CN110590707B - Polyethylene oxide containing N-acetylmorpholinyl functional group and preparation method thereof - Google Patents
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
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- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
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Abstract
A polyethylene oxide containing N-acetyl morpholinyl functional groups and a preparation method thereof, belonging to the technical field of high polymer materials. One end of the molecular structure of the polyethylene oxide is an N-acetylmorpholinyl functional group, and the polymerization degree is 3-75. The preparation method comprises the following steps: under alkaline conditions, the ring-opening polymerization of ethylene oxide is carried out, and the ethylene oxide reacts with a hydroxyl morpholine ketone compound to obtain polyethylene oxide which contains a hydroxyl functional group and contains an N-acetyl morpholine functional group; or adding the polyethylene oxide containing the N-acetylmorpholinyl functional group with one end of a hydroxyl functional group, a catalyst DMAP, and acid anhydride or acid containing an allyl bond into a solvent to perform esterification reaction to obtain the polyethylene oxide containing the N-acetylmorpholinyl functional group with one end of an allyl functional group. The invention has the beneficial effects that: the polyethylene oxide provided has excellent aromatic hydrocarbon adsorption selectivity polarity, and the toluene/n-heptane adsorption selectivity coefficient is not less than 20, so that the polyethylene oxide has a very good application prospect in the field of aromatic hydrocarbon/alkane separation.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and relates to polyethylene oxide and a preparation method thereof, wherein the polyethylene oxide refers to polyethylene oxide containing N-acetylmorpholinyl functional groups, has excellent aromatic hydrocarbon adsorption selectivity, and has a good application prospect in the field of aromatic hydrocarbon/alkane separation.
Background
The separation of aromatic hydrocarbon/alkane mixture is the main production way of benzene, toluene and xylene (BTX) as basic chemical raw materials, and has an extremely important position in the field of petrochemical industry. The traditional aromatic hydrocarbon/alkane separation technology, such as azeotropic distillation, extractive distillation, liquid-liquid extraction and the like, generally has the defects of complex flow, high cost, large energy consumption and the like, and needs an alternative technology urgently. Pervaporation is an environment-friendly novel membrane separation technology, and the components in a liquid mixture are separated by utilizing the difference of the solubility and diffusivity in a separation membrane. Because the method is not limited by vapor-liquid equilibrium relationship, the pervaporation can realize the high-efficiency separation of the mixture with similar component boiling points and the azeotrope, and has potential application value in the aspect of aromatic hydrocarbon/alkane separation. The polymer containing ethylene oxide repeating units is a membrane material for preparing an aromatic hydrocarbon/alkane separation membrane. The literature [ Journal of Membrane Science,2004,234(1-2):55-65] discloses the preparation of aromatic hydrocarbon/alkane separation membranes using polyethylene oxide macromolecules containing hydroxyl end groups or methyl ether end groups, respectively.
It is well known that increasing the separation coefficient of a membrane can reduce the membrane area required to accomplish a particular separation task, thereby increasing the economics of the process. For the aromatic hydrocarbon/alkane separation membrane technology, the development of a polymer membrane material with a higher separation coefficient is an effective way for improving the competitiveness of the aromatic hydrocarbon/alkane separation membrane technology.
Disclosure of Invention
The invention provides the polyethylene oxide containing the N-acetylmorpholinyl functional group and the preparation method thereof, and the polyethylene oxide containing the N-acetylmorpholinyl functional group has excellent aromatic hydrocarbon adsorption selectivity and better application prospect in the field of aromatic hydrocarbon/alkane separation.
In order to achieve the purpose, the invention adopts the technical scheme that:
the polyethylene oxide containing the N-acetylmorpholinyl functional group has a molecular structure with one end of the N-acetylmorpholinyl functional group, and the polymerization degree of the ethylene oxide of the polyethylene oxide is 3-75, preferably 5-11. The structural formula of the N-acetylmorpholinyl functional group is shown as follows:
wherein R is1、R2、R3、R4At least one of H, alkyl with 1-10 carbon atoms, phenyl and substituted phenyl; r1、R2、R3、R4The same or different groups may be independently selected.
