CN101475478A - Method for synthesizing ethylene glycol monobutyl ether acetate - Google Patents
Method for synthesizing ethylene glycol monobutyl ether acetate Download PDFInfo
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Abstract
The invention relates to a method for synthesizing cellosolve acetate. The method comprises the steps of taking ethylene glycol butyl ether and acetic acid as raw materials and directly esterifying the raw materials at a temperature between 80 and 180 DEG C in the presence of an acidic catalyst and an azeotropic dehydrating agent so as to synthesize the cellosolve acetate. The acidic catalyst is benzene sulfonic acid or p-toluenesulfonic acid, and the amount of the catalyst accounts for 0.05 to 1 percent of the total mass of reactants. The method is characterized in that the charging molar ratio of the acetic acid to the ethylene glycol butyl ether is 1.0:0.8-1.5; the azeotropic dehydrating agent is 2-butyl acetate; and the amount of the azeotropic dehydrating agent accounts for 5 to 25 percent of the total mass of the reactants. As two-component azeotrope which is formed by the azeotropic dehydrating agent used in reaction and water is high in water content, low in water solubility and slow in hydrolysis, the method has the advantages of reducing the energy consumption for the reaction and the recovery of the azeotropic dehydrating agent, raising reaction speed and reducing loss in water.
Description
One, technical field
The present invention relates to a kind of 2-Butoxyethyl acetate synthetic method, relating in particular to a kind of is raw material with butyl glycol ether and acetic acid, under an acidic catalyst and the effect of low toxicity azeotropy dehydrant, carries out the synthetic method that the direct esterification reaction generates 2-Butoxyethyl acetate.
Two, background technology
2-Butoxyethyl acetate (EBA) is a kind of senior solvent of low toxicity of high boiling, the excellent property that contains multiple functional radical, be widely used in industries such as synthetic resins, binding agent, printing ink, printing, textile printing and dyeing and leather retanning agent, the coalescing agent that helps that also can be used as emulsion paint, multiple lacquer there is good solubility property, in multicolor finish and emulsion coatings, obtains to use widely.
The EBA synthetic method of bibliographical information mainly contains direct esterification method, ester-interchange method or by oxyethane and N-BUTYL ACETATE one-step synthesis.
The direct esterification method is the very sophisticated ester manufacture of a technology method, and its technological core is to select suitable catalyzer and azeotropy dehydrant for use, to improve activity, selectivity and the esterification yield of esterification.
The temperature of reaction of direct esterification method is directly carried out esterification at 80～170 ℃ in the presence of an acidic catalyst and azeotropy dehydrant in present technology; Acid catalyst all adopts phosphoric acid, hydrochloric acid, the vitriol oil, chlorsulfonic acid, oxalic acid, tosic acid, methylsulfonic acid etc., the domestic vitriol oil commonly used; Owing to there is water to generate in the direct esterification reaction process, carry out in order to react fully, by-product water can form azeotropic reagent with water by use and remove, and this reagent is called azeotropy dehydrant.After azeotrope was cooled, azeotropy dehydrant must be separated from water so that reclaim and recycle.Azeotropy dehydrant commonly used at present mainly contains benzene, toluene, hexanaphthene etc.The branch water effect of benzene, toluene is best, but its toxicity is big, aborning people's health is had very harmfully, easily environment is polluted; And hexanaphthene and water azeotropic point are low, cause temperature of reaction low, long reaction time, and reaction conversion ratio is low, and they are unfavorable azeotropy dehydrants.
CN1515537 has introduced the synthetic method of 1-Methoxy-2-propyl acetate, is raw material with propylene glycol monomethyl ether and acetic acid, and direct esterification synthesizing propylene glycol monomethyl ether acetate in the presence of an acidic catalyst and azeotropy dehydrant, azeotropy dehydrant are butanols or N-BUTYL ACETATE; And this azeotropy dehydrant exist form with the water binary azeotrope in water-content low, in water relatively large, the comparatively faster shortcoming of hydrolysis rate of solubleness, the azeotropy dehydrant loss is many when making reaction thus.
