CN110845715B - Method for preparing polyaryl ether polyol by using biomass - Google Patents
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Abstract
The invention relates to the technical field of polyether polyol, and provides a method for preparing polyaryl ether polyol by using biomass. The invention directly prepares the polyaryl ether polyol from the biomass, reduces the use of petroleum-based chemicals and simplifies the preparation steps; the use of toxic and harmful solvents or catalysts is avoided, the cost is reduced, and the environment is protected; the method adopts the organic solvent/water cosolvent to extract and separate the polyether polyol, has simple operation and is easy for large-scale preparation; furthermore, the preparation condition of the invention is mild, and the energy consumption is low; the advantages of the invention are beneficial to the simple and large-scale preparation of the polyether polyol, and further promote the development and utilization of the environment-friendly polyurethane foam material, and have practical significance.
Description
Technical Field
The invention relates to the technical field of polyether polyol, and particularly relates to a method for preparing polyaryl ether polyol by using biomass.
Background
Polyether polyol is an important raw material for preparing materials such as polyurethane and the like, and is mainly prepared from petrochemical chemicals through a series of complex processes in industry. Because the polyaryl ether polyol contains an aromatic structure, the formed polyurethane material has the characteristics of heat resistance, flame retardance and the like, and is one of important raw materials for preparing heat-resistant flame-retardant polyurethane foam materials.
Most of the existing preparation methods of the polyaryl ether polyol are obtained by petroleum-based chemicals through a complex preparation process; in recent years, with the enhancement of environmental awareness, the development of bio-based environment-friendly materials is concerned, and the development of the biomass-based polyaryl ether polyol has important significance for preparing environment-friendly degradable polyurethane materials. The existing research reports that the specific process for preparing the lignin-based polyether polyol can be divided into two parts: firstly, lignin is separated, then lignin is modified, and then polymerization reaction is carried out to obtain lignin-based polyether polyol; and secondly, separating lignin, liquefying the lignin into small molecules, and carrying out polymerization reaction to obtain the lignin-based polyether polyol. However, the above methods all have the disadvantages of complicated preparation process, complicated steps, high energy consumption, use of a large amount of toxic and harmful solvents and catalysts, and the like. At present, no report is related to the preparation of the polyaryl ether polyol directly from biomass by adopting an environment-friendly solvent.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for preparing a polyaryl ether polyol by using biomass. The method provided by the invention adopts the green environment-friendly solvent (eutectic solvent) to treat the biomass, directly prepares the polyether glycol from the biomass, adopts the organic solvent/water cosolvent to directly separate the polyether glycol from the mixture treated by the eutectic solvent, and has the advantages of simple and easy operation, strong environmental protection and low energy consumption.
In order to achieve the above object, the present invention provides the following technical solutions:
a method of using biomass to produce a polyaryl ether polyol comprising the steps of:
(1) mixing a biomass raw material and a eutectic solvent for heat treatment to obtain a heat treatment material; the eutectic solvent consists of choline chloride, oxalic acid and ethylene glycol;
(2) mixing the heat-treated material with ethanol to remove impurities, and then removing the ethanol to obtain a mixture of a eutectic solvent and the polyaryl ether polyol;
(3) and (3) extracting and separating the mixture of the eutectic solvent and the polyaryl ether polyol by using an organic solvent/water cosolvent to obtain the polyaryl ether polyol.
Preferably, the biomass raw material is a hardwood and/or coniferous tree.
Preferably, the mass ratio of the biomass raw material to the eutectic solvent is (0.5-3) to (30-50).
Preferably, the mol ratio of the choline chloride to the oxalic acid to the ethylene glycol is 120 (2.4-24) to 240 or 120:120 (40-360).
Preferably, when the mol ratio of the choline chloride to the oxalic acid to the ethylene glycol is 120 (2.4-24) to 240, the temperature of the heat treatment is 80-100 ℃, and the time is 6-24 hours; when the mol ratio of choline chloride to oxalic acid to glycol is 120:120 (40-360), the temperature of the heat treatment is 100-140 ℃, and the time is 10-60 min.
Preferably, the impurity removal is filtration impurity removal.
Preferably, the organic solvent of the organic solvent/water co-solvent comprises tetrahydrofuran and/or methyltetrahydrofuran.
Preferably, the volume ratio of the organic solvent to the water in the organic solvent/water cosolvent is (0.8-2.5): 1.
