Integration of the Process for Production of Ethyl Acetate by an Enhanced Extraction Process
Abstract
:1. Introduction
1.1. Synthesis Methods
1.2. Purification Method
- (1)
- First is the process of rectifying the reaction mixture, i.e., stripping acetic acid by a rectification column and distilling the ethyl acetate–ethanol–water (EA–ET–W) ternary azeotrope. In order to generate an azeotrope by the distillation of reaction products, and to avoid accumulating water in the reactor, an azeotropic agent should be fed to the column. By esterification of the acetic acid with ethanol, some excess water is released (approximately 17%) [29] which is more than contained in the azeotrope mixture (approximately 7.8%). Therefore, the azeotropic agent is the organic phase in the extraction process, recycled to the column. This fraction is richer in ethyl acetate than the azeotrope (>93%) [8], so it binds the excess water.
- (2)
- After azeotropic distillation, there is an extraction process. To obtain enriched phase of ethyl acetate from the distillation product, it is necessary to wash it with water and extract ethanol. The ethanol content of the organic mixture affects the solubility of water in this phase. The higher is the content of alcohol, the greater the water content in the organic phase. By extracting ethanol, water is also removed from the organic phase [8].
- (3)
- The final stage is the process of product rectification. Enriched phase of ethyl acetate is fed to the rectification column, where, by distilling the triple azeotrope, a pure ethyl acetate is obtained as the bottom product [8].
2. Methodology
- -
- a closed circuit of the extractant, demineralized water, reducing the consumption of the fresh extractant, but also a deep recovery of raw materials, i.e., ethyl acetate and ethanol from wastewater, significantly reducing the TOL;
- -
- cooling the azeotrope before extraction (Streams 8 and 14, Figure 1) from 70 °C down to 30 °C (HTXR 6, 12, Figure 1), shifting a phase equilibrium towards higher concentrations of EA in the organic phase, resulting in a reduced reflux on the azeotropic column as well as the reduced flowrate of the water phase directed to the wastewater treatment plant.
2.1. Thermodynamic Model
2.2. Kinetics of Esterification Reaction
3. Results
3.1. Optimization of the Reaction System
3.2. Optimization of Azeotropic Distillation
3.3. Optimization of the Extraction System
3.4. Optimization of Product Distillation
3.5. Optimization of Wastewater Distillation
3.6. Mass and Heat Balance of the Different Process Aproaches
4. Discussion
5. Conclusions
- ethanol consumption was reduced from 0.531 to 0.524 t/tproduct (−1.2%);
- the amount of process water was reduced from 2.18 to 1.42 t/tproduct (−34.9%);
- the product quality was improved from 98.0% to 99.9%;
