CN115724726A - Method for directly preparing ketone by olefin carbonylation - Google Patents

Method for directly preparing ketone by olefin carbonylation Download PDF

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CN115724726A
CN115724726A CN202110986858.XA CN202110986858A CN115724726A CN 115724726 A CN115724726 A CN 115724726A CN 202110986858 A CN202110986858 A CN 202110986858A CN 115724726 A CN115724726 A CN 115724726A
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olefin
catalyst
alcohol
reaction
carbon monoxide
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王峰
郭强
王业红
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Dalian Institute of Chemical Physics of CAS
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Dalian Institute of Chemical Physics of CAS
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    • 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
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    • Y02P20/584—Recycling of catalysts

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Abstract

The invention relates to a method for directly preparing ketone by olefin carbonylation, which adopts olefin, carbon monoxide and alcohol as reaction substrates and directly prepares ketone under the action of a catalyst. The reaction process is as follows: after mixing olefin, alcohol and catalyst, putting the mixture into a pressure container, sealing the pressure container, introducing carbon monoxide, stirring the mixture, wherein the reaction temperature is higher than 100 ℃, the reaction time is longer than 0.5 hour, the catalyst and the reaction system after the reaction are easy to separate and can be recycled for a plurality of times, and the separation yield of ketone can reach 90 percent at most.

