CN104557438A - Method for producing isopropyl benzene from benzene and propylene - Google Patents
Method for producing isopropyl benzene from benzene and propylene Download PDFInfo
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- CN104557438A CN104557438A CN201310512683.4A CN201310512683A CN104557438A CN 104557438 A CN104557438 A CN 104557438A CN 201310512683 A CN201310512683 A CN 201310512683A CN 104557438 A CN104557438 A CN 104557438A
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Abstract
The invention relates to a method for producing isopropyl benzene from benzene and propylene, and mainly solves the problems of high benzene/olefin ratio and low propylene conversion rate in the prior art. The method comprises the following steps: a) benzene and propylene enter a main reaction region to contact a contact, thereby generating a first stream; b) the first stream is divided into two parts, one part is circulated back to the main reaction region, and the other part enters at least one sub-reaction region; c) the stream entering the sub-reaction region contacts the catalyst to generate a second stream; and d) the second stream is divided into two parts, one part of circulated back to the sub-reaction region, and the other part enters a subsequent procedure to obtain the product isopropyl benzene. The technical scheme well solves the problems, and can be used in industrial production of isopropyl benzene from benzene and propylene.
Description
Technical field
The present invention relates to a kind of method of benzene and production of propylene isopropyl benzene.
Background technology
Isopropyl benzene is a kind of important Organic Chemicals, is the main intermediate compound producing phenol, acetone and alpha-methyl styrene.Industrially isopropyl benzene is prepared by propylene and benzene alkylation reaction, and its by product is mainly polyisopropylbenzene.Just disclose in the presence of acidic as far back as UOP in 1945, the method (SPA method) (US2382318) of isopropyl benzene is prepared with propylene and benzene reaction, SPA method take solid phosphoric acid as alkylation catalyst, because solid phosphoric acid can not catalysis transalkylation reaction, so there is no transalkylation portion in technical process.Therefore, SPA method can only be run under high benzene alkene mol ratio (5 ~ 7) condition, and the yield of its isopropyl benzene is only about 95%.Last century the eighties, Monsanto company exploitation with AlCl
3for the isopropyl benzene production technique of alkylation catalyst, and realize industrial application.Due to AlCl
3equally can not catalysis transalkylation reaction, therefore, with AlCl
3it is still lower in the yield of isopropyl benzene that method produces isopropyl benzene, also there is serious pollution problem and corrosion of equipment problem simultaneously.
In the nineties in last century, it is catalyzer that (US4992606, US5362697, US5453554, US5522984, US5672799, US6162416, US6051521) companies such as Dow, CD Tech, Mobil-Badger, Enichem and UOP disclose with micro-pore zeolite, has the fixed-bed process flow process of transalkylation ability.In the prior art, first benzene and propylene carry out alkylated reaction in alkylation reaction device, the polysubstituted isopropyl benzene that alkylated reaction generates is after distillation system is separated, and transalkylation reaction is carried out in polysubstituted isopropyl benzene enters single bed transalkylation reaction zone after mixing with benzene again.
In existing disclosed isopropyl benzene technology, the alkylation of benzene and propylene is all adopt single, multistage laminar fixed-bed reactor, and propylene sectional feeding and reaction solution outside circulation, and benzene alkene is greater than 2.0 than usually, in fact, in most running gears, benzene alkene is than being all greater than 3.0.Restriction benzene alkene is than the technology barrier reduced further: reduce benzene alkene further and compare 2.0, even lower, or cause rapid catalyst deactivation due to too high density of propylene, or cause the deficiency of propylene conversion due to too high outer circulation amount, or cause the too high of impurity n-proplbenzene in product due to too high temperature of reaction.Recently, document US6835862B1 discloses by process optimization, adopts higher reaction solution outer circulation amount can reduce the deactivation rate of catalyzer.But, adopt single reactor and higher reaction solution outer circulation than Technology, be difficult to the problem simultaneously solving above-mentioned three contradictions.
Summary of the invention
Technical problem to be solved by this invention is that prior art exists benzene alkene than high, that propylene conversion is low problem, provides a kind of method of new benzene and production of propylene isopropyl benzene.The method has benzene alkene than low, the feature that propylene conversion 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 benzene and production of propylene isopropyl benzene, comprises the following steps:
A) benzene and propylene enter main reaction region, with catalyst exposure, generate first burst of logistics;
B) first burst of logistics is divided into two portions, and a part loops back main reaction region, and another part enters at least one secondary response district;
C) enter logistics and the catalyst exposure in secondary response district, generate second burst of logistics;
D) second burst of logistics is divided into two portions, and a part loops back secondary response district, and another part enters down-stream and obtains product isopropyl benzene.
