308271C CN1308271C CNB2006100383042A CN200610038304A CN1308271C CN 1308271 C CN1308271 C CN 1308271C CN B2006100383042 A CNB2006100383042 A CN B2006100383042A CN 200610038304 A CN200610038304 A CN 200610038304A CN 1308271 C CN1308271 C CN 1308271C
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Abstract
The present invention relates to a preparation method of 4-propyl cyclohexyl benzene of liquid crystal chemicals. The utility model is characterized in that provides cheap p-hydroxypropiophenone as raw material to replace the 4-propyl cyclohexyl phenol; high-pressure hydrogenation synthesizes 4-propyl cyclohexanone in a first step; then, 4-propyl cyclohexanone is reused as the raw material for forming the 4-propyl cyclohexyl benzene by a grignard reaction and dehydration; the 4-propyl cyclohexyl benzene is formed by low pressure hydrogenation and reduction. The technical indexes of the 4-propyl cyclohexyl benzene of a final product achieve prospective goals; the purity is larger than and is equal to 99.5%; the external appearance is changed into slight yellow from no color. The technology raises the contents and the external appearance of the current products, and the cost is saved.
Description
Technical field
The present invention relates to the technology of preparing of a kind of technology of preparing of liquid crystal chemical, particularly liquid crystal chemicals 4-propyl cyclohexyl benzene.
Background technology
China's liquid crystal material production is through the effort of recent two decades, progressively formed the industry of considerable scale, be converted into section port by complete import, but share shared in liquid crystal material market, the world is very little, still do not satisfy the needs of world LCD development, up to the present liquid crystal display device and liquid crystal material research and development are still based on TN type and low and middle-grade HTN type, and serve as that main medium-to-high grade liquid crystal material (TFT) research and development of producing is made slow progress with the 4-propyl cyclohexyl, with Japan, Germany and Great Britain and America country ratio, at least fell behind about 10 years to 15 years, make China in world's liquid-crystal display industry market, lack competitiveness.
Need earlier synthetic 4-propyl group pimelinketone as intermediate reaction product among the preparation method of 4-propyl cyclohexyl.And domesticly existing 4-propyl group pimelinketone synthetic method is adopted two-step approach usually, promptly 4-propyl group hexamethylene phenol hydrogenation in the presence of catalyzer such as Raney nickel generates 4-propyl group hexalin, reoxidizes to generate 4-propyl group pimelinketone.Yet its raw material of method 4-propyl group hexamethylene phenol price of this synthetic 4-propyl group pimelinketone is higher relatively, and reaction can not a step obtain 4-propyl group pimelinketone, the also relative reduction with content of the yield of 4-propyl group pimelinketone.
Summary of the invention
The preparation method's of the existing 4-propyl cyclohexyl of technical problem to be solved by this invention starting raw material cost is higher, the content and the also not high problem of yield of technology relative complex, product.
For solving the problems of the technologies described above, it is that starting raw material replaces 4-propyl group hexamethylene phenol that the present invention adopts cheap ethyl-para-hydroxyphenyl ketone, one-step synthesis goes out yield and all higher 4-propyl group pimelinketone of content, and then be raw material through grignard reaction with 4-propyl group pimelinketone, dehydration generates 4-propyl group tetrahydrobenzene benzene, generates the 4-propyl cyclohexyl through the low-voltage hydrogenation reduction again.
