CN104557782A - Method for preparing epoxypropane from cumyl hydroperoxide and propylene - Google Patents
Method for preparing epoxypropane from cumyl hydroperoxide and propylene Download PDFInfo
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- CN104557782A CN104557782A CN201310512323.4A CN201310512323A CN104557782A CN 104557782 A CN104557782 A CN 104557782A CN 201310512323 A CN201310512323 A CN 201310512323A CN 104557782 A CN104557782 A CN 104557782A
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- propylene
- hydrogen phosphide
- phosphide cumene
- propylene oxide
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- 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
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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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
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
Abstract
The invention relates to a method for preparing epoxypropane from cumyl hydroperoxide and propylene. The method is mainly used for solving the problems in the prior art that the reaction temperature rise is high and that a higher molar ratio of the propylene to the cumyl hydroperoxide is needed to keep higher reaction efficiency. The following technical scheme is used for solving the problem in the invention: the raw materials, namely the cumyl hydroperoxide and the propylene enter a multi-segment adiabatic reaction area including at least two segments, and the raw materials touch a Ti-silicon dioxide catalyst to carry out an epoxidation reaction to generate the epoxypropane, wherein the epoxidation reaction temperature is 15-160 DEG C, the pressure is 1.0-12.0 MPa, and the total molar ratio of the propylene to the cumyl hydroperoxide is 2-30; and the cumyl hydroperoxide enters the catalyst bed layers of the multi-segment adiabatic reaction area in segments; the epoxidation reaction product part containing the epoxypropane is recycled to the inlet of the multi-segment adiabatic reaction area. The method can be applied to the industrial production of preparing epoxypropane from cumyl hydroperoxide and propylene.
Description
Technical field
The present invention relates to a kind of method of hydrogen phosphide cumene and propylene propylene oxide.Background technology
Propylene oxide is important basic chemical industry raw material, is the third-largest propylene analog derivative being only second to polypropylene and vinyl cyanide, mainly for the production of polyethers, propylene glycol etc.It is also the main raw material of forth generation washing composition nonionogenic tenside, oil field demulsifier, farm chemical emulgent etc.The derivative of propylene oxide is widely used in the industries such as automobile, building, food, tobacco, medicine and makeup.The derived product of having produced nearly hundred kinds is the important source material of fine chemical product.
The traditional processing technology of propylene oxide is chlorohydrination technique, and process comprises the chlorohydrination of propylene and hypochlorite solution, propylene chlorohydrin and milk of lime saponification and product purification three steps.The feature of this method is that flow process is shorter, and construction investment is few, technical maturity, not high to raw material propylene purity requirement.But owing to using chlorine in production process, produce the waste water of a large amount of chloride containing calcium, have corrosion to equipment, there is serious problem of environmental pollution.
For the problem of environmental pollution that chlorohydrination technique exists, the companies such as Lyondell develop co-oxidation propylene oxide green synthesis process.Conjugated oxidation is divided into Trimethylmethane conjugated oxidation and ethylbenzene conjugated oxidation two kinds of joint process, the former coproduction trimethyl carbinol, the latter's coproduction vinylbenzene, and its basic step is: (1) Trimethylmethane or ethylbenzene oxidation are corresponding superoxide; (2) propylene is produced propylene oxide and corresponding alcohol by superoxide epoxidation; (3) propylene oxide is refined; (4) be converted into can product sold for coproduction alcohol.Compared with chlorohydrination, conjugated oxidation overcomes environmental pollution, the equipment corrosion of chlorohydrination existence and consumes the shortcomings such as chlorine, but this method weak point is that technical process is long, investment cost is high (being about 2 times of chlorohydrination), and a large amount of joint product (joint product output is about 2 ~ 3 times of PO) need be balanced, the economic benefit certain degree of therefore conjugated oxidation depends on the sale of joint product.
