CN103193636B - A kind of method of synthesizing 2,3-butanediol ester - Google Patents
A kind of method of synthesizing 2,3-butanediol ester Download PDFInfo
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- CN103193636B CN103193636B CN201310128064.5A CN201310128064A CN103193636B CN 103193636 B CN103193636 B CN 103193636B CN 201310128064 A CN201310128064 A CN 201310128064A CN 103193636 B CN103193636 B CN 103193636B
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Abstract
The invention discloses a kind of synthetic method of 2,3-butanediol ester, it be mixed C4 hydrocarbon first through oxidative synthesis 2,3-butanediol, after separation and purification, then there is esterification further with organic acid and generate 2,3-butanediol ester in the 2,3-butanediol of synthesis.Adopt the present invention, the selectivity of 2,3-butanediol ester is high, and the reaction times is shorter, and process is simple, easily realizes.
Description
Technical field
The present invention relates to chemical field, particularly relate to a kind of method of synthesizing 2,3-butanediol ester.
Background technology
2,3-butanediol ester is the solvent of many organic compound, is also the solvent of varnish.It is widely used in the industry such as spices, essence, makeup, soap and medicine.2,3-butanediol ester generally can be obtained by 2,3-butanediol and esterifying organic acid.Wherein, the 2,3-butanediol of one of raw material obtains primarily of biological fermentation process.The method is generally first adopt conventional method to cultivate serratia marcescens, then is inoculated in substratum by bacterium seed liquor, and pass into air, stir, certain temperature bottom fermentation is cultivated 3 ~ 6 hours; Then product promotive factor-sodium acetate is supplemented, in 25 ~ 35 DEG C of fermentation culture 15 ~ 18 hours again in nutrient solution; Finally control respiratory quotient (RQ), 25 ~ 35 DEG C of fermentation culture 32 ~ 36 hours in nutrient solution, obtain the fermented liquid containing 2,3-butanediol.As patent CN1884560A serratia marcesens kind biological fermentation produces 2,3-butanediol.Therefore, there is cycle length, complex process in biological fermentation legal system 2,3-butanediol, production capacity is low, high in cost of production is not enough, cannot carry out industrialization production application, seriously hinder the development of 2,3-butanediol Lipase absobed technology.
Summary of the invention
The object of the present invention is to provide a kind of method of being synthesized 2,3-butanediol ester by mixed C4 hydrocarbon.
The object of the invention is to be achieved through the following technical solutions, a kind of method of synthesizing 2,3-butanediol ester, is characterized in that comprising the following steps:
1. alcohol, mixed C4 hydrocarbon and hydrogen peroxide are in the reactor that catalyzer is housed, mixed C4 hydrocarbon and hydrogen peroxide generation oxidizing reaction;
2. from reactor product out first through mixed C4 hydrocarbon knockout tower and alcohol knockout tower, then enter water separation column, overhead water is through process discharge, and materials at bottom of tower obtains 2,3-butanediol through refining;
3. generated 2,3-butanediol contacts in the reactor that catalyzer is housed with organic acid, esterification occurs and generates 2,3-butanediol ester.
Described alcohol, mixed C4 hydrocarbon and hydrogen peroxide mol ratio (1 ~ 40): (1 ~ 10): 1.
Described alcohol is the one in methyl alcohol, ethanol, propyl alcohol and butanols.
Described step 1. in oxidation reaction condition be: temperature of reaction: 0 DEG C ~ 200 DEG C, reaction pressure: 0.5 ~ 8.5MPa, liquid (hydrogen peroxide and alcohol) air speed 0.1 ~ 60h
-1.
The catalyzer of described step 1. in reactor is the titanium-silicon molecular sieve catalyst of aluminium sesquioxide modification.The concrete method of modifying of titanium-silicon molecular sieve catalyst is: get the A1 of 20%
2o
3both are mixed by the titanium-silicon molecular sieve catalyst with 80%, by extruded moulding, and 100 ° of C dry 4h, 500 ° of C roasting 4h.
Described step 1. in reactor can be pipeline flow reactor, or fixed-bed reactor, or slurry bed reactor, or autoclave batch reactor, or fluidized-bed reactor.
Described step 3. in organic acid be carboxylic acid.
Described carboxylic acid is the one in acetic acid, propionic acid, stearic acid, lauric acid, oleic acid, valeric acid, sad, hexanodioic acid, toxilic acid, phenylformic acid.
