CN105272941B - The production method of propylene oxide - Google Patents
The production method of propylene oxide Download PDFInfo
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- CN105272941B CN105272941B CN201410354628.1A CN201410354628A CN105272941B CN 105272941 B CN105272941 B CN 105272941B CN 201410354628 A CN201410354628 A CN 201410354628A CN 105272941 B CN105272941 B CN 105272941B
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Abstract
The present invention relates to a kind of production method of propylene oxide, mainly solves the problems, such as that there are high energy consumption for the prior art.The present invention is by using comprising the following steps：A) cumyl hydroperoxide and propylene react generation liquid phase stream in the reactor；B) liquid phase stream enters high pressure propylene recovery tower, and tower top obtains the first light component stream, and tower reactor obtains the first heavy constituent logistics；B) the first heavy constituent logistics enters low pressure propylene recovery tower, and tower top obtains the second light component stream, and tower reactor obtains the second heavy constituent logistics；C) second light component stream is divided into two parts, and a part of logistics therein enters depropanizing tower, and tower top obtains the 3rd light component stream, and tower reactor obtains triple component streams；D) technical solution for being recycled back to reactor into the shunting part of depropanizing tower and the 3rd light component stream is removed in the first light component stream, the second light component stream and preferably solves the problems, such as this, available in the industrial production of propylene oxide.
Description
Technical field
The present invention relates to a kind of production method of propylene oxide.
Background technology
Propylene oxide (PO) is very important Organic Chemicals, be in acryloyl derivative yield be only second to polypropylene and
The third-largest Organic chemical products of acrylonitrile, mainly for the production of polyethers, propane diols, isopropanolamine, non-polyether polyalcohol etc., into
And unsaturated polyester resin, polyurethane, surfactant, fire retardant etc. are produced, it is widely used in chemical industry, light industry, medicine, food
The industries such as product, weaving, have far-reaching influence to chemical industry and the national economic development.With propylene oxide purposes expansion and
The growth of downstream product dosage, makes the demand in propylene oxide market increasing.
At present the method for industrial production propylene oxide mainly have chlorohydrination, have joint product conjugated oxidation (PO/SM methods and
PO/MTBE methods or PO/TBA methods) and cumyl hydroperoxide method (CHP methods) without joint product.Chlorohydrination is due in production process
It is middle to produce substantial amounts of chlorine-contained wastewater, environmental pollution and serious corrosion of equipment；The conjugated oxidation for having joint product overcomes chlorohydrination
The shortcomings of pollution and corrosion, but long flow path, investment is big, co-product is more, and joint product market have impact on epoxy third to a certain extent
The production of alkane.CHP methods are due to polluting developing direction that is small and having become Producing Process of Propylene Oxide without joint product generation.
Propylene oxide chemical combination is prepared by cumyl hydroperoxide (CHP) and propylene in the presence of fixed-bed catalytic oxidant layer
Thing, mainly includes three reaction process：(1) air-oxidation cumyl hydroperoxide；(2) CHP and propylene are in multiphase
Epoxidation reaction production propylene oxide (PO) and alpha, alpha-dimethyl benzyl alcohol (DMBA) occur in the presence of catalyst；(3) DMBA and H2
Hydrogenolysis generation isopropylbenzene occurs in the presence of a catalyst, isopropylbenzene is recycled to oxidation operation production CHP.To improve CHP's
Conversion ratio, usually makes propylene excessive, if the molar ratio of n (propylene)/n (CHP) is 5~20, therefore has largely mistake in reaction product
The propylene of amount, to improve epoxidation efficiency and reducing the refined load of PO, it is desirable to which the propylene in reaction product is carried out circulation profit
With, and the higher purity of propylene needs is circulated, necessary impurity is removed, while avoid inert component from being accumulated in the circulatory system.
