CN109293483A - A method of Chlorphenesin is prepared using microchannel continuous flow reactor - Google Patents
A method of Chlorphenesin is prepared using microchannel continuous flow reactor Download PDFInfo
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- CN109293483A CN109293483A CN201811439196.9A CN201811439196A CN109293483A CN 109293483 A CN109293483 A CN 109293483A CN 201811439196 A CN201811439196 A CN 201811439196A CN 109293483 A CN109293483 A CN 109293483A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
It is disclosed by the invention to belong to technical field of organic chemistry, specially a kind of method that Chlorphenesin is prepared using microchannel continuous flow reactor, this kind using microchannel continuous flow reactor prepare Chlorphenesin method specific steps are as follows: a) by chlorophenol and 3- chloro- 1, in methanol mixed solution and liquid methanol sodium solution the injection microchannel continuous flow reactor of 2- propylene glycol, it is stopped 30-120 seconds at 40-100 DEG C, carries out etherification reaction；B) reaction solution obtains product after cooling, centrifugation, concentration, recrystallization, and this method is compared with the traditional method, and entire reaction process is simple and efficient, and securely and reliably, total recovery can achieve 90%, and product purity reaches 99.5% or more, effectively improves production efficiency.
Description
Technical field
The present invention relates to technical field of organic chemistry, it is sweet that specially a kind of use microchannel continuous flow reactor prepares chlorobenzene
The method of ether.
Background technique
Chlorphenesin is a kind of fine chemistry product, and in terms of the medicine and in terms of cosmetics, Chlorphenesin is anti-as antibacterial
Rotten agent, being all made of parachlorophenol and 3- chlorine-1,2-propylene glycol both at home and abroad at present is starting material, is contracted by the effect of alkali
Product is closed, such as parachlorophenol, 3- chlorine-1,2-propylene glycol, sodium hydroxide flows back 3-6 hours in ethanol solution to react, firstly, instead
It answers highly exothermic, traditional still reaction heat exchange area small, there is security risk, secondary response generates water, and water can not only prevent instead
The progress answered also will cause 3- chlorine-1,2-propylene glycol and be hydrolyzed to glycerine, therefore feed stock conversion is lower than 90%, and generate compared with
More waste liquid, for this purpose, a kind of it is proposed that method for preparing Chlorphenesin using microchannel continuous flow reactor.
Summary of the invention
The purpose of the present invention is to provide a kind of methods for preparing Chlorphenesin using microchannel continuous flow reactor, with solution
Parachlorophenol and the 3- chlorine-1,2-propylene glycol certainly mentioned above in the background art of being all made of both at home and abroad at present leads to for starting material
The effect of alkali is crossed to obtain condensation product, such as parachlorophenol, 3- chlorine-1,2-propylene glycol, sodium hydroxide flows back in ethanol solution
It reacts within 3-6 hours, firstly, reaction is highly exothermic, traditional still reaction heat exchange area is small, there is security risk, and secondary response produces
Unboiled water, water can not only prevent the progress of reaction, also will cause 3- chlorine-1,2-propylene glycol and are hydrolyzed to glycerine, therefore raw material converts
Rate is lower than 90%, and leads to the problem of more waste liquid.
To achieve the above object, the invention provides the following technical scheme: a kind of prepared using microchannel continuous flow reactor
The method of Chlorphenesin, this kind use microchannel continuous flow reactor prepare the concrete operation step of the method for Chlorphenesin such as
Under:
A) the 3- chlorine-1,2-propylene glycol of the chlorophenol of 0.8-1mol and 1-1.2mol is put into the volumetric flask A for being 1L to volume,
The methanol stirring and dissolving of 480-520ml is added, after being completely dissolved, methanol constant volume is added again to 1L, by the liquid of 1-1.2mol30%
Body sodium methoxide is added in the volumetric flask B of 500ml, and with methanol constant volume to 500ml, volumetric flask A is accessed using constant flow pump micro-
On the continuous flow reactor of channel, flow velocity is adjusted to 1-1.2ml/ seconds, volumetric flask B is accessed into microchannel continuous flow using constant flow pump
On reactor, flow velocity is adjusted to 0.4-0.6ml/ seconds, temperature is set in 40-100 DEG C, etherification reaction is carried out, is connect with flask
It receives reaction solution and obtains semi-finished product A；
B) standing of semi-finished product A obtained in step a) is naturally cooled to 0-30 DEG C, semi-finished product A after cooling is placed into centrifugation
In machine, total power opens centrifuge 20-35min, removes the solid sodium chloride in semi-finished product A, after removal solid sodium chloride
Semi-finished product A is heated, and the liquid in semi-finished product A is evaporated, and is added the three of 839-845g to being evaporated in the semi-finished product A after liquid
Chloromethanes recrystallization, filtered, dry after obtain Chlorphenesin finished product.
