CN112341617B - Refining method of oxacycloalkanyl end-capped polyether polyol - Google Patents
Refining method of oxacycloalkanyl end-capped polyether polyol Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
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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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2603—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 from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—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 from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
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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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2642—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 from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2648—Alkali metals or compounds thereof
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/46—Post-polymerisation treatment, e.g. recovery, purification, drying
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Abstract
The invention belongs to the technical field of chemical synthesis, and particularly relates to a refining method of oxacycloalkyl end-capped polyether polyol, which comprises the steps of firstly preparing basic polyether by 3-ethyl-3-epoxypropane methanol and alkylene oxide under the action of sodium methoxide as a catalyst, then reacting the basic polyether with chloromethane under the action of sodium methoxide as a catalyst to prepare an oxacycloalkyl end-capped polyether polyol crude product, and finally washing, adding acid to neutralize, adsorbing, drying and filtering the oxacycloalkyl end-capped polyether polyol crude product to obtain the refined oxacycloalkyl end-capped polyether polyol; wherein the acid is oxalic acid or sulfuric acid; the adsorption is carried out by stirring and adsorbing by adopting an adsorbent and a filter aid, wherein the adsorbent is magnesium silicate, and the filter aid is diatomite or acid clay. The method has the advantages of scientific and efficient process, treatment time saving, P element participation reduction, green environment protection and green production realization.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a refining method of oxacycloalkyl end-capped polyether polyol.
Background
Capped polyether polyols are compounds obtained by completely replacing active hydrogens in polyether polyols with alkyl groups, and are more stable in chemical nature than uncapped polyols. The special chemical property determines the special application of the catalyst, and the catalyst can be widely applied to nonionic surfactants, additives in lubricating oil, detergents and preparation methods of polyether polyol. The oxygen heterocyclic compound can be used as a photocuring agent, a resin adsorbent and an important synthetic intermediate. The oxygen heterocyclic polyether has the properties of polyether and oxygen heterocyclic ring after being blocked, and can be used as UV filter substances and the like. The end-capped polyether is mainly prepared by Williamson (Williamson method) at present, sodium methoxide is used as a catalyst, and after the reaction, the polyether has a plurality of salts and is not easy to post-treat, so that a method different from the ordinary polyether post-treatment is needed.
Disclosure of Invention
The invention aims to provide a refining method of an oxacycloalkyl end-capped polyether polyol, which has the advantages of scientific and efficient process, treatment time saving, P element participation reduction, green and environment-friendly performance and can realize green production.
The invention relates to a refining method of an oxacycloalkanyl end-capped polyether polyol, which is characterized by comprising the following steps of: firstly, preparing basic polyether by 3-ethyl-3-epoxypropane methanol and alkylene oxide under the action of sodium methoxide as a catalyst, then reacting the basic polyether with chloromethane under the action of sodium methoxide as a catalyst to prepare an oxacycloalkyl end-capped polyether polyol crude product, and finally washing, adding acid to neutralize, adsorbing, drying and filtering the oxacycloalkyl end-capped polyether polyol crude product to obtain refined oxacycloalkyl end-capped polyether polyol;
wherein the acid is oxalic acid or sulfuric acid; the adsorption is carried out by stirring and adsorbing by adopting an adsorbent and a filter aid, wherein the adsorbent is magnesium silicate, and the filter aid is diatomite or acid clay.
Further, the method comprises the following steps:
(1) Adding 3-ethyl-3-epoxypropane methanol and catalyst sodium methoxide into a reaction kettle, heating to 100 ℃, introducing alkylene oxide, reacting at 120-130 ℃ and under the pressure of less than or equal to 0.4Mpa, curing until no pressure drop exists after the reaction is finished, cooling to below 50 ℃, preparing basic polyether, and discharging for later use; wherein, the mol ratio of the 3-ethyl-3-epoxypropane methanol to the epoxyalkane is 1:10-30 parts of sodium methoxide with the dosage of 400-600ppm;
(2) Adding basic polyether and catalyst sodium methoxide into a reaction kettle, replacing nitrogen for 3 times, heating to 90-110 ℃, reacting at a pressure of-0.08 Mpa-0.30Mpa, reacting for 1h, removing excessive methanol by removing monomers for 2h, cooling to 60-80 ℃, reacting at a pressure of 0.30Mpa-0.40Mpa, introducing chloromethane, continuing to react for 3-10h until the pressure does not drop, removing monomers for 1h, cooling and discharging to obtain an oxacycloalkyl-terminated polyether polyol crude product; wherein the molar ratio of the basic polyether to the catalyst sodium methoxide to the methyl chloride is 1:1.2-1.5:1.5-2.0.
