CN106349010A - Method for producing cyclohexanol - Google Patents
Method for producing cyclohexanol Download PDFInfo
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- CN106349010A CN106349010A CN201510555503.XA CN201510555503A CN106349010A CN 106349010 A CN106349010 A CN 106349010A CN 201510555503 A CN201510555503 A CN 201510555503A CN 106349010 A CN106349010 A CN 106349010A
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- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
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- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
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- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
- C07C29/1285—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis of esters of organic acids
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
- C07D201/06—Preparation of lactams from or via oximes by Beckmann rearrangement from ketones by simultaneous oxime formation and rearrangement
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- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D223/10—Oxygen atoms attached in position 2
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- 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
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Abstract
The invention provides a method for preparing cyclohexanol from cyclohexyl carboxylate serving as raw material by performing an ester exchange reaction under a near critical or supercritical condition. According to the method, a catalyst is not used, reaction products do not need to be separated in the reaction process, and low alcohol-to-ester ratio can be adopted; furthermore, the method has the characteristics of high reaction rate, high conversion rate, high selectivity and simple aftertreatment.
Description
Technical field
The present invention relates to a kind of method producing Hexalin, particularly to one kind near critical or supercritical
Under the conditions of produce the method for Hexalin by ester exchange reaction.
Background technology
Hexalin is a kind of broad-spectrum industrial chemicals and solvent, such as Hexalin (ratio at high temperature
As 150 DEG C~300 DEG C) dehydration can be occurred to prepare cyclohexene.In numerous purposes of Hexalin,
Above all produce the main intermediate Ketohexamethylene of nylon 6.
Since nylon comes out, dupont, dsm, monsanto, basf, Sumitomo, the eastern beautiful, rising sun
The world-famous chemical companies such as chemical conversion are all devoted for years in the exploitation of Hexalin (ketone) production technology.
At present, the industrial process of Hexalin (ketone) has phenol hydrogenation method, cyclohexane oxidation process and hexamethylene
Alkene is hydrated method.
Phenol hydrogenation method is industrialized cyclohexanol production method earliest, due to being limited by starting phenol
Shortage and the expensive impact with unfavorable factors such as the easy carbon distributions of catalyst of noble metal hydrogenation catalyst,
New device does not typically adopt phenol hydrogenation method.Cyclohexane oxidation process is cyclohexanol production main at present
Method, the problem that the method exists is a lot, such as conversion ratio is relatively low, selectivity is poor, not environmentally,
Uneasy congruence.Due to there is these problems, Japanese Asahi Kasei Corporation develops and utilizes cyclohexene hydration
Prepare the new technology of Hexalin, this technological reaction mild condition, selectivity are very high, hydrogen consumption is lower, complete
Process does not almost have three waste discharge, and defect is that raw material must use highly purified cyclohexene, operating process
Complicated, conversion per pass is very low.
Ethyl cyclohexyl ester through hydrogenation is a kind of emerging cyclohexanol production method, although with hexamethylene before
Alcohol production method is compared, and the reaction conversion ratio of the method and selectivity are all very high, and technique and operation
Process is greatly simplified, but the cost of the requirement of hydrogenation reaction equipment, investment and operation is still higher,
In addition hydrogenation process also will necessarily consume hydrogen source.
Cn103232325a discloses one kind with cyclohexyl carboxylate as raw material, under catalytic condition, passes through
The method that ester exchange reaction prepares Hexalin.The ester exchange reaction of catalysis generally can be divided into enzyme and urges
Change, acid catalysiss and three kinds of base catalysiss, the existing document with regard to catalyzed transesterification focuses primarily upon life
Generation diesel oil.These documents show, biological enzyme is due to being difficult at present solve catalyst cost relatively
The high and easy problem inactivating, therefore in a short time still cannot industrial applications;Acid catalyzed reaction rate
Relatively slow, and also result in serious equipment corrosion and disposal of pollutants, reaction system using acid catalyst
In alcohol under acid catalysed conditions it may also happen that etherification reaction;Base catalysiss have reaction condition gentle,
The fast advantage of speed, but it is only applicable to the high raw material of purity, particularly can not contain in raw material acid and/
Or water, otherwise base catalyst can be had a negative impact.If additionally, adopting homogeneous catalysis, must
Must there are the post-processing steps such as neutralization, washing, drying, and heterogeneous catalysis (solid catalyst) is at present
Still in the commerical test stage, in document, have no the report of heterogeneous catalysis commercial Application.In addition, ester
Exchange reaction is balancing response, in the ester-exchange reaction of catalysis, needs partial reaction product
Separate or using higher alcohol ester than improving the conversion ratio of reaction.
