CN103232342B - Method for preparing methyl cyclohexyl acetate from toluene - Google Patents

Method for preparing methyl cyclohexyl acetate from toluene Download PDF

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CN103232342B
CN103232342B CN201310135407.0A CN201310135407A CN103232342B CN 103232342 B CN103232342 B CN 103232342B CN 201310135407 A CN201310135407 A CN 201310135407A CN 103232342 B CN103232342 B CN 103232342B
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toluene
tetrahydrotoluene
hydrogenation
reaction
acetic acid
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CN103232342A (en
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佘喜春
向明林
李庆华
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Hunan Changlian New Material Technology Co ltd
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Hunan Changling Petrochemical Technology Development Co Ltd
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Abstract

The invention provides a method for preparing methyl cyclohexyl acetate from toluene. The method comprises a toluene hydrogenation reaction and an olefinic acid esterification reaction. The method also comprises secondary separation steps. With the method provided by the invention, methyl cyclohexyl acetate can be prepared from toluene. Compared with prior art, the method has the advantages of cheap and easy-to-obtain raw material and large preparation cost advantage. Therefore, good economic benefit can be provided.

Description

A kind of method of being prepared methylcyclohexyl acetate by toluene
Technical field
The invention belongs to chemical field, be specifically related to a kind of method of being prepared methylcyclohexyl acetate by toluene.
Background technology
Methylcyclohexyl acetate is a kind of colourless viscous liquid, has the typical chemical property of ester class, is also the organic synthesis intermediate that purposes is wider.Methylcyclohexyl acetate is mainly for the production of the solvent system of hydrogen peroxide process, for dissolving quinones organism.With methylcyclohexyl acetate replace trioctyl phosphate make solvent, can increase anthraquinone and the solubleness of hydrogen anthraquinone in working fluid and the partition ratio of hydrogen peroxide, improve hydrogenation efficiency and the concentration of hydrogen peroxide in working fluid, thereby be conducive to improve hydrogen peroxide unit production capacity and reduce process cost.
Current methylcyclohexyl acetate has all been realized suitability for industrialized production at home and abroad, domestic production producer mainly comprises Shanghai Supeng Industry Co., Ltd, Huzhou Jichang Chemical Co., Ltd. and Jiangmen Hydrogen Peroxide Solution Co., Ltd. etc., and Liming chemical Inst has also carried out relevant research.At present, methylcyclohexyl acetate preparation method is methyl-cyclohexanol route, adopts ortho-cresol hydrogenation synthesizing methyl hexalin, then under the existence of catalyzer and organic reaction solvent, makes methyl-cyclohexanol and acetic acid or acetic anhydride synthesis of acetic acid methyl cyclohexyl.As Chinese patent CN1240663C and CN101544563A all disclose a kind of preparation method by methyl-cyclohexanol and acetic acid or acetic anhydride synthesis of acetic acid methyl cyclohexyl.The raw material of these methods is difficult to obtain as methyl-cyclohexanol or methylphenol, expensive, causes methylcyclohexyl acetate production cost higher.
Summary of the invention
The object of the present invention is to provide a kind of raw material cheap and easy to get, cost is low, the good in economic efficiency method of being prepared methylcyclohexyl acetate by toluene.
The object of the invention is to be achieved through the following technical solutions:
A kind of method of being prepared methylcyclohexyl acetate by toluene, the method comprises the steps: (1) hydrogenation reaction: toluene and hydrogen carry out selective hydrogenation in hydrogenator, and hydrogenation products comprises toluene, tetrahydrotoluene and methylcyclohexane; (2) hydrogenation products separates: toluene, tetrahydrotoluene and methyl cyclohexane alkylating mixture after hydrogenation reaction are through separating, can be divided into toluene fraction, methylcyclohexane cut and tetrahydrotoluene cut, wherein, toluene loops back hydrogenator, and methylcyclohexane is as one of product; (3) esterification: tetrahydrotoluene generates methylcyclohexyl acetate with acetic acid generation esterification in esterifier; (4) esterification products separates: methylcyclohexyl acetate, acetic acid and a small amount of tetrahydrotoluene after esterification, through separating, can obtain methylcyclohexyl acetate product, and acetic acid and tetrahydrotoluene loop back esterifier and continue reaction.
The described method of being prepared methylcyclohexyl acetate by toluene, wherein, attached separating step comprises the separation of tetrahydrotoluene and separating of methylcyclohexyl acetate after esterification after hydrogenation reaction, these attached separation can adopt conventional tripping device to meet the demands, and its technique and operating parameters all can be with reference to similar process parameter controls.Therefore, in the present invention, to described purification condition, there is no particular limitation.
According to the inventive method, described hydrogenation reaction,, under catalyzer and reaction conditions, toluene contacts in hydrogenator with hydrogen, and hydrogenation products is the mixture of toluene, tetrahydrotoluene and methylcyclohexane.This reaction adopts noble metal catalyst, under reaction modifier effect, carries out, and reactor and reactive mode can adopt autoclave continuous hydrogenation reaction process, also can adopt tubular type continuous hydrogenation reaction process.
