CN103254038B - Method for preparing cyclohexanol by using benzene - Google Patents
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- CN103254038B CN103254038B CN201310135408.5A CN201310135408A CN103254038B CN 103254038 B CN103254038 B CN 103254038B CN 201310135408 A CN201310135408 A CN 201310135408A CN 103254038 B CN103254038 B CN 103254038B
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Abstract
The invention provides a method for preparing cyclohexanol by using benzene. The method comprises the following steps of: (1) a benzene hydrogenation reaction, (2) an olefine acid esterification reaction, (3) esterification product separation, (4) a cyclohexane dehydrogenation reaction, (5) a cyclohexyl acetate hydrogenation reaction and (6) cyclohexyl acetate hydrogenation product separation. According to the method, the preparation of cyclohexanol by using benzene and the preparation of alcohol by using acetic acid are realized, the generation of cyclohexane is avoided, and the extractive distillation separation of benzene, cyclohexene and cyclohexane is omitted, so that the investment of equipment and the energy consumption for separation are remarkably lowered.
Description
Technical field
The invention belongs to chemical production field, be specifically related to a kind of method of being produced hexalin by benzene.
Background technology
Hexalin a kind of excellent in high boiling Organic chemical products, have a wide range of applications in the every field of Chemical Manufacture.Hexalin mainly for the production of hexanolactam and hexanodioic acid, and then for the production of nylon-6 and nylon-66.Hexalin is also the main raw material preparing various ethenoid resin paint, and is widely used as the solvent of high molecular polymer, and for the preparation of softening agent, sterilant and spices etc.Therefore, hexalin has important application and market widely in organic chemical industry's industry, coating, textile industry etc.
Along with the development of benzene selective hydrogen addition technology, have also been obtained larger development by preparing cyclohexanol by cyclohexene hydration reaction technique.First benzene carry out selective hydrogenation, obtains the mixture of benzene, tetrahydrobenzene and hexanaphthene, and mixture obtains tetrahydrobenzene through three tower extracting rectifyings, and then tetrahydrobenzene carries out hydration reaction and obtains hexalin.The part but the method also comes with some shortcomings, tetrahydrobenzene is through that extracting rectifying obtains, and facility investment and separating energy consumption are all comparatively large, operation more complicated; In addition, owing to being subject to thermodynamic (al) restriction, cyclohexene hydration reaction speed is slow, and hexalin yield is too low, goes back a small amount of methyl cyclopentene of by-product, methylcyclopentanol, dimerization hexalin and cyclohexyl ether etc. simultaneously.CN101851151A discloses a kind of method being prepared hexalin by tetrahydrobenzene, the method is in same reactor, under carboxylic acid and molecular sieve catalyst exist, first esterification is carried out at certain condition by tetrahydrobenzene and carboxylic acid, then a certain amount of water is added, change reaction conditions proceeds hydrolysis reaction and prepares hexalin, but the method cyclohexene conversion rate is low, product more complicated, later separation difficulty.
Summary of the invention
The object of the invention is for overcoming the deficiencies in the prior art, a kind of novel method of being produced hexalin by benzene is provided.
The object of the invention is to be achieved through the following technical solutions:
The method of hexalin is produced, the method comprises the steps: (1) benzene hydrogenation: benzene and hydrogen carry out selective hydrogenation in hydrogenator, and hydrogenation products comprises benzene, tetrahydrobenzene and hexanaphthene by benzene; (2) olefin(e) acid esterification: hydrogenation products is under catalyst action, and the tetrahydrobenzene in hydrogenation products and acetic acid generation esterification generate hexalin acetate; (3) esterification products is separated: the mixture of the hexalin acetate after esterification, acetic acid, benzene and hexanaphthene is through fractionation by distillation, and acetic acid loops back esterifier; (4) cyclohexane dehydrogenation reaction: do not participate in esterification react benzene together with hexanaphthene through dehydrogenation reactor, then loop back benzene hydrogenation device; (5) hexalin acetate hydrogenation reaction: in the presence of a hydrogenation catalyst, hexalin acetate contacts in hydrogenator with hydrogen, hydrogenation generates hexalin and ethanol; (6) hexalin acetate hydrogenation products is separated: the hexalin acetate after hydrogenation reaction, hexalin and alcohol mixture are through fractionation by distillation, and hexalin acetate loops back hexalin acetate hydrogenator.
