CN104926611A - Novel process for preparing benzyl alcohol by alkali-free continuous hydrolysis of benzyl chloride - Google Patents
Novel process for preparing benzyl alcohol by alkali-free continuous hydrolysis of benzyl chloride Download PDFInfo
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- CN104926611A CN104926611A CN201510286820.6A CN201510286820A CN104926611A CN 104926611 A CN104926611 A CN 104926611A CN 201510286820 A CN201510286820 A CN 201510286820A CN 104926611 A CN104926611 A CN 104926611A
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
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Abstract
The invention relates to a novel process for preparing benzyl alcohol by alkali-free continuous hydrolysis of benzyl chloride. The process comprises the following steps of adding benzyl chloride, pure water and a specific mixed solvent of methylbenzene and cyclohexane into a primary normal-pressure reaction kettle according to a certain proportion, performing reaction for a certain time at certain temperature, continuing transferring a reaction product into a secondary pressure reaction kettle, adding an isopropylbenzene solvent, simultaneously adding methyl trioctyl ammonium chloride quaternary ammonium salt, continuing performing reaction for a certain time, cooling and settling obtained reaction liquid to separate an oil phase and an aqueous phase (containing benzyl alcohol and hydrochloric acid), and performing crude distillation and rectification on the oil phase to obtain a benzyl alcohol finished product. According to the process, a continuous feeding and discharging manner is adopted for reaction, and a corresponding solvent and a corresponding catalyst are combined, so that the yield rate of the product is increased, and the productivity is improved.
Description
Technical field
The present invention's design relates to the preparation method of phenylcarbinol, mainly comprises Benzyl Chloride prepares phenylcarbinol industrialized producing technology without basic hydrolysis.
Technical background
Along with the development of national economy, China fine chemical product kind and be all quantitatively the impetus increased fast, phenylcarbinol is an important Organic chemical products and intermediate as the extension product of Benzyl Chloride, be widely used in the every profession and trade such as medicine, spices, in addition, due to continually developing of phenylcarbinol derived product, the usage quantity of phenylcarbinol will significantly increase.
The main production process of phenylcarbinol has 2 kinds: phenyl aldehyde catalytic reduction method and Benzyl Chloride hydrolysis method.Phenyl aldehyde catalytic reduction method is the main method of producing before the eighties to the nineties, and this synthesis method has been run counter to by the rudimentary rule to senior development, and cost is also very high, now substantially superseded.Benzyl Chloride hydrolysis method is divided has alkali reaction and without alkali reaction 2 kinds, existing main production is Benzyl Chloride alkaline hydrolysis, its flow process is that Benzyl Chloride and soda ash solution mix in a kettle. with certain proportion, by temperature rising reflux reaction 6 ~ 10h, obtain the mixing crude product of phenylcarbinol and dibenzyl ether, this defective workmanship is sodium chloride-containing in waste water, and by product production rate is crossed up to 10 ~ 25%.Processing cost is higher, and another Benzyl Chloride transformation efficiency only 75 ~ 80%, dibenzyl ether accounting crude reaction is up to 8 ~ 12%, and its value is lower, and range of application is wideless.Therefore the technique research and development that urgent need is carried out without alkali reaction.
Summary of the invention
Instant invention overcomes the defect of prior art, provide a kind of economic environmental protection, the phenylcarbinol production method of constant product quality.With solving sodium chloride-containing in existing processing wastewater, and by product production rate is crossed up to 10 ~ 25%.Processing cost is high-technology problem comparatively.
In addition, this invention also solves Benzyl Chloride transformation efficiency only 75 ~ 80%, dibenzyl ether accounting crude reaction, up to 8 ~ 12%, is worth lower, the technical problems such as range of application is wideless.
In order to solve above technical problem, the present invention is achieved by the following technical solutions: a kind of Benzyl Chloride alkali-free continuous hydrolysis prepares the novel process of phenylcarbinol, it is characterized in that this processing step is as follows:
A, tetradecyl trimethyl ammonium chloride and water are hybridly prepared into the tetradecyl trimethyl ammonium chloride aqueous solution of massfraction 100 ~ 1000ppm;
B, by the tetradecyl trimethyl ammonium chloride aqueous solution and Benzyl Chloride, toluene and hexanaphthene mixed solvent according to mass ratio 1:(0.2 ~ 0.3): (0.05 ~ 0.06) puts into A reactor, stir, heating, at 90 ~ 105 DEG C, reacts 2 ~ 10h under condition of normal pressure;
C, the mixture after synthesis under normal pressure is produced to two-stage pressurizing still by static mixer continuously, add isopropyl benzene solvent, add tri-n-octyl methyl ammonium chloride quaternary ammonium salt to stir simultaneously, be heated to 110 ~ 150 DEG C, at 0.3 ~ 0.5mpa, under nitrogen protection condition, react 3 ~ 5h;
D, reacted mixture carry out cooling, sedimentation, isolate oil phase;
E, oil phase by slightly to heat up in a steamer isolate solvent and unreacted completely Benzyl Chloride return synthesis under normal pressure and react further, then obtain high-purity benzene methyl alcohol by rectifying separation.
