CN111217675B - Method for resource utilization of epichlorohydrin by-product - Google Patents

Method for resource utilization of epichlorohydrin by-product Download PDF

Info

Publication number
CN111217675B
CN111217675B CN202010111393.9A CN202010111393A CN111217675B CN 111217675 B CN111217675 B CN 111217675B CN 202010111393 A CN202010111393 A CN 202010111393A CN 111217675 B CN111217675 B CN 111217675B
Authority
CN
China
Prior art keywords
epichlorohydrin
preparation
hydrogen peroxide
recycling
wastewater generated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202010111393.9A
Other languages
Chinese (zh)
Other versions
CN111217675A (en
Inventor
徐林
丁克鸿
王怡明
宋洋
杨树斌
王丹
徐高明
王再飞
姜欣宇
王建昌
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NINGXIA RUITAI TECHNOLOGY CO LTD
Jiangsu Ruixiang Chemical Co Ltd
Jiangsu Yangnong Chemical Group Co Ltd
Jiangsu Ruisheng New Material Technology Co Ltd
Original Assignee
NINGXIA RUITAI TECHNOLOGY CO LTD
Jiangsu Ruixiang Chemical Co Ltd
Jiangsu Yangnong Chemical Group Co Ltd
Jiangsu Ruisheng New Material Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by NINGXIA RUITAI TECHNOLOGY CO LTD, Jiangsu Ruixiang Chemical Co Ltd, Jiangsu Yangnong Chemical Group Co Ltd, Jiangsu Ruisheng New Material Technology Co Ltd filed Critical NINGXIA RUITAI TECHNOLOGY CO LTD
Priority to CN202010111393.9A priority Critical patent/CN111217675B/en
Publication of CN111217675A publication Critical patent/CN111217675A/en
Application granted granted Critical
Publication of CN111217675B publication Critical patent/CN111217675B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • C07C29/62—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
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)

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

Method for resource utilization of epichlorohydrin by-product
Technical Field
The invention belongs to the technical field of petrochemical industry, and particularly relates to a method for recycling epichlorohydrin byproducts.
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, a certain amount 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 in the process of synthesizing the epoxy chloropropane by adopting the method. 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 condensation alcohol ether in epoxy propane wastewater, wherein the condensation alcohol ether is hydrolyzed into propylene glycol and methanol by 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-propanediol in 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 discloses a method for resource utilization of epoxy resin key intermediate epichlorohydrin production wastewater, which adopts Zn, fe, cu or Ag modified granular activated carbon as an adsorbent, needs frequent desorption regeneration due to limited adsorption capacity, and in addition, low-boiling 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, which can effectively recover the chlorohydrin ethers and monochloropropanediol by-products of the epoxy chloropropane, realize resource utilization and have 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-propanediol 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 from acid catalyst, preferably one or more of adipic acid, succinic acid, oxalic acid and acetic acid;
the dosage of the catalyst is 0 to 50 percent, preferably 3 to 10 percent of the molar mass of the chlorohydrin ether and the monochloropropanediol.
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 to 30 hours, preferably 5 to 30 hours;
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 mole 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 after the moisture is removed, then pumping the liquid methyl chloride into a methyl chloride storage tank for storage, and the mass concentration of the liquid methyl chloride is 99.1 percent.
The chlorination reaction is carried out for 30 hours under normal pressure, and the mass concentration of the chlorination liquid is as follows: 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 of total chlorohydrin ethers (sum of 3-chloro-1-methoxy-2-propanol and 3-chloro-2-methoxy-1-propanol) was 99.84%, the conversion of monochloropropanediol (referred to as 3-chloro-1, 2-propanediol) was 88.27%, and the total dichloropropanol (sum of 1, 3-dichloropropanol and 2, 3-dichloropropanol) yield was 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 and layering oil after analysis, extracting calcium chloride from a water layer, returning to the next batch of analysis, pumping an oil layer into a rectifying tower, rectifying under the vacuum degree of 10-30 mmHg to obtain the product 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 replace air in the device after the feeding is finished, closing a nitrogen gas valve after the replacement 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 the temperature of 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, layering, pumping the obtained analysis oil layer into a rectifying tower, rectifying under the vacuum degree of 10-30 mmHg to obtain the products 1, 3-dichloropropanol 97.91%,2, 3-dichloropropanol 1.58% and dichloropropanol with the total content of 99.49% 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
Figure BDA0002390144840000051
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
Figure BDA0002390144840000061
Example 8
The reaction temperature is adjusted to 110 ℃, the pressure is 0.8-1.8 MPa, the reaction time is 10h, and other conditions are not changed on the basis of the example 6, and the data are shown in a table 3.
TABLE 3
Figure BDA0002390144840000062
Example 9
The reaction temperature is adjusted to 130 ℃, the pressure is 1.2-2.7 MPa, the reaction time is 6h, and other conditions are not changed on the basis of the example 6, and the data are shown in a table 4.
TABLE 4
Figure BDA0002390144840000063
Figure BDA0002390144840000071
The embodiments of the present invention are explained, and the above description of the embodiments is only for assisting understanding of the core idea of the present invention. It should be noted that various modifications and alterations to the present invention may be made by those skilled in the art without departing from the principles of the invention, and it is intended to cover the scope of the appended claims.

