CN110711537A - Method for continuously producing ethylene sulfide - Google Patents
Method for continuously producing ethylene sulfide Download PDFInfo
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- CN110711537A CN110711537A CN201910917759.9A CN201910917759A CN110711537A CN 110711537 A CN110711537 A CN 110711537A CN 201910917759 A CN201910917759 A CN 201910917759A CN 110711537 A CN110711537 A CN 110711537A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
- B01J4/007—Feed or outlet devices as such, e.g. feeding tubes provided with moving parts
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2204/00—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices
- B01J2204/002—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices the feeding side being of particular interest
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Abstract
The invention provides a method for continuously producing ethylene sulfide, which comprises the following steps: ethylene carbonate and thiocyanate are continuously added into a continuous reactor with the temperature controlled between 90 and 140 ℃, ethylene sulfide and cyanate are generated through reaction under the stirring action, the generated ethylene sulfide is continuously discharged from a gas outlet of the reactor, liquid ethylene sulfide is obtained through condensation and separation, and the generated cyanate is continuously discharged from the bottom of the reactor. The invention improves the batch kettle type reaction in the prior art into a continuous reactor through continuous reaction, the raw materials are instantaneously reacted at the reaction temperature, the generated ethylene sulfide is rapidly separated from other substances, and the generated cyanate powder is discharged from the bottom of the reactor under the propelling of the scraping wall screw by gravity and a stirrer. The method is clean, pollution-free, stable in production index, less in manpower and beneficial to industrial scale production.
Description
Technical Field
The invention relates to a method for continuously producing ethylene sulfide.
Background
At present, the main flow process route for producing diethylaminoethanethiol in China is to react ethylene carbonate and thiocyanate to generate thiirane, and then react diethylamine and thiirane to generate the diethylaminoethanethiol.
The same improvement is made on the method for preparing the ethylene sulfide in two patents of CN201710497589 and CN201710497588, and the yield of the ethylene sulfide is improved by adopting an intermittent feeding mode and controlling the reaction speed and the effective separation of a product and carbon dioxide. The ethylene carbonate reacts with thiocyanate to generate ethylene sulfide, the ethylene carbonate is liquid during the reaction, the thiocyanate is solid, the ethylene carbonate is both a reaction raw material and a solvent phase, and the thiocyanate and the ethylene carbonate are fully mixed for reaction through continuous stirring.
The applicant has found through research that the methods of the two patents still have certain technical defects. Cyanate has certain commercial value, but in the production process of the ethylene sulfide, the byproduct cyanate forms greasy dirt-like hard blocks at the bottom of the tank due to high temperature and is difficult to treat. The current industrialized treatment mode is to add water for high-temperature dissolution and repeatedly clean the reaction tank. The cyanate is further decomposed into carbonate, ammonium carbonate and the like in the process of adding water and heating for dissolution to form high-salt, high-COD and high-ammonia nitrogen wastewater, and the dissolving process is accompanied by pungent smell, so that the odor pollution is serious, the production site environment is very poor, the wastewater is extremely difficult to treat and is not beneficial to clean production, and meanwhile, the cyanate decomposition treatment with commercial value is contrary to the development concept of circular economy. In addition, the yield and quality of the product fractions still fluctuate due to manual batch operation, and the batch feeding causes high labor cost, which is not favorable for large-scale production.
Therefore, the development of a clean and pollution-free production method of the ethylene sulfide, which has stable production indexes and less manpower and is beneficial to industrial scale amplification, is urgently needed.
Disclosure of Invention
Therefore, the invention aims to provide a clean and pollution-free production method of the episulfide ethane, which has stable production indexes and less manpower and is beneficial to industrial scale amplification, aiming at the problems that the existing episulfide ethane production process has difficulty in processing by-product cyanate and high product yield, quality fluctuation and labor cost caused by intermittent feeding.
The invention provides a method for continuously producing ethylene sulfide, which comprises the following steps: ethylene carbonate and thiocyanate are continuously added into a continuous reactor with the temperature controlled between 90 and 140 ℃, ethylene sulfide and cyanate are generated through reaction under the stirring action, the generated ethylene sulfide is continuously discharged from a gas outlet of the reactor, liquid ethylene sulfide is obtained through condensation and separation, and the generated cyanate is continuously discharged from the bottom of the reactor.
According to the method provided by the invention, the ethylene carbonate enters the continuous reactor after being atomized by the atomizer, so that the ethylene carbonate is fully mixed and completely reacted. Preferably, the particle size of the thiocyanate powder is 10-200 meshes.
