CN104230855A - Cumyl hydroperoxide and propylene epoxidation method - Google Patents
Cumyl hydroperoxide and propylene epoxidation method Download PDFInfo
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- CN104230855A CN104230855A CN201310236989.1A CN201310236989A CN104230855A CN 104230855 A CN104230855 A CN 104230855A CN 201310236989 A CN201310236989 A CN 201310236989A CN 104230855 A CN104230855 A CN 104230855A
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- propylene
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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
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- 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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Abstract
The invention relates to a cumyl hydroperoxide and propylene epoxidation method, which mainly solves the problems of high reaction temperature and high molar ratio of propylene and cumyl hydroperoxide to keep high reaction efficiency in the prior art. The method is as below: introducing the materials of cumyl hydroperoxide and liquid phase propylene into a reaction zone, and contacting the materials with a Ti-silica catalyst to conduct an epoxidation reaction under the conditions of epoxidation reaction temperature of 15-160 DEG C, pressure of 1.0-12.0 MPa and molar ratio of propylene and cumyl hydroperoxide of 2-30, so as to generate epoxypropane, wherein part of the epoxidation reaction products containing epoxypropane recycles to a reaction zone entrance. The technical scheme can well solve the above problems, and can be used in industrial production of epoxypropane from epoxidation of cumyl hydroperoxide and the propylene.
Description
Technical field
The present invention relates to a kind of method of hydrogen phosphide cumene 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 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 there is the higher and problem for keeping higher reaction efficiency to need the mol ratio of higher propylene and hydrogen phosphide cumene of reaction temperature rising in prior art, a kind of method of new hydrogen phosphide cumene and epoxidation of propylene is provided, the method is 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, have the advantages that propylene oxide selectivity is high.
For solving 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 epoxidation of propylene, raw material hydrogen peroxide isopropyl benzene and propylene liquid phase enter reaction zone, 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 epoxidation reaction product section containing propylene oxide is circulated to 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 reaction zone is a reactor be made up of multistage bed, or the multistage reaction zone of single or multiple single hop reactors in series composition, or the multistage reaction zone that at least one single hop reactor is composed in series with at least one multistage bed reactor
In technique scheme, preferably, it can be upflowing that the logistics in reaction zone flows to, and also can be downflow system.More preferably, it is upflowing that the logistics in reaction zone flows to.
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, 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.
In the inventive method, 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 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.
In the inventive method, pressure can be enough to keep reaction mixture to be in the pressure of liquid state, is generally 1.0 ~ 12.0MPa, preferably 1.5 ~ 6.0MPa.
In the inventive method, total mol ratio of the propylene and hydrogen phosphide cumene that are supplied to 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 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 30.8 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 16.3, hydrogen phosphide cumene almost all transforms, and the selectivity of object product propene oxide reaches 96.2%, achieves good technique effect.
Accompanying drawing explanation
Fig. 1 is the method schematic diagram of hydrogen phosphide cumene of the present invention and epoxidation of propylene.
In Fig. 1,1 is raw material hydrogen peroxide cumene mixture, and 2 is raw material propylene and circulation propylene, 3 is the peroxidation reaction product containing propylene oxide, and 4 is the recycle stream of peroxidation reaction product, and 1a is epoxidation reactor, 2a is beds, and 3a is reactor inlet water cooler.
The inventive method advantage is:
1, epoxidation reaction product section circulation technology 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, low propylene and the mol ratio of hydrogen phosphide cumene 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.
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, raw material propylene 10812.7 kgs/hr, circulation propylene 92993.1 kgs/hr, mixes with the Cyclic Rings oxidation reaction product of 136648.1 kgs/hr, temperature of reaction 55 DEG C, single bed insulation fix bed reactor is entered, with Ti/SiO under the condition of reaction pressure 3.1MPaG
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 beds entrance and the mol ratio of hydrogen phosphide cumene then reach 16.3, reactor outlet temperature is 85.8 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.4%, and the molar selectivity of propylene oxide is 96.2%.
[embodiment 2]
With [embodiment 1], only change the flow of circulation propylene: circulation propylene flow is 61995.4 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 beds entrance and the mol ratio of hydrogen phosphide cumene then reach 11.2, reactor outlet temperature is 89.2 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.4%, and the molar selectivity of propylene oxide is 96.0%.
