CN111217675A - Method for resource utilization of epichlorohydrin by-product - Google Patents
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- CN111217675A CN111217675A CN202010111393.9A CN202010111393A CN111217675A CN 111217675 A CN111217675 A CN 111217675A CN 202010111393 A CN202010111393 A CN 202010111393A CN 111217675 A CN111217675 A CN 111217675A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention provides a method for recycling by-products in wastewater generated in preparation of epichlorohydrin by a hydrogen peroxide direct oxidation method. Compared with the reported technology, the invention improves the utilization rate of raw materials and reduces the cost; the whole process is simple and easy to industrialize.
Description
Technical Field
The invention belongs to the technical field of petrochemical industry, and particularly relates to a method for recycling epichlorohydrin by-products.
Background
Epichlorohydrin is an unstable, volatile, colorless, oily liquid, which is slightly soluble in water. As an important chemical raw material, the high-performance nitroglycerin explosive is mainly used for manufacturing epoxy resin and is also a main raw material of nitroglycerin explosive, glass fiber reinforced plastic and electrical insulation products. In the past, the industrial production is mainly carried out by a propylene chlorination method, propylene and chlorine are subjected to high-temperature chlorination to obtain chloropropene, the chloropropene is reacted with hypochlorous acid to prepare dichloropropanol, and the dichloropropanol is saponified to obtain epichlorohydrin.
In order to solve the problem, researchers provide a direct oxidation method which takes a titanium-silicon molecular sieve as a catalyst and chloropropene and hydrogen peroxide as raw materials, and the method has the advantages of high atom utilization rate, less waste water, accordance with the green chemical development direction and better industrial prospect. However, during the synthesis of the epoxy chloropropane by adopting the method, a certain amount of by-products of chlorohydrin ether and monochloropropanediol, namely 3-chloro-1-methoxy-2-propanol, 3-chloro-2-methoxy-1-propanol and 3-chloro-1, 2-propanediol, are generated. The part of the by-products are mainly in a water layer, if the by-products are used for biochemical treatment of wastewater, the COD content is higher, the biodegradability is poor, and resource waste is caused to reduce the economy of the route.
Patent CN110256203A relates to a method for recycling condensed alcohol ether in propylene oxide wastewater, which hydrolyzes the condensed alcohol ether into propylene glycol and methanol by passing the condensed alcohol ether through a modified molecular sieve catalyst. However, the method cannot fully hydrolyze the condensed alcohol ether, and the mixture of propylene glycol and the condensed alcohol ether is obtained after the reaction is finished, so the separation difficulty is high, and the economical efficiency is poor.
In patent CN106630083A and patent CN106630007A, an alkaline aqueous solution or a solid strong base catalyst is adopted to convert 3-chloro-1, 2-propylene glycol in the epoxidation wastewater into glycerol and convert monochloropropanediol monomethyl ether into glycerol monomethyl ether, so that the wastewater is nontoxic and harmless. The method realizes the harmless treatment of the wastewater, but does not relate to the resource utilization of the monochloropropanediol and the condensed alcohol ether.
Patent CN109456289A is a method for resource utilization of epoxy resin key intermediate epichlorohydrin production wastewater, wherein Zn, Fe, Cu or Ag modified granular activated carbon is used as an adsorbent, and due to the limitation of adsorption capacity, frequent desorption regeneration is required, and in addition, low-boiling-point solvents such as dichloromethane and acetone are added in desorption, so that the solvent loss is large, and the cost is high.
Aiming at the problems existing in the process of processing the epoxy chloropropane by-products in the prior technical scheme, the invention provides a novel resource utilization method, can effectively recover the chlorohydrin ethers and monochloropropanediol by-products of the epoxy chloropropane, realizes resource utilization and has wide application prospect.
Disclosure of Invention
The mass concentration of the epichlorohydrin water layer concentrated solution provided by the invention comprises the following components: 10-60% of 3-chloro-1-methoxy-2-propanol, 0-10% of 3-chloro-2-methoxy-1-propanol, 5-30% of 3-chloro-1, 2-propylene glycol and 0-30% of water.