Three, summary of the invention
At above-mentioned shortcoming, the object of the present invention is to provide a kind of synthetic method of 2-Butoxyethyl acetate, water-content height during the azeotropy dehydrant of its use and water binary azeotrope are formed, solubleness is little and hydrolysis rate is relatively slow in water, thus the loss of azeotropy dehydrant when reducing reaction.
The technology of the present invention content is, a kind of synthetic method of 2-Butoxyethyl acetate comprises that with butyl glycol ether and acetic acid be raw material, and temperature of reaction is at 80～180 ℃, direct esterification synthesizing butyl cellosolve acetic ester in the presence of an acidic catalyst and azeotropy dehydrant; An acidic catalyst is Phenylsulfonic acid or tosic acid, and catalyst levels is 0.05～1% of a reactant total mass, it is characterized by: mole proportioning that feeds intake of acetic acid and butyl glycol ether is 1.0: 0.8～1.5; Azeotropy dehydrant is sec-butyl alcohol or 2-butyl acetate, and the azeotropy dehydrant consumption is 5～25% of a reactant total mass.
In a preferred method of the invention, suitable temperature of reaction is 120～170 ℃, and the reaction system remains at boiling state, and the water of telling to reaction only reaches stoichiometric number.
Catalyzer of the present invention adopts Phenylsulfonic acid or tosic acid, is the intermediate of phenol or p-cresol production process, ample supply of commodities on the market; Phenylsulfonic acid or tosic acid are white crystals, than sulfuric acid packing, accumulating, safe and convenient to use; Not volatile, corrodibility is lower than sulfuric acid; Be dissolved in reactant, reaction system is a homogeneous phase, the material full contact, and speed of response is fast than sulfuric acid; Overcome the deficiency of sulfuric acid strong oxidizing property, side reaction is few, the selectivity height; Develop the separating technology of catalyzer and reactant, realized the catalyst recirculation use, overcome operations such as sulfuric acid catalyst neutralization, filtration, easy and simple to handle.
The suitable consumption of catalyzer Phenylsulfonic acid or tosic acid is 0.1～0.5% of a reactant total mass, and optimum amount is 0.1～0.3% of a reactant total mass; Catalyst levels is excessive, can produce corrosion to equipment; Catalyst levels is too small, causes speed of response to slow down inevitably.
The azeotropy dehydrant that the present invention adopts is a 2-butyl acetate, and the water that forms in 2-butyl acetate and the reaction system forms azeotrope, thereby moisture is gone out.The toxicity of 2-butyl acetate is lower, and is safe in utilization; The reactant that the azeotrope that they and water form is taken out of is low, and its performance is better than toluene.
For N-BUTYL ACETATE dewatering agent reaction system, butyl glycol ether (EB) boiling point is 170.2 ℃, and the boiling point of acetic acid is 118.1 ℃, and the boiling point of product E BA is 191.5 ℃, and the boiling point of butanols is 117.7 ℃, in the time of 20 ℃ in water solubleness be 7.8% (Wt); The N-BUTYL ACETATE boiling point is 126 ℃, in the time of 20 ℃ in water solubleness be 1% (Wt), hydrolysis rate is bigger; The binary azeotrope boiling point that N-BUTYL ACETATE and water are formed is 90.2 ℃, and azeotrope is formed: water 28.7% (Wt), N-BUTYL ACETATE 71.3% (Wt).The ternary azeotrope boiling point that N-BUTYL ACETATE, butanols and water are formed is 90.7 ℃, and azeotrope is formed: water 29% (Wt), butanols 8% (Wt), N-BUTYL ACETATE 63% (Wt).
