CN102795973B - Synthetic method of ethylene glycol monoallyl ether - Google Patents
Synthetic method of ethylene glycol monoallyl ether Download PDFInfo
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- CN102795973B CN102795973B CN201210291423.4A CN201210291423A CN102795973B CN 102795973 B CN102795973 B CN 102795973B CN 201210291423 A CN201210291423 A CN 201210291423A CN 102795973 B CN102795973 B CN 102795973B
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- ethylene glycol
- glycol list
- attapulgite
- propenyl ether
- oxyethane
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Abstract
The invention relates to a synthesis method of ethylene glycol monoallyl ether. The method is characterized by: adding allyl alcohol and a catalyst into a reaction kettle, sealing the reaction kettle and then conducting stirring, at the same time carrying out heating to a set reaction temperature, then stopping heating, controlling the reaction pressure at 0.2-0.4MPa, and according to a molar ratio 6-2:1 of allyl alcohol to ethylene oxide, introducing the ethylene oxide into the reaction kettle continuously, after finishing ethylene oxide introduction, carrying out thermal preservation till the pressure inside the reaction kettle no longer declines, introducing cooling water to cool a discharged material, thus obtaining the ethylene glycol monoallyl ether. The catalyst is a loaded potassium fluoride/attapulgite solid catalyst. The method has the advantages of simple process, low energy and material consumption, less equipment investment, high ethylene oxide conversion rate, good environmental protection property, reusable catalyst, and effectively reduced production cost.
Description
Technical field
The present invention relates to a kind of method of synthesizing glycol list propenyl ether.Belong to technology of fine chemicals.
Background technology
Ethylene glycol list propenyl ether (Ethylene glycol monoallyl ether), claims again: allyl group hydroxyethyl ether is one of essential industry derivative of epoxy compounds, is very important fine chemicals.In its chemical structure, have two group---hydroxyl and ehter bonds that dissolve function, the former has wetting ability, solubilized hydrophilic compounds; The latter has lipophilicity, solubilized hydrophobic nature compound.In addition, ethylene glycol list propenyl ether also contains polymerizable functional group, demonstrates higher activity, is a kind of reactive thinner in solidify material.
Along with the development of society to the pay attention to day by day of environmental protection and science and technology, eco-friendly photocuring technology has also obtained fast development, has been widely used in the fields such as tackiness agent, coating, microelectronics, ink and gear division reparation.In photo-curing material, conventional reactive thinner be take vinylformic acid polyfunctional monomer as main at present, but the shortcomings such as their viscosity is high, flash-point is low, volatility is large, irritant gas is hidden, toxicity is large, and many vinylformic acid polyfunctional monomers are carcinogenic substances, and the problem of environmental pollution bringing in use is difficult to overcome.Therefore developing new reactive thinner and studying corresponding catalytic reaction process is highly significant.
At present, industrial many employing potassium hydroxide or sodium hydroxide are as the catalyzer of synthesizing glycol list propenyl ether.Although potassium hydroxide or sodium hydroxide have the advantages such as catalytic activity is high, the reaction times is short, but exist product distribute wide, catalyzer is not easily separated and recycling, to problems such as equipment corrosion are large, environmental pollution is serious.Need badly and adopt little, pollution-free, the segregative new catalyst of corrosion to replace it, adopting solid catalyst is to get rid of an effective approach that passes etherification reaction technology drawback.
Summary of the invention
The object of the invention is to overcome above-mentioned deficiency, a kind of method of synthesizing glycol list propenyl ether is provided, the method technique is simple, energy consumption, material consumption are low, and facility investment is few, and oxyethane transformation efficiency is high, the feature of environmental protection is good, and can repeatedly use, and has effectively reduced production cost.
