CN108863767A - A kind of synthetic method of 4- chlorobutanoylchloride - Google Patents
A kind of synthetic method of 4- chlorobutanoylchloride Download PDFInfo
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- CN108863767A CN108863767A CN201810899341.5A CN201810899341A CN108863767A CN 108863767 A CN108863767 A CN 108863767A CN 201810899341 A CN201810899341 A CN 201810899341A CN 108863767 A CN108863767 A CN 108863767A
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- chlorobutanoylchloride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/64—Separation; Purification; Stabilisation; Use of additives
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Abstract
The present invention relates to a kind of synthetic methods of 4- chlorobutanoylchloride, which is characterized in that using gamma-butyrolacton, two (trichloromethyl) carbonic esters as reaction raw materials, using specific amines catalyst, carries out chlorination reaction, obtains 4- chlorobutanoylchloride.Wherein, the amines catalyst is the intercalation product obtained after aluminium dihydrogen tripolyphosphate is reacted with organic amine, and structure is as follows：
Description
Technical field
The present invention relates to a kind of synthetic methods of 4- chlorobutanoylchloride.
Background technique
4- chlorobutanoylchloride is one kind important organic synthesis and medicine, pesticide intermediate.
In medical industry, 4- chlorobutanoylchloride is for producing antipsychotics psychoperidol, trichlorine Serenase, Zuo Yila
It is western smooth, carbostyril family antibacterial drugs Ciprofloxacin, Profloxacin, sparfloxacin etc..It can be used for preparing Yi Evil in pesticide industry
Chlorine humulone, isoxaflutole etc..
Currently, existing 4- chlorobutanoylchloride industrialized preparing process is passed through mainly under zinc chloride catalysis by gamma-butyrolacton
Thionyl chloride chlorination and obtain, yield 82% or so, though the technique is easy to operate, raw material is easy to get, but the cost of raw material is higher, three
It gives up more.
In addition, in patent US2778852, in GB743557, EP0413264 etc., it is also proposed that substituted by raw material of phosgene
Thionyl chloride is chlorination reagent, synthesizes 4- chlorobutanoylchloride by gamma-butyrolacton, and yield is up to 95%.Such as.This method high income, raw material light
Gas is cheap compared with thionyl chloride, simple process, no SO2Exhaust gas, the three wastes are less, but chlorination reagent phosgene inherently severe toxicity chemistry
Product, and transport, storage inconvenience, high operation requirements.
In CN104086402A, proposes and, for chlorination reagent, closed by gamma-butyrolacton with two (trichloromethyl) carbonic esters
At 4- chlorobutanoylchloride, in the reaction, use organic amine as catalyst, at the same use phase transfer catalyst, this method yield compared with
Height, but post-process difficult, when industrialization, separates increased costs, and yield is substantially reduced when being amplified to industrialized production.
In CN104592001A, proposes and reacted under mixed catalyst using gamma-butyrolacton with thionyl chloride, gained
Product purity is higher, but it is higher to still remain the cost of raw material, there is severe toxicity, the more problem of the three wastes.
Since the market of 4- chlorobutanoylchloride needs increasingly to improve, it is badly in need of a kind of high income, is able to satisfy industrialized production
Needs, and lower-cost synthetic method.
Summary of the invention
Goal of the invention of the invention is to provide a kind of high income, at low cost, is suitable for industrial 4- chlorobutanoylchloride
Preparation method.
It is prepared in the reacting of 4- chlorobutanoylchloride in known gamma-butyrolacton and two (trichloromethyl) carbonic esters, it usually needs
Organic amine catalyst, as known in the art, although the reaction industrialized route is simple, there are problems that yield, though
It proposes to use phase transfer catalyst in right CN104086402A, but undoubtedly increases the difficulty of industrial operation, meanwhile, according to this
The experimental condition of application amplifies test, and yield is substantially reduced, this is considered due in large-scale production, phase transfer catalysis (PTC)
Agent can not effectively include amines catalyst, lead to not obtain sufficient catalytic effect.If increasing making for phase transfer catalyst
Dosage, although yield can be increased, final separation is difficult, and cost is caused to significantly improve.
Applicant in view of the above-mentioned problems, carried out meticulous research, as a result, it has been found that, using specific organic amine catalyst,
It can solve the above problem.
