CN107652425B - Zinc complex catalyst for synthesizing polycyclohexene carbonate - Google Patents
Zinc complex catalyst for synthesizing polycyclohexene carbonate Download PDFInfo
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- CN107652425B CN107652425B CN201711034120.3A CN201711034120A CN107652425B CN 107652425 B CN107652425 B CN 107652425B CN 201711034120 A CN201711034120 A CN 201711034120A CN 107652425 B CN107652425 B CN 107652425B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
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Abstract
The invention discloses a zinc complex catalyst for synthesizing polycyclohexene carbonate, which is a 6-amino-2-methylphenol acetylacetone zinc complex, and 6-amino-2-methylphenol and acetylacetone are used for preparing Schiff base ligands, so that high steric hindrance is provided, a certain surrounding effect is achieved on a zinc metal center, and high activity is achieved. The invention also discloses a method for synthesizing the polycarbonate cyclohexene ester by using the catalyst to catalyze the copolymerization reaction of carbon dioxide and cyclohexene oxide, wherein the reaction temperature is 80-130 ℃, the mass ratio of the catalyst to the cyclohexene oxide is 1: 100-500 after the reaction is carried out for 12-36 hours under the pressure of 2-5 MPa. Under the reaction conditions, the highest catalytic efficiency reaches 192g of polymer/g of catalyst, and the molar content of polycarbonate in the copolymer exceeds 95 percent. The invention does not need to add active hydrogen substances, thereby avoiding the problems of reaction of the active hydrogen substances and the catalyst and reduction of activity.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a zinc complex catalyst for synthesizing polycarbonate cyclohexene ester.
Background
At present, the climate is warming obviously from the observation of global average temperature rise, large-scale ice and snow melting and sea level rise, and the emission reduction problem of greenhouse gases becomes the focus of attention of countries in the world. In 2007, the united nations inter-government specialized committee on climate change (IPCC) issued a fourth evaluation report that it is considered that climate change is very likely to be caused by greenhouse gases emitted by human activities, which has also been widely agreed by governments and experts worldwide.
Annual emission of carbon dioxide in 2008 is 2.94 × 1010Ton of ChinaAnnual emissions have reached 6.55 × 109Ton, 22.3% of global emissions, is the first in the world. In 2010, the development of low-carbon economy in China is in an unprecedented new situation, and the country aims at low-carbon construction wind cloud surge of various industries. Meanwhile, due to the rapid industrialization and urbanization processes, the absolute carbon emission of China is determined to continuously increase for a long time. China is also a considerable challenge to china in the low carbon scenario promised by the government that overall carbon emissions need to peak at 2035 and then decline rapidly, while in the baseline scenario, overall emissions in china will peak at 2045 years.
Therefore, chemical fixation of carbon dioxide has attracted attention, and the copolymerization of carbon dioxide and an epoxy compound to prepare an aliphatic polycarbonate has been a promising research topic in this field. Aliphatic polycarbonates have received great attention as completely degradable, environmentally friendly plastics with both resource utilization and environmental protection, and have become a significant development hotspot in the chemical industry field in recent years. Several thousand and ten thousand ton industrial/semi-industrial production facilities have been built in succession in japan, the united states, china, etc., and some larger scale facilities have also been started or planned to be built. In addition, the application of the aliphatic polycarbonate resin is greatly advanced, and the aliphatic polycarbonate resin is successfully applied to the aspects of disposable packaging materials, tableware, fresh-keeping materials, disposable medical materials, mulching films and the like, and has the potential to be developed into a novel material which is widely applied.
The key of the copolymerization reaction of carbon dioxide and epoxy compounds is the development of a novel catalyst, the cost of various catalysts used at present is high, the catalytic efficiency and the selectivity are unsatisfactory, the cost of aliphatic polycarbonate is high, and the development of the novel catalyst is urgently needed to meet the requirement of industrial production. The high steric hindrance catalyst is simple and convenient to prepare, has high catalytic efficiency, and arouses wide attention of researchers.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a zinc complex catalyst for synthesizing polycyclohexene carbonate, which is a 6-amino-2-methylphenol-acetylacetone zinc complex catalyst, and Schiff base ligands are prepared by using 6-amino-2-methylphenol and acetylacetone, so that high steric hindrance is provided, a certain surrounding effect is achieved on a zinc metal center, and high activity is achieved.
