CN102746100A - Preparation method of cumene - Google Patents
Preparation method of cumene Download PDFInfo
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- CN102746100A CN102746100A CN201110101090XA CN201110101090A CN102746100A CN 102746100 A CN102746100 A CN 102746100A CN 201110101090X A CN201110101090X A CN 201110101090XA CN 201110101090 A CN201110101090 A CN 201110101090A CN 102746100 A CN102746100 A CN 102746100A
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- alpha
- isopropyl benzene
- cumene
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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 production of cumene through hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol, and aims to mainly solve the problems that a Pd catalyst is expensive, and a CuCr catalyst has low activity and causes serious environmental pollution during cumene production in the prior art. The method of the invention adopts a technical scheme composed of: taking hydrogen and alpha, alpha-dimethyl benzyl alcohol as raw materials, adopting cumene as a solvent, and under the conditions of a volume ratio of hydrogen to alpha, alpha-dimethyl benzyl alcohol of 100-500:1, a reaction temperature of 100-180DEG C, a reaction pressure of 0.1-5.0MPa, and a liquid-phase volume space velocity of 1-10.0h<-1>, contacting the raw materials with a catalyst in a fixed bed reactor to generate cumene. Specifically, the catalyst comprises the following components by weight: a) 10.0-45.0% of NiO; b) 45.0-75.0% of Al2O3; and c) 3.0-15.0% of at least one of MgO, CaO, BaO or ZrO2. The technical scheme of the invention well solve the problems, and can be used for industrial production of cumene through hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol.
Description
Technical field
The present invention relates to a kind of method of producing isopropyl benzene, particularly about a kind of hydrogenolysis α, alpha-alpha-dimethyl benzylalcohol is produced the method for isopropyl benzene.
Background technology
Propylene oxide is the third-largest acryloyl derivative except that Vestolen PP 7052 and vinyl cyanide, is important basic organic chemical industry's synthesis material, is mainly used in to produce polyethers, Ucar 35 etc.The maximum purposes of polyether glycol is to produce urethane plastic; Secondly as tensio-active agent, also be used as lubricant, hydraulic fluid, heat exchange fluid and quenching medium, emulsion foaming agent, multiple cutting and drawing-off agent component and dedicated solvent etc.China's propylene oxide is mainly used in the production polyether glycol.Second largest purposes is to be used to produce Ucar 35, alcohol ether, propylene carbonate, and then can make storage tank, bathroom fittings, shell etc.In addition, propylene oxide also be used on a small quantity coating, electronic chemical product, sanitising agent, non-ionics, oil field emulsion splitter, etc. industry.
This material mainly working method is chlorohydrination and ethylbenzene hydroperoxide method.Chlorohydrination is seriously polluted to environment, and the ethylbenzene hydroperoxide method has a large amount of coproduction by products-vinylbenzene to generate, thereby makes the production cost of propylene oxide receive the influence of the price volalility of co-product.In recent years, be oxygen source with the dicumyl peroxide, the method that propylene oxide is produced propylene oxide grows up gradually; This process environmental protection, safe; Co-product α, alpha-alpha-dimethyl benzylalcohol can generate isopropyl benzene through catalytic hydrogenolytic cleavage, and isopropyl benzene can return the peroxo-unit and realize recycle.With the technology ratio of ethylbenzene hydroperoxide method oxidation production propylene oxide, this process has advantages such as operational path is short, and facility investment is few, and no co-product and production prices are more stable.
U.S. Pat 6646139B2 has disclosed α, and alpha-alpha-dimethyl benzylalcohol catalytic hydrogenolysis is produced the technological process of isopropyl benzene, and this technology is to be hydrogen source with hydrogen; With the Cu-Cr oxide compound is catalyzer, 180 ℃ of temperature of reaction, and catalyst activity is lower; Owing to the existence of Cr species, environmental pollution is serious simultaneously.
Chinese patent CN1257138C has proposed to use H
2Method with CO gas mixture reduction Cu catalyzer because its catalyst system therefor remains the Cu-Cr catalyzer, exists catalyst activity low, the problem that environmental pollution is serious equally.
Chinese patent CN1308273C has announced a kind of α; The method of alpha-alpha-dimethyl phenylcarbinol liquid phase hydrogenolysis preparing isopropylbenzene, this method is a catalyzer with the 2.0wt%Pd/ cocoanut active charcoal, can the benzylalcohol hydrogenolysis be converted into isopropyl benzene; The transformation efficiency 96～98% of benzylalcohol generates the isopropyl benzene selectivity and reaches 99%.Will use in this technology-first low-carbon alcohol solvent and formic acid, acetate etc. is additive, this process using batch operation, and production efficiency is low, uses the Pd catalyzer, costs an arm and a leg.