Preferably, the water phase obtained after the extraction separation is subjected to reduced pressure distillation to recover the eutectic solvent.
The invention provides a method for preparing polyether polyol by using biomass. The invention directly prepares the polyaryl ether polyol from the biomass, reduces the use of petroleum-based chemicals and simplifies the preparation steps; the use of the green and nontoxic eutectic solvent avoids the use of toxic and harmful solvents or catalysts, reduces the cost and has little influence on the environment; the method adopts the organic solvent/water cosolvent to extract and separate the polyether polyol, has simple operation and is easy for large-scale preparation; furthermore, the preparation condition is mild, the heat treatment temperature is low, and the energy consumption is low; the advantages of the invention are beneficial to the simple and large-scale preparation of the polyether polyol, and further promote the development and utilization of the environment-friendly polyurethane foam material, and have practical significance.
Drawings
FIG. 1 is a schematic flow diagram of the preparation of a polyarylate polyether polyol using biomass in an embodiment of the present invention;
FIG. 2 is a schematic flow chart of the preparation of a polyarylate polyether polyol by using a biomass in the embodiment of the present invention;
FIG. 3 is a two-dimensional HSQC spectrum of the polyarylether polyol prepared in example 1;
FIG. 4 is a two-dimensional HSQC spectrum of the polyarylether polyol prepared in example 2;
FIG. 5 is a two-dimensional HSQC spectrum of the polyarylate polyether polyol prepared in example 5.
Detailed Description
The invention provides a method for preparing polyaryl ether polyol by using biomass, which comprises the following steps:
(1) mixing a biomass raw material and a eutectic solvent for heat treatment to obtain a heat treatment material; the eutectic solvent consists of choline chloride, oxalic acid and ethylene glycol;
(2) mixing the heat-treated material with ethanol to remove impurities, and then removing the ethanol to obtain a mixture of a eutectic solvent and the polyaryl ether polyol;
(3) and (3) extracting and separating the mixture of the eutectic solvent and the polyaryl ether polyol by using an organic solvent/water cosolvent to obtain the polyaryl ether polyol.
According to the invention, the biomass raw material and the eutectic solvent are mixed for heat treatment to obtain a heat treatment material. In the present invention, the biomass feedstock is preferably a hardwood and/or coniferous tree; the broadleaf wood is particularly preferably poplar or birch; the coniferous trees are preferably Chinese fir; the biomass material is preferably used in the form of powder, such as poplar wood powder, birch wood powder or cedar wood powder.
In the present invention, the eutectic solvent consists of choline chloride, oxalic acid and ethylene glycol; the oxalic acid is preferably oxalic acid hydrate; the choline chloride, the oxalic acid and the ethylene glycol are all from natural products, are green, non-toxic and degradable, and the deep-eutectic solvent is used for treating biomass raw materials, so that the deep-eutectic solvent is strong in environmental protection and has small influence on the environment; in the invention, the mol ratio of choline chloride, oxalic acid and glycol is 120 (2.4-24) to 240 or 120:120 (40-360), more preferably 120 (5-20) to 240 or 120:120 (50-300); when the mol ratio of choline chloride to oxalic acid to ethylene glycol is 120 (2.4-24) to 240, the heat treatment temperature is preferably 80-100 ℃, more preferably 85-95 ℃, and the time is preferably 6-24 hours, more preferably 8-22 hours; when the mol ratio of choline chloride to oxalic acid to ethylene glycol is 120:120 (40-360), the heat treatment temperature is preferably 100-140 ℃, more preferably 110-130 ℃, and the time is preferably 10-60 min, more preferably 20-50 min; in the invention, the mass ratio of the biomass raw material to the eutectic solvent is preferably (0.5-3): 30-50, and more preferably (1-2): 35-45.
The biomass raw material has an anti-depolymerization barrier formed by lignin and hemicellulose, the eutectic solvent can well dissolve the lignin due to the action of internal strong hydrogen bonds, and during the heat treatment process, the lignin component in the biomass raw material is dissolved in the eutectic solvent and is etherified with glycol to form the polyaryl ether polyol; the oxalic acid can destroy the structure of the biomass raw material (namely destroy the anti-depolymerization barrier), promote the dissolution of lignin, promote the etherification of glycol and lignin and further promote the formation of the polyaryl ether polyol; in addition, in the eutectic solvent, choline chloride is used as a hydrogen bond receptor, has the effects of removing an anti-depolymerization barrier, weakening the action force of the hydrogen bond and promoting the dissolution of lignin in cooperation with oxalic acid, and the separated components can form the hydrogen bond action with the choline chloride to promote the dissolution.
