CN108046996B - Continuous synthesis method of 2, 5-dichlorophenol - Google Patents
Continuous synthesis method of 2, 5-dichlorophenol Download PDFInfo
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
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Abstract
The invention provides a continuous synthesis method of 2, 5-dichlorophenol, which relates to the technical field of organic synthesis and comprises the following steps: (1) loading heteropoly acid and heteropoly acid salt supported catalyst onto a fixed bed reactor; (2) pumping 1,2,4 trichlorobenzene and strong alkali solution into a fixed bed reactor for hydrolysis reaction; (3) after the hydrolysis reaction is finished, pumping the reaction liquid and hydrochloric acid into a tubular reactor for acidification reaction, and removing a water layer from the obtained acidification liquid after the reaction is completed; (4) the 2, 5-dichlorophenol can be obtained by distilling and purifying the organic layer, and the method has the advantages of simple process and continuous production.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a continuous synthesis method of 2, 5-dichlorophenol.
Background
2, 5-dichlorophenol is an important organic intermediate, is mainly used for synthesizing benzoic acid herbicide-dicamba, and can also be used for synthesizing chemicals such as nitrogen fertilizer synergist, leather mildew preventive, DP mildew preventive and the like.
At present, two methods are mainly used for synthesizing 2, 5-dichlorophenol, one method is to directly carry out catalytic oxidation by taking p-dichlorobenzene as a raw material and hydrogen peroxide as a catalyst to obtain the 2, 5-dichlorophenol, but the reaction has low conversion rate and high recovery cost, and is not suitable for industrial production; secondly, 2, 5-dichloroaniline is used as a raw material to prepare 2, 5-dichlorophenol through diazotization, hydrolysis and other reactions, and the method has a long reaction route, needs diazotization reaction and generates a large amount of acid wastewater which is difficult to treat.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a continuous synthesis method of 2, 5-dichlorophenol, which has the advantages of simple process and continuous production.
(II) technical scheme
In order to achieve the purpose, the invention is realized by the following technical scheme:
a continuous synthesis method of 2, 5-dichlorophenol comprises the following steps:
(1) loading heteropoly acid and heteropoly acid salt supported catalyst onto a fixed bed reactor;
(2) pumping 1,2, 4-trichlorobenzene and strong alkali solution into a fixed bed reactor for hydrolysis reaction;
(3) after the hydrolysis reaction is finished, pumping the reaction liquid and hydrochloric acid into a tubular reactor for acidification reaction, and removing a water layer from the obtained acidification liquid after the reaction is completed;
(4) and distilling and purifying the organic layer to obtain the 2, 5-dichlorophenol.
Preferably, the heteropoly acid and heteropoly acid salt supported catalyst in the step (1) is Pd-H4SiW12O40/SiO2、Pd-H4SiMo12O40/SiO2、Pd-H3PSiW12O40/SiO2And Pd-H3PSiMo12O40/SiO2One or more of them.
Preferably, the amount of the heteropoly acid and heteropoly acid salt supported catalyst in the step (1) is 10-50% of the mass of the 1,2, 4-trichlorobenzene.
Preferably, the strong alkali solution in the step (2) is any one of a sodium hydroxide solution, a potassium hydroxide solution, a sodium methoxide solution and a potassium tert-butoxide solution.
Preferably, the molar ratio of the 1,2, 4-trichlorobenzene to the strong base in the strong base solution in the step (2) is 1:10-1: 15.
Preferably, the retention time of the hydrolysis reaction in step (2) is 30 to 150 s.
Preferably, the pressure of the hydrolysis reaction in the step (2) is 0.5 to 1 MPa.
Preferably, the temperature of the acidification reaction in the step (3) is 50-80 ℃.
(III) advantageous effects
The invention provides a continuous synthesis method of 2, 5-dichlorophenol, which has the following beneficial effects:
(1) the method of the invention uses 1,2, 4-trichlorobenzene to hydrolyze to obtain the 2, 5-dichlorophenol route, compared with the existing diazotization route, the method has the advantages of simple process operation, high safety, capability of avoiding the generation of a large amount of waste water in the diazotization reaction, and high quality and yield of the final product.