The object of the present invention is achieved like this: a kind of method of synthesizing glycol list propenyl ether, vinylcarbinol and catalyzer are added in reactor, airtight rear stirring, be heated to design temperature, control reaction pressure is 0.20 ~ 0.40MPa simultaneously, by vinylcarbinol and oxyethane mol ratio 2 ~ 6:1, continue to pass into oxyethane in reactor, after oxyethane imports, be incubated logical water coolant to 30 ℃ discharging while no longer declining to reacting kettle inner pressure, obtain ethylene glycol list propenyl ether.
Described catalyzer is loading type Potassium monofluoride/Attapulgite solid catalyst.
The preparation method of described loading type Potassium monofluoride/Attapulgite solid catalyst: by carrier Attapulgite as for activating in retort furnace; In potassium fluoride solution, add the Attapulgite after activation, stirred for several hour, then adds heat extraction solvent, dry at a certain temperature, and roasting at a certain temperature obtains Potassium monofluoride/Attapulgite solid catalyst.
The preparation condition of described catalyzer: 200 ~ 600 ℃ of maturing temperatures, Potassium monofluoride charge capacity 10% ~ 40%.
Catalyzer provided by the present invention is prepared in accordance with the following methods: by carrier Attapulgite as in retort furnace 200 ℃ activation 2h, by KFH
2o is dissolved in 300mL dehydrated alcohol, adds the Attapulgite carrier after activation, adds phase-transfer catalyst PEG-4000 (to account for KFH
2o and Attapulgite total mass 5%), stir 3h at 60 ℃, be heated to 105 ℃ and boil off second alcohol and water, vacuum-drying 10h at 110 ℃, as for roasting 5h at a certain temperature in retort furnace, obtains loading type Potassium monofluoride/Attapulgite solid catalyst.
As a step more of the present invention is limited, in method of the present invention, catalyst levels is 0.5 ~ 2.5% of reactant total mass, and temperature of reaction is 80 ~ 120 ℃.
As a step more of the present invention is limited, in method of the present invention, vinylcarbinol and oxyethane mol ratio are 3 ~ 6:1, are preferably 5 ~ 6:1.
While adopting pickling process that KF is loaded on to Attapulgite surface, the adding of organic solvent ethanol and phase-transfer catalyst PEG-4000, make to remain on carrier surface hydroxyl, the F that hydroxyl and KF discharge
-form [Al-OHF
-] class material, the specific surface area of KF dispersity and catalyzer is increased.In addition, catalyzer has generated K after high-temperature roasting
3alF
6, due to KF and K
3alF
6synergy, thereby at catalyst surface, formed the active site of a series of dispersions, formed the active centre of solid catalyst, during catalyzed reaction and vinylcarbinol effect form alkoxyl group negatively charged ion, attack oxyethane, by SN
2course is carried out nucleophilic substitution, and the product negatively charged ion of formation obtains H from catalyst surface again
+, generating glycol list propenyl ether.
Compared with prior art, the invention has the beneficial effects as follows:
1, because catalyzer adopts solid catalyst, in reaction process, do not dissolve, react rear filtration separable, be easy to remove minimizing energy consumption.
2, in reaction, do not need N-process, synthetic ethylene glycol propenyl product non-wastewater discharge, pollution-free.
3, oxyethane transformation efficiency is high, can, up to 99.13%, without side reaction, occur.
4, catalyst activity is high, and usage quantity is few, and can reuse, and catalyzer cost is low.
Embodiment
By following instance, the invention will be further described, but not thereby limiting the invention.
In embodiment, vinylcarbinol and oxyethane are analytical pure, and oxyethane Wei Yangzi petro-chemical corporation produces.
In embodiment, reactor is the GSH-2 type stainless steel cauldron that Weihai Chemical Machinery Co., Ltd. produces, and its volume is 2L.Reactor is furnished with spiral coil cooling tube, by control, passes into the water yield in spiral coil cooling tube, can take away in time the heat in reactor, thereby reaches the object of controlling temperature of reaction.