Document CN1505616A discloses a kind of preparation method of propylene oxide, including propylene is existed with cumene hydroperoxide
The step of reaction obtains propylene oxide in the presence of catalyst, and the reaction mixture for obtaining above-mentioned reactions steps are distilled simultaneously
The step of propylene unreacted from distillation recovered overhead, the bottom temperature of wherein destilling tower is set to 200 DEG C or lower.This method
In, tower reactor goes out thick PO products, and tower top goes out propylene.Since PO has thermal sensitivity, general industry production control bottom temperature is not higher than
130 DEG C, that is, define the operating pressure of rectifying column, cause tower top operation temperature to be less than less than 40 DEG C, the cold of routine can not be used
But water does cryogen, and the cryogen of a large amount of lower temperatures need to be used to carry out the condensation recycling of propylene, causes the difficulty of industrial operation, energy consumption
It is high.
The content of the invention
The technical problems to be solved by the invention are that there are the problem of high energy consumption for the prior art, there is provided a kind of new epoxy third
The production method of alkane.This method has energy consumption low, and propylene recovery rate is high, and propane removing is thorough, product propylene high income, if
The characteristics of standby reduced investment, flow is simple, and industrializing implementation is strong.
In order to solve the above technical problems, the technical solution that the present invention takes is as follows：A kind of production method of propylene oxide, bag
Include following steps：
A) raw material hydrogen peroxide isopropylbenzene and propylene react in the reactor generation containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene,
The liquid phase stream of propylene oxide, propylene and propane；
B) it is described to enter high pressure propylene containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene, propylene oxide, propylene and propane liquid phase stream
Recovery tower, after separation, tower top obtains the first light component stream, and tower reactor obtains containing α, alpha-alpha-dimethyl benzylalcohol, isopropylbenzene, epoxy third
First heavy constituent logistics of alkane, a small amount of propylene and propane；
B) the first heavy constituent logistics enters low pressure propylene recovery tower, and after separation, tower top obtains the second light component stream,
Tower reactor obtains the second heavy constituent logistics containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene and propylene oxide and discharges it；
C) second light component stream is divided into two parts, and a part of logistics therein enters depropanizing tower, after separation, tower
Top obtains the 3rd light component stream, and tower reactor obtains triple component streams containing propane and discharges it；
D) the shunting part and the 3rd into depropanizing tower is removed in the first light component stream, the second light component stream
Light component stream is recycled back to reactor；
Wherein, the operating pressure of the high pressure propylene recovery tower is calculated as 0.5~3.5MPa with gauge pressure, and the low pressure propylene returns
The operating pressure for receiving tower is calculated as 0.1~0.4MPa with gauge pressure.
In above-mentioned technical proposal, it is preferable that the raw material hydrogen peroxide isopropylbenzene is obtained by cumene oxidation, is
The mixture of hydrogen oxide isopropylbenzene and isopropylbenzene；In the mixture, the weight percent concentration of cumyl hydroperoxide is 20
~80%.
In above-mentioned technical proposal, it is preferable that described to contain α, alpha-alpha-dimethyl benzylalcohol, isopropylbenzene, propylene oxide, propylene and propane
Liquid phase stream in, by weight percentage, α, the content of alpha-alpha-dimethyl benzylalcohol is 19~50%, the content of isopropylbenzene for 10~
70%, the content of propylene oxide is 5~20%, and the content of propylene is 5~60%, and the content of propane is 0~10%.
In above-mentioned technical proposal, it is preferable that the operating pressure of the high pressure propylene recovery tower is calculated as 1.5 with gauge pressure~
2.5MPa, the operating pressure of the low pressure propylene recovery tower are calculated as 0.15~0.25MPa with gauge pressure.
In above-mentioned technical proposal, it is preferable that the high pressure propylene recovery column overhead operation temperature is 5~80 DEG C, tower reactor behaviour
Make temperature as 45~120 DEG C, theoretical cam curve is 10~50.
In above-mentioned technical proposal, it is preferable that the low pressure propylene recovery column overhead operation temperature is -30~-8 DEG C, tower reactor
Operation temperature is 85~120 DEG C, and theoretical cam curve is 10~50.