- wastewater production was reduced from 2.36 to 1.61 t/tproduct (−31.8%) and the TOC/COD was reduced almost nine times.
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Appendix A
Stream No. | Molar Flow kmol/h | Mass Flow kg/h | Temp. °C | Pres. Bar | Component Mass % | |||
---|---|---|---|---|---|---|---|---|
Ethanol | Water | Ethyl Acetate | Acetic Acid | |||||
1 | 141.3 | 6511 | 15 | 1 | 100.00 | 0.00 | 0.00 | 0.00 |
2 | 141.1 | 8472 | 15 | 1 | 0.00 | 0.00 | 0.00 | 100.00 |
3 | 282.4 | 14,983 | 15 | 1 | 43.46 | 0.00 | 0.00 | 56.54 |
4 | 282.4 | 14,983 | 70 | 1 | 43.46 | 0.00 | 0.00 | 56.54 |
5 | 1223.3 | 47,670 | 77 | 1 | 28.65 | 22.96 | 25.67 | 22.72 |
6 | 1223.3 | 47,670 | 90 | 1 | 15.02 | 28.29 | 51.74 | 4.96 |
7 | 611.2 | 13,504 | 88 | 1 | 5.60 | 73.38 | 3.57 | 17.45 |
8 | 1354.8 | 90,166 | 71 | 1 | 8.00 | 6.45 | 85.54 | 0.01 |
9 | 1354.8 | 90,166 | 30 | 1 | 8.00 | 6.45 | 85.54 | 0.01 |
10 | 1520.4 | 100,880 | 30 | 1 | 7.48 | 6.67 | 85.84 | 0.01 |
11 | 1049.7 | 79,150 | 21 | 1 | 1.45 | 3.99 | 94.55 | 0.01 |
12 | 307.0 | 23,151 | 21 | 1 | 1.45 | 3.99 | 94.55 | 0.01 |
13 | 307.0 | 23,151 | 71 | 1 | 1.45 | 3.99 | 94.55 | 0.01 |
14 | 165.6 | 10,715 | 70 | 1 | 3.09 | 8.57 | 88.34 | 0.00 |
15 | 165.6 | 10,715 | 30 | 1 | 3.09 | 8.57 | 88.34 | 0.00 |
16 | 141.4 | 12,436 | 77 | 1 | 0.04 | 0.04 | 99.90 | 0.02 |
17 | 969.4 | 17,464 | 20 | 1 | 0.00 | 100.00 | 0.00 | 0.00 |
18 | 5600.9 | 100,920 | 20 | 1 | 0.02 | 99.97 | 0.00 | 0.01 |
19 | 5600.9 | 100,920 | 20 | 1 | 0.02 | 99.97 | 0.00 | 0.01 |
20 | 6071.6 | 122,650 | 24 | 1 | 5.23 | 85.17 | 9.59 | 0.01 |
21 | 329.8 | 19,187 | 71 | 1 | 33.32 | 5.41 | 61.28 | 0.00 |
22 | 5741.4 | 103,456 | 100 | 1 | 0.02 | 99.96 | 0.00 | 0.02 |
23 | 4631.5 | 83,456 | 100 | 1 | 0.02 | 99.96 | 0.00 | 0.02 |
24 | 4631.5 | 83,456 | 20 | 1 | 0.02 | 99.96 | 0.00 | 0.02 |
25 | 1109.9 | 20,000 | 100 | 1 | 0.02 | 99.96 | 0.00 | 0.02 |
26 | 742.7 | 56,000 | 21 | 1 | 1.45 | 3.99 | 94.55 | 0.01 |
27 | 742.7 | 56,000 | 70 | 1 | 1.45 | 3.99 | 94.55 | 0.01 |
28 | 6071.2 | 122,643 | 70 | 1 | 5.23 | 85.17 | 9.59 | 0.01 |
Stream No. | Molar Flow kmol/h | Mass Flow kg/h | Temp. °C | Pres. Bar | Component Mass % | |||
---|---|---|---|---|---|---|---|---|
Ethanol | Water | Ethyl Acetate | Acetic Acid | |||||
1 | 141.3 | 6511 | 15 | 1 | 100.00 | 0.00 | 0.00 | 0.00 |
2 | 141.1 | 8472 | 15 | 1 | 0.00 | 0.00 | 0.00 | 100.00 |
3 | 282.4 | 14,983 | 15 | 1 | 43.46 | 0.00 | 0.00 | 56.54 |
4 | 282.4 | 14,983 | 70 | 1 | 43.46 | 0.00 | 0.00 | 56.54 |
5 | 1352.7 | 53,292 | 77 | 1 | 27.49 | 22.86 | 29.02 | 20.64 |
6 | 1352.7 | 53,292 | 90 | 1 | 15.29 | 27.62 | 52.34 | 4.74 |
7 | 676.0 | 14,912 | 88 | 1 | 5.86 | 73.55 | 3.67 | 16.93 |
8 | 1493.9 | 98,380 | 70 | 1 | 8.53 | 6.68 | 84.78 | 0.01 |
9 | 1493.9 | 98,380 | 70 | 1 | 8.53 | 6.68 | 84.78 | 0.01 |
10 | 1724.2 | 113,256 | 70 | 1 | 7.86 | 6.93 | 85.21 | 0.01 |
11 | 1189.1 | 87,314 | 27 | 1 | 1.86 | 4.70 | 93.43 | 0.01 |
