CN104744306A - P-chloroaniline isocyanate preparation method - Google Patents
P-chloroaniline isocyanate preparation method Download PDFInfo
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Abstract
The invention relates to a p-chloroaniline isocyanate preparation method comprising the following steps: (1) p-chloroaniline hydrochloride is synthesized, wherein p-chloroaniline is adopted as a raw material and is subjected to a reaction with hydrochloric acid in an organic solvent, such that p-chloroaniline hydrochloride is synthesized; (2) p-chloroaniline isocyanate is synthesized, wherein p-chloroaniline hydrochloride and triphosgene are adopted as raw material, and p-chloroaniline isocyanate is synthesized in an organic solvent. The method provided by the invention has the advantages of advanced process route, reasonable process conditions, and high reaction yield. The materials used in production are not highly excessive; solvent dose in each step is low; and the solvent can be directly used without treatment. An intermediate is not needed to be dried, and can be directly used in the next step of reaction. Three-waste amount is low, and the waste is easy to treat. Therefore, the method has good implementation value and social benefit.
Description
Technical field
The present invention relates to basic chemical industry field, particularly a kind of preparation method of parachlorobenzyl isocyanic ester.
Background technology
Parachlorobenzyl isocyanic ester is important medicine, agricultural chemicals and macromolecular material intermediate.Parachlorobenzyl isocyanic ester synthesis is main adopts p-Chlorobenzoic acid amide photoreactive gas or solid phosgene reaction gained.Adopt the former yield to reach more than 90%, and adopt the latter's yield to only have about 85%, and solid phosgene is more expensive than phosgene.And adopt optical self-encoding, due to phosgene severe toxicity, security risk is very high, and country is very tight to the production and application management and control of phosgene, so main manufacturer both domestic and external is all use solid photoproduction to produce parachlorobenzyl isocyanic ester.
Gu light is also known as the wide gas of solid, triphosgene, two (trichloromethyl) carbonic ether, two (trichloromethyl) carbonic ether, be called for short BTC, using and convenience more safer with liquid trichloromethylchloroformate than the wide gas of gaseous state in transporting procedures.
The method that the solid light of existing use prepares chlorophenyl isocyanate is as follows:
Shanxi Polytechnics Wei Wen jade for asking rain (Wei Wenlong etc., the synthesis of chlorophenyl isocyanate, applied chemistry, in April, 2005, 34th volume the 4th phase, 224-225, 1369-371), clearly write exactly in its conclusion: the optimum reaction condition of synthesis chlorophenyl isocyanate is: with 1, 2-ethylene dichloride is solvent, triphosgene: p-Chlorobenzoic acid amide=1:2 (mol ratio), temperature of reaction is 75-82 DEG C, reaction times is 4.5h, concrete reactions steps is: to agitator is housed, triphosgene and 1 is added in the there-necked flask of thermometer and constant pressure funnel, 2-ethylene dichloride, after stirring and dissolving, p-Chlorobenzoic acid amide and 1, the solution of 2-ethylene dichloride slowly evenly instills reaction system through constant pressure funnel, and the temperature of reaction system is kept with ice bath, time for adding about 2 hours, room temperature reaction 1 hour, then heating reflux reaction 4.5 hours, suction filtration, recycling design, residue obtains product through underpressure distillation, yield is 81.0%.
People (the Du Xiaohua etc. such as Zhejiang University Du Xiaohua, solid phosgene method synthesis chlorophenyl monoisocyanates, applied chemistry, in November, 2008,25th volume o. 11th, conclusion part 1019-1021), determines that the mol ratio of fixing chloro aminobenzen and solid phosgene is 2:1 (aniline 0.1mol, BTC0.05mol), solvent load is 150mL, reaction times is 5 hours, when wherein selecting 1,2-ethylene dichloride as solvent, the yield of product is the highest, its reaction process with the method described in Wei Wenlong, parachlorobenzyl isocyanic ester yield 89.4%, purity 98.7%.
People (the Wang Xianghui etc. such as University Of Hainan king Xiang Hui, the synthesizing substituted isocyanic ester of triphosgene, applied chemistry, in September, 2008,37th volume the 9th phase, 1019-1021) disclose the method for the synthesizing substituted isocyanic ester of triphosgene, reaction process wherein, with the method described in Wei Wenlong, is write exactly in its conclusion: the mol ratio of triphosgene and substituted aniline is 1:2, reaction times be 3.5-5.5 hour not etc., solvent adopts toluene or 1,2-ethylene dichloride, and ultimate yield is 69.7-92.4%.
