CN108250044A - A kind of preparation method and application of alkyl cyclohexanol - Google Patents
A kind of preparation method and application of alkyl cyclohexanol Download PDFInfo
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Abstract
The invention belongs to catalytic hydrogenation fields, more particularly to a kind of method of alkyl phenol catalytic hydrogenation production alkyl cyclohexanol, alkyl phenol is used as raw material, under the action of ruthenium-based catalyst, using batch still catalytic hydrogenation process, alkyl phenol hydrogenation reaction is carried out under certain temperature, certain pressure, certain air speed, obtains alkyl cyclohexanol.The active component of catalyst is Ru in the present invention, and content 1%, auxiliary agent is manganese, one kind in cobalt, nickel, and content is 1~3%, and carrier is one kind in zirconium oxide, titanium oxide, gamma-alumina and silica.
Description
Technical field
The invention belongs to catalytic hydrogenation fields, and in particular to a kind of to prepare alkyl cyclohexanol using alkyl phenol catalytic hydrogenation
Method.
Background technology
Alkylbenzene phenols environmental hormone is widely present in the daily necessitiess such as plastics, under certain conditions, alkylbenzene phenols
Environmental hormone may be moved in food, and various plastic products house refuses generated etc. of living along with people, phenol
Class environmental hormone can move in water body, soil from plastic products.Alkylbenzene phenols environmental hormone property is highly stable, in environment
In be difficult to be degraded, there is bioaccumulation and enlarge-effect, various countries put into effect regulation limitation containing induced by alkyl hydroxybenzene environmental hormone in succession
Product.By alkyl phenol Hydrogenation for alkyl cyclohexanol, the harm to environment can be effectively reduced, reduces the shadow to health
It rings.
Nonyl phenol (nonylphenol, abbreviation NP) is a kind of important fine chemical material and intermediate, is a kind of main
The mixture of various isomers being made of 4- nonyl phenols.Nonyl phenol category organic pollution has the title of " sperm killer ", there is research
It was found that the nonyl phenol of low concentration just can generate adverse effect to the reproductive system of animal, and bioconcentration then makes this influence
Aggravation.Nonyl phenol in water body is difficult to degrade, and has bioaccumulation, therefore it can be widely present in water environment.Due to
Nonyl phenol has excellent decontamination, moistening, dispersion and increase-volume emulsifiability etc., and the demand of domestic and international n nonylphenol is still very big,
And the nonyl cyclohexanol polyoxyethylene ether alcohol for studying the nonyl cyclohexanol preparation that acquisition is further reacted in discovery by nonyl phenol can be most
Big degree is close to the performance of nonylphenol polyoxyethylene ether.Had by the standby nonyl cyclohexanol of nonyl phenol Hydrogenation similar with nonyl phenol
As structure and performance, be produce nonionic surfactant important intermediate, have no environmental toxicity, inanimate object accumulation
Property, it is biodegradable the advantages of.
Chinese patent CN104151134A discloses a kind of method that nonyl phenol catalytic hydrogenation continuously prepares nonyl cyclohexanol,
Using nonyl phenol and hydrogen as raw material, using metallic nickel, palladium as active component, activated carbon, TiO2-SiO2And Al2O3For carrier, prepare
Hydrogenation catalyst is 250 DEG C, reaction pressure 6MPa in temperature, the volume space velocity of nonyl phenol solution is using fixed bed reactors
0.1h-1, hydrogen inlet amount is 40ml/min, carries out gas-liquid-solid three phase catalytic reaction, and nonyl phenol conversion ratio is 85.3%, selectivity
It is 97.7%.But the conversion ratio of reaction is low, and the by-product for still having 2% generates.
He Hongjun etc. prepares Pd (10%)/C catalyst, for propylphenol Hydrogenation for cyclohexyl alcohol (ketone), in hydrogen
Atmospheric pressure 1.5MPa at 160~170 DEG C of temperature, reacts 13~15h, catalytic activity 89.34%.But noble metal dosage is more, urges
Agent is of high cost, and the reaction time is long, and converts not fully.
