CN102795973A - Synthetic method of ethylene glycol monoallyl ether - Google Patents
Synthetic method of ethylene glycol monoallyl ether Download PDFInfo
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- CN102795973A CN102795973A CN2012102914234A CN201210291423A CN102795973A CN 102795973 A CN102795973 A CN 102795973A CN 2012102914234 A CN2012102914234 A CN 2012102914234A CN 201210291423 A CN201210291423 A CN 201210291423A CN 102795973 A CN102795973 A CN 102795973A
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- glycol monomethyl
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- attapulgite
- propenyl ether
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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
Glycol monomethyl propenyl ether (Ethylene glycol monoallyl ether), claim again: the allyl group hydroxyethyl ether is one of essential industry verivate of epoxy compounds, is very important fine chemicals.The group that has two dissolving functions on its chemical structure---hydroxyl and ehter bond, the former possess hydrophilic property, solubilized hydrophilic compounds; The latter has oleophilicity, solubilized hydrophobic nature compound.In addition, the glycol monomethyl propenyl ether also contains polymerizable functional group, demonstrates higher activity, is a kind of reactive thinner in the solidify material.
Along with pay attention to day by day and the scientific and technical continuous development of society to environmental protection, eco-friendly photocuring technology has also obtained fast development, has been widely used in fields such as tackiness agent, coating, microelectronics, printing ink and the reparation of tooth section.Reactive thinner commonly used is main with the vinylformic acid polyfunctional monomer in the photo-curing material at present; But shortcomings such as their viscosity is high, flash-point is low, volatility is big, have pungency gas to hide, toxicity is big; And many vinylformic acid polyfunctional monomers are carcinogenic substances, and the problem of environmental pollution that is brought in the use is difficult to overcome.Therefore developing new reactive thinner is highly significant with the corresponding catalytic reaction process of research.
At present, adopt Pottasium Hydroxide or sodium hydroxide catalyzer in the industry as synthesizing glycol list propenyl ether more.Although Pottasium Hydroxide or sodium hydroxide have advantages such as catalytic activity height, reaction times be short, but exist product distribute wide, catalyzer is not easily separated and recycling, to problems such as equipment corrosion are big, environmental pollution is serious.Need badly and adopt little, pollution-free, segregative new catalyst replacements of corrosion, to adopt solid catalyst be an effective way of getting rid of biography etherification reaction technology drawback.
Summary of the invention
The objective of the invention is to overcome above-mentioned deficiency, a kind of method of synthesizing glycol list propenyl ether is provided, this method technology is simple; Energy consumption, material consumption are low, and facility investment is few, and the oxyethane transformation efficiency is high; The feature of environmental protection is good, and can repeat repeatedly to use, and has reduced production cost effectively.
The objective of the invention is to realize like this: a kind of method of synthesizing glycol list propenyl ether, vinylcarbinol and catalyzer are added in the reaction kettle, stir airtight back; Heat temperature raising is to design temperature simultaneously, and the control reaction pressure is 0.20 ~ 0.40MPa, presses vinylcarbinol and oxyethane mol ratio 2 ~ 6:1; Continue in reaction kettle, to feed oxyethane; After oxyethane imports and finishes, be incubated when reacting kettle inner pressure no longer descends and lead to water coolant to 30 ℃ discharging, obtain the glycol monomethyl propenyl ether.
Described catalyzer is loading type Potassium monofluoride/Attapulgite solid catalyst.
The preparation method of said loading type Potassium monofluoride/Attapulgite solid catalyst: with the carrier Attapulgite as for activation in the retort furnace; In potassium fluoride solution, add the Attapulgite after the activation, stirred for several hour adds heat extraction solvent, drying then at a certain temperature, and roasting at a certain temperature obtains Potassium monofluoride/Attapulgite solid catalyst.
Described Preparation of catalysts condition: 200 ~ 600 ℃ of maturing temperatures, Potassium monofluoride charge capacity 10% ~ 40%.
