CN102557932A - Method for producing isobutyl acetate - Google Patents
Method for producing isobutyl acetate Download PDFInfo
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- CN102557932A CN102557932A CN2011104232362A CN201110423236A CN102557932A CN 102557932 A CN102557932 A CN 102557932A CN 2011104232362 A CN2011104232362 A CN 2011104232362A CN 201110423236 A CN201110423236 A CN 201110423236A CN 102557932 A CN102557932 A CN 102557932A
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- isobutyl acetate
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- esterification
- isopropylcarbinol
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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 working method of organic chemicals, particularly a kind of working method of serialization isobutyl acetate.
Background technology
Isobutyl acetate is important organic chemical industry's midbody; Be widely used in 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 mainly is 30%, 98% content) existence under the intermittent type esterification carry out, energy consumption is big, production capacity is little, yield low (≤85%), side reaction is many, equipment corrosion is serious, wastewater flow rate is big, labour intensity is big, the difficult control of process.
Some research that utilizes non-mineral acid catalytic esterification report: Chen Ping were also arranged in the last few years; Catalyst research progress " the application chemical industry " 2004 of synthesis of acetic acid isobutylate; 33 (2); 4-6 has introduced the research with catalyst synthesis of acetic acid isobutylates such as rare-earth oxide phase-transfer catalyst, thionamic acid, heteropolyacid, ferric ammonium sulfates, has stated that especially the silica gel load tin tetrachloride is a catalyzer, and its catalytic activity is high, selectivity is good; But final transformation efficiency has only 93.8% (that is, yield is 91.9%); Li Xiaoli, Wang Xiaoju, three oxidation diamine catalyst prepare 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 to be that employing modification strongly acidic styrene type cation exchange resin is that catalyzer passes through the reaction rectification coupling, and yield reaches 95%.Aspect product separation research, patent " method of a kind of azeotropic distillation separating isobutyl acetate, acetate, water " CN101412671 discloses and has utilized the additive entrainer to carry out two tower rectifying.
Summary of the invention
The technical problem that the present invention will solve provides the working method of the high isobutyl acetate of a kind of product yield.
In order to solve the problems of the technologies described above, the present invention provides a kind of working method of isobutyl acetate, may further comprise the steps:
1), earlier add raw material bed material and composite catalyst at reaction kettle of the esterification, the 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 get according to 1: 2～1 mixed in molar ratio;
Continuously add reaction kettle of the esterification in as raw material 1: 1 isopropylcarbinol of mol ratio and acetic acid subsequently;
The temperature of esterification is that 98～118 ℃, pressure are 0.01～0.1MPa;
2), the thick ester liquid that contains isobutyl acetate gets into rectifying tower and separates from reaction kettle of the esterification, discharging the back, extraction is as the isobutyl acetate of finished product at the bottom of the rectifying Tata, the rectifying tower cat head 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 the reaction kettle of the esterification and is recycled.
Improvement as the working method of isobutyl acetate of the present invention: the mass ratio of acetic acid and isopropylcarbinol is 1～2: 1 in the raw material bed material.
Further improvement as the working method of isobutyl acetate of the present invention: bisul-phate is NaHSO
4, BaHSO
4, CaHSO
4Or MgHSO
4
Further improvement as the working method of isobutyl acetate of the present invention: the feed volume air speed is 0.1～0.7h
-1, the feed volume air speed
Explain: the catalyzer in the formula is promptly represented composite catalyst.
The working method of isobutyl acetate of the present invention, reaction equation is following:
The working method of isobutyl acetate of the present invention; Owing to adopted special composite catalyst; And reaction can be repeated to recycle with the continuous operation mode of separating employing one still one tower, separating obtained isopropylcarbinol, and whole process can adopt DCS control (promptly conventional dispersing control system).Contain the thick ester solution of gained (i.e. thick ester liquid from discharging) >=90% isobutyl acetate at reaction kettle of the esterification.The present invention prepares the reaction bed material with raw material by excessive acid in advance in reaction kettle of the esterification, then by alcohol, the continuously feeding in 1: 1 of sour mol ratio, the continuous extraction of title product.Per pass conversion is more than 90%, and more than the product ultimate yield 99% (for " isopropylcarbinol "), product purity reaches more than 99.5%.
In sum, the working method of isobutyl acetate of the present invention adopts a still one tower reaction, and flow process is brief, and omnidistance reaction is controlled through DCS automatically.This method respond mild condition, easy and simple to handle, advantage such as selectivity is high, side reaction is few, yield is high, the reaction times is short, aftertreatment is easy.
Description of drawings
Do further explain below in conjunction with the accompanying drawing specific embodiments of the invention.
Fig. 1 is a process flow diagram of the present invention.
Embodiment
The working method of embodiment 1, a kind of isobutyl acetate, the production equipment of employed isobutyl acetate 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 highly is 300mm).Vapour source is connected with reaction kettle of the esterification through the pipeline that has valve (being steam valve).