In technique scheme, preferably, described main reaction region and at least one secondary response district are all the reactors of at least one section, or by the reaction zone of at least two single hop reactors in series, or the reaction zone of at least one single hop reactor and at least one reactors in series of at least two sections.
In technique scheme, preferably, the operational condition of described main reaction region is: the mol ratio of benzene and propylene is 0.5 ~ 3.0, and propylene weight air speed is 0.1 ~ 10 hour
-1, temperature of reaction is 90 ~ 180 DEG C, and reaction pressure is 1.0 ~ 4.0MPa, and recycle ratio is 1 ~ 50.More preferably, the operational condition of described main reaction region is: the mol ratio of benzene and propylene is 1.0 ~ 3.0, and propylene weight air speed is 0.2 ~ 5.0 hour
-1, temperature of reaction is 95 ~ 150 DEG C, and reaction pressure is 2.0 ~ 3.0MPa, and recycle ratio is 2 ~ 25.
In technique scheme, preferably, the operational condition at least one secondary response district is: temperature of reaction is 80 ~ 160 DEG C, and reaction pressure is 1.0 ~ 4.0MPa, and liquid phase weight air speed is 1 ~ 100 hour
-1, recycle ratio is 0 ~ 15.More preferably, the operational condition at least one secondary response district is: temperature of reaction is 90 ~ 150 DEG C, and reaction pressure is 2.0 ~ 3.0MPa, and liquid phase weight air speed is 1 ~ 60 hour
-1, recycle ratio is 0 ~ 10.
In technique scheme, preferably, the recycle ratio of main reaction region is greater than the recycle ratio in secondary response district.
In technique scheme, preferably, described catalyzer is selected from Beta zeolite, mordenite or has the zeolite of MWW laminate structure.
In technique scheme, preferably, propylene segmentation enters main reaction region.
In technique scheme, preferably, benzene enters from the top of main reaction region, and the logistics looping back main reaction region enters from the top of main reaction region.
In technique scheme, preferably, the logistics entering at least one secondary response district enters from the top at least one secondary response district.
In the inventive method, described pressure refers to gauge pressure.Described recycle ratio is the weight ratio of recycle stream and reactor effluent stream.
The catalyzer used in the inventive method is selected from Beta zeolite, mordenite or has the zeolite of MWW laminate structure.Wherein, the zeolite having a MWW laminate structure described in can be selected from MCM-22, MCM-56, MCM-49, and according to having the zeolite of MWW structure disclosed in document CN200410066636.2 and CN200610029979.0.
In the inventive method, secondary response district also can add benzene logistics and propylene stream.
In order to solve at low benzene alkene than under condition, propylene conversion is low, impurity n-proplbenzene content is high in the easy inactivation of catalyzer and product, these three conflicting problems, the inventive method is provided with at least two reaction zones, make the effluent stream of the first reaction zone enter at least the second reaction zone and continue reaction, first reaction zone is run under higher recycle ratio condition, second reaction zone is run in lower recycle ratio or under almost not having outer circulation material existent condition, and this extends in fact total residence time.Propylene is in the first reaction zone almost complete reaction, and a small amount of unreacted propylene continues in second reaction zone reaction, thus ensure that the high conversion of propylene.Adopt the inventive method, benzene alkene ratio can be reduced to less than 2.0, and propylene conversion can be greater than 99.99%, and in product, n-proplbenzene content lower than 120 mg/kg isopropyl benzenes, can achieve good technique effect.
Accompanying drawing explanation
Fig. 1 is process flow diagram of the present invention, and to contain primary and secondary two reaction zones, each reaction zone is two beds.
Fig. 2 is the process flow diagram of prior art.
In Fig. 1 and Fig. 2,1 is main reaction region, and 2 is secondary response district, and 3 is benzene feedstock, 4 is propylene, 5 for entering the propylene of main reaction region first beds, and 6 for entering the propylene of main reaction region second beds, and 7 is main reaction region effluent stream, 8 for looping back the logistics of main reaction region, 9 for entering the logistics in secondary response district, and 10 is product stream, and 11 for looping back the logistics in secondary response district.
Below by embodiment, the present invention is further elaborated.
Embodiment
[embodiment 1]
By the technical process of Fig. 1, comprise two reactors, each reactor comprises two beds, and wherein each beds of each reactor is mounted with 20 grams of preformed catalysts containing MCM-56 zeolite.
