WO2009063487A2 - Procédé amélioré pour fabriquer des résines époxydes en particulier du 2-(chlorométhyl) oxirane - Google Patents

Procédé amélioré pour fabriquer des résines époxydes en particulier du 2-(chlorométhyl) oxirane Download PDF

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Publication number
WO2009063487A2
WO2009063487A2 PCT/IN2008/000506 IN2008000506W WO2009063487A2 WO 2009063487 A2 WO2009063487 A2 WO 2009063487A2 IN 2008000506 W IN2008000506 W IN 2008000506W WO 2009063487 A2 WO2009063487 A2 WO 2009063487A2
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WO
WIPO (PCT)
Prior art keywords
epichlorohydrin
water
mixture
peroxide
allyl chloride
Prior art date
Application number
PCT/IN2008/000506
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English (en)
Other versions
WO2009063487A3 (fr
Inventor
Ajit Ramesh Joshi
Bhaskar Dattatraya Kulkarni
Raghavendra Venkatrao Naik
Shafeek Abdul Rashid Mulla
Imran Rahman
Prashant Mickey Puri
Yogesh Borole
Ananat Samdani
Narendra Singh Patil
Krishnan Narasimhan
Original Assignee
Aditya Birla Science & Technology Co. Ltd.
Aditya Birla Chemicals (Thailand) 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.)
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Publication date
Application filed by Aditya Birla Science & Technology Co. Ltd., Aditya Birla Chemicals (Thailand) Ltd filed Critical Aditya Birla Science & Technology Co. Ltd.
Publication of WO2009063487A2 publication Critical patent/WO2009063487A2/fr
Publication of WO2009063487A3 publication Critical patent/WO2009063487A3/fr

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    • 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

