CN105949059A - Simple and efficient production method for phenyl chloroformate - Google Patents
Simple and efficient production method for phenyl chloroformate Download PDFInfo
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- CN105949059A CN105949059A CN201610384246.2A CN201610384246A CN105949059A CN 105949059 A CN105949059 A CN 105949059A CN 201610384246 A CN201610384246 A CN 201610384246A CN 105949059 A CN105949059 A CN 105949059A
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- retort
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
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Abstract
The invention provides a simple and efficient production method for phenyl chloroformate. The production method comprises the following steps that firstly, phenol is treated into a molten state for use; secondly, phenol is transferred into a phenol spray tank, and a catalyst is transferred into a catalyst spray tank; thirdly, a circulating refrigerating machine is started, then a temperature control pipeline is controlled, a reaction tank is heated, phosgene is introduced into the reaction tank continuously, then the phenol spray tank is started, stirring is started, the catalyst spray tank is started, and central control samples are taken; finally, gas dispelling is carried out on the reaction tank with nitrogen, and phenyl chloroformate is obtained through reduced pressure distillation. Compared with an existing production technology, by means of the simple and efficient production method for phenyl chloroformate, the reaction time is shortened, and the purity and the reaction efficiency are improved.
Description
Technical field
The present invention relates to fine chemistry industry production field, be specifically related to the producer of a kind of simple efficient phenyl chloroformate
Method.
Background technology
Phenyl chloroformate is a kind of important fine-chemical intermediate, has extensive use in terms of chemical industry synthesis, permissible
As polymerization catalyst, plastic modifier, fibre finish, and medicine, the intermediate of pesticide.
The primary synthetic methods of phenyl chloroformate is phosgenation, is dissolved in by phenol under chloroform, cooling and is passed through phosgene, makes absorption
The amount ratio of the material such as light tolerance and phenol, in the amount DMA of the materials such as the 5-10 DEG C of lower dropping of stirring.Then add
Cold water dilutes, and divides and takes oil reservoir, successively with dilute hydrochloric acid and water washing.Dried through anhydrous calcium chloride, Distillation recovery chloroform, then reduce pressure
Rectification, collects 74-75 DEG C of (1.73kPa) fraction, is phenyl chloroformate, yield about 90%.The method post processing is complicated, needs
Reclaiming substantial amounts of solvent, the wastewater flow rate of generation is more, and uses substantial amounts of DMA to do acid binding agent, production cost
High.
The existing production method disclosing the simply efficient phenyl chloroformate of a kind of solventless method, directly adds melted phenol
Entering a small amount of catalyst, high temperature leads to light, then obtains the content phenyl chloroformate more than 98%, the method post processing by rectification under vacuum
Simply, it is to avoid a large amount of acid binding agents and the use of solvent, producing without technique waste water, cost is relatively low, is suitable for industrialized production.
But existing technology there is also by-product production, production efficiency also ratio is relatively low simultaneously, benzene the most in process of production
Phenol can produce by-product diphenyl carbonate (DPC) with product phenyl chloroformate, i.e. under conditions of high temperature and acid binding agent
Summary of the invention
For above problems of the prior art, the invention provides the life of a kind of simple efficient phenyl chloroformate
Product method, decreases the generation of by-product, improves production efficiency.
