CN104557438B - The method of benzene and production of propylene isopropylbenzene - Google Patents
The method of benzene and production of propylene isopropylbenzene Download PDFInfo
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- CN104557438B CN104557438B CN201310512683.4A CN201310512683A CN104557438B CN 104557438 B CN104557438 B CN 104557438B CN 201310512683 A CN201310512683 A CN 201310512683A CN 104557438 B CN104557438 B CN 104557438B
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Abstract
The present invention relates to a kind of benzene and the method for production of propylene isopropylbenzene, mainly solve the problems, such as that prior art has benzene alkene lower than high, propylene conversion.The present invention enters main reaction region by using a) benzene and propylene, is contacted with catalyst, generates first burst of logistics；B) first burst of logistics is divided into two parts, and a part loops back main reaction region, and another part enters at least one secondary response area；C) logistics into secondary response area is contacted with catalyst, generates second burst of logistics；d）Second burst of logistics is divided into two parts, and a part loops back secondary response area, and the technical scheme that another part obtains product isopropylbenzene into down-stream preferably solves the problem, can be used in the industrial production of benzene and production of propylene isopropylbenzene.
Description
Technical field
The present invention relates to a kind of benzene and the method for production of propylene isopropylbenzene.
Background technology
Isopropylbenzene is a kind of important Organic Chemicals, be produce phenol, acetone and AMS it is main in
Between compound.Industrially isopropylbenzene is prepared by propylene and benzene alkylation reaction, and its accessory substance is mainly polyisopropylbenzene.
Just disclosed in the presence of acidic early in UOP in 1945, in the method that propylene and benzene reaction prepare isopropylbenzene（SPA methods）
（US2382318）, SPA methods with solid phosphoric acid as alkylation catalyst, because solid phosphoric acid can not be catalyzed transalkylation reaction,
So there is no transalkylation portion in technological process.Therefore, SPA methods can only be in benzene alkene mol ratio high（5~7）Under the conditions of transport
OK, and the yield of its isopropylbenzene is only 95% or so.Last century the eighties, Monsanto companies are developed with AlCl3It is alkane
The isopropylbenzene production technology of base catalyst, and realize commercial Application.Due to AlCl3Transalkylation reaction can not be equally catalyzed,
Therefore, with AlCl3Method production isopropylbenzene it is still relatively low in terms of the yield of isopropylbenzene, while there is also serious pollution problem and
Corrosion of equipment problem.
In last century the nineties, Dow, CD Tech, Mobil-Badger, Enichem and UOP etc.（US4992606、
US5362697、US5453554、US5522984、US5672799、US6162416、US6051521）Companies disclose with
Micro-pore zeolite is catalyst, the fixed-bed process flow with transalkylation ability.In the prior art, benzene and propylene exist first
Reaction is alkylated in alkylation reaction device, the polysubstituted isopropylbenzene of alkylated reaction generation is more by after distillation system separation
Substitution isopropylbenzene carries out transalkylation reaction with after benzene mixing into the transalkylation reaction zone of a single bed again.
In existing disclosed isopropylbenzene technology, the alkylation of benzene and propylene is all using single, multistage laminar fixed bed
Reactor, and propylene sectional feeding and reaction solution outside circulation, benzene alkene ratio typically larger than 2.0, in fact, most of
Benzene alkene ratio both greater than 3.0 in running gear.Limit benzene alkene is than the further technology barrier for reducing：Further reduce benzene alkene ratio
It is even lower to 2.0, or because too high density of propylene causes rapid catalyst deactivation, or because too high outer circulation amount is made
Into the deficiency of propylene conversion, or because too high reaction temperature causes the too high of impurity n-proplbenzene in product.Recently, document
US6835862B1 is disclosed by process optimization, and the inactivation speed of catalyst can be reduced using reaction solution outer circulation amount higher
Rate.However, using single reactor and reaction solution outer circulation higher than technology, it is difficult to solve above three contradiction simultaneously
Problem.
The content of the invention
The technical problems to be solved by the invention are that prior art has that benzene alkene is lower than high, propylene conversion, carries
For a kind of new benzene and the method for production of propylene isopropylbenzene.The method has benzene alkene than low, the characteristics of propylene conversion is high.
In order to solve the above technical problems, the technical solution adopted by the present invention is as follows：A kind of benzene and production of propylene isopropylbenzene
Method, comprises the following steps：
A) benzene and propylene enter main reaction region, are contacted with catalyst, generate first burst of logistics；
B) first burst of logistics is divided into two parts, and a part loops back main reaction region, and another part enters at least one time instead
Answer area；
C) logistics into secondary response area is contacted with catalyst, generates second burst of logistics；
d）Second burst of logistics is divided into two parts, and a part loops back secondary response area, and another part is obtained into down-stream
Product isopropylbenzene.
