CN115028824B - Preparation method of carbon dioxide-based polycarbonate polyol product - Google Patents
Preparation method of carbon dioxide-based polycarbonate polyol product Download PDFInfo
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- CN115028824B CN115028824B CN202210650678.9A CN202210650678A CN115028824B CN 115028824 B CN115028824 B CN 115028824B CN 202210650678 A CN202210650678 A CN 202210650678A CN 115028824 B CN115028824 B CN 115028824B
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
The invention discloses a preparation method of a carbon dioxide-based polycarbonate polyol product, which comprises the following two steps: (1) Synthesis of catalyst: adding urea, 5-hydroxymethylfurfural, triethylamine and N, N-dimethylformamide for dissolution and reaction; after reduced pressure distillation, zinc acetate and cobalt oxalate are added to obtain a catalyst system; (2) Synthesis of polycarbonate polyol: introducing nitrogen to remove air in the system, dropwise adding an initiator, propylene oxide and ethylene oxide, introducing carbon dioxide, heating and stirring for reaction; and after the reaction is finished, adding the polycarbonate polyol, adjusting the pH, filtering, and distilling under reduced pressure to obtain a polycarbonate polyol product. The invention realizes the controllable synthesis of the carbon dioxide-based polycarbonate polyol product, has the advantages of short preparation process route, safe and nontoxic catalyst, chemical carbon fixation, adjustable hydroxyl value and viscosity of the product, stable performance, biodegradability and the like, can be independently used as a raw material for producing polyurethane materials, and can also be mixed with other polyols for use.
Description
Technical Field
The invention relates to the technical field of polyol synthesis, in particular to a preparation method of a carbon dioxide-based polycarbonate polyol product suitable for polyurethane foaming.
Background
With the rapid development of modern industrial civilization, the consumption of fossil energy sources such as coal, petroleum, natural gas and the like by human beings is increased year by year, and the amount of carbon dioxide discharged into the environment is also obviously increased, which causes adverse effects such as global temperature rise, abnormal weather phenomenon increase and the like. On the other hand, as the use amount of plastic products such as polyethylene, polyvinyl chloride and the like increases, the degradation time of the polymer materials in the environment needs hundreds of years or even longer, and micro plastics generated in the degradation process also enter living things such as plankton, fish, shrimp and the like, thereby threatening the survival and development of human beings. Therefore, the development of emission reduction and resource utilization of carbon dioxide and the synthesis of degradable materials in natural environment have important practical significance, and can provide a material basis for sustainable development of human society.
The treatment method of carbon dioxide is mainly divided into two major categories, namely a physical method of compression deep storage and a chemical method of synthesizing new materials. The former is simply the transfer of carbon dioxide from one location to another, and thorough remediation is not achieved, and there is still a risk of leakage. The synthesis of bulk chemicals such as methanol, ethanol, polycarbonate and the like by taking carbon dioxide as a raw material has good economic benefit, social benefit and environmental benefit, and has become one of the leading edge and hot spot problems of current scientific research and technical innovation. Since the Japanese academy of 1969 realized that carbon dioxide and propylene oxide are polymerized in a laboratory to obtain polycarbonate polyol, the synthetic route has been continuously focused and studied, and the product can be used for synthesizing polyurethane materials such as sofa mattresses and the like, mulch films required by agricultural production, food preservative films and the like in various fields. However, due to the limitations of technology, cost, environmental protection and other factors, the example of large-scale industrial production is still lacking at present, and the productivity can not meet the demands of human beings.
Polyols refer to a class of organic compounds containing two or more hydroxyl functional groups in the molecular structure and can be classified into polyether polyols, polyester polyols and polymer polyols. The general polyether polyol is prepared by polymerizing an initiator (such as glycerol, 1, 3-propylene glycol, ethylene glycol, sucrose and the like) and an alkylene oxide (such as ethylene oxide, propylene oxide, single components or a mixture of the two) under the action of an alkaline catalyst (such as NaOH and KOH), and has the advantages of smaller molecular weight, wider distribution and higher double bond content. The later developed double metal cyanide complex catalyst (DMC) can obtain products with larger molecular weight and narrower distribution, and the catalyst dosage is less, and the catalyst is generally not required to be removed from the products after the reaction is finished. However, DMC catalyst is cyanide, the waste water produced in the process of synthesizing polyol product needs to be deeply treated, and the treatment cost is high. In addition, cyanide can generate highly toxic hydrocyanic acid under acidic conditions, and the catalyst has potential safety hazards in the processes of storage, transportation and use.