In order to solve the technical problems, the invention adopts the following technical scheme:
a zinc complex catalyst for synthesizing polycyclohexene carbonate is a 6-amino-2-methylphenol zinc acetylacetonate complex, and the structural formula is as follows:
the ligand of the 6-amino-2-methylphenol zinc acetylacetonate complex is 6-amino-2-methylphenol acetylacetonate, the zinc source is diethyl zinc, and the preparation steps are as follows:
(1) dissolving 6-amino-2-methylphenol in methanol, adding acetylacetone into 6-amino-2-methylphenol solution under the protection of nitrogen, heating, refluxing and stirring for 2 hours to obtain ligand 6-amino-2-methylphenol acetylacetone;
(2) putting the 6-amino-2-methylphenol acetylacetone ligand into a container, adding a toluene solution of diethyl zinc under the cooling of an ice salt bath under the protection of nitrogen, stirring for 1-2 h, removing the ice salt bath, stirring for 1h at normal temperature, and pumping out the toluene and unreacted diethyl zinc under reduced pressure to obtain the 6-amino-2-methylphenol acetylacetone zinc complex.
The molar ratio of the 6-amino-2-methylphenol to the acetylacetone in the step (1) is 2: 1.
In the step (2), the molar ratio of the 6-amino-2-methylphenol acetylacetone ligand to the diethyl zinc is 1: 1-1.2.
The method for synthesizing the polycyclohexene carbonate by catalyzing the copolymerization reaction of carbon dioxide and cyclohexene oxide by using the zinc complex catalyst for synthesizing the polycyclohexene carbonate is characterized by comprising the following steps of:
putting the 6-amino-2-methylphenol zinc acetylacetonate complex catalyst into an autoclave, vacuumizing for 1h at 100 ℃, replacing carbon dioxide for several times, cooling to room temperature, adding cyclohexene oxide into the autoclave, heating to 80-130 ℃ in an oil bath, introducing carbon dioxide, keeping the pressure at 2-5 MPa, opening, stirring, reacting for 12-36 h, cooling to room temperature, dissolving the polymer out of the autoclave by using dichloromethane, slowly dropwise adding a dichloromethane solution of the polymer into methanol by using methanol as a precipitator, filtering and collecting precipitated solids, and drying in vacuum to obtain the polycyclohexene carbonate.
The mass ratio of the catalyst to the cyclohexene oxide is 1: 100-500.
The using amount of the methanol is 2-5 times of the mass of a dichloromethane solution of the polymer.
Under the reaction conditions, the aliphatic polycarbonate product can be obtained, the highest catalytic efficiency reaches 192g of polymer/g of catalyst, and the molar content of polycarbonate in the copolymer exceeds 95%.
The invention does not need to add active hydrogen substances, thereby avoiding the problems of reaction of the active hydrogen substances and the catalyst and reduction of activity.
Detailed Description
The present invention will be further described with reference to the following examples. It is to be understood that the following examples are illustrative only and are not intended to limit the scope of the invention, which is to be given numerous insubstantial modifications and adaptations by those skilled in the art based on the teachings set forth above.
Example 1
The preparation method of the zinc complex catalyst 6-amino-2-methylphenol zinc acetylacetonate complex for synthesizing polycyclohexene carbonate of the embodiment is as follows:
(1) weighing 2.46g (0.02 mol) of 6-amino-2-methylphenol, dissolving the 6-amino-2-methylphenol in 15mL of methanol, weighing 1mL (0.01 mol) of acetylacetone under the protection of nitrogen, adding the acetylacetone into the 6-amino-2-methylphenol solution, heating and refluxing in a water bath at 70 ℃, stirring for 2h, and cooling to room temperature to obtain ligand 6-amino-2-methylphenol acetylacetone;
the 6-amino-2-methylphenol acetylacetone ligand is subjected to structural characterization:
1H NMR (400 MHz, CDCl3): 1.5(s, 2H, -CH2),1.82(s, 6H, -CH3), 2.25(s,6H, -CH3), 6.7-7.5(m, 6H, aromatic H),10.2(s, 2H, -OH);
(2) weighing 3.1g (0.01 mol) of 6-amino-2-methylphenol acetylacetone, placing the 6-amino-2-methylphenol acetylacetone into a flask, replacing air in the flask with nitrogen, adding 50mL of toluene to dissolve the 6-amino-2-methylphenol acetylacetone under the protection of nitrogen, then adding a toluene solution (10 vol%) containing 1.235g (0.01 mol) of diethyl zinc into an ice salt bath, stirring for 1h, removing the ice salt bath, stirring for 1h at normal temperature, and pumping away the solvent and unreacted diethyl zinc under reduced pressure to obtain the 6-amino-2-methylphenol acetylacetone zinc complex catalyst.