The present invention is achieved by the following technical solutions:
A kind of production method of simple efficient phenyl chloroformate, its production method comprises the following steps:
1) phenol is processed into molten condition standby；
2) phenol of step 1 is transferred in phenol aerosol can, catalyst is transferred in catalyst spray tank, described benzene
Phenol aerosol can is arranged on the top of retort, and catalyst spray tank is arranged on the side of retort, and catalyst spray tank and benzene
The liquid outlet of phenol aerosol can bottom all connects drain pipe, and the liquid outlet of described drain pipe arranges shower nozzle, described catalyst spray tank
Shower nozzle be arranged on the middle part of retort inwall, and the middle and upper part of the shower nozzle orientating reaction tank of catalyst spray tank, described phenol
The shower nozzle of aerosol can is arranged on the top in described retort, and the middle part of retort arranges phosgene air inlet, and retort side is even
Connect circulating refrigerator；
3) first to ON cycle fridge, retort is carried out temperature and is increased to 80-90 DEG C, be then first passed through in retort
Phosgene, and the intake of phosgene is 1000-1500L, and it is continually fed into phosgene, it is then turned on phenol aerosol can, opens simultaneously
Catalyst spray tank, the response time is 3 hours, takes middle control sample, and gas phase normalizing analyzes phenyl chloroformate and Main By product carbonic acid
The area percentage of diphenyl ester；
4) above-mentioned middle control sample is extracted once for 20 minutes so that step 3 continues to be reacted to phenyl chloroformate and main by-product
The area percentage of thing diphenyl carbonate is not further added by, and now the time is 8 hours；
5), after step 4 retort employing nitrogen being caught up with gas, decompression distills out phenyl chloroformate.
Further, the outside of described retort arranges chuck, and the outer wall of described retort arranges temperature control zone road, temperature
Degree controls pipeline and is connected with described circulating refrigerator, and temperature controls described temperature control zone road and is positioned at the chuck of described retort,
The gas outlet on described retort top connects condenser, and described retort top plugs and is equipped with thermometer.
Further, wherein the ratio that mass ratio is discharge rate of catalyst and described phenol is 1:20.
Further, catalyst be DMAP, one or both mixture of DMA.
Further, phenol is 1:1.2 with the mol ratio of phosgene.
The invention have the benefit that the present invention's compares existing production technology, owing to using anhydrous response thing phenol
The mode of spraying, and phosgene reaction, under catalyst with certain temperature conditions so that the response time is little by existing 7-12
Time, shorten to 3-8 hour, quickly and completely react with phosgene owing to spray reaction enables to reactant phenol, it is possible to reduce
The generation of by-product diphenyl carbonate, therefore further increases the purity of product phenyl chloroformate, and purity can reach
99.0-99.6%, and this reaction be also easy to control, the most on the whole, more shorten the time of reaction, improve purity
And reaction efficiency.
Detailed description of the invention
In order to make the purpose of the present invention, technical scheme and advantage clearer, below in conjunction with embodiment, to the present invention
It is further elaborated.Should be appreciated that specific embodiment described herein, only in order to explain the present invention, is not used to
Limit the present invention.
Embodiment 1
First phenol is processed into molten condition standby；
Secondly above-mentioned phenol is transferred in phenol aerosol can, catalyst is transferred in catalyst spray tank, described benzene
Phenol aerosol can is arranged on the top of retort, and catalyst spray tank is arranged on the side of retort, and catalyst spray tank and benzene
The liquid outlet of phenol aerosol can bottom all connects drain pipe, and the liquid outlet of described drain pipe arranges shower nozzle, described catalyst spray tank
Shower nozzle be arranged on the middle part of retort inwall, and the middle and upper part of the shower nozzle orientating reaction tank of catalyst spray tank, described phenol
The shower nozzle of aerosol can is arranged on the top in described retort, and the middle part of retort arranges phosgene air inlet, and retort side is even
Connect circulating refrigerator；
Again first to ON cycle fridge, retort is carried out temperature and is increased to 80 DEG C, be then first passed through in retort
Phosgene, and the intake of phosgene is 1000L, and it is continually fed into phosgene, it is then turned on phenol aerosol can, opens catalyst simultaneously
Aerosol can, the response time is 3 hours, takes middle control sample, and gas phase normalizing analyzes phenyl chloroformate and Main By product diphenyl carbonate
Area percentage；
Thirdly above-mentioned middle control sample is extracted once for 20 minutes so that step 3 continues to be reacted to phenyl chloroformate with main
The area percentage of by-product diphenyl carbonate is not further added by, and now the time is 8 hours；
After finally above-mentioned retort employing nitrogen being caught up with gas, decompression distills out phenyl chloroformate.