Catalyzer provided by the present invention prepares according to following method: with the carrier Attapulgite as for 200 ℃ of activation 2h in the retort furnace, with KFH
2O is dissolved in the 300mL absolute ethyl alcohol, and the Attapulgite carrier after the adding activation adds phase-transfer catalyst polyoxyethylene glycol-400 and (accounts for KFH
2O and Attapulgite total mass 5%), 60 ℃ are stirred down 3h, are heated to 105 ℃ and boil off the second alcohol and water, 110 ℃ of following vacuum-drying 10h as for roasting 5h at a certain temperature in the retort furnace, obtain loading type Potassium monofluoride/Attapulgite solid catalyst.
As a step more of the present invention is limited, catalyst levels is 0.5 ~ 2.5% of a reactant total mass in the method for the present invention, and temperature of reaction is 80 ~ 120 ℃.
As a step more of the present invention is limited, vinylcarbinol and oxyethane mol ratio are 3 ~ 6:1 in the method for the present invention, are preferably 5 ~ 6:1.
When adopting pickling process that KF is loaded on the Attapulgite surface, the adding of organic solvent ethanol and phase-transfer catalyst polyoxyethylene glycol-400, making residually on the carrier surface has hydroxyl, a F that hydroxyl and KF discharge
-Form [Al-OHF
-] type material, the specific surface area of KF dispersity and catalyzer is increased.In addition, catalyzer has generated K after high-temperature roasting
3AlF
6, because KF and K
3AlF
6Synergy, thereby formed a series of dispersive active sites at catalyst surface, constituted the active site of solid catalyst, during catalyzed reaction and the vinylcarbinol effect form the alkoxyl group negatively charged ion, attack oxyethane is pressed SN
2Course is carried out nucleophilic substitution, and the product negatively charged ion of formation obtains H from catalyst surface again
+, generate the glycol monomethyl propenyl ether.
Compared with prior art, the invention has the beneficial effects as follows:
1, because catalyzer adopts solid catalyst, do not dissolve in the reaction process, it is promptly separable that after-filtration is accomplished in reaction, is easy to remove, and reduces energy consumption.
2, do not need N-process in the reaction, synthetic terepthaloyl moietie propenyl product non-wastewater discharge, pollution-free.
3, the oxyethane transformation efficiency is high, can be up to 99.13%, and no side reaction takes place.
4, catalyst activity is high, and usage quantity is few, and can reuse, and the catalyzer cost is low.
Embodiment
Through following instance the present invention is described further, but does not therefore limit the present invention.
Among the embodiment, vinylcarbinol and oxyethane are analytical pure, and oxyethane is produced for raising sub-petro-chemical corporation.
Among the embodiment, reaction kettle is the GSH-2 type stainless steel cauldron that Weihai Chemical Machinery Co., Ltd. produces, and its volume is 2L.Reaction kettle is furnished with spiral coil cooling tube, feeds the water yield in the spiral coil cooling tube through control, can in time take away the heat in the reaction kettle, thereby reach the purpose of control reaction temperature.
Among the embodiment, the concentration of each material of reaction back is carried out quantitative analysis with gas chromatograph.Adopt GC9790 type gas chromatograph, split stream sampling is furnished with the temperature programming parts, flame ionization ditector.Capillary chromatograph is ATSE-54 type 30m * 0.32mm * 0.45 μ m.
Among the embodiment, the transformation efficiency of oxyethane calculates by following formula:
Among the embodiment, catalyzer prepares according to following method: take by weighing 42g carrier Attapulgite as for 200 ℃ of activation 2h in the retort furnace, with 29.2KFH
2O is dissolved in the 300mL absolute ethyl alcohol; Attapulgite carrier after the adding activation adds 3g polyoxyethylene glycol-400, the 60 ℃ following 3h of stirring; Be heated to 105 ℃ and boil off the second alcohol and water; 110 ℃ of following vacuum-drying 10h, as in the retort furnace at 400 ℃ of following roasting 5h, obtain loading type Potassium monofluoride/Attapulgite solid catalyst.