To this, many companies are devoted to develop the propylene oxide Green Manufacturing Technology without coproduction.The companies such as Degussa and Krupp Unde and BASF and Dow are " HPPO " production technology of oxygenant with hydrogen peroxide in cooperative development.This method for raw material, take methyl alcohol as solvent with chemical grade propylene and hydrogen peroxide, adopts tubular reactor, reacts at the temperature and low pressure of gentleness in liquid phase.Hydrogen peroxide transforms completely, and propylene is Quantitative yield almost, only generates propylene oxide and water in production process, unreacting propylene can be used for other process or recycles, and technical process is simple, and product yield is high, there is no other joint product, substantially pollution-free, belong to eco-friendly process for cleanly preparing.The shortcoming of this technique is that hydrogen peroxide consumption is large, and propylene oxide per ton consumes hydrogen peroxidase 10 .7 ton.
SUMITOMO CHEMICAL chemical company develops the conjugated oxidation technique without by-product.This technique adopts isopropyl benzene to substitute Trimethylmethane or ethylbenzene, cumene oxidation is become hydrogen phosphide cumene (CHP), epoxidation of propylene is made to become propylene oxide with CHP again, the dimethyl benzyl alcohol simultaneously obtained can obtain alpha-methyl styrene after dewatering, and then hydrogenation becomes isopropyl benzene for recycling.Compared with traditional PO/SM co-production method, this method production equipment takes up an area few, and capital construction investment expense is few, without coproduction chemical, can reduce the market risk because a large amount of by-product of coproduction brings.
Some patents are had to relate to conjugated oxidation technique without coproduction, as US5760253A, JP63-107873A, US3350422, US5489366A, US5319114A, ZL03803981.8 etc.CN101636393A discloses a kind of method for the preparation of propylene oxide, comprises epoxidation step, makes organo-peroxide and propylene react in the presence of a catalyst to obtain propylene oxide and alcohol; Propylene recovery step, reclaims unreacted propylene in described epoxidation step and using the raw material of gained propylene recirculation as described epoxidation step; And propylene oxide purification step, the propylene oxide obtained in described epoxidation step is distilled with the propylene oxide obtaining purifying.ZL02821008.5 discloses a kind of manufacture method of propylene oxide, comprises and makes cumene oxidizingly to obtain cumene hydroperoxide; In the presence of an epoxidation catalyst, this cumene hydroperoxide and propylene is made to be obtained by reacting propylene oxide and 2-phenyl-2-propyl alcohol; To epoxidised go out oral fluid refine, make it to be separated into the cut containing crude propene oxide and the cut containing crude propylene; Cut containing crude propene oxide is refined, obtains containing crude propene oxide and the cut containing 2-phenyl-2-propyl alcohol; Rectifying is carried out to crude propene oxide, obtains containing smart product propylene; Rectifying is carried out to the cut containing crude propylene, obtains fine propylene; Simultaneous oxidation and/or epoxidation reaction heat are used for the rectifying separation of reaction solution.The manufacture method of the propylene oxide that W02001/070715, ZL02826922.5 disclose adds isopropyl benzene through being oxidized the operation of obtained isopropyl benzene hydroperoxide compared with CN101636393A, and the isopropylbenzyl alcohol hydrogenolysis will obtained in epoxidation process, obtain isopropyl benzene, using this isopropyl benzene as the raw material in oxidation operation, be circulated to the operation of oxidation operation.The temperature of isopropylbenzene hydroperoxide logistics is specified simultaneously.
In existing document or report, how the reaction process problem of shorter mention hydrogen phosphide cumene and propylene to prepare epoxy propane, particularly effectively reduce reaction temperature rising, the raising propylene of reaction bed and the problem of the mol ratio of hydrogen phosphide cumene.
Summary of the invention
Technical problem to be solved by this invention is that prior art exists the higher and problem for keeping higher reaction efficiency to need higher propylene and hydrogen phosphide cumene mol ratio of reaction temperature rising, provides a kind of method of new hydrogen phosphide cumene and propylene propylene oxide.The method, under the prerequisite of total mol ratio not increasing propylene and hydrogen phosphide cumene, effectively can reduce reaction temperature rising, improve the reaction propylene of beds and the mol ratio of hydrogen phosphide cumene.
In order to solve the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of method of hydrogen phosphide cumene and propylene propylene oxide, raw material hydrogen peroxide isopropyl benzene and propylene liquid phase enter the multistage insulation reaction zone being at least two sections, epoxidation reaction temperature be 15 ~ 160 DEG C, under pressure be total mol ratio of 1.0 ~ 12.0MPa, propylene and hydrogen phosphide cumene is the condition of 2 ~ 30, raw material contacts with Ti-SiO 2 catalyst and carries out epoxidation reaction and generate propylene oxide; Wherein, the segmentation of raw material hydrogen peroxide isopropyl benzene enters each beds of multistage insulation reaction zone; The epoxidation reaction product section containing propylene oxide that the outlet of multistage insulation reaction zone obtains is circulated to multistage insulation reaction zone entrance.