In above-mentioned technical proposal, it is preferable that depropanizing tower operating pressure is calculated as 1.5~2.5MPa, tower top operation with gauge pressure
Temperature is 40~65 DEG C, and tower reactor operation temperature is 40~65 DEG C, and theoretical cam curve is 10~80.
In above-mentioned technical proposal, it is preferable that into the shunting part of depropanizing tower and institute in second light component stream
The weight ratio for stating the second light component stream is 1:(1~10).
In the method for the present invention, the epoxidation reaction of cumyl hydroperoxide and propylene is to be known in the art.Generally
Ground, reaction temperature are 40~120 DEG C, and reaction pressure is 3.5~6.8MPa, and propylene/CHP molar ratios are for 5~20, CHP air speeds
0.2~1.2 it is small when -1.Catalyst used can be the SiO 2 molecular sieve catalyst of titaniferous.
Propylene recovery in the method for the present invention is using the tower of propylene recovery containing high pressure, low pressure propylene recovery tower and depropanizing tower
Propylene recovery process for refining, liquid phase epoxidation propane reaction product initially enter high pressure propylene recovery tower and are refined, epoxidation production
For the propylene of 60~95 weight % from recovered overhead, tower reactor obtains the crude propene oxide product containing a small amount of propylene in thing.Containing a small amount of third
The crude propene oxide product of alkene is sent into low pressure propylene recovery tower and continues to refine, recovered overhead propylene, and tower reactor obtains being free of third
The crude propene oxide product of alkene.By high pressure propylene recovery tower and low pressure propylene recovery tower, the third of 99~100 weight % in raw material
Alkene is recycled.Low pressure propylene recovery column overhead stream divides two parts, and a part becomes Propylene recovery, and another part is sent into de- third
Alkane tower, to remove the propane impurity that fresh propylene brings recycle system of reaction into, the propane that depropanizing tower tower reactor is removed, through height
Still unsegregated propylene is pressed after propylene recovery tower and low pressure propylene recovery tower from depropanizing tower removed overhead.Using present invention side
Method, epoxidation product are separated in high pressure propylene recovery tower first so that most of propylene is from removed overhead, so as to reduce
The inlet amount of low pressure propylene recovery tower.Therefore, high pressure propylene recovery column overhead takes conventional cooling water to make cryogen and carries out third
The condensation recycling of alkene, only low pressure propylene recovery column overhead need to use the cryogen of lower temperature.Compared with prior art, may be used
Reduce energy consumption 60%.In addition, using the method for the present invention, propylene and unreacted in cumyl hydroperoxide epoxidation reaction ensure that
The separation of complete propylene and product propylene, and the inert component propane for bringing system in raw material propylene into is stripped of, return
The propylene of receipts is recycled back to propylene ring oxidation reaction system and does reaction raw materials, both ensure that the yield (up to 99.9%) of propylene, together
When ensure that the purity requirement (up to 95%) of circulation propylene and the yield (reachable 99.9%) of PO products, flow is simple, equipment
Reduced investment, achieves preferable technique effect.
Brief description of the drawings
Fig. 1 is the process flow diagram of the method for the present invention.
In Fig. 1, I is reactor, and II is high pressure propylene recovery tower, and III is low pressure propylene recovery tower, and IV is depropanizing tower, 1
It is fresh propylene for raw material hydrogen peroxide isopropylbenzene, 2,3 be containing α, alpha-alpha-dimethyl benzylalcohol, isopropylbenzene, propylene oxide, propylene and third
The liquid phase stream of alkane, 4 be high pressure propylene recovery column overhead stream (the first light component stream), and 5 be high pressure propylene recovery tower tower reactor
Logistics (the first heavy constituent logistics), 6 be low pressure propylene recovery column overhead stream (the second light component stream), and 7 return for low pressure propylene
The shunting fraction of stream for removing depropanizing tower in column overhead stream on a small quantity is received, 8 be crude propene oxide product (the second heavy constituent logistics),
9 be depropanizing tower overhead stream (the 3rd light component stream), and 10 be propane (triple component streams).