Invention content
The purpose of the present invention is to provide a kind of equipment investment is small, hydrogen consumption is low, the few production alkyl of side reaction
The method of alcohol, and alkyl cyclohexanol is substituted into centre of the alkyl phenol as production surfactant alkyl cyclohexanol polyoxyethylene ether
Body, to reduce the pollution to environment and the influence to health.
The preparation of alkyl cyclohexanol of the present invention is to use alkyl phenol as raw material, under the action of ruthenium-based catalyst, between
It has a rest kettle catalytic hydrogenation process, is in temperature：120~180 DEG C, pressure is：Alkyl phenol hydrogenation reaction is carried out under 3~5MPa, is obtained
Alkyl cyclohexanol, wherein, the reaction response time is：4~6h, catalyst amount are：1~3%.
It can reach 100% using the conversion ratio of the method for the present invention alkyl phenol, performance be selected to reach 99.9%, product is pure
Degree is high, and noble metal dosage is low in catalyst, and hydrogen consumption is few, at low cost, and reaction condition is mild, and the reaction time is short.
Heretofore described ruthenium-based catalyst by mass percentage consisting of：Active component ruthenium is 1%, and auxiliary agent is
2%, remaining is carrier.Wherein, the auxiliary agent of catalyst is one kind in manganese, cobalt, nickel, preferably cobalt；Carrier is zirconium oxide, oxidation
One kind in titanium, gama-alumina or silica.
The preparation method of the ruthenium-based catalyst specifically carries out as steps described below：
(1) carrier of calculation amount is weighed, is added in ammonium dihydrogen phosphate and is pre-processed to obtain P Modification presoma；
Wherein, the mass concentration of the ammonium dihydrogen phosphate is 1~5%.
(2) soluble-salt of auxiliary agent with deionized water is configured to the soluble salt solutions of auxiliary agent, adds in the step of calculation amount
Suddenly (1) obtains P Modification presoma, stirs evenly, and ammonium hydroxide is added dropwise at 30 DEG C, and it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters,
110 DEG C of drying, Muffle kiln roasting 5 hours are ground up, sieved, obtain modified support；Wherein, the soluble-salt of auxiliary agent 30g water
Wiring solution-forming, calcination temperature are 300~600 DEG C.
(3) ruthenium trichloride for weighing calculation amount is made into solution of ruthenium trichloride, adds in through the modified carrier of step (2), stirring
Uniformly, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, and Muffle kiln roasting 5 is small
When, it is ground up, sieved, obtains catalyst precursor；Wherein, ruthenium trichloride 30g water wiring solution-formings, calcination temperature are 300~600
℃。
(4) catalyst precursor that step (4) obtains is put into atmospheric hydrogen in tube furnace to restore, temperature 100~600
DEG C, ruthenium-based catalyst was made in 3~6 hours time.
It is other that the ruthenium-based catalyst is suitable for nonyl phenol, octyl phenol, dodecylphenol, bisphenol-A, isophthalodinitrile etc.
The hydrogenation catalyst reaction of phenyl ring.
Auxiliary agent in catalyst of the present invention promotes the reduction of active component ruthenium-oxide, enhances Catalyst Adsorption hydrogen
Ability increases the specific surface area of active metal and the dispersion degree of metal, and then improves catalyst and the catalysis of alkyl phenol is added
Hydrogen effect, P Modification further improve active mutually in the dispersion degree of carrier surface, it is suppressed that the generation of non-active species changes
The distribution of catalyst surface acidic site.
The present invention also provides the applications of alkyl cyclohexanol prepared by the method, it is characterised in that：The alkane obtained
Cyclohexanol is used to prepare alkyl cyclohexanol polyoxyethylene ether.
Advantageous effect：
The high activated catalyst that the present invention uses, wherein, active component acts synergistically with auxiliary agent, can reduce the work of reaction
Change energy, reduce reaction condition, reduce side reaction, while use P Modification carrier, improve active mutually in carrier surface
Dispersion degree, it is suppressed that the generation of non-active species changes the distribution of catalyst surface B acid position.
