CN104549506A - Preparation method of aluminum-based catalyst for alkylation reaction - Google Patents

Preparation method of aluminum-based catalyst for alkylation reaction Download PDF

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CN104549506A
CN104549506A CN201410769556.7A CN201410769556A CN104549506A CN 104549506 A CN104549506 A CN 104549506A CN 201410769556 A CN201410769556 A CN 201410769556A CN 104549506 A CN104549506 A CN 104549506A
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aluminium
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catalyzer
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CN104549506B (en
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詹晓力
何逸波
张庆华
陈丰秋
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Zhejiang University ZJU
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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 discloses a preparation method of an aluminum-based catalyst for alkylation reaction. The method comprises the following steps: firstly preheating an ionic liquid in a perfluoroalkyl sulfonyl imide structure to 60-90 DEG C, then adding with an aluminum-containing compound, and after uniformly stirring and mixing, cooling to normal temperature; and then, putting the reaction system in an N2 atmosphere, and reacting for 6-24 hours at normal temperature, wherein the reaction system and N2 are interacted to generate a complex so as to obtain the catalyst for catalyzing Friedel-Crafts alkylation reaction. The catalyst prepared by the method disclosed by the invention is used for synthesizing Friedel-Crafts alkylation reaction, for example reaction of benzene and 1-laurylene to dodecylbenzene. The catalyst has the characteristics of high activity, relatively high selectivity of 2-striaght chain alkylbenzene (2-LAB), mild using condition and good cyclicity, and can be recovered by virtue of a simple method.

Description

A kind of preparation method of the catalyzer for alkylated reaction based on aluminium
Technical field
The present invention relates to the preparation synthesis of compound, relate to a kind of preparation method of the catalyzer for alkylated reaction based on aluminium, specifically refer to there is per-fluoroalkyl sulfonyl imine structure, containing the preparation method of the catalyst system of aluminium.
Background introduction
Linear alkylbenzene (LAB), especially dodecylbenzene is the important source material of synthetic detergent, the annual requirement of world's linear alkylbenzene more than 3,000,000 tons, and estimate every year by with 4% speed increment.Since nineteen sixty-eight first set Pacol device is for the production of linear alkylbenzene, Friedel-Crafts alkylation process uses HF/AlCl 3as catalyzer.Because HF has strong corrodibility and toxicity, so HF/AlCl 3technique brings series of problems to the maintenance of equipment, safety in production.Use HF, AlCl 3technique, after batch production terminates, catalyst component is difficult to be separated and recycles, and this also brings difficulty to environment protection.Therefore, there is high reactivity, high 2-LAB selectivity for Friedel-Crafts alkylated reaction exploitation one, and the catalyzer with good circulation performance becomes the problem that people need to consider.
Going deep in recent years along with research, ionic liquid has become the important catalytic material of a class.Per-fluoroalkyl sulfonyl imines and salt thereof, due to the height delocalization of negative charge on its central nitrogen atom, can change its acidity, namely having acidity adjustability, improve its applicable handiness by changing its structure.Therefore, per-fluoroalkyl sulfonyl imines class catalyst system becomes alternative classical acid catalyzer, an important selection of catalysis benzene alkylation reaction.
The article (Science China Chemistry (2010), 53,1102) that domestic investigator delivers and patent CN 1225617A disclose and use ionic liquid Et 3nHCl-AlCl 3catalysis benzene and 1-laurylene synthesize the method for dodecylbenzene; Other studies in China person also delivered article (Applied Catalysis A:General (2005), 292,354), disclosed use [Rmim] Al 2cl 6br plasma liquid catalyst benzene and 1-laurylene synthesize the method for dodecylbenzene.Though the catalyst system described in above disclosure has active high feature, they are after recycling, and catalytic activity declines obviously, and they are on the low side to the latitude of moisture, namely easily meet water inactivation.
The use HY type molecular sieve catalyst catalysis benzene that patent CN 1077808C and patent CN 1131107C etc. are disclosed and 1-laurylene synthesize the reaction of dodecylbenzene, though have the advantage that selectivity is very high, but its temperature of reaction is higher, and reaction pressure is high, this limits the use of molecular sieve to a certain extent.And molecular sieve generally has the feature of easy carbon distribution and inactivation, therefore from the cyclicity of molecular sieve catalysts principle not as good as ionic liquid class catalyzer of the present invention.
