CN106431809A - Synthesis method of ethylbenzene - Google Patents

Synthesis method of ethylbenzene Download PDF

Info

Publication number
CN106431809A
CN106431809A CN201510492936.5A CN201510492936A CN106431809A CN 106431809 A CN106431809 A CN 106431809A CN 201510492936 A CN201510492936 A CN 201510492936A CN 106431809 A CN106431809 A CN 106431809A
Authority
CN
China
Prior art keywords
benzene
reactor
ethyl acetate
catalyst
hydrogenation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201510492936.5A
Other languages
Chinese (zh)
Other versions
CN106431809B (en
Inventor
范文青
杨为民
王德举
刘仲能
韩亚梅
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
China Petroleum and Chemical Corp
Sinopec Shanghai Research Institute of Petrochemical Technology
Original Assignee
China Petroleum and Chemical Corp
Sinopec Shanghai Research Institute of Petrochemical Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by China Petroleum and Chemical Corp, Sinopec Shanghai Research Institute of Petrochemical Technology filed Critical China Petroleum and Chemical Corp
Priority to CN201510492936.5A priority Critical patent/CN106431809B/en
Publication of CN106431809A publication Critical patent/CN106431809A/en
Application granted granted Critical
Publication of CN106431809B publication Critical patent/CN106431809B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a synthesis method of ethylbenzene, and is used for mainly solving the technical problems of high raw material cost, long technological process and low efficiency in the prior art. The problems are relatively well solved by the technical scheme comprising that the synthesis method of ethylbenzene includes a hydrogenation reactor and an alkylation reactor and includes the following steps: (1) in the hydrogenation reactor, and in the presence of a hydrogenation catalyst, carrying out a hydrogenation reaction of hydrogen gas and ethyl acetate, to obtain a material flow I; (2) mixing the material flow I with benzene to obtain a material flow II; and (3) in the alkylation reactor, and in the presence of an alkylation catalyst, carrying out an alkylation reaction of the material flow II to obtain a material flow III containing ethylbenzene. The synthesis method can be applied in industrial production of ethylbenzene.