The technical solution adopted by the present invention is as follows：
A kind of synthetic method of 4- chlorobutanoylchloride, which is characterized in that be with gamma-butyrolacton, two (trichloromethyl) carbonic esters
Reaction raw materials are carried out chlorination reaction, are obtained 4- chlorobutanoylchloride using specific amines catalyst.
Wherein, the amines catalyst is the intercalation product obtained after aluminium dihydrogen tripolyphosphate is reacted with organic amine, knot
Structure is as follows：
Wherein, R is alkyl, aromatic radical, the preferably alkyl of C1-3, the aromatic radical of C6-12, more preferably methyl, ethyl,
Phenyl, pyridyl group.
Aluminium dihydrogen tripolyphosphate is the compound of layer structure and inorganic ions switching performance known in the art.Its with
The intercalation of aminated compounds is known in the art (referring to the intercalation of aluminium dihydrogen tripolyphosphate and organic amine spy
Sign, applied chemistry, 2014,31 (7)).
It has been found that in the reacting of gamma-butyrolacton and two (trichloromethyl) carbonic esters, using the specific catalysis
Agent, reaction yield are improved, and even if being amplified to industrial production rank, reaction yield is not also decreased obviously, and can be reached
90% or more, hence it is evident that be better than the prior art.
The specific reaction step of technical solution of the present invention is as follows：
At room temperature, first gamma-butyrolacton, amines catalyst are mixed, under stiring, two (trichloromethyls) is added thereto
Carbonic ester, heating carry out chlorination reaction.End of reaction, separation product is up to 4- chlorobutanoylchloride.
In reaction, the mass ratio of the material of gamma-butyrolacton and two (trichloromethyl) carbonic esters is 1：(0.5-2), preferably 1：
(1-2).The ratio of the amount of the substance of gamma-butyrolacton and amines catalyst is 1：(0.1-3), preferably 1：(0.1-1).The temperature of heating
Degree is 60-120 DEG C, preferably 80-100 DEG C.The heating reaction time is 0.5-4h.
Organic solvent used in chlorination reaction is selected from：Toluene, 1,2- dichloroethanes, 4- chlorobutanoate, dimethylbenzene, chlorine
Benzene, ortho-chlorotolu'ene, o-dichlorohenzene, m-dichlorobenzene.The dosage of the organic solvent is not limited, as long as reactant can be dissolved
?.
After the completion of reaction, it is post-processed, treatment process is：Reaction solution is distilled desolventizing, dry, obtains 4-
Chlorobutanoylchloride.It is preferred that as follows：For reaction solution after distilling desolventizing, rectifying takes 105 DEG C of -112 DEG C of fractions, dry, obtains 4- neoprene
Acyl chlorides.
Chlorination reaction of the present invention can carry out as follows：Organic solvent is added in the reaction vessel, γ-is then added
Butyrolactone, amines catalyst are added the solution dissolved with two (trichloromethyl) carbonic esters thereto later, carry out at 60-120 DEG C
Chlorination reaction 0.5-4h, end of reaction, reaction solution is through distilling desolventizing, and then rectification under vacuum takes 105 DEG C of -112 DEG C of fractions, does
It is dry, obtain 4- chlorobutanoylchloride；The catalyst is：Amines catalyst is to obtain after aluminium dihydrogen tripolyphosphate is reacted with organic amine
Intercalation product, structure is as follows：
Wherein, R is alkyl, aromatic radical, the preferably alkyl of C1-3, the aromatic radical of C6-12, more preferably methyl, ethyl,
Phenyl, pyridyl group, the additional amount of catalyst are the 0.1-10mol% of gamma-butyrolacton；Two (trichloromethyl) carbonic esters and
The mass ratio of the material of gamma-butyrolacton be 1: 1-5, the organic solvent be ortho-chlorotolu'ene, m-dichlorobenzene or o-dichlorohenzene, it is organic
The dosage of solvent is to be calculated as 2-10ml/g with gamma-butyrolacton quality.
The 4- chlorobutanoylchloride synthetic method provided according to the present invention, after being amplified to industrial rank, reaction yield still compared with
Height has reached 90% or more, and reaction condition is mild, safe operation, is suitable for industrialized production.
Specific embodiment
The present invention is further illustrated below by embodiment.It should be understood that the preparation method of the embodiment of the present invention is only
It is only for illustrating the present invention, rather than limiting the invention, to preparation method of the present invention under concept thereof of the invention
Simple modifications belong to the scope of protection of present invention.