Therefore, research and development of a novel environment-friendly catalytic material can realize copolymerization of carbon dioxide and propylene oxide/ethylene oxide under mild conditions so as to obtain a polycarbonate polyol product, and the novel environment-friendly catalytic material has important scientific research value and good market application prospect.
Disclosure of Invention
The invention aims to provide a preparation method of a carbon dioxide-based polycarbonate polyol product, which utilizes a chemical method to synthesize a novel catalyst, and embeds cheap carbon dioxide molecules into a propylene oxide/ethylene oxide molecular structure to obtain a biodegradable polycarbonate polyol product. The technology can realize the resource utilization of carbon dioxide and reduce the content of carbon dioxide in the atmosphere environment, and the obtained polycarbonate polyol product has the advantages of short preparation process, adjustable hydroxyl value and viscosity, biodegradability and the like, can be independently used as a raw material for synthesizing polyurethane and other materials, can be used by being compounded with other polyols, and has good economic benefit, social benefit and environmental benefit.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
(1) And (3) synthesizing a catalyst: adding urea, 5-hydroxymethylfurfural, triethylamine and N, N-dimethylformamide into a high-pressure reaction kettle according to a certain proportion, heating, stirring and dissolving the urea and the 5-hydroxymethylfurfural to react; removing water and triethylamine through reduced pressure distillation, and then adding zinc acetate and cobalt oxalate to obtain a catalyst system; the catalyst is a metal organic compound catalyst;
(2) Synthesis of polycarbonate polyol: introducing nitrogen into the catalyst system to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, and heating and stirring to react; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product.
In the step (1), the molar ratio of urea, 5-hydroxymethylfurfural, triethylamine and N, N-dimethylformamide is 1:2:0.001:1, the mole ratio of urea, zinc acetate and cobalt oxalate is 1:2:1.
in the step (1), the reaction temperature of urea and 5-hydroxymethylfurfural is 60-90 ℃ and the reaction time is 1-3 h; the reduced pressure distillation temperature was 60℃and the reduced pressure distillation time was 2 hours.
In the step (2), the initiator is 1, 4-butanediol or glycerol, and the molar ratio of the initiator to the propylene oxide to the ethylene oxide is 0.001:2: (1-0.1).
In the step (2), the pressure of the system is 3.8-5.6 Mpa after adding carbon dioxide.
In the step (2), the catalyst dosage is 0.1-0.5% of the total mass of the epoxypropane and the epoxyethane.
In the step (2), the reaction temperature for synthesizing the polycarbonate polyol is 90-120 ℃ and the reaction time is 3-8 h.
In the step (2), sodium hydroxide is adopted to adjust the pH value of the product to 7-8; the reduced pressure distillation temperature is 110 ℃ and the time is 2h.
The functionality of hydroxyl groups in the polycarbonate polyol product is 2 or 3, and the hydroxyl value is 136-315 mgKOH/g.
The organic ligand structure of the metal organic compound catalyst synthesized by the invention is shown in figure 1. The molecular structure of a typical polycarbonate polyol product synthesized in accordance with the present invention is shown in FIG. 2.
The beneficial effects of the invention are as follows:
(1) The raw materials involved in the synthesis process are cheap and easy to obtain, the product has biodegradability, the synthesis process is simple, and industrial-scale production can be realized;
(2) The catalyst has short synthetic route, high catalytic efficiency, safety and no toxicity;
(3) The obtained product has higher carbon dioxide content, can realize chemical carbon fixation, can be directly used for synthesizing polyurethane foam, and can also be used in combination with other polyols.
Drawings
FIG. 1 is an organic ligand structure of a metal organic compound catalyst synthesized according to the present invention;
FIG. 2 is a molecular structure of a typical polycarbonate polyol product synthesized in accordance with the present invention.
Detailed Description
The invention is further described below in connection with specific embodiments.
