CN103102240A - Synthesis method of sec-butylbenzene - Google Patents
Synthesis method of sec-butylbenzene Download PDFInfo
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- CN103102240A CN103102240A CN2011103594313A CN201110359431A CN103102240A CN 103102240 A CN103102240 A CN 103102240A CN 2011103594313 A CN2011103594313 A CN 2011103594313A CN 201110359431 A CN201110359431 A CN 201110359431A CN 103102240 A CN103102240 A CN 103102240A
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Abstract
The invention relates to a synthesis method of sec-butylbenzene. The synthesis method mainly solves the problems that a synthetic catalyst containing molecular sieve sec-butylbenzene in the prior art is instable in activity and low in sec-butylbenzene selectivity. According to the synthesis method, the sec-butylbenzene which do not contain tert-butyl benzene basically can be stably synthesized by optimizing a novel molecular sieve alkylated catalyst under the conditions that the reaction temperature is 100-280 DEG C, the reaction pressure is 1.0-6.0MPa, the space velocity is 0.1-20h<-1> and the molar ratio of benzene to olefin is about 2-20, wherein the novel molecular sieve alkylated catalyst has the capabilities of keeping high conversion rate of hybrid linear butylene and high selectivity of sec-butylbenzene for a long peroid. The sec-butylbenzene with high purity can be obtained by rectification and the like in a high-yield manner, and the synthesis method can be used for industrial production of sec-butylbenzene synthesis.
Description
Technical field
The present invention relates to petrochemical industry, be specifically related to a kind of synthetic method of sec-butylbenzene.
Background technology
Sec-butylbenzene progressively obtains people's extensive concern in recent years as a kind of solvent and a kind of organic raw material or important chemical intermediate (producing phenol and methylethylketone).
At present, the method for synthesizing sec-butyl benzene is a kind of is with AlCl
3With solid phosphoric acid be catalyzer, with butylene and benzene alkylation synthesizing sec-butyl benzene, the method not only produces sec-butylbenzene, and the by products of the different amounts of generation, mainly isobutyl-benzene, tert.-butylbenzene, dibutyl benzene and tributyl benzene, in these compounds, dibutyl benzene easily separates from reaction mixture with tributyl benzene and can follow the extra sec-butylbenzene of transalkylation generation.Yet the boiling point of isobutyl-benzene, sec-butylbenzene and tert.-butylbenzene is respectively 172.8 ℃, 173.5 ℃ and 169 ℃, therefore is difficult to by rectifying, these compounds are separated from each other.
U.S. Patent No. 5,059,736 have described the method for preparing sec-butylbenzene from benzene and n-butene.It is included under uniform liquid aluminum chloride complex catalyst existence and makes benzene and n-butene reaction, used catalyst comprises aluminum chloride, hydrogenchloride and aromatic hydrocarbons, the amount that wherein is used as the aluminum chloride of complex catalyst component is the 0.5-5.0% of benzene used, temperature of reaction is 20-70 ℃, and the amount of the isobutyl-benzene that forms as by product and the weight ratio of sec-butylbenzene are not more than 0.01: 1.
Nineteen ninety, U.S. Patent No. 4,891,458 disclose for the alkylation of aromatic hydrocarbons (as benzene) or the method for transalkylation, and it is included under at least part of liquid-phase condition and exists under the catalyzer existence that contains the β zeolite, makes aromatic hydrocarbons and C
2-C
4Olefin alkylation or the contact of many alkylaromatic hydrocarbons transalkylation contact substance.Although preferred alkene is ethene and propylene, it is said that suitable alkene alkylating agent comprises ethene, propylene, 1-butylene, trans-2-butene and cis-2-butene or its mixture.In the situation that benzene and n-butene or the reaction of many butylbenzenes it is said that reaction product comprises sec-butylbenzene, but this patent are based on the relevant discovery in laboratory basically, therefore still there is a big difference from industrialization.
