CN100415700C - Method of producing chlorobenzyl by photochlorination - Google Patents
Method of producing chlorobenzyl by photochlorination Download PDFInfo
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- CN100415700C CN100415700C CNB2006100257321A CN200610025732A CN100415700C CN 100415700 C CN100415700 C CN 100415700C CN B2006100257321 A CNB2006100257321 A CN B2006100257321A CN 200610025732 A CN200610025732 A CN 200610025732A CN 100415700 C CN100415700 C CN 100415700C
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- chlorination
- chlorine
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- chlorobenzyl
- photochlorination
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Abstract
The present invention relates to a method for producing chlorobenzyl by utilizing photochlorination process. Said method includes the following steps: using LED as light source, making chlorine gas be contacted with the material from the bottom portion of the chlorination equipment by means of distributor, under the reaction temperature of 90 deg.C-150 deg.C making chlorine gas and aromatic compound produce side-chain chlorination reaction, firstly forming monochlorobenzyl, continuously introducing chlorine gas to obtain dichlorobenzyl, finally forming trichlorobenzyl, namely the invented product.
Description
Technical field
The present invention relates to the photochemically reactive chemical technique technology of a kind of utilization, relate in particular to a kind of method of producing benzyl chloride, particularly a kind of method that in aromatic hydrocarbons side chain chlorination process, causes optical chlorinating reaction production benzyl chloride with ultraviolet catalytic with the light chloridization process.
Background technology
The chlorination of aromatic hydrocarbons side chain is a type free radical reaction in the presence of illumination, heating or initiator, technical two classes that are divided into, one class is to be the catalytic chlorination of initiator with the superoxide, and peroxide catalyst commonly used has: dibenzoyl peroxide, Diisopropyl azodicarboxylate etc.; Another kind of is to utilize UV-light to come catalysis to cause chlorination reaction.Chlorination reactor is based on glass-lined kettle formula reactor.The chlorination of aromatic hydrocarbons side chain is mainly used in intermediates such as producing a benzyl chloride, benzyl dichloride, three benzyl chlorides, and in order to produce compounds such as aromatic alcohol, aldehyde, acid, acyl chlorides, therefore, the effect of this technology in organic synthesis is very big then.
Usually, the illumination initiating chamical reaction is to use UV-irradiation the most favourable, because the energy of UV-light is higher, help efficiently to cause free radical, so in industrial production, the normal fluorescent light source that is rich in UV-light that adopts is shone, its wavelength region is between 400～700nm.The existence of impurity in the raw material, very big to aromatic hydrocarbons side chain chlorination influence, usually can cause upward chlorination of ring, thereby can not get desired product.
In prior art, " fine chemistry industry " Vol.22, No.12 have reported " light chlorination process is made adjacent cyano group benzyl chloride pilot process research ", and result of study shows: illumination can improve optical chlorinating reaction speed greatly, shortens the reaction times; Because blue light has very strong penetrance, so speed of response is the fastest under blue light illumination, other as the catalytic effect of light sources such as fluorescent lamp, incandescent light, ultraviolet lamp much at one.The pilot scale chlorination plant is a 300L slender type enamel reaction still, and illumination system is selected the Glass tubing of the diameter 108mm of one one end closure for use, is fixed on reactor and covers, and the illumination of 3 100W incandescent light is incorporated in the reaction solution, and light chlorination effect is fine.Because being reflected at about 150 ℃ of temperature carries out, general ultraviolet lamp, blue-ray light and daylight etc. all hold can't stand long high temperature, and therefore, incandescent light is suitable light source.This method is domestic method relatively more commonly used at present, and its main drawback is that light chlorination plant volume is restricted, and single complete equipment throughput is restricted; Light source power is bigger, and the efficiency of light energy utilization is lower; Light source life is shorter.