Description

The synthetic method of ethylbenzene
Technical field
The present invention relates to the synthetic method of ethylbenzene.
Background technology
Ethylbenzene is a kind of important industrial chemicals, is to produce the indispensable raw material of styrene, most of ethylbenzene is used for Produce styrene.And styrene is important basic organic chemical industry raw material, it is mainly used in polymeric material field poly- to produce Styrene and its copolymer.With auto industry, the fast-developing band of insulator industry, packaging industry and article of everyday use industry That comes is growing to styrene demand, and the ethylbenzene demand of China is also being continuously increased.
It is industrial that mainly by benzene, come synthesizing ethyl benzene, (concrete document has Chinese patent with ethylene generation alkylated reaction CN101993331A、CN102040458A).Petroleum as ethylene raw derives from oil, and with petroleum resources Day by day exhausted increasingly soaring with oil price, the production cost of China's ethylene steeply rises, by the ethylbenzene of benzene alkylation with ethylene Produce and be inherently restricted, need us to develop new approach and carry out synthesizing ethyl benzene.An approach therein is to adopt ethanol Come to replace ethylene as raw material for alkylation come with benzene react synthesizing ethyl benzene (concrete document have Chinese patent CN102276410A, CN102276411A).At present, China's acetass price will be less than ethanol, (concrete using acetass hydrogen addition technology ethanol Document has Chinese patent CN102976892A, CN101941887A), can be to be provided by the production of ethanol and benzene synthesizing ethyl benzene Feed ethanol, under the background of China's acetic acid industry production capacity surplus, also provides new growth for acetic acid industry downstream application Point.The ethyl acetate ethanol that obtains of hydrogenation again with two step technology paths of benzene alkylation synthesizing ethyl benzene although can be by acetic acid Ethyl ester carrys out synthesizing ethyl benzene as raw material for alkylation, but so will be to middle product ethanol after first step ethyl acetate hydrogenation Carry out separate transport and storage, flow process is longer, energy consumption and discharge are high.During modern chemical industry produces, by reactors in series Mode is carried out continuously making multistep reaction be coupling in, can eliminate the separation of intermediate product and storage, simplification of flowsheet, Reducing energy consumption and discharge, develop skill economy.Therefore, make use of production capacity surplus and cheap ethyl acetate as alkyl Change raw material, coupling ethyl acetate preparation of ethanol by hydrogenating and benzene and two processes of ethanol alkylation ethylbenzene, be directly realized by by acetic acid Ethyl ester and benzene synthesizing ethyl benzene, mainly solve raw material for alkylation high cost, long flow path, inefficient in existing ethylbenzene synthetic technology Technical problem, can apply in the commercial production of ethylbenzene.At present, still not with regard to by coupled reaction come directly real Now by the relevant report of ethyl acetate and benzene synthesizing ethyl benzene method.
Content of the invention
The technical problem to be solved is to provide a kind of synthetic method of new ethylbenzene, and it is short-acting that the method has flow process The high feature of rate.
For solving above-mentioned technical problem, technical scheme is as follows:The synthetic method of ethylbenzene, including hydrogenation reactor And alkylation reactor, comprise the steps:
(1) in hydrogenation reactor, in the presence of a hydrogenation catalyst, hydrogen and ethyl acetate carry out hydrogenation reaction, obtain thing
Stream I;
(2) stream I and benzene are mixed to get stream I I;
(3) in alkylation reactor, in the presence of alkylation catalyst, stream I I occurs alkylated reaction to obtain containing second
Stream I II of benzene.
In technique scheme, described hydrogenation catalyst preferably includes carrier and active component;Described carrier is selected from two At least one in silicon oxide, titanium dioxide and aluminium oxide, more preferably silicon dioxide;Described active component is preferably wrapped Include following components:
Component 1:Gallium or its oxide;
Component 2:The corresponding simple substance of at least one element of VIII race or its oxide in the periodic table of elements;More preferably VIII race The corresponding simple substance of at least two elements or its oxide;Such as but not limited to, described VIII race's element at least includes Ni and Pd, Now described two VIII race's elements have synergism in terms of improving ethylbenzene yield;
Component 3:The corresponding simple substance of at least one element of II B race or its oxide in the periodic table of elements;
Component 4:The corresponding simple substance of at least one element of group of the lanthanides or its oxide in the periodic table of elements;
In parts by weight, molecular sieve:Component 1:Component 2:Component 3:Component 4 is 100:(1~15):(1~30):(1~10):(1~5).
In technique scheme, described II B race element preferably includes at least one element of Zn element.