A kind of disclosed method for preparing phenol and methylethylketone of Chinese patent CN 101006033A has comprised benzene and carbon four and has been included in comprising the β zeolite or have under the alkylating agent condition
With
The molecular sieve catalyst contact of the peaked x-ray diffraction pattern in d-interval at place particularly comprises the molecular sieve that is selected from zeolite beta, mordenite, USY, MCM-22, PSH-3, SSZ-25, ERB-1, ITQ-1, ITQ-2, MCM-36, MCM-49, MCM-56, UZM-8 and composition thereof in alkylation catalyst.The method finds that in making benzene alkylation with the line style butylene, the zeolite beta zeolite can produce the sec-butylbenzene of lower concentration isobutyl-benzene and tert.-butylbenzene as catalyzer.but the catalyst life that shows this invention use in this patent working example is partially short, during cycle at preferred MCM-22 and the catalyzer that contains zeolite beta at the longest 13 days, the fluctuation of 2-butylene transformation efficiency rises and falls large, particularly change fluctuation more obvious when using the mixed butene charging, as when containing 65Wt% β/35% alumina binder, from the 2-butylene transformation efficiency 97.5% of first day drop to very soon the 5th day 48.5%, the selectivity of sec-butylbenzene drops to 70% from the highest 83%, catalyst catalytic performance can not satisfy long-term operation, illustrate that thus this invention still is in the laboratory study level, also has larger gap from industrial applications.
Introduced a kind of method for preparing sec-butylbenzene in international monopoly W02006015824A1, with benzene and ethene as raw material, as catalyzer, carry out alkylated reaction in autoclave, 220 ℃ of temperature with the MCM-22 of Pd modification, pressure 3.9MPa, benzene alkene under the condition of reaction times 4h, it is said that the transformation efficiency of ethene is 100% than 3.25, in product, the massfraction of sec-butylbenzene can reach 99.5%, and the massfraction of ethylbenzene is 0.5%.
A kind of disclosed method for preparing phenol and methylethylketone of Chinese patent CN101384533A is included under alkylation conditions and the alkylation catalyst that comprises at least a MCM-22 family molecular sieves makes benzene and C under existing
4Alkylating agent contacts to prepare the alkylation that comprises sec-butylbenzene and flows out thing, wherein implements contact and provides C to each reaction zone at a plurality of reaction zones
4Alkylating agent, the sec-butylbenzene cut from this alkylation flow out thing reclaim and comprise at least 95% sec-butylbenzene, less than the C8+ alkene of 100 ppm by weight, less than isobutyl-benzene and the tert.-butylbenzene of 0.5 % by weight.But show that in this patent working example the consumption of the alkylation catalyst catalyzer that contains at least a MCM-22 family molecular sieves that this invention is used is generally all less than 1g, the sec-butylbenzene synthesising reacting time is very short (the grade by 188 hours generally in 1 hour, no longer than 200 hours), butene conversion and sec-butylbenzene selectivity fluctuation simultaneously rises and falls large, illustrate also that thus this invention still is in the laboratory and explores or the lab scale research level, also have larger gap from industrial applications.
Summary of the invention
Technical problem to be solved by this invention be exist in prior art to contain molecular sieve sec-butylbenzene synthetic catalyst activity unstable, the problem that the sec-butylbenzene selectivity is not high, preferred a kind of energy long period keeps mixing the novel alkylation catalyst that contains at least rich aluminium beta-molecular sieve that industrial prospect is arranged of line style butylene high conversion, sec-butylbenzene highly selective, can high stable yield synthesize the low sec-butylbenzene that contains or do not contain tert.-butylbenzene under suitable reaction conditions, can obtain highly purified sec-butylbenzene product by high yield by processes such as rectifying.
The present invention solves the problems of the technologies described above the technical scheme that adopts:
A kind of synthetic method of sec-butylbenzene, mix as molecular sieve allcylation catalyst less than one or more in 20 allitic beta-zeolite or allitic beta-zeolite and MCM family zeolite with silica alumina ratio, the mixture of one or more in the carbon four-wire type organic compound is as raw material, and add benzene, at temperature of reaction 100-280 ℃, reaction pressure 1.0-6.0MPa, raw material charging weight hourly space velocity 0.1-20h
-1Condition under, synthesizing tertiary butyl benzene mass content is not higher than 1% or do not contain the sec-butylbenzene of tert.-butylbenzene; The mixture of one or more in described carbon four-wire type organic compound is: the mixture that contains the n-butene of the iso-butylene of 0-0.5wt% and 99.5-100wt%; Or contain one or more in the butane of 0.5-90wt%, with the iso-butylene of 0-0.5wt%, the mixture of 10-99wt% n-butene; The mol ratio 2-20 of benzene and alkene.
One or more in described butane are chosen the mixture of normal butane and Trimethylmethane.