Described method of being produced hexalin by benzene, wherein, the separation of hexalin acetate and being separated of hexalin after hexalin acetate hydrogenation reaction after attached separating step comprises esterification, these attached separation can adopt conventional water distilling apparatus to meet the demands, and its operating parameters all can refer to similar process parameter control.Therefore, in the present invention, to described purification condition, there is no particular limitation.
According to the inventive method, described benzene hydrogenation, namely under catalyzer and reaction conditions, benzene contacts in hydrogenator with hydrogen, and hydrogenation products is the mixture of benzene, tetrahydrobenzene and hexanaphthene.This reaction adopts noble metal catalyst, and carry out under reaction modifier effect, 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, benzene hydrogenation 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, carry out hydrogenation reaction under the condition of reacting slurry and benzene input material volume ratio 1-5:1, stir speed (S.S.) 600-1200 rev/min and residence time 5-40 minute, hydrogenation products is the mixture of benzene, tetrahydrobenzene and hexanaphthene.
According to method of hydrotreating of the present invention, described reacting slurry is the mixture of hydrogenation catalyst, properties-correcting agent and water, and wherein, in reacting slurry, hydrogenation catalyst agent content is 0.2-1.8 quality %, modifier content 10-30 quality %.
According to method of hydrotreating of the present invention, described hydrogenation catalyst comprises active ingredient element and adjuvant component element, and 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 ordinary method preparation.
According to method of hydrotreating of the present invention, described properties-correcting agent is ZnSO
4, FeSO
4, CoSO
4in one or more.
According to the inventive method, described olefin(e) acid esterification, namely hydrogenation products is under catalyzer and reaction conditions, contacts in esterifier with acetic acid, and the tetrahydrobenzene in hydrogenation products and acetic acid generation esterification generate hexalin 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 described hydrogenation products and acetic acid can be implemented according to the olefin(e) acid esterification condition of routine.For the inventive method, the esterification of hydrogenation products and acetic acid is preferably carried out in catalytic distillation reactor, and catalyzer is solid acid catalyst.
Described catalytic distillation reactor comprises a tower reactor, a stripping section, conversion zone, a rectifying section and a trim the top of column condenser, filling solid acid catalyst in conversion zone.Hydrogenation products and acetic acid counter current contact on a catalyst, its operational condition is: tower top pressure 0.2-0.9MPa, tower top temperature 50-90 DEG C, conversion zone middle portion temperature 80-120 DEG C, bottom temperature 120-180 DEG C, reflux ratio 0.2-8.0, the mol ratio of the tetrahydrobenzene in acetic acid and hydrogenation products is 2-8, and acetic acid feed air speed is 0.2-10h
-1.
The preferred storng-acid cation exchange resin of described solid acid catalyst, resin catalyst need carry out pre-treatment according to means known in the art before use.
According to the inventive method, described dehydrogenation reaction, namely, under catalyzer and reaction conditions, the benzene not participating in esterification reacting carries out dehydrogenation reaction through fixed-bed reactor together with hexanaphthene, loops back benzene hydrogenation device together with the benzene that unreacted benzene and cyclohexane dehydrogenation generate.This reaction can adopt platinum catalyst, also can adopt nickel catalyzator, or both improvement catalyzer.
For the inventive method, the dehydrogenation reaction of the mixture of hexanaphthene and benzene adopts loaded platinum catalyst, and Pt content is 0.1-0.8 quality %, and carrier is Al
2o
3, SiO
2, ZrO
2, TiO
2in one or more.The mixture of hexanaphthene and benzene without gas dilution, also can use gas dilution, as hydrogen, nitrogen, argon gas etc.
Dehydrogenation reaction method according to the present invention, the dehydrogenation reaction of the mixture of hexanaphthene and benzene can be implemented according to the dehydrogenation reaction conditions of routine, and therefore, in the present invention, to described dehydrogenation reaction conditions, there is no particular limitation.Under normal circumstances, described dehydrogenation reaction conditions can comprise: temperature of reaction is 360-480 DEG C, reaction pressure 0.1-3.0MPa, and air speed is 1-10h
-1.For the inventive method, the dehydrogenation reaction conditions of the mixture of hexanaphthene and benzene is preferably: temperature of reaction is 380-460 DEG C, reaction pressure 0.3-1MPa, in hexanaphthene, and air speed 3-9h
-1.Dehydrogenation feed preferably uses diluted in hydrogen, and hydrogen and raw material (mixture of hexanaphthene and benzene) volume ratio are 100-10000.