In technique scheme, described lanthanide series preferably include at least one element of Ce element.
In technique scheme, described alkylation catalyst is preferably molecular sieve, including ZSM-5, Beta molecular sieve, MCM-22, At least one in Y molecular sieve and modified ZSM-5, Beta molecular sieve, MCM-22, Y molecular sieve, more preferably preferential ZSM-5 Molecular sieve and modified ZSM-5 molecular sieve.
In technique scheme, described molecular sieve is preferably hydrogen type molecular sieve.
In technique scheme, hydrogenation reaction pressure and/or alkylated reaction pressure are preferably 2~3MPa.
In technique scheme, hydrogenation reaction temperature is preferably 200~260 DEG C
In technique scheme, in hydrogenation reactor charging, hydrogen and the mol ratio of ethyl acetate are preferably 20~50.
In technique scheme, the liquid volume air speed of ethyl acetate is preferably 0.3~0.9h-1.The liquid bulk of ethyl acetate Long-pending air speed is with respect to hydrogenation catalyst volume metering.
In technique scheme, alkylated reaction temperature is preferably 300~400 DEG C.
In technique scheme, the liquid volume air speed of benzene is preferably 2~8h-1.The liquid volume air speed of benzene is with respect to alkyl Change the volume metering of catalyst.
In technique scheme, described hydrogenation catalyst preferably employ infusion process preparation, described infusion process preferably include as Lower step:The soluble-salt of gallium element, VIII race's element, II B race element and lanthanide series is made into aqueous solution, common dipping Molecular sieve, reduction.
In technique scheme, described reduction is carried out using the atmosphere of hydrogen;The temperature of reduction is preferably 500~700 DEG C.
In technique scheme, the atmosphere of described hydrogen, can be pure hydrogen, but for reduction process and relaxes behaviour Make safety or hydrogen with described reducing condition be in chemically inert those become gas phase material composition mixture. Under described reducing condition be in chemically inert those become the material of gas phases preferably be selected from nitrogen, helium, neon, in argon extremely Few one kind.In examples and comparative examples of the present invention the atmosphere of involved hydrogen be hydrogeneous with volume percentage The hydrogen nitrogen mixture of gas 5%.
Heretofore described pressure refers both to gauge pressure.
Wherein, ethyl acetate conversion ratio, Computer Corp. of benzene conversion ratio and ethylbenzene yield is as follows:
Using the above-mentioned method by ethyl acetate and benzene synthesizing ethyl benzene, under preferred reaction condition, the yield of ethylbenzene is 89.4%, achieve preferable technique effect.And not adopting the scheme of sectional feeding, ethyl acetate, benzene and hydrogen are all When one reactor feeds jointly, ethylbenzene yield is relatively low.
Below by embodiment, the present invention is further elaborated, but these embodiments are not that the scope of the present invention is carried out Limit.
Specific embodiment
【Embodiment 1】
1. catalyst preparation
(1) hydrogenation catalyst:(molecular formula is Ga (NO to weigh 9.58g Ganite (Fujisawa).3)3·9H2O), 4.96g nickel nitrate (divides Minor is Ni (NO3)2·6H2O), (molecular formula is PdCl to 0.17g Palladous chloride.2), (molecular formula is 2.28g zinc nitrate Zn(NO3)2·6H2O), (molecular formula is Ce (NO to 0.93g cerous nitrate3)3·6H2O) 100mL water dissolution is used to form material I; Weigh 10g silicon dioxide to add in 50mL deionized water, stir 1h, form material II;Material I is added to thing In material II, impregnate 4h, 120 DEG C are dried overnight, reductase 12 h in the atmosphere of 600 DEG C of hydrogen, last tabletting is pulverized, The granule choosing 20~40 mesh is standby.The composition of catalyst in parts by weight, silicon dioxide:Gallium element:Nickel element:Palladium element: Zinc element:Ce elements are 100:8:10:1:5:3, it is labeled as 8Ga-10Ni-1Pd-5Zn-3Ce.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Ethyl acetate and benzene synthesizing ethyl benzene are carried out on the continuous fixed bed reactor of two series connection, and hydrogenation catalyst fills Fill out in first reactor, alkylation catalyst is seated in second reactor, two catalyst in reactor fillings Volume is 5mL, and, in first reactor feed, benzene is in first reactor and second reaction for hydrogen and ethyl acetate Feed between device, the logistics that benzene is obtained with first reactor outlet enters back into reaction in second reactor after mixing.Instead The condition is answered to be:First reactor reaction temperature is 240 DEG C, and feed pressure is 2MPa, the liquid volume of ethyl acetate Air speed is 0.3h-1, feed hydrogen is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 400 DEG C, Feed pressure is 2MPa, and the liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 18:1. Reaction result is shown in Table 1.
【Embodiment 2】
1. catalyst preparation