From the above mentioned, prior art hydrogenolysis α, the catalyzer of alpha-alpha-dimethyl benzylalcohol mainly use Pd and Cu catalyst based.Use the Pd catalyzer to cost an arm and a leg; There is the problem that catalyst activity is low, environmental pollution is serious in use with the CuCr catalyzer of prior art for preparing.
Summary of the invention
There is expensive problem in technical problem to be solved by this invention when being prior art for preparing isopropyl benzene use Pd catalyzer, and the problem that activity is low, environmental pollution is serious when using the CuCr catalyzer provides a kind of new method for preparing isopropyl benzene.This method is used for hydrogenolysis α, and alpha-alpha-dimethyl benzylalcohol prepares in the isopropyl benzene reaction, and it is low that the catalyzer of employing and Pd catalyzer are compared price, compare with the CuCr catalyzer have active high, eco-friendly advantage.
For solving the problems of the technologies described above, the technical scheme that the present invention adopts is following: a kind of method of producing isopropyl benzene, with hydrogen and α; Alpha-alpha-dimethyl benzylalcohol is raw material, is solvent with the isopropyl benzene, hydrogen/α; The volume ratio of alpha-alpha-dimethyl benzylalcohol is 100～500: 1; Temperature of reaction is 100～180 ℃, and reaction pressure is 0.1～5.0MPa, and the liquid phase volume air speed is 1.0～10.0h
-1Under the condition, raw material contacts with catalyzer, and reaction generates isopropyl benzene and water, obtains the isopropyl benzene product through separation, and wherein catalyst system therefor comprises following component by weight percentage: a) 10.0～45.0%NiO; B) 45.0～75.0%Al
2O
3C) 3.0～15.0% be selected from MgO, CaO, BaO or ZrO
2In at least a.
In the technique scheme, NiO consumption preferable range is 15.0～30.0% in the catalyzer by weight percentage.Liquid phase volume air speed preferable range is 2.0～6.0h
-1, hydrogen/α, the volume ratio meter preferable range of alpha-alpha-dimethyl benzylalcohol is 200～400: 1.α by weight percentage in the said liquid phase feed, alpha-alpha-dimethyl benzylalcohol content is 20～40%, isopropyl benzene content is 60～80%.The temperature of reaction preferable range is 110～150 ℃; The reaction pressure preferable range is 1.0～3.0MPa.Be selected from MgO, CaO, BaO or ZrO by weight percentage
2In at least a consumption preferable range be 5.0～10.0%.
Preparation of Catalyst among the present invention adopts following steps: under 40～95 ℃; The nickel salt solution or the nickel ammine that in aluminium colloidal sol, add aequum obtain nickel aluminium colloidal sol; And to regulate its pH value be 8.0～11.0; With this colloidal sol rest on 50～100 ℃ down aging, then obtain the nickel alumina gel 60～140 ℃ of following thermal degradation, gel through washing, dry, catalyst precursor.Adopt equi-volume impregnating will be selected from Mg
2+, Ca
2+, Ba
2+Or Zr
4+In at least a being immersed on the catalyst precursor, obtain required nickel-base catalyst after the roasting by weight percentage, the consumption preferable range of NiO amount is 15～30%; Be selected from MgO, CaO, BaO or ZrO
2In at least a consumption preferable range be 5.0～10.0%; The pH value of nickel aluminium colloidal sol is through at least a adjusting the in volatile salt, yellow soda ash, the alkali metal hydroxide, and preferable range is 8.5～10; The gel aging temperature is 60～85 ℃; The decomposition temperature of gel is 85～120 ℃.
α, alpha-alpha-dimethyl benzylalcohol hydrogenolysis process can be divided into for two steps, the first step α, the dehydration of alpha-alpha-dimethyl benzylalcohol generates alpha-methyl styrene; Second step generated isopropyl benzene with the alpha-methyl styrene hydrogenation.Except that above reaction took place, α, alpha-alpha-dimethyl benzylalcohol because of benzene ring hydrogenation generates normenthane, had the existence of part phenol, benzene hexanone, dicumyl peroxide easily because of chain rupture generates toluene/ethylbenzene simultaneously in the reaction raw materials.At α, can be on the acid sites of catalyzer in the hydrogenolysis process of alpha-alpha-dimethyl benzylalcohol produce the alpha-methyl styrene intermediate product, this material polymerization and cause catalyst activity to reduce.The quantity at catalyst acid center and strength of acid can be regulated through introducing basic oxide and handling procedure; The Ni metal has good hydrogenation activity can be with a spot of dicumyl peroxide in raw material hydrogenation in the lump, and the Ni catalyzer has satisfactory stability property simultaneously, is used for this reaction, can reduce temperature of reaction, improves reaction efficiency.Compare with noble metal catalyst, it is low that the present invention adopts catalyzer to have price, compares with the CuCr catalyzer, and this catalyst activity is high, environmental friendliness.