The present invention includes following steps:
1) the synthetic 4-propyl group pimelinketone of ethyl-para-hydroxyphenyl ketone high-pressure hydrogenation
Virahol and ethyl-para-hydroxyphenyl ketone are pressed 1: 1-4: 1 mol ratio drops in the reactor, add palladium/carbon catalyst simultaneously, the weight ratio 10 of ethyl-para-hydroxyphenyl ketone and palladium/carbon catalyst: 1-30: 1, under oxygen free condition, feed hydrogen to 0.3-0.8MPa, be warming up to 50-90 ℃, react and stop the back to hydrogenation and improve temperature to 140～180 ℃, hydrogen pressure is increased to 1.3-2.5MPa, continue hydrogenation with this understanding, be not cooled to 20-40 ℃ after do not inhale hydrogen, slowly release pressure after, with nitrogen material in the still is extruded, distillation gets crude product to the propyl group pimelinketone after reclaiming Virahol, gets elaboration 4-propyl group pimelinketone through underpressure distillation again, and content is more than 99.5%;
2) grignard reaction
In reactor, add THF (tetrahydrofuran (THF)) and magnesium powder, add iodine after being warming up to 40-60 ℃, after the initiation bromobenzene is at the uniform velocity splashed into reactor, drip off the back 40-60 ℃ of reaction 3-6 hour, under 45-65 ℃ of condition, splash into the 4-propyl group pimelinketone that step 1 makes, drip and keep reaction after 2-5 hour, the hydrochloric acid soln hydrolysis of adding 10%, after hydrolysis is intact that material is static, normal pressure is sloughed THF behind the branch water-yielding stratum, obtains 4-propyl group-1-phenyl hexamethylene-1-alcohol; Wherein, the mol ratio of THF and 4-propyl group pimelinketone is 4.5: 1-4.1: 1, and the mol ratio of magnesium powder and 4-propyl group pimelinketone is 1.04: 1-1.34: 1, the mol ratio of bromobenzene and 4-propyl group pimelinketone is 1.1: 1-1.2: 1;
3) dehydration reaction
Add toluene and PTS (p-methyl benzenesulfonic acid) catalyzer, react and distill recovery toluene after 2-3 hour and get crude product, get elaboration 4-propyl group tetrahydrobenzene benzene through underpressure distillation again, content is more than 99%; Wherein, the mol ratio of catalyzer toluene and 4-propyl group pimelinketone is 4: 1-2: 1, and the mol ratio of PTS and 4-propyl group pimelinketone is 0.0232: 1-0.0696: 1;
4) with 4-propyl group tetrahydrobenzene benzene, Virahol in molar ratio 3: 1-6: 1 drops in the autoclave, adds skeletal nickel catalyst, and the weight ratio of skeleton nickel and 4-propyl group tetrahydrobenzene benzene is 0.05: 1-0.2: 1, sealing autoclave behind nitrogen replacement, feeds hydrogen, be warming up to 50-60 ℃, the beginning hydrogenation fed hydrogen after 2-3 hour, and reaction stops, cooling discharge, reclaim the solvent Virahol and get crude product 4-propyl cyclohexyl, underpressure distillation gets elaboration, and content is more than 99.5%.
The principal reaction formula that above steps relates to is as follows:
1, the synthetic 4-propyl group pimelinketone of ethyl-para-hydroxyphenyl ketone high-pressure hydrogenation
2, grignard reaction
3, dehydration
4,4-propyl group tetrahydrobenzene benzene low-voltage hydrogenation
In step 1, palladium content is 5% (weight ratio) in the palladium/carbon catalyst, and this catalyzer is to add under protection of nitrogen gas, and oxygen free condition is to guarantee with the mode of nitrogen replacement in the still.
In 2-5 hour, bromobenzene is at the uniform velocity dripped off in the step 2.
After the hydrochloric acid soln hydrolysis of step 3 adding 10%, the PH of reactant should be controlled at 1-2.
Underpressure distillation in the step 1 or 4 is to carry out under 5～8mmHg vacuum.
The present invention replaces n-propyl phenol's production that the yield of propyl group cyclohexyl ketone is brought up to more than 90% by original 75-85% with ethyl-para-hydroxyphenyl ketone, and only this single step reaction cost promptly reduces 30-35%.Purity 〉=99.5% of the finished product 4-propyl cyclohexyl, appearance colorless is to little yellow liquid; Thereby improve the content and the outward appearance of currently available products.