Described temperature of reaction is 120-270 ℃, and reaction pressure is 1.5-4.5MPa, and raw material charging weight hourly space velocity is 0.2-10h
-1
Described temperature of reaction is preferably 140-250 ℃; Reaction pressure is preferably 1.8-3.5MPa; Raw material charging weight hourly space velocity is preferably 0.4-5h
-1
Described MCM family zeolite comprises MCM-22, MCM-36, MCM-49 or MCM-56.
React last synthetic product by rectifying, obtain the tert.-butylbenzene mass content not higher than 1% or do not contain the sec-butylbenzene of tert.-butylbenzene.
The present invention is by preferably long period keeping, the novel molecular sieve alkylation catalyst that contains at least rich aluminium beta-molecular sieve that mixes line style butylene high conversion, sec-butylbenzene highly selective, under above-mentioned reaction conditions, not contain or low mixed c 4 line style butylene and the stable synthetic sec-butylbenzene of tert.-butylbenzene that substantially do not contain of benzene direct alkylation that contains iso-butylene, synthetic effluent can obtain highly purified sec-butylbenzene product by the high yield of the processes such as rectifying, can be used in the synthetic industrial production of sec-butylbenzene.
In order to illustrate that purpose of the present invention has provided following examples, they do not limit the scope of the invention.
Embodiment
Embodiment 1: the sec-butylbenzene when using butene-1 as carbon four raw material is synthetic
With 20g be shaped to isothermal that containing at least of cylindric (diameter 1mm) of rich aluminium beta-molecular sieve catalyzer (60% (massfraction) molecular sieve/40% (massfraction) binding agent etc.) internal diameter of packing into is 20mm, upwards flow, in the tubular reactor of fixed bed, fill with quartz sand gap, catalyst in reactor two ends.Benzene is full of after reactor assembly progressively increasing temperature and pressure, reaches 145 ℃ in temperature of reaction, with butene-1 (iso-butylene content is less than 0.5%) incision reactor, control weight hourly space velocity 3h when reaction pressure reaches 2.0MPa
-1And benzene alkene mol ratio is to carry out the sec-butylbenzene building-up reactions under 3 condition, along with the variation appropriate change reaction conditions of butene-1 transformation efficiency such as can improve temperature of reaction etc. when the C 4 olefin transformation efficiency obviously descends, such as when the every decline 0.5-1 of transformation efficiency percentage point can on put forward 1 ℃ of temperature of reaction.Analyze synthetic product by on-line chromatograph and form, the transformation efficiency of butene-1, sec-butylbenzene selectivity and production time see Table 1.It is sec-butylbenzene more than 99.5% that the cooling synthetic product that obtains can be obtained purity through rectifying.
Table 1
Embodiment 2: use the sec-butylbenzene when mixing positive and negative butene-2 as carbon four raw material synthetic
With 20g be shaped to isothermal that containing at least of cylindric (diameter 1mm) of rich aluminium beta-molecular sieve catalyzer (60% (massfraction) molecular sieve/40% (massfraction) binding agent etc.) internal diameter of packing into is 20mm, upwards flow, in the tubular reactor of fixed bed, fill with quartz sand gap, catalyst in reactor two ends.Benzene is full of after reactor assembly progressively increasing temperature and pressure, reaches 148 ℃ in temperature of reaction, when reaction pressure reaches 2.0MPa, (iso-butylene content is less than 0.5% with butene-2, maleic-255.2%, anti-butene-2 44.6%) the incision reactor, control weight hourly space velocity 8h
-1And benzene alkene mol ratio is 15, along with the variation appropriate change reaction conditions of mixed butene-2 transformation efficiency such as can improve temperature of reaction etc. when the C 4 olefin transformation efficiency obviously descends, such as when the every decline 0.5-1 of transformation efficiency percentage point can on put forward 1 ℃ of temperature of reaction.Analyze synthetic product by on-line chromatograph and form, the transformation efficiency of butene-2, sec-butylbenzene selectivity and production time see Table 2.It is sec-butylbenzene more than 99.5% that the cooling synthetic product that obtains can be obtained purity through rectifying.