Summary of the invention
The object of the invention is for the deficiencies in the prior art, a kind of preparation method of the novel catalyzer for Friedel-Crafts alkylated reaction is provided, it is high that the catalyzer making it prepare has reactive behavior, 2-straight chained alkyl benzene selective is higher, working conditions is gentle, be separated simple, recycle performance good, the feature that water tolerance is strong.
The inventive method is: first the ionic liquid with per-fluoroalkyl sulfonyl imine structure is preheated to 60 ~ 90 DEG C, then adds aluminum contained compound, be down to normal temperature after being uniformly mixed; Then reaction system is placed in N 2under atmosphere, react 6 ~ 24h under normal temperature, make its generation title complex that reacts to each other, obtain the catalyzer for catalysis Friedel-Crafts alkylated reaction; Aluminum contained compound is 1:1 ~ 4:1 with the mol ratio of the ionic liquid with per-fluoroalkyl sulfonyl imine structure;
Described aluminum contained compound is aluminum chloride (AlCl 3), three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium one or more; Wherein the structural formula of three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium is Al (N (SO 2r f) 2) 3, R f=C nf 2n+1, n=0 ~ 6;
The described ionic liquid with per-fluoroalkyl sulfonyl imine structure needs vacuum-drying 24h under 60 ~ 140 DEG C of conditions before use;
The described ionic liquid with per-fluoroalkyl sulfonyl imine structure is [1-butyl-3-Methylimidazole] [bis trifluoromethyl sulfimide].
The catalyzer that the inventive method prepares is for the synthesis of Friedel-Crafts alkylated reaction, as benzene and 1-laurylene synthesize the reaction of dodecylbenzene, this catalyzer has active high, 2-linear alkylbenzene (2-LAB) selectivity is higher, working conditions is gentle, can be reclaimed by simple method, and the feature that cyclicity is good.
Benzene and 1-laurylene synthesize in the reaction of dodecylbenzene, the title complex utilizing the present invention to prepare is as catalyzer, catalyst charge is 1 ~ 10wt ﹪ that benzene and 1-laurylene add quality sum, temperature of reaction is 10 ~ 80 DEG C, the mol ratio of 1-laurylene and benzene is 1:1 ~ 1:7, reaction times is 10 ~ 30min, and pressure is normal pressure;
Described three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium can be synthesized by following two kinds of methods:
One method is by aluminum chloride AlCl 3mix with per-fluoroalkyl sulfonyl imines, obtain compound; In compound, add toluene again, under normal temperature, react 15 ~ 30min, need the HCl removing will produced in time in reaction process, cross leaching solid; Solid q. s. toluene washs, and dry, namely obtains corresponding three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium; Wherein the mol ratio of aluminum chloride and per-fluoroalkyl sulfonyl imines is 1:3 ~ 1:5; The mass ratio of toluene and compound is 2:1 ~ 1:2;
Another kind method adds toluene in per-fluoroalkyl sulfonyl imines, is made into the per-fluoroalkyl sulfonyl imide liquor that concentration is 0.5 ~ 1.5mol/L; Then in per-fluoroalkyl sulfonyl imide liquor, Al (C is slowly added 2h 5) 3hexane solution, react 30 ~ 90min under normal temperature, cross leaching solid; Solid q. s. toluene washs, and dry, namely obtains corresponding three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium; Wherein said Al (C 2h 5) 3hexane solution in Al (C 2h 5) 3concentration is 0.5 ~ 1.5mol/L.Per-fluoroalkyl sulfonyl imide liquor and Al (C 2h 5) 3the volume ratio of hexane solution be 3:1, control Al (C 2h 5) 3hexane solution concentration make added per-fluoroalkyl sulfonyl imines and Al (C 2h 5) 3amount of substance than for 3:1 ~ 3.6:1.
Beneficial effect of the present invention is as follows:
The catalyzer that the inventive method prepares is for the synthesis of Friedel-Crafts alkylated reaction, as benzene and 1-laurylene synthesize the reaction of dodecylbenzene, this catalyzer has active high, 2-linear alkylbenzene (2-LAB) selectivity is higher, working conditions is gentle, can be reclaimed by simple method, and the feature that cyclicity is good.
Embodiment
Below in conjunction with specific embodiment, the present invention is further analyzed.