Embodiment
Embodiment 1
1) 4-propyl group pimelinketone is synthetic
With the nitrogen pressure testing to more than the 2MPa; after guaranteeing that autoclave does not have leakage; drop into 7.987 moles of Virahols, 2.663 moles of ethyl-para-hydroxyphenyl ketones add 20g palladium/carbon catalyst (palladium content 5%) under nitrogen protection; airtight autoclave; guarantee in the still under the oxygen free condition with nitrogen replacement, feed hydrogen, be warming up to 70 degree to 0.45MPa; begin to inhale H-H reaction; reacted 4 hours, and inhaled hydrogen and stop, improving temperature to 155 degree gradually; hydrogen pressure is increased to 1.8MPa; continue hydrogenation with this understanding, till not inhaling hydrogen, sampling analysis; use gas chromatographic analysis; 4-propyl group cyclohexyl ketone content 98.7%, be cooled to 30 the degree, slowly release pressure after; with nitrogen material in the still is extruded; distillation gets crude product to 2.629 moles of propyl group pimelinketone after reclaiming Virahol, content 98.6%, and underpressure distillation gets 2.425 moles of elaboration 4-propyl group pimelinketone under the 6mmHg vacuum; with respect to the molar yield 91.06% of ethyl-para-hydroxyphenyl ketone, content 99.63%.
2) 4-propyl group-1-phenyl hexamethylene-1-alcohol is synthetic
Check before feeding intake that the dry nothing of reaction kit is dirty, in flask, drop into 2.08 moles of THF and 0.6 mole of magnesium powder, be warming up to 46 degree, add a small pieces iodine, after guaranteeing to cause, under this temperature condition, in the 3hr 0.586 mole of bromobenzene is at the uniform velocity dripped off, after bromobenzene dripped off, 46 degree were kept reaction 5hr, after sampling analysis is qualified, under 48 degree conditions, splash into 0.5 mole of 4-propyl group pimelinketone, drip keep 3hr after, pour hydrolysis in the aqueous hydrochloric acid into, control PH1-2.After hydrolysis is intact that material is static, normal pressure is sloughed solvent THF behind the branch water-yielding stratum.
3) 4-propyl group tetrahydrobenzene benzene is synthetic
Add 2 moles of toluene, 0.032 mole of PTS dehydration, 2.5hr sampling analysis, 4-propyl group tetrahydrobenzene benzene content 94.2%, distillation is reclaimed toluene and is got crude product, gets 0.4075 mole of elaboration 4-propyl group tetrahydrobenzene benzene through rectification under vacuum, content 99.2% is with respect to the molar yield 81.5% of 4-propyl group pimelinketone.
4) the 4-propyl cyclohexyl is synthetic
With 0.5 mole of 4-propyl group tetrahydrobenzene benzene, 2.5 moles of Virahols drop in the 500ml autoclave, add the 10g skeleton nickel, sealing autoclave behind nitrogen replacement, feeds hydrogen, be warming up to 58 degree, begin to inhale H-H reaction, behind the feeding hydrogen 3hr, reaction stops, cooling discharge reclaims the solvent Virahol and gets crude product 4-propyl cyclohexyl, and vacuum rectification under vacuum under 7mmHg gets 0.471 mole of product, content 99.71% is with respect to the molar yield 94.26% of 4-propyl group tetrahydrobenzene benzene.
