CN102295516A - Method for producing isopropyl benzene - Google Patents
Method for producing isopropyl benzene Download PDFInfo
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- CN102295516A CN102295516A CN2010102081518A CN201010208151A CN102295516A CN 102295516 A CN102295516 A CN 102295516A CN 2010102081518 A CN2010102081518 A CN 2010102081518A CN 201010208151 A CN201010208151 A CN 201010208151A CN 102295516 A CN102295516 A CN 102295516A
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- benzene
- isopropyl benzene
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- propylene
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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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
The invention relates to a method for producing isopropyl benzene. The method mainly solves the problem of low selectivity of mono-isopropyl benzene in liquid phase alkylation reaction of benzene and propylene in the prior art. The propylene and the benzene are used as reaction raw materials in the method; the reaction raw materials are in contact with a catalyst to synthesize the isopropyl benzene in a liquid phase mode under the conditions that the reaction temperature is 100 to 170 DEG C, the reaction pressure is 1.5 to 2.8MPa, the molar ratio of the benzene to the propylene is 2 to 5 and the weight airspeed of the propylene is 0.2 to 8.0h<-1>; the catalyst comprises the following components in part by weight: a) 50 to 80 parts of at least one of Y, Beta and MCM-22 molecular sieves, and b) 20 to 50 parts of inorganic oxide; the catalyst is subjected to modifying treatment by using the mixed solution of the benzene and the isopropyl benzene, wherein the treatment temperature is 110 to 160 DEG C, the treatment pressure is 2.0 to 2.8MPa, the treatment time is 2 to 200 hours, and the weight airspeed of the mixed solution is 2 to 20h<-1>; and in the mixed solution of the benzene and the isopropyl benzene, the weight ratio of the benzene to the isopropyl benzene is 15 to 80. According to the technical scheme, the problem is well solved, and the method can be used for industrial production of preparing the isopropyl benzene by propylene liquid phase alkylation.
Description
Technical field
The present invention relates to a kind of method that is used to produce isopropyl benzene.
Background technology
Isopropyl benzene is an important intermediate raw material of producing phenol, acetone and alpha-methyl styrene.Phenol more than 90% is to adopt cumene method production in the world at present.The traditional method of industrial production isopropyl benzene has the solid phosphoric acid method (SPA method) of UOP (UOP) and the improvement AlCl of Monsanto/Lummus Crest company
3Method.SPA operational condition harshness, impurity is many, can not improve the productive rate of isopropyl benzene by reverse alkylation.And AlCl
3Though method has than the demulcent reaction conditions, and can improve the productive rate of isopropyl benzene by reverse alkylation, this catalytic erosion is strong, pollute heavy and aftertreatment numerous and diverse.
Molecular sieve liquid phase alkylation methods because reaction conditions mitigations, transformation efficiency height, selectivity is good, impurity is few, pollution-free, do not have to corrode; main by product polyisopropylbenzene can change isopropyl benzene into via reverse alkylation; make the isopropyl benzene productive rate up to more than 99%; be each institute of big industrial group company common concern in recent years, and an advanced technology of competitively development research, to significant " cleaning procedure " technology of environment protection.
The isopropyl benzene molecular sieve catalyst of heavy industrialization has the Y zeolite of Uop Inc., the beta-molecular sieve of EniChem company, the MCM-22 molecular sieve of Mobil company at present.
Document CN1113649 provides a kind of steam treatment process of zeolite catalyst being carried out the part dealuminzation.Document CN1125641 provides a kind of method for preparing the isopropyl benzene zeolite catalyst of high reactivity, highly selective, is mainly used in the reaction of bubbling bed.CN1227770 then adopts mineral acid treatment β zeolite to prepare alkylation catalyst.The common drawback of all aforesaid methods is that single isopropyl benzene selectivity of the isopropyl benzene catalyzer produced is low, is difficult to industrial application.