Described step 3. in esterification condition be: temperature of reaction: 0 DEG C ~ 200 DEG C, reaction pressure: 0 ~ 5Mpa; Liquid air speed 0.1 ~ 20h
-1; 2,3-butanediol and sour mol ratio are (0.5 ~ 5): (0.5 ~ 5).
The catalyzer of step 3. in reactor can be tosic acid, sodium hydroxide, potassium acetate, zeolite, heteropolyacid, macroporous resin, ion exchange resin, one or more in cupric chloride.
Described ester is selected from: 2,3-butanediol diacetate esters and monoacetate mixture; 2,3-butanediol dipropionate and a propionate; 2,3-butanediol SUNSOFT Q-182S and monostearate ester mixture; 2,3-butanediol dilaurate and a lauric acid ester mixture; 2,3-butanediol dioleate and monooleate mixture; 2,3-butanediol divalerate and a valerate mixture; 2,3-butanediol dicaprylate and an octanoate mixture; 2,3-butanediol adipic acid ester; 2,3-butanediol maleic acid ester; 2,3-butanediol dibenzoate and a mixtures of benzoic acid esters; 2,3-butanediol dicarboxylic acid esters and a benzoate mixtures.
Described step 3. in reactor can be pipeline flow reactor, or fixed-bed reactor, or slurry bed reactor, or autoclave batch reactor, or fluidized-bed reactor.
The present invention synthesizes 2,3-butanediol ester by mixed C4 hydrocarbon, and whole process is simple, and easily realize, 2,3-butanediol ester selectivity is up to more than 99%.
Embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated, but content not thereby limiting the invention.
Embodiment 1:
1. by the titanium-silicon molecular sieve catalyst of 15g aluminium sesquioxide modification, be loaded in fixed-bed reactor with after the dilution of 10g quartz sand.The mol ratio of methyl alcohol, hydrogen peroxide and mixed C4 hydrocarbon is 40:1:1, methyl alcohol and hydrogen peroxide enter reactor by metering infusion respectively, and mixed C4 hydrocarbon passes through gas pump injecting reactor, the titanium-silicon molecular sieve catalyst contact reacts of three kinds of reactants and modification, synthesis 2,3-butanediol.Reaction conditions: temperature of reaction 0 DEG C, reaction pressure 0.5MPa, reaction bed liquid air speed 60h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol selectivity is 40.5%, and hydrogen peroxide transformation efficiency is 99.3%;
2. 2,3-butyleneglycol separation and purification process: the product 1. obtained by step is through mixed C4 hydrocarbon knockout tower and method separation tower, and the material be separated after mixed C4 hydrocarbon and methyl alcohol enters water separation column, and overhead water is through process discharge, materials at bottom of tower obtains 2,3-butanediol through refining;
3. be the 2,3-butanediol of 0.5:1 and the mixing solutions of acetic acid by mol ratio, enter in pipeline flow reactor through volume pump, catalyzer tosic acid loadings accounts for total liquid total mass 1%.Reaction conditions: temperature of reaction 200 DEG C, reaction pressure 0.5MPa, air speed is 5.0h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol acetic ester selectivity is 99.5%, and 2,3-butanediol transformation efficiency is 83.7%, and product is 2,3-butanediol diacetate esters and monoacetate mixture.
Embodiment 2:
1. be loaded in slurry bed reactor by the titanium-silicon molecular sieve catalyst of aluminium sesquioxide modification, total liquid volume is 3 liters, and loaded catalyst accounts for 5% of total amount of liquid.Ethanol, hydrogen peroxide and mixed C4 hydrocarbon mol ratio are 40:10:1, reaction conditions: temperature of reaction 60 DEG C, reaction pressure 8.5MPa, reaction bed liquid air speed 10h
-1, other steps as embodiment 1 step 1..Products therefrom is through stratographic analysis, and 2,3-butanediol selectivity is 41.8%, and hydrogen peroxide transformation efficiency is 99.5%;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. by 20g ion-exchange resin catalyst, be loaded in fixed-bed reactor.Be after the 2,3-butanediol of 10:1 and formic acid mix by mol ratio, by volume pump injecting reactor, with ion-exchange resin catalyst contact reacts, synthesis 2,3-butanediol manthanoate.Reaction conditions: temperature of reaction 80 DEG C, reaction pressure 5MPa, reaction bed liquid air speed 20h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol manthanoate selectivity is 99.6%, and formic acid transformation efficiency is 52.4%, and product is 2,3-butanediol dicarboxylic acid esters and a benzoate mixtures.