Claims (11)

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,
step one, 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 the feeding is finished, introducing hydrogen chloride after the 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; the catalyst is an acid catalyst;
step two, 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 drying the chloromethane gas in a drying tower, removing moisture, and immediately feeding into a compressor to compress the gas into liquid chloromethane;
thirdly, dripping the chlorinated solution in the reaction kettle into an analysis kettle filled with calcium chloride, heating for dehydrochlorination for analysis, layering after analysis, obtaining an analysis oil layer, pumping into a rectifying tower, and carrying out vacuum rectification to obtain a dichloropropanol product for preparing the epoxy chloropropane, wherein the mass concentration of the epoxy chloropropane water layer concentrated solution is as follows: 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-propanediol and 0-30% of water.
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 one or more of adipic acid, succinic acid, oxalic acid and acetic acid.
3. 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 amount of the catalyst is 3-10% of the total molar mass of the chlorohydrin ether and the 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 ranges from 90 ℃ to 160 ℃.
5. The method for recycling wastewater generated in preparation of epichlorohydrin by using a direct hydrogen peroxide oxidation method according to claim 4, wherein in the first step, the reaction temperature ranges from 100 ℃ to 130 ℃.
6. 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 reaction pressure is in a range of 0 to 5.0MPa.
7. The method for recycling wastewater generated in the preparation of epichlorohydrin by using the direct hydrogen peroxide oxidation method according to claim 6, wherein in the first step, the reaction pressure is in the range of 0 to 3.0MPa.
8. 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 the reaction time is 5-30 h in the first step.
9. The method for recycling the wastewater generated in the preparation of the epichlorohydrin by the direct hydrogen peroxide oxidation process 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%.
10. 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%.
11. 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 third step, the dichloropropanol obtained by rectification is a mixture of 1, 3-dichloropropanol and 2, 3-dichloropropanol, and the mass concentration of the dichloropropanol is not less than 98.0%.
CN202010111393.9A 2020-02-24 2020-02-24 Method for resource utilization of epichlorohydrin by-product Active CN111217675B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010111393.9A CN111217675B (en) 2020-02-24 2020-02-24 Method for resource utilization of epichlorohydrin by-product

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010111393.9A CN111217675B (en) 2020-02-24 2020-02-24 Method for resource utilization of epichlorohydrin by-product

Publications (2)

Publication Number Publication Date
CN111217675A CN111217675A (en) 2020-06-02
CN111217675B true CN111217675B (en) 2022-11-01

Family

ID=70811197

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010111393.9A Active CN111217675B (en) 2020-02-24 2020-02-24 Method for resource utilization of epichlorohydrin by-product

Country Status (1)

Country Link
CN (1) CN111217675B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111875478B (en) * 2020-07-07 2022-03-29 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
CN112279823B (en) * 2020-10-22 2023-09-12 江苏扬农化工集团有限公司 Method for preparing methyl glycidyl ether from epoxy chloropropane by-product
CN113480496B (en) * 2021-06-09 2023-04-07 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
CN115745753B (en) * 2022-12-29 2024-04-09 河南红东方化工股份有限公司 Method for directly producing alcohol ether products by using byproduct chloromethane