(1) hydrogenation catalyst:(molecular formula is Ga (NO to weigh 11.99g Ganite (Fujisawa).3)3·9H2O), 7.43g nickel nitrate (divides Minor is Ni (NO3)2·6H2O), (molecular formula is PdCl to 0.17g Palladous chloride.2), (molecular formula is 2.73g zinc nitrate Zn(NO3)2·6H2O), (molecular formula is Ce (NO to 0.93g cerous nitrate3)3·6H2O) 100mL water dissolution is used to form material I; Weigh 10g silicon dioxide to add in 50mL deionized water, stir 1h, form material II;Material I is added to thing In material II, impregnate 4h, 120 DEG C are dried overnight, reductase 12 h in the atmosphere of 600 DEG C of hydrogen, last tabletting is pulverized, The granule choosing 20~40 mesh is standby.The composition of catalyst in parts by weight, silicon dioxide:Gallium element:Nickel element:Palladium element: Zinc element:Ce elements are 100:8:10:1:5:3, it is labeled as 10Ga-15Ni-1Pd-6Zn-3Ce.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Ethyl acetate and benzene synthesizing ethyl benzene are carried out on the continuous fixed bed reactor of two series connection, and hydrogenation catalyst fills Fill out in first reactor, alkylation catalyst is seated in second reactor, two catalyst in reactor fillings Volume is 5mL, and benzene feeds between first reactor and second reactor.Reaction condition is:First reaction Device reaction temperature is 240 DEG C, and feed pressure is 2MPa, and the liquid volume air speed of ethyl acetate is 0.3h-1, feed hydrogen Gas is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 400 DEG C, and feed pressure is 2MPa, The liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 18:1.Reaction result is shown in Table 1.
【Embodiment 3】
1. catalyst preparation
(1) hydrogenation catalyst:(molecular formula is Ga (NO to weigh 9.58g Ganite (Fujisawa).3)3·9H2O), 5.45g nickel nitrate (divides Minor is Ni (NO3)2·6H2O), (molecular formula is Zn (NO to 2.28g zinc nitrate3)2·6H2O), 0.93g cerous nitrate (divides Minor is Ce (NO3)3·6H2O) 100mL water dissolution is used to form material I;Weighing 10g silicon dioxide adds 50mL to go In ionized water, stir 1h, form material II;Material I is added in material II, impregnates 4h, 120 DEG C dried Night, reductase 12 h in the atmosphere of 600 DEG C of hydrogen, last tabletting is pulverized, and the granule choosing 20~40 mesh is standby.Catalyst Composition in parts by weight, silicon dioxide:Gallium element:Nickel element:Zinc element:Ce elements are 100:8:11:5:3, it is labeled as 8Ga-11Ni-5Zn-3Ce.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Ethyl acetate and benzene synthesizing ethyl benzene are carried out on the continuous fixed bed reactor of two series connection, and hydrogenation catalyst fills Fill out in first reactor, alkylation catalyst is seated in second reactor, two catalyst in reactor fillings Volume is 5mL, and benzene feeds between first reactor and second reactor.Reaction condition is:First reaction Device reaction temperature is 240 DEG C, and feed pressure is 2MPa, and the liquid volume air speed of ethyl acetate is 0.3h-1, feed hydrogen Gas is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 400 DEG C, and feed pressure is 2MPa, The liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 18:1.Reaction result is shown in Table 1.
【Embodiment 4】
1. catalyst preparation
(1) hydrogenation catalyst:(molecular formula is Ga (NO to weigh 9.58g Ganite (Fujisawa).3)3·9H2O), 1.83g Palladous chloride. (divides Minor is PdCl2), 2.28g zinc nitrate (molecular formula be Zn (NO3)2·6H2O), (molecular formula is 0.93g cerous nitrate Ce(NO3)3·6H2O) 100mL water dissolution is used to form material I;Weigh 10g silicon dioxide and add in 50mL deionized water, Stirring 1h, forms material II;Material I is added in material II, impregnates 4h, 120 DEG C are dried overnight, 600 DEG C Reductase 12 h in the atmosphere of hydrogen, last tabletting is pulverized, and the granule choosing 20~40 mesh is standby.The composition of catalyst is with weight Amount part meter, silicon dioxide:Gallium element:Palladium element:Zinc element:Ce elements are 100:8:11:5:3, it is labeled as 8Ga-11Pd-5Zn-3Ce.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Ethyl acetate and benzene synthesizing ethyl benzene are carried out on the continuous fixed bed reactor of two series connection, and hydrogenation catalyst fills Fill out in first reactor, alkylation catalyst is seated in second reactor, two catalyst in reactor fillings Volume is 5mL, and benzene feeds between first reactor and second reactor.Reaction condition is:First reaction Device reaction temperature is 240 DEG C, and feed pressure is 2MPa, and the liquid volume air speed of ethyl acetate is 0.3h-1, feed hydrogen Gas is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 400 DEG C, and feed pressure is 2MPa, The liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 18:1.Reaction result is shown in Table 1.
【Embodiment 5】
1. catalyst preparation
