CN101735004A - Method for producing isopropylbenzene by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol - Google Patents
Method for producing isopropylbenzene by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol Download PDFInfo
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- CN101735004A CN101735004A CN200810043968A CN200810043968A CN101735004A CN 101735004 A CN101735004 A CN 101735004A CN 200810043968 A CN200810043968 A CN 200810043968A CN 200810043968 A CN200810043968 A CN 200810043968A CN 101735004 A CN101735004 A CN 101735004A
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Abstract
The invention relates to a method for producing isopropylbenzene by the hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol, which mainly solves the problems of environmental pollution of a chromium-containing catalyst system in the traditional hydrogenolysis production of the alpha, alpha-dimethyl benzyl alcohol, higher reaction temperature and pressure, large energy consumption and power consumption and corrosion of an additive to equipment. The invention better solves the problems by adopting the technical scheme that the catalytic hydrogenolysis of the alpha, alpha-dimethyl benzyl alcohol is carried out to convert the raw material of the alpha, alpha-dimethyl benzyl alcohol after alkali wash into the isopropylbenzene by hydrogen gas and a bifunctional catalyst containing Pd or Pd-Pt metal under the conditions that the temperature is 80-200 DEG C and the hydrogen pressure calculated by the gage pressure is 0.1-2.0MPa. The invention can be used for the industrial production of the isopropylbenzene prepared by the hydrogenolysis of the alpha, alpha-dimethyl benzyl alcohol.
Description
Technical field
The present invention relates to a kind of α, the method for alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene.
Background technology
Propylene oxide is a kind of important petrochemical complex organic raw material.At present, the main production method of propylene oxide is chlorohydrination and conjugated oxidation (as the trimethyl carbinol, ethylbenzene).Conjugated oxidation is that the employing organo-peroxide is that oxygenant is with third rare propylene oxide that is oxidized to.Traditional trimethyl carbinol and ethylbenzene conjugated oxidation, though can avoid investing the advantage of the chlorohydrination of high and long flow path to the severe contamination of environment, but also there is its shortcoming, have a large amount of coproduction by products in its process and generate, thereby make the production cost of propylene oxide can be subjected to the influence of the price volalility of co-product.The investment of joint process greatly also is its main shortcoming in addition.And be oxygen source with the hydrogen phosphide cumene, the by product dimethylphenylcarbinol of this process coproduction then can generate isopropyl benzene by catalytic hydrogenolysis.Isopropyl benzene can return the peroxidation unit process and obtain hydrogen phosphide cumene.With other co-oxidation technology ratio, it is short that isopropyl benzene co-oxidation process has operational path, and facility investment is few, advantages such as no co-product.
U.S. Pat 3337646 has proposed a kind of α, the method for alpha-alpha-dimethyl benzylalcohol phase hydrogenolysis preparing isopropylbenzene, and this technology is with Ni-Cr-Al
2O
3Be catalyzer, up to 350 ℃ of temperature of reaction, pressure is under the condition of 2.0MPa, can be with α, and alpha-alpha-dimethyl benzylalcohol phase hydrogenolysis is isopropyl benzene (boiling point of isopropyl benzene and benzylalcohol all is lower than 210 ℃).For the fixed catalyzed reaction, gas-phase reaction is than liquid phase reaction temperature height, thereby the gas-phase reaction energy consumption is also can corresponding increase many.And with respect to liquid phase reaction, gas-phase reaction will make the treatment capacity of reaction unit greatly reduce.Thereby, if under gas phase condition in order to realize satisfying the turnout of same products, will have to amass the treatment capacity that improves device, thereby will increase facility investment by the augmenting response body.Contain the Cr component in this catalyzer, have the problem of environmental pollution and harm.
The SUMITOMO CHEMICAL chemical patent US6646139B2 provide α, the continuous hydrogenolysis of alpha-alpha-dimethyl benzylalcohol catalysis prepares the technology of isopropyl benzene, and this technology is to be hydrogen source with hydrogen, and copper-chromated oxide is a catalyzer, reaction pressure 100～10000MPa, the temperature of this reaction system is up to 180～250 ℃.The boiling point of benzylalcohol has only 204 ℃, and the boiling point of isopropyl benzene is 145 ℃.Thereby under liquid-phase condition, carry out hydrogenolysis with the higher turnout of assurance device in order to keep reactant, and need apply than higher pressure, this will inevitably increase the power consumption of process.If reaction can be carried out, can obviously reduce reaction required power consumption and energy expenditure under lower temperature.And in the Cu-Cr catalyzer because of there being the Cr component, in Preparation of Catalyst and removal process, have problem of environmental pollution.