In technique scheme, preferably, the extraction logistics of epoxidation reaction product and the weight ratio of recycle stream are 0.1 ~ 10.More preferably, the extraction logistics of epoxidation reaction product and the weight ratio of recycle stream are 0.5 ~ 5.
In technique scheme, preferably, described multistage insulation reaction zone is the adiabatic reactor of at least two sections, or by the reaction zone of at least two single stage adiabatic reactors in series, or the reaction zone that at least one single stage adiabatic reactor and at least one adiabatic reactor of at least two sections are in series.
In technique scheme, preferably, the adiabatic reactor of described at least two sections is composed in series by 2 ~ 10 beds.More preferably, the adiabatic reactor of described at least two sections is composed in series by 2 ~ 4 beds.
In technique scheme, it can be upflowing that the logistics in reaction zone flows to, and also can be downflow system.Preferably, it is upflowing that the logistics in described reaction zone flows to.
In technique scheme, preferably, to enter the hydrogen phosphide cumene ratio of each beds in multistage insulation reaction zone identical in segmentation.
In technique scheme, preferably, raw material propylene is fresh propylene, the Propylene recovery of follow-up system or its mixture.
In technique scheme, preferably, raw material hydrogen peroxide isopropyl benzene is obtained by cumene oxidation, is the mixture of isopropyl benzene and hydrogen phosphide cumene.More preferably, when hydrogen phosphide cumene is when containing the mixture as the isopropyl benzene of its raw material, this mixture can be used to replace solvent when not adding solvent.Wherein, hydrogen phosphide cumene concentration is 10 ~ 70 % by weight.
In technique scheme, preferably, described epoxidation reaction is carried out in the liquid phase using solvent, is liquid, and does not substantially react with reactant and product under the temperature and pressure of described solvent when reacting.
In technique scheme, each section of hydrogen phosphide cumene charging both can mix outward at reactor with reaction mass, also can mix in reactor, and middle heat collector can be adopted between each reactor, between each beds where necessary to remove reaction heat.
In technique scheme, preferably, epoxidation reaction temperature is 30 ~ 130 DEG C, and pressure is total mol ratio of 1.5 ~ 6.0MPa, propylene and hydrogen phosphide cumene is 4 ~ 20.
Epoxidation reaction temperature is generally 15 DEG C to 160 DEG C, considers economic utilization and the reaction preference of speed of reaction and catalyzer, preferably 30 DEG C to 130 DEG C.When the temperature is too low, speed of reaction is too low, and the amount therefore obtaining the catalyzer needed for required reacting weight increases.On the contrary, when temperature is too high, selectivity reduces, and catalyst regeneration cycle shortens.Particularly, when the amount of the compound with 4 carbon atoms increases, loss and the energy required when removing compound of valuable constituent increase.Pressure can be enough to keep reaction mixture to be in the pressure of liquid state, is generally 1.0 ~ 12.0 MPa, preferably 1.5 ~ 6.0 MPa.
Total mol ratio of the mol ratio propylene and hydrogen phosphide cumene that are supplied to the propylene/hydrogen phosphide cumene of epoxidation step is generally 2 ~ 30, and preferably 4 ~ 20, most preferably 6 ~ 15.When this ratio is too low, speed of reaction reduces, and reaction preference is deteriorated, and the yield of object product will reduce.When this ratio is too high, the quantitative change of the propylene of recirculation obtains and excessively increases, and therefore in recycling step, needs many energy, and the energy consumption of device is increased.
