CN108774106A - A kind of method and its catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol - Google Patents
A kind of method and its catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol Download PDFInfo
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- CN108774106A CN108774106A CN201810607678.4A CN201810607678A CN108774106A CN 108774106 A CN108774106 A CN 108774106A CN 201810607678 A CN201810607678 A CN 201810607678A CN 108774106 A CN108774106 A CN 108774106A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- 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
- C07C29/143—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 ketones
- C07C29/145—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 ketones with hydrogen or hydrogen-containing gases
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/847—Vanadium, niobium or tantalum or polonium
- B01J23/8474—Niobium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
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Abstract
The method that the present invention provides a kind of to produce sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, including secondary octanone and hydrogenation reaction, the hydrogenation reaction are extracted by thick sec-octyl alcohol, temperature is 88 DEG C, holding pressure is 3.5MPa, hydrogen flow rate 120ml/min, hydrogen to oil volume ratio 4000:3, successive reaction 6 hours；The present invention also provides its catalyst, by absorbent charcoal carrier and composite catalyst powder constituent, ratio 2:3, the composite catalyst powder is made of 30 parts of diatomite, 15 parts of nickel oxide, 3 parts of zinc aluminate, 2 parts of titanium oxide, 3 parts of niobium oxide, 8 parts of diboron trioxide, 11 parts of aluminium oxide, 8 parts of zirconium oxide；The catalyst of the present invention, under the conditions of same process, catalyst activity is significantly improved, and service life extends, identical raw materials for production, which are put into, can create more values of the product, high selectivity, and reaction time is short, it is at low cost, removal of impurities process is saved, overall economic efficiency is notable.
Description
Technical field
The invention belongs to chemical industry technical field of refinement, are related to a kind of method that secondary octanone hydrogenating produces sec-octyl alcohol, specifically relate to
A kind of and method and its catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol.
Background technology
Alcohol and ketone are all important at this stage chemicals, are had been widely used in industry and daily life；Ketone adds hydrogen
It is the common method of industrially prepared alcohol, ketone adds the source of the hydrogen atom in hydrogen to be usually hydrogen.
Sec-octyl alcohol is a kind of important industrial chemicals, sec-octyl alcohol（English name sec-Caprylic alcohol, sec-
Octyl alcohol）Also known as sec-n-octyl alcohol（2-Caprylic alcohol,2-Octyl alcohol）, alias hexyl methyl first
Alcohol（Hexyl methyl carbinol）, 1- isoocanols（1-Methylheptanol,1-methylheptyl
alcohol）, 2- hydroxyoctanes (2-Hydroxyl octane).Liquid that is colourless, transparent, having special taste, it is inflammable.It is except available
It does other than anti-foaming agent, may further be used to the raw material and solvent of synthesis plasticizer, surfactant, farm chemical emulgent and synthetic perfume
Deng.
Sec-octyl alcohol can be made by castor oil Direct Pyrolysis, can be also made by secondary octanone hydrogenating.Current secondary octanone hydrogenating system
In the patent document report of sec-octyl alcohol, the catalyst and process condition of ketone compounds Hydrogenation alcohol compound are as follows：China
It is Cu-Cr-Zn ternary oxides or composite oxides that patent CN90108584, which describes a kind of catalyst, prepares pressure 8MPa,
230-300 DEG C of temperature, condition is higher.Patent CN94190945 describes a kind of preparation method of cupric hydrogenation catalyst, need to contain
The molding parent of copper catalyst for hydrogenation, but selectivity is low, product separation and purification difficult.And it is current by thick sec-octyl alcohol
It extracts the method that secondary octanone hydrogenating produces sec-octyl alcohol and is primarily present following defect：（1）Method is complicated, and process conditions are difficult to control；（2）
Selectivity is low with conversion ratio, and the later stage is not easily separate；（3）For production method to equipment requirement height, the reaction time is long.Therefore there is an urgent need for
A kind of method and its catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol is studied, identical raw materials for production are thrown
Enter, more products value can be increased, improve selectivity, reduce cost, save removal of impurities process, has to improving overall economic efficiency
Important meaning.
Invention content
The present invention provides a kind of method and its catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol,
To realize following goal of the invention：
（1）The method of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, simple for process, operation side
Just；
（2）The method of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, improve selectivity, investment at
This is small, has saved production cost；
（3）The catalyst of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, catalyst activity has bright
Aobvious raising；
（4）The catalyst of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, service life is opposite to prolong
It is long.
In order to solve the above technical problems, using following technical scheme：
A method of producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, which is characterized in that described by thick sec-octyl alcohol
The method that the middle secondary octanone hydrogenating of extraction produces sec-octyl alcohol includes by extracting secondary octanone and hydrogenation reaction in thick sec-octyl alcohol.
As currently preferred technical solution, described by extracting secondary octanone in thick sec-octyl alcohol, the pressure of the first tower room is
The pressure of 15kPa, the second tower room are 12kPa, and top gaseous phase temperature is 135 DEG C, and the pressure of after-fractionating tower is 20 kPa, tower top
Gas phase temperature is 160 DEG C.
As currently preferred technical solution, described by extracting secondary octanone in thick sec-octyl alcohol, the recovery rate of secondary octanone is
99.6%, the purity of secondary octanone is 99.2%, sec-octyl alcohol accounting 97.8% in impurity.
As currently preferred technical solution, the hydrogenation reaction, temperature is 88 DEG C, and holding pressure is 3.5MPa, hydrogen
Gas velocity is 120ml/min, hydrogen to oil volume ratio 4000:3, successive reaction 6 hours.
A kind of catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, the catalyst, by activated carbon
Carrier and composite catalyst powder constituent, ratio 2:3.
As currently preferred technical solution, the composite catalyst powder, by 30 parts of diatomite, 15 parts of nickel oxide,
8 parts of 3 parts of zinc aluminate, 2 parts of titanium oxide, 3 parts of niobium oxide, 8 parts of diboron trioxide, 11 parts of aluminium oxide, zirconium oxide compositions.
As currently preferred technical solution, the catalyst, preparation method includes：Absorbent charcoal carrier and composite catalyzing
Agent powder carry out under nitrogen flowing microwave-it is infrared-ULTRASONIC COMPLEX processing, wherein microwave frequency 85MHz, infrared wavelength 200
μm, ultrasonic frequency 455KHz, processing time 15-18min, nitrogen flow 30ml/min.
As currently preferred technical solution, the composite catalyst powder, preparation method includes：It is molten to weigh diatomite
In deionized water, zinc aluminate, niobium oxide, diboron trioxide, aluminium oxide is added and stirs into paste, stands 12h, dry, grinding,
455 DEG C are warming up to 10 DEG C/min rates, calcines 0.5h.
The present invention is had the following advantages compared with prior art using above technical scheme：
（1）The method of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, simple for process, operation side
Just；
（2）The method of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, improve selectivity, investment at
This is small, has saved production cost；
（3）The catalyst of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, catalyst activity has bright
Aobvious raising；
（4）The catalyst of the present invention for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, service life is opposite to prolong
It is long.
Specific implementation mode
A kind of catalyst that producing sec-octyl alcohol by secondary octanone hydrogenating of embodiment 1
A kind of catalyst for producing sec-octyl alcohol by secondary octanone hydrogenating of the present invention, by absorbent charcoal carrier and composite catalyst powder group
At, the composite catalyst powder, by 30 parts of diatomite, 15 parts of nickel oxide, 3 parts of zinc aluminate, 2 parts of titanium oxide, 3 parts of niobium oxide,
8 parts of 8 parts of diboron trioxide, 11 parts of aluminium oxide, zirconium oxide compositions.
The preparation method of the absorbent charcoal carrier, includes the following steps：
The selection of a support materials
Select high-quality coconut husk for raw material, the coconut husk removes outer layer green pericarp for current year fresh coconut husk, major diameter 5.5cm,
Minor axis is 4.2cm, moisture content 7.5%.
B caustic dips
Above-mentioned coconut husk is subjected to denitration desulfurization modification, is put into fixed bed reactors, is purged 1 hour with nitrogen and removes surface
Volatilizable impurity, be then added in 10% potassium hydroxide solution and impregnate 15h, it is then dry in converter, open vacuum system,
Vacuum degree is 0.09MPa, 112 DEG C of drying temperature；
It is 380 DEG C that nitrogen, which purges temperature, and the desulfurization degree of denitration desulfurization modification is 99.0%.
C is carbonized
Coconut husk by alkalization is carbonized, carbonization temperature initial temperature is in the case where nitrogen flow is the protection of 25ml/min
325 DEG C, with the heating rate of 5 DEG C/min, 405 DEG C are risen to, carbonizes 2.5 hours, obtains carbonized material.
The carbonized material, ash content 3.5%, moisture content are less than 2.5%.
D is activated
The mass ratio of anhydrous potassium hydroxide treatment by carbonized material to melt, carbonized material and anhydrous potassium hydroxide is 4:5, temperature is
It 400 DEG C, handles 5 hours.
E pickling
It is rinsed with diluted acid, until pH value is between 6.5-7, it is dry, filter residue is filtered out, absorbent charcoal carrier is obtained.
The absorbent charcoal carrier, iodine sorption value 1125mg/g, 3000 ㎡ of specific surface area/g, bulk density 465g/L, pH value
For 6.5-7, ash content 3%, moisture content≤3%, mechanical strength 99.6%, not easy disintegrating.
A kind of preparation method of catalyst for producing sec-octyl alcohol by secondary octanone hydrogenating of 2 present invention of embodiment, including it is following
Step：
（1）Diatomite, nickel oxide, zinc aluminate, titanium oxide, niobium oxide, diboron trioxide, aluminium oxide, oxygen are weighed by formula rate
Change zirconium, match appropriate amount of deionized water respectively, is ground 5.5 hours through colloid mill, ground 200 mesh sieve.
（2）It weighs diatomite to be dissolved in deionized water, zinc aluminate, niobium oxide, diboron trioxide, aluminium oxide is added and stirs into
Paste after standing 12h at room temperature, is transferred in baking oven dry, grinding；
Then it places it in tube furnace, under nitrogen flowing, is warming up to 455 DEG C with 10 DEG C/min rates, is down to after calcining 0.5h
Room temperature obtains powder.
（3）It by suitable water is added in nickel oxide, titanium oxide, is stirred continuously and slurry is made, zirconium oxide is then added, stir
Uniformly, 105 DEG C are heated to, heat preservation grinding 3 hours obtains mixed slurry, after standing 20h.
（4）By step（2）Powder be added to step（3）In mixed slurry in, be added a small amount of 2% ethanol solution, stir
Mix to paste, at room temperature, stand 20 hours in nitrogen stream after, be transferred in baking oven dry, calcining, grinding is urged to get compound
Agent powder.
（5）Composite catalyst powder is mixed with above-mentioned absorbent charcoal carrier, mixed proportion 2:3, by the above mixture
Under nitrogen flowing carry out microwave-it is infrared-ULTRASONIC COMPLEX processing, wherein microwave frequency is set as 85MHz, and infrared wavelength is set as
200 μm, ultrasonic frequency is set as 455KHz, processing time 15-18min, and nitrogen flow 30ml/min is obtained of the invention
Catalyst.
A kind of method for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol of 3 present invention of embodiment
Include the following steps：
A extracts secondary octanone by thick sec-octyl alcohol：
The method that separating-purifying is distilled according to partition board extracts secondary octanone from thick sec-octyl alcohol, wherein first the first tower of destilling tower room
Pressure is 15kPa, and the pressure of the second tower room is 12kPa, and top gaseous phase temperature is 135 DEG C, and the pressure of after-fractionating tower is 20
KPa, top gaseous phase temperature are 160 DEG C.
After testing, the recovery rate of secondary octanone is 99.6% in this step, and the purity of secondary octanone is 99.2%, sec-octyl alcohol in impurity
Accounting 97.8%.
B hydrogenation reactions：
Hydrogenation reactor is waist type container, major diameter：Minor axis=0.45, internal actual volume is 50m3, by above-mentioned catalyst（It is compound
Catalyst fines quality is 1.2g）It uniformly places in the reactor in advance, while being passed through nitrogen and excluding air, keep in reactor
Pressure is 3.2-3.5MPa, and temperature is 150 DEG C, after being slowly introducing hydrogen 2 hours（Hydrogen flow rate is 70 ml/min）；Using secondary
The method of octanone liquid-phase hydrogenatin, during continuous fixed bed reaction or continuous, controlled at 88 DEG C, holding pressure is 3.5MPa, hydrogen
Gas velocity is 120ml/min, hydrogen to oil volume ratio 4000:3, successive reaction 6 hours；After testing, the conversion of the secondary octanone of the present invention
Rate is 99.7%, sec-octyl alcohol selectivity 99.8%.
Catalyst carrier and commercially available absorbent charcoal carrier not processed by the invention prepared by the above method（It is right
Ratio 1）, using the composite catalyst powder being equally equipped with it is identical under nitrogen flowing carry out microwave-it is infrared-ULTRASONIC COMPLEX at
Reason, investigates its catalytic activity and service life, is as a result described in table 1 below under the same conditions respectively：
Table 1：The active lifetime comparison sheet of different catalysts
It can be seen that from the data of upper table：
By such method treated absorbent charcoal carrier, manufactured catalyst for producing sec-octyl alcohol by secondary octanone hydrogenating, in phase
Under the conditions of same Hydrogenation taking technique, catalyst activity is significantly improved, and service life is opposite to extend, and identical production is former
Material input can create more values of the product, and selectivity is higher, and reaction time is short, at low cost, save removal of impurities process, synthesis
Economic benefit has some idea of.
Unless otherwise indicated, percentage of the present invention is weight percent, and ratio of the present invention is
Mass ratio.
Finally it should be noted that：The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention,
It, for those skilled in the art, still can be with although describing the invention in detail with reference to the foregoing embodiments
Technical scheme described in the above embodiments is modified or equivalent replacement of some of the technical features.It is all
Within the spirit and principles in the present invention, any modification, equivalent replacement, improvement and so on should be included in the guarantor of the present invention
Within the scope of shield.
Claims (8)
1. a kind of method for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, which is characterized in that
The method for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, including by thick sec-octyl alcohol extract secondary octanone and
Hydrogenation reaction.
2. a kind of method for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol according to claim 1, special
Sign is,
The hydrogenation reaction, temperature are 88 DEG C, and holdings pressure is 3.5MPa, hydrogen flow rate 120ml/min, and hydrogen to oil volume ratio is
4000:3, successive reaction 6 hours.
3. a kind of method for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol according to claim 1 or 2,
It is characterized in that,
It is described by extracting secondary octanone in thick sec-octyl alcohol, the pressure of the first tower room is 15kPa, and the pressure of the second tower room is 12kPa, tower
It is 135 DEG C to push up gas phase temperature, and the pressure of after-fractionating tower is 20 kPa, and top gaseous phase temperature is 160 DEG C.
4. a kind of method for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol according to claim 1, special
Sign is,
Described by extracting secondary octanone in thick sec-octyl alcohol, the recovery rate of secondary octanone is 99.6%, and the purity of secondary octanone is 99.2%.
5. a kind of catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol, which is characterized in that
The catalyst, by absorbent charcoal carrier and composite catalyst powder constituent, ratio 2:3.
6. a kind of catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol according to claim 5,
It is characterized in that,
The composite catalyst powder, by 30 parts of diatomite, 15 parts of nickel oxide, 3 parts of zinc aluminate, 2 parts of titanium oxide, 3 parts of niobium oxide,
8 parts of 8 parts of diboron trioxide, 11 parts of aluminium oxide, zirconium oxide compositions.