In Fig. 1, raw material hydrogen peroxide isopropylbenzene 1 and fresh propylene 2 react generation containing propylene oxide, third in reactor I
The liquid phase stream 3 of alkene and propane.Logistics 3 is sent into high pressure propylene recovery tower II and is separated, and tower top obtains logistics 4, and tower reactor obtains
Logistics 5 containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene, propylene oxide, a small amount of propylene and propane.Low pressure propylene recovery is sent into logistics 5
Tower III separates, and tower top obtains logistics 6, and the crude propene oxide product stream 8 that tower reactor obtains removing propylene (contains α, alpha-alpha-dimethyl benzyl
Alcohol, isopropylbenzene and propylene oxide).The propylene stream 6 of III recovered overhead of low pressure propylene recovery tower divides two parts, a part therein
Logistics 7 enters depropanizing tower IV, and after separation, tower top obtains logistics 9, and tower reactor obtains propylene oxide stream 10.High pressure propylene recovery tower tower
Push up and removed in logistics 4, low pressure propylene recovery column overhead stream 6 into the part of depropanizing tower and depropanizing tower overhead stream 9
It is recycled back to reactor and participates in reaction.Wherein, the overhead condenser of each tower, which all omits, does not draw.
Below by embodiment, the invention will be further elaborated, but is not limited only to the present embodiment.
Embodiment
【Embodiment 1】
As shown in Figure 1, by taking 100,000 tons/year of PO devices as an example, raw material hydrogen peroxide isopropylbenzene 1 and fresh propylene 2 are anti-
Answer liquid phase stream 3 of the reaction generation containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene, propylene oxide, propylene and propane in device I.Logistics 3 is sent
Enter high pressure propylene recovery tower II to be separated, tower top obtains logistics 4, and tower reactor obtains containing α, alpha-alpha-dimethyl benzylalcohol, isopropylbenzene, epoxy
The logistics 5 of propane, a small amount of propylene and propane.Logistics 5 is sent into low pressure propylene recovery tower III and is separated, and tower top obtains logistics 6, and tower reactor obtains
To the crude propene oxide product stream 8 of removing propylene.The propylene stream 6 of III recovered overhead of low pressure propylene recovery tower divides two parts,
A part of logistics 7 therein enters depropanizing tower IV, and after separation, tower top obtains logistics 9, and tower reactor obtains propylene oxide stream 10.High pressure
Removed in propylene recovery column overhead stream 4, low pressure propylene recovery column overhead stream 6 into the part of depropanizing tower and de- third
Alkane column overhead stream 9 is recycled back to reactor and participates in reaction.
Wherein, in liquid phase stream 3, by weight percentage, α, the content of alpha-alpha-dimethyl benzylalcohol is 26%, and isopropylbenzene contains
Measure as 6%, the content of propylene oxide is 10%, and the content of propylene is 55%, and the content of propane is 3%..
The operating condition of high pressure propylene recovery tower is：Operating pressure is 1.6MPa, and tower top operation temperature is 40 DEG C, tower reactor behaviour
Make temperature as 72 DEG C, theoretical cam curve is 25 pieces.
The operating condition of low pressure propylene recovery tower is：Operating pressure is 0.3MPa, and tower top operation temperature is -12 DEG C, tower reactor
Operation temperature is 120 DEG C, and theoretical cam curve is 20 pieces.
The operating condition of depropanizing tower is：Operating pressure is 2.0MPa, and tower top operation temperature is 51 DEG C, tower reactor operation temperature
For 60 DEG C, theoretical cam curve is 50 pieces.
The weight ratio of logistics 7 and low pressure propylene recovery column overhead stream 6 into depropanizing tower is 1:2.4.
As a result it is：575 tons of the cooling water that high pressure propylene recovery column overhead takes temperature to be 32 DEG C makees cryogen and carries out propylene
Condensation recycling, low pressure propylene recovery column overhead use temperature as -20 DEG C of 29.3 ton hour of cryogen.
