CN102992956A - Preparation method of 2-butyl alcohol - Google Patents
Preparation method of 2-butyl alcohol Download PDFInfo
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- CN102992956A CN102992956A CN2011102684401A CN201110268440A CN102992956A CN 102992956 A CN102992956 A CN 102992956A CN 2011102684401 A CN2011102684401 A CN 2011102684401A CN 201110268440 A CN201110268440 A CN 201110268440A CN 102992956 A CN102992956 A CN 102992956A
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Abstract
The invention relates to a preparation method of 2-butyl alcohol. The method comprises the following steps: carrying out an ester exchange reaction of 2-butyl acetate and low-carbon alcohol in a catalytic rectifying tower in the presence of an ester exchange catalyst, and collecting the 2-butyl alcohol from tower bottoms, wherein the low-carbon alcohol is C1-C3 alcohol. The method has the advantages of high 2-butyl acetate conversion rate and high 2-butyl alcohol selectivity.
Description
Technical field
The present invention relates to a kind of preparation method of sec-butyl alcohol.
Background technology
Sec-butyl alcohol (SBA) as solvent, can be used as the component that improves gasoline octane rating industrial, can be used for producing softening agent, dressing agent, weedicide, secondary butyl ester etc., also can be used for producing methylethylketone and (claims again butanone, MEK).
At present, the method for industrial production sec-butyl alcohol mainly is the n-butylene hydration method, mainly comprises with sulfuric acid as the indirect hydration method of catalyzer and the two kinds of techniques of direct hydration method take ion exchange resin or heteropolyacid as catalyzer.
The indirect hydrating process technology maturation of sulfuric acid process, not harsh to the purity requirement of raw material n-butene, reaction conditions is relatively gentleer, and technique is simple, and is easy to control.Yet the weak point of this technique is to produce a large amount of diluted acids in the production process, and equipment corrosion is serious, and the three wastes are more, and plant investment is larger.
The technical process of resin method direct hydration is simple, and the product purification and recover is easy, and the three wastes are few, and are little to equipment corrosion, and the sec-butyl alcohol selectivity is high.Yet the weak point of this technique is that the starting material n-butene is had relatively high expectations, and n-butene content is higher than 90% in the general requirement C 4 fraction; And the resin catalyst resistance to elevated temperatures is relatively poor, and the life-span is short, easy inactivation, n-butene per pass conversion lower (being generally below 10%).
The technical process of heteropolyacid method direct hydration is simple, catalyst performance stabilised, and the life-span is long, reacts to be the gas and liquid phase reaction, and reactor efficiency is higher, does not high boiling point by-products producedly accumulate in reactor.Yet the weak point of this technique is that the n-butene per pass conversion is low, and reaction needs to carry out under high pressure and comparatively high temps.
Summary of the invention
The objective of the invention is the defects for the technique existence that overcomes existing preparation sec-butyl alcohol, a kind of method for preparing sec-butyl alcohol is provided.
The invention provides a kind of preparation method of sec-butyl alcohol, the method comprises: in the presence of transesterification catalyst, sec-butyl acetate and low-carbon alcohol be added to carry out transesterification reaction in the catalytic rectifying tower, collect sec-butyl alcohol from tower bottoms, wherein, described low-carbon alcohol is the alcohol of C1-C3.
The preparation method of sec-butyl alcohol according to the present invention can obtain higher sec-butyl acetate transformation efficiency and sec-butyl alcohol selectivity.
Method according to the present invention, technique is simple, and lower to the production unit requirement, raw material is easy to get, and energy consumption is low, thereby greatly reduces production cost; And, need not to use acetic acid to make raw material, reduced equipment corrosion and environmental pollution.
Embodiment
The preparation method of sec-butyl alcohol according to the present invention comprises: in the presence of transesterification catalyst, sec-butyl acetate and low-carbon alcohol be added to carry out transesterification reaction in the catalytic rectifying tower, collect sec-butyl alcohol from tower bottoms, wherein, described low-carbon alcohol is the alcohol of C1-C3.
Method according to the present invention, in order further to improve transformation efficiency and the sec-butyl alcohol selectivity of sec-butyl acetate, the operating process of described transesterification reaction preferably includes: with the sec-butyl acetate in the catalytic rectifying tower, the mixture heating up of low-carbon alcohol and transesterification catalyst is to boiling, and under the condition of total reflux, react the azeotropic point that reaches described low-carbon alcohol and described acetic acid ester of low-carbon alcohol to tower top temperature, then be 2-5 in reflux ratio: the azeotrope with described low-carbon alcohol and acetic acid ester of low-carbon alcohol under 1 the condition steams from cat head, reach the boiling point of described low-carbon alcohol until tower top temperature after, tower bottoms is discharged.
Method according to the present invention, the stage number of described catalytic rectifying tower or theoretical plate number are preferably the 40-50 piece.
Method according to the present invention, the mol ratio of sec-butyl acetate and described low-carbon alcohol can be 1: 2-10 is preferably 1: 3-6.
Method according to the present invention, described low-carbon alcohol can be in methyl alcohol, ethanol, propyl alcohol and the Virahol at least a.
Method according to the present invention, described transesterification catalyst can use with the catalytic amount of routine.Under the preferable case, with respect to the consumption of the sec-butyl acetate of 100 weight parts, the consumption of described transesterification catalyst can be the 0.1-10 weight part, is preferably the 0.5-5 weight part.
Method according to the present invention, described transesterification catalyst can be the conventional various transesterification catalysts that use in this area, for example can be in sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, cesium carbonate, tosic acid, zinc acetate, lead acetate, cadmium acetate, calcium oxide, zinc oxide, plumbous oxide, sodium methylate, tetrabutyl titanate, stannous octoate, sulfuric acid, phosphoric acid, polyphosphoric acid, acidic molecular sieve and the ion exchange resin at least a.Described acidic molecular sieve for example can be ZSM-5 molecular sieve, Y zeolite and H beta-molecular sieve.Described ion exchange resin can be acidic ion exchange resin or deacidite, and described acidic ion exchange resin for example can be styrene type cation exchange resin (such as commercially available D001 type, D201 type and D732 type Zeo-karb) or sulfonic group Zeo-karb (such as commercially available DWN type Zeo-karb); The anionite-exchange resin that described deacidite for example can obtain after the sodium hydroxide solution pre-treatment for quaternary ammonium group anionite-exchange resin, tertiary amine fundamental mode anionite-exchange resin or these anionite-exchange resin is such as 201 * 4 commercially available types, 201 * 4H type, D201 type and D301 type anionite-exchange resin.
Method according to the present invention is collected the method for sec-butyl alcohol and can be implemented according to the separation method of routine from tower bottoms, for example can adopt the method for distillation to separate.
The invention will be further described by the following examples.
In following examples, the transformation efficiency of the transformation efficiency of sec-butyl acetate, the selectivity of sec-butyl alcohol, sec-butyl alcohol and the selectivity of methylethylketone calculate according to following calculating formula respectively:
The charging capacity of the transformation efficiency of sec-butyl acetate=(residual volume of sec-butyl acetate in the charging capacity-reaction product of sec-butyl acetate)/sec-butyl acetate * 100%
The mole number of the sec-butyl acetate of the mole number of the sec-butyl alcohol of the selectivity of sec-butyl alcohol=generation/be converted * 100%
Embodiment 1
Present embodiment is used for illustrating the preparation method of described sec-butyl alcohol of the present invention.
Sec-butyl acetate and methyl alcohol are added in the catalytic rectifying tower (stage number is as 50) as 1: 4 take mol ratio, add-on with respect to the sec-butyl acetate of 100 weight parts, to the sodium methylate that wherein adds 2 weight parts as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 54 ℃ (azeotropic points of methyl alcohol and methyl acetate), tower top temperature begins extraction, the control reflux ratio is 5: 1, steams from cat head with the azeotrope with methyl alcohol and methyl acetate; After tower top temperature rises to 64 ℃ (boiling points of methyl alcohol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn that by calculating the transformation efficiency of sec-butyl acetate is 99.2%, the selectivity of sec-butyl alcohol is 100%.
Embodiment 2
Present embodiment is used for illustrating the preparation method of described sec-butyl alcohol of the present invention.
Sec-butyl acetate and ethanol are added in the catalytic rectifying tower (stage number is as 50) as 1: 4 take mol ratio, add-on with respect to the sec-butyl acetate of 100 weight parts, to the ZSM-5 molecular sieve that wherein adds 2 weight parts (available from Nanjing Ji Cang nanosecond science and technology company limited) as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 72 ℃ (azeotropic points of ethanol and ethyl acetate), tower top temperature begins extraction, the control reflux ratio is 3: 1, steams from cat head with the azeotrope with ethanol and ethyl acetate; After tower top temperature rises to 78 ℃ (boiling points of ethanol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn that by calculating the transformation efficiency of sec-butyl acetate is 99.7%, the selectivity of sec-butyl alcohol is 100%.
Embodiment 3
Present embodiment is used for illustrating the preparation method of described sec-butyl alcohol of the present invention.