Report in CN 1475480A, being equipped with in thermometer, reflux condensing tube, constant pressure funnel and churned mechanically 500mL four-hole boiling flask, add 110g two < trichloromethyl > carbonic ether, 250ml solvent and 3g tetrabutyl urea.Open and stir, and start to drip lmol p-Chlorobenzoic acid amide, about add 0.5-1h.Finish, be warming up to backflow, and at 120-130 DEG C of reaction 3h, reaction terminates rear vacuum distillation recovered solvent, and product is received in last underpressure distillation, parachlorobenzyl isocyanic ester yield 90.5%.
Report in CN 101033203A, add solid phosgene in a kettle., after dissolving with toluene, start to drip p-Chlorobenzoic acid amide, toluene solution, each amounts of components is: p-Chlorobenzoic acid amide: solid phosgene: the mol ratio of toluene is 1:0.35-0.45:8-11; In dropping process, temperature is by lesser temps, heat up gradually, within the reaction times, temperature range is between 35-80 DEG C, adopt activated carbon decolorizing after reaction: vacuum back-flow: unreacted solid phosgene is also resolved into phosgene by gac, absorbed by device for absorbing tail gas together with the hydrogen chloride gas produced in time reacting and remove; Treat that material becomes to ask, stop backflow, steam part toluene: the rubigan different propylhomoserin enzyme solution yield of obtained 40% is more than 87%.
Above data parachlorobenzyl isocyanic ester yield is all about 90%, and two (trichloromethyl) carbonic ether more excessive than theoretical value about 50%, and can not directly apply mechanically after also finding solvent recuperation, must process and could use.
Therefore, need to provide a kind of rational technology, the method for production safety is reliable, reaction yield is high, quantity of solvent is few synthesis parachlorobenzyl isocyanic ester.
Summary of the invention
The object of this invention is to provide a kind of parachlorobenzyl isocyanic ester chemical synthesis process.
The preparation method of a kind of parachlorobenzyl isocyanic ester provided by the invention, the reaction formula of the method is as follows,
Comprise the following steps:
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: take p-Chlorobenzoic acid amide as raw material, in organic solvent and hydrochloric acid reaction, synthesis p-Chlorobenzoic acid amide hydrochloride;
2) p-Chlorobenzoic acid amide isocyanic ester is synthesized: p-Chlorobenzoic acid amide hydrochloride and solid light are raw material, synthesize p-Chlorobenzoic acid amide isocyanic ester in organic solvent.
In aforesaid method:
Described step 1) in:
The mol ratio of p-Chlorobenzoic acid amide and hydrochloric acid is 1:1.05-1.2;
Organic solvent is 1-4 times of p-Chlorobenzoic acid amide quality;
Described organic solvent is toluene, benzene, dimethylbenzene, chlorobenzene, orthodichlorobenzene, Meta Dichlorobenzene, normal hexane, 1,2-ethylene dichloride or propyl carbinol;
Its temperature of reaction 20-120 DEG C, is preferably 40-80 DEG C;
Reaction times is 2.5-4 hour.
Described step 2) in:
The mol ratio of p-Chlorobenzoic acid amide hydrochloride (in p-Chlorobenzoic acid amide) and solid light is 1:0.35-0.5, is preferably 1:0.4;
The consumption of organic solvent is 0.5-5 times of p-Chlorobenzoic acid amide hydrochloride quality;
Described organic solvent is for being ethyl acetate, butylacetate, toluene, benzene, dimethylbenzene, chlorobenzene, orthodichlorobenzene, Meta Dichlorobenzene or 1,2-ethylene dichloride;
Reaction times is 6-10 hour.
Preferably, said method comprising the steps of:
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: take p-Chlorobenzoic acid amide as raw material, in organic solvent and hydrochloric acid reaction, synthesis p-Chlorobenzoic acid amide hydrochloride, wherein the mol ratio of p-Chlorobenzoic acid amide and hydrochloric acid is 1:1.05-1.2, consumption of organic solvent is 1-4 times of volume of p-Chlorobenzoic acid amide quality, temperature of reaction is 20-120 DEG C, and its reaction times is 2.5-4 hour;
2) p-Chlorobenzoic acid amide isocyanic ester is synthesized: p-Chlorobenzoic acid amide hydrochloride and solid light are raw material, synthesize p-Chlorobenzoic acid amide isocyanic ester in organic solvent, wherein in the mol ratio of p-Chlorobenzoic acid amide p-Chlorobenzoic acid amide hydrochloride and solid light for 1:0.34-0.5, consumption of organic solvent is the 0.8-3 of p-Chlorobenzoic acid amide, reaction times is 6-10h, normal pressure steams organic solvent, and then underpressure distillation obtains p-Chlorobenzoic acid amide isocyanic ester.