Hydrogenation technique of the present invention, short with the reaction time, equipment investment is small, and hydrogen consumption is few, reacts target product yield
Alkyl cyclohexanol is substituted centre of the alkyl phenol as production surfactant alkyl cyclohexanol polyoxyethylene ether by the advantages of high
Body can reduce the pollution to environment and the influence to health.
Specific embodiment
The present invention is described in further detail with reference to embodiment：
Embodiment 1
5g silica is weighed, impregnates modified 8h, 110 DEG C of drying with 3% ammonium dihydrogen phosphate, 400 DEG C of roastings obtain phosphorus
Modified support weighs the Mn (NO of 0.7866g3)2·4H2O is dissolved in 30g distilled water, after ultrasonic dissolution, by 5g P Modification carriers
It is added in solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 300
DEG C roasting 5h, then weigh the ruthenium trichloride of 0.1351g and be dissolved in 30g distilled water, after ultrasonic dissolution, carrier is added to solution
In, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 300 DEG C of roasting 5h,
Washing removal Cl-, then hydrogen reducing under normal pressure, 300 DEG C of temperature, 5 hours time.Ru contents are that 1%, Mn contents are 2%.
Embodiment 2
5g titanium oxide is weighed, impregnates modified 8h, 110 DEG C of drying with 5% ammonium dihydrogen phosphate, 400 DEG C of roastings obtain phosphorus
Modified support weighs the Ni (NO of 0.2478g3)2·6H2O is dissolved in 30g distilled water, after ultrasonic dissolution, by 5g P Modification carriers
It is added in solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 400
DEG C roasting 5h, then weigh the ruthenium trichloride of 0.1351g and be dissolved in 30g distilled water, after ultrasonic dissolution, carrier is added to solution
In, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 400 DEG C of roasting 5h,
Washing removal Cl-, then hydrogen reducing under normal pressure, 600 DEG C of temperature, 6 hours time.Ru contents are that 1%, Ni contents are 2%.
Embodiment 3
5g gama-aluminas are weighed, impregnate modified 8h, 110 DEG C of drying with 3% ammonium dihydrogen phosphate, 400 DEG C of roastings obtain
To P Modification carrier, the Co (NO of 0.4939g are weighed3)2·6H2O is dissolved in 30g distilled water, after ultrasonic dissolution, by 5g P Modifications
Carrier is added in solution, and ammonium hydroxide is added dropwise at 30 DEG C, and it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, and 110 DEG C of drying are ground
Mill, 500 DEG C of roasting 5h, then weigh the ruthenium trichloride of 0.1351g and be dissolved in 30g distilled water, after ultrasonic dissolution, carrier is added to
In solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 500 DEG C of roastings
5h, washing removal Cl-, then hydrogen reducing under normal pressure, 500 DEG C of temperature, 3 hours time.Ru contents are that 1%, Co contents are 2%.
Embodiment 4
5g gama-aluminas are weighed, without modification, weigh the Co (NO of 0.4939g3)2·6H2O is dissolved in 30g distilled water,
After ultrasonic dissolution, 5g carriers are added in solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, is taken out
Filter, 110 DEG C of drying, grinding, 500 DEG C of roasting 5h, then weigh the ruthenium trichloride of 0.1351g and be dissolved in 30g distilled water, ultrasonic dissolution
Afterwards, carrier is added in solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of bakings
It is dry, grinding, 500 DEG C of roasting 5h, washing removal Cl-, then hydrogen reducing under normal pressure, 500 DEG C of temperature, 3 hours time.Ru contents are
1%, Co content are 2%.
Embodiment 5
5g gama-aluminas are weighed, impregnate modified 8h, 110 DEG C of drying with 3% ammonium dihydrogen phosphate, 400 DEG C of roastings obtain
To P Modification carrier, the Fe (NO of 0.7234g are weighed3)3·9H2O is dissolved in 30g distilled water, after ultrasonic dissolution, by 5g P Modifications
Carrier is added in solution, and ammonium hydroxide is added dropwise at 30 DEG C, and it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, and 110 DEG C of drying are ground
Mill, 600 DEG C of roasting 5h, then weigh the ruthenium trichloride of 0.1351g and be dissolved in 30g distilled water, after ultrasonic dissolution, carrier is added to
In solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 600 DEG C of roastings
5h, washing removal Cl-, then hydrogen reducing under normal pressure, 500 DEG C of temperature, 3 hours time.Ru contents are that 1%, Fe contents are 2%.