The reaction conditions of main reactor is: every section of bed temperature of reaction 125 DEG C, reaction pressure 2.5MPa, the propylene flow entering every section of beds is 20 Grams Per Hours, and benzene flow is 135 Grams Per Hours, and benzene alkene ratio is 1.8, and propylene weight air speed is 1.0 hours
-1, circular flow is 1050 Grams Per Hours, and recycle ratio is 6.
The reaction conditions of secondary response device is: every section of bed temperature of reaction 115 DEG C, reaction pressure 2.5MPa, liquid phase air speed is 4.4 hours
-1, recycle ratio is 0.Continuous operation 15 days, reaction result: propylene conversion 99.99%, n-proplbenzene content 92mg/kg isopropyl benzene in product.
[embodiment 2]
By the technical process of Fig. 1, comprise two reactors, each reactor comprises two beds, and wherein each beds of each reactor is mounted with 10 grams of catalyzer, and catalyzer is according to method preparation disclosed in document CN200410066636.2.
The reaction conditions of main reactor is: every section of bed temperature of reaction 120 DEG C, reaction pressure 2.5MPa, the propylene flow entering every section of beds is 15 Grams Per Hours, and benzene flow is 84 Grams Per Hours, and benzene alkene ratio is 1.5, and propylene weight air speed is 1.5 hours
-1, circular flow is 798 Grams Per Hours, and recycle ratio is 7.0.
The reaction conditions of secondary response device is: every section of bed temperature of reaction 110 DEG C, reaction pressure 2.5MPa, every section of beds propylene flow is 0 Grams Per Hour, and benzene flow is 0 Grams Per Hour, and liquid phase air speed is 11 hours
-1, circular flow is 110 Grams Per Hours, and recycle ratio is 1.0.
Continuous operation 15 days, reaction result: propylene conversion 99.99%, n-proplbenzene content 87mg/kg isopropyl benzene in product.
[embodiment 3]
By the technical process of Fig. 1, comprise two reactors, just each reactor comprises three beds, and wherein each beds of each reactor is mounted with 20 grams of catalyzer, and catalyzer is according to method preparation disclosed in document CN200410066636.2.
The reaction conditions of main reactor is: every section of bed temperature of reaction 135 DEG C, reaction pressure 2.5MPa, the propylene flow entering every section of beds is 20 Grams Per Hours, and benzene flow is 220 Grams Per Hours, and benzene alkene ratio is 2.0, and propylene weight air speed is 1.0 hours
-1, circular flow is 1692 Grams Per Hours, and recycle ratio is 6.
The reaction conditions of secondary response device is: every section of bed temperature of reaction 105 DEG C, reaction pressure 2.5MPa, first paragraph beds propylene flow is 5 Grams Per Hours, and two-stage catalytic agent bed does not pass into propylene in addition, and liquid phase air speed is 4.8 hours
-1, circular flow is 340 grams hours, and recycle ratio is 1.2.。
Continuous operation 7 days, reaction result: propylene conversion 99.99%, n-proplbenzene content 50mg/kg isopropyl benzene in product.
[embodiment 4]
By the technical process of Fig. 1, comprise two reactors, just each reactor comprises a beds, and wherein each beds of each reactor is mounted with 20 grams of catalyzer, and catalyzer is according to method preparation disclosed in document CN200410066636.2.
The reaction conditions of main reactor is: catalyst bed reaction temperature 135 DEG C, reaction pressure 3.0MPa, and the propylene flow entering beds is 30 Grams Per Hours, and benzene flow is 167 Grams Per Hours, and benzene alkene ratio is 3.0, and propylene weight air speed is 1.5 hours
-1, circular flow is 2360 Grams Per Hours, and recycle ratio is 12.
The reaction conditions of secondary response device is: every section of bed temperature of reaction 110 DEG C, reaction pressure 3.0MPa, liquid phase air speed is 10 hours
-1, circular flow is 0 Grams Per Hour, and recycle ratio is 0.
Continuous operation 15 days, reaction result: propylene conversion 99.99%, n-proplbenzene content 110mg/kg isopropyl benzene in product.
[embodiment 5]
By the technical process of Fig. 1, comprise two reactors, each reactor comprises two beds, and wherein each beds of each reactor is mounted with 10 grams of preformed catalysts containing MCM-56 zeolite.
The reaction conditions of main reactor is: every section of bed temperature of reaction 110 DEG C, reaction pressure 2.5MPa, the propylene flow entering every section of beds is 30 Grams Per Hours, and benzene flow is 279 Grams Per Hours, and benzene alkene ratio is 2.5, and propylene weight air speed is 3.0 hours
-1, circular flow is 2700 Grams Per Hours, and recycle ratio is 8.0.