Embodiment 2
1) 4-propyl group pimelinketone is synthetic
With the nitrogen pressure testing to more than the 2MPa; after guaranteeing that autoclave does not have leakage; drop into 4.0 moles of Virahols, 2.663 moles of ethyl-para-hydroxyphenyl ketones add 28g palladium/carbon catalyst (palladium content 5%) under nitrogen protection; airtight autoclave; guarantee in the still under the oxygen free condition with nitrogen replacement, feed hydrogen, be warming up to 85 degree to 0.7MPa; begin to inhale H-H reaction; reacted 5.5 hours, and inhaled hydrogen and stop, improving temperature to 172 degree gradually; hydrogen pressure is increased to 2.3MPa; continue hydrogenation with this understanding, till not inhaling hydrogen, sampling analysis; use gas chromatographic analysis; 4-propyl group cyclohexanone content 98.9%, be cooled to 23 the degree, slowly release pressure after; with nitrogen material in the still is extruded; distillation gets crude product to 2.628 moles of propyl group pimelinketone after reclaiming Virahol, content 99.01%, and underpressure distillation gets 2.424 moles of elaboration 4-propyl group pimelinketone under the 7.5mmHg vacuum; with respect to the molar yield 91.03% of ethyl-para-hydroxyphenyl ketone, content 99.58%.
2) 4-propyl group-1-phenyl hexamethylene-1 alcohol is synthetic
Check before feeding intake that the dry nothing of reaction kit is dirty, in flask, drop into 2.15 moles of THF and 0.525 mole of magnesium powder, be warming up to 58 degree, add a small pieces iodine, after guaranteeing to cause, under this temperature condition, in the 2.5hr 0.56 mole of bromobenzene is at the uniform velocity dripped off, after bromobenzene drips off, keep reaction 3.5hr at 41 degree, after sampling analysis is qualified, under 48 degree conditions, splash into 0.5 mole of 4-propyl group pimelinketone, drip keep 4.5hr after, pour hydrolysis in the aqueous hydrochloric acid into, control PH1-2, after hydrolysis is intact that material is static, normal pressure is sloughed solvent THF behind the branch water-yielding stratum.
3) 4-propyl group tetrahydrobenzene benzene is synthetic
Add 1.22 moles of toluene, 0.012 mole PTS dehydration, the 2hr sampling analysis, 4-propyl group tetrahydrobenzene benzene content 94.7%, distillation is reclaimed toluene and is got crude product, get 0.4052 mole of elaboration 4-propyl group tetrahydrobenzene benzene through rectification under vacuum, content 99.15% is with respect to the molar yield 81.04% of 4-propyl group pimelinketone.
4) the 4-propyl cyclohexyl is synthetic
With 0.5 mole of 4-propyl group tetrahydrobenzene benzene, 1.5 moles of Virahols drop in the 500ml autoclave, add the 5g skeleton nickel, sealing autoclave behind nitrogen replacement, feeds hydrogen, be warming up to 55 degree, begin to inhale H-H reaction, behind the feeding hydrogen 2hr, reaction stops, cooling discharge reclaims the solvent Virahol and gets crude product 4-propyl cyclohexyl, and vacuum rectification under vacuum under 5mmHg gets 0.4705 mole of product, content 99.8% is with respect to the molar yield 94.10% of 4-propyl group tetrahydrobenzene benzene.
Embodiment three:
1) 4-propyl group pimelinketone is synthetic
With the nitrogen pressure testing to more than the 2MPa; after guaranteeing that autoclave does not have leakage; drop into 10 moles of Virahols, 2.663 moles of ethyl-para-hydroxyphenyl ketones add 16g palladium/carbon catalyst (palladium content 5%) under nitrogen protection; airtight autoclave; guarantee in the still under the oxygen free condition with nitrogen replacement, feed hydrogen, be warming up to 53 degree to 0.35MPa; begin to inhale H-H reaction; reacted approximately 2.5 hours, and inhaled hydrogen and stop, improving temperature to 145 degree gradually; hydrogen pressure is increased to 1.5MPa; continue hydrogenation with this understanding, till not inhaling hydrogen, sampling analysis; use gas chromatographic analysis; 4-propyl group cyclohexyl ketone content 98.65%, be cooled to 35 the degree, slowly release pressure after; with nitrogen material in the still is extruded; distillation gets crude product to 2.627 moles of propyl group pimelinketone after reclaiming Virahol, content 98.71%, and underpressure distillation gets 2.426 moles of elaboration 4-propyl group pimelinketone under the 5.5mmHg vacuum; with respect to the molar yield 91.1% of ethyl-para-hydroxyphenyl ketone, content 99.53%.