The homogeneous membrane prepared from the polyethylene oxide containing the N-acetylmorpholinyl functional group has excellent aromatic hydrocarbon/alkane separation performance, and the toluene/N-heptane adsorption selectivity coefficient is not less than 20.
The preparation method of the polyethylene oxide containing the N-acetylmorpholinyl functional group comprises the steps of respectively preparing the N-acetylmorpholinyl functional group and the hydroxyl functional group at two ends of the polyethylene oxide, carrying out ring-opening polymerization on the polyethylene oxide under the alkaline condition, and reacting the polyethylene oxide with a hydroxymorpholone compound to obtain the polyethylene oxide containing the N-acetylmorpholinyl functional group, wherein one end of the polyethylene oxide is the hydroxyl functional group; the method comprises the following steps:
under the protection of nitrogen at room temperature, adding a solvent, a catalyst and a hydroxyl morpholone compound into a reaction container, wherein the concentration of the hydroxyl morpholone compound is 0.10-0.15 g/ml, and the molar ratio of the catalyst to the hydroxyl morpholone compound is 0.05-1; adding ethylene oxide, wherein the dosage of the ethylene oxide is determined according to the polymerization degree of the ethylene oxide; under the alkaline condition, the epoxy ethane is subjected to ring-opening polymerization, the reaction temperature is 90-150 ℃, and the reaction time is 4-24 h; and cooling to room temperature after reaction, and removing the solvent by rotary evaporation to obtain a product, namely the polyethylene oxide containing the N-acetylmorpholinyl functional group with one end being a hydroxyl functional group.
The solvent is selected from tetrahydrofuran, dimethyl sulfoxide or dimethylformamide.
The catalyst is selected from KOH or NaH.
The structural formula of the hydroxyl morpholone compound is shown as follows:
wherein n is 1 to 5, preferably 1 to 2. R1、R2、R3、R4At least one of H, alkyl with 1-10 carbon atoms, phenyl and substituted phenyl; r1、R2、R3、R4The same or different groups may be independently selected. Preferably, the hydroxymorpholinone compounds include, but are not limited to, 2-hydroxy-1- (4-morpholine) ethanone, 2-hydroxy-1- (5-methyl-2- (o-tolyl) morpholine) ethanone, and 3-hydroxy-1- (4-morpholine) -1-propanone.
The preparation method of the polyethylene oxide containing the N-acetylmorpholinyl functional group comprises the steps of respectively preparing the N-acetylmorpholinyl functional group and the allyl functional group at two ends of the polyethylene oxide, carrying out ring-opening polymerization on the polyethylene oxide under the alkaline condition, and reacting the polyethylene oxide with a hydroxymorpholone compound to obtain the polyethylene oxide containing the N-acetylmorpholinyl functional group, wherein one end of the polyethylene oxide is the hydroxyl functional group; then, an acid anhydride or acid containing an allyl bond is added to perform an esterification reaction, thereby obtaining the polyethylene oxide containing an N-acetylmorpholinyl functional group with one end being an allyl functional group. The method comprises the following steps:
firstly, under the protection of nitrogen at room temperature, adding a solvent, a catalyst and a hydroxyl morpholone compound into a reaction container, wherein the concentration of the hydroxyl morpholone compound is 0.10-0.15 g/ml, and the molar ratio of the catalyst to the hydroxyl morpholone compound is 0.05-1; adding ethylene oxide, wherein the dosage of the ethylene oxide is determined according to the polymerization degree of the ethylene oxide; under the alkaline condition, the epoxy ethane is subjected to ring-opening polymerization, the reaction temperature is 90-150 ℃, and the reaction time is 4-24 h; and cooling to room temperature after reaction, and removing the solvent by rotary evaporation to obtain a product I, namely the polyethylene oxide containing the N-acetylmorpholinyl functional group and one end of which is a hydroxyl functional group.
The solvent is selected from tetrahydrofuran, dimethyl sulfoxide or dimethylformamide.
The catalyst is selected from KOH or NaH.
The structural formula of the hydroxyl morpholone compound is shown as follows:
wherein n is 1 to 5, preferably 1 to 2. R1、R2、R3、R4At least one of H, alkyl with 1-10 carbon atoms, phenyl and substituted phenyl; r1、R2、R3、R4The same or different groups may be independently selected. Preferably, the hydroxymorpholinone compounds include, but are not limited to, 2-hydroxy-1- (4-morpholine) ethanone, 2-hydroxy-1- (5-methyl-2- (o-tolyl) morpholine) ethanone, and 3-hydroxy-1- (4-morpholine) -1-propanone.