Description

Method for directly preparing ketone by olefin carbonylation
Technical Field
The invention relates to a method for preparing ketone, in particular to the preparation of ketone by carbonylation and carbon-carbon coupling reaction of olefin and carbon monoxide.
Background
Ketones are important organic compounds, are used as solvents, and are widely applied to the fields of coatings, oil refining, dyes, medical industry and the like; can also be used for various organic syntheses and used as raw materials and intermediates for synthesizing perfumes and medicines. The current methods for preparing ketones mainly include: oxidation of secondary alcohols, hydration of alkynes, ozonolysis of alkenes, and ketonization reactions, among others. CN104174397-A reports that acetone is prepared by decarboxylation of acetic acid and ketonization after ferric oxide or cobalt oxide is loaded on zirconium oxide/titanium oxide; CN1765490 (A) discloses a method for preparing ketone by decarboxylation ketonization of C2-C12 carboxylic acid; US20130190535 (A1) reports a strategy for the decarboxylation of carboxylic acid esters and carboxylic acids to produce ketones; CN201210043948.6 adopts a dehydrogenation strategy, and realizes the synthesis of cyclopentanone through cyclopentanol dehydrogenation; the preparation of cerium oxide catalyzed decarboxylation of propionic acid to 3-pentanone using Ce-UiO-66 as a precursor is reported in INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,2020,59, 17269. However, these methods usually require a relatively severe reaction condition and produce one molecule of carbon dioxide (decarboxylated ketonization). Therefore, the development of a technical route for preparing the ketone with high efficiency and low cost has important scientific significance and application background.
Disclosure of Invention
The invention provides a new way for synthesizing ketone, and the ketone compound is efficiently prepared under mild conditions, and the catalyst is easy to separate and can be recycled for many times.
The ketones to which the present invention relates are prepared by the following scheme:
mixing olefin, alcohol and supported metal catalyst, sealing in a pressure container, introducing CO, stirring at reaction temperature not lower than 100 deg.c for reaction time not lower than 0.5 hr to obtain ketone as the reaction product.
The feeding molar ratio of the alcohol to the olefin is 2-200; the pressure of the carbon monoxide is 0.1 to 5Mpa;
the olefin is one or more of C2-C10 olefins;
the alcohol is one or two or more of monohydric alcohol, dihydric alcohol or trihydric and higher polyhydric alcohol;
the supported metal catalyst, wherein the carrier comprises an oxide MoO 3 、WO 3 、TiO 2 、ZrO 2 、SnO 2 、Nb 2 O 5 、Al 2 O 3 、Fe 2 O 3 、Fe 3 O 4 、La 2 O 3 And CeO 2 (ii) a One or two or more of molecular sieves ZSM-5, Y, FER, MOR and Beta;
the metals include: one or more of Co, rh, ir, ni, pd, pt, cu, ag, au, fe, ru and Os;
the mass loading of the active metals in the catalyst is as follows: 0.01 to 10 percent.
The catalyst was used in an amount of 0.02g (mmol of olefin) -1 About 0.4g x (mmol of olefin) -1 ；
The reaction temperature is 100-220 ℃;
the reaction time is 0.5-24h.
Preferably, the following steps are carried out: the feeding molar ratio of the alcohol to the olefin is 6-120; the pressure of the carbon monoxide is 0.3 to 3Mpa;
the olefin is: one or two or more of ethylene, propylene, 1-butene, 1, 3-butadiene, styrene and cyclohexene;
the alcohol is: one or more of ethanol, isopropanol, 2-butanol, 3-pentanol and ethylene glycol;
the supported metal catalyst wherein the support comprises the oxide TiO 2 、ZrO 2 、SnO 2 、Nb 2 O 5 、La 2 O 3 And CeO 2 (ii) a One or more than two of molecular sieves ZSM-5 and Beta;
the metal includes: one or two or more of Co, rh, ir, ni, pd, pt and Ru.
The mass loading of the active metals in the catalyst is as follows: 0.2 to 2 percent.
The catalyst was used in an amount of 0.03g (mmol of olefin) -1 About 0.2g x (mmol of olefin) -1 ；
The reaction temperature is 120-180 ℃;
the reaction time is 1-12 h.
The best is as follows: the feeding molar ratio of the alcohol to the olefin is 8-80; the pressure of the carbon monoxide is 0.4 to 2Mpa;
the alcohol is: one or more of ethanol, isopropanol, 2-butanol, and 3-pentanol;
the olefin is: one or more of ethylene, propylene, 1, 3-butadiene, styrene and cyclohexene;
the supported metal catalyst has TiO carrier 2 、SnO 2 、Nb 2 O 5 、CeO 2 And ZSM-5;
the metal includes: one or two or more of Co, rh, ir and Pd.