Owing to adopting the multistage insulation fixed bed reaction process of the intersegmental cooling of raw material hydrogen peroxide isopropyl benzene and the circulation of epoxidation reaction product section in the present invention, can partly or entirely absorption reaction heat, effectively control reaction temperature rising, improve the propylene of beds and the ratio of hydrogen phosphide cumene, ensure that epoxidation reaction is carried out under the reaction conditions of the best, the selectivity of object product propene oxide can be improved.Adopt technical scheme of the present invention, the insulation fix bed reaction process of two-section type, epoxidised reaction temperature rising is only 20.2 DEG C, lower than 37 in comparative example DEG C, under total propylene and hydrogen phosphide cumene mol ratio are the condition of 10.1, the mol ratio of beds is up to 38.5, and hydrogen phosphide cumene almost all transforms, the selectivity of object product propene oxide reaches 96.4%, achieves good technique effect.
Accompanying drawing explanation
Fig. 1 is the schematic diagram of the method for hydrogen phosphide cumene of the present invention and propylene propylene oxide.
In Fig. 1,1 is raw material hydrogen peroxide cumene mixture, 2 for entering the hydrogen phosphide cumene mixture of the first beds, 3 for entering the hydrogen phosphide cumene mixture of the second beds, 4 for entering the hydrogen phosphide cumene mixture of the n-th beds, 5 is raw material propylene, 6 is the recycle stream of peroxidation reaction product, 7 is the peroxidation reaction product containing propylene oxide, 1a is mutil-stage adiabatic reactor, and 2a is the first beds, and 3a is the second beds, 4a is the n-th beds, and 5a is reactor inlet water cooler.
In Fig. 1, raw material hydrogen peroxide cumene mixture 1 is divided into logistics 2, logistics 3, logistics 4, enter the first beds 2a of liquid-solid phase multistage insulation fixed bed reactor 1a, the second beds 3a, the n-th beds 4a respectively, raw material propylene 5 enters the first beds 2a of multistage insulation fixed bed reactor 1a.Propylene and hydrogen phosphide cumene contact with Ti-SiO 2 catalyst and carry out epoxidation reaction, and epoxidation reaction product is divided into recycle stream 6 and the reaction product stream 7 containing propylene oxide.Wherein, recycle stream 6 loops back the water cooler of reactor inlet, and the reaction product stream 7 containing propylene oxide goes follow-up separation and purification unit to carry out separation and purification to obtain qualified product propylene.
The advantage of the inventive method is:
1, multistage insulation fixed bed reaction process is adopted, raw material is divided into multiply material and enters each beds, directly mix with reactant flow, can partly or entirely absorption reaction heat, the temperature of reaction effectively controlling every section of beds, in suitable scope, ensure that epoxidation reaction is carried out under the temperature of reaction condition of the best.
2, low propylene and the mol ratio of hydrogen phosphide cumene can more be adapted to.By the ratio of adjustment reaction hop count, intersegmental feed product flow and every section of propylene and hydrogen phosphide cumene, reach the propylene circulation ratio reducing epoxidation reaction system, reduce energy consumption, reduce the object of investing.
3, adopt the intersegmental cooling of raw material hydrogen peroxide isopropyl benzene and and epoxidation reaction product section circulation multistage insulation fixed bed reaction process, effectively control reaction temperature rising, improve the propylene ratio of beds, the selectivity of object product propene oxide can be improved.
4, because reaction temperature rising is lower, can suitably improve reactor inlet temperature of reaction, improve speed of response; Or the temperature of reaction of reactor outlet can be reduced, can reaction pressure be reduced under the condition keeping whole reaction zone in liquid phase.
Below by embodiment, the present invention is further elaborated.
Embodiment
[embodiment 1]
By the technical scheme shown in Fig. 1, raw material is containing the hydrogen phosphide cumene mixture of 35% weight concentration, flow is 101166.1 kgs/hr, 1:1 is divided into two strands in proportion, enter the insulation fix bed reactor of two-part respectively, raw material propylene 10812.7 kgs/hr, circulation propylene 92993.1 kgs/hr, Cyclic Rings oxidation reaction product 136647.8 kgs/hr, mix with the hydrogen phosphide cumene mixture entering the first beds, temperature of reaction 55 DEG C, under the condition of reaction pressure 3.1MPaG, with Ti/SiO
2catalyst exposure, liquid phase epoxidation reaction generates propylene oxide and dimethyl benzyl alcohol and other by product; The reactant flowing out the first beds mixes with the hydrogen phosphide cumene mixture entering the second beds, and control temperature 55 DEG C, enters the second beds, with Ti/SiO
2catalyst exposure, liquid phase epoxidation reaction generates propylene oxide and dimethyl benzyl alcohol and other by product.Hydrogen phosphide cumene weight space velocity 4.5hr
-1total propylene and the mol ratio of hydrogen phosphide cumene are 10.2, the propylene of the first beds and the second beds entrance and the mol ratio of hydrogen phosphide cumene then reach 38.5 and 27.3, the temperature out of the first beds and the second beds is respectively 73.0 DEG C, 75.2 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.3%, and the molar selectivity of propylene oxide is 96.4%.