After the heat treatment is finished, the heat treatment material and ethanol are mixed for impurity removal, and then the ethanol is removed to obtain a mixture of the eutectic solvent and the polyaryl ether polyol. The impurity removal is preferably filtration impurity removal, namely, the heat treatment material is mixed with ethanol and then filtered; the ethanol can dissolve the eutectic solvent and the polyaryl ether polyol, and residual residues of the biomass raw material can be removed through filtering; the filtrate obtained after filtration is a mixture of the eutectic solvent, ethanol and the polyaryl ether polyol, and the ethanol in the filtrate is removed by reduced pressure distillation in the invention to obtain the mixture of the eutectic solvent and the polyaryl ether polyol.
After the mixture of the eutectic solvent and the polyaryl ether polyol is obtained, the mixture of the eutectic solvent and the polyaryl ether polyol is extracted and separated by using an organic solvent/water cosolvent to obtain the polyaryl ether polyol. In the present invention, the organic solvent of the organic solvent/water co-solvent preferably comprises tetrahydrofuran and/or methyltetrahydrofuran; the volume ratio of the organic solvent to the water in the organic solvent/water cosolvent is preferably (0.8-2.5) to 1, and more preferably 1-2: 1; in the present invention, the ratio of the amount of the organic solvent/water co-solvent to the mixture of the eutectic solvent and the polyarylate ether polyol is preferably 100: 36 to 39 (mL: g); in the present invention, it is preferred to extract three times and combine the organic phases. The polyaryl ether polyol has stronger hydrophilicity, and the organic solvent/water cosolvent is added into the system, and the eutectic solvent is dissolved in water, so that the ion concentration in the water phase is increased, the solubility of the polyaryl ether polyol in the water is greatly reduced, and the polyaryl ether polyol is further dissolved in the organic solvent phase to achieve the purpose of separation; the method for extracting and separating the polyaryl ether polyol by using the organic solvent/water cosolvent has the advantages of simple and easy operation and good separation effect, can achieve the purpose of extraction only by adding a small amount of water, and is convenient for the recovery of the subsequent eutectic solvent.
In the invention, the organic phase obtained after extraction is preferably subjected to reduced pressure distillation to remove the organic solvent, and the remainder is washed with saturated salt solution and then dried to obtain the polyaryl ether polyol.
In the invention, the water phase obtained after extraction and separation is preferably distilled under reduced pressure to remove water in the water phase so as to recover the eutectic solvent.
The embodiments of the present invention will be described in detail with reference to the following examples, but they should not be construed as limiting the scope of the present invention.
FIG. 1 is a schematic flow diagram of the preparation of a polyarylate polyether polyol using biomass in an embodiment of the present invention;
FIG. 2 is a flow chart of the preparation of the polyarylate ether polyol by using the biomass in the embodiment of the present invention.
Example 1
Adding 2g of poplar wood powder into about 34g of eutectic solvent (120mmol of choline chloride, 240mmol of ethylene glycol and 24mmol of oxalic acid hydrate), heating and stirring at 100 ℃ for 24 hours, adding 100mL of ethanol after reaction to dissolve the mixture, and filtering and separating to obtain the mixture of the eutectic solvent and the polyaryl ether polyol; after ethanol is removed by reduced pressure distillation, the polyaryl ether polyol is subjected to liquid/liquid extraction by tetrahydrofuran/water (50mL/50mL) for three times, a tetrahydrofuran organic layer containing the polyaryl ether polyol is separated, concentrated by reduced pressure distillation and washed by saturated salt solution, and dried in a dryer to obtain the polyaryl ether polyol.
Example 2
Adding 2g of Chinese fir wood powder into about 34g of eutectic solvent (120mmol of choline chloride, 240mmol of ethylene glycol and 24mmol of oxalic acid hydrate), heating and stirring at 100 ℃ for 24h, adding 100mL of ethanol after reaction to dissolve the mixture, and filtering and separating to obtain a mixture of ethanol, the eutectic solvent and the polyaryl ether polyol; and after ethanol is removed by reduced pressure distillation, liquid/liquid extraction is carried out on the mixture of the eutectic solvent and the polyether glycol by tetrahydrofuran/water (50mL/50mL) for three times, the tetrahydrofuran organic layer containing the polyether glycol is separated, and then the mixture is concentrated by reduced pressure distillation and washed by saturated salt solution, and is dried in a dryer to obtain the polyether glycol.