The outside of described retort arranges chuck, and the outer wall of described retort arranges temperature control zone road, temperature control zone
Road is connected with described circulating refrigerator, and temperature controls described temperature control zone road and is positioned at the chuck of described retort, described reaction
The gas outlet of upper end connects condenser, and described retort top plugs and is equipped with thermometer.
Catalyst is 1:20 with the ratio that mass ratio is discharge rate of described phenol.
Catalyst is DMAP.
Phenol is 1:1.2 with the mol ratio of phosgene.
The present invention compares existing production technology, owing to using the mode of anhydrous response thing phenol spraying, anti-with phosgene
Should, under catalyst with certain temperature conditions so that the response time, by existing 7-12 hour, shortens to 3-8 hour, due to
Spray reaction enables to reactant phenol and quickly and completely reacts with phosgene, it is possible to reduce the product of by-product diphenyl carbonate
Raw, therefore further increase the purity of product phenyl chloroformate, and purity can reach 99.0%, and this reaction is also easy to
Control, the most on the whole, more shorten the time of reaction, improve purity and reaction efficiency.
Embodiment 2
First phenol is processed into molten condition standby；
Secondly above-mentioned phenol is transferred in phenol aerosol can, catalyst is transferred in catalyst spray tank, described benzene
Phenol aerosol can is arranged on the top of retort, and catalyst spray tank is arranged on the side of retort, and catalyst spray tank and benzene
The liquid outlet of phenol aerosol can bottom all connects drain pipe, and the liquid outlet of described drain pipe arranges shower nozzle, described catalyst spray tank
Shower nozzle be arranged on the middle part of retort inwall, and the middle and upper part of the shower nozzle orientating reaction tank of catalyst spray tank, described phenol
The shower nozzle of aerosol can is arranged on the top in described retort, and the middle part of retort arranges phosgene air inlet, and retort side is even
Connect circulating refrigerator；
Again first to ON cycle fridge, retort is carried out temperature and is increased to 83 DEG C, be then first passed through in retort
Phosgene, and the intake of phosgene is 1200L, and it is continually fed into phosgene, it is then turned on phenol aerosol can, opens catalyst simultaneously
Aerosol can, the response time is 3 hours, takes middle control sample, and gas phase normalizing analyzes phenyl chloroformate and Main By product diphenyl carbonate
Area percentage；
Thirdly above-mentioned middle control sample is extracted once for 20 minutes so that step 3 continues to be reacted to phenyl chloroformate with main
The area percentage of by-product diphenyl carbonate is not further added by, and now the time is 8 hours；
After finally above-mentioned retort employing nitrogen being caught up with gas, decompression distills out phenyl chloroformate.
The outside of described retort arranges chuck, and the outer wall of described retort arranges temperature control zone road, temperature control zone
Road is connected with described circulating refrigerator, and temperature controls described temperature control zone road and is positioned at the chuck of described retort, described reaction
The gas outlet of upper end connects condenser, and described retort top plugs and is equipped with thermometer.
Catalyst is 1:20 with the ratio that mass ratio is discharge rate of described phenol.
Catalyst is DMAP, N, one or both mixture of accelerine.
Phenol is 1:1.2 with the mol ratio of phosgene.
The present invention compares existing production technology, owing to using the mode of anhydrous response thing phenol spraying, anti-with phosgene
Should, under catalyst with certain temperature conditions so that the response time, by existing 7-12 hour, shortens to 3-8 hour, due to
Spray reaction enables to reactant phenol and quickly and completely reacts with phosgene, it is possible to reduce the product of by-product diphenyl carbonate
Raw, therefore further increase the purity of product phenyl chloroformate, and purity can reach 99.2%, and this reaction is also easy to
Control, the most on the whole, more shorten the time of reaction, improve purity and reaction efficiency.