The reaction conditions of secondary response device is: every section of bed temperature of reaction 100 DEG C, reaction pressure 2.5MPa, liquid phase air speed is 17 hours
-1, first paragraph beds propylene flow is 0 Grams Per Hour, and the propylene flow of second segment beds is 0 Grams Per Hour, and circular flow is 0 gram hour.
Continuous operation 7 days, reaction result: propylene conversion 99.99%, n-proplbenzene content 75mg/kg isopropyl benzene in product.
[embodiment 6]
By the technical process of Fig. 1, comprise two reactors, each reactor comprises two beds, and wherein each beds of each reactor is mounted with 10 grams of catalyzer, and catalyzer is according to method preparation disclosed in document CN200610029979.0.
The reaction conditions of main reactor is: every section of bed temperature of reaction 115 DEG C, reaction pressure 2.7MPa, the propylene flow entering every section of beds is 8 Grams Per Hours, and benzene flow is 75 Grams Per Hours, and benzene alkene ratio is 2.5, and propylene weight air speed is 0.8 hour
-1, circular flow is 275 Grams Per Hours, and recycle ratio is 3.0.
The reaction conditions of secondary response device is: every section of bed temperature of reaction 120 DEG C, reaction pressure 2.7MPa, and the propylene flow entering every section of beds is 0 Grams Per Hour, benzene flow is 75 Grams Per Hours, circular flow is 91 Grams Per Hours, and recycle ratio is 0.5, and liquid phase air speed is 9.1 hours
-1.
Continuous operation 7 days, reaction result: propylene conversion 99.98%, n-proplbenzene content 97mg/kg isopropyl benzene in product.
[comparative example 1]
Adopt the technical process only having a reactor, as shown in Figure 2, reactor comprises four sections of beds, and propylene is divided into four parts to enter four beds respectively, benzene enters from reactor head, and each beds is mounted with 10 grams of preformed catalysts containing MCM-22 zeolite.
Reaction conditions is: every section of bed temperature of reaction 140 DEG C, reaction pressure 2.7MPa, and the propylene flow entering every section of beds is 15 Grams Per Hours, benzene flow is 178 Grams Per Hours, circular flow is 1428 Grams Per Hours, and benzene alkene ratio is 1.6, and propylene weight air speed is 1.5 hours
-1, recycle ratio is 6.0.
Continuous operation 15 days, reaction result: propylene conversion 99.0%, n-proplbenzene content 170mg/kg isopropyl benzene in product.
The above results illustrates, adopt prior art at low benzene alkene than under condition, the transformation efficiency of propylene is lower, and n-proplbenzene content is also higher simultaneously.
Claims (10)
1. a method for benzene and production of propylene isopropyl benzene, comprises the following steps:
A) benzene and propylene enter main reaction region, with catalyst exposure, generate first burst of logistics;
B) first burst of logistics is divided into two portions, and a part loops back main reaction region, and another part enters at least one secondary response district;
C) enter logistics and the catalyst exposure in secondary response district, generate second burst of logistics;
D) second burst of logistics is divided into two portions, and a part loops back secondary response district, and another part enters down-stream and obtains product isopropyl benzene.
2. the method for benzene and production of propylene isopropyl benzene according to claim 1, it is characterized in that described main reaction region and at least one secondary response district are all the reactors of at least one section, or by the reaction zone of at least two single hop reactors in series, or the reaction zone of at least one single hop reactor and at least one reactors in series of at least two sections.
3. the method for benzene and production of propylene isopropyl benzene according to claim 1, is characterized in that the operational condition of described main reaction region is: the mol ratio of benzene and propylene is 0.5 ~ 3.0, and propylene weight air speed is 0.1 ~ 10 hour
-1, temperature of reaction is 90 ~ 180 DEG C, and reaction pressure is 1.0 ~ 4.0MPa, and recycle ratio is 1 ~ 50.
4. the method for benzene and production of propylene isopropyl benzene according to claim 3, is characterized in that the operational condition of described main reaction region is: the mol ratio of benzene and propylene is 1.0 ~ 3.0, and propylene weight air speed is 0.2 ~ 5.0 hour
-1, temperature of reaction is 95 ~ 150 DEG C, and reaction pressure is 2.0 ~ 3.0MPa, and recycle ratio is 2 ~ 25.
5. the method for benzene and production of propylene isopropyl benzene according to claim 1, is characterized in that the operational condition at least one secondary response district is: temperature of reaction is 80 ~ 160 DEG C, and reaction pressure is 1.0 ~ 4.0MPa, and liquid phase weight air speed is 1 ~ 100 hour
-1, recycle ratio is 0 ~ 15.