Table 2
Embodiment 3: the sec-butylbenzene when using mixed butene-1 and positive and negative butene-2 as carbon four raw material is synthetic
With 50g be shaped to isothermal that containing at least of cylindric (diameter 1mm) of rich aluminium beta-molecular sieve catalyzer (60% (massfraction) molecular sieve/40% (massfraction) binding agent etc.) internal diameter of packing into is 20mm, upwards flow, in the tubular reactor of fixed bed, fill with quartz sand gap, catalyst in reactor two ends.Benzene is full of after reactor assembly progressively increasing temperature and pressure, reach 147 ℃ in temperature of reaction, when reaction pressure reaches 2.0MPa, (iso-butylene content is less than 0.5% with mixed butene, butene-1 50.2%, maleic-2 25.2%, anti-butene-2 24.2%) the incision reactor, control weight hourly space velocity 5h
-1And benzene alkene mol ratio is 8, along with the variation appropriate change reaction conditions of mixed butene-1 and butene-2 total conversion rate such as can improve temperature of reaction etc. when the C 4 olefin transformation efficiency obviously descends, such as when the every decline 0.5-1 of transformation efficiency percentage point can on put forward 1 ℃ of temperature of reaction.Analyze synthetic product by on-line chromatograph and form, transformation efficiency, sec-butylbenzene selectivity and the production time of total butylene see Table 3.It is sec-butylbenzene more than 99.5% that the cooling synthetic product that obtains can be obtained purity through rectifying.
Table 3
Embodiment 4: use the sec-butylbenzene when carbon four is as carbon four raw material after industrial mixed ether synthetic
With 100g be shaped to isothermal that containing at least of cylindric (diameter 1mm) of rich aluminium beta-molecular sieve catalyzer (66% (massfraction) molecular sieve/34% (massfraction) binding agent etc.) internal diameter of packing into is 30mm, upwards flow, in the tubular reactor of fixed bed, fill with quartz sand gap, catalyst in reactor two ends.Benzene is full of after reactor assembly progressively increasing temperature and pressure, reach 146 ℃ in temperature of reaction, when reaction pressure reaches 2.0MPa, (iso-butylene content is less than 0.5% with carbon four after industrial mixed ether, butene-1 17.8%, maleic-2 12.9%, anti-butene-2 19.7%, normal butane 8.7%, Trimethylmethane 40.5%) the incision reactor, control weight hourly space velocity 5h
-1And benzene alkene mol ratio is 15 to carry out the sec-butylbenzene building-up reactions, along with the variation appropriate change reaction conditions of total butene conversion in carbon after ether four such as can improve temperature of reaction etc. when the C 4 olefin transformation efficiency obviously descends, such as when the every decline 0.5-1 of transformation efficiency percentage point can on put forward 1 ℃ of temperature of reaction.Analyze synthetic product by on-line chromatograph and form, total butene conversion, sec-butylbenzene selectivity and production time see Table 4.It is sec-butylbenzene more than 99.4% that the cooling synthetic product that obtains can be obtained purity through rectifying.
Table 4
Embodiment 5: use the sec-butylbenzene the when mixed butene after carbon four concentrates is as raw material after industrial ether synthetic
With 100g be shaped to isothermal that containing at least of cylindric (diameter 1mm) of rich aluminium beta-molecular sieve catalyzer (66% (massfraction) molecular sieve/34% (massfraction) binding agent etc.) internal diameter of packing into is 30mm, upwards flow, in the tubular reactor of fixed bed, fill with quartz sand gap, catalyst in reactor two ends.Benzene is full of after reactor assembly progressively increasing temperature and pressure, reach 150 ℃ in temperature of reaction, when reaction pressure reaches 2.0MPa, (iso-butylene content is less than 0.5% with the mixed butene after carbon four concentrates after industrial ether, butene-1 35.3%, maleic-2 25.0%, anti-butene-2 39.5%) the incision reactor, control weight hourly space velocity 3h
-1And benzene alkene mol ratio is 10 to carry out the sec-butylbenzene building-up reactions, along with the variation appropriate change reaction conditions of total butene conversion such as such as can improve temperature of reaction etc. when the C 4 olefin transformation efficiency obviously descends, such as when the every decline 0.5-1 of transformation efficiency percentage point can on put forward 1 ℃ of temperature of reaction.Analyze synthetic product by on-line chromatograph and form, total butene conversion, sec-butylbenzene selectivity and production time see Table 5.It is sec-butylbenzene more than 99.4% that the cooling synthetic product that obtains can be obtained purity through rectifying.
