CN114210327A - Preparation method of catalyst for preparing isobutyl isobutyrate by adopting Tishchenko condensation reaction of isobutyraldehyde - Google Patents

Preparation method of catalyst for preparing isobutyl isobutyrate by adopting Tishchenko condensation reaction of isobutyraldehyde Download PDF

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CN114210327A
CN114210327A CN202111627363.4A CN202111627363A CN114210327A CN 114210327 A CN114210327 A CN 114210327A CN 202111627363 A CN202111627363 A CN 202111627363A CN 114210327 A CN114210327 A CN 114210327A
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catalyst
reaction
isobutyraldehyde
kettle
isobutyl isobutyrate
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杨萍
卢小松
张世元
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Runtai Chemical Taixing Co ltd
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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
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/462—Ruthenium
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/24—Nitrogen compounds
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
    • B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
    • B01J29/74—Noble metals
    • B01J29/7415—Zeolite Beta
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
    • 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
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/10—After treatment, characterised by the effect to be obtained
    • B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • 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
    • Y02P20/584—Recycling of catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The invention belongs to the technical field of catalysts, and particularly relates to a preparation method of a catalyst for preparing isobutyl isobutyrate by adopting a Tishchenko condensation reaction of isobutyraldehyde. The catalyst for synthesizing isobutyl isobutyrate, which has high adsorption strength and good stability and can be recycled, is prepared by adopting monoatomic metal M (Ru and Mg) as a catalytic active center and adopting one or more carriers of nitrogen-doped carbon spheres, mesoporous silica and molecular sieves. The in-situ growth method is used, so that the distribution of the metal atom active component on the carrier is more uniform, and the existence form of the single atom on the carrier enables the catalyst to be recycled for multiple times. The catalyst is used for the reaction of preparing isobutyl isobutyrate from isobutyraldehyde in one step, and higher yield and conversion rate are obtained through experiments.

