CN101337864A - Method for preparing ethylene glycol mono-n-butyl ether by continuous pipe reaction - Google Patents
Method for preparing ethylene glycol mono-n-butyl ether by continuous pipe reaction Download PDFInfo
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- CN101337864A CN101337864A CNA2008100216284A CN200810021628A CN101337864A CN 101337864 A CN101337864 A CN 101337864A CN A2008100216284 A CNA2008100216284 A CN A2008100216284A CN 200810021628 A CN200810021628 A CN 200810021628A CN 101337864 A CN101337864 A CN 101337864A
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Abstract
The invention relates to a method for preparing glycol mono-n-butyl ether by continuous channel reaction, which comprises the following steps: mixing n-butyl alcohol, ethylene oxide and alkyl sulfonate serving as a catalyst, preheating, continuously feeding into a channel reactor, carrying out etherification reaction at a reaction temperature of 130 to 220 DEG C and under a pressure of 3.5 to 6.0 MPa, and rectifying the reaction result to recover the excessive n-butyl alcohol and obtain the glycol mono-n-butyl ether. According to the method, the conversion rate of the ethylene oxide is 100%, and the selectivity of the glycol mono-n-butyl ether is 85 to 94%. The continuous channel reaction process can improve the production efficiency of the glycol mono-n-butyl ether, and has excellent large-scale industrial application prospect.
Description
Technical field
The present invention relates to a kind of preparation method of ethylene glycol mono-n-butyl ether, especially be particularly related to a kind of method of preparing ethylene glycol mono-n-butyl ether by continuous pipe reaction.
Background technology
The glycol ether of using as solvent is a maximum with the consumption of ethylene glycol mono-n-butyl ether and acetic ester thereof.It is good dispersity in water, extensive application in water-based paint.In addition, it also is the fine solvent of Nitrocellulose, Synolac and resol etc.Because its vaporator rate is slower, thus to the gloss that improves varnish, prevent that decortication etc. from effectively, making thinner in sharp paint and enamel paint, can increase paint and timber, intermetallic adhesivity.
Propyl carbinol and oxyethane (EO) etherification reaction is to prepare ethylene glycol mono-n-butyl ether method commonly used, adopts liquid acid (as BF usually
3Etherate) catalyzer or liquid base are (as N
aOH, KOH etc.) catalyzer.Though liquid acid has very high catalytic activity, catalyzer is strong to equipment corrosion, and polluted product and environment.Liquid base catalysis propyl carbinol and oxyethane (EO) etherification reaction prepares ethylene glycol mono-n-butyl ether, has that by product is many, the defective of poor selectivity.Hu Xiannians etc. (Chinese patent application number 200710035742.8) are in the presence of HTS or modifying titanium-silicon molecular sieve, by ethene, hydrogen peroxide and propyl carbinol synthesizing glycol mono-n-butyl ether, this invention single step reaction prepares butyl glycol ether, make ethene, hydrogen peroxide, propyl carbinol in the presence of HTS or modifying titanium-silicon molecular sieve, propyl carbinol and hydrogen peroxide according to 1～20 mol ratio, 5～280 ℃ with 0.1～5.0MPa under contact 0.2～10 hour, in every gram reaction solution 0.001～0.5g molecular sieve is arranged.Adopt report (the hair Lianshan Mountain etc. of novel solid acids catalyzer in addition; chemical industry and engineering: natural science edition; the 27th the 3rd phase of volume of June in 2006); use novel solid acids catalyzer to carry out the etherification reaction of propyl carbinol and oxyethane; prepare ethylene glycol mono-n-butyl ether; but, be difficult to enhance productivity and implement scale production because employing is batch still formula reaction process.
The object of the invention is can overcome existing production technique shortcoming for the preparation ethylene glycol mono-n-butyl ether provides a kind of, and the novel process of energy serialization high efficiency production.
Summary of the invention
The object of the present invention is to provide a kind of method of preparing ethylene glycol mono-n-butyl ether by continuous pipe reaction, overcome the defective that the existing complex technical process of batch still formula reaction process, plant factor are low, be difficult to enhance productivity, adopt continuous pipe reaction, to improve the production efficiency of ethylene glycol mono-n-butyl ether, and catalyst activity height, selectivity are good, the product yield height.
The technical solution used in the present invention is as follows:
A kind of method of preparing ethylene glycol mono-n-butyl ether by continuous pipe reaction, with propyl carbinol and oxyethane is raw material, it is characterized in that: be catalyzer with the alkylsulfonate, with propyl carbinol, oxyethane and catalyzer through mix, after the preheating, the input channel reactor carries out etherification reaction continuously, and temperature of reaction 130-220 ℃, pressure 3.5～6.0MPa, reaction product reclaims excessive propyl carbinol through rectifying, makes ethylene glycol mono-n-butyl ether.