In one embodiment of the present invention, referring to fig. 1, thiocyanate and ethylene carbonate are fed into the continuous reactor 1 from a feeding tank 2 and a holding tank 3, respectively, preferably, the molar ratio of the thiocyanate and the ethylene carbonate is controlled to be about 1:1, for example, 1:0.9 to 1.1, preferably 1:0.95 to 1.05, more preferably 1:0.98 to 1.02, and most preferably 1: 1. Ethylene carbonate and thiocyanate are respectively continuously injected into a continuous reactor in a small drop shape and a small particle shape for rapid reaction, generated gases (ethylene sulfide and carbon dioxide) are continuously discharged through an outlet at the upper end of the reactor, the ethylene sulfide is separated and condensed to a storage tank, and generated solid by-product cyanate is continuously discharged through an outlet at the lower end of the reactor under the action of gravity and stirring and collected to the storage tank.
In a preferred embodiment of the present invention, the method comprises:
preheating the continuous reactor 1 to 90-140 ℃, enabling thiocyanate powder in the feeding tank 1 to enter the continuous reactor 1, and simultaneously enabling ethylene carbonate in the heat-preservation storage tank 3 to be atomized by the liquid atomizer 7 and then added into the continuous reactor 1; gas generated in the continuous reactor 1 sequentially enters a condenser and a gas-liquid separator through pipelines and is collected in a liquid collector to obtain ethylene sulfide, and meanwhile cyanate generated in the continuous reactor 1 is scraped from the inner wall of the continuous reactor 1 by a scraper 5 and enters a solid waste collector 4.
Preferably, the process provided by the present invention operates with a plant for the continuous production of ethylene sulphide, comprising, with reference to figure 1:
the continuous reaction is carried out in a reactor 1,
a feeding tank 2 and a heat preservation storage tank 3 which are connected with the upper end of the continuous reactor 1,
a solid waste collector 4 connected with the lower end of the continuous reactor 1,
a condenser and a gas-liquid separator which are connected with an air outlet at the upper end of the continuous reactor 1,
wherein, a scraper 5 contacting with the inner wall of the continuous reactor 1 is arranged in the continuous reactor 1, and the outer surface of the lower end of the continuous reactor 1 can also be provided with an oscillator 6; and a liquid atomizer 7 can be arranged between the heat-preservation storage tank 3 and the continuous reactor 1.
According to the method provided by the present invention, preferably, the method may further comprise collecting the cyanate in the solid waste collector 4. Preferably, the temperature of the solid waste collector 4 is kept between 20 and 30 ℃. Preferably, the process further comprises refining the cyanate withdrawn from the bottom of the continuous reactor with methanol to obtain a pure cyanate. Preferably, the process may further comprise recovering methanol used to purify the cyanate.
According to the method provided by the invention, the continuous reaction 1 is preferably cylindrical or inverted frustum-shaped, the diameter of the lower surface of the continuous reaction 1 is smaller than that of the upper surface of the continuous reaction 1, the continuous reaction 1 is preferably inverted frustum-shaped, and the ratio of the radius of the upper top of the inverted frustum-shaped to the height of the inverted frustum-shaped can be 1: 5-10, and is preferably 1: 8-9. Wherein, the radius of the upper top refers to: maximum radius of the upper end of the continuous reactor 1. The continuous reactor 1 is in an inverted frustum shape, the diameter of the lower surface is smaller than that of the upper surface, and solid byproducts generated in the reaction can be continuously discharged from the bottom end of the reactor.
Preferably, a liquid delivery pump may be provided between the holding tank 3 and the liquid atomizer 7.
In order to achieve a better cyanate scraping effect and at the same time to provide a stirring effect for the reactants, the scraper 5 is preferably a screw type scraper. Preferably, a meter is arranged on the connecting pipeline of the feeding tank 2 and the heat preservation storage tank 3 which are respectively connected with the continuous reactor 1.
Preferably, the connecting pipelines of the feeding tank 2 of thiocyanate and the heat-preservation storage tank 3 of ethylene carbonate respectively connected with the continuous reactor 1 are provided with one-way valves, and the solid waste collector 4 for receiving cyanate adopts a sealing device to prevent generated gas from leaking.
Preferably, the ethylene carbonate holding tank 3 and the continuous reactor 1 are provided with jacketed heating means. The solid waste collecting tank 4 is provided with a cooling device with a clamping sleeve, and the collecting tank 4 keeps the temperature below 30 ℃ in the process of continuously collecting the solid waste. In the apparatus, a vibrator 6 is used to continuously vibrate the outlet of the continuous reactor 1 to prevent solid waste powder from clogging the outlet.
The application has the advantages that: 1. by simple arrangement, continuous production of the ethanethiol is realized by utilizing a reactor with upper and lower openings, the pollution is reduced, and a high-value byproduct is obtained; 2. the scraper in the reactor is skillfully utilized, so that the cyanate is continuously scraped; 3. because of the danger of ethylene sulfide, the safe use mode in the actual production is that the ethylene sulfide is produced and used immediately, and a large amount of long-time storage is avoided. The equipment and the method of the invention carry out reaction according to the theoretical molar ratio, thus reducing the material cost; the method avoids the generation of wastewater with three high contents, avoids the production fluctuation (quality, yield and cost), is easy to enlarge and scale, improves the production environment, reduces the labor cost and the like.