According to the inventive method, described hexalin acetate hydrogenation reaction, namely under hydrogenation catalyst and reaction conditions, hexalin acetate contacts in hydrogenator with hydrogen, generates hexalin and ethanol.This reaction can adopt rhythmic reaction, as autoclave, also can adopt successive reaction, and as fixed-bed reactor, catalyzer can adopt noble metal catalyst, as palladium, ruthenium etc., also can adopt non-precious metal catalyst, as copper or nickel etc.Under normal circumstances, described ester through hydrogenation reaction conditions can comprise: temperature of reaction is 100-300 DEG C, and reaction pressure is 0.1-20MPa, and the reaction times is 0.1-10 hour.
For the inventive method, the hydrogenation reaction of hexalin acetate is preferably carried out in fixed-bed reactor, adopts non-precious metal catalyst, the more preferably catalyzer of cupric.According to the inventive method, described hexalin acetate hydroconversion condition is temperature of reaction 180-280 DEG C, reaction pressure 0.1-10MPa, hydrogen and hexalin acetate mol ratio 4-400, ester air speed 0.1-1.5h
-1.
The inventive method can utilize benzene to produce hexalin to greatest extent, avoids the production of low value-added hexanaphthene, eliminates the separation of extractive distillation process of benzene, tetrahydrobenzene and hexanaphthene simultaneously, significantly reduce facility investment and separating energy consumption.In addition, acetic acid is also changed into alcohol product by the inventive method, for the serious superfluous acetic acid of production capacity provides new utilization ways, has good economic benefit.
Accompanying drawing explanation
Fig. 1 is process flow sheet of the present invention.
Embodiment
Process flow sheet is below by way of embodiments and drawings described in detail 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 improve and convert the protection domain that all should belong to claims of the present invention.
Embodiment 1-5 is preparing cyclohexene from benzene added with hydrogen reaction.
embodiment 1
Preparing cyclohexene from benzene added with hydrogen reaction is carried out in tank reactor, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene 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 6MPa, temperature of reaction 140 DEG C, stir speed (S.S.) 800 revs/min and 20 minutes residence time, hydrogenation products continuous print enters product surge tank from high-pressure hydrogenation still, and it is containing the oil phase of benzene, tetrahydrobenzene, hexanaphthene and containing catalyzer and ZnSO
4aqueous phase, after oily water separation, containing catalyzer, ZnSO
4loop back high-pressure hydrogenation still with the reacting slurry of water to continue to participate in reaction, benzene, tetrahydrobenzene and hexanaphthene enter products pot.Wherein benzene accounts for 47 quality %, and tetrahydrobenzene accounts for 44 quality %, and all the other are hexanaphthene.
embodiment 2
Preparing cyclohexene from benzene added with hydrogen reaction is carried out in tank reactor, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 5:1, in reacting slurry, catalyst content is 0.2 quality % (Co/Ru mol ratio is 1:15), CoSO
4concentration is 30 quality %.Hydrogenation conditions is: reaction pressure 8MPa, temperature of reaction 170 DEG C, stir speed (S.S.) 1200 revs/min and 5 minutes residence time, hydrogenation products continuous print enters product surge tank from high-pressure hydrogenation still, and it is containing the oil phase of benzene, tetrahydrobenzene, hexanaphthene and containing catalyzer and CoSO
4aqueous phase, after oily water separation, containing catalyzer, CoSO
4loop back high-pressure hydrogenation still with the reacting slurry of water to continue to participate in reaction, benzene, tetrahydrobenzene and hexanaphthene enter products pot.Wherein benzene accounts for 58 quality %, and tetrahydrobenzene accounts for 36 quality %, and all the other are hexanaphthene.
embodiment 3
Preparing cyclohexene from benzene added with hydrogen reaction is carried out in tank reactor, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 1:1, in reacting slurry, catalyst content is 1.8 quality % (Ce/Ru mol ratio is 1:1), ZnSO
4concentration is 10 quality %.Hydrogenation conditions is: reaction pressure 3MPa, temperature of reaction 130 DEG C, stir speed (S.S.) 600 revs/min and 40 minutes residence time, hydrogenation products continuous print enters product surge tank from high-pressure hydrogenation still, and it is containing the oil phase of benzene, tetrahydrobenzene, hexanaphthene and containing catalyzer and ZnSO
4aqueous phase, after oily water separation, containing catalyzer, ZnSO
4loop back high-pressure hydrogenation still with the reacting slurry of water to continue to participate in reaction, benzene, tetrahydrobenzene and hexanaphthene enter products pot.Wherein benzene accounts for 37 quality %, and tetrahydrobenzene accounts for 45 quality %, and all the other are hexanaphthene.