Example 1
(1) A method for preparing a catalyst for synthesizing a carbon dioxide-based polycarbonate polyol product, comprising:
adding urea, 5-hydroxymethylfurfural, triethylamine and N, N-dimethylformamide into a high-pressure reaction kettle, heating, stirring and dissolving the urea and the 5-hydroxymethylfurfural to carry out chemical reaction; and (3) distilling under reduced pressure to remove water and triethylamine, and then adding zinc acetate and cobalt oxalate to obtain a catalyst system. Wherein, the mole ratio of urea, 5-hydroxymethyl furfural, triethylamine and N, N-dimethylformamide is 1:2:0.001:1, the mole ratio of urea, zinc acetate and cobalt oxalate is 1:2:1, a step of; the reaction temperature is 90 ℃ and the reaction time is 1h; the reduced pressure distillation temperature was 60℃and the reduced pressure distillation time was 2 hours.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing the catalyst and the solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator 1, 4-butanediol, propylene oxide and ethylene oxide is 0.001:2:1, the pressure of the system is 3.8Mpa after adding carbon dioxide, and the dosage of the catalyst is 0.1 percent of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 90 ℃ and the reaction time is 8 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; the pH of the product was adjusted to 7 with sodium hydroxide.
Example 2
(1) A catalyst for synthesizing a carbon dioxide based polycarbonate polyol product was prepared as in the examples.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing a catalyst and a solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator 1, 4-butanediol, propylene oxide and ethylene oxide is 0.001:2:1, the pressure of the system is 3.8Mpa after adding carbon dioxide, and the dosage of the catalyst is 0.5% of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 120 ℃, and the reaction time is 3 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; the pH of the product was adjusted to 7 with sodium hydroxide.
Example 3
(1) A catalyst for synthesizing a carbon dioxide based polycarbonate polyol product was prepared as in the examples.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing a catalyst and a solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator 1, 4-butanediol, propylene oxide and ethylene oxide is 0.001:2:0.1, the system pressure is 5.6Mpa after adding carbon dioxide, and the catalyst dosage is 0.2% of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 110 ℃, and the reaction time is 5 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; and adjusting the pH value of the product to 8 by adopting sodium hydroxide.
Example 4
(1) A catalyst for synthesizing a carbon dioxide based polycarbonate polyol product was prepared as in the examples.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing a catalyst and a solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator 1, 4-butanediol, propylene oxide and ethylene oxide is 0.001:2:0.1, the system pressure is 5.6Mpa after adding carbon dioxide, and the catalyst dosage is 0.4% of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 100 ℃, and the reaction time is 6 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; and adjusting the pH value of the product to 8 by adopting sodium hydroxide.
Example 5
(1) A catalyst for synthesizing a carbon dioxide based polycarbonate polyol product was prepared as in the examples.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing a catalyst and a solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator glycerin, propylene oxide and ethylene oxide is 0.001:2:1, the pressure of the system is 3.8Mpa after adding carbon dioxide, and the dosage of the catalyst is 0.1 percent of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 120 ℃, and the reaction time is 3 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; the pH of the product was adjusted to 7 with sodium hydroxide.
Example 6
(1) A catalyst for synthesizing a carbon dioxide based polycarbonate polyol product was prepared as in the examples.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing a catalyst and a solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator glycerin, propylene oxide and ethylene oxide is 0.001:2:1, the pressure of the system is 5.6Mpa after adding carbon dioxide, and the dosage of the catalyst is 0.2 percent of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 110 ℃, and the reaction time is 4 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; the pH of the product was adjusted to 7 with sodium hydroxide.
Example 7
(1) A catalyst for synthesizing a carbon dioxide based polycarbonate polyol product was prepared as in the examples.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing a catalyst and a solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator glycerin, propylene oxide and ethylene oxide is 0.001:2:0.1, the system pressure is 3.8Mpa after adding carbon dioxide, and the catalyst dosage is 0.4% of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 100 ℃, and the reaction time is 6 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; and adjusting the pH value of the product to 8 by adopting sodium hydroxide.
Example 8
(1) A catalyst for synthesizing a carbon dioxide based polycarbonate polyol product was prepared as in the examples.
(2) A method for preparing a carbon dioxide based polycarbonate polyol product:
adding nitrogen into a high-pressure reaction kettle containing a catalyst and a solvent to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, heating and stirring to perform chemical reaction; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product. The mole ratio of the initiator glycerin, propylene oxide and ethylene oxide is 0.001:2:0.1, the system pressure is 5.6Mpa after adding carbon dioxide, and the catalyst dosage is 0.5% of the total mass of the epoxypropane and the epoxyethane. The reaction temperature is 90 ℃ and the reaction time is 8 hours; the temperature of the reduced pressure distillation is 110 ℃ and the time is 2 hours; and adjusting the pH value of the product to 8 by adopting sodium hydroxide.