As preferably, in described toluene and hexanaphthene mixed solvent, the ratio of toluene and hexanaphthene is 1:1.
The present invention is by Benzyl Chloride, pure water, specific toluene and hexanaphthene mixed solvent join in one-level normal-pressure reaction kettle according to a certain percentage, be transferred in two-stage pressurizing reactor continuously after reacting certain hour at a certain temperature, add isopropyl benzene solvent, add simultaneously tri-n-octyl methyl ammonium chloride quaternary ammonium salt continue the reaction solution of gained after reaction certain hour through carrying out cooling, sedimentation, isolate oil phase and aqueous phase (containing phenylcarbinol, hydrochloric acid), oil phase through slightly heat up in a steamer with rectifying after phenylcarbinol finished product.
Present invention process advantage is:
1. main containing hydrogen chloride and phenylcarbinol in waste water, process is convenient; Reactive system is without soda ash, and cost reduces; Introduce the mixture of benzene compounds and high boiling solvent.Introduce Phase TransferCatalyst simultaneously and promote speed of response, ensure producing in time, in order to avoid the aggravation of side reaction of material.
2. technique adopts continuous feeding and discharging mode to react, and in conjunction with corresponding solvent and catalyzer, improves the output capacity of product, increases production capacity.Wherein first order reaction is atmospheric operation, guarantees that Benzyl Chloride transformation efficiency reaches 75 ~ 85%, avoids a large amount of generations causing dibenzyl ether in pressure process because Benzyl Chloride is excessive; Second order reaction; Second order reaction adopts pressurized operation, promotion unreacted completely Benzyl Chloride reacts further, Benzyl Chloride transformation efficiency >99.5%, isopropyl benzene solvent exists, side reaction is suppressed, phenylcarbinol accounting >98% in reaction product, dibenzyl ether accounting <2% (the remained unreacted Benzyl Chloride completely in deduction product).
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail, but the present invention is not limited to described embodiment.
Embodiment 1:
0.3Kg benzyltriethylammoinium chloride is added in 1500Kg water, the benzyltriethylammoinium chloride aqueous solution and 300Kg Benzyl Chloride, 20Kg toluene, 20Kg hexanaphthene are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 34.72%, containing phenylcarbinol 64.28%, containing dibenzyl ether 0.94%.Reaction solution is all transferred to second order reaction still, add 0.3Kg tri-n-octyl methyl ammonium chloride quaternary ammonium salt simultaneously, 30Kg isopropyl benzene solvent is opened and stirred and heat, passing into nitrogen adjustment still internal pressure is 0.6Mpa, timing is started when still temperature rise to 150 DEG C, react sampling analysis after 4 hours, oil phase chloride containing benzyl 0.47%, containing phenylcarbinol 97.8%, containing dibenzyl ether 1.73%.Benzyl Chloride transformation efficiency=99.53%, phenylcarbinol reaction preference=98.26%, dibenzyl ether reaction preference=1.74%.
Embodiment 2:
0.5Kg tetradecyl trimethyl ammonium chloride is added in 1500Kg water, the tetradecyl trimethyl ammonium chloride aqueous solution and 300Kg Benzyl Chloride, 30Kg toluene, 30Kg hexanaphthene are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 35.56%, containing phenylcarbinol 63.26%, containing dibenzyl ether 1.08%.Reaction solution is all transferred to second order reaction still, add 40Kg isopropyl benzene simultaneously, 0.2Kg tri-n-octyl methyl ammonium chloride quaternary ammonium salt is opened and stirred and heat, passing into nitrogen adjustment still internal pressure is 0.6Mpa, timing is started when still temperature rise to 150 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 0.45%, containing phenylcarbinol 97.75%, containing dibenzyl ether 1.75%.Benzyl Chloride transformation efficiency=99.55%, phenylcarbinol reaction preference=98.24%, dibenzyl ether reaction preference=1.76%.
Embodiment 3:
0.5Kg tetradecyl trimethyl ammonium chloride is added in 1500Kg water, the tetradecyl trimethyl ammonium chloride aqueous solution and 300Kg Benzyl Chloride, 30Kg toluene, 30Kg hexanaphthene are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 8 hours, oil phase chloride containing benzyl 10.12%, containing phenylcarbinol 85.34%, containing dibenzyl ether 4.28%.Reaction solution is all transferred to second order reaction still, add 40Kg isopropyl benzene simultaneously, 0.2Kg tri-n-octyl methyl ammonium chloride quaternary ammonium salt is opened and stirred and heat, passing into nitrogen adjustment still internal pressure is 0.6Mpa, timing is started when still temperature rise to 150 DEG C, react sampling analysis after 5 hours, oil phase chloride containing benzyl 0.48%, containing phenylcarbinol 97.66%, containing dibenzyl ether 1.62%.Post chlorization benzyl transformation efficiency=99.52%, phenylcarbinol reaction preference=98.36%, dibenzyl ether reaction preference=1.63%.