12 | 372.0 | 27,314 | 27 | 1 | 1.86 | 4.70 | 93.43 | 0.01 |
13 | 372.0 | 27,314 | 71 | 1 | 1.86 | 4.70 | 93.43 | 0.01 |
14 | 230.4 | 14,880 | 70 | 1 | 3.40 | 8.57 | 88.03 | 0.00 |
15 | 230.4 | 14,880 | 70 | 1 | 3.40 | 8.57 | 88.03 | 0.00 |
16 | 141.5 | 12,434 | 77 | 1 | 0.02 | 0.07 | 99.90 | 0.01 |
17 | 970.2 | 17,478 | 20 | 1 | 0.00 | 100.00 | 0.00 | 0.00 |
18 | 6286.9 | 113,276 | 20 | 1 | 0.01 | 99.98 | 0.00 | 0.01 |
19 | 6286.9 | 113,276 | 20 | 1 | 0.01 | 99.98 | 0.00 | 0.01 |
20 | 6821.3 | 139,203 | 41 | 1 | 5.24 | 84.04 | 10.72 | 0.01 |
21 | 394.6 | 23,405 | 71 | 1 | 31.06 | 5.19 | 63.75 | 0.00 |
22 | 6426.7 | 115,797 | 100 | 1 | 0.02 | 99.97 | 0.00 | 0.01 |
23 | 5316.7 | 95,797 | 100 | 1 | 0.02 | 99.97 | 0.00 | 0.01 |
24 | 5316.7 | 95,797 | 20 | 1 | 0.02 | 99.97 | 0.00 | 0.01 |
25 | 1110.0 | 20,000 | 100 | 1 | 0.02 | 99.97 | 0.00 | 0.01 |
26 | 817.1 | 60,000 | 27 | 1 | 1.86 | 4.70 | 93.43 | 0.01 |
27 | 817.1 | 60,000 | 70 | 1 | 1.86 | 4.70 | 93.43 | 0.01 |
28 | 6821.3 | 139,203 | 70 | 1 | 5.24 | 84.04 | 10.72 | 0.01 |
Stream No. | Molar Flow kmol/h | Mass Flow kg/h | Temp. °C | Pres. Bar | Component Mass % | |||
---|---|---|---|---|---|---|---|---|
Ethanol | Water | Ethyl Acetate | Acetic Acid | |||||
1 | 143.2 | 6595 | 15 | 1 | 100.00 | 0.00 | 0.00 | 0.00 |
2 | 141.1 | 8472 | 15 | 1 | 0.00 | 0.00 | 0.00 | 100.00 |
3 | 284.2 | 15,068 | 15 | 1 | 43.77 | 0.00 | 0.00 | 56.23 |
4 | 284.2 | 15,068 | 70 | 1 | 43.77 | 0.00 | 0.00 | 56.23 |
5 | 1296.7 | 51,047 | 77 | 1 | 25.04 | 23.01 | 27.46 | 24.49 |
6 | 1296.7 | 51,047 | 90 | 1 | 12.31 | 27.99 | 51.82 | 7.89 |
7 | 694.0 | 16,516 | 88 | 1 | 5.72 | 65.19 | 4.71 | 24.38 |
8 | 1424.1 | 94,531 | 71 | 1 | 6.84 | 6.81 | 86.35 | 0.00 |
9 | 1424.1 | 94,531 | 70 | 1 | 6.84 | 6.81 | 86.35 | 0.00 |
10 | 1590.0 | 105,218 | 70 | 1 | 6.53 | 6.99 | 86.48 | 0.00 |
11 | 1141.4 | 83,373 | 27 | 1 | 1.88 | 4.86 | 93.26 | 0.00 |
12 | 320.0 | 23,373 | 27 | 1 | 1.88 | 4.86 | 93.26 | 0.00 |
13 | 320.0 | 23,373 | 71 | 1 | 1.88 | 4.86 | 93.26 | 0.00 |
14 | 165.9 | 10,687 | 70 | 1 | 3.80 | 8.57 | 87.64 | 0.00 |
15 | 165.9 | 10,687 | 70 | 1 | 3.80 | 8.57 | 87.64 | 0.00 |
16 | 154.1 | 12,686 | 73 | 1 | 0.26 | 1.74 | 98.00 | 0.00 |
17 | 1533.0 | 27,618 | 20 | 1 | 0.00 | 100.00 | 0.00 | 0.00 |
18 | 5834.7 | 105,212 | 20 | 1 | 0.15 | 99.84 | 0.00 | 0.00 |
19 | 5834.7 | 105,212 | 20 | 1 | 0.15 | 99.84 | 0.00 | 0.00 |
20 | 6283.1 | 127,055 | 41 | 1 | 4.30 | 85.27 | 10.42 | 0.00 |
21 | 318.4 | 19,460 | 71 | 1 | 26.94 | 5.02 | 68.03 | 0.00 |
22 | 5964.8 | 107,594 | 99 | 1 | 0.21 | 99.79 | 0.00 | 0.00 |
23 | 4301.6 | 77,594 | 99 | 1 | 0.21 | 99.79 | 0.00 | 0.00 |
24 | 4301.6 | 77,594 | 20 | 1 | 0.21 | 99.79 | 0.00 | 0.00 |
25 | 1663.1 | 30,000 | 99 | 1 | 0.21 | 99.79 | 0.00 | 0.00 |
26 | 821.4 | 60,000 | 27 | 1 | 1.88 | 4.86 | 93.26 | 0.00 |
27 | 821.4 | 60,000 | 70 | 1 | 1.88 | 4.86 | 93.26 | 0.00 |