According to the inventive method, toluene hydrogenation reaction preferably adopts autoclave process for selective hydrogenation, under hydrogenation catalyst and properties-correcting agent effect, and reaction pressure 3-8MPa, temperature of reaction 130-170 DEG C, reacting slurry and toluene feed volume ratio 1-5:1, stir speed (S.S.) 600-1200 rev/min, under the condition of residence time 5-60 minute, carry out hydrogenation reaction, hydrogenation products is the mixture of toluene, tetrahydrotoluene and methylcyclohexane.
The method of hydrotreating according to the present invention, described reacting slurry is the mixture of hydrogenation catalyst, properties-correcting agent and water, wherein, in reacting slurry, catalyst content is 0.2-3.6 quality %, modifier content 10-40 quality %.
The method of hydrotreating according to the present invention, described hydrogenation catalyst comprises active ingredient element and adjuvant component element, active ingredient element is Ru; Adjuvant component element is one or more in Zn, Fe, La, Ce, Co.Wherein, the mol ratio of adjuvant component element and active ingredient element is 1:1-15, adopts conventional intermediate processing preparation.
The method of hydrotreating according to the present invention, described properties-correcting agent is ZnSO 4, FeSO 4, CoSO 4in one or more.
According to the inventive method, described esterification,, under catalyzer and reaction conditions, tetrahydrotoluene contacts with acetic acid in esterifier, and tetrahydrotoluene and acetic acid generation esterification generate methylcyclohexyl acetate.This reaction can adopt successive reaction, and as catalytic distillation reactor, catalyzer adopts solid acid, as storng-acid cation exchange resin, solid super-strong acid, heteropolyacid or molecular sieve etc.This reaction also can adopt rhythmic reaction, and as tank reactor, catalyzer can adopt liquid acid, as sulfuric acid, ionic liquid etc., also can adopt solid acid, as storng-acid cation exchange resin, solid super-strong acid, heteropolyacid or molecular sieve etc.
According to esterifying reaction method of the present invention, the esterification of tetrahydrotoluene and acetic acid can be implemented according to conventional olefin(e) acid esterification condition.For the inventive method, the esterification of tetrahydrotoluene and acetic acid is carried out in tank reactor, catalyzer adopts solid acid, preferably storng-acid cation exchange resin, under following reaction conditions, implement: temperature 80-140 DEG C, time 0.5-6 hour, catalyst content is 0.5-10 quality %, acetic acid and tetrahydrotoluene mol ratio are 2-6:1.
For the inventive method, the esterification of tetrahydrotoluene and acetic acid is preferentially carried out in catalytic distillation reactor, and catalyzer adopts solid acid catalyst, preferably storng-acid cation exchange resin.Described catalytic distillation reactor comprises a tower reactor, a stripping section, a conversion zone, a rectifying section and a trim the top of column condenser, filling solid acid catalyst in conversion zone, tetrahydrotoluene and acetic acid counter current contact on catalyzer, its operational condition is: tower top pressure 0.2-0.9MPa, tower top temperature 50-90 DEG C, conversion zone middle part temperature 80-120 DEG C, tower reactor temperature 120-180 DEG C, reflux ratio 0.2-8.0, the mol ratio of acetic acid and tetrahydrotoluene is 2-8, and acetic acid feed air speed is 0.2-10h -1.
Described strong acid cation exchange resin catalyst need carry out pre-treatment according to means known in the art before use.
The inventive method can realize by toluene prepares methylcyclohexyl acetate, and compared with methyl-cyclohexanol alcohol route, raw material is cheap and easy to get, and cost advantage is larger, has good economic benefit.
Brief description of the drawings
Fig. 1 is process flow sheet of the present invention.
Embodiment
Technical process is below by way of embodiments and drawings elaborated to the specific embodiment of the present invention and implementation result.Should be understood that, for those of ordinary skills, can be improved according to the above description or convert, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.
Embodiment 1-5 is toluene Hydrogenation methyl cyclohexane alkene reaction.
embodiment 1
In tank reactor, carry out toluene Hydrogenation methyl cyclohexane alkene reaction, reacting slurry and toluene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and toluene is 3:1, in reacting slurry, catalyst content is 0.8 quality % (Zn/Ru mol ratio is 1:8), ZnSO 4concentration is 15 quality %.Hydrogenation conditions is: reaction pressure 4MPa, 140 DEG C of temperature of reaction, 800 revs/min of stir speed (S.S.)s and 20 minutes residence time, what hydrogenation products was continuous enters product surge tank from high-pressure hydrogenation still, and it is for the oil phase containing toluene, tetrahydrotoluene, methylcyclohexane and containing catalyzer and ZnSO 4water, after oily water separation, containing catalyzer, ZnSO 4loop back high-pressure hydrogenation still with the reacting slurry of water and continue to participate in reaction, toluene, tetrahydrotoluene and methylcyclohexane enter products pot.Known by analysis, toluene accounts for 65 quality %, and tetrahydrotoluene accounts for 28 quality %, and all the other are methylcyclohexane.Wherein, 3-tetrahydrotoluene accounts for 19 quality %, and 4-tetrahydrotoluene accounts for 8 quality %, and 1-tetrahydrotoluene accounts for 1 quality %.
embodiment 2