Chinese patent CN 1308273C has announced a kind of α, the method for alpha-alpha-dimethyl benzylalcohol liquid phase hydrogenolysis preparing isopropylbenzene.This method is to adopt batch operation, is catalyzer with the 2.0wt%Pd/ cocoanut active charcoal, the benzylalcohol hydrogenolysis can be converted into isopropyl benzene, α, the transformation efficiency 96～98% of alpha-alpha-dimethyl benzylalcohol, selectivity 99%.Will use monobasic low-carbon alcohol solvent and additives (having) such as formic acid, acetate and halohydrocarbon in this technology, it can reach 20～150% of benzylalcohol consumption by weight percentage with total amount.This technical matters adopts batch operation, and production efficiency is lower.But also introduce binder components such as a large amount of monoprotic acid, halohydrocarbon, and not only improved the later separation cost and whole catalytic hydrogenolysis cost of isopropyl benzene, also be unfavorable for the raising of isopropyl benzene purity, and cause equipment corrosion serious, improved facility investment.
In sum, existing α, alpha-alpha-dimethyl benzylalcohol hydrogenolysis prepares to exist in the isopropyl benzene technology and contains the Cr catalyzer and exist environmental pollution, temperature of reaction and pressure higher, and the big and catalyst based solvent additive of Pd of energy consumption and power consumption is to problems such as equipment corrosions.
Summary of the invention
Technical problem to be solved by this invention is existing α, exist to use in the alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene technology that to contain that there is environmental pollution in the Cr catalyzer, temperature of reaction is higher higher with pressure, the problem that energy consumption and power consumption are big, provide a kind of new α, the method for alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene.This method has that catalyzer forms that environmental pollution is little, temperature of reaction is lower, pressure is lower, energy consumption and the lower advantage of power consumption.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of α, alpha-alpha-dimethyl benzylalcohol catalytic hydrogenolysis is produced the method for isopropyl benzene, with α, alpha-alpha-dimethyl benzylalcohol hydrocarbon material and hydrogen are raw material, raw material is fed the hydrogenolysis district, is that 60～250 ℃, reaction pressure are that the volume space velocity of 0.1～4.0MPa, hydrocarbon raw material is 0.2～20 hour in temperature of reaction
-1, α in hydrogen/hydrocarbon raw material, the mol ratio of alpha-alpha-dimethyl benzylalcohol is under 1～30: 1 the condition, raw material and catalyzer contact reacts generate isopropyl benzene;
Wherein used catalyzer comprises following component in parts by weight: 1) 0.005～5.0 part of metal or hopcalite that is selected to Pd or Pd and Pt; 2) 95～99.995 parts are selected from least a in aluminum oxide, amorphous silicon aluminium or the Zeolite support.
In the technique scheme, the volume space velocity preferable range that feeds hydrogenolysis district hydrocarbon raw material is 0.5～15 hour
-1, the α in hydrogen/hydrocarbon raw material, alpha-alpha-dimethyl benzylalcohol is 1～20: 1 with the preferable range of molar ratio computing.The preferable range of temperature of reaction is 80～200 ℃, and the preferable range of reaction pressure is 0.1～2.0MPa.After reaction finished, lock out operation can obtain isopropyl benzene through dewatering.
The metal of Pd described in the technique scheme or Pd and Pt or hopcalite consumption are 0.01～1.0 part in the parts by weight preferable range.Selected carrier described in the technique scheme is at least a in aluminum oxide, amorphous silicon aluminium, mordenite, zeolite beta, ZSM-5 or the Y zeolite.