Embodiment 3:
1. by the titanium-silicon molecular sieve catalyst of 10g aluminium sesquioxide modification, with the dilution of 20g quartz sand, be loaded in pipeline flow reactor.Reaction conditions: temperature of reaction 80 DEG C, reaction pressure 2.1MPa, the mol ratio of propyl alcohol, hydrogen peroxide and mixed C4 hydrocarbon is 1:1:1, reaction bed liquid air speed 0.1h
-1, other step with embodiment 1 step 1..Products therefrom is through stratographic analysis, and 2,3-butanediol selectivity is 39.5%, and hydrogen peroxide transformation efficiency is 99.1%;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. be loaded in slurry bed reactor by sodium hydroxide, total liquid volume is 3 liters, and loaded catalyst accounts for 5% of total amount of liquid.Reaction conditions: temperature of reaction 120 DEG C, reaction pressure 1MPa, 2,3-butanediol and propionic acid mol ratio are 2:1.Products therefrom is through stratographic analysis, and 2,3-butanediol propionic ester selectivity is 99.3%, and propionic acid rate is 71.5%, and product is 2,3-butanediol dipropionate and a propionate.
Embodiment 4:
1. the titanium-silicon molecular sieve catalyst of aluminium sesquioxide modification is loaded in fluidized-bed reactor, loaded catalyst is 25g, catalyzer 5g quartz sand dilutes, butanols and hydrogen peroxide enter reactor respectively by volume pump, and mixed C4 hydrocarbon passes through gas pump injecting reactor, with titanium-silicon molecular sieve catalyst contact reacts, the mol ratio of butanols, hydrogen peroxide and mixed C4 hydrocarbon is 1:10:1, reaction conditions: temperature of reaction 200 DEG C, reaction pressure 2.5MPa, reaction bed liquid air speed 2.4h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol selectivity is 40.5%, and hydrogen peroxide transformation efficiency is 99.4%.
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. be that 2,3-butanediol and the stearic acid mixing solutions of 0.5:1 is placed in autoclave batch reactor by mol ratio, total mass is about 100g, and catalyst acetic acid potassium loadings accounts for total liquid total mass 1%.Reaction conditions: temperature of reaction 100 DEG C, reaction pressure 0.5MPa.Products therefrom is through stratographic analysis, and 2,3-butanediol stearate selectivity is 99.4%, and 2,3-butanediol transformation efficiency is 74.8%, and product is 2,3-butanediol SUNSOFT Q-182S and monostearate ester mixture.
Embodiment 5:
1. be loaded in autoclave batch reactor by the titanium-silicon molecular sieve catalyst of aluminium sesquioxide modification, total liquid volume is 3 liters, and loaded catalyst accounts for 5% of total amount of liquid.Hydrogen peroxide and methyl alcohol add reacting initially disposable, mixed C4 hydrocarbon is by volume pump injecting reactor, reaction conditions: temperature of reaction 60 DEG C, reaction pressure 2.3MPa, the mol ratio of methyl alcohol, hydrogen peroxide and mixed C4 hydrocarbon is 14:2:1, products therefrom through stratographic analysis, 2,3-butyleneglycol selectivity is 41.8%, and hydrogen peroxide transformation efficiency is 99.7%.
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. be that 2,3-butanediol and the benzoic mixing solutions of 1:1 is placed in autoclave batch reactor by mol ratio, total mass is about 100g, and catalyzer accounts for total liquid total mass 1% to cupric chloride loadings.Reaction conditions: temperature of reaction 90 DEG C, reaction pressure 0.5MPa, products therefrom is through stratographic analysis, 2,3-butanediol benzoic ether selectivity is 99.5%, 2,3-butyleneglycol transformation efficiency is 56.7%, and product is 2,3-butanediol dibenzoate and a mixtures of benzoic acid esters.
Embodiment 6:
1. as the step in any embodiment 1 ~ embodiment 5 1.;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. by 20g zeolite catalyst, be loaded in fixed-bed reactor.Be after the 2,3-butanediol of 0.5:1 and lauric acid mix by mol ratio, by volume pump injecting reactor, with zeolite catalyst contact reacts, synthesis 2,3-butanediol laurate.Reaction conditions: temperature of reaction 90 DEG C, reaction pressure 0.5MPa, reaction bed liquid air speed 0.1h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol laurate selectivity is 99.8%, and 2,3-butanediol transformation efficiency is 88.9%, and product is 2,3-butanediol dilaurate and a lauric acid ester mixture.