Description

Preparation method of catalyst for preparing isobutyl isobutyrate by adopting Tishchenko condensation reaction of isobutyraldehyde
Technical Field
The invention belongs to the technical field of catalysts, and particularly relates to a preparation method of a catalyst for preparing isobutyl isobutyrate by adopting a Tishchenko condensation reaction of isobutyraldehyde.
Background
Isobutyl isobutyrate (IBIBIBE) is a colorless or light yellow liquid, is mainly used for preparing spices and essence, is a main component of pineapple essence due to pineapple fragrance, and is an excellent organic solvent, paint remover and extraction additive. The isobutyl isobutyrate is basically non-toxic and harmless to human and livestock and cannot cause pollution to the environment, so that the isobutyl isobutyrate is an rare green environment-friendly product, and the isobutyl isobutyrate is applied more and more along with the increasing requirements of people on the environment.
Isobutyl isobutyrate is prepared by one step of Tishchenko condensation reaction of isobutyraldehyde, the raw material is single, and the reaction is an atom economic reaction. Although the metal alkoxide catalyst has excellent catalytic effect as a catalyst for Tishchenko condensation reaction, the catalyst has poor thermal stability, is easily deactivated during reaction at high temperature, and contains-OC in the metal alkoxide after the reaction of aldehyde Tishchenko is finished4H9Since the ligand is easily substituted with an-OH group of another substance to deactivate the catalyst, the metal alkoxide catalyst after the reaction is hardly recycled, and if the metal alkoxide in the reaction solution is not destroyed in time, it absorbs moisture in the air to form a gel-like solid, and the gel-like reaction solution cannot be further processed.
Disclosure of Invention
Aiming at the defects that a metal alkoxide catalyst is easy to inactivate and difficult to recycle, the invention prepares the monatomic catalyst by adopting metal monatomic (M (Ru, Mg)) as an active center according to the Tishchenko condensation reaction principle, the monatomic catalyst not only has similar catalytic activity compared with the metal alkoxide catalyst, but also greatly improves the stability of the catalyst, and the nitrogen-doped carbon spheres, mesoporous silica and molecular sieve are used as carriers, so that the recoverability of the catalyst is improved, and the catalyst has good synergistic effect with the metal atoms, further accelerates the generation and migration of hydride ions in the condensation reaction, and improves the catalytic activity. In addition, the invention utilizes an in-situ generation method to evenly anchor metal atoms on the carrier, so that the distribution of active centers is even.
The invention adopts an in-situ generation method to prepare the metal active sites, so that the metal active sites are uniformly loaded on the carrier, the catalyst obtains stronger stability and longer service life, and the catalyst can be recycled for multiple times. The method is used for the reaction of preparing isobutyl isobutyrate from isobutyraldehyde in one step, and can obviously improve the reactivity of the catalyst and the selectivity of isobutyl isobutyrate.
The specific preparation method of the catalyst comprises the following steps:
(1) weighing vector and MClnAdding into deionized water, and mixing with Na2CO3Mixing and placing in a water bath kettle, adjusting the pH value to 7-8 by using ammonia water, and stirring for reaction, wherein M is Ru or Mg;
wherein the dosage of the metal chloride is 5-6% of the mass of the carrier, and Na2CO3The mass ratio of the metal chloride to the metal chloride is 6: 1;
the carrier is one or more of nitrogen-doped carbon spheres, mesoporous silicon dioxide and Na-beta molecular sieve.
The water bath reaction temperature is 50-60 ℃, and the reaction time is 8-12 h.
(2) Centrifuging the liquid obtained in the step (1), washing for 3-4 times by using absolute ethyl alcohol, and then drying for 4 hours in a 120 ℃ oven;
(3) putting the solid dried in the step (2) in N2Calcining at 600-700 ℃ for 3h at the flow rate of 25ml/min, and grinding to 20-30 meshes to obtain the metal monatomic catalyst for preparing isobutyl isobutyrate by the isobutyraldehyde one-step method.
The catalyst prepared by the method is used for preparing isobutyl isobutyrate by adopting a Tishchenko condensation reaction of isobutyraldehyde, and the specific application method comprises the following steps: adding raw materials of isobutyraldehyde, solvent of isobutanol and catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained, and the reaction is carried out.
Has the advantages that: the invention takes metal single atom as an active center and takes porous materials such as nitrogen-doped carbon, mesoporous silica, molecular sieve and the like as carriers to prepare the isobutyl isobutyrate synthesis catalyst which has high adsorption strength and good stability and can be recycled. The in-situ growth method is used, so that the distribution of the metal atom active component on the carrier is more uniform, and the existence form of the single atom on the carrier enables the catalyst to be recycled for multiple times. The catalyst is used for the reaction of preparing isobutyl isobutyrate from isobutyraldehyde in one step, and higher yield and conversion rate are obtained through experiments.
Detailed Description
The present invention is further described below with reference to examples, but is not limited thereto.
Example 1
(1) Mixing 200mL of absolute ethanol and 200mL of deionized water, adding 4g P123 surfactant, stirring at room temperature for 30min, adding 2g of dopamine hydrochloride, slowly adding 5mL of 1, 3, 5-mesitylene after stirring and dissolving, stirring for 1h to fully oxidize the dopamine hydrochloride, adding 20mL of ammonia water by using a microsyringe to maintain the pH value at 8-9, stirring for 12h, alternately washing for 3 times by using deionized water ethanol after centrifugation, drying in vacuum overnight, and then performing N/N (N) drying at 40mL/min2Calcining for 2h at 400 ℃ in airflow to prepare nitrogen-doped carbon spheres (NMC) for later use.
(2) Weighing 10g of carrier carbon-doped carbon spheres and 0.5g of RuCl3Adding into 30mL deionized water, adding 3g Na into the solution2CO3Adjusting the pH value to 7-8 by using ammonia water, stirring for 12 hours, and keeping the temperature of a water bath kettle at 50 ℃.
(3) Centrifuging the mixture obtained in the step (2), and alternately washing 3 times by using absolute ethyl alcohol and deionized water.
(4) And (4) drying the washed solid obtained in the step (3) in an oven at 120 ℃ for 4 h.
(5) The dried solid in the step (4) is put in N2Calcining at 600 ℃ for 3h at the flow rate of 30ml/min to prepare Ru/NMC, and grinding to 20 meshes for later use.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Ru/NMC catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 0.75MPa for reaction, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to yield 99.5% conversion and 96.3% selectivity. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion 98.9% and selectivity 95.6%.
Example 2
The nitrogen-doped carbon sphere support was replaced with a Na-beta type molecular sieve compared to example 1.
(1) Weighing 10g of Na-beta type molecular sieve and RuCl30.5g, added to 30mL of deionized water, and 3g of Na was added to the solution2CO3And adjusting the pH value to 7-8 by using ammonia water, stirring for 12 hours, and keeping the temperature of the water bath kettle at 50 ℃.