Preparation of catalysts method of the present invention is as follows: na-pretreated zeolite and ammonium salt solution are carried out ion-exchange, carry out roasting after the exchange and be converted into h-type zeolite.Pinch moulding with h-type zeolite and required pseudo-boehmite, sesbania powder and dilute nitric acid solution are wet then, obtain support of the catalyst through drying and roasting.And amorphous aluminum silicide, aluminum oxide can be directly and the moulding of pseudo-boehmite binding agent.On carrier, introduce the hydrogenation metal component by ion-exchange or dipping method.The dipping of Pd, Pt component or exchange solution can be Palladous chlorides, Palladous nitrate, and ammonium palladic chloride, ammonium palladous chloride, platinum nitrate, Platinic chloride, ammonium chloroplatinate, ammonium chloroplatinite, dichloro four ammoniums close at least a aqueous solution of platinum.After introducing hydrogenation component on the carrier of moulding, under less than 200 ℃, carry out drying, at 300～600 ℃ dried catalyzer is calcined then.Catalyzer is seated in the fixed-bed reactor through after pulverizing, and can obtain going back the catalyzer of ortho states after activation under the atmosphere of hydrogen, and this catalyzer can be directly used in α, the hydrogenolysis process of alpha-alpha-dimethyl benzylalcohol.
According to the present invention, described hydrogenolysis uses to have stronger acid site and carries out with aluminum oxide, zeolite or amorphous silicon aluminium-based catalyst than the peracid amount, the zeolite of the acid carrier of catalyzer or unbodied form are used, and described zeolite is selected from mordenite, BETA zeolite, ZSM-5 zeolite and y-type zeolite and their mixture that the aperture is 5～9 dusts.
In the hydrogenolysis process of benzylalcohol, can on acid sites, produce the alpha-methyl styrene intermediate, should make the saturated generation isopropyl benzene of its hydrogenation cause catalyst deactivation to prevent the alpha-methyl styrene polymerization from impelling coke to form rapidly.Therefore, the acidic site of catalyzer and hydrogenation sites should well be mated.The acid site of catalyzer can be regulated by the silicone content of aluminum oxide, amorphous silicon aluminium or the silicone content of Zeolite support, and the hydrogenation activity at hydrogenation metal center can be adjusted by the charge capacity of metal, the dispersity of loaded metal.
It is bigger that catalyzer of the present invention has higher, the sour amount of acidity, and specific surface is bigger, the scattered and active high characteristics of hydrogenolysis of surface metal hydrogenation component.When the process of the isopropyl benzene material hydrogenolysis preparing isopropylbenzene that is used to contain benzylalcohol, have good activity and selectivity.
The present invention relates to a kind of α, the method for alpha-alpha-dimethyl benzylalcohol material preparing isopropylbenzene by catalytic hydrogenolysis.This technology is with hydrogen and α, alpha-alpha-dimethyl benzylalcohol is raw material, the benzylalcohol raw material is being 80～200 ℃ with temperature, hydrogen pressure under the condition of gauge pressure 0.1～2.0MPa with contain the metal of Pd or Pt and Pd or the dual-function catalyst of hopcalite is used for α, alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene process, make and saved the Cr element in the catalyzer, reduced pollution to environment, in addition, because reaction can be 80～160 ℃ of operations down, pressure can be operated under 0.1～2.0MPa, therefore temperature of reaction is low, and reaction pressure is low, and energy consumption is low, and α, the transformation efficiency of alpha-alpha-dimethyl benzylalcohol surpasses 99.5%, and the selectivity of isopropyl benzene has obtained technical result preferably greater than 99.5%.
The present invention is further elaborated below by embodiment.
Embodiment
[embodiment 1]
With 100 gram pseudo-boehmites, mix with 3.5 gram sesbania powder, add then rare nitric acid wet pinch, moulding, 600 ℃ of following roastings obtain carrier in drying, the air atmosphere.Take by weighing the baked alumina supporter of 20 grams, flood required H
2PdCl
4Behind the solution, drying obtains Pd content and counts 0.3 part Pd/Al with parts by weight after the roasting
2O
3Catalyzer a.
[embodiment 2]
Take by weighing 70 gram SiO
2-Al
2O
3(SiO
2Weight content 26.0%) powder, with 41.7 gram pseudo-boehmites, 3.5 gram sesbania powder mix the back add rare nitric acid wet pinch, moulding, 600 ℃ of following roastings obtain carrier in drying, the air atmosphere then.Take by weighing the baked sial base carrier of 20 grams, with required Pd (NH
3)
4Cl
2The aqueous solution carry out ion-exchange after, obtain Pd content after drying, the roasting and count 0.3 part Pd/SiO with parts by weight
2-Al
2O
3Catalyzer b.