(1) hydrogenation catalyst:(molecular formula is Ga (NO to weigh 9.58g Ganite (Fujisawa).3)3·9H2O), 4.96g nickel nitrate (divides Minor is Ni (NO3)2·6H2O), (molecular formula is PdCl to 0.17g Palladous chloride.2), (molecular formula is 2.28g zinc nitrate Zn(NO3)2·6H2O), (molecular formula is La (NO to 0.94g Lanthanum (III) nitrate3)3·6H2O) 100mL water dissolution is used to form material I; Weigh 10g silicon dioxide to add in 50mL deionized water, stir 1h, form material II;Material I is added to thing In material II, impregnate 4h, 120 DEG C are dried overnight, reductase 12 h in the atmosphere of 600 DEG C of hydrogen, last tabletting is pulverized, The granule choosing 20~40 mesh is standby.The composition of catalyst in parts by weight, silicon dioxide:Gallium element:Nickel element:Palladium element: Zinc element:Lanthanum element is 100:8:10:1:5:3, it is labeled as 8Ga-10Ni-1Pd-5Zn-3La.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Ethyl acetate and benzene synthesizing ethyl benzene are carried out on the continuous fixed bed reactor of two series connection, and hydrogenation catalyst fills Fill out in first reactor, alkylation catalyst is seated in second reactor, two catalyst in reactor fillings Volume is 5mL, and benzene feeds between first reactor and second reactor.Reaction condition is:First reaction Device reaction temperature is 240 DEG C, and feed pressure is 2MPa, and the liquid volume air speed of ethyl acetate is 0.3h-1, feed hydrogen Gas is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 400 DEG C, and feed pressure is 2MPa, The liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 18:1.Reaction result is shown in Table 1.
【Embodiment 6】
1. catalyst preparation
(1) hydrogenation catalyst:Prepare hydrogenation catalyst according to the same manner as in Example 1.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Investigate ethyl acetate and the reactivity worth of benzene synthesizing ethyl benzene according to the same manner as in Example 1.Reaction condition is:The One reactor reaction temperature is 250 DEG C, and feed pressure is 2MPa, and the liquid volume air speed of ethyl acetate is 0.6h-1, Feed hydrogen is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 400 DEG C, and feed pressure is 2 MPa, the liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 9:1.Reaction result is shown in Table 1.
【Embodiment 7】
1. catalyst preparation
(1) hydrogenation catalyst:Prepare hydrogenation catalyst according to the same manner as in Example 1.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Investigate ethyl acetate and the reactivity worth of benzene synthesizing ethyl benzene according to the same manner as in Example 1.Reaction condition is:The One reactor reaction temperature is 230 DEG C, and feed pressure is 2.5MPa, and the liquid volume air speed of ethyl acetate is 0.3h-1, Feed hydrogen is 40 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 400 DEG C, and feed pressure is 2.5 MPa, the liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 18:1.Reaction result is shown in Table 1.
【Embodiment 8】
1. catalyst preparation
(1) hydrogenation catalyst:Prepare hydrogenation catalyst according to the same manner as in Example 1.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Investigate ethyl acetate and the reactivity worth of benzene synthesizing ethyl benzene according to the same manner as in Example 1.Reaction condition is:The One reactor reaction temperature is 240 DEG C, and feed pressure is 2MPa, and the liquid volume air speed of ethyl acetate is 0.3h-1, Feed hydrogen is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 380 DEG C, and feed pressure is 2 MPa, the liquid volume air speed of benzene is 2.5h-1, the benzene of charging and the mol ratio of ethyl acetate are 9:1.Reaction result is shown in Table 1.
【Embodiment 9】
1. catalyst preparation
(1) hydrogenation catalyst:Prepare hydrogenation catalyst according to the same manner as in Example 1.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Investigate ethyl acetate and the reactivity worth of benzene synthesizing ethyl benzene according to the same manner as in Example 1.Reaction condition is:The One reactor reaction temperature is 230 DEG C, and feed pressure is 3MPa, and the liquid volume air speed of ethyl acetate is 0.6h-1, Feed hydrogen is 30 with the mol ratio of ethyl acetate:1;Second reactor reaction temperature is 350 DEG C, and feed pressure is 3 MPa, the liquid volume air speed of benzene is 5h-1, the benzene of charging and the mol ratio of ethyl acetate are 9:1.Reaction result is shown in Table 1.
【Comparative example 1】
1. catalyst preparation
(1) hydrogenation catalyst:Prepare hydrogenation catalyst according to the same manner as in Example 1.
(2) alkylation catalyst:ZSM-5 molecular sieve pressed powder is pulverized, and the granule choosing 20~40 mesh is standby.
2. evaluating catalyst
Ethyl acetate and benzene synthesizing ethyl benzene are carried out on the continuous fixed bed reactor of two series connection, and hydrogenation catalyst fills Fill out in first reactor, alkylation catalyst is seated in second reactor, two catalyst in reactor fillings Volume is 5mL, and hydrogen, ethyl acetate and benzene all feed jointly in first reactor, and first reactor outlet obtains To logistics enter back into reaction in second reactor.Reaction condition is:First reactor reaction temperature is 240 DEG C, Feed pressure is 2MPa, and the liquid volume air speed of ethyl acetate is 0.3h-1, the mol ratio of feed hydrogen and ethyl acetate For 30:1;Second reactor reaction temperature is 400 DEG C, and feed pressure is 2MPa, and the liquid volume air speed of benzene is 5h-1, The benzene of charging and the mol ratio of ethyl acetate are 18:1.Reaction result is shown in Table 1.
This comparative example is the ethylbenzene synthetic method of hydrogen, ethyl acetate and benzene one section feeding, understands on year-on-year basis with embodiment 1, The ethylbenzene synthetic method of two section feedings that effect provides well below the present invention.
Table 1