Preferably, microchannel continuous flow reactor adjusts the flows of reaction raw materials by metering pump in the step a),
Microchannel continuous flow reactor controls temperature by heat exchanger.
Preferably, the reaction time is 30-120 seconds in the step a).
Compared with prior art, the beneficial effects of the present invention are: this method is compared with the traditional method, entire reaction process letter
Single efficient, securely and reliably, total recovery can achieve 90%, and product purity reaches 99.5% or more, effectively improve production efficiency.
Detailed description of the invention
Fig. 1 is reaction process schematic diagram of the present invention.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
Referring to Fig. 1, the present invention provides a kind of technical solution: a kind of using microchannel continuous flow reactor, to prepare chlorobenzene sweet
The method of ether, this kind using microchannel continuous flow reactor prepare Chlorphenesin method specific steps are as follows:
A) the 3- chlorine-1,2-propylene glycol of the chlorophenol of 0.8-1mol and 1-1.2mol is put into the volumetric flask A for being 1L to volume,
The methanol stirring and dissolving of 480-520ml is added, after being completely dissolved, methanol constant volume is added again to 1L, by the liquid of 1-1.2mol30%
Body sodium methoxide is added in the volumetric flask B of 500ml, and with methanol constant volume to 500ml, volumetric flask A is accessed using constant flow pump micro-
On the continuous flow reactor of channel, flow velocity is adjusted to 1-1.2ml/ seconds, volumetric flask B is accessed into microchannel continuous flow using constant flow pump
On reactor, flow velocity is adjusted to 0.4-0.6ml/ seconds, temperature is set in 40-100 DEG C, etherification reaction is carried out, is connect with flask
It receives reaction solution and obtains semi-finished product A；
B) standing of semi-finished product A obtained in step a) is naturally cooled to 0-30 DEG C, semi-finished product A after cooling is placed into centrifugation
In machine, total power opens centrifuge 20-35min, removes the solid sodium chloride in semi-finished product A, after removal solid sodium chloride
Semi-finished product A is heated, and the liquid in semi-finished product A is evaporated, and is added the three of 839-845g to being evaporated in the semi-finished product A after liquid
Chloromethanes recrystallization, filtered, dry after obtain Chlorphenesin finished product.
Wherein, microchannel continuous flow reactor adjusts the flows of reaction raw materials by metering pump in the step a), micro-
Channel continuous flow reactor controls temperature by heat exchanger, and the reaction time is 30-120 seconds in the step a).
Embodiment one
A) the 3- chlorine-1,2-propylene glycol of the chlorophenol of 1mol and 1.02mol is put into the volumetric flask A for being 1L to volume, is added
After being completely dissolved, methanol constant volume is added to 1L, by the liquid methanol sodium of 1.02mol30% in the methanol stirring and dissolving of 500ml again
It is added in the volumetric flask B of 500ml, and with methanol constant volume to 500ml, volumetric flask A is accessed into the bold and generous machine in Shandong using constant flow pump
On the microchannel continuous flow reactor of tool Science and Technology Ltd. production, flow velocity is adjusted to 1ml/ seconds, volumetric flask B is used into constant current
On the microchannel continuous flow reactor of pump access Haomai Mechanical Science & Technology Co., Ltd., Shandong Prov production, flow velocity is adjusted to 0.6ml/
Second, temperature is set in 60 DEG C, carries out etherification reaction, reaction solution is received with flask and obtains semi-finished product A；
B) standing of semi-finished product A obtained in step a) is naturally cooled to 30 DEG C, semi-finished product A after cooling is placed into centrifuge
Interior, total power opens centrifuge 20min, removes the solid sodium chloride in semi-finished product A, by the semi-finished product after removal solid sodium chloride
A is heated, and the liquid in semi-finished product A is evaporated, and is tied again to the chloroform that 839g is added in the semi-finished product A after liquid is evaporated
Crystalline substance, filtered, dry after obtain Chlorphenesin finished product.
