CN117865799A - Continuous synthesis method and system of chloroacetyl chloride - Google Patents
Continuous synthesis method and system of chloroacetyl chloride Download PDFInfo
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- CN117865799A CN117865799A CN202311783817.6A CN202311783817A CN117865799A CN 117865799 A CN117865799 A CN 117865799A CN 202311783817 A CN202311783817 A CN 202311783817A CN 117865799 A CN117865799 A CN 117865799A
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- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 238000001308 synthesis method Methods 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 235
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 57
- 229940106681 chloroacetic acid Drugs 0.000 claims abstract description 57
- 239000007788 liquid Substances 0.000 claims abstract description 56
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000003054 catalyst Substances 0.000 claims abstract description 54
- 239000002808 molecular sieve Substances 0.000 claims abstract description 38
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002841 Lewis acid Substances 0.000 claims abstract description 33
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000002844 melting Methods 0.000 claims abstract description 18
- 230000008018 melting Effects 0.000 claims abstract description 18
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 238000005917 acylation reaction Methods 0.000 claims abstract description 5
- 230000010933 acylation Effects 0.000 claims abstract 2
- 239000007789 gas Substances 0.000 claims description 65
- 238000010517 secondary reaction Methods 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 238000001354 calcination Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 238000009210 therapy by ultrasound Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 16
- 238000011049 filling Methods 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 208000012839 conversion disease Diseases 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 238000005086 pumping Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000012320 chlorinating reagent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- -1 preferably Chemical compound 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a continuous synthesis method and a system of chloroacetyl chloride, wherein the method comprises the steps of filling spherical molecular sieve MCM-22 catalyst with immobilized Lewis acid in two-stage reaction towers, carrying out continuous acylation reaction on chloroacetic acid and phosgene under the action of the catalyst, and carrying out nitrogen light removal on an acylation liquid in a light removal tower to obtain a chloroacetyl chloride product, wherein the chloroacetic acid conversion rate is more than or equal to 99.8%, the chloroacetic acid content is more than or equal to 99%, the yield is more than or equal to 97%, and the dichloroacetyl chloride content is less than or equal to 0.3%. The system comprises a first-stage reaction tower, a second-stage reaction tower, a light-expelling tower, a melting kettle and a gas-liquid separator. The continuous synthesis method has the advantages of good catalyst activity, high reaction conversion rate, low phosgene consumption, repeated use of the catalyst and the like, effectively saves the production cost, has small liquid holdup of a reaction system, low reaction risk and few byproducts, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of fine chemical preparation, and particularly relates to a continuous synthesis method and system of chloroacetyl chloride.
Background
Chloroacetyl chloride is an important organic intermediate, english name: chloroacetyl Chloride, molecular formula: c (C) 2 H 2 Cl 2 O, relative molecular weight mass 112.94. The chloracetyl chloride is mainly applied to the field of pesticides, downstream products of the chloracetyl chloride comprise amide herbicides, organophosphorus pesticides, systemic bactericides and the like, and the chloracetyl chloride can be used for synthesizing medicaments for treating diabetes, anti-inflammatory analgesics and the like in the pharmaceutical industry, and in addition, the chloracetyl chloride can also be derived into a plurality of series of fine chemicals, so that the use is wide.
The chloroacetyl chloride has a plurality of synthetic routes, but the synthetic routes with industrialized prospect mainly comprise four methods of an acetic acid chlorination method, a chloroacetic acid method, a ketene method and an acetyl chloride method. Acetic acid chloridizing method uses acetic acid as raw materialThe material reacts with chlorine under the action of a catalyst to obtain the chloroacetyl chloride. British patent document GB1125772A reports a composition of the formula S 2 Cl 2 -FeCl 3 The method for preparing the chloroacetyl chloride by using the catalyst has the advantages of low purity of the product, low total yield and more byproducts. The chloroacetic acid method uses chloroacetic acid as raw material, and makes it react with chlorinating agent to obtain chloroacetyl chloride, and the chlorinating agent mainly includes chlorine gas, phosgene and thionyl chloride. U.S. patent document No. US3636102A reports that chloroacetic acid is used as a raw material in S 2 Cl 2 The method for preparing the chloroacetyl chloride by reacting with chlorine under catalysis has the problems that the impurity dichloroacetyl chloride is difficult to control, and the product contains impurity sulfur and is difficult to separate. Fan Zuen in the synthesis of chloroacetyl chloride by the phosgene method (Liaoning chemical industry, 1992, 5 (5): 50-51), it is reported that chloroacetic acid and phosgene are introduced from the bottom in a reactor, and the chloroacetyl chloride is continuously synthesized under the action of catalyst metal chloride, but the method requires a reaction temperature of 90-130 ℃, the molar ratio of chloroacetic acid to phosgene is 1:3.3, and the problems of overhigh reaction temperature, large energy consumption of the device, large phosgene consumption, high cost and the like exist. Thionyl chloride is slowly added into chloroacetic acid, the temperature is raised to 50-60 ℃, and chloroacetyl chloride is prepared by reaction, but a large amount of SO is generated 2 There are many three wastes and serious pollution. US3758571a reports that acetic acid is used as a raw material and triethyl phosphate is used as a catalyst, ketene is prepared after pyrolysis and dehydration, and then chloroacetyl chloride is obtained after reaction with chlorine, and the method has the problems of low product purity, high energy consumption, high equipment construction investment and the like. Chinese patent document CN109456168A reports that in a contact reactor, a lewis acid catalyst is supported by activated carbon to catalyze a reaction between gaseous acetyl chloride and chlorine to prepare chloroacetyl chloride, and in order to avoid excessive chlorination of acetyl chloride into dichloroacetyl chloride, the reaction has the problems of incomplete reaction and low conversion rate of raw material acetyl chloride, the highest conversion rate is only 89.59%, and meanwhile, the raw material acetyl chloride in the route has higher price and does not have industrial advantage.