6. the method for benzene and production of propylene isopropyl benzene according to claim 5, is characterized in that the operational condition at least one secondary response district is: temperature of reaction is 90 ~ 150 DEG C, and reaction pressure is 2.0 ~ 3.0MPa, and liquid phase weight air speed is 1 ~ 60 hour
-1, recycle ratio is 0 ~ 10.
7. the method for benzene and production of propylene isopropyl benzene according to claim 1, is characterized in that the recycle ratio of main reaction region is greater than the recycle ratio in secondary response district.
8. the method for benzene and production of propylene isopropyl benzene according to claim 1, is characterized in that described catalyzer is selected from Beta zeolite, mordenite or has the zeolite of MWW laminate structure.
9. the method for benzene and production of propylene isopropyl benzene according to claim 1, is characterized in that propylene segmentation enters main reaction region.
10. the method for benzene and production of propylene isopropyl benzene according to claim 1, it is characterized in that benzene enters from the top of main reaction region, the logistics looping back main reaction region enters from the top of main reaction region, and the logistics entering at least one secondary response district enters from the top at least one secondary response district.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310512683.4A CN104557438B (en) | 2013-10-28 | 2013-10-28 | The method of benzene and production of propylene isopropylbenzene |
| TW103137062A TWI674252B (en) | 2013-10-28 | 2014-10-27 | Method for producing cumene from benzene and propylene |
| SG10201406982WA SG10201406982WA (en) | 2013-10-28 | 2014-10-27 | Method for Producing Isopropyl Benzene from Benzene and Propylene |
| ES14190441.7T ES2581914T3 (en) | 2013-10-28 | 2014-10-27 | Method for producing isopropylbenzene from benzene and propylene |
| BR102014026858-8A BR102014026858B1 (en) | 2013-10-28 | 2014-10-27 | method for producing isopropylbenzene from benzene and propylene |
| EP14190441.7A EP2865660B1 (en) | 2013-10-28 | 2014-10-27 | Method for producing isopropyl benzene from benzene and propylene |
| JP2014219538A JP6599609B2 (en) | 2013-10-28 | 2014-10-28 | Process for producing isopropylbenzene from benzene and propylene |
| US14/525,857 US9828307B2 (en) | 2013-10-28 | 2014-10-28 | Method for producing isopropyl benzene from benzene and propylene |
| KR1020140147268A KR102229126B1 (en) | 2013-10-28 | 2014-10-28 | Method for producing isopropyl benzene from benzene and propylene |
| JP2019126986A JP6748266B2 (en) | 2013-10-28 | 2019-07-08 | Method for producing isopropylbenzene from benzene and propylene |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310512683.4A CN104557438B (en) | 2013-10-28 | 2013-10-28 | The method of benzene and production of propylene isopropylbenzene |
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| CN104557438B CN104557438B (en) | 2017-06-20 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1228073A (en) * | 1996-08-20 | 1999-09-08 | 陶氏化学公司 | Process for production of alkylated benzenes |
| CN1235146A (en) * | 1999-04-09 | 1999-11-17 | 中国石油天然气集团公司 | Method for preparing ethylbenzene and/or isopropylbenzene from thin ethylene and/or propylene |
| US6835862B1 (en) * | 1997-06-16 | 2004-12-28 | Uop Llc | Alkylation process operating at high recycle ratios |
| CN101466815A (en) * | 2006-05-10 | 2009-06-24 | 埃克森美孚化学专利公司 | Mixed phase, multistage alkylaromatics production |
| CN102464566A (en) * | 2010-11-17 | 2012-05-23 | 中国石油化工股份有限公司 | Method for producing isopropylbenzene by using benzene and propylene |
-
2013
- 2013-10-28 CN CN201310512683.4A patent/CN104557438B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1228073A (en) * | 1996-08-20 | 1999-09-08 | 陶氏化学公司 | Process for production of alkylated benzenes |
| US6835862B1 (en) * | 1997-06-16 | 2004-12-28 | Uop Llc | Alkylation process operating at high recycle ratios |
| CN1235146A (en) * | 1999-04-09 | 1999-11-17 | 中国石油天然气集团公司 | Method for preparing ethylbenzene and/or isopropylbenzene from thin ethylene and/or propylene |
| CN101466815A (en) * | 2006-05-10 | 2009-06-24 | 埃克森美孚化学专利公司 | Mixed phase, multistage alkylaromatics production |
| CN102464566A (en) * | 2010-11-17 | 2012-05-23 | 中国石油化工股份有限公司 | Method for producing isopropylbenzene by using benzene and propylene |
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