United States Patent (USP) (US.5514254,1996) discloses a kind of alkyl aromatic compound side chain light chlorating production method.Used optical chlorinating reaction device is a kind of tubular reactor of length.The length-to-diameter of reactor can reach 50: 1, and reactor has one or several window, and the window of reactor can see through radiant light.Reactor by the material manufacturing that can see through radiant light or at least near the part of light source by the material manufacturing that can see through radiant light.No any mechanical stirring device in the reactor.Light source is contained in the outside of reactor window.Light source is used mercuryarc lamp (high pressure, middle pressure, low pressure) or xenon lamp usually.The light of this lamp emission is in the ultraviolet scope, and its wavelength of light that the light chlorination is used is 150～600nm, is preferably 300～400nm.Alkyl aromatic compound passes through pump, send into the bottom of optical chlorinating reaction device continuously from material container through pipeline, chlorine is then also delivered to optical chlorinating reaction device bottom continuously through another pipeline, and alkyl aromatic compound mixes the mixture that forms homogeneous with chlorine in static mixer.The ratio of used chlorine and alkyl aromatic compound should make chlorine leach or be dissolved in substantially in the liquid phase of optical chlorinating reaction device ingress, perhaps should be evenly dispersed in the liquid phase of optical chlorinating reaction device ingress at least, to guarantee that optical chlorinating reaction carries out, and avoids the formation of explosive mixture.The concentration of chlorine in the homogeneous liquid phase is substantially: per 100 weight part alkyl aromatic compounds, 0.1～1 weight part chlorine.The uniform mixture of alkyl aromatic compound and chlorine enters the optical chlorinating reaction device by static mixer and carries out optical chlorinating reaction.In the optical chlorinating reaction device, the velocity of flow of reaction mixture is 0.5～2 meter per second.The temperature at reactor inlet place is 0 ℃～150 ℃, and the temperature head in reactor inlet place and exit remains on 1 ℃～35 ℃.Reaction mixture is adjusted by heat exchanger in the temperature at reactor inlet place.In reactor, reaction mixture issues third contact of a total solar or lunar eclipse chlorination reaction in UV-irradiation, and chlorine falls or almost completely consumes in reactor planted agent completely consumed.The hydrogen chloride gas that produces through light chlorating reaction mixture and reaction is shifted out by reactor head, and sends material container back to through special pipeline, here, and hydrogen chloride gas and liquid phase separation, and discharge by suitable pipeline by heat exchanger.Reaction heat effect is controlled through heat exchanger by continuous round-robin material in the container, and this heat effect also can be controlled by the heat exchanger that is positioned on each pipeline.The optical chlorinating reaction device can also can be one another in series or parallel connection by two or more optical chlorinating reaction devices only with one.Reaction mixture is a continuous round-robin between optical chlorinating reaction device and container, circulation each time in the optical chlorinating reaction device, and the side chain of alkyl aromatic compound has all carried out once part chlorination, and reaction mixture round-robin number of times depends on needs the chlorating degree.
This method is a continuous light chlorating method, the production efficiency height, and operation control is flexibly; But production process needs power consumption, the equipment complexity, and light source is with mercuryarc lamp or xenon lamp, and the efficiency of light energy utilization is low, and light source life is shorter.
Summary of the invention
The present invention is intended to overcome defectives such as the used light source power consumption of traditional light chloridization process is big, the efficiency of light energy utilization is low, light source life is short, the method for the producing chlorobenzyl by photochlorination that provide that a kind of current consumption is low, the light source thermal value is little, reduced investment, by product can be fully used.
The present invention realizes like this, it is characterized in that adopting photodiode (LED) to be the ultraviolet source of initiation reaction, under the irradiation of this light source, chlorine contacts with material by divider from the chlorination plant bottom, under 90 ℃～150 ℃ temperature of reaction, chlorine and aromatics generation side-chain chlorination, the reaction beginning generates a benzyl chloride earlier, continue logical chlorine and obtain benzyl dichloride, generate three benzyl chlorides at last, the hydrogenchloride that reaction produces and a spot of chlorine obtain byproduct hydrochloric acid and clorox through water and liquid caustic soda absorption respectively.
The principle of smooth chlorination method of the present invention is: chlorine molecular absorption luminous energy and being activated, and be in the chlorine molecule covalent linkage fracture of excited state and produce free radical, free radical attack reactant molecule, and regenerate a new free radical, circulation repeatedly; Release energy the back from combining reaction terminating until collisions such as free radical and walls.
R-CH
3+Cl·→R-CH
2·+HCl
Cl-Cl+R-CH
2·→Cl·+R-CH
2Cl
Cl·+Cl·→Cl
2
R-CH
2·+Cl·→R-CH
2Cl
According to the method described in the present invention, used photodiode (LED), its wavelength region is: 300nm～600nm, the optimized wavelength scope is 450nm ± 50nm; Photodiode (LED) light source can be single or multiple compositions, and power range is: 0.1W～1000W.Used chlorination plant can be tower or still formula structure, and the former has the visor hole on the body of the tower, and 1～30 of quantity, the material of glass visor are toughened glass or silica glass; The latter stretches in the still by kettle cover with quartz glass tube, and photodiode (LED) is installed in the quartz glass tube, and quartz glass tube quantity is 1～30.Chlorination plant design has chuck, can be with steam or cooling water control temperature of charge.The UV-light that photodiode (LED) produces by the chlorination Tata on one's body the glass visor or the silica tube in the still formula equipment shine material, initiation reaction.