2) 4-propyl group-1-phenyl hexamethylene-1 alcohol is synthetic
Check before feeding intake that the dry nothing of reaction kit is dirty, in flask, drop into 2.05 moles of THF and 0.55 mole of magnesium powder, be warming up to 55 degree, add a small pieces iodine, after guaranteeing to cause, under this temperature condition, in the 4.5hr 0.575 mole of bromobenzene is at the uniform velocity dripped off, after bromobenzene drips off, 56 degree are kept reaction 5.5hr, after sampling analysis is qualified, under 60 degree conditions, splash into 0.5 mole of 4-propyl group pimelinketone, drip keep 2.2hr after, pour hydrolysis in the aqueous hydrochloric acid into, control PH1-2, after hydrolysis is intact that material is static, normal pressure is sloughed solvent THF behind the branch water-yielding stratum.
3) 4-propyl group tetrahydrobenzene benzene is synthetic
Add 1.5 moles of toluene, 0.034 mole PTS dehydration, the 3hr sampling analysis, 4-propyl group tetrahydrobenzene benzene content 94.89%, distillation is reclaimed toluene and is got crude product, get 0.4061 mole of elaboration 4-propyl group tetrahydrobenzene benzene through rectification under vacuum, content 99.58% is with respect to the molar yield 81.22% of 4-propyl group pimelinketone.
4) the 4-propyl cyclohexyl is synthetic
With 0.5 mole of 4-propyl group tetrahydrobenzene benzene, 3 moles of Virahols drop in the 500ml autoclave, add the 10g skeleton nickel, sealing autoclave behind nitrogen replacement, feeds hydrogen, be warming up to 51 degree, begin to inhale H-H reaction, behind the feeding hydrogen 2.5hr, reaction stops, cooling discharge reclaims the solvent Virahol and gets crude product 4-propyl cyclohexyl, and vacuum rectification under vacuum under 8mmHg gets 0.4712 mole of product, content 99.68% is with respect to the molar yield 94.24% of 4-propyl group tetrahydrobenzene benzene.
Claims (7)
1, a kind of preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene is characterized in that comprising being prepared as follows step:
1) the synthetic 4-propyl group pimelinketone of ethyl-para-hydroxyphenyl ketone high-pressure hydrogenation
Virahol and ethyl-para-hydroxyphenyl ketone are pressed 1: 1-4: 1 mol ratio drops in the reactor, add palladium/carbon catalyst simultaneously, the weight ratio 10 of ethyl-para-hydroxyphenyl ketone and palladium/carbon catalyst: 1-30: 1, under oxygen free condition, feed hydrogen to 0.3-0.8MPa, be warming up to 50-90 ℃, react and stop the back to hydrogenation and improve temperature to 140～180 ℃, hydrogen pressure is increased to 1.3-2.5MPa, continue hydrogenation with this understanding, be not cooled to 20-40 ℃ after do not inhale hydrogen, slowly release pressure after, with nitrogen material in the still is extruded, distillation gets crude product to the propyl group pimelinketone after reclaiming Virahol, gets elaboration 4-propyl group pimelinketone through underpressure distillation again;
2) grignard reaction
In reactor, add THF and magnesium powder, add iodine after being warming up to 40-60 ℃, after the initiation bromobenzene is at the uniform velocity splashed into reactor, drip off the back 40-60 ℃ of reaction 3-6 hour, under 45-65 ℃ of condition, splash into the 4-propyl group pimelinketone that step 1 makes, drip and keep reaction after 2-5 hour, add the hydrochloric acid soln hydrolysis, after hydrolysis is intact that material is static, normal pressure is sloughed THF behind the branch water-yielding stratum, obtains 4-propyl group-1-phenyl hexamethylene-1 alcohol; Wherein, the mol ratio of THF and 4-propyl group pimelinketone is 4.5: 1-4.1: 1, and the mol ratio of magnesium powder and 4-propyl group pimelinketone is 1.04: 1-1.34: 1, the mol ratio of bromobenzene and 4-propyl group pimelinketone is 1.1: 1-1.2: 1;