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2045785A (en) * 1934-12-28 1936-06-30 Standard Oil Dev Co Process for converting ethers to alcohols
PL1752435T3 (en) * 2003-11-20 2012-11-30 Solvay Process for producing epichlorhydrin
EP2174925B1 (en) * 2004-07-21 2014-10-15 Dow Global Technologies LLC Conversion of a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin
CN101215223B (en) * 2007-12-27 2010-11-03 江西省飓风化工有限公司 Method for preparing dichloropropanol from glycerin
EP2268596B1 (en) * 2008-04-03 2017-05-31 Solvay Sa Composition comprising glycerol, process for obtaining same and use thereof in the manufacture of dichloropropanol
JP5146194B2 (en) * 2008-08-19 2013-02-20 東ソー株式会社 Method for producing dichloropropanol
FR2939434B1 (en) * 2008-12-08 2012-05-18 Solvay PROCESS FOR TREATING GLYCEROL
CN109824625A (en) * 2019-02-20 2019-05-31 江苏扬农化工集团有限公司 A kind of method of epoxy resin key intermediate epoxychloropropane production utilization of wastewater resource
CN110256203B (en) * 2019-06-05 2022-06-14 江苏扬农化工集团有限公司 Method for resource utilization of condensation alcohol ether in epoxy propane wastewater
CN110746270B (en) * 2019-11-04 2023-06-06 江苏扬农化工集团有限公司 Method for recycling epichlorohydrin wastewater

Also Published As

Publication number Publication date
CN111217675A (en) 2020-06-02

Similar Documents

Publication Publication Date Title
CN111217675B (en) Method for resource utilization of epichlorohydrin by-product
CN110078684B (en) Method for continuously synthesizing epichlorohydrin by using microchannel reactor
CN111362901B (en) A kind of fluoroalcohol functionalized ionic liquid catalyzes the method for carbon dioxide to synthesize cyclic carbonate
CN110746270B (en) Method for recycling epichlorohydrin wastewater
CN111925272B (en) Method for processing recovered pentamethyl indane
EP2321291B1 (en) Process for producing epoxides
CN101279961B (en) Method for preparing epoxy chloropropane by epoxidation of propylene chloride
US9850190B2 (en) Process for preparing dichloropropanol
CN112239434A (en) Epoxy chloropropane production device and process
CN102892740A (en) Process for producing allyl alcohol
KR101705210B1 (en) Method of preparing composition of chlorohydrins and method of preparing epichlorohydrin using composition of chlorohydrins prepared by the same
CN101357880A (en) A process and system for preparing dichloropropanol by self-catalyzed reaction of glycerin and hydrogen chloride
CN102234223A (en) Method for synthesizing dichloropropanol by reaction of glycerol and hydrogen chloride
CN101979365A (en) A kind of method for continuously preparing dichloropropanol
KR101705208B1 (en) Method of preparing composition of chlorohydrins and method of preparing epichlorohydrin using composition of chlorohydrins prepared by the same
CN110002970B (en) Production method and production system of sandalwood ether
CN102040479B (en) System for preparing dichloropropanol through autocatalytic reaction of glycerol and hydrogen chloride
EP2589585B1 (en) Method for preparing chlorohydrins and method for preparing epichlorohydrin using chlorohydrins prepared thereby
CN213977489U (en) Glycerol chlorination unit for epoxy chloropropane production device
KR101705209B1 (en) Method of preparing composition of chlorohydrins and method of preparing epichlorohydrin using composition of chlorohydrins prepared by the same
CN114874069B (en) Method and device for preparing electronic grade ethylene glycol
CN106632149B (en) A kind of process modification producing epoxychloropropane using glycerol method dichlorohydrin as raw material
CN101781204B (en) Method for continuously preparing phenyl acetate
CN111252833A (en) Wastewater treatment process for producing epoxy chloropropane by oxidizing chloropropene
CN107867975B (en) A kind of method for synthesizing carvacrol with isodihydrocarvone

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant