CN105601902A - Synthetic method of sucrose polyoxypropylene - Google Patents
Synthetic method of sucrose polyoxypropylene Download PDFInfo
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- CN105601902A CN105601902A CN201610024632.0A CN201610024632A CN105601902A CN 105601902 A CN105601902 A CN 105601902A CN 201610024632 A CN201610024632 A CN 201610024632A CN 105601902 A CN105601902 A CN 105601902A
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- sucrose
- ether
- synthetic method
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- polyethenoxy
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/22—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the initiator used in polymerisation
- C08G2650/26—Sugars or saccharides used as initiators
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
Abstract
The invention relates to sucrose polyoxypropylene and a synthetic method thereof, and belongs to the technical field of organic compounds. The synthetic method includes: taking sucrose and propylene oxide as raw materials, adding the sucrose, catalyst and ether solvent into a reaction kettle, performing vacuum pumping, and heating up in nitrogen protection till the sucrose is completely dissolved in the ether solvent; adding a chain extension agent, heating up to perform polyreaction of the sucrose polyoxypropylene prior to cooling, and subjecting crystallization mother liquor to normal pressure or decompression rectification to separate ether solvent which can be applied to a next reaction process. The method is applied to synthesis of the sucrose polyoxypropylene, realizes high yield and high hydroxyl value, and ensures that the color value is under 30, and the requirements on both degree of polymerization and color value can be met.
Description
Technical field
The present invention relates to a kind of synthetic method of sucrose polyethenoxy ether, belong to organic compound technical field.
Background technology
Polyether polyol resin is the primary raw material of producing the various goods of polyurethane, although the polyether polyol resin of the different trades mark of producing both at home and abroad reaches hundreds of, but in the polyethers kinds such as use for hard bubble of polyurethane sucrose, sweet mellow wine, sorbierite, xylitol, pentaerythrite, glucose glucosides, ethylenediamine, urea element, glycerine, but dominate of sucrose polyethers. Its reason is:
(1) sucrose is as initiator, and its molecular weight is large (342.3), produces the epoxides that same molecular amount polyethers consumes less, saved the consumption of epoxides, this be above-mentioned other initiator can't be obtained.
(2) sucrose is more stable, is easier to react with epoxides when synthesizing polyether.
(3) from chemical constitution, sucrose is high functionality (degree of functionality the is 8) initiator with twin nuclei, and synthetic polyethers is applicable to high, medium and low density polyurethane and hard bubbles.
(4) sucrose is wider in distributed in nature, and is that a kind of price comparison is cheap, and purity is high, reproducible green material,
(5) in the time that use is total to initiator, sucrose polyethers and other polyethers, polyisocyanates, blowing agent water and F11Deng intermiscibility better; Meanwhile, sucrose polyethers has excellent elimination and suppresses foaming, is good defoamer.
But, the fusing point of sucrose is higher, arrive 186 DEG C, the prior synthesizing method of sucrose polyethenoxy ether is to depress high temperature under KOH catalysis and react with expoxy propane adding, and can cause like this product color dark, and because cannot use external circulating device, cause mixing of materials inhomogeneous, cause expoxy propane to have residual, caused environmental pollution and waste resource, and use KOH catalyst, need post processing dehydration absorption desalination. Patent 201410159270.7 (application number), although solved sucrose polyethers building-up process and cannot use a difficult problem for external circulating device, is used organic amine catalyst, does not well solve the dark problem of product color.
Based on this, make the application.
Summary of the invention
In order to overcome existing above-mentioned defect in existing sucrose polyethenoxy ether building-up process, the synthetic method that the invention provides a kind of new sucrose polyethenoxy ether, the method preparation technology is simple, is easy to industrializing implementation, products obtained therefrom lighter color, the feature that content is high.
For achieving the above object, the technical scheme that the present invention takes is as follows:
A synthetic method for sucrose polyethenoxy ether, taking sucrose and expoxy propane as raw material, concrete steps are as follows:
(1) material is dissolved: sucrose, catalyst and ether solvent are added to reactor, vacuumize, under nitrogen protection, be warming up to sucrose and be dissolved in completely in ether solvent;
(2) add cahin extension agent, polymerization: after sucrose is dissolved in ether solvent completely, add cahin extension agent, heat up and carry out the polymerisation of sucrose polyethenoxy ether;
(3) desolventizing: after polymerisation finishes, cooling, crystalline mother solution is isolated ether solvent through normal pressure or rectification under vacuum, can overlap for next course of reaction.
Further, as preferably:
In step (1), described ether solvent is any one in di-n-propyl ether, di-n-butyl ether, ethylene glycol diethyl ether, ethylene glycol bisthioglycolate positive propyl ether, ethylene glycol bisthioglycolate isopropyl ether, ethylene glycol bisthioglycolate n-butyl ether, ethylene glycol bisthioglycolate isobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-propyl ether, diethylene glycol diisopropyl ether, diethylene glycol di-n-butyl ether or diethylene glycol diisobutyl ether.
In step (1), described catalyst is BFEE.
In step (1), described material temperature is 100~120 DEG C.
In step (2), described cahin extension agent is expoxy propane.
Described sucrose: cahin extension agent: solvent (mol ratio) is 1:9.5~10.5:0.3~1.5, the mass ratio of catalyst and sucrose is 1:140~2000.
In step (2), described polymeric reaction temperature is 110~120 DEG C, and reaction pressure is-0.05-0.4Mpa.
In step (3), separated from solvent temperature is 80~130 DEG C.
It is after polymerisation finishes that described solvent is applied mechanically, and adopts the mode of low pressure or normal pressure (setting depending on solvent boiling point) distillation, through chilled brine lowered temperature reclamation, can reach the rate of recovery of 98-99%.
The invention has the beneficial effects as follows: the main synthesis technique that improves sucrose polyethenoxy ether of the present invention, and applicable catalytic amount and reaction temperature, reaction pressure, thus make reaction than the component state that is easier to be controlled at product requirement.
Compared with the prior art, first the present invention dissolves sucrose with ether solvent, react with cahin extension agent expoxy propane again, greatly reduce the possibility that color and luster that high-temperature melting method material causes because temperature is too high is deepened, and make can use external circulating device in the building-up process of sucrose polyethenoxy ether. Ether solvent used can be selected di-n-propyl ether, di-n-butyl ether, ethylene glycol diethyl ether, ethylene glycol bisthioglycolate positive propyl ether, ethylene glycol bisthioglycolate isopropyl ether, ethylene glycol bisthioglycolate n-butyl ether, ethylene glycol bisthioglycolate isobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-propyl ether, diethylene glycol diisopropyl ether, diethylene glycol di-n-butyl ether or diethylene glycol diisobutyl ether etc.; And the present invention has adopted BFEE as catalyst, do not need post processing desalination process, compared with prior art, saved production time and production cost, improved the yield of sucrose polyethenoxy ether, can not be also that product color is deepened as organic amine catalyst in course of reaction.
Compared with prior art, the outstanding advantages that the present invention has is:
(1) easy control of reaction system, can not produce the wayward phenomenon of reaction temperature, and occurrence probability of safety accidents reduces greatly.
(2) prepare the lighter color of sucrose polyethenoxy ether, lower than 30 (Pt-Co methods)
(3) technique is simple, is easy to environmental protection, needn't carry out aftertreatment technology, the solid waste such as the raw phosphate producing while avoiding post processing and polyethers adsorbent diatomite thereof.
(4) described in the building-up process of sucrose polyethenoxy ether, ether solvent is capable of circulation applies mechanically, thereby makes technique environmental protection more.
(5) content of the sucrose polyethenoxy ether of once preparing is up to more than 99%, and product quality improves greatly.
Adopt synthetic route provided by the present invention, obtaining sucrose polyethenoxy ether index is that hydroxyl value is 470-480mgKOH/g, color and luster≤30, and the product of sucrose polyoxypropylene ether content >=99% can meet the requirement of the degree of polymerization and colour two aspects simultaneously.
Detailed description of the invention
The preparation of reactor before implementing: first with distilled water, 2.5L autoclave is washed several times, until clean, oven dry reactor, for subsequent use after being cooled to 50~70 DEG C.
Embodiment 1
In reactor, add sucrose 513g, BFEE 1.5g, diethylene glycol diethyl ether 500g vacuumizes with vavuum pump, adopts N2Displace the air in reactor; replace after three times; under nitrogen protection, be warmed up to 110 DEG C, insulation 4h, treats that in still, material is complete; vacuumize 15 minutes; then controlling reaction temperature is 115 DEG C, and reactor pressure, at-0.05-0.4Mpa, continues to add expoxy propane 914g; add rear insulation and continue reaction, until reaction pressure no longer declines. React complete, be cooled to 70 DEG C, unreacted expoxy propane is removed in vacuum outgas, and mother liquor is warming up to gradually 115 DEG C and obtains product through decompression distillation 9h, and the cooling rear reception of solvent vapour can be applied mechanically again.
Product is through liquid-phase chromatographic analysis: sucrose polyoxypropylene ether content 99.5%; No. 15, sample color and luster (Pt-Co), adopting GB/T12008.3-2009 to measure hydroxyl value is 475.4mgKOH/g.
Embodiment 2
In reactor, add sucrose 513g, BFEE 1.5g, vacuumizes through reclaiming the diethylene glycol diethyl ether 492g vavuum pump obtaining, and adopts N2Displace the air in reactor; replace after three times; under nitrogen protection, be warmed up to 110 DEG C, insulation 4h, treats that in still, material is complete; vacuumize 15 minutes; then controlling reaction temperature is 115 DEG C, and reactor pressure, at-0.05-0.4Mpa, continues to add expoxy propane 914g; add rear insulation and continue reaction, until reaction pressure no longer declines. React complete, be cooled to 70 DEG C, unreacted expoxy propane is removed in vacuum outgas, and mother liquor is warming up to gradually 115 DEG C and obtains product through decompression distillation 9h, and the cooling rear reception of solvent vapour can be applied mechanically again.
Product is through liquid-phase chromatographic analysis: sucrose polyoxypropylene ether content 99.3%; No. 20, sample color and luster (Pt-Co), adopting GB/T12008.3-2009 to measure hydroxyl value is 476.1mgKOH/g.
Embodiment 3
In reactor, add sucrose 513g, BFEE 1.0g, ethylene glycol bisthioglycolate n-butyl ether 510g vacuumizes with vavuum pump, adopts N2Displace the air in reactor; replace after three times; under nitrogen protection, be warmed up to 110 DEG C, insulation 4h, treats that in still, material is complete; vacuumize 15 minutes; then controlling reaction temperature is 118 DEG C, and reactor pressure, at-0.05-0.4Mpa, continues to add expoxy propane 914g; add rear insulation and continue reaction, until reaction pressure no longer declines. React complete, be cooled to 70 DEG C, unreacted expoxy propane is removed in vacuum outgas, and mother liquor is warming up to gradually 120 DEG C and obtains product through decompression distillation 9h, and the cooling rear reception of solvent vapour can be applied mechanically again.
Product is through liquid-phase chromatographic analysis: sucrose polyoxypropylene ether content 99.4%; No. 15, sample color and luster (Pt-Co), adopting GB/T12008.3-2009 to measure hydroxyl value is 477.2mgKOH/g.