Definitions

  • This invention relates to an improved process for the manufacture of epoxides, particularly epichlorohydrin.
  • this invention relates to a process for manufacturing of epichlorohydrin from allyl Chloride.
  • Epichlorohydrin The largest use of Epichlorohydrin is in the manufacture of Epoxy Resins, which find applications in surface coatings. A number of surface active agents are also being made from Epichlorohydrin which is used as detergents, demulsifiers and the like .Epichlorohydrin also finds applications in the preparation of a number of pharmaceuticals, textile conditioners and dyes, paper sizing agents and the like. It is used as a solvent (e.g. for cellulose acetate) as a stabilizer for polyvinyl chloride, chlorinated rubbers and several chlorine containing insecticides, and as an additive to lubricating oil greases.
  • solvent e.g. for cellulose acetate
  • propylene is reacted with acetic acid in presence of palladium (Pd) catalyst in presence of oxygen gas to give ether.
  • Ether is reacted with hydrogen chloride in presence of CuCl or FeCl 2 and aslo in presence of organic solvent to give Allyl chloride and acetic acid.
  • This allyl chloride on hypo chlorination with C1 2 /H 2 O gives mixture of 2, 3- dichloropropanol and 1 , 2-dichloropropanol which on reaction with base as calcium hydroxide gives epichlorohydrin.
  • the main disadvantage of these processes is that the reaction of addition of hydrogen chloride is carried in presence of CuCl or FeCl 2 catalyst which is a non-aqueous system to prevent hydrolysis.
  • Epichlorohydrin is industrially manufactured by chlorination of Allyl chloride, which is obtained, by high-temperature chlorination of propylene. By-products of chlorination are cis- and trans-1,3- dichloropropene and 1,2-dichloropropane. Glycerol dichlorohydrin are made from Allyl chloride with 1, 2, 3-trichloropropane being the byproduct. Finally, Epichlorohydrin is produced from the glycerol- dichlorohydrin mixture by treatment with base. The main disadvantages are,
  • the US Patent no. 6720435, 6288248 & 6350888 disclose a process for manufacturing of epichlorohydrin by reaction of allyl chloride with a peroxide compound in the presence of water, a catalyst and a solvent followed by a liquid-liquid extraction to separate the epichlorohydrin formed.
  • the main drawbacks are, use of catalyst in powder form which reduces the rate of filtration, use of another chlorinated compound for the liquid-liquid extraction thereby increasing its recovery cost and quantity of aqueous effluents generated resulting into the increase in disposal and treatment cost.
  • US Patent no. 6380407 discloses a process for the manufacturing of an epoxide, in which an olefin is reacted with a peroxide compound in the presence of a zeolite-based catalyst and in the presence of a solvent in a reactor in the liquid phase. Gaseous compound is introduced continuously into the reactor at a flow rate which is sufficient to entrain at least some of the epoxide produced, which is recovered along with the gaseous compound at the point at which it leaves the reactor. Some of the draw backs are use of gaseous compound for carrying out the reaction which results in consumption of extra energy in preheating the compound and also for maintaining the fluidization of the solid catalyst.
  • US Patent numbers 6677467, 6723861, & 6838571 disclose processes for manufacturing oxirane by reaction of an olefin with a peroxide compound in the presence of a catalyst and a solvent in series of reactor, each of which contains a portion of catalyst, in which the peroxide compound is introduced only into the first reactor of the series and the subsequent reactor(s) not being fed with fresh peroxide compound, but only with the peroxide compound which is present in the medium obtained from the preceding reactor and which was not consumed in this preceding reactor.
  • US Patent numbers 6720435, 6288248 & 6350888 disclose processes for a liquid-liquid extraction wherein, a chlorinated compound is used for the selective extraction of epichlorohydrin from the mixture of allyl chloride, methanol, water and epichlorohydrin.
  • the extract phase contains only 10% of the epichlorohydrin produced whereas remaining 90% is in the aqueous phase.
  • the isolation of epichlorohydrin from such an aqueous phase is a grey area where no work has been reported so far.
  • One of the objects of the present invention is primarily directed to improve the overall epichlorohydrin product yield in the said process.
  • Another object of the present invention is to separate reactor product mixture into a mixture containing unconverted allyl chloride and methanol, which is Fit for the recycle.
  • Yet another object of the present invention is to use allyl chloride for recovering epichlorohydrin from aqueous phase.
  • Yet another object of the present invention is to separate water, which is fit for recycle.
  • Yet another object of the present invention is to reduce the generation of effluents substantially.
  • Yet another object of the present invention is to improve the concentration of epichlorohydrin in the organic phase and to reduce the concentration of epichlorohydrin in aqueous phase as low as possible.
  • Yet another object of the present invention is to provide a cost effective process for the production of Epichlorohydrin from Allyl Chloride.
  • a process for preparing epichlorohydrin comprising the following steps: reacting allyl chloride with an inorganic peroxide compound in the presence of at least one solvent at a temperature of about 35 to 75 degree C in a fixed bed column reactor containing a catalyst to obtain a resultant containing a mixture of epichlorohydrin, unreacted allyl chloride, solvent and water; diluting the mixture with water , wherein the mass ratio of water to the mixture is about 0.2 to 0.7, to obtain a diluted mixture; cooling the diluted mixture to about 5-15 degree C to obtain a cooled diluted mixture; separating organic phase and aqueous phase from the cooled diluted mixture; separating and recovering unreacted allyl chloride and epiochlorohydrin individually from the organic phase by fractional distillation; and separating and recovering solvent and water individually from the aqueous phase by fractional distillation.