Embodiment 6
5g zirconium oxides are weighed, impregnate modified 8h, 110 DEG C of drying with 1% ammonium dihydrogen phosphate, 400 DEG C of roastings obtain phosphorus
Modified support weighs the Cu (NO of 0.191g3)2·3H2O is dissolved in 30g distilled water, and after ultrasonic dissolution, P Modification carrier is added in
Into solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 300 DEG C of roastings
5h is burnt, then weighs the ruthenium trichloride of 0.1351g and is dissolved in 30g distilled water, after ultrasonic dissolution, carrier is added in solution, 30
Ammonium hydroxide is added dropwise at DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, and 400 DEG C of roasting 5h, washing is gone
Except Cl-, then hydrogen reducing under normal pressure, 100 DEG C of temperature, 4 hours time.Ru contents are that 1%, Cu contents are 2%.
Embodiment 7
5g gama-aluminas are weighed, impregnate modified 8h, 110 DEG C of drying with 3% ammonium dihydrogen phosphate, 400 DEG C of roastings obtain
To P Modification carrier, the ruthenium trichloride for weighing 0.1351g is dissolved in 30g distilled water, and after ultrasonic dissolution, 5g P Modification carriers are added
Enter into solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, grinding, 500 DEG C
Roast 5h, washing removal Cl-, then hydrogen reducing under normal pressure, 500 DEG C of temperature, 3 hours time, Ru contents are 1%.
Embodiment 8
Using 25g nonyl phenols as raw material, under the action of 1 catalyst of 0.5g embodiments, using batch still catalytic hydrogenation process,
In 150 DEG C, pressure 4MPa of temperature, 6h is reacted, alkyl phenol conversion ratio is 76.8%, and selectivity is 94.5%.
Embodiment 9
Using 25g nonyl phenols as raw material, under the action of 2 catalyst of 0.5g embodiments, using batch still catalytic hydrogenation process,
In 150 DEG C, pressure 4MPa of temperature, 6h is reacted, alkyl phenol conversion ratio is 78.6%, and selectivity is 85.9%.
Embodiment 10
Using 25g nonyl phenols as raw material, under the action of 3 catalyst of 0.5g embodiments, using batch still catalytic hydrogenation process,
In 150 DEG C, pressure 4MPa of temperature, 6h is reacted, it is 100% to turn alkyl phenol rate, and selectivity is 99.9%.
Embodiment 11
Using 25g nonyl phenols as raw material, under the action of 4 catalyst of 0.5g embodiments, using batch still catalytic hydrogenation process,
In 150 DEG C, pressure 4MPa of temperature, 6h is reacted, alkyl phenol conversion ratio is 89.9%, and selectivity is 98.5%.
Embodiment 12
Using 25g nonyl phenols as raw material, under the action of 5 catalyst of 0.5g embodiments, using batch still catalytic hydrogenation process,
In 150 DEG C, pressure 4MPa of temperature, 6h is reacted, alkyl phenol conversion ratio is 35.5%, and selectivity is 44.5%.
Embodiment 13
Using 25g nonyl phenols as raw material, under the action of 6 catalyst of 0.5g embodiments, using batch still catalytic hydrogenation process,
In 150 DEG C, pressure 4MPa of temperature, 6h is reacted, alkyl phenol conversion ratio is 29.6%, and selectivity is 39.9%.
Embodiment 14
Using 25g nonyl phenols as raw material, under the action of 7 catalyst of 0.5g embodiments, using batch still catalytic hydrogenation process,
In 150 DEG C, pressure 4MPa of temperature, 6h is reacted, alkyl phenol conversion ratio is 27.9%, and selectivity is 38.5%.
It is compared from embodiment 8,9 and 10：Cobalt is selected as auxiliary agent, catalytic effect is best；From embodiment 10 and 11
It compares visible：The catalyst of P Modification is not passed through, alkyl phenol conversion ratio and selectivity all reduce significantly；From reality
It is visible to apply the comparison of example 10 and 12,13：The other auxiliary agents of selection are not improved the effect of catalyst；From embodiment 10 and 14 pairs
Than visible：The presence of auxiliary agent has good facilitation to the catalytic effect of catalyst.
Embodiment 15
Using 25g nonyl phenols as raw material, under the action of 3 catalyst of 0.25g embodiments, using batch still catalytic hydrogenation work
Skill in 120 DEG C, pressure 3MPa of temperature, reacts 3h, and it is 82.1% to turn alkyl phenol rate, and selectivity is 98.9%.
Embodiment 16
Using 25g nonyl phenols as raw material, under the action of 3 catalyst of 0.75g embodiments, using batch still catalytic hydrogenation work
Skill in 180 DEG C, pressure 5MPa of temperature, reacts 6h, and it is 99.9% to turn alkyl phenol rate, and selectivity is 90.2%.
From embodiment 15 and 16：Alkyl phenol adds the condition of hydrogen to be not that the higher the better, when condition is excessively high, generation
The alcoholic extract hydroxyl group of alkyl cyclohexanol is easily hydrogenated dehydration and removes, and selectivity declines；When condition is too low, reaction conversion ratio is not
It is high.
Comparative example 1
5g gama-aluminas are weighed, adding in 30g water with 0.15g triphenylphosphines is configured to solution, and impregnated carrier is modified 8h, and 110
DEG C drying, 400 DEG C roasting, obtain P Modification carrier, weigh the Co (NO of 0.4939g3)2·6H2O is dissolved in 30g distilled water, is surpassed
After sound dissolving, 5g P Modification carriers are added in solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, is aged for 24 hours,
It filters, 110 DEG C of drying, grinding, 500 DEG C of roasting 5h, then weighs the ruthenium trichloride of 0.1351g and be dissolved in 30g distilled water, ultrasound is molten
Carrier is added in solution by Xie Hou, and ammonium hydroxide is added dropwise at 30 DEG C, and it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of bakings
It is dry, grinding, 500 DEG C of roasting 5h, washing removal Cl-, then hydrogen reducing under normal pressure, 500 DEG C of temperature, 3 hours time.Ru contents are
1%, Co content are 2%.
Using 25g nonyl phenols as raw material, catalyst 0.5g is weighed, in 150 DEG C, pressure 4MPa of temperature, reacts 6h, conversion ratio
It is 73.9%, selectivity is 94.4%.
Comparative example 2
5g gama-aluminas are weighed, adding in 30g water with 0.15g pyrophosphoric acids is configured to solution, and impregnated carrier is modified 8h, 110 DEG C
Drying, 400 DEG C of roastings, obtains P Modification carrier, weighs the Co (NO of 0.4939g3)2·6H2O is dissolved in 30g distilled water, ultrasound
After dissolving, 5g P Modification carriers are added in solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, is taken out
Filter, 110 DEG C of drying, grinding, 500 DEG C of roasting 5h, then weigh the ruthenium trichloride of 0.1351g and be dissolved in 30g distilled water, ultrasonic dissolution
Afterwards, carrier is added in solution, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of bakings
It is dry, grinding, 500 DEG C of roasting 5h, washing removal Cl-, then hydrogen reducing under normal pressure, 500 DEG C of temperature, 3 hours time.Ru contents are
1%, Co content are 2%.
Using 25g nonyl phenols as raw material, catalyst 0.5g is weighed, in 150 DEG C, pressure 4MPa of temperature, reacts 6h, conversion ratio
It is 68.5%, selectivity is 94.6%.
Comparative example 3
Using 25g nonyl phenols as raw material, the Ni/TiO that Ni contents are 20% is weighed2-SiO20.5g, in 150 DEG C of temperature, pressure
4MPa, reacts 6h, conversion ratio 68.5%, and selectivity is 94.6%.