(2) The hydrolysis reaction is carried out by adopting the fixed bed reactor, so that the continuous production can be realized, the reaction time is reduced, the continuity and the safety of the production are improved, and the method is more suitable for the future continuous industrial production.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
the catalyst is Pd-H4SiW12O40/SiO218.15g of the mixture is fixed on a fixed bed reactor, 181.5g of 1,2, 4-trichlorobenzene and 1000g of 40 percent sodium hydroxide solution are respectively pumped into the fixed bed reactor by a pump to carry out hydrolysis reaction, the reaction temperature is controlled to be 100 ℃, the pressure is 0.5MPa, the retention time of the fixed bed reactor is controlled to be 30s by adjusting the pump speed, hydrolysate enters a tubular reactor, 1060g of 31 percent hydrochloric acid is pumped into the tubular reactor to carry out acidification reaction to obtain an acidification liquid, a water layer is separated from the acidification liquid, 145.2g of 2, 5-dichlorophenol is obtained by distilling and purifying an oil layer, the content is 99.1 percent, and the yield is 88.3 percent.
Example 2:
the catalyst is Pd-H4SiMo12O40/SiO2Fixing 90.75g of the hydrolysate on a fixed bed reactor, pumping 181.5g of 1,2, 4-trichlorobenzene and 1000g of 60 percent sodium hydroxide solution into the fixed bed reactor by a pump respectively for hydrolysis reaction, controlling the reaction temperature to be 100 ℃, the pressure to be 0.5MPa, adjusting the pump speed to control the retention time of the fixed bed reactor to be 60s, feeding the hydrolysate into a tubular reactor, pumping 1060g of 31 percent hydrochloric acid into the tubular reactor for hydrolysis reactionAnd carrying out acidification reaction to obtain an acidified solution, separating a water layer from the acidified solution, and distilling and purifying an oil layer to obtain 147.3g of 2, 5-dichlorophenol, wherein the content is 99.3%, and the yield is 89.7%.
Example 3:
the catalyst is Pd-H3PSiW12O40/SiO2Fixing 50g of the mixture on a fixed bed reactor, pumping 181.5g of 1,2, 4-trichlorobenzene and 1000g of 60 percent potassium hydroxide solution into the fixed bed reactor by a pump respectively for hydrolysis reaction, controlling the reaction temperature to be 100 ℃, the pressure to be 0.5MPa, adjusting the pump speed to control the retention time of the fixed bed reactor to be 90s, feeding hydrolysate into a tubular reactor, pumping 1060g of 31 percent hydrochloric acid into the tubular reactor for acidification reaction to obtain an acidified solution, removing a water layer, distilling and purifying an oil layer to obtain 148.7g of 2, 5-dichlorophenol, wherein the content is 99.2 percent, and the yield is 90.5 percent
Example 4:
the catalyst is Pd-H3PSiMo12O40/SiO2Fixing 65g of the mixture on a fixed bed reactor, pumping 181.5g of 1,2, 4-trichlorobenzene and 1000g of 70% potassium hydroxide solution into the fixed bed reactor by using a pump to perform hydrolysis reaction, controlling the reaction temperature to be 100 ℃, the pressure to be 0.5MPa, adjusting the pump speed to control the retention time of the fixed bed reactor to be 120s, feeding hydrolysate into a tubular reactor, pumping 1060g of 31% hydrochloric acid into the tubular reactor to perform acidification reaction to obtain an acidified solution, removing a water layer from the acidified solution, and performing distillation and purification on an oil layer to obtain 148.2g of 2, 5-dichlorophenol with the content of 99.1% and the yield of 90.1%.
Example 5:
the catalyst is Pd-H4SiMo12O40/SiO2Fixing 35g of the mixture on a fixed bed reactor, pumping 181.5g of 1,2, 4-trichlorobenzene and 1000g of 54% sodium methoxide solution into the fixed bed reactor by using a pump to perform hydrolysis reaction, controlling the reaction temperature to be 125 ℃ and the pressure to be 0.5MPa, adjusting the pump speed to control the retention time of the fixed bed reactor to be 90s, pumping 1060g of 31% hydrochloric acid into the tubular reactor to perform acidification reaction to obtain an acidified solution, removing a water layer from the acidified solution, and distilling and purifying an oil layer to obtain 149.1g of 2, 5-dichlorophenol with the content of 99.2% and the yield of 90.7%.
Example 6:
the catalyst is Pd-H3PSiMo12O40/SiO2Fixing 20g of the mixture on a fixed bed reactor, pumping 181.5g of 1,2, 4-trichlorobenzene and 1000g of 80% sodium methoxide solution into the fixed bed reactor by using a pump respectively to perform hydrolysis reaction, controlling the reaction temperature to be 150 ℃ and the pressure to be 0.5MPa, adjusting the pump speed to control the retention time of the fixed bed reactor to be 90s, feeding hydrolysate into a tubular reactor, pumping 1060g of 31% hydrochloric acid into the tubular reactor to perform acidification reaction to obtain an acidified solution, removing a water layer, and performing distillation and purification on an oil layer to obtain 145.9g of 2, 5-dichlorophenol, wherein the content is 99.7% and the yield is 89.2%.