Further preferably, said method comprising the steps of:
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: be added in reactor by p-Chlorobenzoic acid amide and organic solvent, be warming up to 40-50 DEG C, concentrated hydrochloric acid is dripped in 0.5-1 hour, the mol ratio of p-Chlorobenzoic acid amide and hydrochloric acid is 1:1.05-1.2, consumption of organic solvent is 1-4 times of volume of p-Chlorobenzoic acid amide quality, is then warming up to reflux water-dividing 2 hours, separates to anhydrous, then be cooled to less than 40 DEG C, centrifugally filter out intermediate p-Chlorobenzoic acid amide hydrochloride;
2) p-Chlorobenzoic acid amide isocyanic ester is synthesized: be added in reactor by p-Chlorobenzoic acid amide hydrochloride, solid light and organic solvent, in the mol ratio of p-Chlorobenzoic acid amide p-Chlorobenzoic acid amide hydrochloride and solid light for 1:0.34-0.5, consumption of organic solvent is 0.8-2.5 times of p-Chlorobenzoic acid amide hydrochloride, be warming up to 50-60 DEG C of reaction 2 hours, 80 DEG C are reacted 1 hour, then back flow reaction 3 hours, has reacted rear normal pressure and has steamed organic solvent, and then underpressure distillation obtains p-Chlorobenzoic acid amide isocyanic ester.
The effect that the present invention is useful is:
1, compared with current production technology, preparation method's operational path provided by the invention is advanced, and processing condition are reasonable, and raw material used avoids Guangzhou Automobile Workshop and the trichloromethylchloroformate of severe toxicity, and production safety is reliable, and reaction yield is high, generally more than 95%.Produce material used seldom excessive, and it is little often to walk reaction solvent consumption, improves plant factor, intermediate must be not dry, and directly can carry out next step reaction, quantity of three wastes is little, and is easy to process.There is good implementary value and social benefit.
2, existing patent is all single stage method, yield about 90%, and the present invention is two-step approach, and the yield of two-step approach reaches about 97%, and the first step is p-Chlorobenzoic acid amide and hydrochloric acid reaction, generates p-Chlorobenzoic acid amide hydrochloride.P-Chlorobenzoic acid amide hydrochloride, reacting with solid phosgene, produces product.Due to p-Chlorobenzoic acid amide hydrochloride and solid photoresponse, by product is less, so yield is improved.
Embodiment
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.
The multiple volume of quality, is not particularly illustrated in the present invention, the corresponding international unit all referred to or its multiple, such as quality g, and volume is ml.
Embodiment 1: the preparation method of p-Chlorobenzoic acid amide isocyanic ester
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: in 500ml there-necked flask, add p-Chlorobenzoic acid amide 102.18g (0.8mol) and toluene 200g (being equivalent to 1.96 times of p-Chlorobenzoic acid amide), stir, be warming up to 50 DEG C, drip the concentrated hydrochloric acid (concentration 36% of 86g, 0.84mol, be equivalent to 1.05 times of p-Chlorobenzoic acid amide), within about 40 minutes, dropwise, be warming up to reflux water-dividing, after dividing water, about two hours, be cooled to 40 DEG C, centrifuging, recovery toluene, filter cake directly casts single step reaction;
2) p-Chlorobenzoic acid amide isocyanic ester is synthesized: add in 500ml there-necked flask and walk not dry p-Chlorobenzoic acid amide hydrochloride (about about 130g, in p-Chlorobenzoic acid amide, its mole number is 0.8mol, lower same), Gu light 95g (0.32mol, be equivalent to 0.4 times of p-Chlorobenzoic acid amide) and ethyl acetate 100g (being equivalent to 0.77 times of p-Chlorobenzoic acid amide hydrochloride weight), stir, heat up, 60 DEG C of insulations 2 hours, then 80 DEG C are warming up to, keep this temperature 1 hour, be warming up to reactor temperature and be about 90 DEG C, continue back flow reaction 3 hours, then air distillation solvent about 1 hour, reclaim ethyl acetate, pass through underpressure distillation again, vacuum 0.095Mpa, about 1 hour, obtain parachlorobenzyl isocyanic ester.Weight 117.04g, yield 95.15%, GC content 99.06%.