Secondly, adding the product I, a catalyst 4-Dimethylaminopyridine (DMAP) and an anhydride or acid containing an allyl bond into a solvent, wherein the mass ratio of the anhydride or acid containing the allyl bond to the product I is 0.2-0.5, the molar ratio of the catalyst to the anhydride or acid containing the allyl bond is 0.005-0.008, and the concentration of the anhydride or acid containing the allyl bond is 0.04-0.06 g/ml; esterification reaction is carried out, the reaction temperature is 40-70 ℃, and the reaction time is 8-16 h; after the reaction, cooling to room temperature, adding an aqueous solution of sodium bicarbonate, shaking, standing, taking an organic layer, and removing the solvent by rotary evaporation to obtain a product II, namely the polyethylene oxide containing the N-acetylmorpholinyl functional group, one end of which is the allyl functional group.
The acid anhydride containing allyl bond comprises methacrylic anhydride and acrylic anhydride, and the acid containing allyl bond comprises methacrylic acid and acrylic acid.
The invention has the beneficial effects that: provides polyethylene oxide containing N-acetyl morpholinyl functional group and a preparation method thereof. The polyethylene oxide containing the N-acetylmorpholinyl functional group has excellent aromatic hydrocarbon adsorption selectivity polarity and has very good application prospect in the field of aromatic hydrocarbon/alkane separation.
Drawings
FIG. 1 shows the MALDI-TOF mass spectrum of product II.
FIG. 2 is C10H15NO4High resolution ofMass spectrum.
Detailed Description
The following examples are presented to further illustrate the present invention, but are not intended to limit the scope of the invention as claimed.
Example 1
By adopting the synthetic route 1, 15ml of tetrahydrofuran solvent, 1.45g (0.01mol) of 2-hydroxy-1- (4-morpholine) ethanone and 0.2244g (0.004mol) of KOH are added into a reaction kettle under the protection of nitrogen. Pressurizing the nitrogen of the system to 0.5MPa, adding 5ml of ethylene oxide into the reaction kettle, reacting for 6 hours, cooling to room temperature, and removing the solvent by rotary evaporation to finally obtain 7.12g of a product (I), namely the polyethylene oxide containing the N-acetylmorpholinyl functional group, wherein one end of the product is a hydroxyl functional group.
Synthesis scheme 1
Using Synthesis scheme 2, 6.52g of product (I), 3.01g (0.02mol) of methacrylic anhydride, 0.0125g (0.0001mol) of 4-Dimethylaminopyridine (DMAP) were added to 50ml of a chloroform solvent and reacted at 60 ℃ under reflux for 12 hours. Adding sodium bicarbonate aqueous solution, shaking, standing, taking an organic layer, and removing the solvent by rotary evaporation to obtain 5.33g of a product (II), namely the polyethylene oxide containing the N-acetylmorpholinyl functional group, wherein one end of the product is an allyl functional group.
FIG. 1 is a MALDI-TOF mass spectrum of product (II) obtained in example 1. In FIG. 1, [ M + Na ] with M/z of 368.3, 412.3, 456.6, 500.4, 544.4, 588.5, 632.5, 676.5, 720.6, 764.6, 808.6 and 852.7]+The peaks respectively correspond to products (II) with different polymerization degrees of ethylene oxide, namely the products (II) are polyethylene oxide homologues with polymerization degrees of 3-14 and containing N-acetylmorpholinyl functional groups, and the polymerization degrees are mainly 5-11.
