CN102557932B - Method for producing isobutyl acetate - Google Patents
Method for producing isobutyl acetate Download PDFInfo
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- CN102557932B CN102557932B CN201110423236.2A CN201110423236A CN102557932B CN 102557932 B CN102557932 B CN 102557932B CN 201110423236 A CN201110423236 A CN 201110423236A CN 102557932 B CN102557932 B CN 102557932B
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Abstract
The invention discloses a method for producing isobutyl acetate. The method comprises the following steps of: 1) adding a raw material substrate and a composite catalyst into an esterification reaction kettle, wherein the raw material substrate is a mixture of acetic acid and isobutanol, and the composite catalyst is a mixture obtained by mixing acid sulfate and p-toluenesulfonic acid in a molar ratio of 1:(2-1); and continuously adding the isobutanol and the acetic acid serving as raw materials into the esterification reaction kettle in a molar ratio of 1:1, wherein esterification reaction temperature is between 98 and 118 DEG C, and esterification reaction pressure is 0.01 to 0.1MPa; and 2) discharging crude ester liquid containing the isobutyl acetate from the esterification reaction kettle, adding into a rectifying tower for separating, extracting the isobutyl acetate serving as a finished product at the bottom of the rectifying tower, and evaporating a mixture of the isobutanol and water on the top of the rectifying tower; and performing phase separation on the mixture of the isobutanol and the water, and returning the separated isobutanol to the esterification reaction kettle for recycling. The method for producing the isobutyl acetate has the characteristic of high product yield.
Description
Technical field
The present invention relates to a kind of production method of organic chemicals, particularly a kind of production method of serialization isobutyl acetate.
Background technology
Isobutyl acetate is important organic chemical industry's intermediate, be widely used in the fields such as solvent, softening agent, tensio-active agent and polymer monomer, along with China PTA industry, the paint fast development of industry, coating industry and medical pesticide industry and continually developing of downstream industry thereof, isobutyl acetate has a extensive future in recent years.Its structural formula:
The conventional production methods of isobutyl acetate is that acetic acid and isopropylcarbinol (are H at sulfuric acid catalyst
2sO
4, industrial applications is mainly 30%, 98% content) existence under intermittent type esterification carry out, energy consumption is large, production capacity is little, yield low (≤85%), side reaction is many, equipment corrosion is serious, wastewater flow rate is large, labour intensity is large, the more difficult control of process.
Also the research report that had in the last few years some to utilize non-mineral acid catalytic esterification: Chen Ping, the Research advance in catalysts for production < < application chemical industry > > 2004 of synthesis of acetic acid isobutyl ester, 33 (2), 4-6 has introduced with rare-earth oxide phase-transfer catalyst, thionamic acid, heteropolyacid, the research of the catalyst synthesis of acetic acid isobutyl esters such as ferric ammonium sulfate, stated that especially silica gel load tin tetrachloride is catalyzer, its catalytic activity is high, selectivity is good, but (final transformation efficiency only has 93.8%, yield is 91.9%), Li Xiaoli, Wang Xiaoju, three oxidation diamine catalyst are prepared isobutyl acetate < < rare earth > > 2011,22 (3), and its sour yield of 73-74 reaches 80%, patent " method of reaction rectification coupling continuous preparation of and series acetate " CN183718.3 is disclosed is that employing modification strongly acidic styrene type cation exchange resin is that catalyzer is coupled by reaction rectification, and yield reaches 95%.Aspect product separation research, patent " a kind of method of azeotropic distillation separating isobutyl acetate, acetic acid, water " CN101412671 discloses and has utilized additive entrainer to carry out two tower rectifying.
Summary of the invention
The technical problem to be solved in the present invention is to provide the production method of the isobutyl acetate that a kind of product yield is high.