Adopt method provided by the invention; After catalyzer is through 450 ℃ of hydrogen reducings; In 100～140 ℃ of temperature of reaction, reaction pressure 0.1～5.0MPa, raw material (calculating 25% α, alpha-alpha-dimethyl benzylalcohol, 75% isopropyl benzene by weight percentage) liquid phase volume air speed is 1.0～3.0h
-1, hydrogen/α, alpha-alpha-dimethyl benzylalcohol volume are applied to α under 100～400 the reaction conditions; Alpha-alpha-dimethyl benzylalcohol hydrogenolysis generates the isopropyl benzene process, α, and alpha-alpha-dimethyl benzylalcohol transformation efficiency can reach 100%; Generate the isopropyl benzene selectivity and can reach more than 98%, obtained the good technical effect.
Through embodiment the present invention is done further elaboration below.
Embodiment
[embodiment 1]
Claim that 10.0g pseudo-boehmite powder adds in the 100.0g water, add the 2.0g concentrated nitric acid, peptization 24h under 70 ℃ of conditions gets alumina sol.Get 23.4g basic nickel carbonate and 100.0g ammoniacal liquor adding 100.0g water preparation nickel ammino and close solution.The nickel ammino is closed solution join in the aluminium colloidal sol, add sodium carbonate regulator solution pH and be 9 and aging 12h, then 70～120 ℃ of following thermal degradation 12 hours, through washing, filtration, dry catalyzer precursor.Adopting incipient impregnation to get method will be by 5.0gMg (NO
3)
26H
2The solution impregnation that O and 20.0g water are made into is on this presoma, and obtaining weight percent through roasting is 30%NiO-5%MgO-65%Al
2O
3Catalyzer.This catalyzer through 450 ℃ of hydrogen reducings after, adopt in weight percent α, alpha-alpha-dimethyl benzylalcohol content is 25.0%, isopropyl benzene content is 75.0% to be raw material, is 0.1MPa in reaction pressure, H
2/ α, the volume ratio 400 of alpha-alpha-dimethyl benzylalcohol, liquid stock phase volume air speed is 4.0h
-1Reaction conditions under estimate the visible table 2 of hydrogenolysis result.
[embodiment 2～10]
Catalyzer 2～10 prepares catalyzer according to each step among the embodiment 1, just changes each material composition, preparation condition, and wherein Preparation of catalysts condition and material composition is seen table 1, and the hydrogenolysis evaluation result is seen table 2.
The composition of each catalyzer of table 1 and preparation condition
[comparative example 1]
The CuCr catalyzer, composition is by weight percentage: 30.0%CuO-70.0%Cr
2O
3, adopting the mixing solutions and the preparation of sodium carbonate solution coprecipitation method of SRM 935a and cupric nitrate, synthesis program is identical with embodiment 1.
The CuCr catalyzer adopts and counts 5%H with volume percent in the comparative example
2-95%N
2Gas mixture 230 ℃ down reduction be used for hydrogenolysis after 12 hours.Appreciation condition:
The α of table 2 different catalysts, alpha-alpha-dimethyl benzylalcohol (benzylalcohol) hydrogenolysis performance
Select catalyzer 3 for use, just change different examination conditions, reaction 168h, its reaction result is listed in table 3.
α under the table 3 differential responses condition, alpha-alpha-dimethyl benzylalcohol hydrogenation catalyst evaluation result
From table 2,3 can find out, this technology is applied to produce isopropyl benzene and has obtained good reaction result, are 2.0～6.0h at 100～150 ℃ of temperature of reaction, reaction pressure 1.0～4.0Mpa, raw material volume space velocity
-1, behind the reaction 168h, activity of such catalysts and selectivity remain unchanged basically; α, the copper-based catalysts of the selectivity ratios prior art for preparing of the transformation efficiency of alpha-alpha-dimethyl benzylalcohol and isopropyl benzene increases, and compares with noble metal catalyst; This catalyzer price is low; This catalyst activity is high simultaneously, does not contain the Cr element, environmental friendliness.
Claims (6)
1. method of producing isopropyl benzene, with hydrogen and α, alpha-alpha-dimethyl benzylalcohol is raw material; With the isopropyl benzene is solvent, hydrogen/α, and the volume ratio of alpha-alpha-dimethyl benzylalcohol is 100～500: 1; Temperature of reaction is 100～180 ℃, and reaction pressure is 0.1～5.0MPa, and the liquid phase volume air speed is 1.0～10.0h
-1Under the condition, raw material contacts with catalyzer, and reaction generates isopropyl benzene and water, obtains the isopropyl benzene product through separation, and wherein catalyst system therefor comprises following component by weight percentage: a) 10.0～45.0%NiO; B) 45.0～75.0%Al
2O
3C) 3.0～15.0% be selected from MgO, CaO, BaO or ZrO
2In at least a.