Claims (10)

1. the synthetic method of ethylbenzene, including hydrogenation reactor and alkylation reactor, comprises the steps:
(1) in hydrogenation reactor, in the presence of a hydrogenation catalyst, hydrogen and ethyl acetate carry out hydrogenation reaction, obtain thing Stream I;
(2) stream I and benzene are mixed to get stream I I;
(3) in alkylation reactor, in the presence of alkylation catalyst, stream I I occurs alkylated reaction to obtain containing second Stream I II of benzene.
2. method according to claim 1, is characterized in that described hydrogenation catalyst includes carrier and active component; At least one in described carriers selected from silica, titanium dioxide and aluminium oxide;Described active component includes following components:
Component 1:Gallium or its oxide;
Component 2:The corresponding simple substance of at least one element of VIII race or its oxide in the periodic table of elements;
Component 3:The corresponding simple substance of at least one element of II B race or its oxide in the periodic table of elements;
Component 4:The corresponding simple substance of at least one element of group of the lanthanides or its oxide in the periodic table of elements;
In parts by weight, carrier:Component 1:Component 2:Component 3:Component 4 is 100:(1~15):(1~30):(1~10):(1~5).
3. method according to claim 1, is characterized in that:Described alkylation catalyst is molecular sieve.
4. method according to claim 3, is characterized in that:Described molecular sieve is hydrogen type molecular sieve.
5. method according to claim 1, is characterized in that:Hydrogenation reaction pressure and/or alkylated reaction pressure are 2~3MPa.
6. method according to claim 1, is characterized in that:Hydrogenation reaction temperature is 200~260 DEG C
7. method according to claim 1, is characterized in that:In hydrogenation reactor charging, hydrogen and ethyl acetate rubs That ratio is 20~50.
8. method according to claim 1, is characterized in that:The liquid volume air speed of ethyl acetate is 0.3~0.9h-1.
9. method according to claim 1, is characterized in that:Alkylated reaction temperature is 300~400 DEG C.
10. method according to claim 1, is characterized in that:The liquid volume air speed of benzene is 2~8h-1.
CN201510492936.5A 2015-08-12 2015-08-12 The synthetic method of ethylbenzene Active CN106431809B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510492936.5A CN106431809B (en) 2015-08-12 2015-08-12 The synthetic method of ethylbenzene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510492936.5A CN106431809B (en) 2015-08-12 2015-08-12 The synthetic method of ethylbenzene