Embodiment 7:
1. as the step in any embodiment 1 ~ embodiment 5 1.;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. by 20g macroporous resin catalyzer, be loaded in fixed-bed reactor.Be after the 2,3-butanediol of 1:10 and oleic acid mix by mol ratio, by volume pump injecting reactor, with ion-exchange resin catalyst contact reacts, synthesis 2,3-butanediol oleic acid ester reaction conditions: temperature of reaction 80 DEG C, reaction pressure 0MPa, reaction bed liquid air speed 2.5h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol oleic acid ester selectivity is 99.7%, and 2,3-butanediol transformation efficiency is 89.7%, and product is 2,3-butanediol dioleate and monooleate mixture.
Embodiment 8:
1. as the step in any embodiment 1 ~ embodiment 5 1.;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. by 20g heteropolyacid catalyst, be loaded in fixed-bed reactor.Be after the 2,3-butanediol of 1:3 and valeric acid mix by mol ratio, by volume pump injecting reactor, with heteropolyacid catalyst contact reacts, synthesis 2,3-butanediol valerate.Reaction conditions: temperature of reaction 95 DEG C, reaction pressure 0MPa, reaction bed liquid air speed 3h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol valerate selectivity is 99.3%, and 2,3-butanediol transformation efficiency is 77.4%, and product is 2,3-butanediol divalerate and a valerate mixture.
Embodiment 9:
1. as the step in any embodiment 1 ~ embodiment 5 1.;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. by 20g ion-exchange resin catalyst, be loaded in fixed-bed reactor.By mol ratio be 1:2 2,3-butanediol and sad mix after, by volume pump injecting reactor, with ion-exchange resin catalyst contact reacts, synthesis 2,3-butanediol octanoate.Reaction conditions: temperature of reaction 100 DEG C, reaction pressure 0MPa, reaction bed liquid air speed 2.7h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol octanoate selectivity is 99.8%, and 2,3-butanediol transformation efficiency is 63.4%, and product is 2,3-butanediol dicaprylate and an octanoate mixture.
Embodiment 10:
1. as the step in any embodiment 1 ~ embodiment 5 1.;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. by 20g ion-exchange resin catalyst, be loaded in fixed-bed reactor.Be after the 2,3-butanediol of 1:2 and hexanodioic acid mix by mol ratio, by volume pump injecting reactor, with ion-exchange resin catalyst contact reacts, synthesis 2,3-butanediol adipic acid ester.Reaction conditions: temperature of reaction 90 DEG C, reaction pressure 0MPa, reaction bed liquid air speed 2.0h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol adipic acid ester selectivity is 99.7%, and 2,3-butanediol transformation efficiency is 59.3%, and product is 2,3-butanediol two adipic acid ester.
Embodiment 11:
1. as the step in any embodiment 1 ~ embodiment 5 1.;
2. 2,3-butanediol separation and purification process as embodiment 1 step 2.;
3. by 20g ion-exchange resin catalyst, be loaded in fixed-bed reactor.Be after the 2,3-butanediol of 1:4 and toxilic acid mix by mol ratio, by volume pump injecting reactor, with ion-exchange resin catalyst contact reacts, synthesis 2,3-butanediol maleic acid ester.Reaction conditions: temperature of reaction 95 DEG C, reaction pressure 0MPa, reaction bed liquid air speed 1.8h
-1.Products therefrom is through stratographic analysis, and 2,3-butanediol maleic acid ester selectivity is 99.5%, and 2,3-butanediol transformation efficiency is 81.2%, and product is 2,3-butanediol maleic acid ester.
Claims (8)
1. synthesize a method for 2,3-butanediol ester, it is characterized in that:
1. mol ratio (1 ~ 40): (1 ~ 10): alcohol, the mixed C4 hydrocarbon of 1 contact in the reactor that catalyzer is housed with hydrogen peroxide, mixed C4 hydrocarbon and hydrogen peroxide generation oxidizing reaction; Described reaction conditions is: temperature of reaction: 0 DEG C ~ 200 DEG C, reaction pressure: 0.5 ~ 8.5MPa, liquid air speed 0.1 ~ 60h
-1; Described catalyzer is the titanium-silicon molecular sieve catalyst of alumina carrier modification, and the concrete preparation method of catalyzer is: get the A1 of 20%
2o
3both are mixed by the titanium-silicon molecular sieve catalyst with 80%, by extruded moulding, and 100 DEG C of dry 4h, 500 DEG C of roasting 4h;
2. from reactor product out first through mixed C4 hydrocarbon knockout tower and alcohol knockout tower, then enter water separation column, overhead water is through process discharge, and materials at bottom of tower obtains 2,3-butanediol through refining;
3. mol ratio (0.5 ~ 5): the 2,3-butanediol of (0.5 ~ 5) contacts in the esterifier that catalyzer is housed with organic acid, esterification occurs and generates 2,3-butanediol ester, reaction conditions is temperature: between 0 ~ 200 DEG C, reaction pressure: 0 ~ 5Mpa; Liquid air speed 0.1 ~ 20h
-1.