Embodiment 1
5.01g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 80 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 80 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 76.44%, and glycol monomethyl propenyl ether productive rate is 67.29%.
Embodiment 2
5.01g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 90 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 90 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 89.68%, and glycol monomethyl propenyl ether productive rate is 77.44%.
Embodiment 3
5.01g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 97.46%, and glycol monomethyl propenyl ether productive rate is 81.50%.
Embodiment 4
Just 5.01g catalyzer and 290g vinylcarbinol join in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 110 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 110 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 93.71%, and glycol monomethyl propenyl ether productive rate is 78.23%.
Embodiment 5
5.01g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 120 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 120 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 92.76%, and glycol monomethyl propenyl ether productive rate is 75.96%.
Embodiment 6
3.60g catalyzer and 174g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 66g; This moment, the mol ratio of vinylcarbinol and oxyethane was 2:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 60.34%, and glycol monomethyl propenyl ether productive rate is 50.71%.
Embodiment 7
3.27g catalyzer and 174g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 3:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 71.73%, and glycol monomethyl propenyl ether productive rate is 59.61%.
Embodiment 8
4.14g catalyzer and 232g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 4:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 85.64%, and glycol monomethyl propenyl ether productive rate is 71.22%.
Embodiment 9
5.88g catalyzer and 348g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 6:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 99.13%, and glycol monomethyl propenyl ether productive rate is 85.13%.
Embodiment 10
1.67g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 77.36%, and glycol monomethyl propenyl ether productive rate is 65.88%.
Embodiment 11
3.34g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 82.24%, and glycol monomethyl propenyl ether productive rate is 70.04%.
Embodiment 12
6.68g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 96.94%, and glycol monomethyl propenyl ether productive rate is 81.21%.
Embodiment 13
8.35g catalyzer and 290g vinylcarbinol are joined in the reaction kettle that volume is 2L; Stirring, heat up in airtight back, when temperature reaches 100 ℃, stops heating; Continue in reaction kettle, to import oxyethane 44g; This moment, the mol ratio of vinylcarbinol and oxyethane was 5:1, and the control reacting kettle inner pressure is 0.2 ~ 0.4MPa, and is constant in 100 ℃ through regulating the water yield control reaction temperature that feeds in the reaction kettle spiral coil cooling tube.After reaction finished, the oxyethane transformation efficiency was 94.81%, and glycol monomethyl propenyl ether productive rate is 79.31%.
Claims (9)
1. the synthetic method of a glycol monomethyl propenyl ether; It is characterized in that: propenyl and catalyst are added in the reactor; Stir airtight back; Heat temperature raising is to design temperature simultaneously; The control reaction pressure is 0.20 ~ 0.40MPa; In reactor, continue to feed oxirane; After oxirane imports and finishes; Be incubated to reacting kettle inner pressure and no longer descend; Logical cooling water temperature discharging; Obtain product glycol monomethyl propenyl ether, propenyl and oxirane mol ratio are 2 ~ 6:1, and said catalyst is support type potassium fluoride/concavo-convex excellent solid catalyst;
The preparation method of said loading type Potassium monofluoride/Attapulgite solid catalyst: with the carrier Attapulgite as for activation in the retort furnace; In potassium fluoride solution, add the Attapulgite after the activation, stirred for several hour adds heat extraction solvent, drying then at a certain temperature, and roasting at a certain temperature obtains Potassium monofluoride/Attapulgite solid catalyst.
2. the compound method of glycol monomethyl propenyl ether according to claim 1 is characterized by: said Attapulgite activation temperature is 100 ~ 500 ℃, and the catalyzer maturing temperature is 200 ~ 600 ℃.
3. the compound method of glycol monomethyl propenyl ether according to claim 1 is characterized by: said Potassium monofluoride charge capacity is 30%.
