CN105315235A - Method used for realizing epoxidation of hydrogen peroxide ethylbenzene with propylene - Google Patents
Method used for realizing epoxidation of hydrogen peroxide ethylbenzene with propylene Download PDFInfo
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- CN105315235A CN105315235A CN201410355435.8A CN201410355435A CN105315235A CN 105315235 A CN105315235 A CN 105315235A CN 201410355435 A CN201410355435 A CN 201410355435A CN 105315235 A CN105315235 A CN 105315235A
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Abstract
The invention relates to a method used for realizing epoxidation of hydrogen peroxide ethylbenzene with propylene. The method is mainly used for solving problems of the prior art that reaction temperature rise is relatively high, and a relatively high propylene/ hydrogen peroxide ethylbenzene molar ratio is needed for maintaining a relatively high reaction efficiency. According to the method, raw materials hydrogen peroxide ethylbenzene and propylene liquid phase are delivered into a reactor, contact epoxidation reaction with Ti-silicon dioxide catalyst is carried out at a reaction temperature ranging from 15 to 160 DEGC at a pressure ranging from 1.0 to 12.0MPa so as to obtain epoxypropane, wherein the total molar ratio of propylene/ hydrogen peroxide ethylbenzene ranges from 1 to 20, and a part of an obtained epoxidation reaction product containing epoxypropane is recycled to the inlet of the reactor. The method is capable of solving the problems above preferably, and can be applied to industrial production to prepare epoxypropane via epoxidation of hydrogen peroxide ethylbenzene with propylene.
Description
Technical field
The present invention relates to a kind of method of hydrogen peroxide ethylbenzene and epoxidation of propylene.
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 company such as Degussa and KruppUnde and BASF and Dow is " 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 PO/SM co-production method, CHP method is without coproduction chemical, though the market risk because a large amount of by-product of coproduction brings can be reduced, but two kinds of explained hereafter devices, capital construction investments are more or less the same, have the market requirement to obtain countries and regions for propylene oxide and vinylbenzene, PO/SM co-production method generating apparatus economic benefit is better.
Some patents are had to relate to the conjugated oxidation technique of PO/SM co-production method.EP323663 discloses a kind of hydrogen peroxide ethylbenzene and epoxidation of propylene technique, and under the condition of temperature of reaction 100 DEG C, hydrogen peroxide ethylbenzene and propylene enter reactor, with Ti/SiO with the mol ratio of 16.7
2catalyst exposure reacts, and generates propylene oxide, reactor outlet pressure 26bar, and volatile components (as propylene) vaporization absorption epoxidation reaction heat, to maintain the temperature of reaction of reactor.US6153153 discloses a kind of epoxidation processes be made up of multiple adiabatic reaction district, raw material hydrogen peroxide ethylbenzene and propylene are with the mixed in molar ratio of 4.65:1, be divided into the reactant flow that multiple logistics cools each reaction zone respectively, reactor is entered to 80 ~ 107 DEG C with the hot reacting by heating raw material of epoxidation reaction, the outlet reactant decompression vaporization of last reaction zone, reduce temperature, the logistics of vaporization cools the inlet streams of last reaction zone, the temperature rise of each reaction zone keeps 6 ~ 28 DEG C, and reaction pressure is carried out in the liquid phase to keep reaction.