In embodiment, after reaction, the concentration of each material is carried out quantitative analysis with gas chromatograph.Adopt GC9790 type gas chromatograph, split stream sampling, is furnished with temperature programming parts, flame ionization ditector.Capillary chromatograph is ATSE-54 type 30m * 0.32mm * 0.45 μ m.
In embodiment, the transformation efficiency of oxyethane calculates by following formula:
In embodiment, catalyzer is prepared in accordance with the following methods: take 42g carrier Attapulgite as for 200 ℃ of activation 2h in retort furnace, by 29.2KFH
2o is dissolved in 300mL dehydrated alcohol, add the Attapulgite carrier after activation, add 3g PEG-4000, at 60 ℃, stir 3h, be heated to 105 ℃ and boil off second alcohol and water, vacuum-drying 10h at 110 ℃, as in retort furnace at 400 ℃ roasting 5h, obtain loading type Potassium monofluoride/Attapulgite solid catalyst.
Embodiment 1
5.01g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 80 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 80 ℃.After reaction finishes, oxyethane transformation efficiency is 76.44%, and ethylene glycol list propenyl ether productive rate is 67.29%.
Embodiment 2
5.01g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 90 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 90 ℃.After reaction finishes, oxyethane transformation efficiency is 89.68%, and ethylene glycol list propenyl ether productive rate is 77.44%.
Embodiment 3
5.01g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 97.46%, and ethylene glycol list propenyl ether productive rate is 81.50%.
Embodiment 4
Just 5.01g catalyzer and 290g vinylcarbinol join in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 110 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 110 ℃.After reaction finishes, oxyethane transformation efficiency is 93.71%, and ethylene glycol list propenyl ether productive rate is 78.23%.
Embodiment 5
5.01g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 120 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 120 ℃.After reaction finishes, oxyethane transformation efficiency is 92.76%, and ethylene glycol list propenyl ether productive rate is 75.96%.
Embodiment 6
3.60g catalyzer and 174g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 66g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 2:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 60.34%, and ethylene glycol list propenyl ether productive rate is 50.71%.
Embodiment 7
3.27g catalyzer and 174g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 3:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 71.73%, and ethylene glycol list propenyl ether productive rate is 59.61%.
Embodiment 8
4.14g catalyzer and 232g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 4:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 85.64%, and ethylene glycol list propenyl ether productive rate is 71.22%.
Embodiment 9
5.88g catalyzer and 348g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 6:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 99.13%, and ethylene glycol list propenyl ether productive rate is 85.13%.
Embodiment 10
1.67g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 77.36%, and ethylene glycol list propenyl ether productive rate is 65.88%.
Embodiment 11
3.34g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 82.24%, and ethylene glycol list propenyl ether productive rate is 70.04%.
Embodiment 12
6.68g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 96.94%, and ethylene glycol list propenyl ether productive rate is 81.21%.
Embodiment 13
8.35g catalyzer and 290g vinylcarbinol are joined in the reactor that volume is 2L, airtight rear stirring, intensification, when temperature reaches 100 ℃, stop heating, continue to import oxyethane 44g in reactor, now the mol ratio of vinylcarbinol and oxyethane is 5:1, and control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and the water yield control temperature of reaction passing in reactor spiral coil cooling tube by adjusting is constant in 100 ℃.After reaction finishes, oxyethane transformation efficiency is 94.81%, and ethylene glycol list propenyl ether productive rate is 79.31%.
Claims (9)
1. the synthetic method of an ethylene glycol list propenyl ether, it is characterized in that: vinylcarbinol and catalyzer are added in reactor, airtight rear stirring, be heated to design temperature simultaneously, control reaction pressure is 0.20 ~ 0.40MPa, in reactor, continue to pass into oxyethane, after oxyethane imports, be incubated to reacting kettle inner pressure and no longer decline, logical cooling water temperature discharging, obtain product ethylene glycol list propenyl ether, vinylcarbinol and oxyethane mol ratio are 2 ~ 6:1, and described catalyzer is loading type Potassium monofluoride/Attapulgite solid catalyst;
The preparation method of described loading type Potassium monofluoride/Attapulgite solid catalyst: by carrier Attapulgite as for activating in retort furnace; In potassium fluoride solution, add the Attapulgite after activation, stirred for several hour, then adds heat extraction solvent, dry at a certain temperature, and roasting at a certain temperature obtains Potassium monofluoride/Attapulgite solid catalyst.