Example 9
Catalyst and carbon dioxide based polycarbonate polyol products were prepared as in example 1, except that: the reaction temperature in the preparation of the catalyst was 60℃and the reaction time was 3 hours.
Example 10
Catalyst and carbon dioxide based polycarbonate polyol products were prepared as in example 1, except that: the reaction temperature in the preparation of the catalyst was 80℃and the reaction time was 2 hours.
The polycarbonate polyol products synthesized in examples 1 to 10 were subjected to performance test, and the results are shown in Table 1. As shown in Table 1, the pH value of the product synthesized by the method provided by the invention can be kept stable within 7-8, the functionality, the hydroxyl value and the viscosity can be adjusted within a certain range, and the chemical fixation amount of the product to carbon dioxide is high. The polyurethane materials prepared by adopting the polycarbonate polyol products synthesized in examples 1-10 have good biodegradability (the degradation rate is determined by national standard GB/T38082-2019 by taking polyurethane synthesized by TDI as a black material as an example).
Table 1: properties of the polycarbonate polyol product obtained
The foregoing is only illustrative of the present invention and is not to be construed as limiting thereof, but rather, it is contemplated that various modifications, equivalent arrangements, improvements or the like may be made within the spirit and principles of the present invention.
Claims (8)
1. A method for preparing a carbon dioxide based polycarbonate polyol product, characterized by: the method comprises the following two steps:
(1) And (3) synthesizing a catalyst: adding urea, 5-hydroxymethylfurfural, triethylamine and N, N-dimethylformamide into a high-pressure reaction kettle according to a certain proportion, heating, stirring and dissolving the urea and the 5-hydroxymethylfurfural to react; removing water and triethylamine through reduced pressure distillation, and then adding zinc acetate and cobalt oxalate to obtain a catalyst system; the molar ratio of urea, 5-hydroxymethyl furfural, triethylamine and N, N-dimethylformamide is 1:2:0.001:1, the mole ratio of urea, zinc acetate and cobalt oxalate is 1:2:1, a step of;
(2) Synthesis of polycarbonate polyol: introducing nitrogen into the catalyst system to remove air in the reaction kettle, then dropwise adding an initiator, propylene oxide and ethylene oxide, adding carbon dioxide, and heating and stirring to react; and adding sodium hydroxide to regulate pH after the reaction is finished, filtering, and distilling under reduced pressure to remove small molecular byproducts, thus obtaining a colorless transparent polycarbonate polyol product.
2. A method of preparing a carbon dioxide based polycarbonate polyol product of claim 1, wherein: in the step (1), the reaction temperature of urea and 5-hydroxymethylfurfural is 60-90 ℃ and the reaction time is 1-3 h; the reduced pressure distillation temperature was 60℃and the reduced pressure distillation time was 2 hours.
3. A method of preparing a carbon dioxide based polycarbonate polyol product of claim 1, wherein: in the step (2), the initiator is 1, 4-butanediol or glycerol, and the molar ratio of the initiator to the propylene oxide to the ethylene oxide is 0.001:2: (1-0.1).
4. A method of preparing a carbon dioxide based polycarbonate polyol product of claim 1, wherein: in the step (2), the pressure of the system is 3.8-5.6 Mpa after adding carbon dioxide.
5. A method of preparing a carbon dioxide based polycarbonate polyol product of claim 1, wherein: in the step (2), the catalyst dosage is 0.1-0.5% of the total mass of the epoxypropane and the epoxyethane.
6. A method of preparing a carbon dioxide based polycarbonate polyol product of claim 1, wherein: in the step (2), the reaction temperature for synthesizing the polycarbonate polyol is 90-120 ℃ and the reaction time is 3-8 h.
7. A method of preparing a carbon dioxide based polycarbonate polyol product of claim 1, wherein: in the step (2), sodium hydroxide is adopted to adjust the pH value of the product to 7-8; the reduced pressure distillation temperature is 110 ℃ and the time is 2h.
8. A method of preparing a carbon dioxide based polycarbonate polyol product of claim 1, wherein: the functionality of hydroxyl groups in the polycarbonate polyol product is 2 or 3, and the hydroxyl value is 136-315 mgKOH/g.
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