US5883268 discloses the treatment process of ethylbenzene oxidation product.Hydrogen peroxide ethylbenzene disclosed in US5849937 and epoxidation of propylene technique and US6153153 different, epoxidation reaction is divided into 6 catalytic reaction zones, and wherein last reaction zone is for subsequent use.Raw material hydrogen peroxide ethylbenzene and propylene are divided into the outlet material that four strands of materials cool front four reaction areas respectively, the first reaction zone is entered to 38 ~ 101 DEG C with the hot reacting by heating raw material of epoxidation reaction, reaction zone temperature out 121 DEG C, reaction pressure keeps reaction zone entirety to be liquid phase.When the catalyst activity of the first reaction zone is reduced to a certain degree, close the valve of the turnover pipeline of the first reaction zone, switch out regeneration or replacing that reactive system carries out catalyzer, the 6th reaction zone of simultaneously coming into operation, steady with retaining ring oxidizing reaction.Epoxidation technique disclosed in US5760253, reaction is divided into multiple reaction zone, material between each reaction zone and charging heat exchange, remove the reaction heat of 25 ~ 75%, remaining reaction heat promotes the temperature of reaction mass, and the component that vaporization is easily vaporized, the temperature rise of each reaction zone is generally 20 ~ 100 DEG C.
In existing document or report, in the reaction process of shorter mention hydrogen peroxide ethylbenzene and propylene to prepare epoxy propane, how effectively to improve the problem mole when reducing reaction temperature rising of the propylene of reaction bed and hydrogen peroxide ethylbenzene.
Summary of the invention
Technical problem to be solved by this invention is in prior art, it is higher and for keep higher reaction efficiency to need the problems such as the mol ratio of higher propylene and hydrogen peroxide ethylbenzene to there is reaction temperature rising in the reaction process of hydrogen peroxide ethylbenzene and propylene to prepare epoxy propane, a kind of method of new hydrogen peroxide ethylbenzene and epoxidation of propylene is provided, the method, under the prerequisite of total mol ratio not increasing propylene and hydrogen peroxide ethylbenzene, effectively can reduce reaction temperature rising, improve the reaction propylene of beds and the mol ratio of hydrogen peroxide ethylbenzene.
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 peroxide ethylbenzene and epoxidation of propylene, raw material I containing hydrogen peroxide ethylbenzene and the raw material II containing propylene, liquid-phase mixing raw material enters reactor, it is 15 ~ 160 DEG C in epoxidation reaction temperature, pressure is 1.0 ~ 12.0MPa, total mol ratio of propylene and hydrogen peroxide ethylbenzene is under the condition of 1 ~ 20, to contact with Ti-SiO 2 catalyst in the liquid phase using solvent and carry out epoxidation reaction and generate propylene oxide, epoxidation reaction product wherein containing propylene oxide is divided into extraction logistics and recycle stream, wherein recycle stream is circulated to reactor inlet.
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, reactor is divided into two types: the first reactor: be only single reactor, and wherein, in reactor, reaction bed is single hop bed or multistage bed; The second reactor: be made up of at least two reactors in series, the catalyst reactor bed of wherein connecting is single hop bed and/or multistage bed; In above-mentioned all reactors, logistics flows to as upflowing or downflow system.
In technique scheme, preferably technical scheme, the second catalyst reactor bed is at least a single hop bed and a multistage bed; Wherein, in above-mentioned all reactors, logistics flows to as upflowing.
In technique scheme, preferably, the propylene in raw material II is fresh propylene, the Propylene recovery of follow-up system or its mixture.
In technique scheme, preferably, the hydrogen peroxide ethylbenzene in raw material I is obtained by ethylbenzene oxidation, is the mixture of ethylbenzene, hydrogen peroxide ethylbenzene, and wherein, the concentration of hydrogen peroxide ethylbenzene is 5 ~ 65wt%.
In technique scheme, preferably, solvent is liquid under temperature of reaction and pressure, and does not react with reactant and product.
In technique scheme, when raw material I is the mixture of hydrogen peroxide ethylbenzene and ethylbenzene, do not add solvent; Wherein ethylbenzene is the raw material producing hydrogen peroxide ethylbenzene.
In technique scheme, preferably, epoxidation reaction temperature is 30 ~ 130 DEG C, and pressure is 1.5 ~ 6.0MPa, total mol ratio of propylene and hydrogen peroxide ethylbenzene is 2 ~ 15.