In order to solve the problems of the technologies described above, the invention provides a kind of production method of isobutyl acetate, comprise the following steps:
1), first at reaction kettle of the esterification, add raw material bed material and composite catalyst, raw material bed material is the mixture of acetic acid and isopropylcarbinol; Composite catalyst is 0.5～1.5% (the best is 1～1.5%) of raw material bed material gross weight, the composite catalyst mixture that to be bisul-phate and tosic acid obtain according to 1: 2～1 mixed in molar ratio;
Subsequently the mol ratio isopropylcarbinol of 1: 1 and acetic acid are added in reaction kettle of the esterification as raw material continuously;
The temperature of esterification is that 98～118 ℃, pressure are 0.01～0.1MPa;
2), the thick ester liquid that contains isobutyl acetate enters rectifying tower separation after discharging reaction kettle of the esterification, at the bottom of rectifying tower, extraction is as the isobutyl acetate of finished product, rectifying tower tower top steams the mixture of isobutyl alcohol and water;
The mixture of isobutyl alcohol and water is through phase-splitting, and isolated isopropylcarbinol is back in reaction kettle of the esterification and is recycled.
Improvement as the production method of isobutyl acetate of the present invention: in raw material bed material, the mass ratio of acetic acid and isopropylcarbinol is 1～2: 1.
Further improvement as the production method of isobutyl acetate of the present invention: bisul-phate is NaHSO
4, BaHSO
4, CaHSO
4or MgHSO
4.
Further improvement as the production method of isobutyl acetate of the present invention: feed volume air speed is 0.1～0.7h
-1, feed volume air speed
illustrate: the catalyzer in formula represents composite catalyst.
The production method of isobutyl acetate of the present invention, reaction equation is as follows:
The production method of isobutyl acetate of the present invention, owing to having adopted special composite catalyst, and the continuous operation mode of reaction and separated employing one still one tower, separating obtained isopropylcarbinol can be repeated to recycle, and whole process can adopt DCS to control (being conventional dispersing control system).The thick ester solution of gained (i.e. the thick ester liquid from discharging at reaction kettle of the esterification), contain >=90% isobutyl acetate.The present invention prepares reaction bed material by raw material by excessive acid in advance in reaction kettle of the esterification, then presses alcohol, the continuously feeding in 1: 1 of sour mol ratio, the continuous extraction of target product.Per pass conversion is more than 90%, and more than product ultimate yield 99% (for " isopropylcarbinol "), product purity reaches more than 99.5%.
In sum, the production method of isobutyl acetate of the present invention adopts the tower reaction of a still one, and flow process is brief, and omnidistance reaction is controlled automatically by DCS.This method advantages such as mild condition, easy and simple to handle, selectivity is high, side reaction is few, yield is high, the reaction times is short, aftertreatment is easy that respond.
Accompanying drawing explanation
Below in conjunction with accompanying drawing, the specific embodiment of the present invention is described in further detail.
Fig. 1 is process flow diagram of the present invention.
Embodiment
The production method of embodiment 1, a kind of isobutyl acetate, the production equipment of the isobutyl acetate using, mainly comprises reaction kettle of the esterification, rectifying tower and phase splitter.
Reaction kettle of the esterification is a stainless steel reaction pipe, the ratio of its internal diameter and total height: 1: 1.3～2 (for example internal diameter Φ=200mm, is highly 300mm).Vapour source is connected with reaction kettle of the esterification by the pipeline with valve (being steam valve).
The isopropylcarbinol head tank of the acetic acid head tank of storage acetic acid, storage isopropylcarbinol is respectively by being connected with reaction kettle of the esterification after under meter variable valve separately.
Above-mentioned 2 under meter variable valve all can be connected with DCS Controlling System signal with steam valve, thereby realize automatization, control.