Embodiment 4
In reactor, add sucrose 513g, BFEE 1.0g, vacuumizes through reclaiming the ethylene glycol bisthioglycolate n-butyl ether 503g vavuum pump obtaining, and adopts N2Displace the air in reactor; replace after three times; under nitrogen protection, be warmed up to 110 DEG C, insulation 4h, treats that in still, material is complete; vacuumize 15 minutes; then controlling reaction temperature is 118 DEG C, and reactor pressure, at-0.05-0.4Mpa, continues to add expoxy propane 914g; add rear insulation and continue reaction, until reaction pressure no longer declines. React complete, be cooled to 70 DEG C, unreacted expoxy propane is removed in vacuum outgas, and mother liquor is warming up to gradually 120 DEG C and obtains product through decompression distillation 9h, and the cooling rear reception of solvent vapour can be applied mechanically again.
Product is through liquid-phase chromatographic analysis: sucrose polyoxypropylene ether content 99.4%; No. 25, sample color and luster (Pt-Co), adopting GB/T12008.3-2009 to measure hydroxyl value is 478.3mgKOH/g.
Embodiment 5
In reactor, add sucrose 513g, BFEE 0.8g, di-n-butyl ether 300g vacuumizes with vavuum pump, adopts N2Displace the air in reactor; replace after three times; under nitrogen protection, be warmed up to 110 DEG C, insulation 4h, treats that in still, material is complete; vacuumize 15 minutes; then controlling reaction temperature is 113 DEG C, and reactor pressure, at-0.05-0.4Mpa, continues to add expoxy propane 914g; add rear insulation and continue reaction, until reaction pressure no longer declines. React complete, be cooled to 70 DEG C, unreacted expoxy propane is removed in vacuum outgas, and mother liquor is warming up to gradually 110 DEG C and obtains product through decompression distillation 7h, and the cooling rear reception of solvent vapour can be applied mechanically again.
Product is through liquid-phase chromatographic analysis: sucrose polyoxypropylene ether content 99.2%; No. 10, sample color and luster (Pt-Co), adopting GB/T12008.3-2009 to measure hydroxyl value is 473.7mgKOH/g.
Embodiment 6
In reactor, add sucrose 513g, BFEE 0.8g, vacuumizes through reclaiming the di-n-butyl ether 294g vavuum pump obtaining, and adopts N2Displace the air in reactor; replace after three times; under nitrogen protection, be warmed up to 110 DEG C, insulation 4h, treats that in still, material is complete; vacuumize 15 minutes; then controlling reaction temperature is 113 DEG C, and reactor pressure, at-0.05-0.4Mpa, continues to add expoxy propane 914g; add rear insulation and continue reaction, until reaction pressure no longer declines. React complete, be cooled to 70 DEG C, unreacted expoxy propane is removed in vacuum outgas, and mother liquor is warming up to gradually 110 DEG C and obtains product through decompression distillation 7h, and the cooling rear reception of solvent vapour can be applied mechanically again.
Product is through liquid-phase chromatographic analysis: sucrose polyoxypropylene ether content 99.1%; No. 20, sample color and luster (Pt-Co), adopting GB/T12008.3-2009 to measure hydroxyl value is 472.9mgKOH/g.
Comparative example 1
In reactor, add sucrose 513g, KOH1.2g vacuumizes with vavuum pump, adopts N2Displace the air in reactor; replace after three times, under nitrogen protection, be warmed up to 180 DEG C, insulation 6h; treat that in still, material is complete; vacuumize 20 minutes, then cooling, controlling reaction temperature is 115 DEG C; reactor pressure is at-0.05-0.4Mpa; continue to add expoxy propane 914g, add rear insulation and continue reaction, until reaction pressure no longer declines. React complete, be cooled to 70 DEG C, unreacted expoxy propane is removed in vacuum outgas, and material proceeds to post processing still, adds deionized water, phosphoric acid, and adsorbent, diatomite carries out post processing desalination.
Product is through liquid-phase chromatographic analysis: sucrose polyoxypropylene ether content 98.1%; No. 55, sample color and luster (Pt-Co), adopting GB/T12008.3-2009 to measure hydroxyl value is 486.3mgKOH/g.
After tested, specific targets are as shown in table 1 for the prepared sucrose polyethenoxy ether of the various embodiments described above.
The parameter table of comparisons of finished product under table 1 different technology conditions
As can be seen from Table 1, first the scheme that the application provides dissolves sucrose with ether solvent, react with cahin extension agent expoxy propane again, greatly reduce the possibility that color and luster that high-temperature melting method material causes because temperature is too high is deepened, and make can use external circulating device in the building-up process of sucrose polyethenoxy ether, not only realize high yield and high hydroxyl value, and guaranteed that colour is below 30, can meet the requirement of the degree of polymerization and colour two aspects simultaneously.
Claims (8)
1. a synthetic method for sucrose polyethenoxy ether, is characterized in that, taking sucrose and expoxy propane as raw material, concrete steps are as follows:
(1) material is dissolved: sucrose, catalyst and ether solvent are added to reactor, vacuumize, under nitrogen protection, be warming up to sucrose and be dissolved in completely in ether solvent;
(2) add cahin extension agent, polymerization: after sucrose is dissolved in ether solvent completely, add cahin extension agent, heat up and carry out the polymerisation of sucrose polyethenoxy ether;
(3) desolventizing: after polymerisation finishes, cooling, crystalline mother solution is isolated ether solvent through normal pressure or rectification under vacuum, can overlap for next course of reaction.
2. the synthetic method of a kind of sucrose polyethenoxy ether as claimed in claim 1, it is characterized in that: in step (1), described ether solvent is any one in di-n-propyl ether, di-n-butyl ether, ethylene glycol diethyl ether, ethylene glycol bisthioglycolate positive propyl ether, ethylene glycol bisthioglycolate isopropyl ether, ethylene glycol bisthioglycolate n-butyl ether, ethylene glycol bisthioglycolate isobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-propyl ether, diethylene glycol diisopropyl ether, diethylene glycol di-n-butyl ether or diethylene glycol diisobutyl ether.
3. the synthetic method of a kind of sucrose polyethenoxy ether as claimed in claim 1, is characterized in that: in step (1), described catalyst is BFEE.
4. the synthetic method of a kind of sucrose polyethenoxy ether as claimed in claim 1, is characterized in that: in step (1), described material temperature is 100~120 DEG C.
5. the synthetic method of a kind of sucrose polyethenoxy ether as claimed in claim 1, it is characterized in that: described sucrose and the mol ratio of cahin extension agent are for being 1:9.5~10.5, the mol ratio of solvent and sucrose is 0.3~1.5:1, and the mass ratio of catalyst and sucrose is 1:140~2000.
6. the synthetic method of a kind of sucrose polyethenoxy ether of knowing well as claim 1, is characterized in that: in step (2), described polymeric reaction temperature is 110~120 DEG C, and reaction pressure is-0.05-0.4Mpa.
7. the synthetic method of a kind of sucrose polyethenoxy ether as claimed in claim 1, is characterized in that: in step (3), separated from solvent temperature is 80~130 DEG C.
8. a sucrose polyethenoxy ether, is characterized in that: described sucrose polyethenoxy ether hydroxyl value is 470-480mgKOH/g, color and luster≤30, sucrose polyoxypropylene ether content >=99%.
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Cited By (2)
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CN110527077A (en) * | 2019-08-14 | 2019-12-03 | 江门市科锐新材料有限公司 | A kind of sustained release collapse-preventing type water-reducing agent and preparation method thereof |
CN114062357A (en) * | 2021-12-15 | 2022-02-18 | 上海东大化学有限公司 | Method for rapidly detecting polyether raw material sugar |
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CN104004178A (en) * | 2014-04-19 | 2014-08-27 | 上海东大化学有限公司 | Sucrose polyether polyol, preparation method and application thereof |
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CN101497635A (en) * | 2008-12-30 | 2009-08-05 | 浙江皇马科技股份有限公司 | Preparation method of sucrose and glycerol mixed alcohol polyoxypropylene ether |
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Application publication date: 20160525 |