Content of the invention
For aforementioned the deficiencies in the prior art, the present invention provides one kind with cyclohexyl carboxylate as raw material,
Under near critical or super critical condition, method that Hexalin is prepared by ester exchange reaction, the method does not make
With catalyst, do not separate product during the course of the reaction, using relatively low alcohol ester ratio, and can have
Reaction rate is fast, high conversion rate, selectivity are good, the simple feature of post processing.
The main contents of the present invention are as follows.
1. a kind of method producing Hexalin, comprising:
(1) near critical or postcritical under the conditions of, the unitary alkane of cyclohexyl carboxylate and c1~c6
There is ester exchange reaction in alcohol;With
(2) product of step (1) is carried out separating, obtain Hexalin.
2. according to 1 method it is characterised in that in step (1), described cyclohexyl carboxylate is
Cyclohexyl formate or cyclohexyl acetate.
3. according to aforementioned arbitrary method it is characterised in that in step (1), described c1~c6
Unitary alkanol be methanol or ethanol.
4. according to aforementioned arbitrary method it is characterised in that in step (1), reaction condition is:
Reaction temperature is 220 DEG C~300 DEG C, preferably 260 DEG C~280 DEG C;Reaction pressure be 2mpa~
25mpa, preferably 4mpa~10mpa.
5. according to aforementioned arbitrary method it is characterised in that in step (1), anti-using continuous way
Should, feed volume air speed is 0.1h-1~10h-1, preferably 0.2h-1~5h-1.
6. according to aforementioned arbitrary method it is characterised in that in step (1), alcohol and ester mole
Than for 1~50:1, preferably 1~10:1, more preferably 3~6:1.
7. according to aforementioned arbitrary method it is characterised in that in the product of step (1), containing
There is water and the mass fraction of water is less than 20%;In the product of preferred steps (1), containing water and
The mass fraction of water is 0.005%~10%;More preferably in the product of step (1), containing water
And the mass fraction of water is 0.01%~5%.
8. a kind of method producing Ketohexamethylene, including Ketohexamethylene is prepared by Hexalin it is characterised in that
Described Hexalin is obtained by any one of 1 to 7.
9. a kind of method producing caprolactam, prepares caprolactam including by Ketohexamethylene, and its feature exists
In method described in 8 for the described Ketohexamethylene is obtained.
10. a kind of method producing adipic acid, including adipic acid is prepared by Hexalin it is characterised in that
Described Hexalin is obtained by any one of 1 to 7.
Compared with prior art, the present invention has the advantage that.
1st, with cyclohexyl carboxylate as raw material, ester exchange reaction is occurred under near critical or super critical condition
Produce Hexalin, reaction rate, conversion ratio and selectivity are all very high;
2nd, with cyclohexyl carboxylate as raw material, ester exchange reaction is occurred under near critical or super critical condition
Produce Hexalin, do not require the use of catalyst, be not required to separate product in reaction, can adopt relatively low
Alcohol ester ratio, and last handling process is simple, the post-processing step producing the three wastes such as is not required to wash;
3rd, the technological equipment investment of ester exchange and operating cost are less than cyclohexyl carboxylate hydrogenation technique;
4th, for integrated artistic route, the hydrogen consumption of the present invention is lower;
Specific embodiment
In the present invention, ester exchange reaction refers to the ester group exchange reaction occurring between carboxylate and alcohol.
In the present invention, all pressure are gauge pressure.
In the context of the present specification, in addition to the content clearly stating, do not mention anything
Preferably or item be all directly suitable for known in the art those and any change need not be carried out.And, herein
Any embodiment of description all can with one or more other embodiment described herein freely
It is accordingly to be regarded as the original disclosure of the present invention or original description in conjunction with, the technical scheme being consequently formed or technological thought
A part, and be not considered as the new content not disclosing herein or expecting, unless this area
Technical staff thinks that this combination is substantially unreasonable.
Numerical point disclosed in this specification, not only includes specifically disclosed numerical point, also includes each number
The end points of value scope, the scope of these numerical point institute combination in any be regarded as the present invention disclosed or
Whether the scope recorded or technical characteristic, no matter separately disclose these numerical value pair herein.The present invention
Disclosed all features can in any combination, and these combinations should be understood presently disclosed or note
The content carrying, unless those skilled in the art think that this combination is substantially unreasonable.