And for 2-butyl acetate dewatering agent reaction system, the EB boiling point is 170.2 ℃, and the boiling point of acetic acid is 118.1 ℃, and the boiling point of product E BA is 191.5 ℃, and the boiling point of sec-butyl alcohol is 99.5 ℃, in the time of 20 ℃ in water solubleness be 12.5% (Wt); The 2-butyl acetate boiling point is 112.3 ℃, in the time of 20 ℃ in water solubleness be 0.62% (Wt), hydrolysis rate is less; The binary azeotrope boiling point that 2-butyl acetate and water are formed is 87.45 ℃, and azeotrope is formed: water 80.5% (Wt), 2-butyl acetate 19.5% (Wt).
2-butyl acetate dewatering agent advantage: water-content height during 2-butyl acetate and water binary azeotrope are formed, so the dewatering agent consumption can suitably reduce; 2-butyl acetate binary azeotrope azeotropic point is lower than N-BUTYL ACETATE azeotrope, the reaction process less energy consumption; The 2-butyl acetate boiling point is low, reclaims less energy consumption, with the EBA convenient separation; 2-butyl acetate solubleness in water is littler than N-BUTYL ACETATE, and hydrolysis rate is also slow than N-BUTYL ACETATE, and loss is few in the water.
In process of production, can be added to sec-butyl alcohol and stoichiometric acetic acid in the reaction mixture of butyl glycol ether and acetic acid and react, the 2-butyl acetate of generation just can play the azeotropy dehydrant effect, and butyl glycol ether and acetic acid reaction are carried out smoothly.
The suitable consumption of azeotropy dehydrant is 8～18% of a reactant total mass, and optimum amount is 8～12% of a reactant total mass.The dewatering agent consumption is lower than 5% of reactant total mass, can not fully form azeotrope with reacting the water that forms, and causes dehydrating effect not good; The dewatering agent consumption is greater than 25% of the reactant total mass, and dehydrating effect can not increase, and also can cause the reactor utilization ratio to descend, and the rectifying separation energy consumption strengthens, and there is no need.
There is the possibility that is hydrolyzed to sec-butyl alcohol and acetic acid side reaction in 2-butyl acetate in reaction system.Take place in order to suppress this side reaction, need that acetic acid keeps excessive in the control reaction system, that is the mole proportioning of acetic acid and EB should be greater than 1 in the reaction system.The boiling point of acetic acid is lower slightly than EB, easily separate with product E BA, thereby excessive input is desirable.
In a preferred method of the invention, the suitable mole proportioning of acetic acid and butyl glycol ether is 1.0: 0.9～1.3, and best mole proportioning is 1.0: 1.0～1.1.Acetic acid feeds intake very few, can cause dewatering agent to decompose; Acetic acid feeds intake too much, causes equipment corrosion to increase, and the product acid number is too high; Butyl glycol ether strengthens, and can improve acetic acid conversion, helps reducing the acid number of product, but the usage ratio of equipment reduction, the rectifying load to product brings burden simultaneously, and energy consumption increases.
The present invention with the advantage that existing 2-Butoxyethyl acetate synthetic method is compared institute's tool is:
1, the toxicity of the azeotropy dehydrant of the present invention's employing is low than benzene, toluene, safe in utilization, pollutes low to production environment.
2, water-content height during the binary azeotrope of the azeotropy dehydrant of the present invention's employing and water formation is formed, so consumption can reduce.
3 compare with N-BUTYL ACETATE, and azeotropy dehydrant boiling point that the present invention adopts and the binary azeotrope azeotropic point that forms with water are all lower, less energy consumption when reaction and dewatering agent recovery.
4, to take off in water solubleness littler than N-BUTYL ACETATE for the azeotropic that adopts of the present invention, and hydrolysis rate is also slow than N-BUTYL ACETATE, makes that loss is little in the azeotropy dehydrant water.
Four, embodiment
Further describe the present invention below in conjunction with drawings and Examples, but be not limited to for embodiment.