In above-mentioned technical proposal, it is preferable that the main reaction region and at least one secondary response area are all at least one section anti-
Device is answered, or the reaction zone being in series by least two single hop reactors, or at least one single hop reactor and extremely
The reaction zone that few one at least two sections reactor is in series.
In above-mentioned technical proposal, it is preferable that the operating condition of the main reaction region is：Benzene is 0.5 with the mol ratio of propylene
~3.0, propylene weight air speed is 0.1 ~ 10 hour-1, reaction temperature is 90~180 DEG C, and reaction pressure is 1.0~4.0MPa, is followed
Ring ratio is 1 ~ 50.It is highly preferred that the operating condition of the main reaction region is：Benzene is 1.0~3.0, propylene with the mol ratio of propylene
Weight space velocity is 0.2 ~ 5.0 hour-1, reaction temperature be 95~150 DEG C, reaction pressure be 2.0~3.0MPa, recycle ratio be 2 ~
25。
In above-mentioned technical proposal, it is preferable that the operating condition at least one secondary response area is：Reaction temperature is 80~160
DEG C, reaction pressure is 1.0~4.0MPa, and liquid phase weight air speed is 1 ~ 100 hour-1, recycle ratio is 0 ~ 15.It is highly preferred that at least
The operating condition in one secondary response area is：Reaction temperature is 90~150 DEG C, and reaction pressure is 2.0~3.0MPa, and liquid phase weight is empty
Speed is 1 ~ 60 hour-1, recycle ratio is 0 ~ 10.
In above-mentioned technical proposal, it is preferable that recycle ratio of the recycle ratio of main reaction region more than secondary response area.
In above-mentioned technical proposal, it is preferable that the catalyst is selected from Beta zeolites, modenite or with MWW stratiform knots
The zeolite of structure.
In above-mentioned technical proposal, it is preferable that propylene segmentation enters main reaction region.
In above-mentioned technical proposal, it is preferable that benzene enters from the top of main reaction region, the logistics of main reaction region from master is looped back
The top of reaction zone enters.
In above-mentioned technical proposal, it is preferable that enter the logistics at least one secondary response area from least one secondary response area
Top enters.
In the inventive method, the pressure refers to gauge pressure.The recycle ratio is circulation logistics and reactor effluent stream
Weight ratio.
The catalyst used in the inventive method is selected from Beta zeolites, modenite or the zeolite with MWW layer structures.
Wherein, the zeolite with MWW layer structures can be selected from MCM-22, MCM-56, MCM-49, and according to document
The disclosed zeolites with MWW structures of CN200410066636.2 and CN200610029979.0.
In the inventive method, secondary response area can also add benzene logistics and propylene stream.
In order to solve under the conditions of low benzene alkene ratio, propylene conversion is low, catalyst is easily inactivated and product in impurity just
Propyl benzene content is high, and these three conflicting problems, the inventive method is provided with least two reaction zones, makes the first reaction zone
Effluent stream enters at least second reaction zone and continues to react, and the first reaction zone runs under the conditions of recycle ratio higher, and second
In relatively low recycle ratio or almost operation under conditions of no outer circulation material presence, this substantially extends total stopping to reaction zone
Stay the time.Propylene almost reacts completely in the first reaction zone, and a small amount of unreacted propylene continues in second reaction zone reaction, so that
Ensure that the high conversion of propylene.Using the inventive method, benzene alkene ratio can be reduced to less than 2.0, and propylene conversion can be big
In 99.99%, n-proplbenzene content can be less than 120 mg/kg isopropylbenzenes in product, achieve preferable technique effect.
Brief description of the drawings
Fig. 1 is process flow diagram of the invention, and by taking two reaction zones containing primary and secondary as an example, each reaction zone is two
Layer.
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 area, and 3 is benzene feedstock, and 4 is propylene, and 5 is to enter main reaction region
The propylene of the first beds, 6 is the propylene into the beds of main reaction region second, and 7 is main reaction region effluent stream,
8 is the logistics for looping back main reaction region, and 9 is the logistics into secondary response area, and 10 is product stream, and 11 is to loop back secondary response area
Logistics.
Below by embodiment, the present invention is further elaborated.
Specific embodiment
【Embodiment 1】
By the technological process of Fig. 1, comprising two reactors, each reactor includes two beds, wherein each
Each beds of reactor are mounted with 20 grams of preformed catalysts containing MCM-56 zeolites.