The yield of propylene is 99.9%, and the yield for 95%, PO products of Propylene recovery purity is 99.9%.Its mesohigh
Propylene recovery column overhead propylene recovery rate is 70%.
【Embodiment 2】
Together【Embodiment 1】, simply operating condition change.
In liquid phase stream 3, by weight percentage, α, the content of alpha-alpha-dimethyl benzylalcohol is 26%, and the content of isopropylbenzene is
21.5%, the content of propylene oxide is 10.5%, and the content of propylene is 39%, and the content of propane is 2%.High pressure propylene recovery tower
Operating condition be：Operating pressure is 1.6MPa, and tower top operation temperature is 40 DEG C, and tower reactor operation temperature is 87 DEG C, theoretical tray
Number is 25 pieces.
The operating condition of low pressure propylene recovery tower is：Operating pressure is 0.2MPa, and tower top operation temperature is -20 DEG C, tower reactor
Operation temperature is 120 DEG C, and theoretical cam curve is 20 pieces.
The operating condition of depropanizing tower is：Operating pressure is 2.0MPa, and tower top operation temperature is 51 DEG C, tower reactor operation temperature
For 58 DEG C, theoretical cam curve is 50 pieces.
The weight ratio of logistics 7 and low pressure propylene recovery column overhead stream 6 into depropanizing tower is 1:3.
As a result it is：340 ton hour of cooling water that high pressure propylene recovery column overhead takes temperature to be 32 DEG C makees cryogen and carries out third
The condensation recycling of alkene, low pressure propylene recovery column overhead use temperature as -30 DEG C of 32 ton hour of cryogen.
The yield of propylene is 99.9%, and the yield for 95%, PO products of Propylene recovery purity is 99.9%.Its mesohigh
Propylene recovery column overhead propylene recovery rate is 60%.
【Comparative example 1】
Together【Embodiment 1】, it is that epoxidation product enters a single destilling tower, it is unreacted from distillation recovered overhead
Propylene, tower reactor go out thick PO products.
The operating condition of destilling tower is：Operating pressure is 0.3MPa, and tower top operation temperature is -12 DEG C, tower reactor operation temperature
For 120 DEG C, theoretical cam curve is 30 pieces.
As a result it is：Tower top uses temperature as -20 DEG C of 92.5 ton hour of cryogen.
Claims (6)
1. a kind of production method of propylene oxide, comprises the following steps：
A) raw material hydrogen peroxide isopropylbenzene and propylene react generation containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene, epoxy in the reactor
The liquid phase stream of propane, propylene and propane；
B) it is described to enter high pressure propylene recovery containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene, propylene oxide, propylene and propane liquid phase stream
Tower, after separation, tower top obtains the first light component stream, and tower reactor obtains containing α, alpha-alpha-dimethyl benzylalcohol, isopropylbenzene, propylene oxide, few
Measure the first heavy constituent logistics of propylene and propane；
B) the first heavy constituent logistics enters low pressure propylene recovery tower, and after separation, tower top obtains the second light component stream, tower reactor
Obtain the second heavy constituent logistics containing alpha, alpha-dimethyl benzyl alcohol, isopropylbenzene and propylene oxide and discharge it；
C) second light component stream is divided into two parts, and a part of logistics therein enters depropanizing tower, and after separation, tower top obtains
To the 3rd light component stream, tower reactor obtains triple component streams containing propane and discharges it；
D) the shunting part for entering depropanizing tower and the 3rd light group are removed in the first light component stream, the second light component stream
Point logistics is recycled back to reactor；
Wherein, the operating pressure of the high pressure propylene recovery tower is calculated as 0.5~3.5MPa, the low pressure propylene recovery tower with gauge pressure
Operating pressure 0.1~0.4MPa is calculated as with gauge pressure；
The high pressure propylene recovery column overhead operation temperature is 5~80 DEG C, and tower reactor operation temperature is 45~120 DEG C, theoretical tray
Number is 10~50；
The low pressure propylene recovery column overhead operation temperature is -30~-8 DEG C, and tower reactor operation temperature is 85~120 DEG C, theoretical tower
Plate number is 10~50.