Embodiment 3
First phenol is processed into molten condition standby；
Secondly above-mentioned phenol is transferred in phenol aerosol can, catalyst is transferred in catalyst spray tank, described benzene
Phenol aerosol can is arranged on the top of retort, and catalyst spray tank is arranged on the side of retort, and catalyst spray tank and benzene
The liquid outlet of phenol aerosol can bottom all connects drain pipe, and the liquid outlet of described drain pipe arranges shower nozzle, described catalyst spray tank
Shower nozzle be arranged on the middle part of retort inwall, and the middle and upper part of the shower nozzle orientating reaction tank of catalyst spray tank, described phenol
The shower nozzle of aerosol can is arranged on the top in described retort, and the middle part of retort arranges phosgene air inlet, and retort side is even
Connect circulating refrigerator；
Again first to ON cycle fridge, retort is carried out temperature and is increased to 85 DEG C, be then first passed through in retort
Phosgene, and the intake of phosgene is 1300L, and it is continually fed into phosgene, it is then turned on phenol aerosol can, opens catalyst simultaneously
Aerosol can, the response time is 3 hours, takes middle control sample, and gas phase normalizing analyzes phenyl chloroformate and Main By product diphenyl carbonate
Area percentage；
Thirdly above-mentioned middle control sample is extracted once for 20 minutes so that step 3 continues to be reacted to phenyl chloroformate with main
The area percentage of by-product diphenyl carbonate is not further added by, and now the time is 8 hours；
After finally above-mentioned retort employing nitrogen being caught up with gas, decompression distills out phenyl chloroformate.
The outside of described retort arranges chuck, and the outer wall of described retort arranges temperature control zone road, temperature control zone
Road is connected with described circulating refrigerator, and temperature controls described temperature control zone road and is positioned at the chuck of described retort, described reaction
The gas outlet of upper end connects condenser, and described retort top plugs and is equipped with thermometer.
Catalyst is 1:20 with the ratio that mass ratio is discharge rate of described phenol.
Catalyst is DMAP, N, one or both mixture of accelerine.
Phenol is 1:1.2 with the mol ratio of phosgene.
The present invention compares existing production technology, owing to using the mode of anhydrous response thing phenol spraying, anti-with phosgene
Should, under catalyst with certain temperature conditions so that the response time, by existing 7-12 hour, shortens to 3-8 hour, due to
Spray reaction enables to reactant phenol and quickly and completely reacts with phosgene, it is possible to reduce the product of by-product diphenyl carbonate
Raw, therefore further increase the purity of product phenyl chloroformate, and purity can reach 99.4%, and this reaction is also easy to
Control, the most on the whole, more shorten the time of reaction, improve purity and reaction efficiency.
Embodiment 4
First phenol is processed into molten condition standby；
Secondly above-mentioned phenol is transferred in phenol aerosol can, catalyst is transferred in catalyst spray tank, described benzene
Phenol aerosol can is arranged on the top of retort, and catalyst spray tank is arranged on the side of retort, and catalyst spray tank and benzene
The liquid outlet of phenol aerosol can bottom all connects drain pipe, and the liquid outlet of described drain pipe arranges shower nozzle, described catalyst spray tank
Shower nozzle be arranged on the middle part of retort inwall, and the middle and upper part of the shower nozzle orientating reaction tank of catalyst spray tank, described phenol
The shower nozzle of aerosol can is arranged on the top in described retort, and the middle part of retort arranges phosgene air inlet, and retort side is even
Connect circulating refrigerator；
Again first to ON cycle fridge, retort is carried out temperature and is increased to 86 DEG C, be then first passed through in retort
Phosgene, and the intake of phosgene is 1400L, and it is continually fed into phosgene, it is then turned on phenol aerosol can, opens catalyst simultaneously
Aerosol can, the response time is 3 hours, takes middle control sample, and gas phase normalizing analyzes phenyl chloroformate and Main By product diphenyl carbonate
Area percentage；
Thirdly above-mentioned middle control sample is extracted once for 20 minutes so that step 3 continues to be reacted to phenyl chloroformate with main
The area percentage of by-product diphenyl carbonate is not further added by, and now the time is 8 hours；
After finally above-mentioned retort employing nitrogen being caught up with gas, decompression distills out phenyl chloroformate.