Example 3
Adding 2g of birch wood powder into about 34g of eutectic solvent (120mmol of choline chloride, 240mmol of ethylene glycol and 24mmol of oxalic acid hydrate), heating and stirring for 24h at 100 ℃, adding 100mL of ethanol after reaction to dissolve the mixture, and filtering and separating to obtain a mixture of ethanol, the eutectic solvent and the polyaryl ether polyol; after ethanol was removed by distillation under reduced pressure, the mixture of the eutectic solvent and the polyarylate ether polyol was subjected to liquid/liquid extraction with tetrahydrofuran/water (50mL/50mL), which was repeated three times, and after the separation of the tetrahydrofuran organic layer containing polyarylate ether polyol, the mixture was concentrated by distillation under reduced pressure and washed with saturated brine, and dried in a dryer to obtain polyarylate ether polyol.
Example 4
Adding 2g of birch wood powder into about 37g of eutectic solvent (120mmol of choline chloride, 240mmol of ethylene glycol and 48mmol of oxalic acid hydrate), heating and stirring at 100 ℃ for 24h, adding 100mL of ethanol after reaction to dissolve the mixture, and filtering and separating to obtain a mixture of ethanol, the eutectic solvent and the polyaryl ether polyol; after ethanol was removed by distillation under reduced pressure, the mixture of the eutectic solvent and the polyarylate ether polyol was subjected to liquid/liquid extraction with tetrahydrofuran/water (50mL/50mL), which was repeated three times, and after the separation of the tetrahydrofuran organic layer containing polyarylate ether polyol, the mixture was concentrated by distillation under reduced pressure and washed with saturated brine, and dried in a dryer to obtain polyarylate ether polyol.
Example 5
Adding 2g of birch wood powder into about 46g of eutectic solvent (120mmol of choline chloride, 240mmol of ethylene glycol and 120mmol of oxalic acid hydrate), heating and stirring at 120 ℃ for 30min, adding 100mL of ethanol after reaction to dissolve the mixture, and filtering and separating to obtain a mixture of ethanol, the eutectic solvent and the polyaryl ether polyol; after ethanol was removed by distillation under reduced pressure, the mixture of the eutectic solvent and the polyarylate ether polyol was subjected to liquid/liquid extraction with tetrahydrofuran/water (50mL/50mL), which was repeated three times, and after the separation of the tetrahydrofuran organic layer containing polyarylate ether polyol, the mixture was concentrated by distillation under reduced pressure and washed with saturated brine, and dried in a dryer to obtain polyarylate ether polyol.
Calculating the yield of the polyaryl ether polyol in the examples 1-5; characterizing the structure of the polyether polyol obtained in the examples 1-5 by two-dimensional HSQC nuclear magnetism, and calculating the content of aryl ether bonds; the results obtained are shown in table 1, in which: the isolated yield is the mass of the polyarylate polyether polyol/lignin in the wood flour x 100%.
TABLE 1 polyaryl ether polyol yield and structural analysis
As can be seen from the data in table 1, the polyaryl ether polyol yield: the polyaryl ether polyol yields of examples 1 through 5 were 45%, 44%, 29%, 83%, and 48%, respectively, with the polyaryl ether polyol yield of example 4 being the highest. The polyarylether polyols obtained in examples 1 to 5 all have a high content ranging from 59 to 66 per 100 aromatic units.
FIG. 3 is a two-dimensional HSQC spectrum of the polyarylate polyether polyol (poplar polyarylate polyether polyol) prepared in example 1, wherein β -O-4 and β -O-4' represent signals associated with the polyarylate polyether polyol. As can be derived from FIG. 3, the main basic units constituting the polyarylate ether polyol are guaiacyl and syringyl basic units; the main structures of the polyaryl ether polyols are beta-O-4 (the original polyaryl ether polyol structure of poplar), beta-O-4 '(the polyaryl ether polyol structure derived), beta-beta' and beta-5, the contents of which are respectively 15, 48, 5 and 4 per 100 aromatic units. Wherein beta-O-4' is the main polyaryl ether polyol structure, which indicates that the obtained separation product is polyaryl ether polyol, and the polyaryl ether polyol is obtained by glycolation according to the structure; the total polyaryl ether polyol content was 63 per 100 aromatic units.