Known in the art, there is ester exchange reaction at supercritical conditions using oils and fatss and methanol, permissible
Produce biodiesel.In general, this reaction needs to carry out at supercritical conditions, could obtain full
The result of meaning, and under the conditions of near critical (or claiming subcritical), the reaction rate of ester exchange is still relatively slow,
Such as when being in 200 DEG C~230 DEG C, temperature is not up to 239.4 DEG C of the critical temperature of methanol, now
Ester exchange reaction speed relatively low, the Oleum Brassicae campestriss that there are about 68%~70% after a hour change into fatty acid methyl
Ester;When temperature reaches 270 DEG C, the conversion ratio of Oleum Brassicae campestriss is not still high;And work as temperature reach 300 DEG C with
When upper, reaction rate significantly improves, and conversion ratio during four minutes can increase to 80%~95%.This area
It is also known that Hexalin is easy to dehydration, it is highly endothermic anti-that dehydration of cyclohexanol generates cyclohexene
Answer (reaction heat is 34.3kj/mol), therefore rise high-temperature and be conducive to dehydration of cyclohexanol to generate ring
Hexene, is often dehydrated, on laboratory or little rule using Hexalin in practice between 150 DEG C~300 DEG C
Cyclohexene is prepared on mould.The inventors discovered that, make under the hot conditionss of near critical or supercritical reaction
When cyclohexyl carboxylate occurs ester exchange reaction, side reaction is not almost had to occur, even and if near critical
Under conditions of, the ester exchange reaction speed of cyclohexyl carboxylate is still quite fast, this completes the present invention.
The invention provides a kind of method producing Hexalin, comprising:
(1) near critical or postcritical under the conditions of, the unitary alkane of cyclohexyl carboxylate and c1~c6
There is ester exchange reaction in alcohol;With
(2) product of step (1) is carried out separating, obtain Hexalin.
According to the present invention, described cyclohexyl carboxylate is preferably the ring of the straight-chain monobasic carboxylic acid of c1~c22
The cyclohexyl of the straight-chain monobasic carboxylic acid of own ester, more preferably c1~c10, more preferably formic acid ring
Own ester or cyclohexyl acetate.
According to the present invention, described near critical or postcritical condition may is that reaction temperature is
100 DEG C~400 DEG C, preferably 150 DEG C~350 DEG C, more preferably 200 DEG C~300 DEG C;Reaction pressure
Power is 0.5mpa~40mpa, preferably 1mpa~20mpa, more preferably 2mpa~16mpa.Excellent
Changing reaction condition is: reaction temperature is 220 DEG C~300 DEG C, preferably 260 DEG C~280 DEG C;Reaction
Pressure is 2mpa~25mpa, preferably 4mpa~10mpa.
According to the present invention, described near critical condition is: reaction temperature is 220 DEG C~280 DEG C, preferably
For 240 DEG C~280 DEG C;, for 4mpa to less than critical pressure, preferably 6mpa is extremely little for reaction pressure
In critical pressure.
According to the present invention, the mode of operation of step (1), batch (-type) both can be adopted it is also possible to adopt
Use continuous way.During using intermittent reaction, the response time is 0.1h~10h, preferably 0.5h~5h;
During using continuous reaction, Feed space velocities select 0.1h-1~10h-1, preferably 0.2h-1~5h-1.
According to the present invention, in step (1), tank reactor or tubular reactor can be adopted.
According to the present invention, in step (1), alcohol is 1~50:1 with the mol ratio of ester, preferably 2~
10:1, more preferably 3~6:1.
According to the present invention, in the product of step (1), containing water and the mass fraction of water is less than
20%;In the product of preferred steps (1), containing water and water mass fraction be 0.001%~
10%;More preferably in the product of step (1), containing water and water mass fraction be 0.01%~
5%.According to the present invention, the water in described product, be that raw material is brought into and/or course of reaction in
Produce.In the case of one kind, water in described product, is partly or entirely to produce in course of reaction
Raw.
According to the present invention, described cyclohexyl carboxylate is obtained by carboxylic acid and hexamethylene alkene reaction.
Present invention also offers with Hexalin as raw material, produce respectively Ketohexamethylene, caprolactam or oneself two
The method of acid, this partial content belongs to prior art, and the present invention repeats no more to this.
By the following examples, further illustrate the present invention.