3) dehydration reaction
Add toluene and p-methyl benzenesulfonic acid catalyzer, react and distill recovery toluene after 2-3 hour and get crude product, get elaboration 4-propyl group tetrahydrobenzene benzene through rectification under vacuum again; Wherein, the mol ratio of catalyzer toluene and 4-propyl group pimelinketone is 4: 1-2: 1, and the mol ratio of PTS and 4-propyl group pimelinketone is 0.0232: 1-0.0696: 1;
4) with 4-propyl group tetrahydrobenzene benzene, Virahol in molar ratio 3: 1-6: 1 drops in the autoclave, adds skeletal nickel catalyst, and the weight ratio of skeleton nickel and 4-propyl group tetrahydrobenzene benzene is 0.05: 1-0.2: 1, sealing autoclave, behind nitrogen replacement, feed hydrogen, be warming up to 50-60 ℃, the beginning hydrogenation, feed hydrogen after 2-3 hour, reaction stops, cooling discharge, reclaim the solvent Virahol and get crude product 4-propyl cyclohexyl, underpressure distillation gets elaboration.
2, the preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene according to claim 1 is characterized in that palladium/carbon catalyst is to add in the step 1 under protection of nitrogen gas.
3, the preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene according to claim 1 is characterized in that guaranteeing oxygen free condition in the still with nitrogen replacement in the step 1.
4, the preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene according to claim 1 is characterized in that palladium content is 5% in the palladium/carbon catalyst in the step 1.
5, the preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene according to claim 1 is characterized in that the underpressure distillation in step 1 or 4 is to carry out under 5～8mmHg vacuum.
6, the preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene according to claim 1 is characterized in that in 2-5 hour bromobenzene at the uniform velocity being dripped off in the step 2.
7, the preparation method of liquid crystal chemicals 4-propyl cyclohexyl benzene according to claim 1 is characterized in that the concentration of step 2 adding hydrochloric acid is 10%, and the PH of hydrolysis afterreaction thing should be controlled at 1-2.
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| CN100577636C (en) * | 2006-11-20 | 2010-01-06 | 烟台万润精细化工股份有限公司 | Preparation method of benzonitrile monomer liquid crystal |
| CN101560396B (en) * | 2009-04-10 | 2012-07-25 | 莱阳市盛华科技有限公司 | Method for synthesizing fluorine-containing antiform alkyl cyclohexyl biphenyl single liquid crystal |
| CN115197055A (en) * | 2022-05-31 | 2022-10-18 | 湖南华腾医药有限公司 | Method for synthesizing 4-propylcyclohexanone by continuous flow microreactor |
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| JPS63250332A (en) * | 1987-04-03 | 1988-10-18 | Dainippon Ink & Chem Inc | Fluorotrane based nematic compound |
| CN1281845A (en) * | 1999-11-26 | 2001-01-31 | 石彩云 | Synthesis method of alpha-hydroxycyclohexylbenzyl ketone |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63250332A (en) * | 1987-04-03 | 1988-10-18 | Dainippon Ink & Chem Inc | Fluorotrane based nematic compound |
| CN1281845A (en) * | 1999-11-26 | 2001-01-31 | 石彩云 | Synthesis method of alpha-hydroxycyclohexylbenzyl ketone |
Non-Patent Citations (1)
| Title |
|---|
| 4-丙基环己酮新合成方法 杨永忠，化学试剂，第27卷第1期 2005 * |
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