Drawings
Embodiments of the invention are described in detail below with reference to the attached drawing figures, wherein:
FIG. 1 is a schematic diagram of a continuous production apparatus for ethylene sulfide provided by the present invention.
Detailed Description
The present invention is described in further detail below with reference to specific embodiments, which are given for the purpose of illustration only and are not intended to limit the scope of the invention. The present application only shows a specific reactor configuration, and in fact, the present application is not limited to the use of the reactor disclosed in the present application to perform continuous reaction, and a reactor capable of achieving similar effects can be used to achieve continuous production of ethylene sulfide by using the method described in the present application.
Example 1
This example used the process of the present invention to produce ethylene sulfide.
Referring to the apparatus for continuously producing ethylene sulfide shown in FIG. 1, the continuous reactor 1 has an inverted conical shape (the ratio of the radius of the upper end to the height is 1: 8). The ethylene sulfide continuous production equipment comprises: the continuous reactor comprises a continuous reactor 1, a feeding tank 2 and a heat preservation storage tank 3 which are connected with the upper end of the continuous reactor 1, a solid waste collector 4 which is connected with the lower end of the continuous reactor 1, a condenser which is connected with an air outlet hole at the upper end of the continuous reactor 1, and a gas-liquid separator which is connected with the condenser.
Preheating a continuous reactor 1 to 130 ℃, starting a spiral scraper 5 for stirring, simultaneously starting an oscillator 6, feeding sodium thiocyanate into the continuous reactor 1 from a feeding tank 2, atomizing ethylene carbonate into the continuous reactor 1 through a liquid atomizer 7, and adjusting a meter to ensure that the sodium thiocyanate and the ethylene carbonate enter the continuous reactor 1 according to a molar ratio of 1: 1. The generated ethylene sulfide is condensed and collected in a liquid collector through a gas-liquid separator for further preparing the diethylaminoethanethiol.
After the reaction entered steady state, continuous 8 hour production data were collected: the dosage of ethylene carbonate is 2100kg, the dosage of sodium thiocyanate is 1875kg, the total yield of the ethylene sulfide is 1360kg, and the yield of solid waste is 500 kg.
The purity of the produced ethylene sulfide gas phase detection is 99.6%, and the yield is 97.8%.
This production line uses artifical 1 people.
The solid waste is powdery, 500kg of the solid waste is extracted by methanol and then is recovered by two-step crystallization, the crude product amount of the first crystallization is 441kg, the refined product amount is 406kg, the refined product purity is 96.1 percent, and the yield is 81.2 percent.
Example 2
This example used the process of the present invention to produce ethylene sulfide. Referring to example 1 and FIG. 1, there is shown an apparatus for continuously producing ethylene sulfide in which a continuous reactor has a reverse conical frustum shape having a ratio of an upper vertex radius to a height of 1: 8.5.
Preheating a continuous reactor 1 to 110 ℃, starting a spiral scraper 5 for stirring, simultaneously starting an oscillator 6, feeding sodium thiocyanate into the continuous reactor 1 from a feeding tank 2, atomizing ethylene carbonate into the continuous reactor 1 through a liquid atomizer 7, and adjusting a meter to ensure that the sodium thiocyanate and the ethylene carbonate enter the continuous reactor 1 according to a molar ratio of 1: 1. The generated ethylene sulfide is condensed and collected in a liquid collector through a gas-liquid separator for further preparing the diethylaminoethanethiol.
After the reaction entered steady state, continuous 8 hour production data were collected: the dosage of ethylene carbonate is 2100kg, the dosage of sodium thiocyanate is 1875kg, the yield of ethylene sulfide is 1357.5kg, and the yield of solid waste is 500 kg. The purity of the produced ethylene sulfide gas phase detection is 99.6%, and the yield is 97.6%. This production line uses artifical 1 people.
Comparative example 1
This comparative example used the existing batch tank reaction to prepare ethylene sulfide.
Adding 220kg of ethylene carbonate (0.52 time of the total feeding amount of the ethylene carbonate) into a reaction tank, heating to 55 ℃ for melting, stirring, adding 375kg of sodium thiocyanate, directly heating to 85 ℃ by starting steam, separating and collecting fractions by a coil heat exchanger and a cyclone gas-liquid separator after fractions are discharged, simultaneously dropwise adding 200kg of the remaining ethylene carbonate with the temperature of 75 ℃, and controlling the temperature in the dropwise adding process to be 100 ℃. After the ethylene sulfide is dripped, the temperature is continuously raised to 138 ℃, and the reaction is ended until no fraction is distilled out. The reaction and operation took 2 hours to give 270.8kg of ethylene sulfide, the purity by gas phase detection was 99.6%, and the yield was 97.5%.