Embodiment 2: the preparation method of p-Chlorobenzoic acid amide isocyanic ester
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: in 500ml there-necked flask, add p-Chlorobenzoic acid amide 102.18g (0.8mol) and reclaim toluene 250g (being equivalent to 2.45 times of p-Chlorobenzoic acid amide), stir, 98g (concentration 36% is dripped at 40 DEG C, 0.96mol, be equivalent to 1.2 times of p-Chlorobenzoic acid amide) concentrated hydrochloric acid, within about 55 minutes, dropwise, temperature rising reflux divides water, after dividing water, about two hours.Be cooled to 40 DEG C, centrifuging, recovery toluene.Filter cake directly casts single step reaction;
2) parachlorobenzyl isocyanic ester is synthesized: add in 500ml there-necked flask and walk not dry p-Chlorobenzoic acid amide hydrochloride (about about 130g is in p-Chlorobenzoic acid amide, its mole number is 0.8mol), the ethyl acetate 200g (being equivalent to 1.54 times of p-Chlorobenzoic acid amide hydrochloride quality) of solid light 83g (0.28mol, p-Chlorobenzoic acid amide hydrochloride 0.35 times) and recovery.Stir, heat up, 55 DEG C of insulations 2 hours, then 80 DEG C are warming up to, keep this temperature 1 hour, be warming up to reactor temperature and be about 90 DEG C, continue back flow reaction 3 hours, then air distillation solvent, reclaim ethyl acetate, about need 1 hour, then underpressure distillation obtains parachlorobenzyl isocyanic ester under 0.095Mpa vacuum.About need one hour, weight 119.74g, yield 97.46%, GC content 99.56%.
Embodiment 3: the preparation method of p-Chlorobenzoic acid amide isocyanic ester
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: synthesis p-Chlorobenzoic acid amide isocyanic ester: add p-Chlorobenzoic acid amide 102.18g (0.8mol) and dimethylbenzene 300g (being equivalent to 2.94 times of p-Chlorobenzoic acid amide) in 500ml there-necked flask, stir, 90g concentrated hydrochloric acid (concentration 36%, 0.88mol is equivalent to 1.1 times of p-Chlorobenzoic acid amide) is dripped at 45 DEG C, within about 45 minutes, dropwise, temperature rising reflux divides water, after point water, and about two hours, normal pressure steams toluene, about 145g.Then be cooled to 35 DEG C, centrifugally filter out intermediate p-Chlorobenzoic acid amide hydrochloride, about need 2 hours, filter cake directly casts single step reaction.
2) parachlorobenzyl isocyanic ester is synthesized: add in 500ml there-necked flask and walk not dry p-Chlorobenzoic acid amide hydrochloride (about about 130g is in p-Chlorobenzoic acid amide, its mole number is 0.8mol), then the ethyl acetate 150g (being equivalent to 1.15 times of p-Chlorobenzoic acid amide hydrochloride quality) reinforcing light 119g (0.344mol is equivalent to 0.43 times of p-Chlorobenzoic acid amide hydrochloride quality) and reclaim in reaction flask.Stir, heat up, 50 DEG C of insulations 2 hours, then 80 DEG C are warming up to, keep this temperature 1 hour, be warming up to reactor temperature and be about 90 DEG C, continue back flow reaction 3 hours, then air distillation solvent, reclaim ethyl acetate, about need 1 hour, then underpressure distillation obtains parachlorobenzyl isocyanic ester under 0.095Mpa vacuum.Weight 117.04g, yield 95.28%, GC content 99.58%.