From the tip position of reaction kettle of the esterification, add composite catalyst 4.5g.Acetic acid enters in reaction kettle of the esterification as raw material bed material respectively with isopropylcarbinol after under meter mixes in mass ratio at 1: 1, and the volume of raw material bed material is 500ml; That is, composite catalyst accounts for 1% of raw material bed material gross weight.By DCS, control, on operator's console, proceed as follows: control steam valve aperture and heat up and reaction pressure to control reaction kettle of the esterification, when rising to 60～80 ℃, the temperature in reaction kettle of the esterification just can open gradually acetic acid, isopropylcarbinol under meter variable valve, regulate charging aperture (to control feed rate,) flow of controlling acetic acid is 200ml/h, the about 320ml/h of flow of corresponding control isopropylcarbinol, thus guarantee that acetic acid and isopropylcarbinol enter for 1: 1 in molar ratio continuously; Under the heat effect of steam, when the temperature in reaction kettle of the esterification rises to 100～105 ℃, now the pressure in reaction kettle of the esterification is 0.03～0.05MPa, regulating the flow of acetic acid is 400ml/h, the corresponding flow that regulates isopropylcarbinol, thus still guarantee that acetic acid and isopropylcarbinol enter for 1: 1 in molar ratio continuously.The preparation method of this composite catalyst is: bisul-phate and tosic acid are simply mixed according to the mol ratio of 1: 2.Bisul-phate is selected NaHSO
4.
Preparation in reaction kettle of the esterification and thick ester liquid enter and in treating tower, carry out fractionation.The top temperature of controlling treating tower is 95～100 ℃, and the column bottom temperature for the treatment of tower is controlled 120 ℃～130 ℃; Pressure in treating tower is 0.1～0.3Mpa.
The impurity of the water in thick ester liquid, isopropylcarbinol and light boiling point is discharged from the tower top for the treatment of tower, and isobutyl acetate goes out by water cooler to be cooled to normal temperature from the tower bottom flow for the treatment of tower.
The product that the above-mentioned tower top from treating tower is discharged is after the phase separation of phase splitter, and the impurity of light boiling point is discharged from the top of phase splitter, and isopropylcarbinol is positioned at the top of phase splitter, and water level is in the bottom of phase splitter, that is, and and isobutyl alcohol and water natural layering; This isopropylcarbinol (purity is 80～95%) can be directly by entering in reaction kettle of the esterification after corresponding under meter variable valve.Also can be after again conventional rectification process, by entering (the present embodiment is selected this mode) in reaction kettle of the esterification after corresponding under meter variable valve.
The condition of above-mentioned rectification process is again as follows: 90～105 ℃ of still temperature, 95～100 ℃ of top temperature, still internal pressure 0.1～0.3Mpa; Isopropylcarbinol content >=99.5% after refining.
The purity of the isobutyl acetate of final gained is 98.8%, the acidity that contains 0.1% moisture content and 0.01%; Above-mentioned % is mass percent.Yield is 98.5%.
The production method of embodiment 2, a kind of isobutyl acetate, the production equipment of the isobutyl acetate using is with the production equipment of embodiment 1;
In reaction kettle of the esterification, by acid alcohol mass ratio, add the isopropylcarbinol of 500ml and the raw material bed material that acetic acid is obtained by mixing at 2: 1 in advance, the composite catalyst 5.9g that adds bisul-phate and tosic acid to be obtained by mixing at 1: 1.5 according to mol ratio, that is, composite catalyst accounts for 1.25% of raw material bed material gross weight.Bisul-phate is selected BaHSO
4.
By DCS, control, on operator's console, proceed as follows: control steam valve aperture and heat up and reaction pressure to control reaction kettle of the esterification, when rising to 60～80 ℃, the temperature in reaction kettle of the esterification just can open gradually acetic acid, isopropylcarbinol under meter variable valve, regulate charging aperture (to control feed rate,) flow of controlling acetic acid is 200ml/h, the about 320ml/h of flow of corresponding control isopropylcarbinol, thus guarantee that acetic acid and isopropylcarbinol enter for 1: 1 in molar ratio continuously; When the temperature in reaction kettle of the esterification rises to 100～105 ℃, now the pressure in reaction kettle of the esterification is 0.03～0.05MPa, regulating the flow of acetic acid is 400ml/h, regulates accordingly the flow of isopropylcarbinol, thereby still guarantees that acetic acid and isopropylcarbinol enter for 1: 1 in molar ratio continuously.