Aromatics in the chlorination plant heats up by jacket steam temperature is reached more than 90 ℃, chlorine contacts with material by divider from the chlorination plant bottom, under illumination condition, chlorine and aromatics generation side-chain chlorination, temperature of reaction maintains 90 ℃～150 ℃, and the reaction beginning generates a benzyl chloride earlier, continues logical chlorine and obtains benzyl dichloride, generate three benzyl chlorides at last, obtain product.Described divider material is a tetrafluoroethylene.The hydrogenchloride that reaction produces and a spot of chlorine are made byproduct hydrochloric acid and clorox through water and liquid caustic soda absorption respectively.
The present invention compared with prior art has the following advantages:
1. the present invention substitutes light sources such as original ultraviolet lamp, mercury lamp, high-pressure mercury lamp, blue-ray light with photodiode (LED), has improved the utilization ratio of luminous energy greatly, and light chlorination power consumption is reduced.
2. because photodiode (LED) thermal value is very low, need not to remove heat with the freezing air that does not have oil, reduced the power consumption of off-set facility equally, comprehensive energy consumption is lower.
3. photodiode (LED) has long work-ing life, can reach more than 100,000 hours generally speaking, is much higher than other light sources, reduces investment outlay.
4. light source is by glass visor irradiation material, and the chlorating security significantly improves.
Embodiment
Come the present invention is further described in detail with some embodiment below, but the present invention is in no way limited to these embodiment.
Embodiment 1
The light source that the initiation optical chlorinating reaction is used is to be assembled by 355 photodiodes (LED).Photo-chlorination device mainly is made of following equipment: chlorination tower, tail gas condenser, tail gas absorber, absorption liquid circulation groove, recycle pump, by-product hydrochloric acid and clorox storage tank etc.
In the chlorination tower, drop into 6.5 tons of toluene, open chlorination tower jacket steam valve, make the interior material of tower be warming up to 90 ℃, open the switch of photodiode (LED) light source, under illumination condition, open the chlorine pipeline valve, chlorine contacts with material by divider from the chlorination tower bottom through under meter side-chain chlorination takes place, and regulates chlorination tower jacket steam or cooling water valve, makes temperature of reaction maintain 90 ℃～150 ℃, the reaction beginning generates a benzyl chloride earlier, continue logical chlorine and obtain benzyl dichloride, generate three benzyl chlorides (trichlorotoluene zotrichloride) at last, constantly detect the composition of chloride material, when the benzyl dichloride content in the chloride material less than 0.5% the time, stop logical chlorine, and remove a small amount of hydrogenchloride and the chlorine that is dissolved in the material, open chlorination tower chuck cooling water valve again with nitrogen, make the interior material of tower be cooled to 35 ℃, obtain the trichlorotoluene zotrichloride product.
The tail gas that the side chain chlorination produces mainly contains hydrogenchloride, a spot of chlorine and organic matters steam, this tail gas is through tail gas condenser, most of organic steam obtains condensation and is back to the chlorination tower continuing reaction, the tail gas that removes behind most of organism passes through tail gas absorber again, makes byproduct hydrochloric acid and clorox respectively.
Embodiment 2
Photo-chlorination device is with embodiment 1.In the chlorination tower, drop into 7.5 tons of parachlorotoluenes, open chlorination tower jacket steam valve, make the interior material of tower be warming up to 90 ℃, open the switch of photodiode (LED) light source, under illumination condition, open the chlorine pipeline valve, chlorine contacts with material by divider from the chlorination tower bottom through under meter side-chain chlorination takes place, regulate chlorination tower jacket steam or cooling water valve, make temperature of reaction maintain 90 ℃～150 ℃, paired chlorine one benzyl chloride of reaction Mr. beginning, continue logical chlorine and obtain, generate at last, constantly detect the composition of chloride material chlorine three benzyl chlorides (to chlorobenzotrichloride) to the chlorine benzyl dichloride, when in the chloride material to chlorine benzyl dichloride content less than 0.5% the time, stop logical chlorine, and remove a small amount of hydrogenchloride and the chlorine that is dissolved in the material, open chlorination tower chuck cooling water valve again with nitrogen, make the interior material of tower be cooled to 35 ℃, obtain the chlorobenzotrichloride product.
