Springer Nature is making Coronavirus research free. View research | View latest news | Sign up for updates

Dechlorination of chlorotoluene rectification residual liquid (CRRL) by using Williamson ether synthesis (WES) method

  • 30 Accesses


Chlorotoluene rectification residual liquid (CRRL) from chlorotolune industry is hard to dispose of because of its high chlorine concentration, which poses high dioxin risk once it is subjected to incinerate. This research employed a chemical approach by using Williamson ether synthesis (WES) method for CRRL dechlorination. It shows that the sodium dosage, the ethanol dosage, and the ultrasonic time are the key factors in chlorine removal. The highest removal rate of chlorine was observed when the sodium dosage, the ethanol dosage, and the ultrasonic time were 0.35 g mL−1, 0.8 mL mL−1, and 15 min, respectively. The further optimization tests indicate that the highest chlorine removal efficiency of 39.06% was observed when the ultrasonic time was 15 min, the sodium dosage and the ethanol dosage were 0.5 g mL−1 and 1.1 mL mL−1, respectively. It suggests a feasible chlorine removal process for organic hazardous waste with high chlorine content before incineration.

This is a preview of subscription content, log in to check access.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6


  1. Altarawneh M et al (2009) Mechanisms for formation, chlorination, dechlorination and destruction of polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs). Prog Energy Combust Sci 35:245–274.

  2. Chen H, Liu S (2015) Cooperative adsorption based kinetics for dichlorobenzene dechlorination over Pd/Fe bimetal. Chem Eng Sci 138:510–515.

  3. Crane RA, Scott TB (2012) Nanoscale zero-valent iron: future prospects for an emerging water treatment technology. J Hazard Mater 211:112–125.

  4. Czaplicka M (2006) Photo-degradation of chlorophenols in the aqueous solution. J Hazard Mater 134:45–59.

  5. Diaz E et al (2011) Comparison of activated carbon-supported Pd and Rh catalysts for aqueous-phase hydrodechlorination. Appl Catal B Environ 106:469–475.

  6. Gao X, Ji B, Huang Q (2016) Thermal dechlorination of heavily PCB-contaminated soils from a sealed site of PCB-containing electrical equipment. Environmental Science and Pollution Research 23 (15):15544–15550

  7. Janiak T (2008) Kinetics of o-chlorotoluene hydrogenolysis in the presence of 3%, 5% and 10% Pd/C catalysts. Appl Catal A Gen 335:7–14.

  8. Janiak T, Blazejowski J (2002) Hydrogenolysis of chlorobenzene, dichlorobenzenes and chlorotoluenes by in situ generated and gaseous hydrogen in alkaline media and the presence of Pd/C catalyst. Chemosphere. 48:1097–1102.

  9. Ma R et al (2016) Adsorptive removal of organic chloride from model jet fuel by Na-LSX zeolite: kinetic, equilibrium and thermodynamic studies. Chem Eng Res Des 114:321–330.

  10. Ndong LBB et al (2014) Efficient dechlorination of chlorinated solvent pollutants under UV irradiation by using the synthesized TiO2 nano-sheets in aqueous phase. J Environ Sci 26:1188–1194.

  11. Rybnikova V, Usman M, Hanna K (2016) Removal of PCBs in contaminated soils by means of chemical reduction and advanced oxidation processes. Environmental Science and Pollution Research 23 (17):17035–17048

  12. Sui H, Rong Y, Song J, Zhang D, Li H, Wu P, Shen Y, Huang Y (2018) Mechanochemical destruction of DDTs with Fe-Zn bimetal in a high-energy planetary ball mill. Journal of Hazardous Materials 342:201–209.

  13. Tak BY et al (2015) Min, optimization of color and COD removal from livestock wastewater by electrocoagulation process: application of Box-Behnken design (BBD). J Ind Eng Chem 28:307–315.

  14. Tian Y et al (2017) Sulfite promoted photochemical cleavage of s-triazine ring: the case study of atrazine. Chem Eng J 330:1075–1081.

  15. Ukisu Y et al (1997) Hydrogen-transfer Hydrodehalogenation of aromatic halides with alcohols in the presence of Noble metal catalysts. J Mol Catal A Chem 125:135–142.

  16. Ukisu Y et al (2000) Miyadera, catalytic dechlorination of aromatic chlorides with noble-metal catalysts under mild conditions: approach to practical use. Appl Catal B Environ 27:97–104.

  17. Williamson AJPM, XLV (1850) Theory of ætherification. Philos Mag 37:350–356.

  18. Zhao X et al (2016) An overview of preparation and applications of stabilized zero-valent iron nanoparticles for soil and groundwater remediation. Water Res 100:245–266.

  19. Zubero MB et al (2017) Changes in serum dioxin and PCB levels in residents around a municipal waste incinerator in Bilbao, Spain. Environ Res 156:738–746.

Download references


The authors acknowledge Zhejiang Weihua Chemical Co., Ltd. for providing the CRRL sample.


This work was financially supported by the National Natural Science Foundation of China (51778579 and 21876165) and Natural Science Foundation of Zhejiang Province (LY18B070009).

Author information

Correspondence to Yuyang Long.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Responsible editor: Philippe Garrigues

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Long, Y., Jin, Z., Li, L. et al. Dechlorination of chlorotoluene rectification residual liquid (CRRL) by using Williamson ether synthesis (WES) method. Environ Sci Pollut Res (2020).

Download citation


  • Chlorine removal
  • Rectification residue
  • Sodium alcoholate
  • Ultrasonic processing
  • Response surface methodology