Sec-butyl acetate and propyl alcohol are added in the catalytic rectifying tower (stage number is as 50) as 1: 4 take mol ratio, add-on with respect to the described sec-butyl acetate of 100 weight parts, to the D301 anionite-exchange resin that wherein adds 4 weight parts (available from Langfang prosperous chemical building material of prosperous Sheng company limited) as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 95 ℃ (azeotropic points of propyl alcohol and propyl acetate), tower top temperature begins extraction, the control reflux ratio is 2: 1, steams from cat head with the azeotrope with propyl alcohol and propyl acetate; After tower top temperature rises to 97 ℃ (boiling points of propyl alcohol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn that by calculating the selectivity of sec-butyl alcohol is 100%, the transformation efficiency of sec-butyl acetate is 99.5%.
Embodiment 4
Present embodiment is used for illustrating the preparation method of described sec-butyl alcohol of the present invention.
Sec-butyl acetate and Virahol are added in the catalytic rectifying tower (stage number is as 40) as 1: 7 take mol ratio, with respect to the described sec-butyl acetate of 100 weight parts and the gross weight of Virahol, to wherein adding 2 parts by weight of styrene cation exchange resins (available from Changsha Da Yu chemical industry company limited, trade mark D001) as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 80 ℃ (azeotropic points of Virahol and isopropyl acetate), tower top temperature begins extraction, the control reflux ratio is 3: 1, steams from cat head with the azeotrope with Virahol and isopropyl acetate; After tower top temperature rises to 82.5 ℃ (boiling points of Virahol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn that by calculating the selectivity of sec-butyl alcohol is 100%, the transformation efficiency of sec-butyl acetate is 99.3%.
Embodiment 5
Present embodiment is used for illustrating the preparation method of described sec-butyl alcohol of the present invention.
Sec-butyl acetate and ethanol are added in the catalytic rectifying tower (stage number is as 40) as 1: 3 take mol ratio, and to wherein adding CaO as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 72 ℃ (azeotropic points of ethanol and ethyl acetate), tower top temperature begins extraction, the control reflux ratio is 3: 1, steams from cat head with the azeotrope with ethanol and ethyl acetate; After tower top temperature rises to 78 ℃ (boiling points of ethanol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Prepare sec-butyl alcohol according to aforesaid method by sec-butyl acetate and ethanol, change is as the consumption of the CaO of catalyzer, wherein, the consumption of catalyzer and corresponding reaction times are as shown in table 1 below, and the consumption of the catalyzer shown in the table 1 is take the add-on of the sec-butyl acetate of 100 weight parts as benchmark.Calculate respectively the transformation efficiency of the sec-butyl acetate that the different catalysts consumption obtains and the selectivity of sec-butyl alcohol, its result is as shown in table 1 below.
Table 1
| Catalyzer (weight part) | The required reaction times (hour) | The transformation efficiency of sec-butyl acetate (%) | The selectivity of sec-butyl alcohol (%) |
| 0.1 | 9.7 | 99.3 | 100 |
| 0.5 | 7.5 | 99.5 | 100 |
| 1 | 6.6 | 99.2 | 100 |
| 2 | 5.7 | 99.6 | 100 |
| 5 | 4.8 | 99.4 | 100 |
| 7 | 4.3 | 99.7 | 100 |
| 10 | 3.9 | 99.8 | 100 |
Embodiment 6
Present embodiment is used for illustrating the preparation method of described sec-butyl alcohol of the present invention.
Sec-butyl acetate and ethanol are added in the catalytic rectifying tower (stage number is 40), add-on with respect to the sec-butyl acetate of 100 weight parts, to the tetrabutyl titanate that wherein adds 2 weight parts as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, begin extraction after tower top temperature reaches 72 ℃ (azeotropic points of ethanol and ethyl acetate), the control reflux ratio is 3: 1, steams from cat head with the azeotrope with ethanol and ethyl acetate; After tower top temperature rises to 78 ℃ (boiling points of ethanol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Prepare sec-butyl alcohol according to aforesaid method by sec-butyl acetate and ethanol, change the reinforced molar ratio (being ester alcohol mol ratio) of sec-butyl acetate and ethanol, wherein, ester alcohol mol ratio and corresponding reaction times are as shown in table 2 below.Calculate respectively the transformation efficiency of the sec-butyl acetate that different esters alcohol mol ratios obtain and the selectivity of sec-butyl alcohol, its result is as shown in table 2 below.