2. the production method of propylene oxide according to claim 1, it is characterised in that the raw material hydrogen peroxide isopropylbenzene is
Obtained by cumene oxidation, be the mixture of cumyl hydroperoxide and isopropylbenzene；In the mixture, hydrogen peroxide isopropyl
The weight percent concentration of benzene is 20~80%.
3. the production method of propylene oxide according to claim 1, it is characterised in that it is described to contain α, it is alpha-alpha-dimethyl benzylalcohol, different
Propyl benzene, propylene oxide, propylene and propane liquid phase stream in, by weight percentage, α, the content of alpha-alpha-dimethyl benzylalcohol is 19
~50%, the content of isopropylbenzene is 10~70%, and the content of propylene oxide is 5~20%, and the content of propylene is 5~60%, third
The content of alkane is 0~10%.
4. the production method of propylene oxide according to claim 1, it is characterised in that the operation of the high pressure propylene recovery tower
Pressure is calculated as 1.5~2.5MPa with gauge pressure, and the operating pressure of the low pressure propylene recovery tower is calculated as 0.15 with gauge pressure~
0.25MPa。
5. the production method of propylene oxide according to claim 1, it is characterised in that depropanizing tower operating pressure is in terms of gauge pressure
For 1.5~2.5MPa, tower top operation temperature is 40~65 DEG C, and tower reactor operation temperature is 40~65 DEG C, theoretical cam curve for 10~
80。
6. the production method of propylene oxide according to claim 1, it is characterised in that enter in second light component stream
The shunting part of depropanizing tower and the weight ratio of second light component stream are 1:(1~10).
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| CN110483445B (en) * | 2019-08-28 | 2022-10-21 | 无锡智归科技有限公司 | Epoxypropane production device and dehydration process of cumene hydroperoxide and cumene in production process thereof |
| US11746033B2 (en) | 2019-12-19 | 2023-09-05 | Wanhua Chemical Group Co., Ltd. | Method for treating production wastewater from the preparation of propylene oxide by co-oxidation |
| CN113003847B (en) * | 2019-12-19 | 2023-03-03 | 万华化学集团股份有限公司 | Treatment method for wastewater generated in production of preparing epoxypropane by co-oxidation method |
| CN111470933B (en) * | 2020-04-28 | 2022-11-15 | 上海智英化工技术有限公司 | C3 separation method capable of saving energy and reducing equipment |
| CN112125870A (en) * | 2020-09-15 | 2020-12-25 | 中国石油化工股份有限公司 | CHPPO device and method for optimizing epoxidation reaction system |
| CN112110881A (en) * | 2020-09-15 | 2020-12-22 | 中国石油化工股份有限公司 | System and method for improving selectivity of reaction product of CHPPO device |
| CN114478171A (en) * | 2020-10-26 | 2022-05-13 | 中国石油化工股份有限公司 | Method and system for refining cumene |
| CN112891977A (en) * | 2021-01-22 | 2021-06-04 | 中国石油化工股份有限公司 | CHPPO double-tower rectification separation system and separation method |
| CN112898240A (en) * | 2021-01-22 | 2021-06-04 | 中国石油化工股份有限公司 | CHPPO hydrocarbon injection crude separation system and crude separation method |
| CN112898238A (en) * | 2021-01-22 | 2021-06-04 | 中国石油化工股份有限公司 | CHPPO epoxidation reaction product crude separation system and separation method |
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| CN1505616A (en) * | 2001-04-27 | 2004-06-16 | ס�ѻ�ѧ��ҵ��ʽ���� | Process for producing propylene oxide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1505616A (en) * | 2001-04-27 | 2004-06-16 | ס�ѻ�ѧ��ҵ��ʽ���� | Process for producing propylene oxide |
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