Preparation in reaction kettle of the esterification and thick ester enter and in treating tower, carry out fractionation.The top temperature of controlling treating tower is 95～100 ℃, and the column bottom temperature for the treatment of tower is controlled 120 ℃～130 ℃; Pressure in treating tower is 0.1～0.3Mpa.
The impurity of the water in thick ester liquid, isopropylcarbinol and light boiling point is discharged from the tower top for the treatment of tower, and isobutyl acetate goes out by water cooler to be cooled to normal temperature from the tower bottom flow for the treatment of tower.
The product that the above-mentioned tower top from treating tower is discharged is after the phase separation of phase splitter, and the impurity of light boiling point is discharged from the top of phase splitter, and isopropylcarbinol is positioned at the top of phase splitter, and water level is in the bottom of phase splitter, that is, and and isobutyl alcohol and water natural layering; This isopropylcarbinol passes through again after rectification process (processing mode is with embodiment 1), by entering in reaction kettle of the esterification after corresponding under meter variable valve.
Yield is 99.0%.
The purity of the isobutyl acetate of final gained is: 99.3%, and moisture content %:0.2%, acidity %:0.01%; Above-mentioned % is mass percent.
The production method of embodiment 3, a kind of isobutyl acetate, the production equipment of the isobutyl acetate using is with the production equipment of embodiment 1;
In reaction kettle of the esterification, by acid alcohol mass ratio, add the isopropylcarbinol of 500ml and the raw material bed material that acetic acid is obtained by mixing at 2: 1 in advance, the composite catalyst 4.75g that adds bisul-phate and tosic acid (mol ratio 1: 1) to be obtained by mixing, that is, composite catalyst accounts for 1.0% of raw material bed material gross weight.Bisul-phate is selected CaHSO
4.
All the other are with embodiment 1.
Yield is 98.9%.
The purity of the isobutyl acetate of final gained is 99.0%, moisture content %:0.1%, acidity %:0.01%; Above-mentioned % is mass percent.
The production method of embodiment 4, a kind of isobutyl acetate, the production equipment of the isobutyl acetate using is with the production equipment of embodiment 1;
In reaction kettle of the esterification, by acid alcohol mass ratio, add the isopropylcarbinol of 500ml and the raw material bed material that acetic acid is obtained by mixing at 2: 1 in advance, the composite catalyst 7g that adds bisul-phate and tosic acid to be obtained by mixing at 1: 2 according to mol ratio, that is, composite catalyst accounts for 1.5% of raw material bed material gross weight.This bisul-phate is selected and is changed MgHSO4 into.
All the other workflows are with embodiment 1.
Yield is 98.7%.
The purity of the isobutyl acetate of final gained is 99.5%, moisture content %:0.1%, acidity %:0.01%; Above-mentioned % is mass percent.
Comparative example 1, make the composite catalyst 4.5g in embodiment 1 into tosic acid 4.5g, all the other are completely with embodiment 1.
Yield is 85.5%.
The purity of the isobutyl acetate of final gained is 91.6%, moisture content %:0.3%, acidity %:0.08%.
Comparative example 2, make the composite catalyst 4.5g in embodiment 1 into NaHSO
44.5g, all the other are completely with embodiment 1.
Yield is 88.1%.
The purity of the isobutyl acetate of final gained is 93.2%, moisture content %:0.2%, acidity %:0.07%.
Comparative example 3, by 4.5g, make the composite catalyst in embodiment 1 into 3.5g, all the other are completely with embodiment 1.
Yield is 90.9%.