Disclosure of Invention
The technical problem to be solved by the invention is to overcome the defects of the prior art, and provide the continuous synthesis method of the chloroacetyl chloride, which has the advantages of high product content and yield, high raw material conversion rate, less side reaction, easy control of process conditions and simple operation.
In order to solve the technical problems, the invention adopts the following technical scheme.
A continuous synthesis method of chloroacetyl chloride comprises the following steps: preparing a continuous reaction system with a first-stage reaction tower, a second-stage reaction tower and a light-expelling tower, wherein catalysts are filled in the first-stage reaction tower and the second-stage reaction tower, and the catalysts are spherical molecular sieve MCM-22 with immobilized Lewis acid; heating and melting chloroacetic acid, continuously feeding the chloroacetic acid into the first-stage reaction tower, continuously introducing phosgene into the first-stage reaction tower, wherein the molar ratio of the chloroacetic acid to the phosgene is 1:1.02-1.1, and carrying out acylation reaction on the chloroacetic acid and the phosgene under the action of the catalyst, wherein the reaction temperature is 60-80 ℃ to generate crude chloroacetyl chloride; continuously delivering the crude chloroacetyl chloride to the secondary reaction tower for continuous reaction, condensing and separating gas and liquid from tail gas generated in the primary reaction tower, delivering the obtained liquid phosgene to the secondary reaction tower for continuous reaction at the reaction temperature of 60-70 ℃, and overflowing the acylated liquid obtained in the secondary reaction tower to the light-expelling tower to obtain a chloroacetyl chloride product after light expelling.
In the above continuous synthesis method of chloroacetyl chloride, preferably, the spherical molecular sieve MCM-22 with immobilized lewis acid is prepared by the following method: dissolving Lewis acid in an organic solvent, adding spherical molecular sieve MCM-22, carrying out ultrasonic treatment for 60-90 min, heating and refluxing for 1-5 h, filtering, drying the obtained solid in vacuum, and calcining at 300-400 ℃ for 2-10 h to obtain spherical molecular sieve MCM-22 with immobilized Lewis acid; wherein the Lewis acid comprises one of tin tetrachloride and titanium tetrachloride, the organic solvent comprises one of absolute ethyl alcohol, toluene and chloroform, and the mass ratio of the Lewis acid to the spherical molecular sieve MCM-22 is 0.05-0.1:1.
In the continuous synthesis method of chloroacetyl chloride, preferably, the total mass of the catalyst in the first-stage reaction tower and the second-stage reaction tower accounts for 3% -5% of the total mass of chloroacetic acid fed, and the mass ratio of the catalyst in the first-stage reaction tower to the catalyst in the second-stage reaction tower is 3:2.
In the continuous synthesis method of chloroacetyl chloride, preferably, the residence time of the reaction materials in the continuous reaction system is 0.5-2 h.
In the above-mentioned continuous synthesis method of chloroacetyl chloride, preferably, nitrogen is introduced into the light-expelling tower to expel light, and the light-expelling temperature in the light-expelling tower is 30-50 ℃.
According to the continuous synthesis method of the chloroacetyl chloride, preferably, the content of the chloroacetyl chloride product is more than or equal to 99%, the yield is more than or equal to 97%, and the content of the dichloroacetyl chloride is less than or equal to 0.3%.
The invention also provides a continuous synthesis system of chloracetyl chloride, which comprises a first-stage reaction tower, a second-stage reaction tower, a light expelling tower, a melting kettle and a gas-liquid separator, wherein catalysts are filled in the first-stage reaction tower and the second-stage reaction tower, the catalysts are spherical molecular sieves MCM-22 with Lewis acid being immobilized, the first-stage reaction tower is provided with a first feed inlet, a second feed inlet, a discharge port and a first tail gas outlet, the second-stage reaction tower is provided with a third feed inlet, a fourth feed inlet and an overflow port, the melting kettle is communicated with the first feed inlet, the discharge port is communicated with the third feed inlet, the first tail gas outlet is communicated with an air inlet of the gas-liquid separator, the liquid outlet of the gas-liquid separator is communicated with the fourth feed inlet, the light expelling tower is provided with a fifth feed inlet and a discharge port, and the overflow port is communicated with the fifth feed inlet.