Embodiment 1
By methanol (water content 0.079%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.35%,
Acetic acid content 0.023%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 8:1,250 DEG C,
5mpa and Feed space velocities are 1h-1Under conditions of react, collecting reaction product, analysis cyclohexyl acetate
Conversion ratio is 98.57%, and the selectivity of Hexalin is 99.38%, and water in products point content is 0.056%,
Ether content 0.02%, does not detect cyclohexene from product.
Embodiment 2
By methanol (water content 0.079%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.35%,
Acetic acid content 0.023%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 2:1,200 DEG C,
8mpa and Feed space velocities are 0.5h-1Under conditions of react, collecting reaction product, analyze cyclohexyl acetate
Conversion ratio be 94.42%, the selectivity of Hexalin is 99.83%, and water in products point content is
0.031%, ether content 0.03%, do not detect cyclohexene from product.
Embodiment 3
By methanol (water content 0.079%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.35%,
Acetic acid content 0.023%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 4:1,260 DEG C,
6mpa and Feed space velocities are 1.0h-1Under conditions of react, collecting reaction product, analyze cyclohexyl acetate
Conversion ratio be 99.23%, the selectivity of Hexalin is 99.54%, and water in products point content is
0.043%, ether content 0.02%, do not detect cyclohexene from product.
Embodiment 4
By methanol (water content 0.079%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.59%,
Acetic acid content 0.149%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 5:1,250 DEG C,
7mpa and Feed space velocities are 2.0h-1Under conditions of react, collecting reaction product, analyze cyclohexyl acetate
Conversion ratio be 99.38%, the selectivity of Hexalin is 99.34%, and water in products point content is
0.065%, ether content 0.02%, do not detect cyclohexene from product.
Under reaction mass same as before and proportioning, identical reaction condition, with carbon steel test piece detection
The corrosivity of reaction mass, result shows that corrosion is less than 0.075mm/a.
Embodiment 5
The cyclohexyl acetate that methanol and rectification are obtained pumps into tubular type according to the ratio of alcohol ester mol ratio 3:1
Reactor, is 1.5h in 250 DEG C, 16mpa and Feed space velocities-1Under conditions of react, collect reaction
Product, the conversion ratio of analysis cyclohexyl acetate is 97.42%, and the selectivity of Hexalin is 99.47%,
Ether content 0.02% in product, does not detect cyclohexene from product.
Embodiment 6
The cyclohexyl acetate that methanol and rectification are obtained pumps into pipe according to the ratio of alcohol ester mol ratio 10:1
Formula reactor, is 5h in 300 DEG C, 12mpa and Feed space velocities-1Under conditions of react, collect reaction
Product, the conversion ratio of analysis cyclohexyl acetate is 99.70%, and the selectivity of Hexalin is 98.35%,
Ether content 0.03% in product, does not detect cyclohexene from product.
Embodiment 7
By methanol (water content 1.253%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.59%,
Acetic acid content 0.149%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 5:1,260 DEG C,
5mpa and Feed space velocities are 2h-1Under conditions of react, collecting reaction product, analysis cyclohexyl acetate
Conversion ratio is 99.57%, and the selectivity of Hexalin is 99.23%, and water in products point content is 0.67%,
Ether content 0.03%, does not detect cyclohexene from product.
Embodiment 8
By methanol (water content 1.253%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.59%,
Acetic acid content 0.149%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 6:1,260 DEG C,
2mpa and Feed space velocities are 0.5h-1Under conditions of react, collecting reaction product, analyze cyclohexyl acetate
Conversion ratio be 96.37%, the selectivity of Hexalin is 99.65%, and water in products point content is 0.73%,
Ether content 0.02%, does not detect cyclohexene from product.
Embodiment 9
By ethanol (water content 0.434%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.35%,
Acetic acid content 0.023%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 4:1,260 DEG C,
6mpa and Feed space velocities are 1.0h-1Under conditions of react, collecting reaction product, analyze cyclohexyl acetate
Conversion ratio be 98.23%, the selectivity of Hexalin is 99.65%, and water in products point content is 0.24%,
Ether content 0.03%, does not detect cyclohexene from product.
Embodiment 10
By ethanol (water content 0.434%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.59%,
Acetic acid content 0.149%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 3:1,220 DEG C,
10mpa and Feed space velocities are 3h-1Under conditions of react, collecting reaction product, analyze cyclohexyl acetate
Conversion ratio be 97.39%, the selectivity of Hexalin is 99.78%, and water in products point content is 0.23%,
Ether content 0.04%, does not detect cyclohexene from product.
Under reaction mass same as before and proportioning, identical reaction condition, with carbon steel test piece detection
The corrosivity of reaction mass, result shows that corrosion is less than 0.075mm/a.
Embodiment 11
By ethanol (water content 5.264%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.35%,
Acetic acid content 0.023%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 4:1,280 DEG C,
5mpa and Feed space velocities are 1.0h-1Under conditions of react, collecting reaction product, analyze cyclohexyl acetate
Conversion ratio be 93.83%, the selectivity of Hexalin is 99.54%, and water in products point content is 2.59%,
Ether content 0.03%, does not detect cyclohexene from product.
Embodiment 12
By ethanol (water content 5.264%) and cyclohexyl acetate (ethyl cyclohexyl ester content is 99.59%,
Acetic acid content 0.149%) pump into tubular reactor according to the ratio of alcohol ester mol ratio 5:1,240 DEG C,
8mpa and Feed space velocities are 2h-1Under conditions of react, collecting reaction product, analysis cyclohexyl acetate
Conversion ratio is 94.11%, and the selectivity of Hexalin is 99.49%, and water in products point content is 3.26%,
Ether content 0.03%, does not detect cyclohexene and acetic acid from product.
Embodiment 13
The methanol using is the super dry methanol that firsthand water content is 28 μ g/g, cyclohexyl acetate
The cyclohexyl acetate then obtaining for rectification, first uses sodium carbonate and calcium chloride deacidification, eliminating water, then steaming of reducing pressure
Evaporate the smart cyclohexyl acetate without acetic acid and water obtaining.The smart acetic acid that super dry methanol and rectification are obtained
Cyclohexyl pumps into tubular reactor according to the ratio of alcohol ester mol ratio 4:1, in 260 DEG C, 6mpa and entering
Material air speed is 1h-1Under conditions of react, collecting reaction product, analysis cyclohexyl acetate conversion ratio be
87.63%, the selectivity of Hexalin is 99.32%, and water in products point content is 0.003%, ether content
0.02%, do not detect cyclohexene from product.
Claims (12)
1. a kind of method producing Hexalin, comprising:
(1) near critical or postcritical under the conditions of, the unitary alkane of cyclohexyl carboxylate and c1~c6
There is ester exchange reaction in alcohol;With
(2) product of step (1) is carried out separating, obtain Hexalin.
2. in accordance with the method for claim 1 it is characterised in that in step (1), described
Cyclohexyl carboxylate is cyclohexyl formate or cyclohexyl acetate.
3. in accordance with the method for claim 1 it is characterised in that in step (1), described c1~
The unitary alkanol of c6 is methanol or ethanol.
4. in accordance with the method for claim 1 it is characterised in that in step (1), reacting bar
Part is: reaction temperature is 220 DEG C~300 DEG C;Reaction pressure is 2mpa~25mpa.
5. in accordance with the method for claim 1 it is characterised in that in step (1), reaction is warm
Spend for 220 DEG C~280 DEG C;Reaction pressure is 4mpa to less than critical pressure.
6. in accordance with the method for claim 1 it is characterised in that in step (1), using even
Continuous formula reaction, feed volume air speed is 0.2h-1~5h-1.
7. in accordance with the method for claim 1 it is characterised in that in step (1), alcohol and ester
Mol ratio be 3~6:1.
8. in accordance with the method for claim 1 it is characterised in that the product of step (1)
In, containing water and water mass fraction be less than 20%.
9. in accordance with the method for claim 1 it is characterised in that the product of step (1)
In, containing water and water mass fraction be 0.01%~5%.
10. a kind of method producing Ketohexamethylene, including Ketohexamethylene is prepared by Hexalin it is characterised in that
Described Hexalin is obtained by any one of claim 1 to 9.
A kind of 11. methods producing caprolactam, prepare caprolactam including by Ketohexamethylene, its feature
It is, method described in 10 for the described Ketohexamethylene is obtained.
A kind of 12. methods producing adipic acid, including adipic acid is prepared by Hexalin it is characterised in that
Described Hexalin is obtained by any one of claim 1 to 9.
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CN114621052A (en) * | 2020-12-10 | 2022-06-14 | 中国科学院大连化学物理研究所 | Method and device for industrially preparing cyclohexanol |
CN114621051A (en) * | 2020-12-10 | 2022-06-14 | 中国科学院大连化学物理研究所 | Method and device for industrially preparing cyclohexanol |
CN114621077A (en) * | 2020-12-10 | 2022-06-14 | 中国科学院大连化学物理研究所 | Method and equipment for industrially preparing adipic acid |
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