embodiment 4
Preparing cyclohexene from benzene added with hydrogen reaction is carried out in tank reactor, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 2:1, in reacting slurry, catalyst content is 0.4 quality % (Fe/Ru mol ratio is 1:4), FeSO
4concentration is 18 quality %.Hydrogenation conditions is: reaction pressure 5MPa, temperature of reaction 145 DEG C, stir speed (S.S.) 900 revs/min and 15 minutes residence time, hydrogenation products continuous print enters product surge tank from high-pressure hydrogenation still, and it is containing the oil phase of benzene, tetrahydrobenzene, hexanaphthene and containing catalyzer and FeSO
4aqueous phase, after oily water separation, containing catalyzer, FeSO
4loop back high-pressure hydrogenation still with the reacting slurry of water to continue to participate in reaction, benzene, tetrahydrobenzene and hexanaphthene enter products pot.Wherein benzene accounts for 52 quality %, and tetrahydrobenzene accounts for 41 quality %, and all the other are hexanaphthene.
embodiment 5
Preparing cyclohexene from benzene added with hydrogen reaction is carried out in tank reactor, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 3:1, in reacting slurry, catalyst content is 0.6 quality % (La/Ru mol ratio is 1:11), FeSO
4concentration is 24 quality %.Hydrogenation conditions is: reaction pressure 4.3MPa, temperature of reaction 147 DEG C, stir speed (S.S.) 1000 revs/min and 13 minutes residence time, hydrogenation products continuous print enters product surge tank from high-pressure hydrogenation still, and it is containing the oil phase of benzene, tetrahydrobenzene, hexanaphthene and containing catalyzer and FeSO
4aqueous phase, after oily water separation, containing catalyzer, FeSO
4loop back high-pressure hydrogenation still with the reacting slurry of water to continue to participate in reaction, benzene, tetrahydrobenzene and hexanaphthene enter products pot.Wherein benzene accounts for 57 quality %, and tetrahydrobenzene accounts for 35 quality %, and all the other are hexanaphthene.
embodiment 6-9
Embodiment 6-9 is the esterification of acetic acid and hydrogenation products (benzene, tetrahydrobenzene and hexanaphthene).In catalytic distillation tower, hydrogenation products and acetic acid are respectively in different solid acid catalysts counter current contact on the surface, and through catalytic esterification Synthesis of Cyclohexyl Acetate, concrete data are in table 1.
table 1acetic acid and tetrahydrobenzene catalytic distillation Synthesis of Cyclohexyl Acetate
embodiment 10-13
Embodiment 10-13 is that the fixed-bed dehydrogenation of benzene and cyclohexane mixtures reacts, and the mixture of benzene and hexanaphthene is dehydrogenation feed.Wherein, air speed is in the hexanaphthene in mixture, and hydrogen to oil volume ratio is the radiometer with hydrogen and volume of mixture.Reaction conditions and the results are shown in Table 2.
table 2the mixture dehydrogenation reaction result of benzene and hexanaphthene
embodiment 11-12
Embodiment 11 is that on copper containing catalyst, hexalin acetate Hydrogenation reacts for hexalin, the results are shown in Table 3; Embodiment 12 is that on nickel-containing catalyst, hexalin acetate Hydrogenation reacts for hexalin, the results are shown in Table 4.