The tail gas that the side chain chlorination produces mainly contains hydrogenchloride, a spot of chlorine and organic matters steam, this tail gas is through tail gas condenser, most of organic steam obtains condensation and is back to the chlorination tower continuing reaction, the tail gas that removes behind most of organism passes through tail gas absorber again, makes byproduct hydrochloric acid and clorox respectively.
Embodiment 3
Photo-chlorination device is with embodiment 1.In the chlorination tower, drop into 6.0 tons of m-xylenes, open chlorination tower jacket steam valve, make the interior material of tower be warming up to 95 ℃, open the switch of photodiode (LED) light source, under illumination condition, open the chlorine pipeline valve, chlorine contacts with material by divider from the chlorination tower bottom through under meter side-chain chlorination takes place, regulate chlorination tower jacket steam or cooling water valve, make temperature of reaction maintain 95 ℃～150 ℃, 21 benzyl chlorides between the reaction beginning generates earlier, continue logical chlorine obtain between two benzyl dichlorides, two or three benzyl chlorides (two trichlorotoluene zotrichloride) between generating at last constantly detect the composition of chloride material, two benzyl dichloride content are less than 0.8% the time between in the chloride material, stop logical chlorine, and remove a small amount of hydrogenchloride and the chlorine that is dissolved in the material, open chlorination tower chuck cooling water valve again with nitrogen, make the interior material of tower be cooled to 45 ℃, two trichlorotoluene zotrichloride products between obtaining.
The tail gas that the side chain chlorination produces mainly contains hydrogenchloride, a spot of chlorine and organic matters steam, this tail gas is through tail gas condenser, most of organic steam obtains condensation and is back to the chlorination tower continuing reaction, the tail gas that removes behind most of organism passes through tail gas absorber again, makes byproduct hydrochloric acid and clorox respectively.
Embodiment 4
The light source that the initiation optical chlorinating reaction is used is to be assembled by 100 photodiodes (LED), and light source is installed in the quartz glass tube, and quartz glass tube stretches in the chlorination tank by kettle cover, constitutes chlorination tank thus.The overall optical chloridizing unit mainly is made of following equipment: chlorination tank, tail gas condenser, tail gas absorber, absorption liquid circulation groove, recycle pump, by-product hydrochloric acid and clorox storage tank etc.
In 1000 liters of chlorination tanks, drop into 0.8 ton of toluene, open chlorination tank jacket steam valve, make the interior material of still be warming up to 90 ℃, open the switch of photodiode (LED) light source, under illumination condition, open the chlorine pipeline valve, chlorine contacts with material by divider from the chlorination tower bottom through under meter side-chain chlorination takes place, and regulates chlorination tank jacket steam or cooling water valve, makes temperature of reaction maintain 90 ℃～150 ℃, the reaction beginning generates a benzyl chloride earlier, continue logical chlorine and obtain benzyl dichloride, generate three benzyl chlorides (trichlorotoluene zotrichloride) at last, constantly detect the composition of chloride material, when the benzyl dichloride content in the chloride material less than 0.5% the time, stop logical chlorine, and remove a small amount of hydrogenchloride and the chlorine that is dissolved in the material, open chlorination tank chuck cooling water valve again with nitrogen, make the interior material of still be cooled to 35 ℃, obtain the trichlorotoluene zotrichloride product.
The tail gas that the side chain chlorination produces mainly contains hydrogenchloride, a spot of chlorine and organic matters steam, this tail gas is through tail gas condenser, most of organic steam obtains condensation and is back to continuing reaction in the chlorination tank, the tail gas that removes behind most of organism passes through tail gas absorber again, makes byproduct hydrochloric acid and clorox respectively.
Claims (7)
1. the method for a producing chlorobenzyl by photochlorination, it is characterized in that adopting photodiode is the ultraviolet source of initiation reaction, under the irradiation of this light source, chlorine contacts with material by divider from the chlorination plant bottom, under 90 ℃～150 ℃ temperature of reaction, chlorine and aromatics generation side-chain chlorination, the reaction beginning generates a benzyl chloride earlier, continue logical chlorine and obtain benzyl dichloride, generate three benzyl chlorides at last, the hydrogenchloride that reaction produces and a spot of chlorine obtain byproduct hydrochloric acid and clorox through water and liquid caustic soda absorption respectively.