2. method according to claim 1, is characterized in that: described alcohol is the one in methyl alcohol, ethanol, propyl alcohol and butanols.
3. method according to claim 1, is characterized in that: described mixed C4 hydrocarbon refers to from the mixed C4 hydrocarbon of refinery, for the production of the mixed C4 hydrocarbon after polyisobutene, for the production of one or more in the mixed C4 hydrocarbon after methyl tertiary butyl ether.
4. method according to claim 1, is characterized in that: described reactor 1. can be pipeline flow reactor, or fixed-bed reactor, or slurry bed reactor, or autoclave batch reactor, or fluidized-bed reactor.
5. method according to claim 1, is characterized in that: described organic acid is carboxylic acid.
6. method according to claim 5, is characterized in that: described carboxylic acid is the one in acetic acid, propionic acid, stearic acid, lauric acid, oleic acid, valeric acid, sad, hexanodioic acid, toxilic acid, phenylformic acid.
7. method according to claim 1, wherein catalyzer is 3. tosic acid, sodium hydroxide, potassium acetate, zeolite, heteropolyacid, macroporous resin, ion exchange resin, one or more in cupric chloride.
8. method according to claim 1, is characterized in that: described esterifier is pipeline flow reactor, or fixed-bed reactor, or slurry bed reactor, or autoclave batch reactor.
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| CN103980116A (en) * | 2014-05-23 | 2014-08-13 | 山东联创节能新材料股份有限公司 | 2,3-butanediol ester and preparation method thereof |
| CN105177068A (en) * | 2015-09-04 | 2015-12-23 | 中国石油大学(华东) | Method for synthesizing 2,3-butanediol pentanoate through lipase catalysis |
| CN106831412A (en) * | 2017-01-16 | 2017-06-13 | 南京工业大学 | Preparation method of butanediol fatty acid ester and application of butanediol fatty acid ester as gel factor |
| CN111138286A (en) * | 2018-11-01 | 2020-05-12 | 上海凯赛生物技术股份有限公司 | Method for treating mixture containing long-chain dibasic acid |
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| CN101279897A (en) * | 2008-05-21 | 2008-10-08 | 湖南长岭石化科技开发有限公司 | Method for synthesizing butanediol ethere |
| CN101328158A (en) * | 2008-07-26 | 2008-12-24 | 湖南长岭石化科技开发有限公司 | Method for synthesizing butyl oxide linkage |
| CN102453241A (en) * | 2011-05-09 | 2012-05-16 | 上海聚友化工有限公司 | Preparation method of poly (2, 3-butylene terephthalate) |
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| CN100554231C (en) * | 2007-09-14 | 2009-10-28 | 胡先念 | The method for preparing butyl glycol ether |
| EP2483232B1 (en) * | 2009-09-29 | 2013-05-29 | Shell Internationale Research Maatschappij B.V. | Process for preparing alkanediol and dialkyl carbonate |
| DE102009048775A1 (en) * | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Process for the preparation of polyol esters |
| CN102951998B (en) * | 2011-08-24 | 2015-07-01 | 岳阳蓬诚科技发展有限公司 | Method of preparing glycol by using one-step ethylene method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101279897A (en) * | 2008-05-21 | 2008-10-08 | 湖南长岭石化科技开发有限公司 | Method for synthesizing butanediol ethere |
| CN101328158A (en) * | 2008-07-26 | 2008-12-24 | 湖南长岭石化科技开发有限公司 | Method for synthesizing butyl oxide linkage |
| CN102453241A (en) * | 2011-05-09 | 2012-05-16 | 上海聚友化工有限公司 | Preparation method of poly (2, 3-butylene terephthalate) |
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Address after: 414012 Lu Kou Zhen Chang Lian Long Kou, Yunxi District, Yueyang City, Hunan Province (opposite to Chang Lian hospital) Patentee after: Hunan Changlian New Material Technology Co.,Ltd. Address before: 414012 Yunxi District, Hunan City, Yueyang Province, Changling Patentee before: HUNAN CHANGLING PETROCHEMICAL TECHNOLOGY DEVELOPMENT Co.,Ltd. |