The reaction takes 4 hours in total, 5 workers are used, the solid waste is oil-contaminated hard blocks, the production amount is 100kg, the solid waste is not recycled, the solid waste is directly and repeatedly soaked and cleaned by water with the temperature of more than 90 ℃, the cleaning process has heavy odor pollution, and the reaction takes 3 hours for treating the solid waste.
Comparing examples 1 and 2 with comparative example 1, it can be seen that the continuous reactor of the present invention achieves the effects of cleanness, no pollution, stable production index, less human consumption, and contribution to industrial scale-up production, compared with the batch tank reaction in the prior art.
Claims (13)
1. A method for the continuous production of ethylene sulfide, the method comprising: and continuously adding the ethylene carbonate and thiocyanate into a high-temperature reactor, reacting under the stirring action to generate ethylene sulfide and cyanate, continuously discharging the generated ethylene sulfide from a gas outlet of the reactor, condensing and separating to obtain liquid ethylene sulfide, and continuously discharging the generated cyanate from the bottom of the reactor.
2. The process of claim 1, wherein the reactor temperature is controlled at 90-140 ℃.
3. A process as claimed in claim 1 or 2, wherein the cyanate formed is scraped off and discharged by means of scrapers arranged in the reactor.
4. A process according to any one of claims 1 to 3, wherein the ethylene carbonate is atomised before being fed into the continuous reactor.
5. A process according to any one of claims 1 to 4, wherein the thiocyanate salt enters the continuous reactor in powder form and has a particle size of 10 to 200 mesh.
6. A process according to any one of claims 1 to 5, wherein the molar ratio of ethylene carbonate to thiocyanate is about 1:1, for example 1:0.9 to 1.1, preferably 1:0.95 to 1.05, more preferably 1: 0.98-1.02.
7. A process according to any one of claims 1 to 6, wherein the process further comprises refining the cyanate withdrawn from the bottom of the continuous reactor (1) with methanol to obtain pure cyanate.
8. The method according to any one of claims 1 to 7, wherein the method comprises:
preheating the continuous reactor (1) to 90-140 ℃, adding thiocyanate powder in the feeding tank (2) into the continuous reactor (1), and simultaneously adding ethylene carbonate in the heat-preservation storage tank (3) into the continuous reactor (1) after being atomized by the liquid atomizer (7);
gas generated in the continuous reactor (1) sequentially enters a condenser and a gas-liquid separator through pipelines and is collected in a liquid collector to obtain ethylene sulfide, and meanwhile cyanate generated in the continuous reactor (1) is scraped from the inner wall of the continuous reactor (1) by a scraper (5) and enters a solid waste collector (4).
9. The process according to any one of claims 1 to 8, wherein it employs a plant for the continuous production of ethylene sulfide comprising:
a continuous reactor (1) for the continuous reaction,
a feeding tank (2) and a heat-preservation storage tank (3) which are connected with the upper end of the continuous reactor (1),
a solid waste collector (4) connected with the lower end of the continuous reactor (1),
a condenser and a gas-liquid separator which are connected with an air outlet at the upper end of the continuous reactor (1),
wherein, a scraper (5) contacting with the inner wall of the continuous reactor (1) is arranged in the continuous reactor.
10. The apparatus according to claim 9, the lower outer surface of the continuous reactor (1) being provided with an oscillator (6).
11. The apparatus according to claim 9, wherein a liquid atomizer (7) is arranged between the holding tank (3) and the continuous reactor (1).
12. The process according to any one of claims 9 to 11, wherein the continuous reactor (1) has an inverted frustum or cylindrical shape; preferably, the scraper 5 is a screw type scraper.
13. The method according to any one of claims 9 to 12, wherein meters are provided on the connecting lines of the feed tank (2) and holding tank (3) to the continuous reactor (1), respectively.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110665449A (en) * | 2019-09-26 | 2020-01-10 | 保定加合精细化工有限公司 | Equipment for continuously producing ethylene sulfide |
| CN113943236A (en) * | 2020-07-17 | 2022-01-18 | 新疆上昵生物科技有限公司 | Method for continuously preparing diethylaminoethanethiol |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110665449A (en) * | 2019-09-26 | 2020-01-10 | 保定加合精细化工有限公司 | Equipment for continuously producing ethylene sulfide |
| CN113943236A (en) * | 2020-07-17 | 2022-01-18 | 新疆上昵生物科技有限公司 | Method for continuously preparing diethylaminoethanethiol |
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Application publication date: 20200121 |