Embodiment 4: the preparation method of p-Chlorobenzoic acid amide isocyanic ester
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: in 500ml there-necked flask, add p-Chlorobenzoic acid amide 102.18g (0.8mol) and propyl carbinol 350g (being equivalent to 3.4 times of p-Chlorobenzoic acid amide), stir, 94g (concentration 36% is dripped at 50 DEG C, 0.92mol, be equivalent to 1.15 times of p-Chlorobenzoic acid amide) concentrated hydrochloric acid, within about 48 minutes, dropwise, temperature rising reflux divides water, after dividing water, about two hours.Be cooled to 40 DEG C, centrifuging, filter cake are 80 DEG C of vacuum-dryings to constant weight, and p-Chlorobenzoic acid amide hydrochloride weighs 130.08g, yield 99.13%;
2) parachlorobenzyl isocyanic ester is synthesized: in 500ml there-necked flask, add the p-Chlorobenzoic acid amide hydrochloride 130.08g (0.793mol) walking synthesis, solid light 118.75g (0.4mol, mole number is 0.5 times of p-Chlorobenzoic acid amide hydrochloride) and N-BUTYL ACETATE 250g (being equivalent to 1.92 times of p-Chlorobenzoic acid amide hydrochloride quality).Stir, heat up, 55 DEG C of insulations 2 hours, then 80 DEG C are warming up to, keep this temperature 1 hour, be warming up to reactor temperature and be about 126 DEG C, continue back flow reaction 4..5 hour, then air distillation solvent, reclaim butylacetate, about need 1.5 hours, then underpressure distillation obtains parachlorobenzyl isocyanic ester under 0.095Mpa vacuum.About need 1 hour, weight 114.25g, yield 93%, GC content 99.68%.
Embodiment 5: the preparation method of p-Chlorobenzoic acid amide isocyanic ester
Synthesis parachlorobenzyl isocyanic ester synthesis: add p-Chlorobenzoic acid amide hydrochloride 131.22g (in p-Chlorobenzoic acid amide in 500ml there-necked flask, its mole number is 0.8mol), solid light 83.09g (0.28mol, p-Chlorobenzoic acid amide hydrochloride 0.35 times) and vinyl acetic monomer 100g (being equivalent to 0.76 times of p-Chlorobenzoic acid amide hydrochloride quality).Stir, heat up, 60 DEG C of insulations 1 hour, then 80 DEG C are warming up to, keep this temperature 2 hours, be warming up to reactor temperature and be about 90 DEG C, continue back flow reaction 3 hours, then air distillation solvent, reclaim ethyl acetate, about need 1 hour, then underpressure distillation obtains parachlorobenzyl isocyanic ester under 0.095Mpa vacuum.About need 1 hour, weight 114.68g, yield 93.34%, GC content 99.75%.
Reference examples
Agitator, thermometer, condenser is placed in the reactor device of 1000ml,
Add solid light 100g, toluene 300ml, after stirring and dissolving, be added dropwise to by the solution prepared chlorobenzene glue 100g and toluene 500ml, dripping starting temperature is 35 DEG C, and in dropping process, control temperature scope is below 60 DEG C, dropwises and is incubated half an hour, be warming up to 80 DEG C again, be incubated two hours, add a small amount of activated carbon, vacuum back-flow, remove the hydrogen chloride gas of unreacted phosgene and generation, treat that material becomes clear, stop backflow, steam toluene: decompression steams parachlorobenzyl isocyanic ester, yield is at 87.5%, GC content 99.1%.
Although above with general explanation, embodiment and test, the present invention is described in detail, and on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (8)
1. a preparation method for parachlorobenzyl isocyanic ester, the reaction formula of the method is as follows,
Comprise the following steps:
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: take p-Chlorobenzoic acid amide as raw material, in organic solvent and hydrochloric acid reaction, synthesis p-Chlorobenzoic acid amide hydrochloride;
2) p-Chlorobenzoic acid amide isocyanic ester is synthesized: p-Chlorobenzoic acid amide hydrochloride and solid light are raw material, synthesize p-Chlorobenzoic acid amide isocyanic ester in organic solvent.
2. method according to claim 1, is characterized in that, described step 1) in: the mol ratio of p-Chlorobenzoic acid amide and hydrochloric acid is 1:1.05-1.2.
3. method according to claim 1, it is characterized in that, described step 1) in: organic solvent is 1-4 times of p-Chlorobenzoic acid amide quality, and described organic solvent is toluene, benzene, dimethylbenzene, chlorobenzene, orthodichlorobenzene, Meta Dichlorobenzene, normal hexane, 1,2-ethylene dichloride or propyl carbinol.
4. method according to claim 1, is characterized in that, described step 1) in: its temperature of reaction 20-120 DEG C, the reaction times is 2.5-4 hour.
5. method according to claim 1, is characterized in that, described step 2) in: in the mol ratio of p-Chlorobenzoic acid amide p-Chlorobenzoic acid amide hydrochloride and solid light for 1:0.35-0.5.