4. the compound method of glycol monomethyl propenyl ether according to claim 2 is characterized in that: said loading type Potassium monofluoride/Attapulgite solid catalyst prepares according to following method: with the carrier Attapulgite as for 200 ℃ of activation 2h in the retort furnace, with KFH
2O is dissolved in the 300mL absolute ethyl alcohol; Attapulgite carrier after the adding activation adds phase-transfer catalyst polyoxyethylene glycol-400, the 60 ℃ following 3h of stirring; Be heated to 105 ℃ and boil off the second alcohol and water; 110 ℃ of following vacuum-drying 10h as for 400 ℃ of roasting 5h in the retort furnace, obtain loading type Potassium monofluoride/Attapulgite solid catalyst.
5. according to claim 1 or 2 or the compound method of 3 or 4 described glycol monomethyl propenyl ether, it is characterized by: the catalyst levels of said setting is 0.5 ~ 2.5% of a reactant total mass, and the reaction design temperature is 80 ~ 120 ℃.
6. according to the compound method of right 5 described glycol monomethyl propenyl ether, it is characterized by: the catalyst levels of said setting is 1.5% of a reactant total mass, and the reaction design temperature is 100 ℃.
7. the compound method of glycol monomethyl propenyl ether according to claim 6 is characterized by: ℃ discharging of said water quench to 30.
8. the compound method of glycol monomethyl propenyl ether according to claim 1 is characterized by: said vinylcarbinol and oxyethane mol ratio are 3 ~ 6:1.
9. the compound method of glycol monomethyl propenyl ether according to claim 8 is characterized by: said vinylcarbinol and oxyethane mol ratio are 5 ~ 6:1.
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Cited By (6)
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| CN103012079A (en) * | 2012-12-17 | 2013-04-03 | 常州大学 | Method for synthesizing ethylene glycol allyl ether under catalysis of solid base catalyst |
| CN103435455A (en) * | 2013-08-23 | 2013-12-11 | 扬州晨化新材料股份有限公司 | Preparation method of ethylene glycol allyl ether |
| CN104710609A (en) * | 2015-04-02 | 2015-06-17 | 山西凯迪建材有限公司 | Method for generating polyether by virtue of ethoxylation reaction under photocatalysis conditions |
| CN106187712A (en) * | 2016-07-04 | 2016-12-07 | 江门谦信化工发展有限公司 | The industrially prepared system of a kind of propylene glycol phenylate and preparation method |
| CN111269093A (en) * | 2018-12-05 | 2020-06-12 | 上海多纶化工有限公司 | Preparation method of secondary alcohol polyoxyethylene ether |
| CN113061243A (en) * | 2021-03-30 | 2021-07-02 | 浙江皇马科技股份有限公司 | Preparation method of allyl alcohol polyoxypropylene ether |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012079A (en) * | 2012-12-17 | 2013-04-03 | 常州大学 | Method for synthesizing ethylene glycol allyl ether under catalysis of solid base catalyst |
| CN103012079B (en) * | 2012-12-17 | 2016-01-27 | 常州大学 | The method of solid base catalyst catalytically synthesizing glycol propenyl ether |
| CN103435455A (en) * | 2013-08-23 | 2013-12-11 | 扬州晨化新材料股份有限公司 | Preparation method of ethylene glycol allyl 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 |
| CN104710609A (en) * | 2015-04-02 | 2015-06-17 | 山西凯迪建材有限公司 | Method for generating polyether by virtue of ethoxylation reaction under photocatalysis conditions |
| CN106187712A (en) * | 2016-07-04 | 2016-12-07 | 江门谦信化工发展有限公司 | The industrially prepared system of a kind of propylene glycol phenylate and preparation method |
| 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 |
| CN111269093A (en) * | 2018-12-05 | 2020-06-12 | 上海多纶化工有限公司 | Preparation method of secondary alcohol polyoxyethylene ether |
| 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 |
| CN113061243A (en) * | 2021-03-30 | 2021-07-02 | 浙江皇马科技股份有限公司 | Preparation method of allyl alcohol polyoxypropylene ether |
| WO2022206803A1 (en) * | 2021-03-30 | 2022-10-06 | 浙江皇马科技股份有限公司 | Preparation method for allyl alcohol polyoxypropylene ether |
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