Example 2
The preparation method of the zinc complex catalyst 6-amino-2-methylphenol zinc acetylacetonate complex for synthesizing polycyclohexene carbonate of the embodiment is as follows:
(1) weighing 2.46g (0.02 mol) of 6-amino-2-methylphenol, dissolving the 6-amino-2-methylphenol in 15mL of methanol, weighing 1mL (0.01 mol) of acetylacetone under the protection of nitrogen, adding the acetylacetone into the 6-amino-2-methylphenol solution, heating and refluxing in a water bath at 70 ℃, stirring for 2h, and cooling to room temperature to obtain ligand 6-amino-2-methylphenol acetylacetone;
the 6-amino-2-methylphenol acetylacetone ligand is subjected to structural characterization:
1H NMR (400 MHz, CDCl3): 1.5(s, 2H, -CH2),1.82(s, 6H, -CH3), 2.25(s,6H, -CH3), 6.7-7.5(m, 6H, aromatic H),10.2(s, 2H, -OH);
(2) weighing 3.1g (0.01 mol) of 6-amino-2-methylphenol acetylacetone, placing the 6-amino-2-methylphenol acetylacetone into a flask, replacing air in the flask with nitrogen, adding 50mL of toluene to dissolve the 6-amino-2-methylphenol acetylacetone under the protection of nitrogen, then adding a toluene solution (10 vol%) containing 1.482g (0.012 mol) of diethyl zinc into an ice salt bath, stirring for 1h, removing the ice salt bath, stirring for 1h at normal temperature, and pumping away the solvent and unreacted diethyl zinc under reduced pressure to obtain the 6-amino-2-methylphenol acetylacetone zinc complex catalyst.
Example 3
The method for synthesizing the polycyclohexene carbonate by using the 6-amino-2-methylphenol acetylacetone zinc complex prepared in the example 1 to catalyze the copolymerization reaction of carbon dioxide and cyclohexene oxide is characterized by comprising the following steps:
weighing 0.1g of 6-amino-2-methylphenol zinc acetylacetonate complex catalyst, placing the catalyst into an autoclave, vacuumizing for 1h at 100 ℃, replacing carbon dioxide for several times, cooling to room temperature, adding 10g of cyclohexene oxide into the autoclave, heating in an oil bath to 80 ℃, filling carbon dioxide, keeping the pressure at 3MPa, opening and stirring, reacting for 24h, cooling to room temperature, stopping the reaction, dissolving the polymer out of the autoclave by using 20mL of dichloromethane, using methanol as a precipitator, slowly dropwise adding a dichloromethane solution of the polymer into 100mL of methanol, filtering and collecting precipitated solids, and drying in vacuum by using a vacuum drying oven to obtain 8.3g of polymer aliphatic polycarbonate with the molar content of 95%.
Example 4
The method for synthesizing the polycyclohexene carbonate by using the 6-amino-2-methylphenol acetylacetone zinc complex prepared in the example 2 to catalyze the copolymerization reaction of carbon dioxide and cyclohexene oxide is characterized by comprising the following steps:
0.1g of 6-amino-2-methylphenol zinc acetylacetonate complex catalyst was weighed out and placed in an autoclave, and vacuum was applied at 100 ℃ for 1 hour to displace carbon dioxide several times, and the mixture was cooled to room temperature. Adding 40g of cyclohexene oxide into a kettle, heating to 110 ℃ in an oil bath, introducing carbon dioxide, keeping the pressure at 4MPa, opening and stirring, reacting for 24 hours, cooling to room temperature, stopping the reaction, dissolving out the polymer from the autoclave by using 30mL of dichloromethane, using methanol as a precipitator, slowly dropwise adding a dichloromethane solution of the polymer into 200mL of methanol, filtering and collecting precipitated solids, and performing vacuum drying at 50 ℃ by using a vacuum drying oven to obtain 19.2g of polymer aliphatic polycarbonate, wherein the molar content of the polycarbonate is 96%.
Example 5
The method for synthesizing the polycyclohexene carbonate by using the 6-amino-2-methylphenol acetylacetone zinc complex prepared in the example 1 to catalyze the copolymerization reaction of carbon dioxide and cyclohexene oxide is characterized by comprising the following steps:
0.1g of 6-amino-2-methylphenol zinc acetylacetonate complex catalyst was weighed out and placed in an autoclave, and vacuum was applied at 100 ℃ for 1 hour to displace carbon dioxide several times, and the mixture was cooled to room temperature. Adding 50g of cyclohexene oxide into a kettle, heating to 130 ℃ in an oil bath, introducing carbon dioxide, keeping the pressure at 5MPa, opening and stirring, reacting for 36 hours, cooling to room temperature, stopping the reaction, dissolving out the polymer from an autoclave by using 30mL of dichloromethane, using methanol as a precipitator, slowly dropwise adding a dichloromethane solution of the polymer into 200mL of methanol, filtering and collecting precipitated solids, and performing vacuum drying at 50 ℃ by using a vacuum drying oven to obtain 16.7g of polymer aliphatic polycarbonate, wherein the molar content of the polycarbonate is 98%.