(2) Centrifuging the liquid obtained in the step (1), and alternately washing 3 times by using absolute ethyl alcohol and deionized water.
(3) And (3) drying the washed solid obtained in the step (2) in an oven at 120 ℃ for 4 h.
(4) The dried solid in the step (3) is put in N2Calcining at 600 ℃ for 3h at the flow rate of 30ml/min to prepare the Ru/Na-beta type molecular sieve, and grinding to 20 meshes for later use.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5 gRu/Na-beta type molecular sieve catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 0.75MPa, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to give 98.6% conversion and 94.5% selectivity. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion 98.5% and selectivity 93.6%.
Example 3
Compared with example 1, the nitrogen-doped carbon sphere support is replaced by mesoporous silica.
(1) Weighing 10g of mesoporous silica and RuCl30.5g, added to 30mL of deionized water, and 0.3g Na was added to the solution2CO3Adjusting the pH value to 7-8 by using ammonia water, stirring for 12 hours, and keeping the temperature of a water bath kettle at 50 ℃.
(2) Centrifuging the liquid obtained in the step (1), and alternately washing 3 times by using absolute ethyl alcohol and deionized water.
(3) And (3) drying the washed solid obtained in the step (2) in an oven at 120 ℃ for 4 h.
(4) Drying the step (3)Solid in N2Calcining at 600 ℃ for 3h at the flow rate of 30ml/min to prepare Ru/SiO2Grinding to 20 mesh for later use.
10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Ru/SiO2Adding catalyst into high-pressure reactor, N2Replacing three times and filling N2The pressure in the kettle is maintained at 0.75MPa, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to yield a conversion of 95.7% and a selectivity of 94.5%. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion 94.9% and selectivity 94.3%.
Example 4
Comparison with example 1 with MgCl2Replacing RuCl3As a precursor of the active center.
(1) Carbon-doped mesoporous carbon spheres were prepared as in example 1.
(2) 10g of carrier, 0.5g of MgCl were weighed2Adding into 30mL deionized water, adding 3g Na into the solution2CO3Adjusting the pH value to 7-8 by using ammonia water, stirring for 12 hours, and keeping the temperature of a water bath kettle at 50 ℃.
(3) Centrifuging the mixture obtained in the step (2), and alternately washing 3 times by using absolute ethyl alcohol and deionized water.
(4) And (4) drying the washed solid obtained in the step (3) in an oven at 120 ℃ for 4 h.
(5) The dried solid in the step (4) is put in N2Calcining at 600 deg.C for 3h at a flow rate of 30ml/min to prepare Mg/NMC, and grinding to 20 mesh.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Mg/NMC catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 0.75MPa, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to give 99.6% conversion and 97.5% selectivity. After the reaction will be catalyzedThe agent is recovered and dried, and the second reaction gas chromatography analysis is carried out under the same conditions, wherein the conversion rate is 95.3 percent, and the selectivity is 90.8 percent.
Example 5
The reaction temperature was increased to 200 ℃ in the same manner as in the catalyst preparation method of example 1.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Ru/NMC catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 1MPa, and the temperature is controlled by a temperature controller to react for 6h at 200 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to yield 99.5% conversion and 89.3% selectivity. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion 98.9% and selectivity 87.9%.
Example 6
Example 1 the catalyst was prepared in the same manner and the reaction temperature was lowered to 120 ℃.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Ru/NMC catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 0.75MPa, and the temperature is controlled by a temperature controller to react for 6 hours at 120 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to yield a conversion of 86.5% and a selectivity of 93.3%. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion 85.9%, selectivity 90.9%.
Comparative example 1
Replacement of RuCl by aluminium Isobutanolate in comparison with example 13As active center.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutyl alcohol and 0.5g of aluminum isobutyl alcohol catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 0.75MPa, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, the reaction solution is added,cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle, and discharging. The product was analyzed by gas chromatography to obtain 99.3% selectivity and 93.7% selectivity. The catalyst is prepared by reacting iso-dealuminium alkoxide with its ligand-OC4H9Is easy to be substituted by-OH, and then is inactivated after reaction, and cannot be recycled.
Comparative example 2
Example 1 the catalyst preparation process was the same, with the calcination temperature being changed to 800 ℃.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Ru/NMC catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 1MPa, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to give 56.5% conversion and 72.3% selectivity. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion rate was 40.9%, and selectivity was 60.9%.
Comparative example 3
Example 1 the catalyst preparation method was the same, and the calcination temperature was changed to 500 ℃.
Adding 10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Ru/NMC catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained at 1MPa, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to give 65.2% conversion and 73.5% selectivity. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion 60.9%, selectivity 70.9%.
Comparative example 4
Example 1 the catalyst was prepared in the same manner with the active metal replaced by Al.
10g of raw material isobutyraldehyde, 10ml of solvent isobutanol and 0.5g of Al/NMC catalystAdding into a high-pressure reaction kettle, N2Replacing three times and filling N2The pressure in the kettle is maintained at 1MPa, and the temperature is controlled by a temperature controller to react for 6h at 160 ℃. After the reaction is finished, cooling the reaction mixture to room temperature, slowly discharging the inert gas in the kettle, opening the kettle and discharging. The product was analyzed by gas chromatography to yield a conversion of 86.3% and a selectivity of 50.3%. After the reaction, the catalyst was recovered and dried under the same conditions for the second reaction, gas chromatography analysis, conversion rate 73.9%, selectivity 45.9%.
According to the above examples and comparative examples, it can be seen that the monatomic catalyst prepared by the present invention has a good catalytic effect in the isobutyraldehyde Tischenko condensation reaction, and can still maintain a higher catalytic effect in the catalyst recovery and reuse process compared with aluminum isopropoxide.
The raw materials and equipment used in the invention are common raw materials and equipment in the field if not specified; the methods used in the present invention are conventional in the art unless otherwise specified. The foregoing describes alternative embodiments of the invention to teach those skilled in the art how to make and reproduce the invention. Some conventional technical aspects have been simplified and omitted for the purpose of teaching the inventive arrangements. Those skilled in the art will appreciate variations from this aspect that fall within the scope of the invention.