Catalyst preparation example 1：
According to the intercalation feature of aluminium dihydrogen tripolyphosphate and organic amine, applied chemistry, side described in 2014,31 (7)
Methylamine and water is added in method in the reactor, and dissolution is put into aluminium dihydrogen tripolyphosphate, is stirred to react at normal temperature, separates, obtains
Catalyst A.
Catalyst preparation example 2：
According to method same as catalyst preparation example 1, other than ethamine is added and replaces methylamine, remaining is identical, obtains
Obtain catalyst B.
Catalyst preparation example 3：
According to method same as catalyst preparation example 1, other than pyridine is added and replaces methylamine and water, remaining is identical,
Obtain catalyst C.
Embodiment 1：The preparation of 4- chlorobutanoylchloride
Toluene is added in a kettle, 20mol gamma-butyrolacton, 2mol catalyst A is then added, stirring is pressed from both sides in reaction kettle
By warming-in-water to 80 DEG C in set, while it being slowly added to the toluene solution of 20mol bis- (trichloromethyl) carbonic ester, is added and completes
Afterwards, reaction temperature is kept, 2.5h is reacted under stiring, is passed through nitrogen purge later, obtain crude reaction liquid, by being evaporated under reduced pressure,
Fractional Collections fraction, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, to get 4- neoprene after fraction is dried
Acyl chlorides 2.61kg, yield 92.5%.
The preparation of 2 4- chlorobutanoylchloride of embodiment：
Toluene is added in a kettle, 45mol gamma-butyrolacton, 3mol catalyst B is then added, stirring is pressed from both sides in reaction kettle
By warming-in-water to 80 DEG C in set, while it being slowly added to the toluene solution of 45mol bis- (trichloromethyl) carbonic ester, is added and completes
Afterwards, reaction temperature is kept, 3h is reacted under stiring, is passed through nitrogen purge later, obtain crude reaction liquid, by vacuum distillation, is divided
Section collects fraction, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, to get 4- neoprene acyl after fraction is dried
Chlorine 5.81kg, yield 91.6%.
The preparation of 3 4- chlorobutanoylchloride of embodiment：
Toluene is added in a kettle, 45mol gamma-butyrolacton, 4mol catalyst C is then added, stirring is pressed from both sides in reaction kettle
By warming-in-water to 80 DEG C in set, while it being slowly added to the toluene solution of 45mol bis- (trichloromethyl) carbonic ester, is added and completes
Afterwards, reaction temperature is kept, 2h is reacted under stiring, is passed through nitrogen purge later, obtain crude reaction liquid, by vacuum distillation, is divided
Section collects fraction, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, to get 4- neoprene acyl after fraction is dried
Chlorine 5.72kg, yield 90.1%.
Embodiment 4：The preparation of 4- chlorobutanoylchloride
Toluene is added in a kettle, 30mol gamma-butyrolacton, 4mol catalyst A is then added, stirring is pressed from both sides in reaction kettle
By warming-in-water to 80 DEG C in set, while it being slowly added to the toluene solution of 30mol bis- (trichloromethyl) carbonic ester, is added and completes
Afterwards, reaction temperature is kept, 3h is reacted under stiring, is passed through nitrogen purge later, obtain crude reaction liquid, by vacuum distillation, is divided
Section collects fraction, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, to get 4- neoprene acyl after fraction is dried
Chlorine 3.98kg, yield 94.1%.
Embodiment 5：The preparation of 4- chlorobutanoylchloride
1,2- dichloroethanes is added in a kettle, 30mol gamma-butyrolacton is then added, 4mol catalyst A is stirred,
By warming-in-water to 80 DEG C in reacting kettle jacketing, while it being slowly added to the toluene solution of 30mol bis- (trichloromethyl) carbonic ester,
After the completion of addition, reaction temperature is kept, 4h is reacted under stiring, is passed through nitrogen purge later, obtain crude reaction liquid, pass through decompression
Distillation, Fractional Collections fraction, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, by fraction it is dry after to get
4- chlorobutanoylchloride 3.83kg, yield 90.6%.