In order to verify effect of the present invention, inventor has devised following Experimental Comparison example and effect evaluation and test carried out to the present invention:
Comparative example 1: 0.5Kg tetradecyl trimethyl ammonium chloride is added in 1500Kg water, the tetradecyl trimethyl ammonium chloride aqueous solution and 300Kg Benzyl Chloride, 30Kg toluene, 30Kg hexanaphthene are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 35.56%, containing phenylcarbinol 63.26%, containing dibenzyl ether 1.08%.Reaction solution is all transferred to second order reaction still, add 40Kg isopropyl benzene simultaneously, 0.2Kg tri-n-octyl methyl ammonium chloride quaternary ammonium salt is opened and stirred and heat, passing into nitrogen adjustment still internal pressure is 0.6Mpa, timing is started when still temperature rise to 150 DEG C, react sampling analysis after 1 hour, oil phase chloride containing benzyl 15.6%, containing phenylcarbinol 83.15%, containing dibenzyl ether 1.12%.Benzyl Chloride transformation efficiency=84.4%, phenylcarbinol reaction preference=98.67%, dibenzyl ether reaction preference=1.33%.
Comparative example 2: 0.3Kg benzyltriethylammoinium chloride is added in 1500Kg water, the benzyltriethylammoinium chloride aqueous solution and 300Kg Benzyl Chloride, 25Kg toluene, 20Kg hexanaphthene are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 34.72%, containing phenylcarbinol 64.28%, containing dibenzyl ether 0.94%.Reaction solution is all transferred to second order reaction still, add 0.3Kg tri-n-octyl methyl ammonium chloride quaternary ammonium salt simultaneously, 30Kg isopropyl benzene solvent is opened and stirred and heat, passing into nitrogen adjustment still internal pressure is 0.6Mpa, timing is started when still temperature rise to 150 DEG C, react sampling analysis after 6 hours, oil phase chloride containing benzyl 0.38%, containing phenylcarbinol 94.4%, containing dibenzyl ether 5.22%.React 6 hours post chlorization benzyl transformation efficiency=99.62%, phenylcarbinol reaction preference=94.76%, dibenzyl ether reaction preference=5.24%.
Comparative example 3:
1500kg water and 300Kg Benzyl Chloride are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 22.5%, containing phenylcarbinol 68.19%, containing dibenzyl ether 6.23%.React sampling analysis after 6 hours, oil phase chloride containing benzyl 15.7%, containing phenylcarbinol 63.52%, containing dibenzyl ether 17.8%.
Benzyl Chloride transformation efficiency=84.3%, phenylcarbinol reaction preference=78.11%, dibenzyl ether reaction preference=21.89%.
Comparative example 4:
1500kg water and 300Kg Benzyl Chloride, 75Kg toluene are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 57.5%, containing phenylcarbinol 40.5%, containing dibenzyl ether 0.5%.React sampling analysis after 6 hours, oil phase chloride containing benzyl 27.8%, containing phenylcarbinol 68.9%, containing dibenzyl ether 3.8%.
Benzyl Chloride transformation efficiency=72.2%, phenylcarbinol reaction preference=94.77%, dibenzyl ether reaction preference=5.23%.
Comparative example 5
1500kg water and 300Kg Benzyl Chloride, 45Kg toluene, 30Kg hexanaphthene, 0.3Kg tetradecyl trimethyl ammonium chloride are joined in the reactor that heating, stirring, thermometer and prolong are housed, open and stir and heat, timing is started when still temperature rise to 92 DEG C, react sampling analysis after 3 hours, oil phase chloride containing benzyl 35.8%, containing phenylcarbinol 62.56%, containing dibenzyl ether 1.85%.React sampling analysis after 6 hours, oil phase chloride containing benzyl 15.5%, containing phenylcarbinol 77.78%, containing dibenzyl ether 5.3%.
Benzyl Chloride transformation efficiency=84.5%, phenylcarbinol reaction preference=93.62%, dibenzyl ether reaction preference=6.38%.
In above embodiment and comparative example, Benzyl Chloride, phase-transfer catalyst, solvent are technical grade.Reaction leading indicator comprises phenylcarbinol in Benzyl Chloride transformation efficiency, product, dibenzyl ether content, determines by chromatography of gases.