Claims (6)

1. A preparation method of a catalyst for preparing isobutyl isobutyrate by adopting a Tishchenko condensation reaction of isobutyraldehyde is characterized by comprising the following steps:
(1) weighing vector and MClnAdding into deionized water, and mixing with Na2CO3Mixing and placing in a water bath kettle, adjusting the pH value to 7-8 by using ammonia water, and stirring for reaction, wherein M is Ru or Mg;
(2) centrifuging the liquid obtained in the step (1), washing for 3-4 times by using absolute ethyl alcohol, and then drying for 4 hours in a 120 ℃ oven;
(3) putting the solid dried in the step (2) in N2Calcining at the flow rate of 25ml/min, and grinding to 20-30 meshes to obtain the catalyst.
2. The method for preparing the catalyst according to claim 1, wherein the metal chloride in the step (1) is 5 to 6% by mass of the carrier, and Na is2CO3The mass ratio of the metal chloride to the metal chloride is 6: 1.
3. The preparation method of the catalyst according to claim 1, wherein the carrier in the step (1) is one or more of nitrogen-doped carbon spheres, mesoporous silica and Na-beta molecular sieve.
4. The preparation method of the catalyst according to claim 1, wherein the water bath reaction temperature in the step (1) is 50-60 ℃, and the reaction time is 8-12 h.
5. The method for preparing the catalyst according to claim 1, wherein the calcination is performed at 600-700 ℃ for 3 hours in the step (3).
6. A catalyst prepared according to the method of claim 1, which is used for preparing isobutyl isobutyrate by Tishchenko condensation reaction of isobutyraldehyde, and is characterized in that the specific method is as follows: adding raw materials of isobutyraldehyde, solvent of isobutanol and catalyst into a high-pressure reaction kettle, and adding N2Replacing three times and filling N2The pressure in the kettle is maintained, and the reaction is carried out.
CN202111627363.4A 2021-12-28 2021-12-28 Preparation method of catalyst for preparing isobutyl isobutyrate by adopting Tishchenko condensation reaction of isobutyraldehyde Pending CN114210327A (en)

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Citations (6)

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CN107308976A (en) * 2017-07-08 2017-11-03 陕西理工大学 A kind of N doping Carbon Materials load palladium-based catalyst and preparation method and application
CN109718806A (en) * 2017-10-30 2019-05-07 中国科学院大连化学物理研究所 A kind of monatomic catalyst of noble metal and its preparation method and application
CN110283076A (en) * 2019-07-29 2019-09-27 润泰化学股份有限公司 A kind of method that the condensation of low-carbon aldehyde generates low-carbon ester
CN112206808A (en) * 2020-09-30 2021-01-12 润泰化学（泰兴）有限公司 Catalyst for synthesizing isobutyl isobutyrate and preparation method and application thereof
CN113101924A (en) * 2021-04-12 2021-07-13 中国科学院化学研究所 Monoatomic and particle synergistic supported metal catalyst and preparation method and application thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003038962A (en) * 2001-07-27 2003-02-12 Showa Denko Kk Synthesizing catalyst for carboxylates by aldehyde dimerization and method for manufacturing carboxylates
CN107308976A (en) * 2017-07-08 2017-11-03 陕西理工大学 A kind of N doping Carbon Materials load palladium-based catalyst and preparation method and application
CN109718806A (en) * 2017-10-30 2019-05-07 中国科学院大连化学物理研究所 A kind of monatomic catalyst of noble metal and its preparation method and application
CN110283076A (en) * 2019-07-29 2019-09-27 润泰化学股份有限公司 A kind of method that the condensation of low-carbon aldehyde generates low-carbon ester
CN112206808A (en) * 2020-09-30 2021-01-12 润泰化学（泰兴）有限公司 Catalyst for synthesizing isobutyl isobutyrate and preparation method and application thereof
CN113101924A (en) * 2021-04-12 2021-07-13 中国科学院化学研究所 Monoatomic and particle synergistic supported metal catalyst and preparation method and application thereof

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