It is the catalyzer of etherification reaction that the present invention adopts alkylsulfonate, and the catalytic activity height of this catalyzer, selectivity is good, product yield is high, nontoxic, nonirritant, equipment is not had corrosion.Described alkylsulfonate catalyzer comprises trifluoromethane sulfonic acid aluminium, trifluoromethane sulfonic acid magnesium, trifluoromethane sulfonic acid zinc, methyl disulfonic acid zinc, methyl disulfonic acid aluminium or methyl disulfonic acid magnesium, or its mixture, catalyst consumption is the 0.02-0.1% of propyl carbinol quality, and preferred catalyst levels is the 0.03-0.05% of propyl carbinol quality.
Propyl carbinol and oxyethane mix the back at pipeline reactor generation etherification reaction, and the reaction raw materials proportioning is that the mol ratio of propyl carbinol and oxyethane is propyl carbinol: oxyethane=3-9: 1 (mol ratio), preferred 5-6: 1 (mol ratio).
Etherification reaction temperature 130-220 ℃, preferable reaction temperature is 140-170 ℃.The method of control reaction temperature can adopt carries out adiabatic reaction or isothermal reaction in pipeline reactor, or the mode of part isothermal reaction and part adiabatic reaction combination, the method of preferred part isothermal reaction and part adiabatic reaction combination, so that temperature of reaction is controlled in the described temperature range, particularly be controlled in the preferable reaction temperature 140-170 ℃ scope.
Working pressure 3.5～6.0MPa in the pipeline reactor, preferred operations pressure 4.0～5.0MPa.
The etherification reaction time, promptly the residence time is 1-3h in the pipeline reactor, and preferably controlling reaction time is 2.0-2.5h.
The method of continuous conduit formula prepared in reaction ethylene glycol mono-n-butyl ether of the present invention, a kind of specific implementation method of Cai Yonging is in an embodiment, earlier catalyzer is formulated in the raw material propyl carbinol by institute's expense, being furnished with the propyl carbinol and the oxyethane of catalyzer is carried by certain mole proportioning by volume pump respectively, mix through static mixer, and, send into pipeline reactor continuously through after the preheating, the pipeline reactor outlet is provided with pressure regulator valve controlling reactor working pressure.As indicated above, pipeline reactor can carry out etherification reaction under adiabatic reaction, isothermal reaction or part isothermal reaction and three kinds of conditions of part adiabatic reaction combination.The reaction for preparing ethylene glycol mono-n-butyl ether in view of propyl carbinol and ethylene oxide etherification is thermopositive reaction, when adopting the adiabatic reaction method, only needs the pipeline reactor outer wall is got final product with the lagging material insulation; When thermal reaction methods such as employing, pipeline reactor can be placed oil bath, the thermal oil in the oil bath is furnished with the temperature control regulation system, and the thermal oil in the oil bath can effectively be removed the reaction heat of emitting in the pipeline reactor, reaches the effect of isothermal reaction; When adopting the part isothermal reaction with method that the part adiabatic reaction combines, then the section of tubing reactor is placed above-mentioned oil bath, section of tubing reactor outer wall is incubated with lagging material.Adopt adiabatic reaction method equipment simpler relatively, but because exothermic heat of reaction can cause temperature rising in the reactor, and under higher reaction temperatures, the selectivity of ethylene glycol mono-n-butyl ether decreases.Employing waits thermal reaction method equipment relatively complicated, but effective control reaction temperature easily is controlled at temperature of reaction in the preferred 140-170 ℃ scope, and the selectivity of ethylene glycol mono-n-butyl ether is higher.The method that adopts the part isothermal reaction to combine with the part adiabatic reaction both can reduce equipment complexity relatively, can obtain the selectivity of higher ethylene glycol mono-n-butyl ether again.
The discharging of pipeline reactor, promptly the product of etherification reaction mainly comprises excessive propyl carbinol, ethylene glycol mono-n-butyl ether and trace catalyst and by product.Reaction product is carried out rectifying, reclaim excessive propyl carbinol, obtain ethylene glycol mono-n-butyl ether (crude product).Resulting ethylene glycol mono-n-butyl ether (crude product) can also further adopt rectificating method to purify.In an embodiment, the discharging of pipeline reactor removes excessive propyl carbinol and reclaim through taking off the butanols tower, and bottom product is delivered to the rectifying of product rectifying tower, obtains the butyl glycol ether product.The propyl carbinol that reclaims can be used as reaction raw materials and recycles.