Reach 99.5% by Chlorphenesin finished product content prepared by the above method, molar yield reaches 96%.
Embodiment two
A) the 3- chlorine-1,2-propylene glycol of the chlorophenol of 1mol and 1.02mol is put into the volumetric flask A for being 1L to volume, is added
The methanol stirring and dissolving of 505ml after being completely dissolved, is added methanol constant volume to 1L again, the liquid methanol sodium of 1mol30% is added
Into the volumetric flask B of 500ml, and with methanol constant volume to 500ml, volumetric flask A is accessed into the bold and generous mechanical division in Shandong using constant flow pump
On the microchannel continuous flow reactor of skill Co., Ltd production, flow velocity is adjusted to 1.2ml/ seconds, volumetric flask B is used into constant flow pump
It accesses on the microchannel continuous flow reactor of Haomai Mechanical Science & Technology Co., Ltd., Shandong Prov's production, flow velocity is adjusted to 0.6ml/ seconds,
Temperature is set in 500 DEG C, carries out etherification reaction, reaction solution is received with flask and obtains semi-finished product A；
B) standing of semi-finished product A obtained in step a) is naturally cooled to 30 DEG C, semi-finished product A after cooling is placed into centrifuge
Interior, total power opens centrifuge 25min, removes the solid sodium chloride in semi-finished product A, by the semi-finished product after removal solid sodium chloride
A is heated, and the liquid in semi-finished product A is evaporated, and is tied again to the chloroform that 840g is added in the semi-finished product A after liquid is evaporated
Crystalline substance, filtered, dry after obtain Chlorphenesin finished product.
Reach 99.6% by Chlorphenesin finished product content prepared by the above method, molar yield reaches 95.5%.
Embodiment three
A) the 3- chlorine-1,2-propylene glycol of the chlorophenol of 1mol and 1.2mol is put into the volumetric flask A for being 1L to volume, is added
The methanol stirring and dissolving of 520ml after being completely dissolved, is added methanol constant volume to 1L again, the liquid methanol sodium of 1mol30% is added
It is into the volumetric flask B of 500ml, and with methanol constant volume to 500ml, volumetric flask A is raw using constant flow pump access Corning Incorporated
On the continuous flow reactor of production, flow velocity is adjusted to 1.2ml/ seconds, volumetric flask B is raw using constant flow pump access Corning Incorporated
On the microchannel continuous flow reactor of production, flow velocity is adjusted to 0.4ml/ seconds, temperature is set in 700 DEG C, carries out etherification reaction,
Reaction solution, which is received, with flask obtains semi-finished product A；
B) standing of semi-finished product A obtained in step a) is naturally cooled to 25 DEG C, semi-finished product A after cooling is placed into centrifuge
Interior, total power opens centrifuge 30min, removes the solid sodium chloride in semi-finished product A, by the semi-finished product after removal solid sodium chloride
A is heated, and the liquid in semi-finished product A is evaporated, and is tied again to the chloroform that 845g is added in the semi-finished product A after liquid is evaporated
Crystalline substance, filtered, dry after obtain Chlorphenesin finished product.
Reach 99.7% by Chlorphenesin finished product content prepared by the above method, molar yield reaches 95%.
It although an embodiment of the present invention has been shown and described, for the ordinary skill in the art, can be with
A variety of variations, modification, replacement can be carried out to these embodiments without departing from the principles and spirit of the present invention by understanding
And modification, the scope of the present invention is defined by the appended.
Claims (3)
1. a kind of method for preparing Chlorphenesin using microchannel continuous flow reactor, it is characterised in that: this kind uses microchannel
Continuous flow reactor prepare the method for Chlorphenesin specific steps are as follows:
The 3- chlorine-1,2-propylene glycol of the chlorophenol of 0.8-1mol and 1-1.2mol is put into the volumetric flask A for being 1L to volume, is added
After being completely dissolved, methanol constant volume is added to 1L, by the liquid of 1-1.2mol30% in the methanol stirring and dissolving for entering 480-520ml again
Sodium methoxide is added in the volumetric flask B of 500ml, and with methanol constant volume to 500ml, volumetric flask A is accessed using constant flow pump micro- logical
On road continuous flow reactor, flow velocity is adjusted to 1-1.2ml/ seconds, volumetric flask B is anti-using constant flow pump access microchannel continuous flow
It answers on device, flow velocity is adjusted to 0.4-0.6ml/ seconds, temperature is set in 40-100 DEG C, etherification reaction is carried out, is received with flask
Reaction solution obtains semi-finished product A；
The standing of semi-finished product A obtained in step a) is naturally cooled to 0-30 DEG C, semi-finished product A after cooling is placed into centrifuge
Interior, total power opens centrifuge 20-35min, removes the solid sodium chloride in semi-finished product A, by half after removal solid sodium chloride
Finished product A is heated, and the liquid in semi-finished product A is evaporated, to being evaporated the trichlorine that 839-845g is added in the semi-finished product A after liquid
Methane recrystallization, filtered, dry after obtain Chlorphenesin finished product.
2. a kind of method for preparing Chlorphenesin using microchannel continuous flow reactor according to claim 1, feature
Be: microchannel continuous flow reactor adjusts the flow of reaction raw materials by metering pump in the step a), and microchannel is continuous
Flow reactor controls temperature by heat exchanger.
3. a kind of method for preparing Chlorphenesin using microchannel continuous flow reactor according to claim 1, feature
Be: the reaction time is 30-120 seconds in the step a).
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811439196.9A CN109293483A (en) | 2018-11-29 | 2018-11-29 | A method of Chlorphenesin is prepared using microchannel continuous flow reactor |
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| CN201811439196.9A CN109293483A (en) | 2018-11-29 | 2018-11-29 | A method of Chlorphenesin is prepared using microchannel continuous flow reactor |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111056928A (en) * | 2019-12-30 | 2020-04-24 | 陕西省石油化工研究设计院 | Method for synthesizing chlorphenesin |
| CN111302985A (en) * | 2020-04-15 | 2020-06-19 | 沈阳感光化工研究院有限公司 | Method for synthesizing 4-hydroxy-4' -isopropoxy-diphenyl sulfone compound by microchannel reactor |
| CN113979841A (en) * | 2021-11-17 | 2022-01-28 | 华阳新材料科技集团有限公司 | Method for continuously producing chlorphenesin |
| WO2023070907A1 (en) * | 2021-10-28 | 2023-05-04 | 台州学院 | Etherification method for halogenated phenol |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105016989A (en) * | 2015-08-18 | 2015-11-04 | 北京桑普生物化学技术有限公司 | Synthetic method of chlorobenzene glyceryl ether |
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2018
- 2018-11-29 CN CN201811439196.9A patent/CN109293483A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105016989A (en) * | 2015-08-18 | 2015-11-04 | 北京桑普生物化学技术有限公司 | Synthetic method of chlorobenzene glyceryl ether |
Non-Patent Citations (2)
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| 穆金霞 等: ""微通道反应器在合成反应中的应用"", 《化学进展》 * |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111056928A (en) * | 2019-12-30 | 2020-04-24 | 陕西省石油化工研究设计院 | Method for synthesizing chlorphenesin |
| CN111302985A (en) * | 2020-04-15 | 2020-06-19 | 沈阳感光化工研究院有限公司 | Method for synthesizing 4-hydroxy-4' -isopropoxy-diphenyl sulfone compound by microchannel reactor |
| CN111302985B (en) * | 2020-04-15 | 2021-11-12 | 沈阳感光化工研究院有限公司 | Method for synthesizing 4-hydroxy-4' -isopropoxy-diphenyl sulfone compound by microchannel reactor |
| WO2023070907A1 (en) * | 2021-10-28 | 2023-05-04 | 台州学院 | Etherification method for halogenated phenol |
| CN113979841A (en) * | 2021-11-17 | 2022-01-28 | 华阳新材料科技集团有限公司 | Method for continuously producing chlorphenesin |
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Application publication date: 20190201 |