CN110180591B - Catalyst dealcoholization process for producing epoxy chloropropane by hydrogen peroxide direct oxidation method - Google Patents
Catalyst dealcoholization process for producing epoxy chloropropane by hydrogen peroxide direct oxidation method Download PDFInfo
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- CN110180591B CN110180591B CN201910450410.9A CN201910450410A CN110180591B CN 110180591 B CN110180591 B CN 110180591B CN 201910450410 A CN201910450410 A CN 201910450410A CN 110180591 B CN110180591 B CN 110180591B
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- 238000000034 method Methods 0.000 title claims abstract description 57
- 239000003054 catalyst Substances 0.000 title claims abstract description 44
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 230000003647 oxidation Effects 0.000 title claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 14
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 title claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 121
- 238000005406 washing Methods 0.000 claims abstract description 73
- 239000012071 phase Substances 0.000 claims abstract description 68
- 239000007790 solid phase Substances 0.000 claims abstract description 36
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000003921 oil Substances 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 5
- 230000018044 dehydration Effects 0.000 claims abstract description 4
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims description 4
- 238000004062 sedimentation Methods 0.000 claims description 4
- 239000013505 freshwater Substances 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 150000001298 alcohols Chemical class 0.000 abstract description 5
- HUXDTFZDCPYTCF-UHFFFAOYSA-N 1-chloropropane-1,1-diol Chemical compound CCC(O)(O)Cl HUXDTFZDCPYTCF-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002779 inactivation Effects 0.000 abstract description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000011964 heteropoly acid Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/28—Regeneration or reactivation
- B01J27/285—Regeneration or reactivation of catalysts comprising compounds of phosphorus
-
- 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
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention relates to the field of epoxy chloropropane production, and in particular relates to a catalyst dealcoholization process for producing epoxy chloropropane by a hydrogen peroxide direct oxidation method. Separating materials generated in the reaction procedure in a settling separator to generate oil, water and solid phases, sending the oil phase to a rectification procedure, sending the water and the solid phases into a first-stage water washing tank, adding water into the water and stirring the water and the solid phases; (2) conveying the water and the solid phase which are added with water and stirred from a primary washing tank to a primary washing separator for separation to form a water phase, and feeding the solid phase into a secondary washing tank for adding water and stirring; (3) and (3) conveying the solid phase stirred by adding water from the secondary water washing tank to a secondary water washing separator, conveying the separated water phase to the primary water washing tank to be used as washing water, conveying the solid phase to the primary oil washing tank, adding washing oil, stirring and then performing a catalyst dehydration process. The dealcoholization process can remove reaction byproducts such as 1-chloropropanediol and other alcohols in the catalyst phase, and the byproducts can cause the inactivation of the catalyst, reduce the loss of the catalyst and ensure the reutilization of the catalyst.
Description
Technical Field
The invention relates to the field of epoxy chloropropane production, and in particular relates to a catalyst dealcoholization process for producing epoxy chloropropane by a hydrogen peroxide direct oxidation method.
Background
The existing production method of epoxy chloropropane comprises a DECH (direct oxidation) method, a chlorohydrin method, a glycerol method and an allyl alcohol method, and the DECH method has the advantages of great environmental protection, no waste residue, little waste water, short flow, low energy consumption, easy production and construction of enterprises and the like, so the method gradually develops into the main development direction of the production method of epoxy chloropropane. The DECH method using phosphotungstic heteropoly acid salt as a catalyst has completed an actual dangerous intermittent production stage at present, enters an actual continuous production design and trial operation stage, and needs to be recycled during continuous production due to higher catalyst price, and some byproducts in reaction products can cause catalyst inactivation after entering a catalyst phase, and the catalyst can be recycled after reaction byproducts such as 1-chloropropanediol and other alcohols in the catalyst phase are removed.
Disclosure of Invention
The invention aims to solve the technical problem of how to overcome the defects in the prior art and provide a catalyst dealcoholization process for producing epoxy chloropropane by a hydrogen peroxide direct oxidation method for removing alcohol impurities in a catalyst phase.
The technical solution of the invention is as follows: a catalyst dealcoholization process for producing epoxy chloropropane by a hydrogen peroxide direct oxidation method is characterized by comprising the following steps: (1) separating the materials generated in the reaction process in a sedimentation separator to generate oil, water and solid phases, passing the oil phase through an oil phase buffer tank, passing the oil phase through an oil phase filter, then sending the oil phase to a rectification process, passing the water and solid phases through a water and solid buffer, then sending the water and solid phases into a primary water washing tank, adding water into the primary water washing tank, and stirring; (2) conveying the water and the solid phase which are added with water and stirred from a primary water washing tank to a primary water washing separator through a pump for separation, introducing the separated water phase into a steam stripping procedure after passing through a water phase filter again through a water phase buffer tank, introducing the solid phase into a secondary water washing tank, adding fresh water or steam stripping water of the steam stripping procedure into the secondary water washing tank, and stirring; (3) and the solid phase after being added with water and stirred is conveyed to a secondary water washing separator from a secondary water washing tank through a pump for separation, the separated water phase is conveyed to a primary water washing tank through a water phase buffer tank II through a pump for being used as washing water, and the separated solid phase enters a primary oil washing tank, is added with washing oil and is stirred and then enters a catalyst dehydration procedure.