Epoxidation reaction temperature is generally 15 ~ 160 DEG C, considers economic utilization and the reaction preference of speed of reaction and catalyzer, preferably 30 ~ 130 DEG C.When the temperature is too low, speed of reaction is too low, and the amount therefore obtaining required reacting weight and required catalyzer 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 ~ 12.0MPa, is preferably 1.5 ~ 6.0MPa.
The mol ratio propylene of propylene/hydrogen peroxide ethylbenzene and the total mol ratio of hydrogen peroxide ethylbenzene that are supplied to epoxidation step are generally 1 ~ 20, and preferably 2 ~ 15, most preferably 3 ~ 12.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.
Method advantage provided by the invention is:
1, the method for epoxidation reaction product section is adopted, improve the propylene ratio of beds, can partly or entirely absorption reaction heat, reduce the reaction temperature rising of beds, ensure that epoxidation reaction is carried out under the temperature of reaction condition of the best, thus improve the selectivity of object product propene oxide.
2, the mol ratio of low propylene and hydrogen peroxide ethylbenzene can more be adapted to.By the recycle ratio of adjustment ring oxidation reaction product, the propylene circulation ratio of separation and recovery system can be reduced, reach the object reducing energy consumption, reduce investment.
3, 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.
Owing to adopting the fixed bed reaction technique of epoxidation reaction product section circulation in the present invention, improve the propylene of beds and the ratio of hydrogen phosphide cumene, can partly or entirely absorption reaction heat, reduce reaction temperature rising, ensure that epoxidation reaction is carried out under the reaction conditions of the best, the selectivity of object product propene oxide can be improved.Prove to adopt technical scheme of the present invention through test, epoxidised reaction temperature rising is only 12.4 DEG C, lower than 32.1 in comparative example DEG C, under total propylene and hydrogen peroxide ethylbenzene mol ratio are the condition of 16.75, the mol ratio of beds is up to 27.2, hydrogen peroxide ethylbenzene almost all transforms, and the selectivity of object product propene oxide reaches 99.0%, achieves good technique effect.
Accompanying drawing explanation
Fig. 1 is the method process schematic representation of hydrogen peroxide ethylbenzene of the present invention and epoxidation of propylene.
In Fig. 1,1 is the raw material I containing hydrogen peroxide ethyl benzene mixtures, 2 for containing propylene and circulation propylene feedstocks II, 3 for containing the extraction logistics of the peroxidation reaction product of propylene oxide, 4 is the recycle stream of peroxidation reaction product, 1a is epoxidation reactor, and 2a is the beds of reactor, and 3a is reactor inlet water cooler.
Below by embodiment, the present invention is further elaborated.
Embodiment
[embodiment 1]
By the technical scheme of the method for hydrogen peroxide ethylbenzene of the present invention and epoxidation of propylene, by the raw material I of the hydrogen peroxide ethyl benzene mixtures containing 19.4% weight concentration, flow is 162367.5 kgs/hr, in raw material II, and propylene 10987.6 kgs/hr, circulation propylene 155795.5 kgs/hr, mix with the Cyclic Rings oxidation reaction product of 219433.8 kgs/hr, temperature of reaction 76 DEG C, under the condition of reaction pressure 2.9MPa, enter single bed catalyst insulation fix bed reactor, with Ti/SiO
2catalyst exposure, liquid phase epoxidation reaction generates propylene oxide and xylyl alcohol and other by product.Hydrogen peroxide ethylbenzene weight air speed 4.1hr
-1the mol ratio of total propylene and hydrogen peroxide ethylbenzene is 16.75, and the propylene of beds entrance and the mol ratio of hydrogen peroxide ethylbenzene are 27.2, and reactor outlet temperature is 88.4 DEG C, the total conversion rate of hydrogen peroxide ethylbenzene is 99.2%, and the molar selectivity of propylene oxide is 99.0.