In the continuous synthesis system of chloroacetyl chloride, preferably, the second-stage reaction tower is provided with a second tail gas outlet, and the second tail gas outlet is communicated with the first tail gas condenser.
In the continuous synthesis system of chloroacetyl chloride, preferably, the light expelling tower is provided with a nitrogen inlet and a third tail gas outlet, and the third tail gas outlet is communicated with the second tail gas condenser.
In the invention, the feed rates of chloroacetic acid and phosgene can be obtained by calculating the material proportion and the residence time of a reaction system in a corresponding tower.
The main innovation point of the invention is that:
in the prior art, when chlorine is taken as a chlorinating agent to react with chloroacetic acid or acetyl chloride and the like to prepare chloroacetyl chloride, alpha-H connected with carbon atoms is inevitably replaced by Cl atoms to generate byproduct dichloroacetyl chloride, so that the quality of products is affected; while phosgene is taken as a chlorinating agent, the generation of byproduct dichloroacetyl chloride can be inhibited, but a catalyst is added to react, such as a Lewis acid metal catalyst, and a large amount of phosgene is introduced at a higher temperature to ensure high conversion rate, so that the consumption of the phosgene is larger and the production cost is higher. Meanwhile, the tail gas of the first-stage reaction tower is subjected to gas-liquid separation, condensed liquid phosgene is returned to the second-stage reaction tower for mechanically applying reaction, so that the phosgene concentration of the second-stage reaction tower is improved, and chloroacetic acid in the later stage of reaction is completely converted. The method can effectively reduce the consumption of phosgene, inhibit byproducts, improve the conversion rate, save the production cost and improve the product quality.
Compared with the prior art, the invention has the advantages that:
(1) The invention realizes the continuous production of preparing chloracetyl chloride by taking phosgene as a chlorinating agent, has simple operation method and small liquid holdup of a reaction system, reduces the reaction risk, inhibits the generation of byproducts and has the advantage of industrial production.
The invention adopts the immobilized Lewis acid catalyst (namely the spherical molecular sieve MCM-22 immobilized with Lewis acid), has high specific surface area and regular pore canal structure, activates catalytic performance, and is used as a continuous reaction tower filler, thereby improving mass transfer capacity, being beneficial to full contact of materials, being capable of obtaining faster reaction rate at the reaction temperature of 60-80 ℃, having mild reaction temperature and high phosgene utilization rate; meanwhile, the liquid phosgene recovered from the tail gas of the first-stage reaction tower is used mechanically, so that the concentration of phosgene in the second-stage reaction tower is ensured, the final chloroacetic acid is completely converted, the consumption of the whole phosgene is reduced, the chloroacetic acid conversion rate can reach more than 99.8% when the minimum 1.02eq of phosgene is calculated, the product content after light removal is more than or equal to 99%, the yield is more than or equal to 97%, and the dichloroacetyl chloride is less than or equal to 0.3%.
(2) The catalyst adopted by the invention has good reusability, and the chloroacetic acid conversion rate is still up to more than 99.5% after 8 times of catalytic circulation.
Drawings
FIG. 1 is a schematic diagram of a continuous synthesis system for chloroacetyl chloride employed in examples 1-5 of the present invention.
Legend description:
1. a first-stage reaction tower; 2. a second-stage reaction tower; 3. a light-driving tower; 4. a melting kettle; 5. a first feed port; 6. a second feed inlet; 7. a discharge port; 8. a first tail gas outlet; 9. a third feed inlet; 10. a fourth feed inlet; 11. an overflow port; 12. a second tail gas outlet; 13. a fifth feed inlet; 14. a nitrogen inlet; 15. a feed opening; 16. a third tail gas outlet; 17. a gas-liquid separator; 18. a first tail gas condenser; 19. and a second tail gas condenser.
Detailed Description
The invention is further described below in connection with the drawings and the specific preferred embodiments, but the scope of protection of the invention is not limited thereby. The raw materials and instruments used in the examples below are all commercially available. The density of chloroacetic acid was 1.58g/mL, and the density of the acylating solution was about 1.40g/mL.
In the following embodiments, as shown in fig. 1, the adopted continuous synthesis system of chloroacetyl chloride comprises a first-stage reaction tower 1, a second-stage reaction tower 2, a light expelling tower 3, a melting kettle 4 and a gas-liquid separator 17, wherein the towers of the first-stage reaction tower 1 and the second-stage reaction tower 2 are filled with catalysts serving as fillers, the catalysts are spherical molecular sieves MCM-22 for immobilizing Lewis acid, the first-stage reaction tower 1 is provided with a first feed port 5, a second feed port 6, a discharge port 7 and a first tail gas outlet 8, the first feed port 5 is a chloroacetic acid feed port, the second feed port 6 is a phosgene feed port, the second-stage reaction tower 2 is provided with a third feed port 9, a fourth feed port 10 and an overflow port 11, the fourth feed port 10 is arranged at the bottom of the side wall of the second-stage reaction tower 2 and is a liquid phosgene feed port, the melting kettle 4 is communicated with the first feed port 5, the discharge port 7 is communicated with the third feed port 9, the first tail gas outlet 8 is communicated with the gas inlet of the gas-liquid separator 17, the liquid outlet of the gas-liquid separator 17 is communicated with the fourth feed port 10 and the overflow port 13 is provided with the fifth feed port 13, and the fifth feed port 13 is communicated with the overflow port 13.