Table 2
| Ester alcohol mol ratio | The required reaction times (hour) | The transformation efficiency of sec-butyl acetate (%) | The selectivity of sec-butyl alcohol (%) |
| 1∶2 | 8.9 | 99.4 | 100 |
| 1∶3 | 6.3 | 99.2 | 100 |
| 1∶4 | 5.7 | 99.7 | 100 |
| 1∶6 | 4.6 | 99.8 | 100 |
| 1∶8 | 4.0 | 99.5 | 100 |
| 1∶10 | 3.4 | 99.6 | 100 |
| 1∶2 | 8.9 | 99.4 | 100 |
Result by above-described embodiment can find out, method according to the present invention can obtain higher sec-butyl acetate transformation efficiency and sec-butyl alcohol selectivity.
Claims (8)
1. the preparation method of a sec-butyl alcohol, the method comprises: in the presence of transesterification catalyst, sec-butyl acetate and low-carbon alcohol be added to carry out transesterification reaction in the catalytic rectifying tower, collect sec-butyl alcohol from tower bottoms, wherein, described low-carbon alcohol is the alcohol of C1-C3.
2. method according to claim 1, wherein, the operating process of described transesterification reaction comprises: with the extremely boiling of mixture heating up of the sec-butyl acetate in the catalytic rectifying tower, low-carbon alcohol and transesterification catalyst, and under the condition of total reflux, react the azeotropic point that reaches described low-carbon alcohol and described acetic acid ester of low-carbon alcohol to tower top temperature, then be 2-5 in reflux ratio: the azeotrope with described low-carbon alcohol and acetic acid ester of low-carbon alcohol under 1 the condition steams from cat head, reach the boiling point of described low-carbon alcohol until tower top temperature after, tower bottoms is discharged.
3. method according to claim 1 and 2, wherein, the mol ratio of sec-butyl acetate and described low-carbon alcohol is 1: 2-10.
4. method according to claim 3, wherein, the mol ratio of sec-butyl acetate and described low-carbon alcohol is 1: 3-6.
5. method according to claim 1 and 2, wherein, described low-carbon alcohol is at least a in methyl alcohol, ethanol, propyl alcohol and the Virahol.
6. method according to claim 1 and 2, wherein, with respect to the consumption of the sec-butyl acetate of 100 weight parts, the consumption of described transesterification catalyst is the 0.1-10 weight part.
7. method according to claim 6, wherein, with respect to total consumption of the sec-butyl acetate of 100 weight parts, the consumption of described transesterification catalyst is the 0.5-5 weight part.
8. method according to claim 1 and 2, wherein, described transesterification catalyst is at least a in sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, cesium carbonate, tosic acid, zinc acetate, lead acetate, cadmium acetate, calcium oxide, zinc oxide, plumbous oxide, sodium methylate, tetrabutyl titanate, stannous octoate, sulfuric acid, phosphoric acid, polyphosphoric acid, acidic molecular sieve and the ion exchange resin.
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| CN103232325A (en) * | 2013-04-18 | 2013-08-07 | 湖南长岭石化科技开发有限公司 | Method for preparing cyclohexanol from cyclohexene |
| CN105164099A (en) * | 2013-05-03 | 2015-12-16 | 陶氏环球技术有限责任公司 | Reactive chromatography process for equilibrium-limited reactions |
| CN105924347A (en) * | 2016-04-22 | 2016-09-07 | 盐城市春竹香料有限公司 | Technology for preparing isogalbanate |
| CN109503651A (en) * | 2019-01-08 | 2019-03-22 | 淄博市临淄齐泉工贸有限公司 | A kind of preparation method of chloropropyl triethoxysilane |
| US10919829B2 (en) | 2016-12-28 | 2021-02-16 | Kaneka Corporation | Method for producing alcohol compound |
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| CN101239907A (en) * | 2008-02-26 | 2008-08-13 | 华东师范大学 | Method for preparing glycol methyl ether acetate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103232325A (en) * | 2013-04-18 | 2013-08-07 | 湖南长岭石化科技开发有限公司 | Method for preparing cyclohexanol from cyclohexene |
| CN103232325B (en) * | 2013-04-18 | 2015-10-21 | 湖南长岭石化科技开发有限公司 | A kind of method being prepared hexalin by tetrahydrobenzene |
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| CN105164099B (en) * | 2013-05-03 | 2018-04-06 | 陶氏环球技术有限责任公司 | For being balanced the reactive chromatographic process of limited reactions |
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| US10919829B2 (en) | 2016-12-28 | 2021-02-16 | Kaneka Corporation | Method for producing alcohol compound |
| CN109503651A (en) * | 2019-01-08 | 2019-03-22 | 淄博市临淄齐泉工贸有限公司 | A kind of preparation method of chloropropyl triethoxysilane |
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Application publication date: 20130327 |