Esterification of the present invention adopts reaction rectification technique; Butyl glycol ether, acetic acid and 2-butyl acetate azeotropy dehydrant, Phenylsulfonic acid or Catalyzed by p-Toluenesulfonic Acid agent added in the reactor that has rectifying tower, condenser and water trap react, constantly will react the moisture that generates at cat head goes out, and the 2-butyl acetate azeotropy dehydrant returns and heats up in a steamer to tower, after reaching theoretical value to drainage water, reaction finishes; Dewatering agent, unreacting material are steamed, return and recycle, the thick product of tower still is delivered to settling vessel cooling-sedimentation, overanxious, tells catalyzer and returns and recycle; Crude product is delivered to rectifying tower rectifying, can make the EBA product.
Main raw material of the present invention is technical grade, and butyl glycol ether (EB) carries out catalyzed reaction for Yida Chemical Co., Ltd. produces by oxyethane and butanols, makes by rectifying, and product purity is greater than 99.0%.Glacial acetic acid is produced for raising sub-petro-chemical corporation, and content is greater than 99.0%.
Example 1
Having water trap, returning in the 1000ml there-necked flask heat up in a steamer condenser φ 20 * 1000 packing towers and add EB360g respectively, acetic acid 277g, tosic acid 1.3g, 2-butyl acetate 96g, 120～170 ℃ of control reaction temperature keep reactant to be in boiling state all the time, reaction 5h, divide water outlet 62.4g, get thick product 629.6g, EBA content is 72.6% in the gas chromatographic analysis reaction system.Reaction mixture table composed as follows:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 0.06 | 15.0 | / | / | 11.6 | 72.6 |
Organic content and table composed as follows in the by-product water:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 94.8 | 3.8 | / | 0.9 | 0.4 | / |
Example 2
Having water trap, returning in the 1000ml there-necked flask heat up in a steamer condenser φ 20 * 1000 packing towers and add EB ether 360g respectively, acetic acid 277g, Phenylsulfonic acid 1.3g, 2-butyl acetate 51g, 120～170 ℃ of control reaction temperature keep reactant to be in boiling state all the time, reaction 5h, divide water outlet 71.2g, get thick product 606.3g, EBA content is 77.97% in the gas chromatographic analysis reaction system.Reaction mixture table composed as follows:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 0.17 | 14.6 | / | / | 5.9 | 78.0 |
Organic content and table composed as follows in the by-product water:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 87.9 | 9.6 | / | 1.4 | 0.9 | / |
Example 3
Having water trap, returning in the 1000ml there-necked flask heat up in a steamer condenser φ 20 * 1000 packing towers and add EB ether 360g respectively, acetic acid 200g, tosic acid 1.3g, 2-butyl acetate 96g, 120～170 ℃ of control reaction temperature keep reactant to be in boiling state all the time, reaction 5h, divide water outlet 54.2g, get thick product 555.8g, EBA content is 84.1% in the gas chromatographic analysis reaction system.Reaction mixture table composed as follows:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 0.1 | 3.9 | 0.1 | / | 11.3 | 84.1 |
Organic content and table composed as follows in the by-product water:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 98.1 | 0.2 | / | / | 0.3 | / |
Example 4
Having water trap, returning in the 1000ml there-necked flask heat up in a steamer condenser φ 20 * 1000 packing towers and add EB360g respectively, acetic acid 220g, tosic acid 1.3g, 2-butyl acetate 51g, 120～170 ℃ of control reaction temperature keep reactant to be in boiling state all the time, reaction 5h, divide water outlet 54.6g, get thick product 530.4g, EBA content is 78.1% in the gas chromatographic analysis reaction system.Reaction mixture table composed as follows:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 0.3 | 9.6 | 6.6 | / | 4.4 | 78.1 |