The reaction condition of main reactor is：Every section of 125 DEG C of bed reaction temperature, reaction pressure 2.5MPa is urged into every section
The propylene flow of agent bed 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 condition of secondary response device is：Every section of 115 DEG C of bed reaction temperature, 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 in product
92mg/kg isopropylbenzenes.
【Embodiment 2】
By the technological process of Fig. 1, comprising two reactors, each reactor includes two beds, wherein each
Each beds of reactor are mounted with 10 grams of catalyst, and catalyst is according to side disclosed in document CN200410066636.2
It is prepared by method.
The reaction condition of main reactor is：Every section of 120 DEG C of bed reaction temperature, reaction pressure 2.5MPa is urged into every section
The propylene flow of agent bed 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
Hour-1, circular flow is 798 Grams Per Hours, and recycle ratio is 7.0.
The reaction condition of secondary response device is：Every section of 110 DEG C of bed reaction temperature, reaction pressure 2.5MPa, every section of catalyst
Bed 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 be 110 grams/it is small
When, recycle ratio is 1.0.
Continuous operation 15 days, reaction result：Propylene conversion 99.99%, n-proplbenzene content 87mg/kg isopropylbenzenes in product.
【Embodiment 3】
By the technological process of Fig. 1, comprising two reactors, simply each reactor includes three beds, wherein
Each beds of each reactor are mounted with 20 grams of catalyst, and catalyst is disclosed according to document CN200410066636.2
Method prepare.
The reaction condition of main reactor is：Every section of 135 DEG C of bed reaction temperature, reaction pressure 2.5MPa is urged into every section
The propylene flow of agent bed 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 condition of secondary response device is：Every section of 105 DEG C of bed reaction temperature, reaction pressure 2.5MPa, first paragraph catalysis
Agent bed propylene flow is 5 Grams Per Hours, and two-stage catalytic agent bed is not passed through propylene in addition, and liquid phase air speed is 4.8 hours-1, circulation
Flow is 340 grams of hours, and recycle ratio is 1.2..
Continuous operation 7 days, reaction result：Propylene conversion 99.99%, n-proplbenzene content 50mg/kg isopropylbenzenes in product.
【Embodiment 4】
By the technological process of Fig. 1, comprising two reactors, simply each reactor includes a beds, wherein
Each beds of each reactor are mounted with 20 grams of catalyst, and catalyst is disclosed according to document CN200410066636.2
Method prepare.
The reaction condition of main reactor is：135 DEG C of catalyst bed reaction temperature, reaction pressure 3.0MPa, into catalysis
The propylene flow of agent bed 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
Hour-1, circular flow is 2360 Grams Per Hours, and recycle ratio is 12.
The reaction condition of secondary response device is：Every section of 110 DEG C of bed reaction temperature, 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 isopropyls in product
Benzene.
【Embodiment 5】
By the technological process of Fig. 1, comprising two reactors, each reactor includes two beds, wherein each
Each beds of reactor are mounted with 10 grams of preformed catalysts containing MCM-56 zeolites.
The reaction condition of main reactor is：Every section of 110 DEG C of bed reaction temperature, reaction pressure 2.5MPa is urged into every section
The propylene flow of agent bed 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 condition of secondary response device is：Every section of 100 DEG C of bed reaction temperature, reaction pressure 2.5MPa, liquid phase air speed is
17 hours-1, first paragraph beds propylene flow is 0 Grams Per Hour, the propylene flow of second segment beds for 0 gram/it is small
When, circular flow is 0 gram of hour.
Continuous operation 7 days, reaction result：Propylene conversion 99.99%, n-proplbenzene content 75mg/kg isopropylbenzenes in product.
【Embodiment 6】
By the technological process of Fig. 1, comprising two reactors, each reactor includes two beds, wherein each
Each beds of reactor are mounted with 10 grams of catalyst, and catalyst is according to side disclosed in document CN200610029979.0
It is prepared by method.
The reaction condition of main reactor is：Every section of 115 DEG C of bed reaction temperature, reaction pressure 2.7MPa is urged into every section
The propylene flow of agent bed 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 condition of secondary response device is：Every section of 120 DEG C of bed reaction temperature, reaction pressure 2.7MPa is urged into every section
The propylene flow of agent bed is 0 Grams Per Hour, and benzene flow is 75 Grams Per Hours, and circular flow is 91 Grams Per Hours, and recycle ratio is
0.5, liquid phase air speed is 9.1 hours-1。
Continuous operation 7 days, reaction result：Propylene conversion 99.98%, n-proplbenzene content 97mg/kg isopropylbenzenes in product.