Conclusion: contrasted by embodiment 1,2,3 and comparative example 3,4,5 and show: the Benzyl Chloride transformation efficiency of present invention process, product purity, production efficiency are all very high, have good industrial application value.In addition, contriver shows through repeatedly studying, find that there is considerable influence the compressive reaction time to Benzyl Chloride transformation efficiency, product purity, contrasted by embodiment 1,2,3 and comparative example 1,2, be not difficult to find, the compressive reaction time that Benzyl Chloride alkali-free continuous hydrolysis prepares phenylcarbinol is ideal with 3 ~ 5 hours.
Claims (2)
1. Benzyl Chloride alkali-free continuous hydrolysis prepares a novel process for phenylcarbinol, it is characterized in that this processing step is as follows:
A, tetradecyl trimethyl ammonium chloride and water are hybridly prepared into the tetradecyl trimethyl ammonium chloride aqueous solution of massfraction 100 ~ 1000ppm;
B, by the tetradecyl trimethyl ammonium chloride aqueous solution and Benzyl Chloride, toluene and hexanaphthene mixed solvent according to mass ratio 1:(0.2 ~ 0.3): (0.05 ~ 0.06) puts into A reactor, stir, heating, at 90 ~ 105 DEG C, reacts 2 ~ 10h under condition of normal pressure;
C, the mixture after synthesis under normal pressure is produced to two-stage pressurizing still by static mixer continuously, add isopropyl benzene solvent, add tri-n-octyl methyl ammonium chloride quaternary ammonium salt to stir simultaneously, be heated to 110 ~ 150 DEG C, at 0.3 ~ 0.5mpa, under nitrogen protection condition, react 3 ~ 5h;
D, reacted mixture carry out cooling, sedimentation, isolate oil phase;
E, oil phase by slightly to heat up in a steamer isolate solvent and unreacted completely Benzyl Chloride return synthesis under normal pressure and react further, then obtain high-purity benzene methyl alcohol by rectifying separation.
2. a kind of Benzyl Chloride alkali-free continuous hydrolysis according to claim 1 prepares the novel process of phenylcarbinol, it is characterized in that in described toluene and hexanaphthene mixed solvent, and the ratio of toluene and hexanaphthene is 1:1.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105924328A (en) * | 2016-05-19 | 2016-09-07 | 连云港市工业投资集团有限公司 | High-selectivity green hydrolysis technology for preparing benzyl alcohol |
| CN108129268A (en) * | 2018-01-12 | 2018-06-08 | 潜江新亿宏有机化工有限公司 | A kind of benzyl alcohol continuous rectification system |
| CN109734555A (en) * | 2019-02-01 | 2019-05-10 | 武汉格源精细化学有限公司 | Preparation method of the high-purity to methylbenzyl alcohol |
| CN110606798A (en) * | 2019-10-11 | 2019-12-24 | 武汉有机实业有限公司 | Method for preparing benzyl alcohol by using microchannel reactor without alkali |
| CN110776398A (en) * | 2019-11-08 | 2020-02-11 | 聊城鲁西氯苄化工有限公司 | Benzyl alcohol step pressure hydrolysis reaction process and system |
| US11926761B2 (en) * | 2018-08-02 | 2024-03-12 | Sk Innovation Co., Ltd. | Organic solvent composition and paint composition including the same |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105924328A (en) * | 2016-05-19 | 2016-09-07 | 连云港市工业投资集团有限公司 | High-selectivity green hydrolysis technology for preparing benzyl alcohol |
| CN105924328B (en) * | 2016-05-19 | 2019-01-18 | 连云港市工业投资集团有限公司 | A kind of highly selective green hydrolysis technique for preparing benzyl alcohol |
| CN108129268A (en) * | 2018-01-12 | 2018-06-08 | 潜江新亿宏有机化工有限公司 | A kind of benzyl alcohol continuous rectification system |
| US11926761B2 (en) * | 2018-08-02 | 2024-03-12 | Sk Innovation Co., Ltd. | Organic solvent composition and paint composition including the same |
| CN109734555A (en) * | 2019-02-01 | 2019-05-10 | 武汉格源精细化学有限公司 | Preparation method of the high-purity to methylbenzyl alcohol |
| CN110606798A (en) * | 2019-10-11 | 2019-12-24 | 武汉有机实业有限公司 | Method for preparing benzyl alcohol by using microchannel reactor without alkali |
| CN116178106A (en) * | 2019-10-11 | 2023-05-30 | 武汉有机实业有限公司 | Method for preparing benzyl alcohol by using micro-channel reactor without alkali |
| CN110776398A (en) * | 2019-11-08 | 2020-02-11 | 聊城鲁西氯苄化工有限公司 | Benzyl alcohol step pressure hydrolysis reaction process and system |
| CN110776398B (en) * | 2019-11-08 | 2024-03-22 | 鲁西化工集团股份有限公司氯碱化工分公司 | Benzyl alcohol step pressurizing hydrolysis reaction process and system |
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