In order to achieve the purpose of the invention, the following technical scheme is adopted:
firstly, adding an epoxy chloropropane water layer concentrated solution and a catalyst into a reaction kettle according to a certain feeding ratio, introducing nitrogen to fully replace air in a device after feeding is finished, introducing hydrogen chloride after replacement is finished, controlling a certain temperature, pressure and time to carry out reaction, and finishing the reaction when monochloropropanediol and chlorohydrin ether in a system are reduced to a certain concentration;
secondly, closing a steam valve after the reaction is finished, opening circulating water for cooling, then slowly opening a pressure release valve, allowing the gas containing chloromethane and hydrogen chloride to pass through a water absorption tower, then entering a drying tower for drying the chloromethane gas, removing water, and immediately sending the gas into a compressor to be compressed into liquid chloromethane;
and thirdly, dripping the chlorination liquid in the reaction kettle into an analysis kettle filled with calcium chloride, heating for dehydrochlorination for analysis, layering after analysis is finished, obtaining an analysis oil layer, pumping into a rectifying tower, and performing vacuum rectification to obtain a dichloropropanol product for preparing epoxy chloropropane.
In the first step, the catalyst is selected to be an acid catalyst, preferably one or more of adipic acid, succinic acid, oxalic acid and acetic acid;
the dosage of the catalyst is 0-50% of the molar mass of the chlorohydrin ether and the chloropropanediol, and is preferably 3-10%.
The reaction temperature range is 90-160 ℃, and preferably 100-130 ℃;
the reaction pressure range is 0-5.0 MPa, preferably 0-3.0 MPa;
the reaction time is 0-30 h, preferably 5-30 h;
in the first step, the mass concentration of the chlorohydrin ether is less than or equal to 0.5 percent and the mass concentration of the monochloropropanediol is less than or equal to 5 percent after the reaction is finished;
in the second step, the mass concentration of the liquid chloromethane is more than or equal to 99.0 percent;
in the third step, the dichloropropanol obtained by rectification is a mixture of 1, 3-dichloropropanol and 2, 3-dichloropropanol, and the mass concentration is more than or equal to 98.0%.
Compared with the prior art, the invention has the following advantages: the prior art can not fully recycle the by-products in the water layer, thereby causing resource waste and high treatment cost. The chlorohydrin ether byproduct of the epoxy chloropropane in the process reacts with hydrogen chloride under the action of the catalyst to generate chloromethane and monochloropropanediol, and further reacts with the hydrogen chloride to obtain dichloropropanol, so that the resource utilization of the byproduct is realized, the utilization rate of raw materials is improved, and the cost is reduced; the whole process is simple and easy to industrialize.
Drawings
FIG. 1 reaction mechanism of the present invention.
FIG. 2 is a flow diagram of the resource utilization of the epichlorohydrin byproduct.
Detailed Description
The mass concentration of the epoxy chloropropane water layer concentrated solution is as follows: 54.02 percent of 3-chloro-1-methoxy-2-propanol, 4.83 percent of 3-chloro-2-methoxy-1-propanol, 21.35 percent of 3-chloro-1, 2-propanediol and 19.50 percent of water.
Example 1 atmospheric reaction
Putting the epoxy chloropropane water layer concentrated solution into a reaction kettle, adopting adipic acid as a catalyst, wherein the input amount is 3 percent of the total molar number of monochloropropanediol and chlorohydrin ether in the concentrated solution, introducing air into a nitrogen displacement device after the feeding is finished, introducing hydrogen chloride for normal pressure reaction after the displacement is finished, heating to 100-110 ℃, introducing chlorinated tail gas into a water spraying absorption tower, removing hydrogen chloride in the tail gas, then drying the chlorinated tail gas in a drying tower, immediately conveying the dried chlorinated tail gas to a compressor to compress the chlorinated tail gas into liquid methyl chloride, and then pumping the liquid methyl chloride into a methyl chloride storage tank for storage, wherein the mass concentration of the liquid methyl chloride is 99.1 percent.
The chlorination liquid for chlorination reaction for 30 hours under normal pressure consists of the following components in percentage by mass: 0.07% of 3-chloro-1-methoxy-2-propanol, 0.01% of 3-chloro-2-methoxy-1-propanol, 1.98% of 3-chloro-1, 2-propanediol, 56.03% of 1, 3-dichloropropanol and 1.86% of 2, 3-dichloropropanol. The conversion rate of total chlorohydrin ether (the sum of 3-chloro-1-methoxy-2-propanol and 3-chloro-2-methoxy-1-propanol) is 99.84%, the conversion rate of monochloropropanediol (3-chloro-1, 2-propanediol) is 88.27%, and the yield of total dichloropropanol (the sum of 1, 3-dichloropropanol and 2, 3-dichloropropanol) is 85.91%.