28 | 6283.1 | 127,055 | 70 | 1 | 4.30 | 85.27 | 10.42 | 0.00 |
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Rectification Columns | ||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
Heat duty [kW] | R/D | No. of Stages | Feed Stage No. | |||||||||
S1 | S2 | S3 | S1 | S2 | S3 | S1 | S2 | S3 | S1 | S2 | S3 | |
Rectification column SCDS 5 | - | - | - | 0.62 * | 0.61 * | 0.64 * | 8 | 8 | 8 | 8 | 8 | 8 |
Rectification column SCDS 11 | −6593 | −9180.3 | −6611.6 | 3 | 3 | 3 | 35 | 35 | 35 | 15 | 15 | 15 |
6629.8 | 9219.2 | 6629.8 | ||||||||||
Rectification column SCDS 15 | −10,186.5 | −12,127.2 | 10,186.5 | 2 | 2 | 2 | 18 | 18 | 18 | 9 | 9 | 9 |
13,768.6 | 16,136.6 | 13,768.6 | ||||||||||
Reactors | ||||||||||||
Heat Duty [kW] | Process Temperature [°C] | Volume of Apparatus [m3] | ||||||||||
S1 | S2 | S3 | S1 | S2 | S3 | S1 | S2 | S3 | ||||
Reactor evaporator KREA 4 | 12,171.2 | 13,586.2 | 12,747.5 | 85–90 | 85–90 | 85–90 | 300 | 300 | 300 | |||
Extractors | ||||||||||||
Process Temperature [°C] | W/A | |||||||||||
S1 | S2 | S3 | S1 | S2 | S3 | |||||||
Extractor EXTR 8 | 30 | 70 | 70 | 1 | 1 | 1 | ||||||
Heat Exchangers | ||||||||||||
Heat Duty [kW] | ||||||||||||
S1 | S2 | S3 | ||||||||||
Heat exchanger HTXR 2 | 535.6 | 535.6 | 535.6 | |||||||||
Heat exchanger HTXR 6 | −15,658.6 | −14,855.8 | −14,014.1 | |||||||||
Heat exchanger HTXR 10 | 673.4 | 713.5 | 609 | |||||||||
Heat exchanger HTXR 12 | −267.4 | 0 | 0 | |||||||||
Heat exchanger HTXR 17 | −7726.1 | −8869.3 | −8108.6 | |||||||||
Heat exchanger HTXR 18 | 6088 | 4332.9 | 3947.5 | |||||||||
Heat exchanger HTXR 19 | 1595 | 1541.1 | 1562 |
Improved Strategy S1 | Classic Strategy S2 (Heat Duty > S1) | Classic Strategy S3 (Heat Duty = S1) | |
---|---|---|---|
Raw Materials | |||
Ethanol t/tproduct | 0.524 | 0.524 | 0.531 |
Acetic acid t/tproduct | 0.681 | 0.681 | 0.681 |
Process water t/tproduct | 1.42 | 1.42 | 2.18 |
Product | |||
Product quality % | 99.9 | 99.9 | 98.0 |
Energy | |||
Total heating kW/tproduct | 3333.9 | 3704.7 | 3704.7 |
Total cooling kW/tproduct | 3251.1 | 3621.9 | 3621.9 |
Wastewater | |||
Wastewater t/tproduct | 1.61 | 1.61 | 2.36 |
TOC mg/L | 131.7 | 131.7 | 1099.7 |
COD mgO2/L | 470.9 | 470.9 | 4388.4 |
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Piotrowski, W.; Kubica, R. Integration of the Process for Production of Ethyl Acetate by an Enhanced Extraction Process. Processes 2021, 9, 1425. https://doi.org/10.3390/pr9081425
Piotrowski W, Kubica R. Integration of the Process for Production of Ethyl Acetate by an Enhanced Extraction Process. Processes. 2021; 9(8):1425. https://doi.org/10.3390/pr9081425
Chicago/Turabian StylePiotrowski, Wojciech, and Robert Kubica. 2021. "Integration of the Process for Production of Ethyl Acetate by an Enhanced Extraction Process" Processes 9, no. 8: 1425. https://doi.org/10.3390/pr9081425