The preparation method of ethylene glycol mono-n-butyl ether of the present invention adopts continuous pipe reaction, and catalyst activity height, nontoxic no burn into selectivity are good, and operating method is simple, has improved the production efficiency of ethylene glycol mono-n-butyl ether, reduces its production cost.The inventive method product yield height, selectivity are good, and the transformation efficiency of oxyethane is 100%, the selectivity of ethylene glycol mono-n-butyl ether is 85-94%, has splendid large-scale industrial application prospect.
Describe the present invention below in conjunction with embodiment.Scope of the present invention is not exceeded with embodiment, but is limited by the scope of claim.
Embodiment
Embodiment 1
Adopt the adiabatic reaction method.Pipeline reactor adopts external diameter 8mm, wall thickness 1mm, and the stainless steel tube of long 180m, the pipeline reactor outer wall is incubated with lagging material, reactor volume 5L.Catalyzer methyl disulfonic acid zinc is formulated in the raw material propyl carbinol by 0.04% of butanols quality, the propyl carbinol of being furnished with catalyzer methyl disulfonic acid zinc is with measuring pump delivery, dominant discharge 2.26L/h, oxyethane is carried with another volume pump, dominant discharge 0.24L/h, propyl carbinol and the oxyethane carried by two volume pumps mix through static mixer, and the process preheater is preheated to 140 ℃ with reaction raw materials, send into pipeline reactor continuously, the pressure regulator valve red-tape operati pressure 5.0MPa that the pipeline reactor outlet is provided with.Reaction raw materials proportioning propyl carbinol in the above-mentioned technology: oxyethane is 6: 1 (mol ratio), and reaction time is 2h.Because exothermic heat of reaction causes the hot(test)-spot temperature in the reactor to reach 210 ℃.The transformation efficiency of reaction result oxyethane is 100%, the selectivity 86.8% of ethylene glycol mono-n-butyl ether.The reaction discharging recycles excessive Butanol Recycling through taking off the butanols tower, and bottom product is delivered to the rectifying of product rectifying tower, obtains the ethylene glycol mono-n-butyl ether product.
Embodiment 2
Adopt the isothermal reaction method.Pipeline reactor adopts external diameter 8mm, wall thickness 1mm, the stainless steel tube of long 180m, reactor volume 5L.Pipeline reactor is placed oil bath, and the thermal oil in the oil bath is furnished with the temperature control regulation system, and the thermal oil in the oil bath can effectively be removed the reaction heat of emitting in the pipeline reactor, reaches the effect of isothermal reaction.Catalyzer adopts the mixture of trifluoromethane sulfonic acid aluminium and methyl disulfonic acid zinc, catalyzer trifluoromethane sulfonic acid aluminium and methyl disulfonic acid zinc are formulated in the raw material propyl carbinol by 0.01% and 0.02% of butanols quality respectively, the propyl carbinol of being furnished with catalyzer trifluoromethane sulfonic acid aluminium and methyl disulfonic acid zinc mixture is with measuring pump delivery, dominant discharge 1.85L/h, oxyethane is carried with another volume pump, dominant discharge 0.15L/h, propyl carbinol and the oxyethane carried by two volume pumps mix through static mixer, and the process preheater is preheated to 150 ℃ with reaction raw materials, send into pipeline reactor continuously, the pressure regulator valve red-tape operati pressure 4.5MPa that the pipeline reactor outlet is provided with.Reaction raw materials proportioning propyl carbinol in the above-mentioned technology: oxyethane is 7: 1 (mol ratio), and reaction time is 2.5h.160 ℃ of control thermal oil temperature, because the reaction liberated heat is removed by thermal oil, the hot(test)-spot temperature in the reactor is 165 ℃.The transformation efficiency of reaction result oxyethane is 100%, the selectivity 92.5% of ethylene glycol mono-n-butyl ether.The reaction discharging recycles excessive Butanol Recycling through taking off the butanols tower, and bottom product is delivered to the rectifying of product rectifying tower, obtains the ethylene glycol mono-n-butyl ether product.