First the embodiment preparing three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium is as follows:
Embodiment 1-1
In the round-bottomed flask being furnished with stirring and atmospheric vent, add two fluorine sulfimide HN (SO 2f) 2(3.1g, 18.8mmol), then add the toluene 38ml after distilation.Stirring makes it fully dissolve becomes homogeneous phase, slowly adds the Al (C of 0.5mol/L afterwards wherein 2h 5) 2hexane solution 13ml.Reaction is carried out in ice-water bath.After reacting about 30min, filter, obtain solid, use 60ml toluene to divide and wash solid 3 times, final vacuum is dry, namely obtains Al (N (SO 2f) 2) 3.Yield is about 50%.
Embodiment 1-2
In the round-bottomed flask being furnished with stirring and atmospheric vent, add two perfluoro hexyl sulfimide HN (SO 2c 6f 13) 2(3.1g, 4mmol), then add the toluene 2.7ml after distilation.Stirring makes it fully dissolve becomes homogeneous phase, slowly adds the Al (C of 0.9mol/L afterwards wherein 2h 5) 2hexane solution 0.9ml.Reaction is carried out in ice-water bath.After reacting about 30min, filter, obtain solid, use 60ml benzene to divide and wash solid 3 times, final vacuum is dry, namely obtains Al (N (SO 2c 6f 13) 2) 3.Yield is about 52%.
Embodiment 1-3
Get two fluorine sulfimide HN (SO 2f) 2(3.1g, 18.8mmol) is dissolved in the 10ml toluene of distillation.In the round-bottomed flask being furnished with stirring and atmospheric vent, add aluminum chloride AlCl 3(0.84g, 6.3mmol).Two fluorine sulfimide solution is added drop-wise in round-bottomed flask slowly.Need in reaction process constantly the HCl of generation to be got rid of from atmospheric vent.Reaction is carried out in ice-water bath.After reacting about 30min, filter, obtain solid, use 60ml benzene to divide and wash solid 3 times, final vacuum is dry, namely obtains Al (N (SO 2f) 2) 3.Yield is about 47%.
Embodiment 1-4
Get two perfluoro hexyl sulfimide HN (SO 2c 6f 13) 2(4.65g, 6mmol) is dissolved in the 10ml toluene of distillation.In the round-bottomed flask being furnished with stirring and atmospheric vent, add aluminum chloride AlCl 3(0.16g, 1.2mmol).Two fluorine sulfimide solution is added drop-wise in round-bottomed flask slowly.Need in reaction process constantly the HCl of generation to be got rid of from atmospheric vent.Reaction is carried out in ice-water bath.After reacting about 30min, filter, obtain solid, use 60ml benzene to divide and wash solid 3 times, final vacuum is dry, namely obtains Al (N (SO 2c 6f 13) 2) 3.Yield is about 46%.
Kaolinite Preparation of Catalyst and the embodiment for the synthesis of Friedel-Crafts alkylated reaction as follows:
The ionic liquid that following examples have per-fluoroalkyl sulfonyl imine structure needs vacuum-drying 24h under 60 ~ 140 DEG C of conditions before use.
Embodiment 2-1
Take ionic liquid [1-butyl-3-Methylimidazole] [bis trifluoromethyl sulfimide] (1.64g, 3.9mmol), be heated to 60 DEG C in dry conditions.Take aluminum chloride AlCl 3(0.26g, 2.0mmol), three (two fluorine sulfimide) aluminium Al (N (SO 2c 6f 13) 2) 3(4.73g, 2.0mmol), slowly joins it in ionic liquid heated, and stir and make it fully dissolve, churning time is 6h.Stop afterwards stirring, make it slowly return to room temperature, namely obtain the ionic-liquid catalyst with per-fluoroalkyl sulfonyl imine structure.
Get benzene (2.5g, 32.0mmol) to mix with 1-laurylene (5.4g, 32.0mmol), be preheated to temperature of reaction 80 DEG C, add the preparation-obtained ionic-liquid catalyst of 0.79g the present invention, start to stir, reaction 30min.Leave standstill, system layering, lower floor is catalyzer, can be recycled by being separated; Upper strata is product.Reaction 1-laurylene transformation efficiency is about 33% more than 90%, 2-LAB selectivity.