Summary of the invention
Technical problem to be solved by this invention is to exist in the prior art in benzene and the propylene liquid-phase alkylation reaction, and the low problem of single isopropyl benzene selectivity provides a kind of new method that is used to produce isopropyl benzene.This method has the high characteristics of single isopropyl benzene selectivity.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of method that is used to produce isopropyl benzene, with propylene and benzene is reaction raw materials, in temperature of reaction is 100～170 ℃, reaction pressure is 1.5～2.8MPa, benzene/propylene mol ratio is 2～5, and the propylene weight air speed is 0.2～8.0 hour
-1Reaction raw materials contacts the liquid phase synthesizing iso-propylbenzene under the condition with catalyzer, and used catalyzer comprises following component in parts by weight:
A) 50～80 parts be selected from least a molecular sieve in Y, β or the MCM-22 molecular sieve;
B) 20～50 parts inorganic oxide;
Wherein catalyzer is handled with the mixed solution modification of benzene and isopropyl benzene, and treatment temp is 110～160 ℃, and processing pressure is 2.0～2.8MPa, and the treatment time is 2～200 hours, and the mixed solution weight space velocity is 2～20 hours
-1In the mixed solution of described benzene and isopropyl benzene, the weight ratio of benzene and isopropyl benzene is 15～80.
In the technique scheme, the temperature of reaction preferable range is 120～160 ℃, and the reaction pressure preferable range is 1.5～2.5MPa, and benzene/olefin molar ratio preferable range is 2～4, and propylene weight air speed preferable range is 0.3～6.0 hour
-1The treatment temp preferable range is 120～155 ℃, and more preferably scope is 135～150 ℃.The processing pressure preferable range is 2.0～2.6MPa, and more preferably scope is 2.2～2.5MPa.The treatment time preferable range is 15～150 hours, and more preferably scope is 30～120 hours.Mixed solution weight space velocity preferable range is 3～18 hours
-1, more preferably scope is 5～15 hours
-1In the mixed solution of described benzene and isopropyl benzene, the weight ratio preferable range of benzene and isopropyl benzene is 17～60, and more preferably scope is 19～49.Consumption preferable range in the parts by weight molecular sieve is 50～75 parts, and the consumption preferable range of inorganic oxide is 50～25 parts.Described molecular sieve preferred version is for being selected from beta-molecular sieve.Described inorganic oxide preferred version is to be selected from least a in aluminum oxide, titanium oxide, zinc oxide or the zirconium white.
Catalyzer in the inventive method can prepare as follows: at least a molecular sieve that will be selected from Y, β or the MCM-22 molecular sieve exchanges with ammonium salt, and the content that makes alkalimetal ion wherein is below 0.01% (weight).The molecular sieve of handling well is mixed with inorganic oxide, add dilute nitric acid solution kneading, extruded moulding, oven dry back pelletizing got the work in-process catalyzer in 4 hours 580 ℃ of roastings then.With above-mentioned work in-process catalyzer at 110～160 ℃, 2.0～2.8MPa with the mixture process of benzene and isopropyl benzene 2～200 hours, the mixed solution weight space velocity is 3～20 hours
-1Be cooled to normal temperature then, can't check organism with nitrogen purging to tail gas and can obtain finished catalyst.
The inventive method is handled by under the simulation reaction condition molecular sieve being carried out modification, thereby makes single isopropyl benzene selectivity of high reactivity position quilt effective passivation effectively improvement isopropyl benzene catalyzer in the catalyzer.Use the inventive method, 150 ℃ of temperature, pressure 2.5MPa, benzene/propylene mol ratio 3.0, propylene weight air speed 1.5 hours
-1React under the condition, single isopropyl benzene selectivity is 92.8%, has improved 5.8% than undressed catalyzer, has obtained better technical effect.
The invention will be further elaborated below by embodiment.
Embodiment
[embodiment 1]
According to synthetic beta-molecular sieve (the silica alumina ratio SiO of method described in the CN1249270A
2/ Al
2O
3Be 23), synthetic good molecular sieve is exchanged to wherein alkali metal ion content measured less than 100ppm with ammonium nitrate.
With the molecular sieve handled well 100 grams, evenly mixed with 35 gram aluminum oxide, adds 145 milliliter of 5% (weight) salpeter solution, 5 gram sesbania powder kneadings extruded moulding after 2 hours.The catalyzer of forming 150 ℃ of oven dry, is warming up to 580 ℃ of roastings 4 hours then under air atmosphere, obtains catalyst A.