Embodiment 6：The preparation of 4- chlorobutanoylchloride
Toluene is added in a kettle, 20mol gamma-butyrolacton, 3mol catalyst A is then added, stirring is pressed from both sides in reaction kettle
By warming-in-water to 80 DEG C in set, while it being slowly added to the toluene solution of 20mol bis- (trichloromethyl) carbonic ester, is added and completes
Afterwards, reaction temperature is kept, 2.5h is reacted under stiring, is passed through nitrogen purge later, obtain crude reaction liquid, by being evaporated under reduced pressure,
Fractional Collections fraction, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, to get 4- neoprene after fraction is dried
Acyl chlorides 2.56kg, yield 91.0%.
Embodiment 7：The preparation of 4- chlorobutanoylchloride
Toluene is added in a kettle, 20mol gamma-butyrolacton, 4mol catalyst A is then added, stirring is pressed from both sides in reaction kettle
By warming-in-water to 80 DEG C in set, while it being slowly added to the toluene solution of 20mol bis- (trichloromethyl) carbonic ester, is added and completes
Afterwards, reaction temperature is kept, 2.5h is reacted under stiring, is passed through nitrogen purge later, obtain crude reaction liquid, by being evaporated under reduced pressure,
Fractional Collections fraction, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, to get 4- neoprene after fraction is dried
Acyl chlorides 2.61kg, yield 92.5%.
Comparative example 1：The preparation of 4- chlorobutanoylchloride
The embodiment is amplified to industrialization rank according to the method for CN104086402A embodiment 1 in proportion.
Ortho-chlorotolu'ene is added in a kettle, 20mol gamma-butyrolacton, 4mol pyridine and 1mol 18- crown- is then added
6, stirring by warming-in-water to 80 DEG C in reacting kettle jacketing, while being slowly added to 20mol bis- (trichloromethyl) carbonic ester
Ortho-chlorotolu'ene solution after the completion of addition, keeps reaction temperature, reacts 6h under stiring, be passed through nitrogen purge later, obtains thick anti-
Liquid is answered, vacuum distillation, Fractional Collections fraction are passed through, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, will be evaporated
Divide after drying to get 4- chlorobutanoylchloride 1.97kg, yield 70.1%.During the separation process, 18- crown- 6 can not be recycled effectively,
It is discharged with waste liquid.
Comparative example 2：The preparation of 4- chlorobutanoylchloride
The embodiment is amplified to industrialization rank according to the method for CN104086402A embodiment 2 in proportion.
O-dichlorohenzene is added in a kettle, 20mol gamma-butyrolacton, 4mol triethylamine and 1mol 18- is then added
Crown- 6, stirring by warming-in-water to 80 DEG C in reacting kettle jacketing, while being slowly added to 20mol bis- (trichloromethyl) carbonic acid
The toluene solution of ester after the completion of addition, keeps reaction temperature, reacts 4h under stiring, be passed through nitrogen purge later, obtains thick anti-
Liquid is answered, vacuum distillation, Fractional Collections fraction are passed through, wherein 105 DEG C of -112 DEG C of fractions (50mmHg) are 4- chlorobutanoylchloride, will be evaporated
Divide after drying to get 4- chlorobutanoylchloride 2.09kg, yield 74.6%.During the separation process, 18- crown- 6 can not be recycled effectively,
It is discharged with waste liquid.
Comparative example 3：The preparation of 4- chlorobutanoylchloride
Other than the usage amount of 18- crown- 6 is increased to 4mol, remaining is identical as comparative example 1, finally obtains
4- chlorobutanoylchloride 2.41kg, yield 85.2%.During the separation process, 18- crown- 6 can not be recycled effectively, most of to arrange with waste liquid
Out.
Comparative example 5：The preparation of 4- chlorobutanoylchloride
Other than the usage amount of 18- crown- 6 is increased to 4mol, remaining is identical as comparative example 2, finally obtains
4- chlorobutanoylchloride 2.45kg, yield 86.9%.During the separation process, 18- crown- 6 can not be recycled effectively, most of to arrange with waste liquid
Out.
As can be seen from the above embodiments, by means of the present invention, in the case where industrialized production, 4- chlorobutanoylchloride
Yield can also reach 90% or more, and reaction condition is mild, and easy to operate, industrialization can not be amplified to by solving the prior art
The problem of production.