Further, the mass concentration of the catalyst in the primary washing separator in the step (2) is 1-50%.
Further, the alcohol content of the solid phase separated by the secondary water washing separator in the step (3) is less than or equal to 2000 ppm.
Further, the washing oil in the step (3) is chloropropene.
Further, in the step (1), after the oil phase passes through an oil phase buffer tank, the re-layered oil phase passes through an oil phase filter and then is sent to a rectification process, the water phase enters a first-stage water washing tank, the re-layered oil phase in a water-solid buffer enters the oil phase buffer tank, and the water solid phase enters the first-stage water washing tank.
The invention aims at the problem that the catalyst needs to be recycled in the process of continuously producing epoxy chloropropane by a DECH method with phosphotungstic heteropoly acid salt as the catalyst, and removes alcohols such as 1-chloropropanediol and the like which are byproducts in the solid phase of the catalyst by taking water as a washing agent, thereby reducing the loss amount of the catalyst and ensuring the activity and the cyclic utilization of the catalyst. The water phase generated by the water phase buffer tank II can be used as washing water of the first-level washing tank, and water in the steam stripping process can be recycled, so that water is saved. The invention has potential market value.
Drawings
FIG. 1 is a process flow diagram of the present invention.
Wherein VE-211 is a sedimentation separator, VE-212 is an oil phase buffer tank, MA-201 is an oil phase filter, VE-201 is a water-solid buffer, VE-202 is a primary water washing tank, CF-201 is a primary water washing separator, VE-203 is a water phase buffer tank I, MA-202 is a water phase filter, VE-204 is a secondary water washing tank, CF-202 is a secondary water washing separator, VE-205 is a water phase buffer tank II, and VE-206 is a primary oil washing tank.
Detailed Description
The catalyst dealcoholization process for producing epichlorohydrin by using a hydrogen peroxide direct oxidation method according to the invention is described in detail below with reference to the examples and the accompanying drawings.
A catalyst dealcoholization process for producing epoxy chloropropane by a hydrogen peroxide direct oxidation method is characterized by comprising the following steps:
(1) materials generated in the reaction process enter a sedimentation separator VE-211 to be separated, oil, water and solid phases are generated, wherein the main components of an oil phase comprise raw material chloropropene and product epichlorohydrin, the main components of the water and the solid phases comprise water, by-product alcohol and a solid catalyst, the oil phase passes through an oil phase buffer tank VE-212, then passes through an oil phase filter MA-201, then is sent to a rectification process to be separated, the water and the solid phases pass through a water and solid buffer tank VE-201, then enter a primary water washing tank VE-202, water is added into the primary water washing tank VE-202 to be stirred, and the solid catalyst is washed;
(2) water and solid phases which are added with water and stirred are conveyed from a first-stage water washing tank VE-202 to a first-stage water washing separator CF-201 through a pump for separation, separated water phases pass through a water phase buffer tank VE-203 and then pass through a water phase filter MA-202 and then enter a steam stripping process, solid phases enter a second-stage water washing tank VE-204, and fresh water or steam stripping water of the steam stripping process is added into the second-stage water washing tank VE-204 for stirring; (3) the solid phase after being added with water and stirred is conveyed to a secondary water washing separator CF-202 from a secondary water washing tank VE-204 through a pump for separation, the separated water phase is conveyed to a primary water washing tank VE-202 through a water phase buffer tank VE-205 through a pump to be used as washing water, and the separated solid phase enters a primary oil washing tank VE-206 and is added with washing oil chloropropene and stirred and then enters a catalyst dehydration procedure.
Further, in order to achieve the purposes of completely washing the catalyst and removing alcohols, the mass concentration of the catalyst in the first-stage water washing separator CF-201 in the step (2) is 1-50%.
Furthermore, in order to ensure that the alcohols in the catalyst phase are removed completely without affecting the activity of the catalyst, the alcohol content in the solid phase (catalyst phase) separated by the secondary water washing separator CF-202 in the step (3) is less than or equal to 2000 ppm.