The above, preferable specific embodiment only of the invention, protection scope of the present invention is without being limited thereto, any ripe
Those skilled in the art are known in the technical scope of present disclosure, the technical solution that can obviously obtain it is simple
Variation or equivalence replacement are all fallen in protection scope of the present invention.
Claims (8)
1. a kind of preparation method of alkyl cyclohexanol, it is characterised in that：The preparation method is：Using alkyl phenol as raw material, in ruthenium
Under the action of base catalyst, using batch still catalytic hydrogenation process, the hydrogenation reaction for carrying out alkyl phenol obtains alkyl cyclohexanol,
In, ruthenium-based catalyst by mass percentage consisting of：Active component ruthenium is 1%, and auxiliary agent 2%, remaining is carrier.
2. the preparation method of alkyl cyclohexanol as described in claim 1, it is characterised in that：The auxiliary agent of the catalyst for manganese,
One kind in cobalt, nickel, the carrier are one kind in zirconium oxide, titanium oxide, gama-alumina and silica.
3. the preparation method of alkyl cyclohexanol as described in claim 1, it is characterised in that：The catalytic hydrogenation process condition
For：120~180 DEG C, 3~5MPa of pressure, 4~6h of reaction time of temperature, catalyst amount 1~3%.
4. the preparation method of alkyl cyclohexanol as described in claim 1, it is characterised in that：The specific system of the ruthenium-based catalyst
Standby process is as follows：
(1) carrier of calculation amount is weighed, is added in ammonium dihydrogen phosphate and is pre-processed to obtain P Modification presoma；
(2) the step of soluble-salt of auxiliary agent with deionized water is configured to the soluble salt solutions of auxiliary agent, adds in calculation amount (1)
Obtained P Modification presoma, stirs evenly, and ammonium hydroxide is added dropwise at 30 DEG C, and it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110
DEG C drying, Muffle kiln roasting 5 hours is ground up, sieved, obtains modified support；
(3) ruthenium trichloride for weighing calculation amount is configured to solution of ruthenium trichloride, adds in through the modified carrier of step (2), stirring is
It is even, ammonium hydroxide is added dropwise at 30 DEG C, it is 10 to adjust pH, stirs 4h, and ageing for 24 hours, filters, 110 DEG C of drying, Muffle kiln roasting 5 hours,
It is ground up, sieved, obtains catalyst precursor；
(4) catalyst precursor that step (4) obtains is put into atmospheric hydrogen in tube furnace to restore, 100~600 DEG C of temperature, when
Between 3~6 hours, be made ruthenium-based catalyst.
5. the preparation method of alkyl cyclohexanol as claimed in claim 4, it is characterised in that：Step (1) described ammonium dihydrogen phosphate
The mass concentration of solution is 1~5%.
6. the preparation method of alkyl cyclohexanol as claimed in claim 4, it is characterised in that：Step (2) and step (3) described roasting
It is 300~600 DEG C to burn temperature.
7. the preparation method of alkyl cyclohexanol as claimed in claim 4, it is characterised in that：The ruthenium-based catalyst obtained is used
In nonyl phenol, octyl phenol, dodecylphenol, bisphenol-A, isophthalodinitrile catalytic hydrogenation.
8. a kind of application of alkyl cyclohexanol prepared by method as described in claim 1, it is characterised in that：The alkyl obtained
Cyclohexanol is used to prepare alkyl cyclohexanol polyoxyethylene ether.
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| CN114192142A (en) * | 2021-11-22 | 2022-03-18 | 泰兴市凌飞化学科技有限公司 | Catalyst for hydrogenating dinonylphenol and preparation method thereof |
| CN114272924A (en) * | 2021-11-22 | 2022-04-05 | 泰兴市凌飞化学科技有限公司 | Method for recycling waste resin |
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| CN116273051A (en) * | 2023-03-21 | 2023-06-23 | 榆林学院 | Gamma-Al 2 O 3 Supported ruthenium-nickel catalyst and application thereof in phenol hydrogenation reaction |
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