  • FIG 1 represents the schematic diagram for the process of the present invention
  • FIG 2 represent the flow diagram of an extractor involved in the said process of the present invention as shown in FIG 1;
  • FIG 3 represents the schematic diagram of the jacketed tubular reactor for one of the alternative embodiment of the present invention.
  • FIG 1 Referring to the drawings particularly FIG 1
  • an outlet stream (OS) from the reactor (R2), containing 7-9mole % of epichlorohydrin, unreacted allyl chloride, methanol and water at around 45-50 degree C is transferred to a holding tank (Tl).
  • the effluent stream (ES) from the holding tank (Tl) is then mixed with process water (PW) from a tank (T2) and then fed to an extraction chamber (ECl).
  • the extraction chamber (ECl and EC2) consists of three separate units: a mixer (M), a cold extractor (CE) and a Decanter settler (DS), wherein the streams from the tank (Tl) and (T2) are thoroughly mixed in mixer (M) and then down streamed to a coil type cold extractor (CE) in which the reactor effluent and the process water from the mixer is led through the coil and coolant is circulated in the shell to bring down the temperature of the mixture in the coil. From the cold extractor the mixture of the reactor effluent and the process water is led to the decanter settler (DS) operatively placed below the cold extractor (CE) in the extraction chamber (EC), where a low temperature is maintained.
  • M mixer
  • CE cold extractor
  • DS Decanter settler
  • the decanter settler (DS) separation of the organic and the aqueous phase takes place by difference in densities of the two phases.
  • the organic phase settles to the bottom of the decanter settler (DS) and is extracted through the outlet of the decanter settler (DS) through organic outlet.
  • the aqueous phase is let off from the aqueous outlet of the decanter settler (DS).
  • the aqueous phase comprising mainly water and methanol with some quantities of unreacted allyl chloride and some traces of epichlorohydrin is fed to an extraction chamber (EC2) for second time extraction of epichlorohydrin by addition of allyl chloride.
  • the organic phase (OP) and aqueous phase (AP) are separated in the extraction chamber.
  • the AP from the (EC2) is passed into a fractionating column (Cl) to recover allyl chloride and methanol.
  • the (OP) from the (ECl) and (EC2) is passed into the fractionating column (C2) to obtain crude epichlorohydrin with heavies which is further fractionated in column (C3) to obtain pure epichlorohydrin.
  • the recovered allyl chloride and methanol from the column (Cl) and (C2) is recycled and mixed with the inlet stream (IS) of the reactor (Rl) and water recovered from (Cl) is fed to the water tank (T2) and inlet of Cold extraction unit.
  • the mole ratio of reactants allyl chloride: peroxide fed to the reactor is as low as 1.0: 1.0; the process also operates with 1.1-6.0: 1.0 mole ratio with minor modifications.
  • reaction is carried out at temperatures ranging from 35 to 75 degree C.
  • the intermediate stream coming out of the second reactor is maintained at 5-15 degree C for optimal results.
  • the mass flow rate of ES/PW is maintained in the range of 0.2 to 0.7.
  • the residence time of the mixture in the extractor ranges between 45 to 150 minutes.
  • the difference in specific gravity of settler liquids is maintained between 0.2-0.70 g per ml for optimal results.
  • the Epichlorohydrin so obtained is 99.9 % pure, free from other volatile impurities like methyl glycidyl ether or 2-methoxy-l- propanol or any other chloro-compounds.
  • the yield of epichlorohydrin based on hydrogen per oxide across the reactor is 97.1 % and across the extraction is 98. 1 % and based on allyl chloride, the process yield is 95.1 %.
  • figure 1 discloses one of the embodiments where in, the catalytic oxidation of allyl chloride takes place in jacketed (J) tubular reactors (Rl and R2) containing packed catalyst.
  • Inlet stream (IS) containing the reactants, allyl chloride (ALC), methanol (MeOH) and one part of fresh hydrogen peroxide (HP) is passed into the reactor Rl, and the second part of fresh Hydrogen Peroxide is passed into the second Reactor (R2).
  • an outlet stream (OS) from the reactor R2, containing epichlorohydrin (ECH), unreacted allyl chloride, methanol and water is transferred to a holding tank (Tl).
  • the effluent stream (ES) from the holding tank Tl is then mixed with process water (PW) and then fed to an extraction chamber (ECl).
  • the organic phase (OP) and aqueous phase (AP) get separated in the extraction chamber (ECl).
  • the aqueous phase (AP) from the ECl is passed into the EC2, in which second time extraction of ECH takes place by adding ALC to the extraction chamber EC2.
  • the OP from the ECl and EC2 is passed into the column C2, however the AP from the EC2 is passed into the Cl .
  • the recovered ALC, MeOH from the Cl and C2 and process water from Cl are recycled and reused.
  • the crude ECH obtained from the C2 is fed to a C3 to obtain pure ECH and heavies.
  • the mass flow rate of ES/PW is maintained in the range of 0.2 to 0.7.
  • the extraction chambers consist of three separate units: a premixer (M), a cold extractor (CE) and a Decanter settler (DS) as shown in Figure 2.
  • the premixer M is a preferred embodiment for proper mixing of two streams.