Preparing the product (II) into an aqueous solution with the mass fraction of 5%, adding potassium persulfate with the mass fraction of 10% of the monomer as an initiator, and carrying out reflux reaction for 3h at 70 ℃. After the reaction is finished, spin-steaming to remove water to obtain a homopolymer solution of the product (II), and preparing a homogeneous membrane by a solvent volatilization method. The aromatic hydrocarbon/alkane adsorption selectivity of the homopolymer characterizing the product (II) was analyzed using a conventional adsorption swelling adsorption experiment. Using toluene/n-heptane as model aromatic hydrocarbon/alkane mixture, soaking the homogeneous membrane in 20 wt% toluene/n-heptane material solution at 80 deg.C for 48 hr to reach adsorption swelling balance, analyzing the composition of toluene/n-heptane solution dissolved and adsorbed in the homogeneous membrane, and calculating adsorption selectivity coefficient alpha according to formula (1)S。
In the formula, ytolAnd yhepThe mass contents, x, of toluene and n-heptane adsorbed in the homogeneous membrane, respectivelytolAnd xhepRespectively the mass contents of toluene and n-heptane in the raw material liquid.
toluene/N-heptane adsorptive selectivity coefficient α at 80 ℃ for a homopolymer of polyethylene oxide containing N-acetylmorpholinyl functional groups, product (II)SIs 21.
Example 2
Synthesis scheme 1 was used, and 10ml of dimethyl sulfoxide (DMSO) solvent, 1.45g (0.01mol) of 2-hydroxy-1- (4-morpholine) ethanone, and 0.0281g (0.0005mol) of KOH were added to a reaction vessel under nitrogen protection. The nitrogen in the system is pressurized to 0.5MPa, and 5ml of ethylene oxide is added into the reaction kettle for reaction for 9 hours at 120 ℃. After the solution was cooled to room temperature, the solvent was removed by rotary evaporation to obtain 8.37g of the product (I), i.e., an N-acetylmorpholino functional group-containing polyethylene oxide having a hydroxyl functional group at one end.
Using Synthesis scheme 2, 8.20g of product (I), 2.00g (0.013mol) of methacrylic anhydride, and 0.0125g (0.0001mol) of DMAP were added to 50ml of a chloroform solvent, and the mixture was refluxed at 40 ℃ for 16 hours. Adding sodium bicarbonate aqueous solution, shaking, standing, taking an organic layer, and removing the solvent by rotary evaporation to obtain 7.81g of a product (II), namely the polyethylene oxide containing the N-acetylmorpholinyl functional group, wherein one end of the product is an allyl functional group. Using the same procedure as in example 1, potassium persulfate was used as an initiator to obtain a homopolymer of the product (II) which was subjected to radical polymerization and subjected to adsorption swelling test to give a toluene/n-heptane adsorption selectivity coefficient of 21 at 80 ℃.
Example 3
Using the same synthetic route and analytical test method as in example 1, the amount of ethylene oxide added was increased only to 25ml to give the product (I). The product (I) is further reacted with methacrylic anhydride to give the product (II). The product (II) is a homologue of ethylene oxide with a degree of polymerization of 12 to 75 respectively, and the homopolymer thereof has a toluene/n-heptane adsorption selectivity coefficient of 20 at 80 ℃.
Example 4
By adopting a synthetic route 1, 25ml of N, N-dimethylformamide solvent, 2.93g (0.02mol) of 2-hydroxy-1- (4-morpholine) ethanone and 0.4792g (0.02mol) of NaH are added into a reaction kettle under the protection of nitrogen. Pressurizing the nitrogen of the system to 0.5MPa and 140 ℃, adding 10ml of ethylene oxide into the reaction kettle, cooling to room temperature after 5 hours of reaction, and removing the solvent by rotary evaporation to finally obtain 13.62g of a product (I), namely the polyethylene oxide containing the N-acetylmorpholinyl functional group, one end of which is a hydroxyl functional group.
Using Synthesis scheme 2, 13.62g of product (I), 4.62g (0.03mol) of methacrylic anhydride, and 0.0251g (0.0002mol) of DMAP were added to 100ml of a chloroform solvent, and the reaction was refluxed at 70 ℃ for 8 hours. Adding sodium bicarbonate aqueous solution, shaking, standing, taking an organic layer, and removing the solvent by rotary evaporation to obtain 10.81g of a product (II), namely the polyethylene oxide containing the N-acetylmorpholinyl functional group and one end of which is allyl. Using the same procedure as in example 1, potassium persulfate was used as an initiator to obtain a homopolymer of the product (II) which was subjected to radical polymerization and subjected to adsorption swelling test to give a toluene/n-heptane adsorption selectivity coefficient of 21 at 80 ℃.