【Comparative example 1】
Using the technological process of only one of which reactor, as shown in Fig. 2 reactor includes four sections of beds, propylene
It is divided into four parts and respectively enters four beds, benzene enters from reactor head, and each beds is mounted with 10 grams
Preformed catalyst containing MCM-22 zeolites.
Reaction condition is：Every section of 140 DEG C of bed reaction temperature, reaction pressure 2.7MPa, into every section of beds
Propylene flow is 15 Grams Per Hours, and benzene flow is 178 Grams Per Hours, and circular flow is 1428 Grams Per Hours, and benzene alkene ratio is 1.6, propylene
Weight space velocity 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 isopropylbenzenes in product.
The above results illustrate that using prior art under the conditions of low benzene alkene ratio, the conversion ratio of propylene is relatively low, while n-proplbenzene
Content is also higher.
Claims (6)
1. a kind of method of benzene and production of propylene isopropylbenzene, comprises the following steps：
A) benzene and propylene enter main reaction region, are contacted with catalyst, generate first burst of logistics；
B) first burst of logistics is divided into two parts, and a part loops back main reaction region, and another part enters at least one secondary response area；
C) logistics into secondary response area is contacted with catalyst, generates second burst of logistics；
D) second burst of logistics is divided into two parts, and a part loops back secondary response area, and another part obtains product into down-stream
Isopropylbenzene；
The operating condition of the main reaction region is：Benzene is 0.5~3.0 with the mol ratio of propylene, and propylene weight air speed is 0.1~10
Hour-1, reaction temperature is 90~180 DEG C, and reaction pressure is 1.0~4.0MPa, and recycle ratio is 1~50；
The operating condition at least one secondary response area is：Reaction temperature be 80~160 DEG C, reaction pressure be 1.0~
4.0MPa, liquid phase weight air speed is 1~100 hour-1, recycle ratio is 0~15；
Wherein, recycle ratio of the recycle ratio of main reaction region more than secondary response area；
The catalyst is selected from Beta zeolites or the zeolite with MWW layer structures.
2. the method for benzene and production of propylene isopropylbenzene according to claim 1, it is characterised in that the main reaction region and at least
One secondary response area is all at least one section of reactor.
3. the method for benzene and production of propylene isopropylbenzene according to claim 1, it is characterised in that the operation of the main reaction region
Condition is：Benzene is 1.0~3.0 with the mol ratio of propylene, and propylene weight air speed is 0.2~5.0 hour-1, reaction temperature be 95~
150 DEG C, reaction pressure is 2.0~3.0MPa, and recycle ratio is 2~25.
4. the method for benzene and production of propylene isopropylbenzene according to claim 1, it is characterised in that at least one secondary response area
Operating condition is：Reaction temperature is 90~150 DEG C, and reaction pressure is 2.0~3.0MPa, and liquid phase weight air speed is 1~60 small
When-1, recycle ratio is 0~10.
5. the method for benzene and production of propylene isopropylbenzene according to claim 1, it is characterised in that propylene segmentation enters main reaction
Area.
6. the method for benzene and production of propylene isopropylbenzene according to claim 1, it is characterised in that top of the benzene from main reaction region
Into, loop back the logistics of main reaction region and enter from the top of main reaction region, at least one secondary response area logistics to
The top in a few secondary response area enters.
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 |
| ES14190441.7T ES2581914T3 (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 |
| SG10201406982WA SG10201406982WA (en) | 2013-10-28 | 2014-10-27 | Method for Producing Isopropyl Benzene from Benzene and Propylene |
| TW103137062A TWI674252B (en) | 2013-10-28 | 2014-10-27 | Method for producing cumene from benzene and propylene |
| BR102014026858-8A BR102014026858B1 (en) | 2013-10-28 | 2014-10-27 | method for producing isopropylbenzene from benzene and propylene |
| JP2014219538A JP6599609B2 (en) | 2013-10-28 | 2014-10-28 | Process for producing isopropylbenzene from benzene and propylene |
| KR1020140147268A KR102229126B1 (en) | 2013-10-28 | 2014-10-28 | Method for producing isopropyl benzene from benzene and propylene |
| US14/525,857 US9828307B2 (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 |
Applications Claiming Priority (1)
| 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 |
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| CN104557438A CN104557438A (en) | 2015-04-29 |
| CN104557438B true 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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|---|---|
| CN104557438A (en) | 2015-04-29 |
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