[embodiment 2]
With the technical scheme of [embodiment 1], only change the flow of circulation propylene: circulation propylene flow is 103863.5 kgs/hr, other processing condition are with [embodiment 1].Hydrogen peroxide ethylbenzene weight air speed 4.1hr
-1the mol ratio of total propylene and hydrogen peroxide ethylbenzene is 11.52, and the propylene of beds entrance and the mol ratio of hydrogen peroxide ethylbenzene are 18.47, and reactor outlet temperature out is 89.8 DEG C, the total conversion rate of hydrogen peroxide ethylbenzene is 99.2%, and the molar selectivity of propylene oxide is 98.9.
[embodiment 3]
With the technical scheme of [embodiment 1], an altering reactor form: two sections of bed catalyst insulation fix bed reactors, other processing condition are with [embodiment 1].Hydrogen peroxide ethylbenzene weight air speed 4.1hr
-1the mol ratio of total propylene and hydrogen peroxide ethylbenzene is 16.75, and the propylene of beds entrance and the mol ratio of hydrogen peroxide ethylbenzene are 27.2, and reactor outlet temperature is 88.4 DEG C, the total conversion rate of hydrogen peroxide ethylbenzene is 99.3%, and the molar selectivity of propylene oxide is 99.0.
[embodiment 4]
With the technical scheme of [embodiment 1], altering reactor temperature in: reactor inlet temperature is 80 DEG C, other processing condition are with [embodiment 1].Hydrogen peroxide ethylbenzene weight air speed 4.1hr
-1the mol ratio of total propylene and hydrogen peroxide ethylbenzene is 16.75, and the propylene of beds entrance and the mol ratio of hydrogen peroxide ethylbenzene are 27.2, and reactor outlet temperature is 92.4 DEG C, the total conversion rate of hydrogen peroxide ethylbenzene is 99.2%, and the molar selectivity of propylene oxide is 98.9.
[comparative example]
Epoxidation reactor is single stage adiabatic fixed-bed reactor, and epoxidation reaction product does not circulate.Raw material is containing the hydrogen peroxide ethyl benzene mixtures of 19.4% weight concentration, flow is 162367.5 kgs/hr, mixes with raw material propylene 10987.6 kgs/hr, circulation propylene 155795.5 kgs/hr, entrance temperature of reaction 76 DEG C, under the condition of reaction pressure 2.9MPaG, with Ti/SiO
2catalyst exposure, liquid phase epoxidation reaction generates propylene oxide and xylyl alcohol and other by product, hydrogen peroxide ethylbenzene weight air speed 4.1hr
-1, the mol ratio of total propylene and hydrogen peroxide ethylbenzene is 16.75, and the temperature out of reactor is 108.1 DEG C, and the total conversion rate of hydrogen peroxide ethylbenzene is 99.2%, and the molar selectivity of propylene oxide is 98.3%.
Claims (10)
1. the method for a hydrogen peroxide ethylbenzene and epoxidation of propylene, it is characterized in that the raw material I containing hydrogen peroxide ethylbenzene and the raw material II containing propylene, after mixing, enter reactor, it is 15 ~ 160 DEG C in epoxidation reaction temperature, pressure is 1.0 ~ 12.0MPa, total mol ratio of propylene and hydrogen peroxide ethylbenzene is under the condition of 1 ~ 20, raw material I, raw material II contacts with Ti-SiO 2 catalyst, carry out epoxidation reaction and generate propylene oxide, epoxidation reaction product wherein containing propylene oxide is divided into extraction logistics and recycle stream, wherein recycle stream is circulated to reactor inlet.
2. the method for hydrogen peroxide ethylbenzene and epoxidation of propylene 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 peroxide ethylbenzene and epoxidation of propylene 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 peroxide ethylbenzene and epoxidation of propylene according to claim 1, it is characterized in that reactor is divided into two types: the first reactor: be single reactor, wherein, the first catalyst reactor bed is single hop bed or multistage bed; The second reactor: be made up of at least two reactors in series, the catalyst reactor bed of wherein connecting is single hop bed and/or multistage bed; Wherein, in above-mentioned all reactors, logistics flows to as upflowing or downflow system.