Example 5
The same synthetic route and analytical test method as in example 1 were used, and the reaction temperature was set to 150 ℃ and the reaction time was set to 4 hours for only the synthesized product (I). The product (II) homopolymer obtained had a toluene/n-heptane adsorption selectivity factor of 22 at 80 ℃.
Example 6
The same synthetic route and analytical test method as in example 1 were used, and the reaction temperature was set to 90 ℃ and the reaction time was set to 24 hours for only the synthesized product (I). The product (II) homopolymer obtained had a toluene/n-heptane adsorptive selectivity factor of 21 at 80 ℃.
Example 7
According to synthetic route 1 and synthetic route 2, using the same experimental conditions and analytical test methods as in example 1, only methacrylic anhydride was replaced with the same number of moles of acrylic anhydride to obtain a product having a molecular structure as shown in the following figure, and the homopolymer thereof had a toluene/n-heptane adsorption selectivity coefficient of 21 at 80 ℃.
Molecular Structure of the product of example 7
Example 8
According to synthetic route 1 and synthetic route 2, using the same experimental conditions and analytical test methods as in example 1, only 2-hydroxy-1- (4-morpholine) ethanone was replaced with the same number of moles of 2-hydroxy-1- (5-methyl-2- (o-tolyl) morpholine) ethanone to give a product having a molecular structure as shown in the following figure, whose homopolymer has a toluene/n-heptane adsorption selectivity coefficient at 80 ℃ of 23.
Molecular Structure of the product of example 8
Example 9
According to synthetic route 1 and synthetic route 2, using the same experimental conditions and analytical test methods as in example 1, only 2-hydroxy-1- (4-morpholine) ethanone was replaced with the same number of moles of 3-hydroxy-1- (4-morpholine) -1-propanone to give a product having a molecular structure as shown in the following figure, whose homopolymer has a toluene/n-heptane adsorption selectivity coefficient of 21 at 80 ℃.
Molecular Structure of the product of example 9
Comparative example 1
According to C10H15NO4The synthetic route of (1) was prepared by dissolving 21.86g (0.15mol) of 2-hydroxy-1- (4-morpholine) ethanone and 31.56g (0.20mol) of methacrylic anhydride in 100ml of chloroform and adding 0.45g (0.004mol) of DMAP as a catalyst. Condensing and refluxing the mixture under stirring, and reacting the mixture for 30 hours at the temperature of 60 ℃. Cooling to room temperature, adding sodium bicarbonate water solution, shaking, standing, and performing rotary evaporation on the organic layer to remove the solvent. Then recrystallized to give 14.11g of product C10H15NO4. As shown in fig. 2, high resolution mass spectrometry confirmed that the molecular structure of the synthesized product was correct.
C10H15NO4Synthetic route of (1)
2.00g of product C10H15NO40.02g of Azobisisobutyronitrile (AIBN), 20ml of chloroform was placed in a round-bottomed flask equipped with magnetic stirring and condensing reflux, and reacted at 65 ℃ for 10 hours. Cooling to room temperature, and evaporating the solvent to obtain a homogeneous film. Using the same procedure as in example 1, the toluene/n-heptane adsorption selectivity coefficient at 80 ℃ was 3.8 as obtained by the swelling adsorption experiment.
Comparative example 2
In the same manner as in example 1, potassium persulfate was used to initiate radical polymerization of the hydroxyl-terminated functional group-containing polyalkylene oxide shown in the following figure, and the obtained homopolymer was subjected to solvent evaporation to obtain a homogeneous membrane, which was subjected to adsorption swelling experiments to obtain a toluene/n-heptane adsorption selectivity coefficient of 10 at 80 ℃.
Polyethylene oxide containing terminal hydroxyl functional groups
Comparative example 3
In the same manner as in example 1, potassium persulfate was used to initiate radical polymerization of a methyl ether-terminated functional group-containing polyalkylene oxide, and the obtained homopolymer was subjected to a solvent evaporation method to obtain a homogeneous membrane, which was subjected to an adsorption swelling experiment to obtain a toluene/n-heptane adsorption selectivity coefficient of 6 at 80 ℃.