(3) Adding water into the crude oxacycloalkyl end-capped polyether polyol, stirring for 0.5-1h, standing for 24h, taking supernatant, putting into a reaction kettle, adding acid, replacing 3 times with nitrogen, heating to 80-90 ℃, stirring for 0.5-1h, adjusting ph=4.8-5.0, adding an adsorbent and a filter aid, cooling to 65-70 ℃, stirring and adsorbing for 1.5-3h, heating, vacuum drying until the water content is less than or equal to 0.05%, and filtering to obtain refined oxacycloalkyl end-capped polyether polyol; wherein, the water consumption is 19-23% of the crude product of the oxacycloalkyl end-capped polyether polyol, the acid consumption is 3-5% of the crude product of the oxacycloalkyl end-capped polyether polyol, and the adsorbent and the filter aid consumption are 4% of the crude product of the oxacycloalkyl end-capped polyether polyol respectively. Further, the alkylene oxide is a mixture of ethylene oxide and propylene oxide, wherein the mass of the ethylene oxide accounts for 50-100% of the mass of the mixture.
Further, the functionality of the basic polyether is 1-8, and the molecular weight is 200-8000.
Further, the mass concentration of oxalic acid is 10%.
Further, the mass concentration of the sulfuric acid is 10%.
Still further, the finished oxacycloalkyl-capped polyether polyol has a final hydroxyl number of <5mg/g.
Compared with the prior art, the invention has the following beneficial effects: other acids are adopted to replace phosphoric acid for neutralization post-treatment, so that the generation of P element is reduced, and simultaneously, the adsorbent and the filter aid are added into the solution, so that the reaction period is shortened, and the production efficiency is improved. The prepared oxacycloalkanyl end capped polyether polyol product has low metal ion content, meets the requirements of smell and has better technical effect.
Detailed Description
The invention is further illustrated below with reference to examples.
All materials used in the examples are commercially available, except as specified.
Example 1:
preparing basic polyether: 480g of 3-ethyl-3-epoxypropane methanol and 2.23g (500 ppm) of sodium methoxide are added into a reaction kettle at normal temperature, negative pressure is generated, vacuum is closed, the temperature is raised to 100 ℃, 3979g (20 wt% of ethylene oxide and 80wt% of epoxypropane) of epoxyalkane is introduced, the reaction temperature is 120-130 ℃, P is less than or equal to 0.4MPa, the reaction kettle is cured until no pressure drop exists after the reaction kettle is completely filled, the temperature is reduced to below 50 ℃, and the reaction kettle is discharged for standby. The prepared basic polyether has a functionality of 1 and a molecular weight of 1003.
Example 2:
according to n (base polyether): n (CH 3 ONa): n (CH 3 Cl) =1:1.2:1.5, charging 668g of the base polyether prepared in example 1 and 43.2g of sodium methoxide solid into a reaction kettle, replacing nitrogen for 3 times, heating to 100 ℃, reacting for 1h, removing excessive methanol by removing monomers, cooling to 68-73 ℃, introducing 50.4g of chloromethane in a negative pressure state, continuing to react until the pressure does not drop, reacting for 5h, removing monomers for 1h, cooling and discharging to obtain 692g of oxacycloalkyl-terminated polyether polyol crude product.
130g of water is added into the crude product of the oxacycloalkyl end-capped polyether polyol, the mixture is stirred for 0.5h and is kept stand for 24h, and the supernatant fluid is taken for post treatment. Adding 587g of supernatant into a reaction kettle, adding 1.53g of sulfuric acid, replacing with nitrogen for three times, heating to 80 ℃ and stirring for 0.5h, measuring the neutral pH to be 4.96, adding 2.3g of magnesium silicate adsorbent and 2.3g of acid clay, cooling to 70 ℃, stirring and adsorbing for 2h, heating and vacuum drying, and filtering to obtain the refined oxacycloalkyl-terminated polyether polyol after the moisture content is less than or equal to 0.05%.