In tank reactor, carry out toluene Hydrogenation methyl cyclohexane alkene reaction, reacting slurry and toluene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and toluene is 5:1, in reacting slurry, catalyst content is 3.6 quality % (Ce/Ru mol ratio is 1:4), ZnSO 4concentration is 30 quality %.Hydrogenation conditions is: reaction pressure 7MPa, 170 DEG C of temperature of reaction, 1200 revs/min of stir speed (S.S.)s and 5 minutes residence time, what hydrogenation products was continuous enters product surge tank from high-pressure hydrogenation still, and it is for the oil phase containing toluene, tetrahydrotoluene, methylcyclohexane and containing catalyzer and ZnSO 4water, after oily water separation, containing catalyzer, ZnSO 4loop back high-pressure hydrogenation still with the reacting slurry of water and continue to participate in reaction, toluene, tetrahydrotoluene and methylcyclohexane enter products pot.Known by analysis, toluene accounts for 50 quality %, and tetrahydrotoluene accounts for 38 quality %, and all the other are methylcyclohexane.Wherein, 3-tetrahydrotoluene accounts for 25 quality %, and 4-tetrahydrotoluene accounts for 2 quality %, and 1-tetrahydrotoluene accounts for 11 quality %.
embodiment 3
In tank reactor, carry out toluene Hydrogenation methyl cyclohexane alkene reaction, reacting slurry and toluene enter autoclave continuously, wherein, the volumetric flow rate ratio of reacting slurry and toluene is 1:1, in reacting slurry, catalyst content is 0.2 quality % (Co/Ru mol ratio is 1:15), CoSO 4concentration is 10 quality %.Hydrogenation conditions is: reaction pressure 3MPa, 130 DEG C of temperature of reaction, 600 revs/min of stir speed (S.S.)s and 60 minutes residence time, what hydrogenation products was continuous enters product surge tank from high-pressure hydrogenation still, and it is for the oil phase containing toluene, tetrahydrotoluene, methylcyclohexane and containing catalyzer and CoSO 4water, after oily water separation, containing catalyzer, CoSO 4loop back high-pressure hydrogenation still with the reacting slurry of water and continue to participate in reaction, toluene, tetrahydrotoluene and methylcyclohexane enter products pot.Known by analysis, toluene accounts for 60 quality %, and tetrahydrotoluene accounts for 27 quality %, and all the other are methylcyclohexane.Wherein, 3-tetrahydrotoluene accounts for 16 quality %, and 4-tetrahydrotoluene accounts for 10 quality %, and 1-tetrahydrotoluene accounts for 1 quality %.
embodiment 4
In tank reactor, carry out toluene Hydrogenation methyl cyclohexane alkene reaction, reacting slurry and toluene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and toluene is 4:1, in reacting slurry, catalyst content is 2.4 quality % (Fe/Ru mol ratio is 1:1), FeSO 4concentration is 40 quality %.Hydrogenation conditions is: reaction pressure 8MPa, 140 DEG C of temperature of reaction, 1000 revs/min of stir speed (S.S.)s and 15 minutes residence time, what hydrogenation products was continuous enters product surge tank from high-pressure hydrogenation still, and it is for the oil phase containing toluene, tetrahydrotoluene, methylcyclohexane and containing catalyzer and FeSO 4water, after oily water separation, containing catalyzer, FeSO 4loop back high-pressure hydrogenation still with the reacting slurry of water and continue to participate in reaction, toluene, tetrahydrotoluene and methylcyclohexane enter products pot.Known by analysis, toluene accounts for 60 quality %, and tetrahydrotoluene accounts for 34 quality %, and all the other are methylcyclohexane.Wherein, 3-tetrahydrotoluene accounts for 9 quality %, and 4-tetrahydrotoluene accounts for 22 quality %, and 1-tetrahydrotoluene accounts for 3 quality %.
embodiment 5
In tank reactor, carry out toluene Hydrogenation methyl cyclohexane alkene reaction, reacting slurry and toluene enter autoclave continuously, wherein, the volumetric flow rate ratio of reacting slurry and toluene is 3:1, in reacting slurry, catalyst content is 0.9 quality % (La/Ru mol ratio is 1:12), CoSO 4concentration is 11 quality %.Hydrogenation conditions is: reaction pressure 6MPa, 146 DEG C of temperature of reaction, 900 revs/min of stir speed (S.S.)s and 17 minutes residence time, what hydrogenation products was continuous enters product surge tank from high-pressure hydrogenation still, and it is for the oil phase containing toluene, tetrahydrotoluene, methylcyclohexane and containing catalyzer and CoSO 4water, after oily water separation, containing catalyzer, CoSO 4loop back high-pressure hydrogenation still with the reacting slurry of water and continue to participate in reaction, toluene, tetrahydrotoluene and methylcyclohexane enter products pot.Known by analysis, toluene accounts for 63 quality %, and tetrahydrotoluene accounts for 30 quality %, and all the other are methylcyclohexane.Wherein, 3-tetrahydrotoluene accounts for 20 quality %, and 4-tetrahydrotoluene accounts for 9 quality %, and 1-tetrahydrotoluene accounts for 1 quality %.
embodiment 6-13
Embodiment 6-13 is the esterification of acetic acid and tetrahydrotoluene.Wherein, embodiment 6-9 is in catalytic distillation tower, and tetrahydrotoluene contacts respectively from acetic acid on different solid acid catalyst surfaces, and through the synthetic corresponding methylcyclohexyl acetate of catalytic esterification, concrete data are in table 1; Embodiment 10-13 is the acetic acid that carries out in tank reactor and the esterification of tetrahydrotoluene, and concrete data are in table 2.
table 1acetic acid and tetrahydrotoluene catalytic distillation synthesis of acetic acid methyl cyclohexyl
table 2acetic acid and tetrahydrotoluene still reaction synthesis of acetic acid methyl cyclohexyl