[embodiment 2]
With [embodiment 1], only change the flow of recycle stream: circulation propylene flow is 61995.4 kgs/hr, Cyclic Rings oxidation reaction product 115982.6 kgs/hr, other is with [embodiment 1].Hydrogen phosphide cumene weight space velocity 4.5hr
-1total propylene and the mol ratio of hydrogen phosphide cumene are 7.1, the propylene of the first beds and the second beds entrance and the mol ratio of hydrogen phosphide cumene then reach 26.5 and 18.6, the temperature out of the first beds and the second beds is respectively 77.3 DEG C, 79.1 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.2%, the molar selectivity of propylene oxide is 96.1%
[embodiment 3]
With [embodiment 1], an altering reactor form: two single bed insulation fix bed reactor series connection, other is with [embodiment 1].Hydrogen phosphide cumene weight space velocity 4.5hr
-1total propylene and the mol ratio of hydrogen phosphide cumene are 10.2, the propylene of the first beds and the second beds entrance and the mol ratio of hydrogen phosphide cumene then reach 38.5 and 27.3, the temperature out of the first beds and the second beds is respectively 73.0 DEG C, 75.2 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.3%, and the molar selectivity of propylene oxide is 96.4%.
[embodiment 4]
With [embodiment 1], an altering reactor temperature in: reactor catalyst bed inlet temperatures is 58 DEG C, other is with [embodiment 1].Hydrogen phosphide cumene weight space velocity 4.5hr
-1total propylene and the mol ratio of hydrogen phosphide cumene are 10.2, the propylene of the first beds and the second beds entrance and the mol ratio of hydrogen phosphide cumene then reach 38.5 and 27.3, the temperature out of the first beds and the second beds is respectively 76.0 DEG C, 78.2 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.35%, and the molar selectivity of propylene oxide is 96.3%.
[comparative example]
Epoxidation reactor is single stage adiabatic fixed-bed reactor, raw material is containing the hydrogen phosphide cumene mixture of 35% weight concentration, flow is 101166.1 kgs/hr, mix with raw material propylene 10812.7 kgs/hr, circulation propylene 92993.1 kgs/hr, entrance temperature of reaction 55 DEG C, under the condition of reaction pressure 3.1MPaG, with Ti/SiO
2catalyst exposure, liquid phase epoxidation reaction generates propylene oxide and dimethyl benzyl alcohol and other by product, hydrogen phosphide cumene weight space velocity 4.5hr
-1, total propylene and the mol ratio of hydrogen phosphide cumene are 10.2, and the temperature out of reactor is 91.7 DEG C, and the total conversion rate of hydrogen phosphide cumene is 99.2%, and the molar selectivity of propylene oxide is 95.3%.
Claims (10)
1. the method for a hydrogen phosphide cumene and propylene propylene oxide, raw material hydrogen peroxide isopropyl benzene and propylene liquid phase enter the multistage insulation reaction zone being at least two sections, epoxidation reaction temperature be 15 ~ 160 DEG C, under pressure be total mol ratio of 1.0 ~ 12.0MPa, propylene and hydrogen phosphide cumene is the condition of 2 ~ 30, raw material contacts with Ti-SiO 2 catalyst and carries out epoxidation reaction and generate propylene oxide; Wherein, the segmentation of raw material hydrogen peroxide isopropyl benzene enters each beds of multistage insulation reaction zone; The epoxidation reaction product section containing propylene oxide that the outlet of multistage insulation reaction zone obtains is circulated to multistage insulation reaction zone entrance.
2. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 1, is characterized in that the extraction logistics of epoxidation reaction product and the weight ratio of recycle stream are 0.1 ~ 10.
3. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 2, is characterized in that the extraction logistics of epoxidation reaction product and the weight ratio of recycle stream are 0.5 ~ 5.
4. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 1, it is characterized in that described multistage insulation reaction zone is the adiabatic reactor of at least two sections, or by the reaction zone of at least two single stage adiabatic reactors in series, or the reaction zone that at least one single stage adiabatic reactor and at least one adiabatic reactor of at least two sections are in series.
5. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 4, described in it is characterized in that, the adiabatic reactor of at least two sections is composed in series by 2 ~ 10 beds.
6. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 5, described in it is characterized in that, the adiabatic reactor of at least two sections is composed in series by 2 ~ 4 beds.
7. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 1, it is characterized in that in described multistage insulation reaction zone that logistics flows to is upflowing.
8. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 1, is characterized in that segmentation enters the hydrogen phosphide cumene ratio of each beds in multistage insulation reaction zone identical.
9. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 1, is characterized in that raw material propylene is fresh propylene, the Propylene recovery of follow-up system or its mixture; Raw material hydrogen peroxide isopropyl benzene is obtained by cumene oxidation, is the mixture of isopropyl benzene and hydrogen phosphide cumene; Wherein, hydrogen phosphide cumene concentration is 10 ~ 70 % by weight; Described epoxidation reaction is carried out in the liquid phase using solvent, is liquid, and does not substantially react with reactant and product under the temperature and pressure of described solvent when reacting.
10. the method for hydrogen phosphide cumene and propylene propylene oxide according to claim 9, it is characterized in that, when hydrogen phosphide cumene is when containing the mixture as the isopropyl benzene of its raw material, this mixture to be used to replace solvent when not adding solvent.
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| CN201310512323.4A CN104557782A (en) | 2013-10-28 | 2013-10-28 | Method for preparing epoxypropane from cumyl hydroperoxide and propylene |
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| CN201310512323.4A CN104557782A (en) | 2013-10-28 | 2013-10-28 | Method for preparing epoxypropane from cumyl hydroperoxide and propylene |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106467505A (en) * | 2015-08-20 | 2017-03-01 | 陕西煤业化工集团(上海)胜帮化工技术有限公司 | HPPO legal system expoxy propane two-part reaction method |
| CN108043331A (en) * | 2017-12-21 | 2018-05-18 | 红宝丽集团股份有限公司 | A kind of preparation method of the multistage reaction unit prepared for 1,2- epoxy butanes and 1,2- epoxy butanes |
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| EP0645380A1 (en) * | 1993-09-23 | 1995-03-29 | ARCO Chemical Technology, L.P. | Olefin epoxidation using a carbon molecular sieve impregnated with a transition metal |
| US5489366A (en) * | 1994-03-28 | 1996-02-06 | Texaco Chemical Inc. | Recovery of purified and substantially anhydrous propylene oxide |
| CN1418200A (en) * | 2000-03-24 | 2003-05-14 | 住友化学工业株式会社 | Process for producing oxirane compound |
| CN101636393A (en) * | 2007-03-22 | 2010-01-27 | 住友化学株式会社 | Method for producing propylene oxide |
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| US3350422A (en) * | 1966-02-01 | 1967-10-31 | Halcon International Inc | Catalytic epoxidation of an olefinically unsaturated compound using an organic hydroperoxide as an epoxidizing agent |
| JPS63107873A (en) * | 1986-10-24 | 1988-05-12 | ハリマセラミック株式会社 | Flame spraying material |
| EP0645380A1 (en) * | 1993-09-23 | 1995-03-29 | ARCO Chemical Technology, L.P. | Olefin epoxidation using a carbon molecular sieve impregnated with a transition metal |
| US5489366A (en) * | 1994-03-28 | 1996-02-06 | Texaco Chemical Inc. | Recovery of purified and substantially anhydrous propylene oxide |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106467505A (en) * | 2015-08-20 | 2017-03-01 | 陕西煤业化工集团(上海)胜帮化工技术有限公司 | HPPO legal system expoxy propane two-part reaction method |
| CN108043331A (en) * | 2017-12-21 | 2018-05-18 | 红宝丽集团股份有限公司 | A kind of preparation method of the multistage reaction unit prepared for 1,2- epoxy butanes and 1,2- epoxy butanes |
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Application publication date: 20150429 |
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