Dropwise adding the chloride into an analysis kettle filled with calcium chloride, heating to 110-120 ℃ after dropwise adding, carrying out analysis, removing hydrogen chloride in the chloride solution to a water absorption tower, cooling after analysis, layering oil, extracting calcium chloride from a water layer, returning to the next batch of analysis, pumping an oil layer into a rectifying tower, and rectifying under the vacuum degree of 10-30 mmHg to obtain a product, namely 1, 3-dichloropropanol with the mass concentration of 97.33%, 2, 3-dichloropropanol with the mass concentration of 1.75%, and dichloropropanol with the total mass concentration of 99.08%, which is used for preparing epoxy chloropropane.
Example 2
Putting the epoxy chloropropane water layer concentrated solution into a reaction kettle, adopting adipic acid as a catalyst, wherein the input amount is 3 percent of the total mole number of the byproduct chloropropanediol and chlorohydrin ether in the concentrated solution, introducing nitrogen gas to fully displace air in the device after the feeding is finished, closing a nitrogen gas valve after the displacement is finished, reducing the temperature, introducing hydrogen chloride to the pressure of 0.3MPa, introducing hydrogen chloride to the reaction kettle, sealing the high-pressure kettle, heating to 100 ℃, and reacting for 12 hours, wherein the pressure is 0.7-1.5 MPa.
And after the reaction is finished, closing a steam valve, opening circulating water for cooling, opening a pressure release valve, removing hydrogen chloride from chlorinated tail gas containing methyl chloride and hydrogen chloride through a water absorption tower, then drying the methyl chloride gas in a drying tower, immediately feeding the dried methyl chloride gas into a compressor to be compressed into liquid methyl chloride after moisture is removed, and pumping the liquid methyl chloride gas into a methyl chloride storage tank for low-temperature storage, wherein the mass concentration of the liquid methyl chloride is 99.3%. The mass concentration of the chlorination liquid in the reaction kettle is as follows: 0.04% of 3-chloro-1-methoxy-2-propanol, no detection of 3-chloro-2-methoxy-1-propanol, 1.23% of 3-chloro-1, 2-propanediol, 59.35% of 1, 3-dichloropropanol and 1.48% of 2, 3-dichloropropanol. The conversion rate of the total chlorohydrin ether is 99.91 percent, the conversion rate of the monochloropropanediol is 92.45 percent, and the yield of the total dichloropropanol is 93.71 percent.
Dripping the chlorination liquid in the reaction kettle into an analysis kettle filled with calcium chloride, heating to 110-120 ℃, carrying out analysis dehydrochlorination to a water absorption tower, cooling to 60-80 ℃ after analysis is finished, layering, pumping an analysis oil layer into a rectifying tower, and rectifying under the vacuum degree of 10-30 mmHg to obtain products 1, 3-dichloropropanol 97.91%, 2, 3-dichloropropanol 1.58% and dichloropropanol total content of 99.49%, wherein the products are used for preparing epoxy chloropropane.
Examples 3, 4 and 5
Different catalysts are screened on the basis of example 2, succinic acid, oxalic acid and acetic acid are respectively used as the catalysts, other conditions are unchanged, and the data are shown in table 1.
TABLE 1
Examples 6 and 7
The amount of adipic acid added was adjusted on the basis of example 2, the adipic acid accounted for 5% and 10% of the total moles of monochloropropanediol and chlorohydrin ether as reactants in the concentrated solution, and the data are shown in table 2, otherwise.
TABLE 2
Example 8
On the basis of the example 6, the reaction temperature is adjusted to 110 ℃, the pressure is 0.8-1.8 MPa, the reaction time is 10h, and other conditions are unchanged, and the data are shown in Table 3.
TABLE 3
Example 9
On the basis of the example 6, the reaction temperature is adjusted to 130 ℃, the pressure is 1.2-2.7 MPa, the reaction time is 6h, other conditions are unchanged, and the data are shown in Table 4.
TABLE 4
The embodiments of the present invention are explained in detail, and the above description of the embodiments is only for the purpose of helping understanding the core idea of the present invention. It should be noted that various changes and modifications to the invention could be made by those skilled in the art without departing from the principle of the invention, and the invention also falls within the protection scope of the claims of the invention.