Embodiment 3
The method that adopts the part isothermal reaction to combine with the part adiabatic reaction.Pipeline reactor adopts external diameter 8mm, wall thickness 1mm, the stainless steel tube of long 180m, reactor volume 5L.The stainless steel tube of long 30m is placed oil bath, and the thermal oil in the oil bath is furnished with the temperature control regulation system, and the thermal oil in the oil bath can effectively be removed the reaction heat of emitting in the pipeline reactor, reaches the effect of part isothermal reaction.The stainless steel tube outer wall of long 150m is incubated with lagging material, catalyzer adopts trifluoromethane sulfonic acid aluminium, catalyzer trifluoromethane sulfonic acid aluminium is formulated in the raw material propyl carbinol by 0.03% of butanols quality, the propyl carbinol of being furnished with catalyzer trifluoromethane sulfonic acid aluminium is with measuring pump delivery, dominant discharge 2.26L/h, oxyethane is carried with another volume pump, dominant discharge 0.24L/h, propyl carbinol and the oxyethane carried by two volume pumps mix through static mixer, and the process preheater is preheated to 150 ℃ with reaction raw materials, send into pipeline reactor continuously, the pressure regulator valve red-tape operati pressure 4.5MPa that the pipeline reactor outlet is provided with.Reaction raw materials proportioning propyl carbinol in the above-mentioned technology: oxyethane is 6: 1 (mol ratio), and reaction time is 2h (wherein the isothermal reaction partial reaction residence time is 20min, and exhausted warm reactive moieties reaction time is 100min).Isothermal reaction is partly controlled 160 ℃ of thermal oil temperature, because the concentration of oxyethane is higher relatively in the preceding 20min reaction process, the reaction impellent is big, speed of response is fast, most of exothermic heat of reaction amount is removed by thermal oil, make exhausted temperature reactive moieties not produce obvious temperature rise, the hot(test)-spot temperature in the reactor is 170 ℃.The transformation efficiency of reaction result oxyethane is 100%, the selectivity 90.2% of ethylene glycol mono-n-butyl ether.The reaction discharging recycles excessive Butanol Recycling through taking off the butanols tower, and bottom product is delivered to the rectifying of product rectifying tower, obtains the ethylene glycol mono-n-butyl ether product.
Embodiment 4
The method that adopts the part isothermal reaction to combine with the part adiabatic reaction.Pipeline reactor adopts external diameter 8mm, wall thickness 1mm, the stainless steel tube of long 180m, reactor volume 5L.The stainless steel tube of long 30m is placed oil bath, and the thermal oil in the oil bath is furnished with the temperature control regulation system, and the thermal oil in the oil bath can effectively be removed the reaction heat of emitting in the pipeline reactor, reaches the effect of part isothermal reaction.The stainless steel tube outer wall of long 150m is incubated with lagging material, catalyzer adopts the mixture of trifluoromethane sulfonic acid zinc and methyl disulfonic acid zinc, catalyzer trifluoromethane sulfonic acid zinc and methyl disulfonic acid zinc are formulated in the raw material propyl carbinol by 0.02% and 0.01% of butanols quality respectively, the propyl carbinol of being furnished with catalyzer trifluoromethane sulfonic acid zinc and methyl disulfonic acid zinc mixture is with measuring pump delivery, dominant discharge 2.34L/h, oxyethane is carried with another volume pump, dominant discharge 0.16L/h, propyl carbinol and the oxyethane carried by two volume pumps mix through static mixer, and the process preheater is preheated to 150 ℃ with reaction raw materials, send into pipeline reactor continuously, the pressure regulator valve red-tape operati pressure 4.5MPa that the pipeline reactor outlet is provided with.Reaction raw materials proportioning propyl carbinol in the above-mentioned technology: oxyethane is 8: 1 (mol ratio), and reaction time is 2h (wherein the isothermal reaction partial reaction residence time is 20min, and exhausted warm reactive moieties reaction time is 100min).Isothermal reaction is partly controlled 160 ℃ of thermal oil temperature, because the concentration of oxyethane is higher relatively in the preceding 20min reaction process, the reaction impellent is big, speed of response is fast, most of exothermic heat of reaction amount is removed by thermal oil, and the mol ratio of propyl carbinol and oxyethane is bigger, and exhausted warm reactive moieties does not produce obvious temperature rise, and the hot(test)-spot temperature in the reactor is 166 ℃.The transformation efficiency of reaction result oxyethane is 100%, the selectivity 93.2% of ethylene glycol mono-n-butyl ether.The reaction discharging is through taking off the butanols tower with excessive propyl carbinol recycling use, and bottom product is delivered to the rectifying of product rectifying tower, obtains the ethylene glycol mono-n-butyl ether product.
Claims (9)
1, a kind of method of preparing ethylene glycol mono-n-butyl ether by continuous pipe reaction, with propyl carbinol and oxyethane is raw material, it is characterized in that: be catalyzer with the alkylsulfonate, with propyl carbinol, oxyethane and catalyzer through mix, after the preheating, the input channel reactor carries out etherification reaction continuously, and temperature of reaction 130-220 ℃, pressure 3.5～6.0MPa, reaction product reclaims excessive propyl carbinol through rectifying, makes ethylene glycol mono-n-butyl ether.