The outside of described retort arranges chuck, and the outer wall of described retort arranges temperature control zone road, temperature control zone
Road is connected with described circulating refrigerator, and temperature controls described temperature control zone road and is positioned at the chuck of described retort, described reaction
The gas outlet of upper end connects condenser, and described retort top plugs and is equipped with thermometer.
Catalyst is 1:20 with the ratio that mass ratio is discharge rate of described phenol.
Catalyst is DMAP, N, one or both mixture of accelerine.
Phenol is 1:1.2 with the mol ratio of phosgene.
The present invention compares existing production technology, owing to using the mode of anhydrous response thing phenol spraying, anti-with phosgene
Should, under catalyst with certain temperature conditions so that the response time, by existing 7-12 hour, shortens to 3-8 hour, due to
Spray reaction enables to reactant phenol and quickly and completely reacts with phosgene, it is possible to reduce the product of by-product diphenyl carbonate
Raw, therefore further increase the purity of product phenyl chloroformate, and purity can reach 99.5%, and this reaction is also easy to
Control, the most on the whole, more shorten the time of reaction, improve purity and reaction efficiency.
Embodiment 5
First phenol is processed into molten condition standby；
Secondly above-mentioned phenol is transferred in phenol aerosol can, catalyst is transferred in catalyst spray tank, described benzene
Phenol aerosol can is arranged on the top of retort, and catalyst spray tank is arranged on the side of retort, and catalyst spray tank and benzene
The liquid outlet of phenol aerosol can bottom all connects drain pipe, and the liquid outlet of described drain pipe arranges shower nozzle, described catalyst spray tank
Shower nozzle be arranged on the middle part of retort inwall, and the middle and upper part of the shower nozzle orientating reaction tank of catalyst spray tank, described phenol
The shower nozzle of aerosol can is arranged on the top in described retort, and the middle part of retort arranges phosgene air inlet, and retort side is even
Connect circulating refrigerator；
Again first to ON cycle fridge, retort is carried out temperature and is increased to 90 DEG C, be then first passed through in retort
Phosgene, and the intake of phosgene is 1500L, and it is continually fed into phosgene, it is then turned on phenol aerosol can, opens catalyst simultaneously
Aerosol can, the response time is 3 hours, takes middle control sample, and gas phase normalizing analyzes phenyl chloroformate and Main By product diphenyl carbonate
Area percentage；
Thirdly above-mentioned middle control sample is extracted once for 20 minutes so that step 3 continues to be reacted to phenyl chloroformate with main
The area percentage of by-product diphenyl carbonate is not further added by, and now the time is 8 hours；
After finally above-mentioned retort employing nitrogen being caught up with gas, decompression distills out phenyl chloroformate.
The outside of described retort arranges chuck, and the outer wall of described retort arranges temperature control zone road, temperature control zone
Road is connected with described circulating refrigerator, and temperature controls described temperature control zone road and is positioned at the chuck of described retort, described reaction
The gas outlet of upper end connects condenser, and described retort top plugs and is equipped with thermometer.
Catalyst is 1:20 with the ratio that mass ratio is discharge rate of described phenol.
Catalyst is DMAP, N, one or both mixture of accelerine.
Phenol is 1:1.2 with the mol ratio of phosgene.
The present invention compares existing production technology, owing to using the mode of anhydrous response thing phenol spraying, anti-with phosgene
Should, under catalyst with certain temperature conditions so that the response time, by existing 7-12 hour, shortens to 3-8 hour, due to
Spray reaction enables to reactant phenol and quickly and completely reacts with phosgene, it is possible to reduce the product of by-product diphenyl carbonate
Raw, therefore further increase the purity of product phenyl chloroformate, and purity can reach 99.6%, and this reaction is also easy to
Control, the most on the whole, more shorten the time of reaction, improve purity and reaction efficiency.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all essences in the present invention
Any amendment, equivalent and the improvement etc. made within god and principle, should be included within the scope of the present invention.