Claims (10)
1. A method for recycling wastewater generated in preparation of epichlorohydrin by a hydrogen peroxide direct oxidation method is characterized by comprising the following steps,
firstly, adding an epoxy chloropropane water layer concentrated solution and a catalyst into a reaction kettle according to a certain feeding ratio, introducing nitrogen to fully replace air in a device after feeding is finished, introducing hydrogen chloride after replacement is finished, controlling a certain temperature, pressure and time to carry out reaction, and finishing the reaction when chlorohydrin ether and monochloropropanediol in a system are reduced to a certain concentration;
secondly, closing a steam valve after the reaction is finished, opening circulating water for cooling, then slowly opening a pressure release valve, allowing the gas containing chloromethane and hydrogen chloride to pass through a water absorption tower, then entering a drying tower for drying the chloromethane gas, removing water, and immediately sending the gas into a compressor to be compressed into liquid chloromethane;
and thirdly, dripping the chlorination liquid in the reaction kettle into an analysis kettle filled with calcium chloride, heating for dehydrochlorination for analysis, layering after analysis is finished, obtaining an analysis oil layer, pumping into a rectifying tower, and performing vacuum rectification to obtain a dichloropropanol product for preparing epoxy chloropropane.
2. The method for recycling wastewater generated in preparation of epichlorohydrin by using a direct hydrogen peroxide oxidation method according to claim 1, wherein in the first step, the catalyst is an acidic catalyst, preferably one or more of adipic acid, succinic acid, oxalic acid and acetic acid.
3. The method for recycling wastewater generated in preparation of epichlorohydrin by using a direct hydrogen peroxide oxidation method according to claim 1, wherein in the first step, the amount of the catalyst is 0-50%, preferably 3-10% of the total molar mass of chlorohydrin ether and monochloropropanediol.
4. The method for recycling wastewater generated in preparation of epichlorohydrin by using a direct hydrogen peroxide oxidation method according to claim 1, wherein in the first step, the reaction temperature is in a range of 90-160 ℃, preferably 100-130 ℃.
5. The method for recycling wastewater generated in preparation of epichlorohydrin by using a direct hydrogen peroxide oxidation method according to claim 1, wherein in the first step, the reaction pressure is in a range of 0-5.0 MPa, preferably 0-3.0 MPa.
6. The method for recycling wastewater generated in preparation of epichlorohydrin by using a direct hydrogen peroxide oxidation method according to claim 1, wherein in the first step, the reaction time is 0-30 hours, preferably 5-30 hours.
7. The method for recycling the wastewater generated in the preparation of the epichlorohydrin by the direct hydrogen peroxide oxidation method according to claim 1, wherein in the first step, the mass concentration of the chlorohydrin ether is less than or equal to 0.5% and the mass concentration of the monochloropropanediol is less than or equal to 5% after the reaction is finished.
8. The method for recycling wastewater generated in the preparation of epichlorohydrin by using the direct hydrogen peroxide oxidation method according to claim 1, wherein the mass concentration of liquid methyl chloride in the second step is not less than 99.0%.
9. The method for recycling wastewater generated in preparation of epichlorohydrin by using a direct hydrogen peroxide oxidation method according to claim 1, wherein in the third step, the dichloropropanol obtained by rectification is a mixture of 1, 3-dichloropropanol and 2, 3-dichloropropanol, and the mass concentration is more than or equal to 98.0%.
10. The method for recycling wastewater from the preparation of epichlorohydrin by a hydrogen peroxide direct oxidation method according to claim 1, wherein the mass concentration of the epichlorohydrin wastewater comprises: 10-60% of 3-chloro-1-methoxy-2-propanol, 0-10% of 3-chloro-2-methoxy-1-propanol, 5-30% of 3-chloro-1, 2-propylene glycol and 0-30% of water.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111875478A (en) * | 2020-07-07 | 2020-11-03 | 江苏扬农化工集团有限公司 | Method for refining methanol recovered by epoxy chloropropane process by hydrogen peroxide method |
| CN112279823A (en) * | 2020-10-22 | 2021-01-29 | 江苏扬农化工集团有限公司 | Method for preparing methyl glycidyl ether from epichlorohydrin by-product |
| CN113480496A (en) * | 2021-06-09 | 2021-10-08 | 江苏瑞恒新材料科技有限公司 | Comprehensive utilization method of epoxy chloropropane by-product by hydrogen peroxide method |
| CN115745753A (en) * | 2022-12-29 | 2023-03-07 | 河南红东方化工股份有限公司 | Method for directly producing alcohol ether products by byproduct chloromethane |
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