Table 5
Embodiment 6: use the sec-butylbenzene the when mixed butene after carbon four concentrates is as raw material after industrial ether synthetic
With 100g be shaped to isothermal that containing at least of cylindric (diameter 1mm) of rich aluminium beta-molecular sieve catalyzer (40% (massfraction) rich aluminium beta-molecular sieve/26% (massfraction) MCM-22 molecular sieve/34% (massfraction) binding agent etc.) internal diameter of packing into is 30mm, upwards flow, in the tubular reactor of fixed bed, fill with quartz sand gap, catalyst in reactor two ends.Benzene is full of after reactor assembly progressively increasing temperature and pressure, reach 150 ℃ in temperature of reaction, when reaction pressure reaches 2.0MPa, (iso-butylene content is less than 0.5% with the mixed butene after carbon four concentrates after industrial ether, butene-1 35.3%, maleic-2 25.0%, anti-butene-2 39.5%) the incision reactor, control weight hourly space velocity 3h
-1And benzene alkene mol ratio is 10 to carry out the sec-butylbenzene building-up reactions, along with the variation appropriate change reaction conditions of total butene conversion such as such as can improve temperature of reaction etc. when the C 4 olefin transformation efficiency obviously descends, such as when the every decline 0.5-1 of transformation efficiency percentage point can on put forward 1 ℃ of temperature of reaction.Analyze synthetic product by on-line chromatograph and form, total butene conversion, sec-butylbenzene selectivity and production time see Table 6.It is sec-butylbenzene more than 99.4% that the cooling synthetic product that obtains can be obtained purity through rectifying.
Table 6
Claims (6)
1. the synthetic method of a sec-butylbenzene, it is characterized in that, mix as molecular sieve allcylation catalyst less than one or more in 20 allitic beta-zeolite or allitic beta-zeolite and MCM family zeolite with silica alumina ratio, the mixture of one or more in the carbon four-wire type organic compound is as raw material, and add benzene, at temperature of reaction 100-280 ℃, reaction pressure 1.0-6.0MPa, raw material charging weight hourly space velocity 0.1-20h
-1Condition under, synthesizing tertiary butyl benzene mass content is not higher than 1% or do not contain the sec-butylbenzene of tert.-butylbenzene; The mixture of one or more in described carbon four-wire type organic compound is: the mixture that contains the n-butene of the iso-butylene of 0-0.5wt% and 99.5-100wt%; Or contain one or more in the butane of 0.5-90wt%, with the iso-butylene of 0-0.5wt%, the mixture of 10-99wt% n-butene; The mol ratio 2-20 of benzene and alkene.
2. the method for claim 1, is characterized in that, one or more in described butane are chosen the mixture of normal butane and Trimethylmethane.
3. the method for claim 1, is characterized in that, described temperature of reaction is 120-270 ℃, and reaction pressure is 1.5-4.5MPa, and raw material charging weight hourly space velocity is 0.2-10h
-1
4. method as described in claim 1 or 3, is characterized in that, described temperature of reaction is 140-250 ℃; Reaction pressure 1.8-3.5MPa; Raw material charging weight hourly space velocity is 0.4-5h
-1
5. the method for claim 1, is characterized in that, described MCM family zeolite comprises MCM-22, MCM-36, MCM-49 or MCM-56.
6. the method for claim 1, is characterized in that, reacts last synthetic product by rectifying, obtains the tert.-butylbenzene mass content not higher than 1% or do not contain the sec-butylbenzene of tert.-butylbenzene.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447173B (en) * | 2013-09-24 | 2018-05-11 | 中国石油化工股份有限公司 | The method for producing sec-butylbenzene |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101006033A (en) * | 2004-08-13 | 2007-07-25 | 埃克森美孚化学专利公司 | Process for producing phenol and methyl ethyl ketone |
| CN101274764A (en) * | 2007-03-30 | 2008-10-01 | 中国石油化工股份有限公司 | Preparation for nanometer allitic beta-zeolite |
| US20100317896A1 (en) * | 2007-08-22 | 2010-12-16 | Cheng Jane C | Process For Producing Sec-Butylbenzene |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101006033A (en) * | 2004-08-13 | 2007-07-25 | 埃克森美孚化学专利公司 | Process for producing phenol and methyl ethyl ketone |
| CN101274764A (en) * | 2007-03-30 | 2008-10-01 | 中国石油化工股份有限公司 | Preparation for nanometer allitic beta-zeolite |
| US20100317896A1 (en) * | 2007-08-22 | 2010-12-16 | Cheng Jane C | Process For Producing Sec-Butylbenzene |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447173B (en) * | 2013-09-24 | 2018-05-11 | 中国石油化工股份有限公司 | The method for producing sec-butylbenzene |
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