In the continuous synthesis system, the secondary reaction tower 2 is provided with a second tail gas outlet 12, and the second tail gas outlet 12 is communicated with a first tail gas condenser 18.
In the continuous synthesis system, a light expelling tower 3 is provided with a nitrogen inlet 14 and a third tail gas outlet 16, and the third tail gas outlet 16 is communicated with a second tail gas condenser 19.
In the continuous synthesis system, jackets are arranged in a primary reaction tower 1, a secondary reaction tower 2 and a light-expelling tower 3, and a melting kettle 4 is provided with a jacket and a stirring device.
In the continuous synthesis system, a gas-liquid separator 17 is used for separating tail gas (comprising phosgene, HCl gas and CO) at the top of the first-stage reaction tower 1 2 Gas) and gas-liquid separation, the liquid phosgene obtained by condensation is sent to a second-stage reaction tower 2 through a fourth feed inlet 10, and HCl gas and CO 2 The gas is discharged as tail gas; the gas inlet of the first tail gas condenser 18 is communicated with the second tail gas outlet 12 of the secondary reaction tower 2, and the gas inlet of the second tail gas condenser 19 is communicated with the third tail gas outlet 16 of the light expelling tower 3, so that a small amount of products possibly carried along with the gas at the top of the tower are condensed by the condenser and then returned to the tower, and the yield is increased.
The working principle of the continuous synthesis system is as follows:
chloroacetic acid is heated and melted by a melting kettle 4 and then is respectively introduced into a first-stage reaction tower 1 through a first feed inlet 5 and a second feed inlet 6 at the same time for reaction, crude chloroacetyl chloride obtained by the reaction enters a second-stage reaction tower 2 through a discharge outlet 7 and a third feed inlet 9 for continuous reaction, tail gas at the top of the first-stage reaction tower 1 is sent into a gas-liquid separator 17 through a first tail gas outlet 8, and condensed liquid phosgene, HCl gas and CO are subjected to reaction 2 Gas-liquid separation of gasThe separated liquid phosgene is sent to the secondary reaction tower 2 for continuous reaction so as to increase the phosgene concentration of the secondary reaction tower 2. The acylated liquid overflows into the light-expelling tower 3 through the fifth feeding port 13, nitrogen is introduced into the light-expelling tower 3 through the nitrogen inlet 14 for light expelling, and products possibly carried along with gas in the secondary reaction tower 2 and the light-expelling tower 3 are condensed respectively through the first tail gas condenser 18 and the second tail gas condenser 19 and then returned to the tower, so that the yield is increased.
Example 1
The invention relates to a continuous synthesis method of chloroacetyl chloride, which comprises the following steps:
the method comprises the steps of filling spherical molecular sieve MCM-22 catalyst with a filler for supporting Lewis acid in a first-stage reaction tower 1 (phi 40mm, H600 mm) and a second-stage reaction tower 2 (phi 40mm, H400 mm), wherein the total consumption of the catalyst is 300g, heating and melting chloroacetic acid, pumping the chloroacetic acid into the first-stage reaction tower 1 from a first feed port 5 at the top of the first-stage reaction tower 1 at a speed of 1mL/min, introducing phosgene into the first-stage reaction tower 1 from a second feed port 6 at the bottom of the first-stage reaction tower 1 at a speed of 1.69g/min, namely, the molar ratio of chloroacetic acid to phosgene is 1:1.02, controlling the reaction temperature of the first-stage reaction tower 1 to be 60 ℃, continuously feeding the obtained crude chloroacetyl chloride into the second-stage reaction tower 2 through a discharge port 7 and a third feed port 9, continuously reacting the liquid phosgene obtained after the top tail gas-liquid separation of the first-stage reaction tower 1 enters the second-stage reaction tower 2 from a fourth feed port 10, continuously reacting, the obtained acylated liquid overflows from the top of the second-stage reaction tower 2 to a second-stage reaction tower 3 (phi 40 ℃ at a temperature of 60 ℃ and a total temperature of 3 mm), introducing the obtained acylated liquid into a glass-stage reaction tower 3 from the top of the second-stage reaction tower 3 (phi 40mm, the whole system is filled with a full of the glass, and flowing into a system for a chlorine-removing reaction system from the first-stage reaction tower 3, and continuously reacting at a reaction tower at a temperature of chlorine-removing system of 15 mm, and continuously flowing under the condition under the conditions of the conditions is 15 h, and flowing down from the chlorine reaction tower is continuously at the reaction tower at a temperature is continuously flowing at the bottom kettle, and at a temperature is discharged from the bottom reaction tower kettle is continuously at a temperature and at a temperature. The system stably and continuously runs for 105 hours, multi-period analysis is randomly selected (taking 1 hour as a unit and taking the average value of the following parameters), the chloroacetic acid conversion rate is 99.82%, the chloroacetyl chloride content is 99.31%, the yield is 97.56%, and the dichloroacetyl chloride content is less than or equal to 0.3%.
In this example, the spherical molecular sieve MCM-22 with immobilized Lewis acid is prepared by the following method:
dissolving 15g of anhydrous titanium tetrachloride in 500g of absolute ethyl alcohol, adding 300g of spherical molecular sieve MCM-22, carrying out ultrasonic treatment for 60min, heating and refluxing for 1h, filtering and recovering the ethanol, drying the solid under vacuum condition, and calcining at 300 ℃ for 2h to obtain the spherical molecular sieve MCM-22 immobilized with Lewis acid.
In this example, the total mass of the catalyst in the first-stage reaction tower 1 and the second-stage reaction tower 2 accounts for 3% of the total mass of chloroacetic acid feed, and the mass ratio of the catalyst in the first-stage reaction tower 1 to the catalyst in the second-stage reaction tower 2 is 3:2.
Example 2
The invention relates to a continuous synthesis method of chloroacetyl chloride, which comprises the following steps:
the method comprises the steps of filling spherical molecular sieve MCM-22 catalyst with a filler for supporting Lewis acid in a first-stage reaction tower 1 (phi 40mm, H600 mm) and a second-stage reaction tower 2 (phi 40mm, H400 mm), wherein the total consumption of the catalyst is 300g, heating and melting chloroacetic acid, pumping the chloroacetic acid into the first-stage reaction tower 1 from a first feed port 5 at the top of the first-stage reaction tower 1 at a speed of 2mL/min, simultaneously introducing phosgene into the first-stage reaction tower 1 from a second feed port 6 at the bottom of the first-stage reaction tower 1 at a speed of 3.64g/min, namely, the molar ratio of chloroacetic acid to phosgene is 1:1.1, controlling the reaction temperature of the first-stage reaction tower 1 to be 80 ℃, continuously feeding the obtained crude chloroacetyl chloride into the second-stage reaction tower 2, continuously reacting the overhead gas of the first-stage reaction tower 1 at a temperature of 70 ℃ through a fourth feed port 10, overflowing the obtained acylated liquid into a photo-expelling tower 3 (phi 40mm, H500 mm) from the top of the second-stage reaction tower 2, introducing the obtained acylated liquid into a photo-acid into a photo-expelling tower 3 (phi 40mm, introducing the photo-acid into a photo-filling system from the bottom of the photo-reactor 3 at a full temperature of the photo-reactor 3, and continuously feeding the photo-acid into a photo-reactor at a reaction tower at a temperature of 30 h, and continuously standing the photo-acid reaction system of 30, and continuously feeding the photo-acid into the bottom of the photo-reaction tower from the bottom of the photo-reactor 3, and carrying out the photo-reaction tower. During the stable and continuous operation of the system for 31 hours, multi-period analysis (taking 1 hour as a unit and taking an average value) is randomly selected, the chloroacetic acid conversion rate is 99.85%, the chloroacetyl chloride content is 99.26%, the yield is 97.23%, and the dichloroacetyl chloride content is less than or equal to 0.3%.
In this example, the spherical molecular sieve MCM-22 with immobilized Lewis acid is prepared by the following method:
dissolving 15g of anhydrous titanium tetrachloride in 500g of absolute ethyl alcohol, adding 300g of spherical molecular sieve MCM-22, carrying out ultrasonic treatment for 90min, heating and refluxing for 5h, filtering and recovering the ethanol, drying the solid under vacuum condition, and calcining at 400 ℃ for 10h to obtain the spherical molecular sieve MCM-22 immobilized with Lewis acid.
In this example, the total mass of the catalyst in the first-stage reaction tower 1 and the second-stage reaction tower 2 accounts for 5% of the total mass of the chloroacetic acid feed, and the mass ratio of the catalyst in the first-stage reaction tower 1 to the catalyst in the second-stage reaction tower 2 is 3:2.
Example 3
The invention relates to a continuous synthesis method of chloroacetyl chloride, which comprises the following steps:
filling spherical molecular sieve MCM-22 catalyst with a filler for supporting Lewis acid in a first-stage reaction tower 1 (phi 40mm, H600 mm) and a second-stage reaction tower 2 (phi 40mm, H400 mm), wherein the total consumption of the catalyst is 300g, heating and melting chloroacetic acid, pumping the chloroacetic acid into the first-stage reaction tower 1 from a first feed port 5 at the top of the first-stage reaction tower 1 at a speed of 1mL/min, simultaneously introducing phosgene into a catch-up tower 3 (phi 40mm, H500 mm) from a second feed port 6 at the bottom of the first-stage reaction tower 1 at a speed of 1.69g/min, namely, the molar ratio of chloroacetic acid to phosgene is 1:1.02, controlling the reaction temperature of the first-stage reaction tower 1 to be 60 ℃, continuously delivering the obtained crude chloroacetyl chloride into the second-stage reaction tower 2 for continuous reaction, continuously reacting the liquid phosgene obtained after the tail gas and gas are separated from the top of the first-stage reaction tower 1 into the second-stage reaction tower 2 through a fourth feed port 10, the obtained acylated liquid overflows from the top of the second-stage reaction tower 2 to a catch-up tower 3 (phi 40mm, H500 mm), the catch-up tower 3 is filled with a spring at a temperature of the whole system of the whole reaction tower is filled with nitrogen gas at a temperature of 50 ℃ and the bottom of the product is continuously carried out in the catch-up reaction tower for 15 h. During the stable and continuous operation of the system for 63 hours, multi-period analysis (taking 1 hour as a unit and taking an average value) is randomly selected, the chloroacetic acid conversion rate is 99.89%, the chloroacetyl chloride content is 99.56%, the yield is 98.12%, and the dichloroacetyl chloride content is less than or equal to 0.3%.
In this example, the spherical molecular sieve MCM-22 with immobilized Lewis acid is prepared by the following method:
30g of anhydrous tin tetrachloride is dissolved in 500g of toluene, 300g of spherical molecular sieve MCM-22 is added, ultrasonic treatment is carried out for 60min, heating reflux is carried out for 1h, toluene is recovered by filtration, the solid is dried under vacuum condition, and then calcination is carried out for 2h at 400 ℃, thus obtaining the spherical molecular sieve MCM-22 with immobilized Lewis acid.
In this example, the total mass of the catalyst in the first-stage reaction tower 1 and the second-stage reaction tower 2 accounts for 5% of the total mass of the chloroacetic acid feed, and the mass ratio of the catalyst in the first-stage reaction tower 1 to the catalyst in the second-stage reaction tower 2 is 3:2.
Example 4
The invention relates to a continuous synthesis method of chloroacetyl chloride, which comprises the following steps:
filling spherical molecular sieve MCM-22 catalyst with a filler for supporting Lewis acid in a first-stage reaction tower 1 (phi 40mm, H600 mm) and a second-stage reaction tower 2 (phi 40mm, H400 mm), heating and melting chloroacetic acid at the total dosage of 300g, pumping phosgene from a first feed port 5 at the top of the first-stage reaction tower 1 at the speed of 1mL/min, introducing phosgene from a second feed port 6 at the bottom of the first-stage reaction tower 1 at the speed of 1.82g/min, namely, the molar ratio of chloroacetic acid to phosgene is 1:1.1, controlling the reaction temperature of the first-stage reaction tower 1 to be 80 ℃, continuously conveying the obtained crude chloroacetyl chloride into the second-stage reaction tower 2 for continuous reaction, continuously reacting the liquid phosgene obtained by condensing tail gas at the top of the first-stage reaction tower 1 and separating gas from liquid into the second-stage reaction tower 2 at the reaction temperature of 60 ℃ from the top of the second-stage reaction tower 2, overflowing the obtained acylated liquid from the top of the second-stage reaction tower 2 to a light-expelling tower 3 (phi 40mm, H500 mm), introducing glass light spring into the whole system for 30 h of the reaction tower for stopping the reaction, and continuously reacting the obtained product, wherein the chlorine is introduced from the bottom of the whole system of the first-stage reaction tower 2 is subjected to the chlorine-expelling tower for 30 h. The system stably and continuously runs for 105 hours, multi-period analysis (taking 1 hour as a unit and taking an average value) is randomly selected, the chloroacetic acid conversion rate is 99.83%, the chloroacetyl chloride content is 99.35%, the yield is 97.16%, and the dichloroacetyl chloride content is less than or equal to 0.3%.
In this example, the spherical molecular sieve MCM-22 with immobilized Lewis acid is prepared by the following method:
15g of anhydrous tin tetrachloride is dissolved in 500g of chloroform, 300g of spherical molecular sieve MCM-22 is added, ultrasonic treatment is carried out for 90min, heating reflux is carried out for 1h, chloroform is recovered by filtration, the solid is dried under vacuum condition, and then calcination is carried out for 2h at 400 ℃, thus obtaining the spherical molecular sieve MCM-22 with immobilized Lewis acid.
In this example, the total mass of the catalyst in the first-stage reaction tower 1 and the second-stage reaction tower 2 accounts for 3% of the total mass of chloroacetic acid feed, and the mass ratio of the catalyst in the first-stage reaction tower 1 to the catalyst in the second-stage reaction tower 2 is 3:2.
Example 5
The invention relates to a continuous synthesis method of chloroacetyl chloride, which comprises the following steps:
filling spherical molecular sieve MCM-22 catalyst with a filler for supporting Lewis acid in a first-stage reaction tower 1 (phi 40mm, H600 mm) and a second-stage reaction tower 2 (phi 40mm, H400 mm), heating and melting chloroacetic acid at the total dosage of 300g, pumping phosgene from a first feed port 5 at the top of the first-stage reaction tower 1 at the speed of 2mL/min, simultaneously introducing phosgene from a second feed port 6 at the bottom of the first-stage reaction tower 1 at the speed of 3.64g/min, namely, the molar ratio of chloroacetic acid to phosgene is 1:1.1, controlling the reaction temperature of the first-stage reaction tower 1 to be 80 ℃, continuously conveying the obtained crude chloroacetyl chloride into the second-stage reaction tower 2 for continuous reaction, continuously reacting the liquid phosgene obtained by condensing tail gas at the top of the first-stage reaction tower 1 and separating gas from liquid into the second-stage reaction tower 2 at the reaction temperature of 70 ℃ from the top of the second-stage reaction tower 2, overflowing the obtained acylated liquid from the top of the second-stage reaction tower 2 to a light-expelling tower 3 (phi 40mm, H500 mm), filling the glass light-filled with a spring into the whole system at the temperature of 3 ℃ from the bottom of the first-stage reaction tower 3, and continuously introducing the obtained chloroacetylating liquid into the system at the bottom of the first-stage reaction tower at the temperature of 30 h, and continuously reacting the product at the time of the complete system is kept at the time of the chlorine-after the reaction tower is discharged from the top of the chlorine-3. The system stably and continuously runs for 31h, 8=248 h, multi-period analysis (taking 1h as a unit and taking an average value) is randomly selected, the catalyst is repeatedly used for 8 times, the chloroacetic acid conversion rate is 99.56%, the chloroacetyl chloride content is 99.12%, the yield is 96.43%, and the dichloroacetyl chloride content is less than or equal to 0.3%.
In this example, the spherical molecular sieve MCM-22 with immobilized Lewis acid is prepared by the following method:
dissolving 15g of anhydrous titanium tetrachloride in 500g of absolute ethyl alcohol, adding 300g of spherical molecular sieve MCM-22, carrying out ultrasonic treatment for 90min, heating and refluxing for 5h, filtering and recovering the ethanol, drying the solid under vacuum condition, and calcining at 400 ℃ for 10h to obtain the spherical molecular sieve MCM-22 immobilized with Lewis acid.
In this example, when the catalyst is used once, the total mass of the catalyst in the first-stage reaction tower 1 and the second-stage reaction tower 2 accounts for 5% of the total mass of chloroacetic acid feed, and the mass ratio of the catalyst in the first-stage reaction tower 1 to the catalyst in the second-stage reaction tower 2 is 3:2.
Comparative example 1
A continuous synthesis method of chloroacetyl chloride comprises the following steps:
filling a first-stage reaction tower 1 (phi 40mm, H600 mm) and a second-stage reaction tower 2 (phi 40mm, H400 mm) with a packing spherical molecular sieve MCM-22 (the total consumption is 300 g), heating and melting chloroacetic acid, pumping in at a speed of 2mL/min from a first feed inlet 5 at the top of the first-stage reaction tower 1, introducing phosgene at a speed of 3.64g/min from a second feed inlet 6 at the bottom of the first-stage reaction tower 1, namely, the molar ratio of chloroacetic acid to phosgene is 1:1.1, controlling the reaction temperature of the first-stage reaction tower 1 to be 80 ℃, continuously conveying the obtained crude chloroacetyl chloride to the second-stage reaction tower 2 for continuous reaction, continuously reacting the tail gas at the top of the first-stage reaction tower 1 by condensing, enabling the liquid phosgene obtained after the tail gas and liquid of the first-stage reaction tower 1 are separated by condensing and gas and liquid to enter the second-stage reaction tower 2 from a fourth feed inlet 10, overflowing the obtained acylated liquid from the top of the second-stage reaction tower 2 to a light-driving tower 3 (phi 40mm, H500 mm) at the reaction temperature of the second-stage reaction tower 2 is 70 ℃, introducing the obtained acylated liquid into a glass light-driving tower 3 from the top of the second-stage reaction tower 2 at the full temperature of the spring 3, and introducing the glass driving tower into the whole system for 30 h from the bottom of the light-driving tower to react at the packed reaction tower at the temperature of 3, and continuously flowing under the condition of the nitrogen gas is kept at the temperature of the filling system for 15 h, and continuously reacting at the time of 5h, and stopping the reaction after the reaction is continuously flowing. The system stably and continuously runs for 31 hours, and multi-period analysis (taking 1 hour as a unit and taking an average value) is randomly selected, namely the spherical molecular sieve MCM-22 accounts for 5% of the total mass percent of the chloroacetic acid feed, and the chloroacetic acid conversion rate is 1.25%.
It is obtained from this that the reaction is difficult to proceed and the chloroacetic acid conversion is very low by using only spherical molecular sieve MCM-22 as the packing of the reaction tower.
The above description is only of the preferred embodiment of the present invention, and is not intended to limit the present invention in any way. While the invention has been described in terms of preferred embodiments, it is not intended to be limiting. Any person skilled in the art can make many possible variations and modifications to the technical solution of the present invention or equivalent embodiments using the method and technical solution disclosed above without departing from the spirit and technical solution of the present invention. Therefore, any simple modification, equivalent substitution, equivalent variation and modification of the above embodiments according to the technical substance of the present invention, which do not depart from the technical solution of the present invention, still fall within the scope of the technical solution of the present invention.
Claims (10)
1. The continuous synthesis method of the chloroacetyl chloride is characterized by comprising the following steps of: preparing a continuous reaction system with a first-stage reaction tower (1), a second-stage reaction tower (2) and a light-expelling tower (3), wherein catalysts are filled in the first-stage reaction tower (1) and the second-stage reaction tower (2), and the catalysts are spherical molecular sieve MCM-22 with immobilized Lewis acid; heating and melting chloroacetic acid, continuously delivering the heated and melted chloroacetic acid into the first-stage reaction tower (1), continuously introducing phosgene into the first-stage reaction tower (1), and carrying out acylation reaction on the chloroacetic acid and the phosgene under the action of the catalyst, wherein the reaction temperature is 60-80 ℃, so as to generate crude chloroacetyl chloride; continuously delivering crude chloroacetyl chloride to the secondary reaction tower (2) for continuous reaction, condensing and separating gas and liquid from tail gas generated in the primary reaction tower (1), delivering the obtained liquid phosgene to the secondary reaction tower (2) for continuous reaction at the temperature of 60-70 ℃, and overflowing the acylated liquid obtained in the secondary reaction tower (2) to the light expelling tower (3) to obtain a chloroacetyl chloride product after light expelling.
2. The continuous synthesis method of chloroacetyl chloride according to claim 1, wherein the spherical molecular sieve MCM-22 with immobilized lewis acid is prepared by the following method: dissolving Lewis acid in an organic solvent, adding spherical molecular sieve MCM-22, carrying out ultrasonic treatment for 60-90 min, heating and refluxing for 1-5 h, filtering, drying the obtained solid in vacuum, and calcining at 300-400 ℃ for 2-10 h to obtain spherical molecular sieve MCM-22 with immobilized Lewis acid; wherein the Lewis acid comprises one of tin tetrachloride and titanium tetrachloride, the organic solvent comprises one of absolute ethyl alcohol, toluene and chloroform, and the mass ratio of the Lewis acid to the spherical molecular sieve MCM-22 is 0.05-0.1:1.
3. The continuous synthesis method of chloroacetyl chloride according to claim 1, wherein the total mass of the catalyst in the first-stage reaction tower (1) and the second-stage reaction tower (2) accounts for 3% -5% of the total mass of chloroacetic acid feed, and the mass ratio of the catalyst in the first-stage reaction tower (1) to the catalyst in the second-stage reaction tower (2) is 3:2.
4. The continuous synthesis method of chloroacetyl chloride according to claim 1, wherein the residence time of the reaction materials in the continuous reaction system is 0.5h to 2h.
5. The continuous synthesis method of chloroacetyl chloride according to any one of claims 1 to 4, wherein nitrogen is introduced into the light-expelling tower (3) to expel light, and the light-expelling temperature in the light-expelling tower (3) is 30-50 ℃.
6. The continuous synthesis method of chloroacetyl chloride according to any one of claims 1 to 4, wherein the content of chloroacetyl chloride product is not less than 99%, the yield is not less than 97%, and the content of dichloroacetyl chloride is not more than 0.3%.
7. The continuous synthesis method of chloroacetyl chloride according to any one of claims 1 to 4, wherein chloroacetic acid is introduced into the primary reaction tower (1) from the top of the primary reaction tower (1), phosgene is introduced into the primary reaction tower (1) from the bottom of the primary reaction tower (1), liquid phosgene is introduced into the secondary reaction tower (2) from the bottom of the side wall of the secondary reaction tower (2), and the acylation liquid overflows into the light-expelling tower (3) from the top of the secondary reaction tower (2).
8. The utility model provides a continuous chemical combination system of chloracetyl chloride, its characterized in that, including one-level reaction tower (1), second grade reaction tower (2), catch-up with tower (3), melting kettle (4) and vapour and liquid separator (17), all load the catalyst in one-level reaction tower (1) and the second grade reaction tower (2), the catalyst is the spherical molecular sieve MCM-22 of solid supported Lewis acid, one-level reaction tower (1) is equipped with first feed inlet (5), second feed inlet (6), discharge gate (7) and first tail gas export (8), second grade reaction tower (2) are equipped with third feed inlet (9), fourth feed inlet (10) and overflow mouth (11), melting kettle (4) with first feed inlet (5) intercommunication, discharge gate (7) with third feed inlet (9) intercommunication, first tail gas export (8) with vapour and liquid separator (17)'s air inlet, vapour and liquid separator (17) are equipped with third feed inlet (9), fourth feed inlet (10) and overflow mouth (13) are equipped with five feed inlet (13).
9. The continuous synthesis system of chloroacetyl chloride according to claim 8, wherein the secondary reaction column (2) is provided with a second tail gas outlet (12), the second tail gas outlet (12) being in communication with a first tail gas condenser (18).
10. Continuous synthesis system of chloroacetyl chloride according to claim 8 or 9, wherein the light expelling tower (3) is provided with a nitrogen inlet (14) and a third tail gas outlet, the third tail gas outlet (16) being in communication with a second tail gas condenser (19).
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