Claims (8)
1. a kind of synthetic method of 4- chlorobutanoylchloride, which is characterized in that with gamma-butyrolacton, two (trichloromethyl) carbonic esters be anti-
Raw material is answered, using specific amines catalyst, chlorination reaction is carried out, obtains 4- chlorobutanoylchloride；
Wherein, the amines catalyst is the intercalation product obtained after aluminium dihydrogen tripolyphosphate is reacted with organic amine, and structure is such as
Under：
Wherein, R is alkyl, aromatic radical, the preferably alkyl of C1-3, the aromatic radical of C6-12, more preferably methyl, ethyl, benzene
Base, pyridyl group.
2. synthetic method as described in claim 1, it is characterised in that the organic amine is methylamine, ethamine or pyridine.
3. synthetic method as described in claim 1, which is characterized in that the amount of the substance of gamma-butyrolacton and amines catalyst
Than being 1：(0.1-3), preferably 1：(0.1-1).
4. synthetic method as described in claim 1, which is characterized in that at room temperature, first by gamma-butyrolacton, amines catalyst
Two (trichloromethyl) carbonic esters are added under stiring in mixing thereto, and heating carries out chlorination reaction, end of reaction, separation product
Up to 4- chlorobutanoylchloride.
5. synthetic method as claimed in claim 4, which is characterized in that the object of gamma-butyrolacton and two (trichloromethyl) carbonic esters
The amount ratio of matter is 1：(0.5-2), preferably 1：(1-2).
6. synthetic method as claimed in claim 4, which is characterized in that the temperature of heating is 60-120 DEG C, preferably 80-100
℃。
7. synthetic method as claimed in claim 4, which is characterized in that use organic solvent in chlorination reaction, which is selected from
Toluene, 1,2- dichloroethanes, 4- chlorobutanoate, dimethylbenzene, chlorobenzene, ortho-chlorotolu'ene, o-dichlorohenzene, m-dichlorobenzene.
8. a kind of synthetic method of 4- chlorobutanoylchloride, which is characterized in that organic solvent is added in the reaction vessel, is then added
The solution dissolved with two (trichloromethyl) carbonic esters is added, at 60-120 DEG C in gamma-butyrolacton, amines catalyst thereto later
Chlorination reaction 0.5-4h is carried out, end of reaction, reaction solution is through distilling desolventizing, and then rectification under vacuum takes 105 DEG C of -112 DEG C of fractions,
It is dry, obtain 4- chlorobutanoylchloride；The catalyst is：Amines catalyst is to obtain after aluminium dihydrogen tripolyphosphate is reacted with organic amine
The intercalation product arrived, structure are as follows：
Wherein, R is alkyl, aromatic radical, the preferably alkyl of C1-3, the aromatic radical of C6-12, more preferably methyl, ethyl, benzene
Base, pyridyl group, the additional amount of catalyst are the 0.1-10mol% of gamma-butyrolacton；Two (trichloromethyl) carbonic esters and
The mass ratio of the material of gamma-butyrolacton is 1: 1-5.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764309A (en) * | 1986-07-18 | 1988-08-16 | Basf Aktiengesellschaft | Preparation of chlorocarboxylic acid chlorides |
| CN101445447A (en) * | 2008-12-24 | 2009-06-03 | 浙江工业大学 | Synthesis method for 4-chlorobutyryl chloride |
| CN101624340A (en) * | 2009-08-13 | 2010-01-13 | 浙江国邦药业有限公司 | Preparation method of 4-chlorobutyroyl chloride |
| CN104086402A (en) * | 2014-07-16 | 2014-10-08 | 胡妍 | Method for synthesizing 4-chlorobutyryl chloride |
-
2018
- 2018-08-08 CN CN201810899341.5A patent/CN108863767A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764309A (en) * | 1986-07-18 | 1988-08-16 | Basf Aktiengesellschaft | Preparation of chlorocarboxylic acid chlorides |
| CN101445447A (en) * | 2008-12-24 | 2009-06-03 | 浙江工业大学 | Synthesis method for 4-chlorobutyryl chloride |
| CN101624340A (en) * | 2009-08-13 | 2010-01-13 | 浙江国邦药业有限公司 | Preparation method of 4-chlorobutyroyl chloride |
| CN104086402A (en) * | 2014-07-16 | 2014-10-08 | 胡妍 | Method for synthesizing 4-chlorobutyryl chloride |
Non-Patent Citations (3)
| Title |
|---|
| 吴胜富等: "三聚磷酸二氢铝与有机胺的插层反应特征", 《应用化学》 * |
| 牛宇岚等: "4-氯丁酰氯的合成研究 ", 《精细化工中间体》 * |
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