The isopropylcarbinol head tank of the acetic acid head tank of storage acetic acid, storage isopropylcarbinol is respectively through being connected with reaction kettle of the esterification behind the under meter variable valve separately.
Above-mentioned 2 under meter variable valve all can link to each other with DCS system signal with steam valve, thereby realize robotization control.
Add composite catalyst 4.5g from the tip position of reaction kettle of the esterification.Acetic acid is pressed through under meter respectively with isopropylcarbinol and is got in the reaction kettle of the esterification as the raw material bed material after mass ratio mixes 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.Control through DCS; On operator's console, operate as follows: control steam valve aperture heats up and reaction pressure with the control reaction kettle of the esterification; When the temperature in the reaction kettle of the esterification rises to 60～80 ℃, just can open acetic acid, isopropylcarbinol under meter variable valve gradually, the flow of regulating charging aperture (control feed rate) control acetic acid is 200ml/h; The about 320ml/h of the flow of corresponding control isopropylcarbinol, thus guarantee that acetic acid and isopropylcarbinol got in 1: 1 in molar ratio continuously; Under the heat effect of steam; When the temperature in the reaction kettle of the esterification rises to 100～105 ℃; The interior pressure of reaction kettle of the esterification this moment is 0.03～0.05MPa; The flow of regulating acetic acid is 400ml/h, regulates the flow of isopropylcarbinol accordingly, thereby guarantees that still acetic acid and isopropylcarbinol got in 1: 1 in molar ratio continuously.The preparation method of this composite catalyst is: bisul-phate and tosic acid simply mix according to 1: 2 mol ratio and get final product.Bisul-phate is selected NaHSO for use
4
The thick ester liquid for preparing in the reaction kettle of the esterification and get gets in the treating tower and carries out fractionation.The top temperature of control treating tower is 95～100 ℃, 120 ℃～130 ℃ of the column bottom temperature controls of treating tower; Pressure in the treating tower is 0.1～0.3Mpa.
The impurity of the water in the thick ester liquid, isopropylcarbinol and light boiling point is discharged from the cat head of treating tower, and isobutyl acetate goes out after water cooler is cooled to normal temperature from the tower bottom flow of treating tower.
The product that above-mentioned cat head from treating tower is discharged is behind 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 through getting in the reaction kettle of the esterification behind the pairing under meter variable valve.Also can be through after the conventional once more rectification process, through getting in the reaction kettle of the esterification (present embodiment is selected this mode for use) behind the pairing under meter variable valve.
The condition of above-mentioned rectification process once more is following: 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%, contains the acidity of 0.1% moisture content and 0.01%; Above-mentioned % is a mass percent.Yield is 98.5%.
The working method of embodiment 2, a kind of isobutyl acetate, the production equipment of employed isobutyl acetate is with the production equipment of embodiment 1;
Press in reaction kettle of the esterification in advance that isopropylcarbinol that acid alcohol mass ratio 2: 1 adds 500ml mixes with acetic acid and must the raw material bed material; Add the composite catalyst 5.9g that bisul-phate and tosic acid get according to mol ratio mixing in 1: 1.5; That is, composite catalyst accounts for 1.25% of raw material bed material gross weight.Bisul-phate is selected BaHSO for use
4
Control through DCS; On operator's console, operate as follows: control steam valve aperture heats up and reaction pressure with the control reaction kettle of the esterification; When the temperature in the reaction kettle of the esterification rises to 60～80 ℃, just can open acetic acid, isopropylcarbinol under meter variable valve gradually, the flow of regulating charging aperture (control feed rate) control acetic acid is 200ml/h; The about 320ml/h of the flow of corresponding control isopropylcarbinol, thus guarantee that acetic acid and isopropylcarbinol got in 1: 1 in molar ratio continuously; When the temperature in the reaction kettle of the esterification rises to 100～105 ℃; The interior pressure of reaction kettle of the esterification this moment is 0.03～0.05MPa; The flow of regulating acetic acid is 400ml/h, regulates the flow of isopropylcarbinol accordingly, thereby guarantees that still acetic acid and isopropylcarbinol got in 1: 1 in molar ratio continuously.
The thick ester for preparing in the reaction kettle of the esterification and get gets in the treating tower and carries out fractionation.The top temperature of control treating tower is 95～100 ℃, 120 ℃～130 ℃ of the column bottom temperature controls of treating tower; Pressure in the treating tower is 0.1～0.3Mpa.
The impurity of the water in the thick ester liquid, isopropylcarbinol and light boiling point is discharged from the cat head of treating tower, and isobutyl acetate goes out after water cooler is cooled to normal temperature from the tower bottom flow of treating tower.
The product that above-mentioned cat head from treating tower is discharged is behind 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; After this isopropylcarbinol passes through once more rectification process (processing mode is with embodiment 1), through getting in the reaction kettle of the esterification behind the pairing 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 a mass percent.