Example 7:
the catalyst is Pd-H4SiW12O40/SiO2Fixing 80g of the mixture on a fixed bed reactor, pumping 181.5g of 1,2, 4-trichlorobenzene and 2000g of 56% potassium tert-butoxide solution into the fixed bed reactor by a pump respectively for hydrolysis reaction, controlling the reaction temperature to be 120 ℃, the pressure to be 0.75MPa, adjusting the pump speed to control the retention time of the fixed bed reactor to be 90s, feeding hydrolysate into a tubular reactor, pumping 1060g of 31% hydrochloric acid into the tubular reactor for acidification reaction to obtain an acidified solution, removing a water layer from the acidified solution, and distilling and purifying an oil layer to obtain 148.5g of 2, 5-dichlorophenol, wherein the content is 99.5% and the yield is 90.6%.
Example 8:
the catalyst is Pd-H4SiW12O40/SiO2Fixing 80g of the mixture on a fixed bed reactor, pumping 181.5g of 1,2, 4-trichlorobenzene and 2000g of 80% potassium tert-butoxide solution into the fixed bed reactor by a pump respectively for hydrolysis reaction, controlling the reaction temperature to be 120 ℃ and the pressure to be 1MPa, adjusting the pump speed to control the retention time of the fixed bed reactor to be 90s, pumping 1060g of 31% hydrochloric acid into the tubular reactor for acidification reaction to obtain an acidified solution, removing a water layer, and distilling and purifying an oil layer to obtain 148.7g of 2, 5-dichlorophenol, the content of which is 99.3%, and the yield of which is 90.5%.
Example 9:
the catalyst is Pd-H4SiW12O40/SiO250g of the reaction solution was fixed to a fixed bed reactor,181.5g of 1,2, 4-trichlorobenzene and 2000g of 45 percent potassium tert-butoxide solution are respectively pumped into a fixed bed reactor by a pump to carry out hydrolysis reaction, the reaction temperature is controlled to be 120 ℃, the pressure is 0.5MPa, the retention time of the fixed bed reactor is controlled to be 90s by adjusting the pump speed, hydrolysate enters a tubular reactor, 1060g of 31 percent hydrochloric acid is pumped into the tubular reactor to carry out acidification reaction, an acidified solution is obtained, a water layer is separated, 147.1g of 2, 5-dichlorophenol with the content of 99.6 percent is obtained by distilling and purifying an oil layer, and the yield is 89.8 percent.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising an … …" does not exclude the presence of other identical elements in a process, method, article, or apparatus that comprises the element.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (7)
1. A continuous synthesis method of 2, 5-dichlorophenol is characterized by comprising the following steps:
(1) loading heteropoly acid and heteropoly acid salt supported catalyst onto fixed bed reactor, whereinThe heteropoly acid and heteropoly acid salt supported catalyst is Pd-H4SiW12O40/SiO2、Pd-H4SiMo12O40/SiO2、Pd-H3PSiW12O40/SiO2And Pd-H3PSiMo12O40/SiO2One or more of the above;
(2) pumping 1,2, 4-trichlorobenzene and strong alkali solution into a fixed bed reactor for hydrolysis reaction;
(3) after the hydrolysis reaction is finished, pumping the reaction liquid and hydrochloric acid into a tubular reactor for acidification reaction, and removing a water layer from the obtained acidification liquid after the reaction is completed;
(4) and distilling and purifying the organic layer to obtain the 2, 5-dichlorophenol.
2. The continuous synthesis method of 2, 5-dichlorophenol according to claim 1, wherein the amount of the heteropoly acid and heteropoly acid salt supported catalyst used in step (1) is 10-50% of the mass of 1,2, 4-trichlorobenzene.
3. The continuous synthesis method of 2, 5-dichlorophenol according to claim 1, wherein the strong alkali solution in step (2) is any one of sodium hydroxide solution, potassium hydroxide solution, sodium methoxide solution, and potassium tert-butoxide solution.
4. The continuous synthesis method of 2, 5-dichlorophenol according to claim 1, wherein the molar ratio of 1,2, 4-trichlorobenzene to strong base in the strong base solution in step (2) is 1:10 to 1: 15.
5. The continuous synthesis process of 2, 5-dichlorophenol according to claim 1, wherein the retention time of the hydrolysis reaction in step (2) is from 30s to 150 s.
6. The continuous synthesis method of 2, 5-dichlorophenol according to claim 1, wherein the hydrolysis reaction pressure in the step (2) is 0.5-1 MPa.
7. The continuous synthesis method of 2, 5-dichlorophenol according to claim 1, wherein the temperature of the acidification reaction in the step (3) is 50-80 ℃.
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