Trans-1,2-Dichloroethene: Properties, Industrial Applications, and Advances in Separation Technologies
Aug 29,2025
Abstract
1,2-Dichloroethene exists in isomeric forms, and the trans-1,2-Dichloroethene configuration has significant industrial applications. Therefore, effective methods for separating the cis and trans isomers are of great importance.
cis–trans isomer
Both trans-1,2-Dichloroethene and cis-1,2-dichloroethylene are colorless transparent oily liquids at room temperature, with melting points of -49.44°C and -81.47°C and boiling points of 47.7°C and 60.2°C respectively. They are slightly toxic and pleasant odor. In case of humidity, sunlight and air, it will gradually decompose and release hydrogen chloride. Soluble in alcohol, ether and other organic solvents, insoluble in water. Compared with cis-1,2-dichloroethylene, trans-1,2-dichloroethylene is less toxic and chemically active. It is mainly used in the industry as an extractant for heat-sensitive substances or as a solvent for certain polymer materials and organic Synthetic raw materials.[1]
Efficient Separation of cis- and trans-1,2-Dichloroethene Isomers
Cis- and trans-1,2-Dichloroethene (cis-DCE and trans-DCE) isomers are important chemical feedstocks in the modern chemical industry. In polymer science, each isomer has been widely copolymerized with other ethylenically unsaturated monomers to construct copolymer materials with specific properties (e.g., improved processability and impact resistance). They have been used as low-temperature extraction solvents for rubber, waxes, resins, lacquers, thermoplastics, etc. trans-DCE is marketed as an environmentally friendly refrigerant. cis-DCE is a foam blowing additive. The boiling points of cis- and trans-DCE isomers are close. In industry, they are separated by fractional distillation with very high columns.
Adaptive Biphen arene Crystals Saperation
Industrially important cis- and trans-1,2-dichloroethene (cis-DCE and trans-DCE) isomers can be highly efficient seperated by activated crystalline 2,2’,4,4’-tetramethoxyl biphen arene (MeBP3) materials, MeBP3a. MeBP3 can be synthesized in excellent yield (99 %), and a cyclic pentamer is also obtained when using 1,2-dichloro-ethane as the solvent. The structure of MeBP3 in the CH3CN@MeBP3 crystal displays a triangle-shape topology, forming 1D channels through window-to-window packing. Desolvated crystalline MeBP3 materials, MeBP3a, preferentially adsorb cis-DCE vapors over its trans isomer. MeBP3a is able to separate cis-DCE from a 50:50 (v/v) cis/trans-isomer mixture, yielding cis-DCE with a purity of 96.4 % in a single adsorption cycle. Single-crystal structures and powder X-ray diffraction patterns indicate that the uptake of cis-DCE triggers a solid-state structural transformation of MeBP3, suggesting the adaptivity of MeBP3a materials during the sorption process. Moreover, the separation can be performed over multiple cycles without loss of separation selectivity and capacity. [2]
Highly selective molecular sieving
Trianglimine macrocycles are a class of intrinsically porous materials that can be easily prepared and scaled up for selective separations. A trianglimine macrocycle that can be used as a molecular sieve for efficient and successful separation of cis-DCE from an equimolar cis/trans-DCE mixture in both liquid and vapor phases. The naphthalene sidewall increases the rigidity of the macrocycle and guest binding ability.29,30 Meanwhile, the removal of the trapped guests could transform the macrocycle 1 crystals back to the original guest-free form, endowing the macrocycle with excellent recyclability and reversibility [3]
Selective complexation and efficient separation by a pillar arene
Pillar[n]arenes, as important family of supramolecular macrocycles with prism-like geometries and π-rich cavities, have shown interesting cavity host–guest properties towards a variety of guest molecules. The most peculiar complexation behavior of pillar[n]arenes is that pillar arenes can strongly bind suitable neutral molecules in organic solution compared with other popular macrocycles. cis-/trans-selective complexation of industrially important DCE isomers by EtP5 macrocycle both in solution and in the solid state. Its adaptive crystals, EtP5α, are able to efficiently separate trans-DCE from a cis- and trans-DCE isomers mixture. The selectivity derives from the size/shape-fit host–guest complexation and the vapor-induced crystalline structure transformation.[4]
References:
[1] Tomé, C. (2017, June 15). The tautomerization of porphycene on Cu(111) in simple physical terms. Mapping Ignorance. Retrieved August 15, 2025
[2] Wang, Y., Xu, K., Li, B., Cui, L., Li, J., Jia, X., ... & Li, C. (2019). Adaptive biphenyl[3]arene crystals for efficient separation of cis- and trans-1,2-dichloroethene isomers. Angewandte Chemie, 131(30), 10387–10390.
[3] Liu, X., Alimi, L. O., & Khashab, N. M. (2022). Highly selective molecular sieving of cis- over trans-1,2-dichloroethene isomers. Chemical Communications, 58(65), 9369–9372. https://doi.org/10.1039/D2CC03574J
[4] Li, B., Xu, K., Wang, Y., Su, H., Cui, L., & Li, C. (2020). Selective complexation and efficient separation of cis/trans-1,2-dichloroethene isomers by a pillar[5]arene. RSC Advances, 10, 45112–45115.
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