Publications (2)

Publication Number Publication Date
CN106431809A true CN106431809A (en) 2017-02-22
CN106431809B CN106431809B (en) 2019-01-25

Family

ID=58093529

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510492936.5A Active CN106431809B (en) 2015-08-12 2015-08-12 The synthetic method of ethylbenzene

Country Status (1)

Country Link
CN (1) CN106431809B (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102875315A (en) * 2011-07-11 2013-01-16 中国石油化工股份有限公司 Method for preparing ethylbenzene by ethanol and benzene vapor-phase alkylation
CN102976892A (en) * 2012-11-22 2013-03-20 天津大学 Method for preparing ethanol through acetic ester hydrogenation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102875315A (en) * 2011-07-11 2013-01-16 中国石油化工股份有限公司 Method for preparing ethylbenzene by ethanol and benzene vapor-phase alkylation
CN102976892A (en) * 2012-11-22 2013-03-20 天津大学 Method for preparing ethanol through acetic ester hydrogenation

Also Published As

Publication number Publication date
CN106431809B (en) 2019-01-25

Similar Documents

Publication Publication Date Title
CN106582625B (en) The catalyst of selective hydrogenation of butadiene
CN101927168B (en) Nickel-based catalyst for preparing isopropyl alcohol by acetone hydrogenation and application thereof
CN102531917A (en) Process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine
CN106582706B (en) Selective hydrogenation of butadiene catalyst
CN102500409B (en) Gasoline aromatization and isomerization reforming catalyst and preparation method and applications thereof
CN103418378B (en) A kind of cracking c_4 fraction selective hydrogenation palladium-based catalyst
CN103894207B (en) High-dispersion catalyst for liquid-phase hydrogenation of octanol mixture and preparation and application thereof
CN105642324B (en) A kind of base metal selective hydrocatalyst and its preparation method and application
CN101745389A (en) A kind of egg-shell catalyst that is used for preparation of ethylene through selective hydrogenation of acetylene
CN100567240C (en) A kind of method of synthesizing 2-ethoxy-phenol
CN102049255A (en) Palladium-based catalyst for selective hydrogenation of cracked C4 fractions and preparation method thereof
CN101569862B (en) lower fatty amine catalyst
CN106431809A (en) Synthesis method of ethylbenzene
CN109092302B (en) Method for selective hydrogenation of butadiene
CN106423255B (en) Ethylbenzene catalyst and preparation method thereof
CN114100653B (en) Nitride supported palladium catalyst and preparation method and application thereof
CN105727954A (en) Preparation method of catalyst for synthetic gas to natural gas
CN100467439C (en) Process for synthesizing dialkyldiphenylamine
CN109092305A (en) The catalyst of selective hydrogenation of butadiene
CN107649147A (en) Hydrogenation catalyst, its application and the method for preparing cis-pinane using its catalysis α pinene hydrogenation
CN110790669A (en) Application of nano-carbon-supported single-atom palladium-based catalyst in preparation of secondary amine by catalytic hydrogenation of nitrile compound
CN106423254B (en) By the catalyst of acetic acid and benzene synthesizing ethyl benzene
CN106582790B (en) The catalyst reacted is alkylated with ethane for benzene
CN106582704B (en) Two sections of compound nickel-base catalyst beds
CN109092303B (en) Catalyst for selective hydrogenation of butadiene

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant