CN108774106B - Method for extracting sec-octanone from crude sec-octanol and hydrogenating to prepare sec-octanol and catalyst thereof - Google Patents
Method for extracting sec-octanone from crude sec-octanol and hydrogenating to prepare sec-octanol and catalyst thereof Download PDFInfo
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- CN108774106B CN108774106B CN201810607678.4A CN201810607678A CN108774106B CN 108774106 B CN108774106 B CN 108774106B CN 201810607678 A CN201810607678 A CN 201810607678A CN 108774106 B CN108774106 B CN 108774106B
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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
Abstract
The invention provides a method for preparing sec-octanol by extracting sec-octanone from crude sec-octanol and hydrogenating, which comprises the steps of extracting sec-octanone from crude sec-octanol and performing hydrogenation reaction, wherein the hydrogenation reaction is performed at the temperature of 88 ℃, the holding pressure of 3.5MPa, the hydrogen flow rate of 120ml/min and the hydrogen-oil volume ratio of 4000:3 for 6 hours; the invention also provides a catalyst, which consists of an activated carbon carrier and composite catalyst powder in a ratio of 2:3, wherein the composite catalyst powder consists 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 alumina and 8 parts of zirconia; the catalyst of the invention has the advantages of obviously improved activity, prolonged service life, high selectivity, short reaction period, low cost, saving impurity removal process and obvious comprehensive economic benefit, and the same production raw material investment can create more product values under the same process conditions.
Description
Technical Field
The invention belongs to the technical field of chemical refining, and relates to a method for preparing sec-octanol by sec-octanone hydrogenation, in particular to a method for preparing sec-octanol by extracting sec-octanone from crude sec-octanol and hydrogenating the sec-octanone and a catalyst thereof.
Background
Alcohol and ketone are important chemicals at present, and have wide application in industry and daily life; the hydrogenation of ketones is a common method for the industrial production of alcohols, the source of the hydrogen atoms in the hydrogenation of ketones generally being hydrogen.
Secondary octanol is an important chemical raw material, and is called 2-octanol (2-Octyl alcohol), also called Hexyl methyl methanol (Hexyl methyl methanol), 1-Methylheptanol (1-Methylheptanol, 1-methylheptyl alcohol), 2-hydroxy octane (2-hydroxy octane). Colorless, transparent, special-taste liquid and inflammable. It can be used as defoaming agent, plasticizer, surfactant, emulsifier for agricultural chemicals and raw material and solvent for synthesizing perfume.
The sec-octanol can be obtained by direct cracking of castor oil or by hydrogenation of sec-octanone. In the patent literature reports of the preparation of sec-octanol by hydrogenation of sec-octanone at present, the catalyst and process conditions of the preparation of alcohol compounds by hydrogenation of ketone compounds are as follows: chinese patent CN90108584 describes a catalyst which is Cu-Cr-Zn ternary oxide or composite oxide, and the preparation pressure is 8MPa, the temperature is 230-. Patent CN94190945 describes a preparation method of a copper-containing hydrogenation catalyst, which needs a formed precursor of the copper-containing hydrogenation catalyst, but has low selectivity and difficult product separation and purification. The existing method for extracting the sec-octanone from the crude sec-octanol and preparing the sec-octanol by hydrogenation mainly has the following defects: (1) the method is complex and the process conditions are difficult to control; (2) the selectivity and the conversion rate are low, and the separation is not easy in the later period; (3) the production method has high requirements on equipment and long reaction time. Therefore, the method for extracting the sec-octanone from the crude sec-octanol and hydrogenating the sec-octanone to prepare the sec-octanol and the catalyst thereof need to be researched, the same production raw material investment can be realized, more product values can be increased, the selectivity is improved, the cost is reduced, the impurity removal process is saved, and the method has important significance for improving the comprehensive economic benefit.
Disclosure of Invention
The invention provides a method for preparing sec-octanol by extracting sec-octanone from crude sec-octanol and hydrogenating the sec-octanone and a catalyst thereof, which aim at realizing the following purposes:
(1) the method for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating has simple process and convenient operation;
(2) the method for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating the sec-octanone improves the selectivity, has low investment cost and saves the production cost;
(3) the catalyst for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating has obviously improved activity;
(4) the catalyst for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating has relatively prolonged service life.
In order to solve the technical problems, the following technical scheme is adopted:
the method for preparing the secondary octanol by extracting the secondary octanone from the crude secondary octanol and hydrogenating is characterized by comprising the steps of extracting the secondary octanone from the crude secondary octanol and performing hydrogenation reaction.
In a preferred embodiment of the present invention, the extraction of sec-octanone from crude sec-octanol is carried out at a first column chamber pressure of 15kPa, a second column chamber pressure of 12kPa, an overhead gas phase temperature of 135 ℃, a second distillation column pressure of 20kPa, and an overhead gas phase temperature of 160 ℃.
As a preferable technical scheme of the invention, the extraction rate of the sec-octanone from the crude sec-octanol is 99.6%, the purity of the sec-octanone is 99.2%, and the content of the sec-octanol in the impurities is 97.8%.
As a preferable technical scheme of the invention, the hydrogenation reaction is carried out at the temperature of 88 ℃, the pressure is kept at 3.5MPa, the hydrogen flow rate is 120ml/min, the volume ratio of hydrogen to oil is 4000:3, and the continuous reaction is carried out for 6 hours.
A catalyst for extracting sec-octanone from crude sec-octanol and hydrogenating to prepare sec-octanol is composed of active carbon carrier and composite catalyst powder in the ratio of 2: 3.
In a preferred embodiment of the present invention, the composite catalyst powder comprises 30 parts of diatomaceous earth, 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 alumina, and 8 parts of zirconia.
As a preferable technical scheme of the invention, the preparation method of the catalyst comprises the following steps: and performing microwave-infrared-ultrasonic composite treatment on the activated carbon carrier and the composite catalyst powder under a nitrogen flow, wherein the microwave frequency is 85MHz, the infrared wavelength is 200 microns, the ultrasonic frequency is 455KHz, the treatment time is 15-18min, and the nitrogen flow is 30 ml/min.
As a preferable technical scheme of the invention, the preparation method of the composite catalyst powder comprises the following steps: weighing diatomite, dissolving the diatomite in deionized water, adding zinc aluminate, niobium oxide, diboron trioxide and alumina, stirring into paste, standing for 12h, drying, grinding, heating to 455 ℃ at the speed of 10 ℃/min, and calcining for 0.5 h.
By adopting the technical scheme, compared with the prior art, the invention has the following advantages:
(1) the method for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating has simple process and convenient operation;
(2) the method for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating the sec-octanone improves the selectivity, has low investment cost and saves the production cost;
(3) the catalyst for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating has obviously improved activity;
(4) the catalyst for preparing the sec-octanol by extracting the sec-octanone from the crude sec-octanol and hydrogenating has relatively prolonged service life.
Detailed Description
Example 1A catalyst for the hydrogenation of Paraoctanol to Paraoctanone
The catalyst for preparing the octanol by hydrogenating the sec-octanone consists of an active carbon carrier and composite catalyst powder, wherein the composite catalyst powder consists of 30 parts of kieselguhr, 15 parts of nickel oxide, 3 parts of zinc aluminate, 2 parts of titanium oxide, 3 parts of niobium oxide, 8 parts of boron trioxide, 11 parts of alumina and 8 parts of zirconium oxide.
The preparation method of the activated carbon carrier comprises the following steps:
a selection of Carrier materials
Selecting high-quality coconut shells as raw materials, wherein the coconut shells are fresh coconut shells in the same year, removing outer green peel, and having a long diameter of 5.5cm, a short diameter of 4.2cm and a water content of 7.5%.
b alkali leaching
Carrying out denitration and desulfurization modification treatment on the coconut shells, putting the coconut shells into a fixed bed reactor, blowing the coconut shells for 1 hour by using nitrogen to remove volatile impurities on the surfaces of the coconut shells, then adding the coconut shells into 10% potassium hydroxide solution to be soaked for 15 hours, then drying the coconut shells in a converter, starting a vacuum system, wherein the vacuum degree is 0.09MPa, and the drying temperature is 112 ℃;
the nitrogen purging temperature is 380 ℃, and the desulfurization rate of the denitration desulfurization modification treatment is 99.0%.
c charring
Carbonizing the alkalized coconut shell under the protection of 25ml/min of nitrogen flow, wherein the initial temperature of the carbonization temperature is 325 ℃, the temperature is increased to 405 ℃ at the heating rate of 5 ℃/min, and the carbonization time is 2.5 hours, thus obtaining the carbonized material.
The ash content of the carbonized material is 3.5 percent, and the water content is lower than 2.5 percent.
d activation
Treating the carbonized material with molten anhydrous potassium hydroxide at 400 deg.c in the mass ratio of 4 to 5 for 5 hr.
e acid washing
Washing with diluted acid until pH is 6.5-7, drying, and filtering to remove residue to obtain activated carbon carrier.
The activated carbon carrier has an iodine adsorption value of 1125mg/g, a specific surface area of 3000 square meters per gram, a bulk specific gravity of 465g/L, a pH value of 6.5-7, ash content of 3%, water content of less than or equal to 3%, and mechanical strength of 99.6%, and is not easy to disintegrate.
Example 2 a process for the preparation of a catalyst for the hydrogenation of sec-octanone to produce sec-octanol in accordance with the present invention comprises the following steps:
(1) weighing diatomite, nickel oxide, zinc aluminate, titanium oxide, niobium oxide, boron trioxide, alumina and zirconia according to the formula proportion, respectively adding a proper amount of deionized water, grinding for 5.5 hours by a colloid mill, and grinding and sieving by a 200-mesh sieve.
(2) Weighing diatomite, dissolving the diatomite in deionized water, adding zinc aluminate, niobium oxide, diboron trioxide and alumina, stirring into paste, standing at room temperature for 12 hours, transferring to an oven, drying and grinding;
then placing the mixture into a tube furnace, heating the mixture to 455 ℃ at the speed of 10 ℃/min under the nitrogen flow, calcining the mixture for 0.5h, and then cooling the calcined mixture to room temperature to obtain powder.
(3) Adding a proper amount of water into nickel oxide and titanium oxide, continuously stirring to prepare slurry, then adding zirconium oxide, uniformly stirring, heating to 105 ℃, preserving heat, grinding for 3 hours to obtain mixed slurry, and standing for 20 hours.
(4) And (3) adding the powder in the step (2) into the mixed slurry in the step (3), adding a small amount of 2% ethanol solution, stirring to be pasty, standing for 20 hours in nitrogen flow at room temperature, transferring to an oven for drying, calcining and grinding to obtain the composite catalyst powder.
(5) And (2) mixing the composite catalyst powder with the activated carbon carrier in a mixing ratio of 2:3, and performing microwave-infrared-ultrasonic composite treatment on the mixture under a nitrogen flow, wherein the microwave frequency is 85MHz, the infrared wavelength is 200 microns, the ultrasonic frequency is 455KHz, the treatment time is 15-18min, and the nitrogen flow is 30ml/min to obtain the catalyst.
Example 3A process for the hydrogenation of sec-octanones from crude sec-octanol according to the invention
The method comprises the following steps:
a extraction of sec-octanone from crude sec-octanol:
extracting sec-octanone from crude sec-octanol by separation and purification with partition distillation, wherein the pressure of the first chamber of the first distillation column is 15kPa, the pressure of the second chamber is 12kPa, the temperature of the gas phase at the top of the column is 135 deg.C, the pressure of the second distillation column is 20kPa, and the temperature of the gas phase at the top of the column is 160 deg.C.
Through detection, the extraction rate of the sec-octanone in the step is 99.6%, the purity of the sec-octanone is 99.2%, and the content of the sec-octanol in impurities is 97.8%.
B, hydrogenation reaction:
the hydrogenation reactor is a waist-shaped container, and the length diameter is as follows: carrying out thin-path =0.45 and internal actual volume 50m, uniformly placing the catalyst (the mass of the composite catalyst powder is 1.2 g) in a reactor in advance, introducing nitrogen to remove air, keeping the pressure in the reactor at 3.2-3.5MPa and the temperature at 150 ℃, and slowly introducing hydrogen for 2 hours (the hydrogen flow rate is 70 ml/min); adopting a method of sec-octanone liquid phase hydrogenation, controlling the temperature at 88 ℃, keeping the pressure at 3.5MPa, controlling the hydrogen flow rate at 120ml/min and the hydrogen-oil volume ratio at 4000:3 in the process of fixed bed continuous reaction, and continuously reacting for 6 hours; the detection proves that the conversion rate of the sec-octanone is 99.7 percent, and the selectivity of the sec-octanol is 99.8 percent.
The catalyst carrier prepared by the above method, and the commercially available activated carbon carrier without the treatment of the present invention (comparative example 1) were subjected to microwave-infrared-ultrasonic composite treatment under the same nitrogen flow using the same prepared composite catalyst powder, and the catalytic activity and the lifetime thereof were examined under the same conditions, respectively, and the results are shown in the following table 1:
table 1: active life comparison table of different catalysts
As can be seen from the data in the table above:
the catalyst for preparing the sec-octanol by hydrogenating the sec-octanone, which is prepared from the activated carbon carrier treated by the method, has the advantages of obviously improved catalyst activity and relatively prolonged service life under the same hydrogenation preparation process condition, can create more product values by using the same production raw material, and has the advantages of higher selectivity, short reaction period, low cost, impurity removal process saving and obvious comprehensive economic benefit.
All percentages used herein are weight percentages and all ratios described herein are mass ratios, unless otherwise indicated.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (2)
1. A process for the extraction of sec-octanone from crude sec-octanol and hydrogenation to produce sec-octanol, wherein said process comprises the steps of extracting sec-octanone from crude sec-octanol and hydrogenation;
the catalyst used in the method consists of an activated carbon carrier and composite catalyst powder in a ratio of 2: 3;
the composite catalyst powder consists 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 boron trioxide, 11 parts of alumina and 8 parts of zirconia;
the preparation method of the composite catalyst powder comprises the following steps: weighing diatomite, dissolving the diatomite in deionized water, adding zinc aluminate, niobium oxide, diboron trioxide and alumina, stirring into paste, standing for 12h, drying, grinding, heating to 455 ℃ at the speed of 10 ℃/min, and calcining for 0.5 h;
the preparation method of the catalyst comprises the following steps: carrying out microwave-infrared-ultrasonic composite treatment on the activated carbon carrier and the composite catalyst powder under nitrogen flow, wherein the microwave frequency is 85MHz, the infrared wavelength is 200 microns, the ultrasonic frequency is 455KHz, the treatment time is 15-18min, and the nitrogen flow is 30 ml/min;
the hydrogenation reaction is carried out for 6 hours continuously at the temperature of 88 ℃, the pressure of 3.5MPa, the hydrogen flow rate of 120ml/min and the hydrogen-oil volume ratio of 4000: 3.
2. A process for the extraction of sec-octanones from crude sec-octanol and hydrogenation thereof according to claim 1, wherein,
extracting sec-octanone from crude sec-octanol by separation and purification with partition distillation, wherein the pressure of the first chamber of the first distillation column is 15kPa, the pressure of the second chamber is 12kPa, the temperature of the gas phase at the top of the column is 135 deg.C, the pressure of the second distillation column is 20kPa, and the temperature of the gas phase at the top of the column is 160 deg.C.
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| US5684215A (en) * | 1989-09-28 | 1997-11-04 | Hoechst Aktiengesellschaft | One stage process for the preparation of alcohols |
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| CN1346703A (en) * | 2001-09-11 | 2002-05-01 | 中国石油天然气股份有限公司 | Process for preparing sec.-octanoly by hydrogenating sec.-octanone and its catalyst containing Ni |
| CN1974514A (en) * | 2006-12-19 | 2007-06-06 | 天津大学 | 2-octyl ketone hydrogenating reduction process for preparing 2-octyl alcohol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1347758A (en) * | 2001-09-11 | 2002-05-08 | 中国石油天然气股份有限公司 | Sec-octanone hydrogenating process of preparing sec-octanol and its copper-containing catalyst |
| CN102408305B (en) * | 2010-09-21 | 2014-04-02 | 中国石油化工股份有限公司 | Catalytic conversion method of ketone and alcohol |
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- 2018-06-13 CN CN201810607678.4A patent/CN108774106B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5684215A (en) * | 1989-09-28 | 1997-11-04 | Hoechst Aktiengesellschaft | One stage process for the preparation of alcohols |
| 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 | Process for preparing sec.-octanoly by hydrogenating sec.-octanone and its catalyst containing Ni |
| CN1974514A (en) * | 2006-12-19 | 2007-06-06 | 天津大学 | 2-octyl ketone hydrogenating reduction process for preparing 2-octyl 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 |
| CN106187700A (en) * | 2015-04-29 | 2016-12-07 | 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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