The measured index is: ohv=4.34 ph=6.01av=0.04 Na + ＝2ppm。
Example 3:
according to n (basic polyether): n (CH 3 ONa): n (CH 3 Cl) =1:1.2:1.4, 877g of the basic polyether prepared in example 1 and 56.6g of sodium methoxide solid are put into a reaction kettle, nitrogen is replaced for three times, the temperature is raised by 100 ℃, the reaction is carried out for 1h, the excess methanol is removed by removing monomers, the temperature is reduced to 68-73 ℃, 61.8g of chloromethane is introduced under the negative pressure state, the reaction is continued until the pressure is not reduced, the reaction is carried out for 5h, the monomers are removed for 1h, and the temperature is reduced and the discharging is carried out to obtain 938g of oxacycloalkanyl end capped polyether polyol crude product.
176g of water is added into the crude product of the oxacycloalkyl end-capped polyether polyol, the mixture is stirred for 0.5h and is kept stand for 24h, and the supernatant fluid is taken for post treatment. Adding 523g of supernatant into a reaction kettle, adding 2.04g of oxalic acid, replacing with nitrogen for three times, heating to 80 ℃ and stirring for 0.5h, measuring the neutral pH to be 5.0, adding 2.1g of magnesium silicate adsorbent and 2.1g of acid clay, cooling to 70 ℃, stirring and adsorbing for 2h, heating and vacuum drying, and filtering to obtain the refined oxacycloalkyl-terminated polyether polyol after the moisture is less than or equal to 0.05%.
The measured index is: ohv=4.89 ph=6.12av=0.10na + ＝5ppm
Example 4:
according to n (base polyether): n (CH 3 ONa): n (CH 3 Cl) =1:1.2:2, adding 706g of the base polyether prepared in example 1 and 45.6g of sodium methoxide solid into a reaction kettle, replacing nitrogen for three times, heating to 100 ℃, reacting for 1h, removing excessive methanol by removing monomers, cooling to 68-73 ℃, introducing 71.1g of chloromethane in a negative pressure state, continuing to react until the pressure does not drop, reacting for 5h, removing monomers for 1h, cooling and discharging to obtain 733g of oxacycloalkyl-terminated polyether polyol crude product.
132g of water is added into the crude product of the oxacycloalkyl end-capped polyether polyol, the mixture is stirred for 0.5h and is kept stand for 24h, and the supernatant fluid is taken for post treatment. Adding 400g of supernatant into a reaction kettle, adding 1.99g of oxalic acid, replacing with nitrogen for three times, heating to 80 ℃ and stirring for 0.5h, measuring the neutral pH to be 4.87, adding 1.6g of magnesium silicate adsorbent and 1.6g of diatomite, cooling to 70 ℃, stirring and adsorbing for 2h, heating and vacuum drying, and filtering to obtain the refined oxacycloalkyl-terminated polyether polyol after the moisture is less than or equal to 0.05%.
The measured index is: ohv=2.42 ph=5.87 av=0.04 Na + ＝3ppm。
Comparative example 1:
the procedure is as in example 2 except that the amounts of magnesium silicate and acid clay added are 1% per mill and 0.58g each. The measured index is: ohv=4.77 ph=6.12av=0.11 Na + ＝44ppm。
Comparative example 2:
the specific steps are the same as those in example 2, the acid is phosphoric acid in the neutralization with post-treatment, and the measured index is not repeated: ohv=3.77 ph=6.33 av=0.21 Na + ＝8ppm。
Table 1: quality test data for the methyl capped polyethers prepared in examples 2-4 and comparative examples 1-2.
| Formaldehyde content (ppm) | Acetaldehyde content (ppm) | Acrolein content (ppm) | Odor rating | |
| Example 2 | 0.26 | 0.25 | 0.12 | 3 |
| Example 3 | 0.31 | 0.26 | 0.23 | 3 |
| Example 4 | 0.29 | 0.31 | 0.14 | 3 |
| Comparative example 1 | 1.01 | 0.68 | 0.37 | 3 |
| Comparative example 2 | 0.77 | 0.77 | 0.42 | 4 |
As can be seen from the table, when sulfuric acid and oxalic acid are tested to replace the phosphoric acid neutralization post-treatment, and the adsorbent and the filter aid are respectively 4 per mill of the mass of polyether, the measured indexes are better than those of the phosphoric acid neutralization post-treatment, and the dosages of the adsorbent and the filter aid are respectively 1 per mill.