Claims (2)

1. prepared the method for methylcyclohexyl acetate by toluene for one kind, it is characterized in that: comprise the steps: (1) hydrogenation reaction: toluene and hydrogen carry out selective hydrogenation in hydrogenator, hydrogenation products comprises toluene, tetrahydrotoluene and methylcyclohexane, wherein, described toluene hydrogenation reaction adopts autoclave continuous hydrogenation mode, reaction conditions is: reaction pressure 3-8MPa, temperature of reaction 130-170 DEG C, reacting slurry and toluene feed volume ratio 1-5:1, stir speed (S.S.) 600-1200 rev/min, toluene is residence time 5-60 minute in reactor; Described reacting slurry is the mixture of hydrogenation catalyst, properties-correcting agent and water, and wherein, catalyst content is 0.2-3.6 quality %, modifier content 10-40 quality %; Described properties-correcting agent is ZnSO 4, FeSO 4, CoSO 4in one or more; The catalyst activity component element that described hydrogenation reaction adopts is Ru, and adjuvant component element is one or more in Zn, Fe, La, Ce, Co, and the mol ratio of adjuvant component element and active ingredient element is 1:1-15; (2) hydrogenation products separates: toluene, tetrahydrotoluene and methyl cyclohexane alkylating mixture after hydrogenation reaction are through separating, can be divided into toluene fraction, methylcyclohexane cut and tetrahydrotoluene cut, wherein, toluene loops back hydrogenator, and methylcyclohexane is as one of product; (3) esterification: tetrahydrotoluene generates methylcyclohexyl acetate with acetic acid generation esterification in esterifier, and wherein, described esterifier is catalytic distillation reactor, and the catalyzer that described esterification adopts is solid acid; (4) esterification products separates: methylcyclohexyl acetate, acetic acid and a small amount of tetrahydrotoluene after esterification, through separating, can obtain methylcyclohexyl acetate product, and acetic acid and tetrahydrotoluene loop back esterifier and continue reaction.
2. method according to claim 1, it is characterized in that: described catalytic distillation reactor comprises a tower reactor, a stripping section, a conversion zone, a rectifying section and a trim the top of column condenser, filling solid acid catalyst in conversion zone, its operational condition is: tower top pressure 0.2-0.9MPa, tower top temperature 50-90 DEG C, conversion zone middle part temperature 80-120 DEG C, tower reactor temperature 120-180 DEG C, reflux ratio 0.2-8.0, the mol ratio of acetic acid and tetrahydrotoluene is 2-8, and acetic acid feed air speed is 0.2-10h -1.
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