[embodiment 2]
Catalyst A 100 is restrained in the isothermal fixed bed of packing into, handle, obtain catalyst B with the mixed solution modification of benzene (98 weight %) and isopropyl benzene (2 weight %).Treatment temp is 150 ℃, and processing pressure is 2.5MPa, and the treatment time is 120 hours, and the mixed solution weight space velocity is 15 hours
-1
[embodiment 3]
Catalyst B is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.5 hours
-1, 150 ℃ of temperature of reaction, reaction pressure 2.7MPa, reaction product is isopropyl benzene and polyisopropylbenzene.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 3.1 (moles), outlet isopropyl benzene concentration 35%, and single isopropyl benzene weight selectivity is in benzene 92.8%.
[embodiment 4]
Get commercially available beta-molecular sieve (silica alumina ratio SiO
2/ Al
2O
3Be 23), exchange to wherein alkali metal ion content measured less than 100ppm with ammonium nitrate.Get the above-mentioned molecular sieve of 100 grams, mixed evenly with 25 gram aluminum oxide, 10 gram zinc oxide, 5 gram zirconium whites, 5 gram titanium oxide, adds 145 milliliter of 5% (weight) salpeter solution, 5 gram sesbania powder kneadings extruded moulding after 2 hours.The catalyzer of forming 150 ℃ of oven dry, is warming up to 580 ℃ of roastings 4 hours then under air atmosphere, obtains catalyzer C.Catalyzer C100 is restrained in the isothermal fixed bed of packing into, handle, obtain catalyzer D with the mixed solution modification of benzene (95 weight %) and isopropyl benzene (5 weight %).Treatment temp is 130 ℃, and processing pressure is 2.2MPa, and the treatment time is 30 hours, and the mixed solution weight space velocity is 5 hours
-1
[embodiment 5]
Catalyzer D is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.0 hours
-1, 160 ℃ of temperature of reaction, reaction pressure 2.7MPa, reaction product is isopropyl benzene and polyisopropylbenzene mixture.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 3.0 (moles), and outlet isopropyl benzene concentration reaches 36%, and single isopropyl benzene weight selectivity is in benzene 92.5%.
[Comparative Examples 1]
Catalyst A is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.0 hours
-1, 150 ℃ of temperature of reaction, reaction pressure 2.7MPa, reaction product is isopropyl benzene and polyisopropylbenzene mixture.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 3.1 (moles), and outlet isopropyl benzene concentration is 32%, and single isopropyl benzene weight selectivity counts 87% with benzene.
[Comparative Examples 2]
Catalyzer C is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.0 hours
-1, 155 ℃ of temperature of reaction, reaction pressure 2.7MPa, reaction product is isopropyl benzene and polyisopropylbenzene mixture.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 3.0 (moles), and outlet isopropyl benzene concentration is 31%, and single isopropyl benzene weight selectivity counts 85% with benzene.
[embodiment 6]
Get commercially available hydro-thermal ultra-steady Y molecular sieve (silica alumina ratio SiO
2/ Al
2O
3Be 12), exchange to wherein alkali metal ion content measured less than 100ppm with ammonium nitrate.Get the above-mentioned molecular sieve of 100 grams, mixed evenly with 35 gram aluminum oxide, adds 130 milliliter of 5% (weight) salpeter solution, 5 gram sesbania powder kneadings extruded moulding after 2 hours.The catalyzer of forming 150 ℃ of oven dry, is warming up to 580 ℃ of roastings 4 hours then under air atmosphere, obtains catalyzer E.Catalyzer E100 is restrained in the isothermal fixed bed of packing into, handle, obtain catalyzer F with the mixed solution modification of benzene (97 weight %) and isopropyl benzene (3 weight %).Treatment temp is 120 ℃, and processing pressure is 2.2MPa, and the treatment time is 50 hours, and the mixed solution weight space velocity is 10 hours
-1
Catalyzer F is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.0 hours
-1, 180 ℃ of temperature of reaction, reaction pressure 3.0MPa, reaction product is isopropyl benzene and polyisopropylbenzene mixture.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 4.0 (moles), and outlet isopropyl benzene concentration is 30%, and single isopropyl benzene weight selectivity counts 91.5% with benzene.