Organic content and table composed as follows in the by-product water:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 93.0 | 5.7 | / | / | 0.6 | / |
Example 5
Having water trap, returning in the 1000ml there-necked flask heat up in a steamer condenser φ 20 * 1000 packing towers and add EB360g respectively, acetic acid 185g, tosic acid 0.7g, 2-butyl acetate 96g, 120～170 ℃ of control reaction temperature keep reactant to be in boiling state all the time, reaction 5h, divide water outlet 52.5g, get thick product 553.6g, EBA content is 78.0% in the gas chromatographic analysis reaction system.Reaction mixture table composed as follows:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 0.2 | 3.1 | 4.4 | 0.4 | 10.7 | 78.0 |
Organic content and table composed as follows in the by-product water:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 96.1 | 1.9 | / | 1.1 | 0.4 | / |
Example 6
Having water trap, returning in the 1000ml there-necked flask heat up in a steamer condenser φ 20 * 1000 packing towers and add EB360g respectively, acetic acid 170g, tosic acid 1.1g, 2-butyl acetate 60g, 120～170 ℃ of control reaction temperature keep reactant to be in boiling state all the time, reaction 5h, divide water outlet 51.5g, get thick product 537.8g, EBA content is 83.65% in the gas chromatographic analysis reaction system.Reaction mixture table composed as follows:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 0.11 | 0.49 | 4.91 | 1.50 | 8.75 | 83.65 |
Organic content and table composed as follows in the by-product water:
| Form | Water | Acetic acid | EB | Sec-butyl alcohol | 2-butyl acetate | EBA |
| Content (%) | 98.49 | 0.33 | 0.04 | 0.86 | 0.28 | / |
Claims (4)
1, a kind of synthetic method of 2-Butoxyethyl acetate comprises that with butyl glycol ether and acetic acid be raw material, and temperature of reaction is at 80～180 ℃, direct esterification synthesizing butyl cellosolve acetic ester in the presence of an acidic catalyst and azeotropy dehydrant; An acidic catalyst is Phenylsulfonic acid or tosic acid, and catalyst levels is 0.05～1% of a reactant total mass, it is characterized by: mole proportioning that feeds intake of acetic acid and butyl glycol ether is 1.0:0.8～1.5; Azeotropy dehydrant is a 2-butyl acetate, and the azeotropy dehydrant consumption is 5～25% of a reactant total mass.
2, the synthetic method of a kind of 2-Butoxyethyl acetate according to claim 1, wherein temperature of reaction is 120～170 ℃.
3, the synthetic method of any 2-Butoxyethyl acetate according to claim 1 and 2, the mole proportioning that it is characterized in that acetic acid and butyl glycol ether is 1.0:0.9～1.3, the azeotropy dehydrant consumption is 8～18% of a reactant total mass.
4, the synthetic method of a kind of 2-Butoxyethyl acetate according to claim 3, the mole proportioning that it is characterized in that acetic acid and butyl glycol ether is 1.0:1.0～1.1, the azeotropy dehydrant consumption is 8～12% of a reactant total mass.
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| CN103464205A (en) * | 2013-09-26 | 2013-12-25 | 中国海洋石油总公司 | Preparation method of catalyst for synthesizing sec-butyl acetate from mixed C4 |
| CN103724195A (en) * | 2013-12-11 | 2014-04-16 | 江门谦信化工发展有限公司 | Synthetic method of ethylene glycol diacetate |
| CN105646221A (en) * | 2014-11-14 | 2016-06-08 | 辽宁奥克化学股份有限公司 | A preparing method of 2-butoxyethyl acetate |
| CN105642263A (en) * | 2014-11-14 | 2016-06-08 | 辽宁奥克化学股份有限公司 | A preparing method of a modified layered bi-metal oxide |