Further, in order to further better separate materials generated in the reaction process, in the step (1), after the oil phase passes through an oil phase buffer tank VE-212, the re-layered oil phase passes through an oil phase filter MA-201 and then is sent to a rectification process, the water phase enters a first-stage water washing tank VE-202, the re-layered oil phase in a water-solid buffer VE-201 enters the oil phase buffer tank VE-212, and the water solid phase enters the first-stage water washing tank VE-202.
The catalyst dealcoholization process can increase or decrease the stages of the water washing tank and the water washing separator according to the needs, but can ensure that the alcohol content in the solid phase (catalyst phase) separated by the last stage water washing separator is less than or equal to 2000ppm so as to ensure that the alcohol content in the catalyst phase does not influence the activity of the catalyst. The temperature in each stage of washing tank is 5-20 ℃, and the pressure is less than or equal to 50 KPa.
The above embodiments are only for illustrating the technical concept and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention accordingly, and not to limit the protection scope of the present invention accordingly. All equivalent changes or modifications made in accordance with the spirit of the present disclosure are intended to be covered by the scope of the present disclosure.
Claims (5)
1. A catalyst dealcoholization process for producing epoxy chloropropane by a hydrogen peroxide direct oxidation method is characterized by comprising the following steps:
(1) separating the materials generated in the reaction process in a sedimentation separator to generate oil, water and solid phases, passing the oil phase through an oil phase buffer tank, passing the oil phase through an oil phase filter, then sending the oil phase to a rectification process, passing the water and solid phases through a water and solid buffer, then sending the water and solid phases into a primary water washing tank, adding water into the primary water washing tank, and stirring;
(2) conveying the water and the solid phase which are added with water and stirred from a primary water washing tank to a primary water washing separator through a pump for separation, introducing the separated water phase into a steam stripping procedure after passing through a water phase filter again through a water phase buffer tank, introducing the solid phase into a secondary water washing tank, adding fresh water or steam stripping water of the steam stripping procedure into the secondary water washing tank, and stirring;
(3) and the solid phase after being added with water and stirred is conveyed to a secondary water washing separator from a secondary water washing tank through a pump for separation, the separated water phase is conveyed to a primary water washing tank through a water phase buffer tank II through a pump for being used as washing water, and the separated solid phase enters a primary oil washing tank, is added with washing oil and is stirred and then enters a catalyst dehydration procedure.
2. The catalyst dealcoholization process for producing epichlorohydrin by using a hydrogen peroxide direct oxidation method according to claim 1, which is characterized in that: and (3) the mass concentration of the catalyst in the primary washing separator in the step (2) is 1-50%.
3. The catalyst dealcoholization process for producing epichlorohydrin by using a hydrogen peroxide direct oxidation method according to claim 1 or 2, which is characterized in that: the alcohol content of the solid phase separated by the secondary water washing separator in the step (3) is less than or equal to 2000 ppm.
4. The catalyst dealcoholization process for producing epichlorohydrin by using a hydrogen peroxide direct oxidation method according to claim 3, which is characterized in that: and (3) the washing oil is chloropropene.
5. The catalyst dealcoholization process for producing epichlorohydrin by using a hydrogen peroxide direct oxidation method according to claim 4, which is characterized in that: and (2) after the oil phase in the step (1) passes through an oil phase buffer tank, sending the re-layered oil phase to a rectification process after passing through an oil phase filter, enabling the water phase to enter a first-stage water washing tank, enabling the re-layered oil phase in a water-solid buffer to enter the oil phase buffer tank, and enabling the water solid phase to enter the first-stage water washing tank.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101481364A (en) * | 2009-02-24 | 2009-07-15 | 江苏扬农化工集团有限公司 | Continuous production method of epoxy chloropropane by hydrogen peroxide process |
CN103880783A (en) * | 2012-12-20 | 2014-06-25 | 中国科学院大连化学物理研究所 | Method for preparing epoxypropane by catalyzing propylene epoxidation with phase-transfer catalyst under reaction control |
CN206232636U (en) * | 2016-12-01 | 2017-06-09 | 中国科学院大连化学物理研究所 | A kind of catalyst recycling retracting device of epoxychloropropane processed |
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EP1816129A4 (en) * | 2004-06-23 | 2008-01-02 | Sumitomo Chemical Co | Method of purifying propylene oxide |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101481364A (en) * | 2009-02-24 | 2009-07-15 | 江苏扬农化工集团有限公司 | Continuous production method of epoxy chloropropane by hydrogen peroxide process |
CN103880783A (en) * | 2012-12-20 | 2014-06-25 | 中国科学院大连化学物理研究所 | Method for preparing epoxypropane by catalyzing propylene epoxidation with phase-transfer catalyst under reaction control |
CN206232636U (en) * | 2016-12-01 | 2017-06-09 | 中国科学院大连化学物理研究所 | A kind of catalyst recycling retracting device of epoxychloropropane processed |
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