2. the method for producing chlorobenzyl by photochlorination according to claim 1, it is characterized in that its wavelength region of described photodiode is: 300nm～600nm, can be made up of single or multiple photodiodes as the light source that causes chlorination reaction, power range is: 0.1W～1000W.
3. the method for producing chlorobenzyl by photochlorination according to claim 1 and 2 is characterized in that, described photodiode wavelength region is: 450nm ± 50nm.
4. the method for producing chlorobenzyl by photochlorination according to claim 1 is characterized in that described chlorination plant designs the chuck of useful steam or cooling water control temperature of charge.
5. according to the method for claim 1 or 4 described producing chlorobenzyl by photochlorination, it is characterized in that described chlorination plant has tower structure, have glass visor hole on the body of the tower, 1～30 of quantity, the material of glass visor is toughened glass or silica glass, and the UV-light that photodiode produces is by the irradiation of the glass visor on body of the tower material.
6. according to the method for claim 1 or 4 described producing chlorobenzyl by photochlorination, it is characterized in that described chlorination plant has still formula structure, quartz glass tube stretches in the still by kettle cover, and photodiode is installed in the quartz glass tube, and quartz glass tube quantity is 1～30.
7. according to the method for claim 1 or 4 described producing chlorobenzyl by photochlorination, it is characterized in that chlorine feeds by the chlorine divider from the chlorination plant bottom, the divider material is a tetrafluoroethylene.
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| CNB2006100257321A CN100415700C (en) | 2006-04-14 | 2006-04-14 | Method of producing chlorobenzyl by photochlorination |
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| CNB2006100257321A CN100415700C (en) | 2006-04-14 | 2006-04-14 | Method of producing chlorobenzyl by photochlorination |
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| CN102060654B (en) * | 2011-01-10 | 2013-06-12 | 武汉理工大学 | Method for selective chlorination of alkyl side chains on benzene ring |
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| CN102911009B (en) * | 2012-10-29 | 2015-08-19 | 浙江巍华化工有限公司 | A kind of continuous light causes the industrial method of chlorination reaction synthesis to chlorine three benzyl chloride |
| JP6311946B2 (en) * | 2013-09-13 | 2018-04-18 | ファイニングス シーオー． エルティーディーＦｉｎｉｎｇｓ Ｃｏ． Ｌｔｄ | Method for preparing trichloromethyl substituted benzene |
| CN104447188B (en) * | 2013-09-13 | 2016-05-11 | 上海方纶新材料科技有限公司 | The preparation method of a kind of two (trichloromethyl) benzene and two (chloroformyl) benzene |
| CN104447298B (en) * | 2014-12-12 | 2016-03-30 | 山东凯盛新材料有限公司 | The preparation method of Benzoyl chloride |
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| CN104387263A (en) * | 2014-12-12 | 2015-03-04 | 山东凯盛新材料有限公司 | Synthesis process of isophthaloyl dichloride |
| CN104592000B (en) * | 2014-12-22 | 2017-01-11 | 上海方纶新材料科技有限公司 | Cleaning process of preparing chloroformyl substituted benzene |
| CN105294391B (en) * | 2015-12-14 | 2017-08-08 | 山东凯盛新材料股份有限公司 | Between benzyl dichloride synthesis technique |
| CN105294392B (en) * | 2015-12-14 | 2017-08-25 | 山东凯盛新材料股份有限公司 | To the preparation method of benzyl dichloride |
| CN105348036B (en) * | 2015-12-14 | 2017-08-25 | 山东凯盛新材料股份有限公司 | To the continuous production processes and device of benzyl dichloride |
| CN105384595B (en) * | 2015-12-14 | 2017-06-20 | 山东凯盛新材料股份有限公司 | To the synthesis technique of benzyl dichloride |
| CN105503516B (en) * | 2015-12-14 | 2018-03-23 | 山东凯盛新材料股份有限公司 | Between benzyl dichloride continuous production processes and device |
| CN105384597B (en) * | 2015-12-14 | 2017-06-20 | 山东凯盛新材料股份有限公司 | Between benzyl dichloride preparation method |
| CN109776255B (en) * | 2019-02-26 | 2021-12-07 | 南京工业大学 | Method for preparing 2, 6-dichlorobenzylidene dichloride by low-temperature photochlorination method |
| CN113173831B (en) * | 2021-04-08 | 2024-01-19 | 宜都市友源实业有限公司 | Production system and process for continuous chlorination of trichlorotoluene |
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