The purity of the isobutyl acetate of final gained is 96.8%, moisture content %:0.1%, acidity %:0.02%.
Comparative example 4, by the composite catalyst in embodiment 1 by NaHSO
4: tosic acid=1: 2 mol ratio makes NaHSO into
4: tosic acid=1: 2.5 mol ratio; All the other are completely with embodiment 1.
Yield is 91.2%.
The purity of the isobutyl acetate of final gained is 98.1%, moisture content %:0.1%, acidity %:0.05%.
Comparative example 5, by the composite catalyst in embodiment 1 by NaHSO
4: tosic acid=1: 2 mol ratio makes NaHSO into
4: tosic acid=1: 0.8 mol ratio; All the other are completely with embodiment 1.
Yield is 92.5%.
The purity of the isobutyl acetate of final gained is 98.1%, moisture content %:0.1%, acidity %:0.05%.
Finally, it is also to be noted that, what more than enumerate is only a specific embodiment of the present invention.Obviously, the invention is not restricted to above embodiment, can also have many distortion.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention, all should think protection scope of the present invention.
Claims (2)
1. the production method of isobutyl acetate, is characterized in that comprising the following steps:
1), first at reaction kettle of the esterification, add raw material bed material and composite catalyst, described raw material bed material is the mixture of acetic acid and isopropylcarbinol; Described composite catalyst is 0.5～1.5% of raw material bed material gross weight, and composite catalyst is the mixture that bisul-phate and tosic acid obtain according to the mixed in molar ratio of 1:2～1; In described raw material bed material, the mass ratio of acetic acid and isopropylcarbinol is 1～2:1; Described bisul-phate is NaHSO
4, Ba(HSO
4)
2, Ca(HSO
4)
2or Mg(HSO
4)
2;
Subsequently the isopropylcarbinol of mol ratio 1:1 and acetic acid are added in reaction kettle of the esterification as raw material continuously;
The temperature of esterification is that 98～118 ℃, pressure are 0.01 ~ 0.1MPa;
2), the thick ester liquid that contains isobutyl acetate enters rectifying tower separation after discharging from reaction kettle of the esterification, at the bottom of rectifying tower, extraction is as the isobutyl acetate of finished product, rectifying tower tower top steams the mixture of isobutyl alcohol and water;
The mixture of isobutyl alcohol and water is through phase-splitting, and isolated isopropylcarbinol is back in reaction kettle of the esterification and is recycled.
2. the production method of isobutyl acetate according to claim 1, is characterized in that: feed volume air speed is 0.1～0.7h
-1, described feed volume air speed
.
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| CN103254068A (en) * | 2013-05-22 | 2013-08-21 | 江门天诚溶剂制品有限公司 | Energy-saving multi-effect distillation process for producing n-butyl acetate |
| CN106146303A (en) * | 2016-07-26 | 2016-11-23 | 江门谦信化工发展有限公司 | A kind of acetic acid mixes continuous process system and the method for butyl ester |
| CN113045417B (en) * | 2019-12-29 | 2023-04-07 | 南通醋酸化工股份有限公司 | Process for producing acetoacetic ester by catalytic method |
| CN111167378B (en) * | 2020-01-29 | 2022-09-02 | 浙江建业化工股份有限公司 | Method for producing n-propyl acetate by continuous two-stage esterification reaction |
| CN111747849B (en) * | 2020-07-02 | 2023-05-02 | 浙江建业化工股份有限公司 | Method for synthesizing n-propyl acetate by continuous catalytic esterification of benzenesulfonic acid and derivatives thereof |
| CN115368242B (en) * | 2021-05-20 | 2024-09-06 | 浙江建业化工股份有限公司 | Preparation method of diisobutyl phthalate |
| CN115608410B (en) * | 2021-07-13 | 2023-10-13 | 中国石油化工股份有限公司 | Catalyst for synthesizing n-butyl acetate and preparation method and application thereof |
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