5. the method for hydrogen peroxide ethylbenzene and epoxidation of propylene according to claim 4, it is characterized in that in the second reactor, beds is at least a single hop bed and a multistage bed; Wherein, in above-mentioned the second reactor, logistics flows to as upflowing.
6. the method for hydrogen peroxide ethylbenzene and epoxidation of propylene according to claim 1, the propylene that it is characterized in that in raw material II is fresh propylene, the Propylene recovery of follow-up system or its mixture.
7. the method for hydrogen peroxide ethylbenzene and epoxidation of propylene according to claim 1, it is characterized in that raw material I is the mixture of ethylbenzene, hydrogen peroxide ethylbenzene, wherein, the concentration of hydrogen peroxide ethylbenzene is 5 ~ 65wt%.
8. the method for hydrogen peroxide ethylbenzene and epoxidation of propylene according to claim 1, is characterized in that described solvent is liquid under temperature of reaction and pressure.
9. the method for hydrogen peroxide ethylbenzene and epoxidation of propylene according to claim 1, when it is characterized in that raw material I is the mixture of hydrogen peroxide ethylbenzene and ethylbenzene, does not add solvent; Wherein ethylbenzene is the raw material producing hydrogen peroxide ethylbenzene.
10. the method for hydrogen peroxide ethylbenzene and epoxidation of propylene according to claim 1, it is characterized in that, epoxidation reaction temperature is 30 ~ 130 DEG C, and pressure is 1.5 ~ 6.0MPa, total mol ratio of propylene and hydrogen peroxide ethylbenzene is 2 ~ 15.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111499597A (en) * | 2020-04-30 | 2020-08-07 | 常州瑞华化工工程技术股份有限公司 | Start-up and stop method of propylene oxide reaction system |
| CN112500371A (en) * | 2019-09-14 | 2021-03-16 | 南京延长反应技术研究院有限公司 | Etherification-free system and process for preparing propylene oxide by virtue of intensified propylene epoxidation |
| CN115385874A (en) * | 2021-09-26 | 2022-11-25 | 华东理工大学 | Reaction process for preparing epoxypropane by propylene gas-phase direct epoxidation method |
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| CN1418200A (en) * | 2000-03-24 | 2003-05-14 | 住友化学工业株式会社 | Process for producing oxirane compound |
| CN1835939A (en) * | 2003-08-19 | 2006-09-20 | 国际壳牌研究有限公司 | Process for the preparation of alkylene oxide |
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2014
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1418200A (en) * | 2000-03-24 | 2003-05-14 | 住友化学工业株式会社 | Process for producing oxirane compound |
| CN1835939A (en) * | 2003-08-19 | 2006-09-20 | 国际壳牌研究有限公司 | Process for the preparation of alkylene oxide |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112500371A (en) * | 2019-09-14 | 2021-03-16 | 南京延长反应技术研究院有限公司 | Etherification-free system and process for preparing propylene oxide by virtue of intensified propylene epoxidation |
| CN112500371B (en) * | 2019-09-14 | 2023-04-11 | 南京延长反应技术研究院有限公司 | Etherification-free system and process for preparing propylene oxide by virtue of intensified propylene epoxidation |
| CN111499597A (en) * | 2020-04-30 | 2020-08-07 | 常州瑞华化工工程技术股份有限公司 | Start-up and stop method of propylene oxide reaction system |
| CN111499597B (en) * | 2020-04-30 | 2023-03-10 | 常州瑞华化工工程技术股份有限公司 | Start-up and stop method of propylene oxide reaction system |
| CN115385874A (en) * | 2021-09-26 | 2022-11-25 | 华东理工大学 | Reaction process for preparing epoxypropane by propylene gas-phase direct epoxidation method |
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