FIG. 4 is a two-dimensional HSQC spectrum of the polyarylether polyol (fir-based polyarylate polyether polyol) prepared in example 2, wherein β -O-4 and β -O-4' represent signals associated with polyarylate polyether polyol. As can be seen from FIG. 4, the main basic unit constituting the polyarylate ether polyol is a guaiacyl basic unit; the main structures of the polyaryl ether polyols are beta-O-4 (the original polyaryl ether polyol structure of cedar), beta-O-4 '(the polyaryl ether polyol structure derived), beta-beta' and beta-5, the contents of which are 8, 57, 3 and 23 per 100 aromatic units, respectively. Wherein beta-O-4' is the main polyaryl ether polyol structure, which indicates that the obtained separation product is polyaryl ether polyol, and the polyaryl ether polyol is obtained by glycolation according to the structure; the total polyaryl ether polyol content was 65 per 100 aromatic units.
FIG. 5 is a two-dimensional HSQC spectrum of the polyarylate polyether polyol (birch-based polyarylate polyether polyol) prepared in example 5. As can be seen from FIG. 5, the main basic units constituting the polyarylate ether polyol are guaiacyl and syringyl basic units; the main structures of the polyaryl ether polyols are beta-O-4 (the original polyaryl ether polyol structure of birch), beta-O-4 '(the polyaryl ether polyol structure derived), beta-beta' and beta-5, the contents of which are 19, 47, 13 and 3, respectively, per 100 aromatic units. Wherein beta-O-4' is the main polyaryl ether polyol structure, which indicates that the obtained separation product is polyaryl ether polyol, and the polyaryl ether polyol is obtained by glycolation according to the structure; the total polyaryl ether polyol content is 66 per 100 aromatic units.
As can be seen from the above examples, the invention adopts the green and environment-friendly eutectic solvent system, and the polyarylate polyether polyol is directly prepared from biomass raw materials widely existing in the nature, the preparation conditions are mild, and the steps are simple; the method adopts the organic solvent/water cosolvent to directly separate the polyether polyol from the mixture treated by the eutectic solvent, and has simple and easy operation; the method provided by the invention is beneficial to the simple and large-scale preparation of the polyaryl ether polyol, further promotes the development and utilization of the environment-friendly polyurethane foam material, and has practical significance.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (7)
1. A method for preparing polyaryl ether polyol by using biomass is characterized by comprising the following steps:
mixing a biomass raw material and a eutectic solvent for heat treatment to obtain a heat treatment material; the eutectic solvent consists of choline chloride, oxalic acid and ethylene glycol;
mixing the heat-treated material with ethanol to remove impurities, and then removing the ethanol to obtain a mixture of a eutectic solvent and the polyaryl ether polyol;
extracting and separating the mixture of the eutectic solvent and the polyaryl ether polyol by using an organic solvent/water cosolvent to obtain polyaryl ether polyol;
the mol ratio of the choline chloride to the oxalic acid to the ethylene glycol is 120 (2.4-24) to 240 or 120:120 (40-360); when the mol ratio of choline chloride to oxalic acid to glycol is 120, (2.4-24) to 240, the temperature of the heat treatment is 80-100 ℃, and the time is 6-24 hours; when the mol ratio of choline chloride to oxalic acid to glycol is 120:120 (40-360), the temperature of the heat treatment is 100-140 ℃, and the time is 10-60 min.
2. The method of claim 1, wherein the biomass feedstock is hardwood and/or softwood.
3. The method according to claim 1 or 2, wherein the mass ratio of the biomass raw material to the eutectic solvent is (0.5-3) to (30-50).
4. The method of claim 1, wherein the contaminant removal is filtration contaminant removal.
5. The method of claim 1, wherein the organic solvent of the organic solvent/water co-solvent comprises tetrahydrofuran and/or methyltetrahydrofuran.
6. The method according to claim 1 or 5, wherein the volume ratio of the organic solvent to the water in the organic solvent/water cosolvent is (0.8-2.5): 1.
7. The method according to claim 1, characterized in that the aqueous phase obtained after the extractive separation is subjected to reduced pressure distillation to recover the eutectic solvent.
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| CN104887723A (en) * | 2015-06-18 | 2015-09-09 | 天津理工大学 | Method for extracting flavonoids from ginkgo biloba leaves with deep eutectic solvent |
| CN105037062A (en) * | 2015-06-18 | 2015-11-11 | 天津理工大学 | Alcohol-based ternary deep-eutectic solvent and preparation method thereof |
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