| CN106083578A (en) * | 2016-07-04 | 2016-11-09 | 宜兴市永加化工有限公司 | A kind of preparation method of ethylene glycol monomethyl ether acetate |
| CN106831423A (en) * | 2017-02-03 | 2017-06-13 | 荆楚理工学院 | The synthetic method of the tertiary monobutyl ether acetate of diethylene glycol (DEG) |
| CN108558661A (en) * | 2018-05-11 | 2018-09-21 | 常州大学 | A kind of propandiol butyl ether acetic acid esters synthetic method |
| CN109096066A (en) * | 2018-09-29 | 2018-12-28 | 天津科林泰克科技有限公司 | A kind of method and device removed and recycle butyl glycol ether in coating waste-water |
| CN112608234A (en) * | 2020-12-30 | 2021-04-06 | 江苏盛叶欣化工新材料有限公司 | Method for producing high-content ethylene glycol diacetate and coproducing diethylene glycol diacetate |
Family Cites Families (5)
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| US5659073A (en) * | 1995-07-07 | 1997-08-19 | Qi; Jian Steven | Process for making glycol ether acetates |
| CN1107048C (en) * | 1997-10-31 | 2003-04-30 | 国际人造丝公司 | Continuous process for the production of carboxylic acid esters of alkylene glycol monoalkyl ethers |
| CN1233614C (en) * | 2003-08-29 | 2005-12-28 | 江阴市怡达化工有限公司 | Synthesis method of propylene glyco lmethyl ether acetate |
| CN1269790C (en) * | 2004-11-18 | 2006-08-16 | 江阴市怡达化工有限公司 | Clean production method for propylene glycol monomethyl ether acetate |
| CN101337884B (en) * | 2008-08-08 | 2011-05-11 | 德纳（南京）化工有限公司 | Method for preparing 2-Butoxyethyl acetate by continuous esterification reaction |
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| CN103464205A (en) * | 2013-09-26 | 2013-12-25 | 中国海洋石油总公司 | Preparation method of catalyst for synthesizing sec-butyl acetate from mixed C4 |
| CN103724195A (en) * | 2013-12-11 | 2014-04-16 | 江门谦信化工发展有限公司 | Synthetic method of ethylene glycol diacetate |
| CN105646221A (en) * | 2014-11-14 | 2016-06-08 | 辽宁奥克化学股份有限公司 | A preparing method of 2-butoxyethyl acetate |
| CN105642263A (en) * | 2014-11-14 | 2016-06-08 | 辽宁奥克化学股份有限公司 | A preparing method of a modified layered bi-metal oxide |
| CN106083578A (en) * | 2016-07-04 | 2016-11-09 | 宜兴市永加化工有限公司 | A kind of preparation method of ethylene glycol monomethyl ether acetate |
| CN106083578B (en) * | 2016-07-04 | 2019-01-22 | 宜兴市永加化工有限公司 | A kind of preparation method of ethylene glycol monomethyl ether acetate |
| CN106831423A (en) * | 2017-02-03 | 2017-06-13 | 荆楚理工学院 | The synthetic method of the tertiary monobutyl ether acetate of diethylene glycol (DEG) |
| CN108558661A (en) * | 2018-05-11 | 2018-09-21 | 常州大学 | A kind of propandiol butyl ether acetic acid esters synthetic method |
| CN109096066A (en) * | 2018-09-29 | 2018-12-28 | 天津科林泰克科技有限公司 | A kind of method and device removed and recycle butyl glycol ether in coating waste-water |
| CN109096066B (en) * | 2018-09-29 | 2021-07-30 | 天津科林泰克科技有限公司 | Method and device for removing and recycling ethylene glycol butyl ether in coating wastewater |
| CN112608234A (en) * | 2020-12-30 | 2021-04-06 | 江苏盛叶欣化工新材料有限公司 | Method for producing high-content ethylene glycol diacetate and coproducing diethylene glycol diacetate |
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Owner name: JIANGSU YIDA CHEMICAL CO., LTD. Free format text: FORMER NAME: YIDA CHEMICAL CO., LTD. |
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| CP01 | Change in the name or title of a patent holder |
Address after: 214441, West stone bridge, No. 1, Jiangsu, Jiangyin Province Patentee after: Jiangsu Yida Chemical Co., Ltd. Patentee after: Nanjing Forestry University Address before: 214441, West stone bridge, No. 1, Jiangsu, Jiangyin Province Patentee before: Yida Chemical Co., Ltd. Patentee before: Nanjing Forestry University |