The mass loading of the active metals in the catalyst is as follows: 0.5 to 1 percent. The catalyst was used in an amount of 0.05g (mmol of olefin) -1 About 0.1g x (mmol of olefin) -1 ；
The reaction temperature is 130-170 ℃;
the reaction time is 2-6 h.
The method has the advantages that the ketone is obtained in one step through the carbonylation reaction of the olefin, and the yield of the ketone is high and can reach 90 percent; the catalyst is simple to prepare, is easy to separate from a reaction system, and can be recycled for multiple times; the product has wide variety and is suitable for most of ketones.
Detailed Description
In order to further explain the present invention in detail, some specific examples are given below, but the present invention is not limited to these examples.
Example 1
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 1g of 0.5wt% -Pd/TiO is weighed 2 Adding 30ml of methanol and 30mmol of propylene into a catalyst (0.5 wt% represents the mass loading of active metals in the catalyst), charging 1Mpa of carbon monoxide, stirring and reacting for 16 hours at 200 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of propylene was 60%, and the yields of ketones (4-heptanone, 2-methyl-3-hexanone and 2, 4-dimethylpentanone) were: 55 percent of 4-heptanone 28 percent, 2-methyl-3-hexanone 14 percent and 2, 4-dimethyl pentanone 13 percent, and the rest products are methyl n-butyrate and methyl isobutyrate mainly.
Example 2
In a 200ml reaction kettle with a polytetrafluoroethylene lining, weighing 1g of 1wt% -Co/TiO 2 Adding 30ml ethanol and 30mmol ethylene into catalyst, charging 1Mpa carbon monoxide, at 180 deg.CStirring and reacting for 24h, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of ethylene was 75% and the yield of ketone (3-pentanone) was: 72% and the remainder being predominantly ethyl propionate.
Example 3
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.6g of 0.5wt% -Rh/TiO is weighed 2 Adding 30ml of ethanol and 30mmol of ethylene into the catalyst, charging 1Mpa of carbon monoxide, stirring and reacting for 24 hours at 160 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of ethylene was 85% and the yield of ketone (3-pentanone) was: 81% and the remainder being predominantly ethyl propionate.
Example 4
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.5g of 0.5wt% -Rh/CeO is weighed 2 Adding 30ml of ethanol and 30mmol of ethylene into the catalyst, charging 1.5Mpa of carbon monoxide, stirring and reacting for 16 hours at 180 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of ethylene was 88% and the yield of ketone (3-pentanone) was: 85% and the rest products are mainly ethyl propionate.
Example 5
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 1g of 1wt% -Co/CeO is weighed 2 Adding 30ml of ethanol and 30mmol of propylene into the catalyst, charging 1.5Mpa of carbon monoxide, stirring and reacting for 24h at 200 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of propylene was 55%, the yield of ketone was: 53% of which are 26% of 4-heptanone, 14% of 2-methyl-3-hexanone, 13% of 2, 4-dimethylpentanone and the balance being predominantly ethyl n-butyrate and ethyl isobutyrate.
Example 6
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 1g of 1wt% -Ir/CeO is weighed 2 Adding 30ml of isopropanol and 30mmol of propylene into the catalyst, introducing 1Mpa of carbon monoxide, stirring and reacting for 16h at 200 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of propylene was 70%, the yield of ketone was: 66% of 4-heptanone 33%, 2-methyl-3-hexanone17 percent, 16 percent of 2, 4-dimethyl pentanone and the rest products are mainly isopropyl n-butyrate and isopropyl isobutyrate.
Example 7
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 1g of 1wt% -Rh/CeO is weighed 2 Adding 30ml of isopropanol and 30mmol of ethylene into the catalyst, charging 1.5Mpa of carbon monoxide, stirring and reacting for 20 hours at 170 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of ethylene was 95% and the yield of ketone (3-pentanone) was: 90% and the remainder is mainly isopropyl propionate.
Example 8
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.5g of 0.5wt% -Rh/SnO is weighed 2 Adding 30ml of isopropanol and 30mmol of propylene into the catalyst, introducing 1Mpa of carbon monoxide, stirring and reacting for 16h at 180 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The conversion of propylene was 70% and the yield of ketone was: 65% of the total weight of the components, wherein 32% of 4-heptanone, 17% of 2-methyl-3-hexanone, 16% of 2, 4-dimethyl pentanone, and the balance of the components are mainly isopropyl n-butyrate and isopropyl isobutyrate.
Example 9