  • the premixer M comprises glass beads wherein streams from Tl and T2 are thoroughly mixed before flowing downstream to a cold extractor CE.
  • the cold extractor (CE) is a coil type of cooler in which the reactor effluent and the process water is led through the coil and coolant is circulated through the coolant inlet (IC) in the shell to bring down the temperature of the mixture in the coil to between 5 to 15 degree C and exits at the outlet (OC).
  • the residence time of the mixture in the extractor ranges between 45 to 150 minutes.
  • the mixture of the reactor effluent and the process water is led to the decanter settler (DS) placed below the cold extractor (CE) in the extraction chamber EC, where the temperature of the mixture is maintained to around 5 to 15 degree C.
  • the separation of organic and aqueous phase takes place by difference in densities of the two phases, in which the organic phase settles to the bottom of the decanter settler (DS) and is extracted through the outlet of the decanter settler (DS) through organic outlet.
  • the resident time of the split phase content and the levels of the two phases are carefully controlled.
  • the aqueous phase is let off from the aqueous outlet of the decanter settler (DS).
  • the organic phase and the aqueous phase are collected from their respective outlet by siphon.
  • the aqueous phase after the EC2 typically consists of mainly water and methanol with some quantities of unreacted allyl chloride and some traces of ECH.
  • the organic phases obtained from the column Cl and C2 typically consists of epichlorohydrin, unreacted allyl chloride, and Methanol with some traces of water.
  • the organic phase is led to the column (C2) where the crude epichlorohydrin is obtained and is led to the column (C3) to obtain high purity epichlorohydrin as a side product.
  • the recovered ALC and MeOH from the column Cl and C2 is recycled and mixed with the inlet stream (IS) of the reactor (Rl).
  • the aqueous stream is led to the column (Cl) where essentially, methanol and allyl chloride and water get separated.
  • the recovered ALC, MeOH and water from column Cl is sent back to the inlet of Reactor Rl and to the inlet of cold Extraction unit respectively.
  • the effluent stream from the reactor R2 can be recirculated several times in the same reactor by suitably adjusting the feed ratio that is hydrogen peroxide to allyl chloride.
  • This method of industrial manufacturing of the Epichlorohydrin from Allyl Chloride is more cost effective. Use of catalyst in the extrudates form reduces its cost of recovery and regeneration. Thus the operating cost in terms of the recovery of unconverted Allyl Chloride is reduced considerably.
  • the production method of the present this invention reduces the consumption of utility steam on an overall basis compared to that being practiced industrially as the best. Thus, reduces the operating cost per unit weight of production of Epichlorohydrin, increases the overall yield of product epichlorohydrin and also improves the stability of all the downstream unit operations owing to less concentration of ECH in the aqueous phase. Thus in the method of this invention, as compared to the usual methods, high quality product is obtained in relatively high yield at comparatively lower operating cost of production. The method disclosed by this invention gives quality product Epichlorohydrin at lower operating cost.
  • the main advantages of the present invention are:
  • This method permits the epoxidation reaction of the allyl chloride to be carried out in fixed bed of catalyst using a split flow of peroxide component.
  • Process water is recovered, recycled and reused in the cold extraction operation, thereby reducing the unit consumption of process water.
  • the method covered by this invention reduces the total operating cost of the production of Epichlorohydrin from allyl chloride.
  • the stream at the exit of first reactor contains Allyl chloride (32.36 mole%), Methanol (52.05 mole%), Epichlorohydrin (3.97 mole%), & Water (11.57 mole%), which is mixed with the second part of Hydrogen Peroxide and is fed into the second reactor, which is also a fixed bed tubular jacketed reactor, containing 15 gms of catalyst on a continuous basis to produce Epichlorohydrin.
  • the stream at the exit of second reactor contains Allyl chloride (25.39 mole %), Methanol (46.11 mole %), Epichlorohydrin (7.54 mole %), & Water (20.91 mole %).
  • the second reactor effluent at a rate of 46 gms/hr is mixed with DM water in specially designed extractor equipment before chilled to 5 degree C.
  • the weight ratio between process stream and water is maintained at 0.4.
  • two clear phases are separated.
  • the bottom or organic layer is withdrawn at a rate of 28.09 gms/hr and contains Allyl chloride (59.80 mole %), Methanol (11.51 mole %), Epichlorohydrin (24.68 mole%), & Water (4.00 mole%).
  • the stream at the exit of first reactor contains Allyl chloride (35.36 mole%), Methanol (45.87 mole%), Epichlorohydrin (4.25 mole%), & Water (14.48 mole%), which is mixed with the second part of Hydrogen Peroxide and is fed into the second reactor, which is also a fixed bed tubular jacketed reactor, containing 800 gms of catalyst on a continuous basis to produce Epichlorohydrin.
  • the stream at the exit of second reactor contains Allyl chloride (26.17 mole%), Methanol (46.16 mole%), Epichlorohydrin (8.06 mole%), & Water (19.57 mole%).
  • the second reactor effluent at a rate of 2020 gms/hr is mixed with DM water in specially designed extractor equipment before chilled to 5 degree C.
  • the weight ratio between process stream and water is maintained at 0.4.
  • two clear phases are separated.
  • the bottom or organic layer is withdrawn at a rate of 1233.52 gms/hr and contains Allyl chloride (62.39 mole %), Methanol (14.25 mole%), Epichlorohydrin (19.93 mole%), & Water (3.42 mole%).