2. the method for production isopropyl benzene according to claim 1 is characterized in that by weight percentage the NiO consumption is 15.0～30.0% in the catalyzer.
3. the method for production isopropyl benzene according to claim 1 is characterized in that the liquid phase volume air speed is 2.0～6.0h
-1, hydrogen/α, the volume ratio of alpha-alpha-dimethyl benzylalcohol counts 200～400: 1.
4. the method for production isopropyl benzene according to claim 1 is characterized in that in the said liquid phase feed α by weight percentage, and alpha-alpha-dimethyl benzylalcohol content is 20～40%, and isopropyl benzene content is 60～80%.
5. the method for production isopropyl benzene according to claim 1 is characterized in that said temperature of reaction is 110～150 ℃; Reaction pressure is 1.0～3.0MPa.
6. the method for production isopropyl benzene according to claim 1 is characterized in that being selected from by weight percentage MgO, CaO, BaO or ZrO
2In at least a consumption be 5.0～10.0%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110101090XA CN102746100A (en) | 2011-04-20 | 2011-04-20 | Preparation method of cumene |
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|---|---|---|---|
| CN201110101090XA CN102746100A (en) | 2011-04-20 | 2011-04-20 | Preparation method of cumene |
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| CN102746100A true CN102746100A (en) | 2012-10-24 |
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ID=47026662
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104230641A (en) * | 2013-06-17 | 2014-12-24 | 中国石油化工股份有限公司 | Production method of isopropyl benzene |
| CN104230640A (en) * | 2013-06-17 | 2014-12-24 | 中国石油化工股份有限公司 | Alpha, alpha-dimethylbenzyl alcohol hydrogenolysis method for preparing isopropyl benzene |
| CN112679294A (en) * | 2019-10-17 | 2021-04-20 | 中国石油化工股份有限公司 | Preparation method and application of isopropyl benzene |
| CN113070060A (en) * | 2020-01-03 | 2021-07-06 | 万华化学集团股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis of alpha-dimethyl benzyl alcohol and preparation method and application thereof |
| CN113121298A (en) * | 2019-12-31 | 2021-07-16 | 中国石油化工股份有限公司 | Method for producing isopropyl benzene |
| CN114042460A (en) * | 2021-11-16 | 2022-02-15 | 万华化学集团股份有限公司 | Catalyst for hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| EP3984984A4 (en) * | 2019-08-09 | 2023-07-19 | Sumitomo Chemical Company, Limited | Method for producing cumene |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104230641A (en) * | 2013-06-17 | 2014-12-24 | 中国石油化工股份有限公司 | Production method of isopropyl benzene |
| CN104230640A (en) * | 2013-06-17 | 2014-12-24 | 中国石油化工股份有限公司 | Alpha, alpha-dimethylbenzyl alcohol hydrogenolysis method for preparing isopropyl benzene |
| CN104230641B (en) * | 2013-06-17 | 2015-12-23 | 中国石油化工股份有限公司 | Produce the method for isopropyl benzene |
| EP3984984A4 (en) * | 2019-08-09 | 2023-07-19 | Sumitomo Chemical Company, Limited | Method for producing cumene |
| US11912638B2 (en) | 2019-08-09 | 2024-02-27 | Sumitomo Chemical Company, Limited | Method for producing cumene |
| CN112679294A (en) * | 2019-10-17 | 2021-04-20 | 中国石油化工股份有限公司 | Preparation method and application of isopropyl benzene |
| CN112679294B (en) * | 2019-10-17 | 2023-05-02 | 中国石油化工股份有限公司 | Preparation method and application of isopropylbenzene |
| CN113121298A (en) * | 2019-12-31 | 2021-07-16 | 中国石油化工股份有限公司 | Method for producing isopropyl benzene |
| CN113070060A (en) * | 2020-01-03 | 2021-07-06 | 万华化学集团股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis of alpha-dimethyl benzyl alcohol and preparation method and application thereof |
| CN114042460A (en) * | 2021-11-16 | 2022-02-15 | 万华化学集团股份有限公司 | Catalyst for hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| CN114042460B (en) * | 2021-11-16 | 2023-06-02 | 万华化学集团股份有限公司 | Catalyst for hydrogenolysis of alpha, alpha-dimethylbenzyl alcohol |
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Application publication date: 20121024 |