CIESC Journal ›› 2019, Vol. 70 ›› Issue (2): 533-540.doi: 10.11949/j.issn.0438-1157.20181049

• Process system engineering • Previous Articles     Next Articles

Reaction solvent design method based on Dragon descriptors and modified decision tree-genetic algorithm

Qilei LIU1(),Kun FENG1,Linlin LIU1,Jian DU1,Qingwei MENG2,Lei ZHANG1()   

  1. 1. Institute of Process Systems Engineering，School of Chemical Engineering, Dalian University of Technology, Dalian 116024，Liaoning，China
    2. State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology，Dalian University of Technology, Dalian 116024, Liaoning, China
  • Received:2018-10-16 Revised:2018-11-30 Online:2019-02-05 Published:2018-10-29
  • Contact: Lei ZHANG E-mail:379785365@qq.com;keleiz@dlut.edu.cn

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Abstract:

Reaction solvents have been widely used in liquid-liquid homogeneous organic synthesis. They have significant impacts on reaction rates and selectivity, which have contributed to the development of new process route for green synthesis. A computer-aided molecular design (CAMD) reaction solvent design method based on Dragon descriptor and SMILES (simplified molecular-input line-entry system) coding is proposed. First, a reaction kinetic model was constructed to make quantitative predictions for reaction rate constants k by the decision tree-genetic algorithm (DT-GA). Then, through SMILES code techniques and Dragon software, computer-aided molecular design (CAMD) method was integrated with the DT-GA to establish a mixed integer nonlinear programming (MINLP) model consists of objective functions and constraint equations. Afterwards, a decomposition-based algorithm was employed to solve this MINLP optimization problem, which achieves the objective of reaction solvent design. Finally, an example of Diels-Alder reaction was adapted to demonstrate the feasibility and effectiveness of this method.

Key words: systems engineering, solvents, algorithm, optimization, reaction

CLC Number: 

  • TQ 413.2

Fig.1

Principle of DT-GA method"

Fig.2

CAMD design method integrated with DT-GA"

Table 1

GC method and solvent property constraints"

溶剂性质 基团贡献法公式 上/下限
T m/K T m = 144.0977 l n ( ∑ n i ∈ G n i T m , i ) T m ≤ 303.15
T b/K T b = 244.7889 l n ( ∑ n i ∈ G n i T b , i ) T b ≥ 303.15
S/MPa1/2 S = 20.7339 + ∑ n i ∈ G n i S i 18.05 ≤ S ≤ 22.73
LC50 FM/(mol·L-1) - l n L C 50 F M = ∑ n i ∈ G n i L C 50 , i - l n L C 50 F M ≤ 3.30

Fig.3

Principle of decomposition-based algorithm"

Fig.4

Chemical equation of Diels-Alder reaction between cyclopentadiene and 2-propenal"

Fig.5

Determination coefficients R 2 of 8 types descriptors"

Table 2

Regression data of reaction kinetic model"

溶剂 lgk GATS5p ATS3e ATSC3s ATS3v ATSC1s ATSC2p
乙酸 ?2.491 0.000 2.370 45.125 0.948 15.896 0.498
乙醇 ?2.964 0.000 2.548 13.642 0.868 5.025 0.554
1-丙醇 ?3.186 0.000 3.050 11.757 1.505 3.910 1.145
1-丁醇 ?3.219 0.211 3.382 9.000 1.922 3.000 1.723
甲醇 ?3.257 0.000 1.298 3.000 0.189 4.000 0.113
三氯甲烷 ?3.383 0.000 0.000 0.000 0.000 8.747 0.564
1,2-二氯乙烷 ?3.602 0.000 2.390 16.111 1.286 3.396 1.608
二甲基甲酰胺 ?3.640 0.000 2.824 3.667 1.811 1.917 0.879
二氯甲烷 ?3.699 0.000 0.000 0.000 0.000 5.254 1.101
甲苯 ?3.745 0.625 3.277 6.296 2.400 3.580 2.364
乙腈 ?3.757 0.000 1.453 14.062 0.469 1.937 0.460
1,4-二氧六环 ?3.827 0.000 3.381 14.000 2.039 0.000 1.528
四氯化碳 ?3.873 0.000 0.000 0.000 0.000 5.239 0.014
丙酮 ?3.983 0.000 2.650 27.387 1.311 1.773 1.001
乙酸乙酯 ?4.036 0.954 3.126 27.500 1.849 3.166 1.283

Fig.6

Predicted lgk and experimental lgk "

Table 3

Results of reaction solvents design"

Predicted lgk SMILES 分子结构
?2.269 CCC(Cl)CC(O)COC(C) O
?2.350 CC(CCCC(C)O)C(O)C[N +](O)[O ?]
?2.413 CCCC(C(O)CC)C(Cl)C(C) O
?2.422 CCCCC(C(C)O)C(O)C[N +](O)[O ?]
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