Claims (5)
1. the production method of a simple efficient phenyl chloroformate, it is characterised in that: its production method comprises the following steps:
1) phenol is processed into molten condition standby；
2) being transferred in phenol aerosol can by the phenol of step 1, be transferred to by catalyst in catalyst spray tank, described phenol sprays
Mist tank is arranged on the top of retort, and catalyst spray tank is arranged on the side of retort, and catalyst spray tank and phenol spray
The liquid outlet of the tank bottoms end of mist all connects drain pipe, and the liquid outlet of described drain pipe arranges shower nozzle, the spray of described catalyst spray tank
Head is arranged on the middle part of retort inwall, and the middle and upper part of the shower nozzle orientating reaction tank of catalyst spray tank, and described phenol is sprayed
The shower nozzle of tank is arranged on the top in described retort, and the middle part of retort arranges phosgene air inlet, and retort side connects to be followed
Ring fridge；
3) first to ON cycle fridge, retort is carried out temperature and is increased to 80-90 DEG C, then in retort, be first passed through light
Gas, and the intake of phosgene is 1000-1500L, and it is continually fed into phosgene, it is then turned on phenol aerosol can, opens simultaneously and urge
Agent aerosol can, the response time is 3 hours, takes middle control sample, and gas phase normalizing analyzes phenyl chloroformate and Main By product carbonic acid two
The area percentage of phenyl ester；
4) above-mentioned middle control sample is extracted once for 20 minutes so that step 3 continues to be reacted to phenyl chloroformate and Main By product carbon
The area percentage of diphenyl phthalate is not further added by, and now the time is 8 hours；
5), after step 4 retort employing nitrogen being caught up with gas, decompression distills out phenyl chloroformate.
The production method of a kind of simple efficient phenyl chloroformate the most according to claim 1, it is characterised in that: described instead
The outside answering tank arranges chuck, and the outer wall of described retort arranges temperature control zone road, and temperature control zone road is cold with described circulation
Freezing machine to connect, temperature controls described temperature control zone road and is positioned at the chuck of described retort, the gas outlet on described retort top
Connecting condenser, described retort top plugs and is equipped with thermometer.
The production method of a kind of simple efficient phenyl chloroformate the most according to claim 1, it is characterised in that: catalyst
It is 1:20 with the ratio that the mass ratio of described phenol is discharge rate.
The production method of a kind of simple efficient phenyl chloroformate the most according to claim 1, it is characterised in that: catalyst
For DMAP, N, one or both mixture of accelerine.
The production method of a kind of simple efficient phenyl chloroformate the most according to claim 1, it is characterised in that: phenol with
The mol ratio of phosgene is 1:1.2.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610384246.2A CN105949059A (en) | 2016-05-28 | 2016-05-28 | Simple and efficient production method for phenyl chloroformate |
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| CN201610384246.2A CN105949059A (en) | 2016-05-28 | 2016-05-28 | Simple and efficient production method for phenyl chloroformate |
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| CN201610384246.2A Pending CN105949059A (en) | 2016-05-28 | 2016-05-28 | Simple and efficient production method for phenyl chloroformate |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN2204197Y (en) * | 1994-10-25 | 1995-08-02 | 上海石油化工股份有限公司 | External circulation gas-liquid reactor for ethoxylation reaction |
| CN102875418A (en) * | 2012-09-28 | 2013-01-16 | 青岛科技大学 | Method for preparing isocyanate by means of atomizing type gas-liquid two-phase phosgenation |
-
2016
- 2016-05-28 CN CN201610384246.2A patent/CN105949059A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN2204197Y (en) * | 1994-10-25 | 1995-08-02 | 上海石油化工股份有限公司 | External circulation gas-liquid reactor for ethoxylation reaction |
| CN102875418A (en) * | 2012-09-28 | 2013-01-16 | 青岛科技大学 | Method for preparing isocyanate by means of atomizing type gas-liquid two-phase phosgenation |
Non-Patent Citations (2)
| Title |
|---|
| 李佳: ""半间歇乙氧基化反应器数学模型与模拟研究"", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
| 过学军等: ""无溶剂法合成氯甲酸苯酯"", 《精细化工中间体》 * |
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