[embodiment 3]
Take by weighing 100 gram NaMOR zeolite (MOR is a mordenite) powder, exchange the HMOR zeolite that twice back drying, roasting obtain Hydrogen with ammonium nitrate solution.Take by weighing 70 gram HMOR, with 41.7 gram alumina powders, 3.5 gram sesbania powder mix the back add rare nitric acid wet pinch, moulding, 550 ℃ of following roastings obtain the HMOR Zeolite support in drying, the air atmosphere then.Take by weighing 20 gram HHMOR Zeolite supports, with required Pd (NH
3)
4Cl
2, Pt (NH
3)
4Cl
2After mixing solutions carried out ion-exchange, drying obtained Pd, Pt content and counts the Pd-Pt/MOR catalyzer c that is 0.5 part with parts by weight after the roasting.
[embodiment 4]
Take by weighing 100 gram NaZSM-5 zeolite powders, exchange the H ZSM-5 zeolite that twice back drying, roasting obtain Hydrogen with ammonium nitrate solution.Take by weighing 70 gram HZSM-5, with 41.7 gram alumina powders, 3.5 gram sesbania powder mix the back add rare nitric acid wet pinch, moulding, 550 ℃ of following roastings obtain the HZSM-5 Zeolite support in drying, the air atmosphere then.Take by weighing 20 gram HZSM-5 Zeolite supports, flood required Pd (NH
3)
4Cl
2Behind the aqueous solution, drying obtains Pd content and counts 0.5 part Pd/ZSM-5 catalyzer d with parts by weight after the roasting.
[embodiment 5]
Take by weighing 100 gram NaBETA zeolite powders, exchange the HBETA zeolite that twice back drying, roasting obtain Hydrogen with ammonium nitrate solution.Take by weighing 70 gram HBETA, with 41.7 gram alumina powders, 3.5 gram sesbania powder mix the back add rare nitric acid wet pinch, moulding, 550 ℃ of following roastings obtain the HBETA Zeolite support in drying, the air atmosphere then.Take by weighing 20 gram HBETA Zeolite supports, flood required H
2PdCl
4Behind the solution, drying obtains Pd content and counts 0.05 part Pd/BETA catalyzer e with parts by weight after the roasting.
[embodiment 6]
Take by weighing the NaY zeolite powder, exchange the HY zeolite that twice back drying, roasting obtain Hydrogen with ammonium nitrate solution.Take by weighing 70 gram HY, with 41.7 gram alumina powders, 3.5 gram sesbania powder mix the back add rare nitric acid wet pinch, moulding, 550 ℃ of following roastings obtain the HY Zeolite support in drying, the air atmosphere then.Take by weighing 20 gram HY zeolites, with required Pd (NH
3)
4Cl
2After solution carried out ion-exchange, drying obtained after the roasting counting 0.3 part of Pd/HY catalyzer f with parts by weight.
[comparative example 1]
Cu-Cr catalyzer (mol ratio of Cu: Cr is 1: 1) is that raw material adopts the coprecipitation method preparation with ammonium Bicarbonate Food Grade and cupric nitrate, and roasting obtains the Cu-Cr catalyzer in precipitation drying, the air atmosphere.
[comparative example 2]
Cu-Zn catalyzer (mol ratio of Cu: Cr is 1: 1) is a raw material with the nitrate of Cu, Zn, Na
2CO
3For precipitation agent adopts the coprecipitation method preparation, roasting obtains the Cu-Zn catalyzer in precipitation drying, the air atmosphere.