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

Abstract

Cette invention concerne un procédé permettant de préparer du 2-(chlorométhyl) oxirane et comprenant les étapes qui consistent à faire réagir du chlorure d'allyle avec un composé inorganique à base de peroxyde en présence d'au moins un solvant à une température d'environ 35 à 75 degrés celsius dans un réacteur à colonnes à lit fixe contenant un catalyseur pour obtenir un produit contenant un mélange de 2-(chlorométhyl) oxirane, de chlorure d'allyle n'ayant pas subi de réaction, de solvant et d'eau; à diluer le mélanger avec de l'eau, le rapport de masse de l'eau eet du mélange étant compris entre 0.2 et 0.7, afin d'obtenir un mélange dilué refroidi; à séparer la phase organique et la phase aqueuse du mélange dilué refroidi; à séparer puis à récupérer le chlorure d'allyle n'ayant pas subi de réaction ainsi que le 2-(chlorométhyl) oxirane individuellement à partir de la phase organique par distillation fractionnée; puis à séparer et à récupérer le solvant et l'eau individuellement à partir de la phase aqueuse par distillation fractionnée.
PCT/IN2008/000506 2007-08-10 2008-08-11 Procédé amélioré pour fabriquer des résines époxydes en particulier du 2-(chlorométhyl) oxirane WO2009063487A2 (fr)

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IN1558/MUM/2007 2007-08-10

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012106630A1 (fr) * 2011-02-04 2012-08-09 Dow Global Technologies Llc Séparation des phases d'un mélange
CN102666517A (zh) * 2009-11-19 2012-09-12 陶氏环球技术有限责任公司 环氧化丙烯
CN102746257A (zh) * 2012-07-03 2012-10-24 淮阴工学院 氯丙烯环氧化制备环氧氯丙烷的方法
CN103030610A (zh) * 2011-09-29 2013-04-10 中国石油化工股份有限公司 氯丙烯氧化制环氧氯丙烷的方法
US8481765B2 (en) 2008-03-17 2013-07-09 Momentive Specialty Chemicals Inc. Method for the production of epichlorohydrin
CN103420949A (zh) * 2012-05-18 2013-12-04 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420948A (zh) * 2012-05-18 2013-12-04 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420946A (zh) * 2012-05-18 2013-12-04 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
US8729282B2 (en) 2008-08-01 2014-05-20 Momentive Specialty Chemicals Inc. Process for the manufacture of a 1,2-epoxide
US8735613B2 (en) 2009-11-27 2014-05-27 Momentive Specialty Chemicals Inc. Process for the manufacture of propylene oxide
US8802873B2 (en) 2008-08-01 2014-08-12 Momentive Specialty Chemicals Inc. Process for the manufacture of epichlorohydrin
US8859790B2 (en) 2010-02-02 2014-10-14 Momentive Specialty Chemicals Inc. Process for the manufacture of a 1,2-epoxide and a device for carrying out said process
US8927744B2 (en) 2011-11-04 2015-01-06 Dow Global Technologies Llc Process and system for producing an oxirane
US8980780B2 (en) 2011-02-04 2015-03-17 Dow Global Technologies Llc Regenerating a titanium silicalite catalyst
US9498762B2 (en) 2011-02-04 2016-11-22 Blue Cube Ip Llc System and process for producing an oxirane