Embodiment 2-2
Take ionic liquid [1-butyl-3-Methylimidazole] [bis trifluoromethyl sulfimide] (0.42g, 1.0mmol), be heated to 90 DEG C in dry conditions.Take aluminum chloride AlCl 3(0.26g, 2.0mmol), three (perfluoro hexyl sulfimide) aluminium Al (N (SO 2f) 2) 3(1.13g, 2.0mmol), slowly joins it in ionic liquid heated, and stir and make it fully dissolve, churning time is 24h.Stop afterwards stirring, make it slowly return to room temperature.Namely the ionic-liquid catalyst with per-fluoroalkyl sulfonyl imine structure is obtained.
Get benzene (5g, 64.0mmol) to mix with 1-laurylene (1.2g, 9.1mmol), be preheated to temperature of reaction 10 DEG C, add the preparation-obtained ionic-liquid catalyst of 0.062g the present invention, start to stir, reaction 10min.Leave standstill, system layering, lower floor is catalyzer, can be recycled by being separated; Upper strata is product.Reaction 1-laurylene transformation efficiency is about 42% more than 90%, 2-LAB selectivity.
Embodiment 2-3
Take ionic liquid [1-butyl-3-Methylimidazole] [bis trifluoromethyl sulfimide] (0.42g, 1.0mmol), be heated to 90 DEG C in dry conditions.Take aluminum chloride AlCl 3(0.26g, 2.0mmol), slowly joins it in ionic liquid heated, and stir and make it fully dissolve, churning time is 6h.Stop afterwards stirring, make it slowly return to room temperature.Namely the ionic-liquid catalyst with per-fluoroalkyl sulfonyl imine structure is obtained.
Get benzene (5g, 64.0mmol) to mix with 1-laurylene (1.2g, 9.1mmol), be preheated to temperature of reaction 10 DEG C, add the preparation-obtained ionic-liquid catalyst of 0.062g the present invention, start to stir, reaction 30min.Leave standstill, system layering, lower floor is catalyzer, can be recycled by being separated; Upper strata is product.Reaction 1-laurylene transformation efficiency is about 43% more than 90%, 2-LAB selectivity.
Embodiment 2-4
Take ionic liquid [1-butyl-3-Methylimidazole] [bis trifluoromethyl sulfimide] (0.42g, 1.0mmol), be heated to 90 DEG C in dry conditions.Take three (perfluoro hexyl sulfimide) aluminium Al (N (SO 2f) 2) 3(1.13g, 2.0mmol), slowly joins it in ionic liquid heated, and stir and make it fully dissolve, churning time is 6h.Stop afterwards stirring, make it slowly return to room temperature.Namely the ionic-liquid catalyst with per-fluoroalkyl sulfonyl imine structure is obtained.
Get benzene (5g, 64.0mmol) to mix with 1-laurylene (1.2g, 9.1mmol), be preheated to temperature of reaction 10 DEG C, add the preparation-obtained ionic-liquid catalyst of 0.062g the present invention, start to stir, reaction 30min.Leave standstill, system layering, lower floor is catalyzer, can be recycled by being separated; Upper strata is product.Reaction 1-laurylene transformation efficiency is about 40% more than 90%, 2-LAB selectivity.
Comparison study embodiment:
Get benzene (5g, 64.0mmol) to mix with 1-laurylene (1.2g, 9.1mmol), be preheated to temperature of reaction 10 DEG C, add 0.62g aluminum chloride AlCl 3as catalyzer, start to stir, reaction 30min.Leave standstill, system is homogeneous phase, and catalyzer cannot be separated.Reaction 1-laurylene transformation efficiency is more than 90%, 2-LAB selectivity about 28%.
Above-described embodiment is not that the present invention is not limited only to above-described embodiment for restriction of the present invention, as long as meet application claims, all belongs to protection scope of the present invention.

Claims (9)

1. the preparation method based on the catalyzer for alkylated reaction of aluminium, it is characterized in that the method first the ionic liquid with per-fluoroalkyl sulfonyl imine structure is preheated to 60 ~ 90 DEG C, then add aluminum contained compound, after being uniformly mixed, be down to normal temperature; Then reaction system is placed in N 2under atmosphere, react 6 ~ 24h under normal temperature, make its generation title complex that reacts to each other, obtain the catalyzer for catalysis Friedel-Crafts alkylated reaction.
2. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as claimed in claim 1, is characterized in that aluminum contained compound is 1:1 ~ 4:1 with the mol ratio of the ionic liquid with per-fluoroalkyl sulfonyl imine structure.
3. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as claimed in claim 1 or 2, is characterized in that described aluminum contained compound is aluminum chloride (AlCl 3), one or more in three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium; Wherein the structural formula of three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium is Al (N (SO 2r f) 2) 3, R f=C nf 2n+1, n=0 ~ 6.
4. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as claimed in claim 1 or 2, is characterized in that the described ionic liquid with per-fluoroalkyl sulfonyl imine structure needs vacuum-drying 24h under 60 ~ 140 DEG C of conditions before use.
5. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as described in claim 1 or 2 or 3, is characterized in that the described ionic liquid with per-fluoroalkyl sulfonyl imine structure is for [1-butyl-3-Methylimidazole] [bis trifluoromethyl sulfimide].
6. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as claimed in claim 1, is characterized in that catalyzer that the method prepares is for Friedel-Crafts alkylated reaction.
7. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as claimed in claim 6, it is characterized in that described Friedel-Crafts alkylated reaction is the reaction that benzene and 1-laurylene synthesize dodecylbenzene, catalyst charge is 1 ~ 10wt ﹪ that benzene and 1-laurylene add quality sum, temperature of reaction is 10 ~ 80 DEG C, the mol ratio of 1-laurylene and benzene is 1:1 ~ 1:7, reaction times is 10 ~ 30min, and pressure is normal pressure.
8. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as claimed in claim 3, is characterized in that described three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium can synthesize by the following method: by aluminum chloride AlCl 3mix with per-fluoroalkyl sulfonyl imines, obtain compound; In compound, add toluene again, under normal temperature, react 15 ~ 30min, need the HCl removing will produced in time in reaction process, cross leaching solid; Solid toluene wash, and dry, namely obtain corresponding per-fluoroalkyl sulfonyl imines aluminium; Wherein the mol ratio of aluminum chloride and per-fluoroalkyl sulfonyl imines is 1:3 ~ 1:5; The mass ratio of toluene and compound is 2:1 ~ 1:2.
9. the preparation method of a kind of catalyzer for alkylated reaction based on aluminium as claimed in claim 3, it is characterized in that described three (oroalkane sulfonyl of enjoying a double blessing) imines aluminium can synthesize by the following method: in per-fluoroalkyl sulfonyl imines, add toluene, be made into the per-fluoroalkyl sulfonyl imide liquor that concentration is 0.5 ~ 1.5mol/L; Then in per-fluoroalkyl sulfonyl imide liquor, Al (C is slowly added 2h 5) 3hexane solution, react 30 ~ 90min under normal temperature, cross leaching solid; Solid toluene wash, and dry, namely obtain corresponding per-fluoroalkyl sulfonyl imines aluminium; Described Al (C 2h 5) 3hexane solution in Al (C2H5) 3 concentration be 0.5 ~ 1.5mol/L; Per-fluoroalkyl sulfonyl imide liquor and Al (C 2h 5) 3the volume ratio of hexane solution be 3:1, control Al (C 2h 5) 3hexane solution concentration make added per-fluoroalkyl sulfonyl imines and Al (C 2h 5) 3amount of substance than for 3:1 ~ 3.6:1.
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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN105032491A (en) * 2015-07-03 2015-11-11 浙江大学 Preparation method of ionic-liquid-containing supported catalyst for alkylation reaction
CN108435257A (en) * 2018-06-08 2018-08-24 福州华博立乐新材料科技有限公司 Catalyst of the one kind for synthesizing 3- [2- (the chloro- 2- quinolyls of 7-) vinyl] benzaldehyde
CN112403515A (en) * 2020-12-04 2021-02-26 江苏棋成化工有限公司 Asymmetric bimetal dication ionic liquid catalyst, preparation method and application thereof

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Publication number Priority date Publication date Assignee Title
CN105032491A (en) * 2015-07-03 2015-11-11 浙江大学 Preparation method of ionic-liquid-containing supported catalyst for alkylation reaction
CN108435257A (en) * 2018-06-08 2018-08-24 福州华博立乐新材料科技有限公司 Catalyst of the one kind for synthesizing 3- [2- (the chloro- 2- quinolyls of 7-) vinyl] benzaldehyde
CN112403515A (en) * 2020-12-04 2021-02-26 江苏棋成化工有限公司 Asymmetric bimetal dication ionic liquid catalyst, preparation method and application thereof
CN112403515B (en) * 2020-12-04 2022-09-02 江苏棋成化工有限公司 Asymmetric bimetal dication ionic liquid catalyst, preparation method and application thereof

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