Use is reacted examination by above-mentioned catalyzer a～f that makes and Comparative Examples catalyzer, consists of isopropyl benzene content 75.0% in the weight percentage reaction raw materials, benzylalcohol content 25.0%, and at fixed-bed reactor, reaction result is listed in table 1:
Table 1 catalyst performance result
| Catalyzer | ??a | ??b | ??c | ??d | ??e | ??f | Comparative example 1 | Comparative example 2 |
| Temperature of reaction/℃ | ??160 | ??140 | ??100 | ??120 | ??130 | ??130 | ??220 | ??240 |
| Reaction pressure/MPa | ??0.1 | ??0.1 | ??2.0 | ??2.0 | ??1.0 | ??1.8 | ??1.8 | ??0.1 |
| LHSV/ hour -1 | ??1.5 | ??1.5 | ??15.0 | ??10.0 | ??7.5 | ??10.0 | ??1.5 | ??1.5 |
| ??H 2/ α, alpha-alpha-dimethyl benzylalcohol (moles/mole) | ??4.0 | ??8.0 | ??15.0 | ??10 | ??10.0 | ??10.0 | ??8.0 | ??8.0 |
| α, the transformation efficiency of alpha-alpha-dimethyl benzylalcohol (%) | ??99.7 | ??99.6 | ??99.6 | ??99.7 | ??99.7 | ??99.9 | ??99.1 | ??67.0 |
| Isopropyl benzene selectivity (%) | ??99.8 | ??99.7 | ??99.8 | ??99.8 | ??99.6 | ??99.7 | ??99.4 | ??93.0 |
From last table as seen, catalyzer a～f does not contain the Cr element, has reduced the pollution to environment, in addition, because reaction can be 80～160 ℃ of operations down, pressure can be operated under 0.1～2.0MPa, therefore to have temperature of reaction low for this technology, and reaction pressure is low, advantage of low energy consumption; α, the transformation efficiency of alpha-alpha-dimethyl benzylalcohol surpasses 99.5%, and the selectivity of isopropyl benzene has obtained technical result preferably greater than 99.5%.
Claims (4)
1. α, the method of alpha-alpha-dimethyl benzylalcohol producing isopropylbenzene by hydrogenolysis, to contain α, alpha-alpha-dimethyl benzylalcohol hydrocarbon material and hydrogen are raw material, raw material is fed the hydrogenolysis district, is that 60～250 ℃, reaction pressure are that the volume space velocity of 0.1～4.0MPa, hydrocarbon material is 0.2～20 hour in temperature of reaction
-1, the α in hydrogen/hydrocarbon raw material, the mol ratio of alpha-alpha-dimethyl benzylalcohol is under 1～30: 1 the condition, raw material and the formation reaction of catalyzer contact reacts generate isopropyl benzene;
Wherein used catalyzer comprises following component in parts by weight: 1) 0.005～5.0 part of metal or oxide mixture that is selected from Pd or Pd and Pt; 2) 95～99.995 parts are selected from least a in aluminum oxide, amorphous silicon aluminium or the Zeolite support.
2. α according to claim 1, the method for alpha-alpha-dimethyl benzylalcohol producing isopropylbenzene by hydrogenolysis, the volume space velocity that it is characterized in that described hydrocarbon material is 0.5～15 hour
-1, the α in hydrogen/hydrocarbon raw material, alpha-alpha-dimethyl benzylalcohol ratio be 1～20: 1 with mol ratio.
3. α according to claim 1, the method for alpha-alpha-dimethyl benzylalcohol producing isopropylbenzene by hydrogenolysis is characterized in that temperature of reaction is 80～200 ℃, reaction pressure is 0.1～2.0MPa.
4. α according to claim 1, the method for alpha-alpha-dimethyl benzylalcohol producing isopropylbenzene by hydrogenolysis is characterized in that the metal of Pd or Pd and Pt or the consumption of oxide mixture are 0.01～1.0 part.
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| CN102746100A (en) * | 2011-04-20 | 2012-10-24 | 中国石油化工股份有限公司 | Preparation method of cumene |
| CN104230642A (en) * | 2013-06-17 | 2014-12-24 | 中国石油化工股份有限公司 | Alpha, alpha-dimethyl-benzyl carbinol direct hydrogenolysis method for preparing 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 |
| CN109096031A (en) * | 2017-06-21 | 2018-12-28 | 中国石油化工股份有限公司 | The production method of isopropylbenzene |
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|---|---|---|---|---|
| CN1308273C (en) * | 2004-09-27 | 2007-04-04 | 华东理工大学 | Process for preparing isopropyl benzene by catalytically hydrogenolysis alpha, alpha dimethyl benzyl alcohol |
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| CN114433076A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Supported hydrogenolysis catalyst and preparation method and application thereof |
| CN114433076B (en) * | 2020-10-16 | 2024-02-02 | 中国石油化工股份有限公司 | Supported hydrogenolysis catalyst and preparation method and application thereof |
| WO2023070262A1 (en) * | 2021-10-25 | 2023-05-04 | 万华化学集团股份有限公司 | DEVICE AND METHOD FOR PRODUCING CUMENE BY HYDROGENOLYSIS OF α,α-DIMETHYLBENZYL ALCOHOL |
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