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TWI622584B (zh) * 2017-05-02 2018-05-01 國立清華大學 以氯丙烯與雙氧水反應生產環氧氯丙烷的製造裝置及製造方法

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WO2002000636A1 (fr) * 2000-06-28 2002-01-03 Solvay (Societe Anonyme) Procede de fabrication d'oxiranne

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WO2002000636A1 (fr) * 2000-06-28 2002-01-03 Solvay (Societe Anonyme) Procede de fabrication d'oxiranne

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8481765B2 (en) 2008-03-17 2013-07-09 Momentive Specialty Chemicals Inc. Method for the production of epichlorohydrin
US8802873B2 (en) 2008-08-01 2014-08-12 Momentive Specialty Chemicals Inc. Process for the manufacture of epichlorohydrin
US8729282B2 (en) 2008-08-01 2014-05-20 Momentive Specialty Chemicals Inc. Process for the manufacture of a 1,2-epoxide
CN102666517B (zh) * 2009-11-19 2014-12-17 陶氏环球技术有限责任公司 环氧化丙烯
CN102666517A (zh) * 2009-11-19 2012-09-12 陶氏环球技术有限责任公司 环氧化丙烯
US8735613B2 (en) 2009-11-27 2014-05-27 Momentive Specialty Chemicals Inc. Process for the manufacture of propylene oxide
US8859790B2 (en) 2010-02-02 2014-10-14 Momentive Specialty Chemicals Inc. Process for the manufacture of a 1,2-epoxide and a device for carrying out said process
US9102640B2 (en) 2010-02-02 2015-08-11 Evonik Degussa Gmbh Process for the manufacture of a 1,2-epoxide and a device for carrying out said process
US8754246B2 (en) 2011-02-04 2014-06-17 Dow Global Technologies, Llc Separating phases of a mixture
US9498762B2 (en) 2011-02-04 2016-11-22 Blue Cube Ip Llc System and process for producing an oxirane
CN105439983A (zh) * 2011-02-04 2016-03-30 蓝立方知识产权有限责任公司 混合物的相分离
CN103547574A (zh) * 2011-02-04 2014-01-29 陶氏环球技术有限责任公司 混合物的相分离
US8980780B2 (en) 2011-02-04 2015-03-17 Dow Global Technologies Llc Regenerating a titanium silicalite catalyst
WO2012106630A1 (fr) * 2011-02-04 2012-08-09 Dow Global Technologies Llc Séparation des phases d'un mélange
CN103030610B (zh) * 2011-09-29 2016-05-18 中国石油化工股份有限公司 氯丙烯氧化制环氧氯丙烷的方法
CN103030610A (zh) * 2011-09-29 2013-04-10 中国石油化工股份有限公司 氯丙烯氧化制环氧氯丙烷的方法
US8927744B2 (en) 2011-11-04 2015-01-06 Dow Global Technologies Llc Process and system for producing an oxirane
CN103420946A (zh) * 2012-05-18 2013-12-04 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420948A (zh) * 2012-05-18 2013-12-04 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420949A (zh) * 2012-05-18 2013-12-04 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420948B (zh) * 2012-05-18 2016-05-25 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420949B (zh) * 2012-05-18 2016-05-25 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN102746257A (zh) * 2012-07-03 2012-10-24 淮阴工学院 氯丙烯环氧化制备环氧氯丙烷的方法

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