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.5g of 1wt% -Rh/CeO 2 Adding 30ml 2-butanol and 30mmol ethylene into catalyst, introducing 1Mpa carbon monoxide, stirring at 160 deg.C for 16 hr, filtering, and detecting by gas chromatography. The conversion of ethylene was 95% and the yield of ketone (3-pentanone) was: 90% and the remainder being predominantly 2-butyl propionate.
Example 10
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.5g of 1wt% -Rh/CeO 2 Adding 30ml ethanol and 30mmol 1, 3-butadiene into the catalyst, charging 1.5Mpa carbon monoxide, stirring and reacting at 200 deg.C for 16h, filtering the catalyst after the reaction is finished, and detecting the product by gas chromatography. The conversion of 1, 3-butadiene was 50%, and the yield of ketone (cyclopentanone) was: 45 percent, and the rest products are mainly ethyl 3-pentenoate.
Example 11
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.5g of 1wt% -Rh/CeO 2 Adding 30ml of methanol and 30mmol of cyclohexene into the catalyst, charging 2Mpa of carbon monoxide, stirring and reacting for 16 hours at 200 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The cyclohexene conversion was 60%, the yield of ketone (dicyclohexyl ketone) was: 55 percent, and the rest products are mainly methyl cyclohexanoate.
Example 12
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.6g of 1wt% -Rh/TiO is weighed 2 Adding 30ml of isopropanol and 30mmol of 1, 3-butadiene into the catalyst, charging 1.5Mpa of carbon monoxide, stirring and reacting for 24h at 180 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using a gas chromatography. The conversion of 1, 3-butadiene was 50%, and the yield of ketone (cyclopentanone) was: 43% and the remainder being predominantly isopropyl 3-pentenoate.
Example 13
In a 200ml reaction kettle with a polytetrafluoroethylene lining, 0.5g of 1wt% -Rh/CeO is weighed 2 Adding 30ml 2-butanol and 30mmol 1, 3-butadiene into catalyst, charging 2Mpa carbon monoxide, stirring at 200 deg.C for reaction for 16h, filtering catalyst after reaction, and detecting product by gas chromatography. The conversion of 1, 3-butadiene was 55%, and the yield of ketone (cyclopentanone) was: 51% and the rest is mainly 3-pentenoic acid-2-butyl ester.
Example 14
In 20 ml reaction kettle with polytetrafluoroethylene lining, 1g of 1wt% -Co/SnO is weighed 2 Adding 30ml of isopropanol and 30mmol of cyclohexene into the catalyst, charging 1.5Mpa of carbon monoxide, stirring and reacting for 24 hours at 170 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The cyclohexene conversion was 66%, the yield of ketone (dicyclohexyl ketone) was: 61% and the remainder is predominantly isopropyl cyclohexanoate.
Example 15
In 20 ml reaction kettle with polytetrafluoroethylene lining, 1g of 0.5wt% -Pd/SnO is weighed 2 Adding 30ml 2-butanol and 30mmol cyclohexene in catalyst, charging 2Mpand c, stirring the carbon monoxide at 200 ℃ for reaction for 20 hours, filtering the catalyst after the reaction is finished, and finally detecting the product by using gas chromatography. The cyclohexene conversion was 62%, the yield of ketone (dicyclohexyl ketone) was: 55 percent, and the rest products are mainly cyclohexanoic acid-2-butyl ester.
Comparative example 1
100ummol of Pd [ P (C) was charged into a 20 ml Teflon lined reactor 6 H 5 ) 3 ] 4 Adding 30ml of ethanol and 30mmol of ethylene, charging 1Mpa of carbon monoxide, stirring and reacting for 16h at 170 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by gas chromatography. The conversion of ethylene was 30% and the yield of ketone (3-pentanone) was: 15% and the rest products are mainly ethyl propionate and propionaldehyde diethyl acetal.
Comparative example 2
In a 20 ml Teflon lined reactor, 100ummol of RhCl (PPh) was taken 3 ) 3 Adding 30ml of ethanol and 30mmol of ethylene, charging 1.5Mpa of carbon monoxide, stirring at 180 ℃ for reaction for 24 hours, filtering the catalyst after the reaction is finished, and finally detecting the product by gas chromatography. The conversion of ethylene was 52% and the yield of ketone (3-pentanone) was: 26% and the rest products are mainly ethyl propionate and propionaldehyde diethyl acetal.
Comparative example 3
100ummol of Ru is taken in a 20 ml reaction kettle with polytetrafluoroethylene lining 3 (CO) 12 Adding 30ml of ethanol and 30mmol of ethylene, charging 1Mpa of carbon monoxide, stirring and reacting for 16h at 200 ℃, filtering the catalyst after the reaction is finished, and finally detecting the product by gas chromatography. The conversion of ethylene was 40% and the yield of ketone (3-pentanone) was: 17% and the rest products are mainly ethyl propionate and propionaldehyde diethyl acetal.