Polyethylene oxide containing methyl ether end group functional group
Comparative example 4
In the same manner as in example 1, radical polymerization of a polyalkylene oxide having allyl bonds at both ends shown in the figure was initiated with potassium persulfate to give a white crosslinked polymer which was loose and insoluble in an organic solvent, and a homogeneous film could not be obtained.
Polyethylene oxide containing allyl bonds at both ends
The above-mentioned embodiments only express the embodiments of the present invention, but not should be understood as the limitation of the scope of the invention patent, it should be noted that, for those skilled in the art, many variations and modifications can be made without departing from the concept of the present invention, and these all fall into the protection scope of the present invention.
Claims (6)
1. A preparation method of polyethylene oxide containing N-acetylmorpholinyl functional groups is characterized in that two ends of the polyethylene oxide are respectively an N-acetylmorpholinyl functional group and an allyl functional group, and the steps are as follows:
firstly, under the protection of nitrogen at room temperature, adding a solvent, a catalyst A and a hydroxyl morpholone compound into a reaction container, wherein the concentration of the hydroxyl morpholone compound is 0.10-0.15 g/ml, and the molar ratio of the catalyst A to the hydroxyl morpholone compound is 0.05-1; adding ethylene oxide, wherein the dosage of the ethylene oxide is determined according to the polymerization degree of the ethylene oxide; performing ring-opening polymerization on ethylene oxide under an alkaline condition, wherein the reaction temperature is 90-150 ℃, and the reaction time is 4-24 h; cooling to room temperature after reaction, and carrying out post-treatment to obtain a product I;
secondly, adding the product I, a catalyst 4-dimethylaminopyridine DMAP and an anhydride or acid containing an allyl bond into a solvent, wherein the mass ratio of the anhydride or acid containing the allyl bond to the product I is 0.2-0.5, the molar ratio of the catalyst DMAP to the anhydride or acid containing the allyl bond is 0.005-0.008, and the concentration of the anhydride or acid containing the allyl bond is 0.04-0.06 g/ml; carrying out esterification reaction at the temperature of 40-70 ℃ for 8-16 h; cooling to room temperature after reaction, and carrying out post-treatment to obtain a final product;
one end of the molecular structure of the polyethylene oxide is an N-acetylmorpholinyl functional group, and the polymerization degree of the polyethylene oxide is 3-75; the structural formula of the N-acetylmorpholinyl functional group is shown as follows:
wherein R is1、R2、R3、R4At least one of H, alkyl with 1-10 carbon atoms, phenyl and substituted phenyl; r1、R2、R3、R4The same or different groups may be independently selected;
the structural formula of the hydroxyl morpholone compound is shown as follows:
wherein n is 1-5; r1、R2、R3、R4At least one of H, alkyl with 1-10 carbon atoms, phenyl and substituted phenyl; r1、R2、R3、R4The same or different groups may be independently selected.
2. The method for preparing poly (ethylene oxide) having N-acetylmorpholinyl functional group according to claim 1, wherein said solvent is selected from tetrahydrofuran, dimethylsulfoxide or dimethylformamide.
3. The method for preparing poly (ethylene oxide) containing N-acetylmorpholinyl functional group according to claim 1, wherein the catalyst A is selected from KOH.
4. The method according to claim 1, wherein the hydroxymorpholinone compound is 2-hydroxy-1- (4-morpholinone) ethanone, 2-hydroxy-1- (5-methyl-2- (o-tolyl) morpholinone) ethanone, or 3-hydroxy-1- (4-morpholinone) -1-propanone.
5. The method as claimed in claim 1, wherein the acid anhydride containing allyl bond comprises methacrylic anhydride and acrylic anhydride, and the acid containing allyl bond comprises methacrylic acid and acrylic acid.
6. The method for preparing poly (ethylene oxide) containing N-acetylmorpholinyl functional group according to claim 1, wherein the polymerization degree of the ethylene oxide is 5 to 11.
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| 甲基丙烯酸聚氧乙烯酯的合成;邢凤兰等;《齐齐哈尔轻工学院学报》;19931231;第9卷(第4期);第43-48页 * |
| 聚氧乙烯单甲基丙烯酸酯的合成;胡利勤;《山东工业技术》;20190403(第6期);第59-60页 * |
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