The working method of embodiment 3, a kind of isobutyl acetate, the production equipment of employed isobutyl acetate is with the production equipment of embodiment 1;
Press in reaction kettle of the esterification in advance that isopropylcarbinol that acid alcohol mass ratio 2: 1 adds 500ml mixes with acetic acid and must the raw material bed material; The composite catalyst 4.75g that adds the mixing of bisul-phate and tosic acid (mol ratio 1: 1) and get; That is, composite catalyst accounts for 1.0% of raw material bed material gross weight.Bisul-phate is selected CaHSO for use
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 a mass percent.
The working method of embodiment 4, a kind of isobutyl acetate, the production equipment of employed isobutyl acetate is with the production equipment of embodiment 1;
Press in reaction kettle of the esterification in advance that isopropylcarbinol that acid alcohol mass ratio 2: 1 adds 500ml mixes with acetic acid and must the raw material bed material; Add the composite catalyst 7g that bisul-phate and tosic acid get according to mol ratio mixing in 1: 2; That is, composite catalyst accounts for 1.5% of raw material bed material gross weight.This bisul-phate is selected for use 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 a mass percent.
Comparative Examples 1, make the composite catalyst 4.5g among the embodiment 1 into tosic acid 4.5g, all the other are fully 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 Examples 2, make the composite catalyst 4.5g among the embodiment 1 into NaHSO
44.5g all the other are fully 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 Examples 3, make the composite catalyst among the embodiment 1 into 3.5g by 4.5g, all the other are fully 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 Examples 4, with the composite catalyst among the embodiment 1 by NaHSO
4: the mol ratio of tosic acid=1: 2 makes NaHSO into
4: the mol ratio of tosic acid=1: 2.5; All the other are fully 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 Examples 5, with the composite catalyst among the embodiment 1 by NaHSO
4: the mol ratio of tosic acid=1: 2 makes NaHSO into
4: the mol ratio of tosic acid=1: 0.8; All the other are fully 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%.
At last, it is also to be noted that what more than enumerate only is a specific embodiment of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (4)
1. the working method of isobutyl acetate is characterized in that may further comprise the steps:
1), earlier add raw material bed material and composite catalyst at reaction kettle of the esterification, said raw material bed material is the mixture of acetic acid and isopropylcarbinol; Said composite catalyst is 0.5～1.5% of a raw material bed material gross weight, the composite catalyst mixture that to be bisul-phate and tosic acid get according to 1: 2～1 mixed in molar ratio;
Continuously add reaction kettle of the esterification in as raw material 1: 1 isopropylcarbinol of mol ratio and acetic acid subsequently;
The temperature of esterification is that 98～118 ℃, pressure are 0.01～0.1MPa;
2), the thick ester liquid that contains isobutyl acetate discharges the back and gets into rectifying tower and separate from reaction kettle of the esterification, extraction is as the isobutyl acetate of finished product at the bottom of the rectifying Tata, the rectifying tower cat head 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 the reaction kettle of the esterification and is recycled.
2. the working method of isobutyl acetate according to claim 1, it is characterized in that: the mass ratio of acetic acid and isopropylcarbinol is 1～2: 1 in the said raw material bed material.
3. the working method of isobutyl acetate according to claim 2, it is characterized in that: said bisul-phate is NaHSO
4, BaHSO
4, CaHSO
4Or MgHSO
4
4. according to the working method of claim 1,2 or 3 described isobutyl acetates, it is characterized in that: the feed volume air speed is 0.1～0.7h
-1, said feed volume air speed
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Cited By (7)
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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 |
| CN111167378A (en) * | 2020-01-29 | 2020-05-19 | 浙江建业化工股份有限公司 | Method for producing n-propyl acetate by continuous two-stage esterification reaction |
| CN111747849A (en) * | 2020-07-02 | 2020-10-09 | 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 |
| CN113045417A (en) * | 2019-12-29 | 2021-06-29 | 南通醋酸化工股份有限公司 | Process for producing acetoacetic ester by green catalytic method |
| CN115368242A (en) * | 2021-05-20 | 2022-11-22 | 浙江建业化工股份有限公司 | Preparation method of diisobutyl phthalate |
| CN115608410A (en) * | 2021-07-13 | 2023-01-17 | 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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| 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 |
| CN113045417A (en) * | 2019-12-29 | 2021-06-29 | 南通醋酸化工股份有限公司 | Process for producing acetoacetic ester by green catalytic method |
| 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 |
| CN111167378A (en) * | 2020-01-29 | 2020-05-19 | 浙江建业化工股份有限公司 | Method for producing n-propyl acetate by continuous two-stage esterification reaction |
| 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 |
| CN111747849A (en) * | 2020-07-02 | 2020-10-09 | 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 |
| 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 |
| CN115368242A (en) * | 2021-05-20 | 2022-11-22 | 浙江建业化工股份有限公司 | Preparation method of diisobutyl phthalate |
| CN115608410A (en) * | 2021-07-13 | 2023-01-17 | 中国石油化工股份有限公司 | Catalyst for synthesizing n-butyl acetate and preparation method and application thereof |
| 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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