2, the method for preparing ethylene glycol mono-n-butyl ether according to claim 1, it is characterized in that: described alkylsulphonic acid salt catalyst is selected from one or more in trifluoromethane sulfonic acid aluminium, trifluoromethane sulfonic acid magnesium, trifluoromethane sulfonic acid zinc, methyl disulfonic acid zinc, methyl disulfonic acid aluminium or the methyl disulfonic acid magnesium, and catalyst consumption is the 0.02-0.1% of propyl carbinol quality.
3, the method for preparing ethylene glycol mono-n-butyl ether according to claim 1 is characterized in that: the mol ratio of described propyl carbinol and oxyethane is propyl carbinol: oxyethane=3-9: 1.
4, the method for preparing ethylene glycol mono-n-butyl ether according to claim 3 is characterized in that: the mol ratio of described propyl carbinol and oxyethane is propyl carbinol: oxyethane=5-6: 1.
5, the method for preparing ethylene glycol mono-n-butyl ether according to claim 1 is characterized in that: described temperature of reaction is 140-170 ℃.
6, prepare the method for ethylene glycol mono-n-butyl ether according to claim 1 or 5, it is characterized in that: in described pipeline reactor, carry out adiabatic reaction or isothermal reaction, or partly carrying out isothermal reaction partly carries out adiabatic reaction.
7, the method for preparing ethylene glycol mono-n-butyl ether according to claim 1 is characterized in that: described pressure is 4.0～5.0MPa.
8, the method for preparing ethylene glycol mono-n-butyl ether according to claim 1 is characterized in that: the time of described etherification reaction is 1-3h.
9, the method for preparing ethylene glycol mono-n-butyl ether according to claim 1 is characterized in that: the ethylene glycol mono-n-butyl ether that makes adopts rectificating method to purify.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101921180A (en) * | 2010-08-12 | 2010-12-22 | 江苏怡达化工有限公司 | Method for synthesizing butyl cellosolve |
| CN104788294A (en) * | 2015-04-24 | 2015-07-22 | 天津普莱化工技术有限公司 | Device and processing method for synthesis of ethylene glycol monobutyl ether through reactive distillation |
| CN106946663A (en) * | 2017-04-06 | 2017-07-14 | 广州印田新材料有限公司 | Epoxide one-step method prepares the synthetic method of alcohol ether |
| CN111747828A (en) * | 2020-07-23 | 2020-10-09 | 浙江皇马科技股份有限公司 | Preparation method and system of ethylene glycol monopropyl ether |
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2008
- 2008-08-08 CN CN2008100216284A patent/CN101337864B/en active Active
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101921180A (en) * | 2010-08-12 | 2010-12-22 | 江苏怡达化工有限公司 | Method for synthesizing butyl cellosolve |
| CN101921180B (en) * | 2010-08-12 | 2013-08-28 | 江苏怡达化学股份有限公司 | Method for synthesizing butyl cellosolve |
| CN104788294A (en) * | 2015-04-24 | 2015-07-22 | 天津普莱化工技术有限公司 | Device and processing method for synthesis of ethylene glycol monobutyl ether through reactive distillation |
| CN104788294B (en) * | 2015-04-24 | 2016-07-13 | 天津普莱化工技术有限公司 | The device of a kind of reactive distillation synthesizing glycol monobutyl ether and process |
| CN106946663A (en) * | 2017-04-06 | 2017-07-14 | 广州印田新材料有限公司 | Epoxide one-step method prepares the synthetic method of alcohol ether |
| CN111747828A (en) * | 2020-07-23 | 2020-10-09 | 浙江皇马科技股份有限公司 | Preparation method and system of ethylene glycol monopropyl ether |
| WO2022017286A1 (en) * | 2020-07-23 | 2022-01-27 | 浙江皇马科技股份有限公司 | Preparation method and system for ethylene glycol monopropyl ether |
| CN111747828B (en) * | 2020-07-23 | 2023-05-26 | 浙江皇马科技股份有限公司 | Preparation method and system of ethylene glycol monopropyl ether |
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Address after: 210047 Nanjing Chemical Industrial Park, Jiangsu, Nanjing, No. Patentee after: Jiangsu Dena chemical Limited by Share Ltd Address before: 210047 Nanjing Chemical Industrial Park, Jiangsu, Nanjing, No. Patentee before: Dana (Nanjing) Chemical Co. Ltd. |
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