Claims (8)

1. A process for the direct preparation of ketones by carbonylation of olefins, characterized by:
mixing olefin, alcohol and supported metal catalyst, sealing in a pressure container, introducing CO, stirring at reaction temperature not lower than 100 deg.c for 0.5 hr.
2. The method of claim 1, wherein:
the feeding molar ratio of the alcohol to the olefin is 2-200; the pressure of the carbon monoxide is 0.1 to 5Mpa;
the olefin is one or two or more of C2-C10 olefins;
the alcohol is one or two or more of monohydric alcohol, dihydric alcohol or trihydric or higher polyhydric alcohol;
the catalyst is a supported metal catalyst, wherein the carrier is oxide MoO 3 、WO 3 、TiO 2 、ZrO 2 、SnO 2 、Nb 2 O 5 、Al 2 O 3 、Fe 2 O 3 、Fe 3 O 4 、La 2 O 3 And CeO 2 (ii) a One or more of molecular sieves ZSM-5, Y, FER, MOR and Beta;
the supported active metals are: one or two or more of Co, rh, ir, ni, pd, pt, cu, ag, au, fe, ru and Os;
the mass loading of the active metals in the catalyst is as follows: 0.01% -10%;
the reaction temperature is 100-220 ℃; the preferred reaction temperature is 150 ℃.
3. A method according to claim 1 or 2, characterized in that:
the feeding molar ratio of the alcohol to the olefin is 4-160; the pressure of the carbon monoxide is 0.2 to 4Mpa;
the olefin is: one or more of ethylene, propylene, 1-butene, isobutene, 1, 3-butadiene, 1-pentene, 3-methyl-1-butene, styrene, alpha-methylstyrene and cyclohexene;
the alcohol is: one or two or more of ethanol, isopropanol, 2-butanol, 3-pentanol, ethylene glycol and glycerol;
the supported metal catalyst has MoO as carrier 3 、TiO 2 、ZrO 2 、SnO 2 、Nb 2 O 5 、Al 2 O 3 、La 2 O 3 And CeO 2 (ii) a One or two or more of molecular sieves ZSM-5, Y and Beta;
the metal is one or two or more of Co, rh, ir, ni, pd, pt, ag, au and Ru;
the mass loading of the active metals in the catalyst is as follows: 0.1 to 5 percent;
the reaction temperature is 110-200 ℃.
4. A method according to claim 1 or 2, characterized in that:
the feeding molar ratio of the alcohol to the olefin is 6-120; the pressure of the carbon monoxide is 0.3 to 3Mpa;
the olefin is: one or two or more of ethylene, propylene, 1-butene, 1, 3-butadiene, styrene and cyclohexene;
the alcohol is: one or two or more of ethanol, isopropanol, 2-butanol, 3-pentanol and ethylene glycol;
the supported metal catalyst has TiO carrier 2 、ZrO 2 、SnO 2 、Nb 2 O 5 、La 2 O 3 And CeO 2 (ii) a One or two or more of molecular sieves ZSM-5 and Beta;
the metal is one or two or more of Co, rh, ir, ni, pd, pt and Ru;
the mass loading of the active metals in the catalyst is as follows: 0.2% -2%;
the reaction temperature is 120-180 ℃.
5. A method according to claim 1 or 2, characterized in that:
the feeding molar ratio of the alcohol to the olefin is 8-80; the pressure of the carbon monoxide is 0.4 to 2Mpa;
the alcohol is: one or more of ethanol, isopropanol, 2-butanol, and 3-pentanol;
the olefin is: one or two or more of ethylene, propylene, 1, 3-butadiene, styrene and cyclohexene;
the supported metal catalyst has TiO as carrier 2 、SnO 2 、Nb 2 O 5 、CeO 2 And ZSM-5;
the metal is one or two or more of Co, rh, ir and Pd;
the mass loading of the active metals in the catalyst is as follows: 0.5 to 1 percent;
the reaction temperature is 130-170 ℃.
6. The method of claim 1, wherein:
the catalyst was used in an amount of 0.02g (mmol of olefin) -1 About 0.4g x (mmol of olefin) -1 ；
The reaction time is 0.5-24h.
7. The method of claim 1 or 6, wherein:
the catalyst was used in an amount of 0.03g (mmol of olefin) -1 About 0.2g star (mmol olefin) -1 ；
The reaction time is 1-12 h.
8. The method of claim 1 or 6, wherein:
the catalyst was used in an amount of 0.05g (mmol of olefin) -1 About 0.1g star (mmol olefin) -1 ；
The reaction time is 2-6 h.
CN202110986858.XA 2021-08-26 2021-08-26 Method for directly preparing ketone by olefin carbonylation Pending CN115724726A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2545821A1 (en) * 1983-05-13 1984-11-16 Ugine Kuhlmann Process for the manufacture of ketones by catalytic carbonylation of olefins
US4879417A (en) * 1987-08-03 1989-11-07 Shell Oil Company Process for carbonylation of alkenes to ketones
US5126490A (en) * 1990-11-28 1992-06-30 Princeton University Process for the catalytic oxidation of olefins to carbonyl compounds
CN1155881A (en) * 1994-07-13 1997-07-30 巴斯福股份公司 Process for carbonylating olefins
CN108003022A (en) * 2016-11-02 2018-05-08 中国科学院大连化学物理研究所 A kind of method for preparing ester type compound
CN112979440A (en) * 2019-12-12 2021-06-18 中国科学院大连化学物理研究所 Application of supported catalyst in reaction of synthesizing ketone by olefin carbonylation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2545821A1 (en) * 1983-05-13 1984-11-16 Ugine Kuhlmann Process for the manufacture of ketones by catalytic carbonylation of olefins
US4879417A (en) * 1987-08-03 1989-11-07 Shell Oil Company Process for carbonylation of alkenes to ketones
US5126490A (en) * 1990-11-28 1992-06-30 Princeton University Process for the catalytic oxidation of olefins to carbonyl compounds
CN1155881A (en) * 1994-07-13 1997-07-30 巴斯福股份公司 Process for carbonylating olefins
CN108003022A (en) * 2016-11-02 2018-05-08 中国科学院大连化学物理研究所 A kind of method for preparing ester type compound
CN112979440A (en) * 2019-12-12 2021-06-18 中国科学院大连化学物理研究所 Application of supported catalyst in reaction of synthesizing ketone by olefin carbonylation

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