6. method according to claim 1, it is characterized in that, described step 2) in: the consumption of organic solvent is 0.5-5 times of p-Chlorobenzoic acid amide hydrochloride quality, described organic solvent is for being ethyl acetate, butylacetate, toluene, benzene, dimethylbenzene, chlorobenzene, orthodichlorobenzene, Meta Dichlorobenzene or 1,2-ethylene dichloride.
7. the method according to any one of claim 1-6, is characterized in that, the method comprises the following steps:
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: take p-Chlorobenzoic acid amide as raw material, in organic solvent and hydrochloric acid reaction, synthesis p-Chlorobenzoic acid amide hydrochloride, wherein the mol ratio of p-Chlorobenzoic acid amide and hydrochloric acid is 1:1.05-1.2, consumption of organic solvent is 1-4 times of volume of p-Chlorobenzoic acid amide quality, temperature of reaction is 20-120 DEG C, and its reaction times is 2.5-4 hour;
2) p-Chlorobenzoic acid amide isocyanic ester is synthesized: p-Chlorobenzoic acid amide hydrochloride and solid light are raw material, synthesize p-Chlorobenzoic acid amide isocyanic ester in organic solvent, wherein in the mol ratio of p-Chlorobenzoic acid amide p-Chlorobenzoic acid amide hydrochloride and solid light for 1:0.34-0.5, consumption of organic solvent is the 0.8-3 of p-Chlorobenzoic acid amide, reaction times is 6-10h, normal pressure steams organic solvent, and then underpressure distillation obtains p-Chlorobenzoic acid amide isocyanic ester.
8. method according to claim 7, is characterized in that, the method comprises the following steps:
1) p-Chlorobenzoic acid amide hydrochloride is synthesized: be added in reactor by p-Chlorobenzoic acid amide and organic solvent, be warming up to 40-50 DEG C, concentrated hydrochloric acid is dripped in 0.5-1 hour, the mol ratio of p-Chlorobenzoic acid amide and hydrochloric acid is 1:1.05-1.2, consumption of organic solvent is 1-4 times of volume of p-Chlorobenzoic acid amide quality, is then warming up to reflux water-dividing 2 hours, separates to anhydrous, then be cooled to less than 40 DEG C, centrifugally filter out intermediate p-Chlorobenzoic acid amide hydrochloride;
2) p-Chlorobenzoic acid amide isocyanic ester is synthesized: be added in reactor by p-Chlorobenzoic acid amide hydrochloride, solid light and organic solvent, in the mol ratio of p-Chlorobenzoic acid amide p-Chlorobenzoic acid amide hydrochloride and solid light for 1:0.34-0.5, consumption of organic solvent is 0.8-2.5 times of p-Chlorobenzoic acid amide hydrochloride, be warming up to 50-60 DEG C of reaction 2 hours, 80 DEG C are reacted 1 hour, then back flow reaction 3 hours, has reacted rear normal pressure and has steamed organic solvent, and then underpressure distillation obtains p-Chlorobenzoic acid amide isocyanic ester.
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| CN110467533A (en) * | 2019-09-26 | 2019-11-19 | 辽宁顺通化工股份有限公司 | A kind of preparation method of parachloroanilinum hydrochloride |
| CN111548287A (en) * | 2020-06-16 | 2020-08-18 | 濮阳市宏大圣导新材料有限公司 | Preparation method of cyclohexyl isocyanate |
| CN111662214A (en) * | 2020-06-24 | 2020-09-15 | 江苏蓝丰生物化工股份有限公司 | Method for preparing cyclohexyl isocyanate by using solid phosgene |
| CN114380716A (en) * | 2022-01-27 | 2022-04-22 | 浙江丽水有邦新材料有限公司 | Production method and production system of p-chlorophenyl isocyanate |
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| CN110467533A (en) * | 2019-09-26 | 2019-11-19 | 辽宁顺通化工股份有限公司 | A kind of preparation method of parachloroanilinum hydrochloride |
| CN111548287A (en) * | 2020-06-16 | 2020-08-18 | 濮阳市宏大圣导新材料有限公司 | Preparation method of cyclohexyl isocyanate |
| CN111662214A (en) * | 2020-06-24 | 2020-09-15 | 江苏蓝丰生物化工股份有限公司 | Method for preparing cyclohexyl isocyanate by using solid phosgene |
| CN114380716A (en) * | 2022-01-27 | 2022-04-22 | 浙江丽水有邦新材料有限公司 | Production method and production system of p-chlorophenyl isocyanate |
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