Example 6
The method for synthesizing the polycyclohexene carbonate by using the 6-amino-2-methylphenol acetylacetone zinc complex prepared in the example 2 to catalyze the copolymerization reaction of carbon dioxide and cyclohexene oxide is characterized by comprising the following steps:
0.1g of 6-amino-2-methylphenol zinc acetylacetonate complex catalyst was weighed out and placed in an autoclave, and vacuum was applied at 100 ℃ for 1 hour to displace carbon dioxide several times, and the mixture was cooled to room temperature. Adding 20g of cyclohexene oxide into a kettle, heating the kettle to 100 ℃ in an oil bath, introducing carbon dioxide, keeping the pressure at 4MPa, opening and stirring the kettle, reacting for 12 hours, cooling the kettle to room temperature, stopping the reaction, dissolving out the polymer from the autoclave by using 20mL of dichloromethane, using methanol as a precipitator, slowly dropwise adding a dichloromethane solution of the polymer into 200mL of methanol, filtering and collecting precipitated solids, and performing vacuum drying at 50 ℃ by using a vacuum drying oven to obtain 9.6g of polymer aliphatic polycarbonate, wherein the molar content of the polycarbonate is 95%.
The foregoing shows and describes the general principles and features of the present invention, together with the advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (7)
1. A zinc complex catalyst for synthesizing polycyclohexene carbonate is a 6-amino-2-methylphenol zinc acetylacetonate complex, and the structural formula is as follows:
2. the catalyst of claim 1, wherein the ligand of the zinc 6-amino-2-methylphenol acetylacetonate complex is 6-amino-2-methylphenol acetylacetonate, the zinc source is diethyl zinc, and the preparation steps are as follows:
(1) dissolving 6-amino-2-methylphenol in methanol, adding acetylacetone into 6-amino-2-methylphenol solution under the protection of nitrogen, heating, refluxing and stirring for 2 hours to obtain ligand 6-amino-2-methylphenol acetylacetone;
(2) putting the 6-amino-2-methylphenol acetylacetone ligand into a container, adding a toluene solution of diethyl zinc under the cooling of an ice salt bath under the protection of nitrogen, stirring for 1-2 h, removing the ice salt bath, stirring for 1h at normal temperature, and pumping out the toluene and unreacted diethyl zinc under reduced pressure to obtain the 6-amino-2-methylphenol acetylacetone zinc complex.
3. The zinc complex catalyst for synthesizing polycyclohexene carbonate according to claim 2, wherein: the molar ratio of the 6-amino-2-methylphenol to the acetylacetone in the step (1) is 2: 1.
4. The zinc complex catalyst for synthesizing polycyclohexene carbonate according to claim 2, wherein: in the step (2), the molar ratio of the 6-amino-2-methylphenol acetylacetone ligand to the diethyl zinc is 1: 1-1.2.
5. The method for synthesizing the polycyclohexene carbonate by catalyzing the copolymerization reaction of carbon dioxide and cyclohexene oxide by using the zinc complex catalyst for synthesizing the polycyclohexene carbonate as claimed in claim 1, which is characterized by comprising the following steps:
putting the 6-amino-2-methylphenol zinc acetylacetonate complex catalyst into an autoclave, vacuumizing for 1h at 100 ℃, replacing carbon dioxide for several times, cooling to room temperature, adding cyclohexene oxide into the autoclave, heating to 80-130 ℃ in an oil bath, introducing carbon dioxide, keeping the pressure at 2-5 MPa, opening, stirring, reacting for 12-36 h, cooling to room temperature, dissolving the polymer out of the autoclave by using dichloromethane, slowly dropwise adding a dichloromethane solution of the polymer into methanol by using methanol as a precipitator, filtering and collecting precipitated solids, and drying in vacuum to obtain the polycyclohexene carbonate.
6. The method of claim 5, wherein: the mass ratio of the catalyst to the cyclohexene oxide is 1: 100-500.
7. The method of claim 5, wherein: the using amount of the methanol is 2-5 times of the mass of a dichloromethane solution of the polymer.
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Inventor after: Qin Gang Inventor after: Liu Zejun Inventor after: Fan Lidan Inventor after: Wang Libo Inventor after: Shen Zhongshuo Inventor after: Chen Juan Inventor after: Wang Changying Inventor after: Wang Yijie Inventor before: Fan Lidan Inventor before: Liu Zejun Inventor before: Qin Gang Inventor before: Wang Libo Inventor before: Shen Zhongshuo Inventor before: Chen Juan |
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