[embodiment 3]
With [embodiment 1], an altering reactor form: two bed insulation fix bed reactors, 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 beds entrance and the mol ratio of hydrogen phosphide cumene then reach 16.3, reactor outlet temperature is 85.8 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.4%, and the molar selectivity of propylene oxide is 96.2%.
[embodiment 4]
With [embodiment 1], an altering reactor temperature in: reactor inlet temperature 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 beds entrance and the mol ratio of hydrogen phosphide cumene then reach 16.3, reactor outlet temperature is 88.8 DEG C, the total conversion rate of hydrogen phosphide cumene is 99.5%, and the molar selectivity of propylene oxide is 96.1%.
[comparative example]
Epoxidation reactor is single stage adiabatic fixed-bed reactor, and epoxidation reaction product does not circulate.Raw material is containing the hydrogen phosphide cumene mixture of 35 % by weight concentration, flow is 101166.1 kgs/hr, mixes 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 epoxidation of propylene, raw material hydrogen peroxide isopropyl benzene and propylene liquid phase enter reaction zone, 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 epoxidation reaction product section containing propylene oxide is circulated to reaction zone entrance.
2. the method for hydrogen phosphide cumene 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 phosphide cumene 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 phosphide cumene and epoxidation of propylene according to claim 1, it is characterized in that described reaction zone is a reactor be made up of multistage bed, or the multistage reaction zone of single or multiple single hop reactors in series composition, or the multistage reaction zone that at least one single hop reactor is composed in series with at least one multistage bed reactor; It can be upflowing that logistics in reaction zone flows to, and also can be downflow system.
5. the method for hydrogen phosphide cumene and epoxidation of propylene according to claim 4, it is upflowing that the logistics that it is characterized in that in described reaction zone flows to.
6. the method for hydrogen phosphide cumene and epoxidation of propylene according to claim 1, is characterized in that raw material propylene is fresh propylene, the Propylene recovery of follow-up system or its mixture.
7. the method for hydrogen phosphide cumene and epoxidation of propylene according to claim 1, it is characterized in that 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.
8. the method for hydrogen phosphide cumene and epoxidation of propylene according to claim 1, it is characterized in that described epoxidation reaction is carried out in the liquid phase using solvent, be liquid under the temperature and pressure of described solvent when reacting, and substantially do not react with reactant and product.
9. the method for hydrogen phosphide cumene and epoxidation of propylene according to claim 8, is characterized in that, when hydrogen phosphide cumene is containing mixture as the isopropyl benzene of its raw material, this mixture to be used when not adding solvent to replace solvent.
10. the method for hydrogen phosphide cumene and epoxidation of propylene according to claim 1, it is characterized in that epoxidation reaction temperature is 30 ~ 130 DEG C, pressure is total mol ratio of 1.5 ~ 6.0MPa, propylene and hydrogen phosphide cumene is 4 ~ 20.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113083158A (en) * | 2021-03-25 | 2021-07-09 | 浙江智英石化技术有限公司 | Preparation device and preparation method of epoxypropane |
| CN114426548A (en) * | 2020-09-29 | 2022-05-03 | 中国石油化工股份有限公司 | Preparation method and system of dicyclopentadiene dioxide |
| CN116063199A (en) * | 2022-12-09 | 2023-05-05 | 万华化学集团股份有限公司 | Polymerization inhibitor and preparation method thereof, and method for co-producing benzyl alcohol and alkylene oxide |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114426548A (en) * | 2020-09-29 | 2022-05-03 | 中国石油化工股份有限公司 | Preparation method and system of dicyclopentadiene dioxide |
| CN114426548B (en) * | 2020-09-29 | 2024-04-05 | 中国石油化工股份有限公司 | Preparation method and system of dicyclopentadiene dioxide |
| CN113083158A (en) * | 2021-03-25 | 2021-07-09 | 浙江智英石化技术有限公司 | Preparation device and preparation method of epoxypropane |
| CN116063199A (en) * | 2022-12-09 | 2023-05-05 | 万华化学集团股份有限公司 | Polymerization inhibitor and preparation method thereof, and method for co-producing benzyl alcohol and alkylene oxide |
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