[Comparative Examples 3]
Catalyzer E is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.0 hours
-1, 180 ℃ of temperature of reaction, reaction pressure 3.0MPa, reaction product is isopropyl benzene and polyisopropylbenzene mixture.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 4.0 (moles), and outlet isopropyl benzene concentration is 26%, and single isopropyl benzene weight selectivity counts 81.2% with benzene.
[embodiment 7]
Get synthetic MCM-22 molecular sieve (the silica alumina ratio SiO in laboratory
2/ Al
2O
3Be 24), exchange to wherein alkali metal ion content measured less than 100ppm with ammonium nitrate.Get the above-mentioned molecular sieve of 100 grams, mixed evenly with 35 gram aluminum oxide, adds 165 milliliter of 5% (weight) salpeter solution, 5 gram sesbania powder kneadings extruded moulding after 2 hours.The catalyzer of forming 150 ℃ of oven dry, is warming up to 580 ℃ of roastings 4 hours then under air atmosphere, obtains catalyzer G.Catalyzer G100 is restrained in the isothermal fixed bed of packing into, handle, obtain catalyzer H with the mixed solution modification of benzene (96 weight %) and isopropyl benzene (4 weight %).Treatment temp is 120 ℃, and processing pressure is 2.2MPa, and the treatment time is 80 hours, and the mixed solution weight space velocity is 12 hours
-1
Catalyzer H is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.0 hours
-1, 150 ℃ of temperature of reaction, reaction pressure 2.5MPa, reaction product is isopropyl benzene and polyisopropylbenzene mixture.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 2.0 (moles), and outlet isopropyl benzene concentration is 41%, and single isopropyl benzene weight selectivity counts 90.5% with benzene.
[Comparative Examples 3]
Catalyzer G is ground into 20～60 purpose particles, gets 1.0 gram catalyzer and carry out the propylene liquid-phase alkylation reaction in fixed-bed reactor, reaction conditions is: propylene air speed 1.0 hours
-1, 150 ℃ of temperature of reaction, reaction pressure 2.5MPa, reaction product is isopropyl benzene and polyisopropylbenzene mixture.Reaction result is: propylene conversion 100%, product propyl group selectivity are greater than 99.2%, and total benzene hydrocarbon ratio is 2.0 (moles), and outlet isopropyl benzene concentration is 35%, and single isopropyl benzene weight selectivity counts 84.5% with benzene.
Claims (9)
1. a method that is used to produce isopropyl benzene is a reaction raw materials with propylene and benzene, is 100～170 ℃ in temperature of reaction, and reaction pressure is 1.5～2.8MPa, and benzene/propylene mol ratio is 2～5, and the propylene weight air speed is 0.2～8.0 hour
-1Reaction raw materials contacts the liquid phase synthesizing iso-propylbenzene under the condition with catalyzer, and used catalyzer comprises following component in parts by weight:
A) 50～80 parts be selected from least a molecular sieve in Y, β or the MCM-22 molecular sieve;
B) 20～50 parts inorganic oxide;
Wherein catalyzer is handled with the mixed solution modification of benzene and isopropyl benzene, and treatment temp is 110～160 ℃, and processing pressure is 2.0～2.8MPa, and the treatment time is 2～200 hours, and the mixed solution weight space velocity is 2～20 hours
-1In the mixed solution of described benzene and isopropyl benzene, the weight ratio of benzene and isopropyl benzene is 15～80.
2. according to the described method that is used to produce isopropyl benzene of claim 1, it is characterized in that treatment temp is 120～155 ℃, processing pressure is 2.0～2.6MPa, and the treatment time is 15～150 hours, and the mixed solution weight space velocity is 3～18 hours
-1
3. according to the described method that is used to produce isopropyl benzene of claim 2, it is characterized in that treatment temp is 135～150 ℃, processing pressure is 2.2～2.5MPa, and the treatment time is 30～120 hours, and the mixed solution weight space velocity is 5～15 hours
-1
4. according to the described method that is used to produce isopropyl benzene of claim 1, it is characterized in that in the mixed solution of described benzene and isopropyl benzene that the weight ratio of benzene and isopropyl benzene is 17～60.
5. according to the described method that is used to produce isopropyl benzene of claim 4, it is characterized in that in the mixed solution of described benzene and isopropyl benzene that the weight ratio of benzene and isopropyl benzene is 19～49.
6. according to the described method that is used to produce isopropyl benzene of claim 1, it is characterized in that the consumption in the parts by weight molecular sieve is 50～75 parts, the consumption of inorganic oxide is 50～25 parts.
7. according to the described method that is used to produce isopropyl benzene of claim 1, it is characterized in that described molecular screening is from beta-molecular sieve.
8. according to the described method that is used to produce isopropyl benzene of claim 1, it is characterized in that described inorganic oxide is selected from least a in aluminum oxide, titanium oxide, zinc oxide or the zirconium white.
9. according to the described method that is used to produce isopropyl benzene of claim 1, it is characterized in that temperature of reaction is 120～160 ℃, 1.5～2.5MPa, benzene/propylene mol ratio is 2～4, the propylene weight air speed is 0.3～6.0 hour
-1
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| CN2010102081518A CN102295516B (en) | 2010-06-24 | 2010-06-24 | Method for producing isopropyl benzene |
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|---|---|---|---|
| CN2010102081518A CN102295516B (en) | 2010-06-24 | 2010-06-24 | Method for producing isopropyl benzene |
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| CN102295516B CN102295516B (en) | 2013-06-05 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114762832A (en) * | 2021-01-12 | 2022-07-19 | 洛阳市科创石化科技开发有限公司 | Preparation method and application of catalyst for producing mixed propylbenzene by alkylation of benzene and carbon tetraenes |
Citations (5)
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|---|---|---|---|---|
| EP1252927A1 (en) * | 1999-12-29 | 2002-10-30 | Consejo Superior De Investigaciones Cientificas | Catalyst for alkylating aromatic compounds with olefins, alcohols or polyalkylated aromatic compounds |
| CN101045209A (en) * | 2006-03-27 | 2007-10-03 | 中国石油化工股份有限公司 | Catalyst for synthesizing iso-propylbenzene |
| CN101045211A (en) * | 2006-03-27 | 2007-10-03 | 中国石油化工股份有限公司 | Catalyst for diisopropylbenzene alkyl transfer |
| CN101091921A (en) * | 2006-06-21 | 2007-12-26 | 中国石油化工股份有限公司 | Method for preparing oxidation catalyst of cyclopropene |
| US20080171901A1 (en) * | 2007-01-12 | 2008-07-17 | Reynolds Thomas M | Aromatic Transalkylation Using A LZ-210 Zeolite |
-
2010
- 2010-06-24 CN CN2010102081518A patent/CN102295516B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1252927A1 (en) * | 1999-12-29 | 2002-10-30 | Consejo Superior De Investigaciones Cientificas | Catalyst for alkylating aromatic compounds with olefins, alcohols or polyalkylated aromatic compounds |
| CN101045209A (en) * | 2006-03-27 | 2007-10-03 | 中国石油化工股份有限公司 | Catalyst for synthesizing iso-propylbenzene |
| CN101045211A (en) * | 2006-03-27 | 2007-10-03 | 中国石油化工股份有限公司 | Catalyst for diisopropylbenzene alkyl transfer |
| CN101091921A (en) * | 2006-06-21 | 2007-12-26 | 中国石油化工股份有限公司 | Method for preparing oxidation catalyst of cyclopropene |
| US20080171901A1 (en) * | 2007-01-12 | 2008-07-17 | Reynolds Thomas M | Aromatic Transalkylation Using A LZ-210 Zeolite |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114762832A (en) * | 2021-01-12 | 2022-07-19 | 洛阳市科创石化科技开发有限公司 | Preparation method and application of catalyst for producing mixed propylbenzene by alkylation of benzene and carbon tetraenes |
| CN114762832B (en) * | 2021-01-12 | 2023-12-08 | 洛阳市科创石化科技开发有限公司 | Preparation method and application of catalyst for producing mixed propylbenzene by alkylation of benzene and carbon tetraolefin |
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