2. the synthetic method of ethylene glycol list propenyl ether according to claim 1, is characterized by: described Attapulgite activation temperature is 100 ~ 500 ℃, and catalyzer maturing temperature is 200 ~ 600 ℃.
3. the synthetic method of ethylene glycol list propenyl ether according to claim 1, is characterized by: described Potassium monofluoride charge capacity is 30%.
4. the synthetic method of ethylene glycol list propenyl ether according to claim 2, is characterized in that: described loading type Potassium monofluoride/Attapulgite solid catalyst is prepared in accordance with the following methods: by carrier Attapulgite as for 200 ℃ of activation 2h in retort furnace, by KFH
2o is dissolved in 300mL dehydrated alcohol, add the Attapulgite carrier after activation, add phase-transfer catalyst PEG-4000, at 60 ℃, stir 3h, be heated to 105 ℃ and boil off second alcohol and water, vacuum-drying 10h at 110 ℃, as for 400 ℃ of roasting 5h in retort furnace, obtains loading type Potassium monofluoride/Attapulgite solid catalyst.
5. according to the synthetic method of the ethylene glycol list propenyl ether described in claim 1 or 2 or 3 or 4, it is characterized by: the catalyst levels of described setting is 0.5 ~ 2.5% of reactant total mass, reaction design temperature is 80 ~ 120 ℃.
6. according to the synthetic method of the ethylene glycol list propenyl ether described in right 5, it is characterized by: the catalyst levels of described setting is 1.5% of reactant total mass, reaction design temperature is 100 ℃.
7. the synthetic method of ethylene glycol list propenyl ether according to claim 6, is characterized by: ℃ discharging of described water quench to 30.
8. the synthetic method of ethylene glycol list propenyl ether according to claim 1, is characterized by: described vinylcarbinol and oxyethane mol ratio are 3 ~ 6:1.
9. the synthetic method of ethylene glycol list propenyl ether according to claim 8, is characterized by: described vinylcarbinol and oxyethane mol ratio are 5 ~ 6:1.
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| CN103012079B (en) * | 2012-12-17 | 2016-01-27 | 常州大学 | The method of solid base catalyst catalytically synthesizing glycol propenyl ether |
| CN103435455B (en) * | 2013-08-23 | 2015-04-29 | 扬州晨化新材料股份有限公司 | Preparation method of ethylene glycol allyl ether |
| CN104710609B (en) * | 2015-04-02 | 2016-09-14 | 山西凯迪建材有限公司 | A kind of method photocatalytically carrying out ethoxylation generation polyethers |
| CN106187712B (en) * | 2016-07-04 | 2019-11-22 | 江门谦信化工发展有限公司 | A kind of industrially prepared system and preparation method of propylene glycol phenylate |
| CN111269093B (en) * | 2018-12-05 | 2022-10-11 | 上海多纶化工有限公司 | Preparation method of secondary alcohol polyoxyethylene ether |
| CN113061243B (en) * | 2021-03-30 | 2022-07-05 | 浙江皇马科技股份有限公司 | Preparation method of allyl alcohol polyoxypropylene ether |
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| CN101172227A (en) * | 2006-11-02 | 2008-05-07 | 中国石油化工股份有限公司 | Catalyzer for glycol ether preparation with oxirane |
| CN101190876B (en) * | 2006-11-21 | 2010-05-12 | 中国石油化工股份有限公司 | Method for preparing ethylene glycol ether |
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