table 3on copper catalyst, hexalin acetate Hydrogenation is for hexalin reaction result
table 4on nickel catalyzator, hexalin acetate Hydrogenation is for hexalin reaction result
Claims (5)
1. produced a method for hexalin by benzene, it is characterized in that: comprise the steps:
(1) benzene hydrogenation: adopt autoclave continuous hydrogenation mode, benzene and hydrogen carry out selective hydrogenation in tank reactor, hydrogenation products comprises benzene, tetrahydrobenzene and hexanaphthene: described benzene hydrogenation adopts autoclave continuous hydrogenation mode, reaction conditions is: reaction pressure 3-8MPa, temperature of reaction 130-170 DEG C, reacting slurry and benzene input material volume ratio 1-5: 1, stir speed (S.S.) 600-1200 rev/min and benzene residence time 5-40 minute in reactor;
(2) olefin(e) acid esterification: hydrogenation products is under catalyst action, and the tetrahydrobenzene in hydrogenation products and acetic acid esterification occur in catalytic distillation reactor and generates hexalin acetate; Described esterification is carried out in catalytic distillation reactor, catalytic distillation reactor comprises a tower reactor, a stripping section, conversion zone, a rectifying section and a trim the top of column condenser, strong acid cation exchange resin catalyst is loaded in conversion zone, its operational condition is: tower top pressure 0.2-0.9MPa, tower top temperature 50-90 DEG C, conversion zone middle portion temperature 80-120 DEG C, bottom temperature 120-180 DEG C, reflux ratio 0.2-8.0, the mol ratio of the tetrahydrobenzene in acetic acid and hydrogenation mix products is 2-8, and acetic acid feed air speed is 0.2-10h
-1;
(3) esterification products is separated: the mixture of the hexalin acetate after esterification, acetic acid, benzene and hexanaphthene is through fractionation by distillation, and acetic acid loops back esterifier;
(4) cyclohexane dehydrogenation reaction: do not participate in esterification react benzene together with hexanaphthene through dehydrogenation reactor, then loop back benzene hydrogenation device;
(5) hexalin acetate hydrogenation reaction: under the non-precious metal catalyst of cupric exists, hexalin acetate contacts in fixed-bed reactor with hydrogen, hydrogenation generates hexalin and ethanol, wherein, contact conditions is: temperature of reaction 180-280 DEG C, reaction pressure 0.1-10MPa, hydrogen and hexalin acetate mol ratio 4-400, ester air speed 0.1-1.5h
-1;
(6) hexalin acetate hydrogenation products is separated: the hexalin acetate after hydrogenation reaction, hexalin and alcohol mixture are through fractionation by distillation, and hexalin acetate loops back hexalin acetate hydrogenator.
2. method according to claim 1, is characterized in that: described reacting slurry is the mixture of hydrogenation catalyst, properties-correcting agent and water, and wherein, hydrogenation catalyst agent content is 0.2-1.8 quality %, modifier content 10-30 quality %, and properties-correcting agent is ZnSO
4, FeSO
4, CoSO
4in one or more.
3. method according to claim 2, it is characterized in that: the active ingredient element of described hydrogenation catalyst is Ru, adjuvant component element is one or more in Zn, Fe, La, Ce, Co, and wherein, the mol ratio of adjuvant component element and active ingredient element is 1:1-15.
4. method according to claim 1, is characterized in that: described dehydrogenation reaction adopts loaded platinum catalyst, and Pt content is 0.1-0.8 quality %, and carrier is Al
2o
3, SiO
2, ZrO
2, TiO
2in one or more.
5. method according to claim 4, is characterized in that: described dehydrogenation reaction conditions is: temperature of reaction is 380-460 DEG C, reaction pressure 0.3-1MPa, in hexanaphthene, and air speed 3-9h
-1, the volume ratio of carrier gas and mixing raw material is 100-10000.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR102008352B1 (en) | 2012-09-18 | 2019-08-07 | 차이나 페트로리움 앤드 케미컬 코포레이션 | Method and device for coproducing cyclohexanol and alkanol |
| CN103467244A (en) * | 2013-09-27 | 2013-12-25 | 河北美邦工程科技有限公司 | Technology using benzene to prepare cyclohexanol |
| CN104557465A (en) * | 2013-10-25 | 2015-04-29 | 中国石油化工股份有限公司 | Method for coproducing cyclohexanol and alkanol |
| CN110105208A (en) * | 2019-06-11 | 2019-08-09 | 中触媒新材料股份有限公司 | A method of preparing cyclohexyl acetate |
| CN114075095B (en) * | 2020-08-18 | 2024-01-16 | 中石化南京化工研究院有限公司 | Comprehensive utilization method of hydrogen in caprolactam production |
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| CN1639090A (en) * | 2002-03-06 | 2005-07-13 | 巴斯福股份公司 | Method for the production of cyclohexanol from benzole |
| CN101851151A (en) * | 2010-05-17 | 2010-10-06 | 河北工业大学 | Method for preparing cyclohexanol by using cyclohexene |
| CN102875371A (en) * | 2012-10-29 | 2013-01-16 | 开滦能源化工股份有限公司 | Method for synthesizing cyclohexyl acetate from cyclohexene |
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| CN86105765A (en) * | 1985-07-23 | 1987-01-28 | Bp化学有限公司 | Method by carboxylicesters hydrogenation preparing alcohol |
| CN1639090A (en) * | 2002-03-06 | 2005-07-13 | 巴斯福股份公司 | Method for the production of cyclohexanol from benzole |
| CN101851151A (en) * | 2010-05-17 | 2010-10-06 | 河北工业大学 | Method for preparing cyclohexanol by using cyclohexene |
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