7. a kind of catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol according to claim 5,
It is characterized in that,
The catalyst, preparation method include：It is red that absorbent charcoal carrier and composite catalyst powder carry out microwave-under nitrogen flowing
Outside-ULTRASONIC COMPLEX processing, microwave frequency 85MHz, infrared wavelength is 200 μm, ultrasonic frequency 455KHz, and processing time is
15-18min, nitrogen flow 30ml/min.
8. a kind of catalyst for producing sec-octyl alcohol by extracting secondary octanone hydrogenating in thick sec-octyl alcohol according to claim 5,
It is characterized in that,
The composite catalyst powder, preparation method include：It weighs diatomite to be dissolved in deionized water, zinc aluminate, oxygen is added
Change niobium, diboron trioxide, aluminium oxide and stir into paste, stands 12h, dry, grinding is warming up to 455 DEG C with 10 DEG C/min rates,
Calcine 0.5h.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810607678.4A CN108774106B (en) | 2018-06-13 | 2018-06-13 | Method for extracting sec-octanone from crude sec-octanol and hydrogenating to prepare sec-octanol and catalyst thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810607678.4A CN108774106B (en) | 2018-06-13 | 2018-06-13 | Method for extracting sec-octanone from crude sec-octanol and hydrogenating to prepare sec-octanol and catalyst thereof |
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| CN108774106B CN108774106B (en) | 2021-06-18 |
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ID=64025082
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Citations (5)
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| CN1279127A (en) * | 2000-05-12 | 2001-01-10 | 石油大学(华东) | Process for preparing paraoctanol by hydrogenction of paraoctanone and its catalyst |
| CN1346703A (en) * | 2001-09-11 | 2002-05-01 | 中国石油天然气股份有限公司 | Method for preparing sec-octanol by sec-octanone hydrogenation and nickel-containing catalyst thereof |
| CN1347758A (en) * | 2001-09-11 | 2002-05-08 | 中国石油天然气股份有限公司 | Method for preparing sec-octanol by sec-octanone hydrogenation and copper-containing catalyst thereof |
| CN102408305A (en) * | 2010-09-21 | 2012-04-11 | 中国石油化工股份有限公司 | Catalytic conversion method of ketone and alcohol |
| CN102503789A (en) * | 2011-10-12 | 2012-06-20 | 潍坊市元利化工有限公司 | Method for distilling, separating and purifying ketone alcohol mixture by utilizing separating plate |
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| DE3932332A1 (en) * | 1989-09-28 | 1991-04-11 | Hoechst Ag | METHOD FOR PRODUCING ALCOHOLS (ONE STAGE) |
| CN1974514A (en) * | 2006-12-19 | 2007-06-06 | 天津大学 | 2-octyl ketone hydrogenating reduction process for preparing 2-octyl alcohol |
| CN106187700B (en) * | 2015-04-29 | 2018-12-28 | 中国石油化工股份有限公司 | The separation method of butanol and octanol waste liquid back end hydrogenation |
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2018
- 2018-06-13 CN CN201810607678.4A patent/CN108774106B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1279127A (en) * | 2000-05-12 | 2001-01-10 | 石油大学(华东) | Process for preparing paraoctanol by hydrogenction of paraoctanone and its catalyst |
| CN1346703A (en) * | 2001-09-11 | 2002-05-01 | 中国石油天然气股份有限公司 | Method for preparing sec-octanol by sec-octanone hydrogenation and nickel-containing catalyst thereof |
| CN1347758A (en) * | 2001-09-11 | 2002-05-08 | 中国石油天然气股份有限公司 | Method for preparing sec-octanol by sec-octanone hydrogenation and copper-containing catalyst thereof |
| CN102408305A (en) * | 2010-09-21 | 2012-04-11 | 中国石油化工股份有限公司 | Catalytic conversion method of ketone and alcohol |
| CN102503789A (en) * | 2011-10-12 | 2012-06-20 | 潍坊市元利化工有限公司 | Method for distilling, separating and purifying ketone alcohol mixture by utilizing separating plate |
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