Claims (3)
1. A refining method of an oxacycloalkanyl end-capped polyether polyol is characterized in that: firstly, preparing basic polyether by 3-ethyl-3-epoxypropane methanol and alkylene oxide under the action of sodium methoxide as a catalyst, then reacting the basic polyether with chloromethane under the action of sodium methoxide as a catalyst to prepare an oxacycloalkyl end-capped polyether polyol crude product, and finally washing, adding acid to neutralize, adsorbing, drying and filtering the oxacycloalkyl end-capped polyether polyol crude product to obtain refined oxacycloalkyl end-capped polyether polyol;
wherein the acid is oxalic acid or sulfuric acid; the adsorption is carried out by adopting an adsorbent and a filter aid, wherein the adsorbent is magnesium silicate, and the filter aid is diatomite or acid clay;
the refining method of the oxacycloalkyl end-capped polyether polyol comprises the following steps:
(1) Adding 3-ethyl-3-epoxypropane methanol and catalyst sodium methoxide into a reaction kettle, heating to 100 ℃, introducing alkylene oxide, reacting at 120-130 ℃ and under the pressure of less than or equal to 0.4Mpa, curing until no pressure drop exists after the reaction is finished, cooling to below 50 ℃, preparing basic polyether, and discharging for later use; wherein, the mol ratio of the 3-ethyl-3-epoxypropane methanol to the epoxyalkane is 1:10-30 parts of sodium methoxide with the dosage of 400-600ppm;
(2) Adding basic polyether and catalyst sodium methoxide into a reaction kettle, replacing nitrogen for 3 times, heating to 90-110 ℃, reacting at a pressure of-0.08 Mpa-0.30Mpa, reacting for 1h, removing excessive methanol by removing monomers for 2h, cooling to 60-80 ℃, reacting at a pressure of 0.30Mpa-0.40Mpa, introducing chloromethane, continuing to react for 3-10h until the pressure does not drop, removing monomers for 1h, cooling and discharging to obtain an oxacycloalkyl-terminated polyether polyol crude product; wherein, the mol ratio of the basic polyether to the catalyst sodium methoxide to the chloromethane is 1:1.2-1.5:1.5-2.0;
(3) Adding water into the crude oxacycloalkyl end-capped polyether polyol, stirring for 0.5-1h, standing for 24h, taking supernatant, putting into a reaction kettle, adding acid, replacing 3 times with nitrogen, heating to 80-90 ℃, stirring for 0.5-1h, adjusting ph=4.8-5.0, adding an adsorbent and a filter aid, cooling to 65-70 ℃, stirring and adsorbing for 1.5-3h, heating, vacuum drying until the water content is less than or equal to 0.05%, and filtering to obtain refined oxacycloalkyl end-capped polyether polyol; wherein, the water consumption is 19-23% of the crude product of the oxacycloalkyl end-capped polyether polyol, the acid consumption is 3-5% of the crude product of the oxacycloalkyl end-capped polyether polyol, and the adsorbent and the filter aid consumption are 4% of the crude product of the oxacycloalkyl end-capped polyether polyol respectively;
the alkylene oxide is a mixture of ethylene oxide and propylene oxide, wherein the mass of the ethylene oxide accounts for 50-100% of the mass of the mixture;
the functionality of the basic polyether is 1-8, and the molecular weight is 200-8000;
the mass concentration of the oxalic acid is 10%.
2. The method for purifying an oxacycloalkyl-terminated polyether polyol according to claim 1, wherein: the mass concentration of the sulfuric acid is 10%.
3. The method for purifying an oxacycloalkyl-terminated polyether polyol according to claim 1, wherein: the final hydroxyl number of the refined oxacycloalkyl-terminated polyether polyol is <5mg/g.
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