Study on the Structure of Cu/ZrO2 Catalyst and the Formation Mechanism of Disodium Iminodiacetate and Sodium Glycine

  • Yongsheng Wang
  • Hongwen Zhu
  • Zhengkang DuanEmail author
  • Zhenzhen Zhao
  • Yunlu Zhao
  • Xiaolin Lan
  • Li Chen
  • Dongjie Guo


A new method to prepare Cu/ZrO2 catalysts by reducing CuO/ZrO2 with hydrazine hydrate is reported, and the prepared catalysts were used to synthesize disodium iminodiacetate by diethanolamine dehydrogenation. Hydrazine hydrate can rapidly reduce the CuO/ZrO2 precursor powder in an alkaline environment at a moderate temperature. The ratio of Cu0/Cu+ at the Cu/ZrO2 surface was controlled by the amount of hydrazine hydrate and the reduction reaction time. The formation mechanism of disodium glycine as the main byproduct and iminodiacetate were deduced by investigating the product yield, the reaction time, and the presence of acetaldehyde in the evolved gas. It has been shown that the ratio of Cu0/Cu+ in Cu/ZrO2 significantly affects the dehydrogenation of diethanolamine into disodium iminodiacetate. Cu0 and Cu+ are the catalytic activity centers in the dehydrogenation of diethanolamine which respectively produce intermediate aldehydes and an ester via nucleophilic addition reactions. The formation mechanism of sodium glycinate is related to the tautomerism of intermediate products and Schiff base hydrolysis.

Graphic Abstract

The formation mechanism of disodium iminodiacetate and sodium glycine producing by the dehydrogenation of diethanolamine over the Cu/ZrO2 catalysts which were prepared by a new reduction method.


Copper-zirconium catalysts Diethanolamine Disodium iminodiacetate Reaction mechanism Hydrazine hydrate 



Support from the National Natural Science Foundation of China (Grant No. NSFC 21576229) is gratefully acknowledged.

Compliance with Ethical Standards

Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

10562_2019_2989_MOESM1_ESM.docx (17 kb)
Electronic supplementary material 1 (DOCX 17 kb)


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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Yongsheng Wang
    • 1
    • 2
  • Hongwen Zhu
    • 1
  • Zhengkang Duan
    • 1
    • 2
    Email author
  • Zhenzhen Zhao
    • 1
    • 2
  • Yunlu Zhao
    • 1
    • 2
  • Xiaolin Lan
    • 1
  • Li Chen
    • 1
  • Dongjie Guo
    • 1
  1. 1.College of Chemical EngineeringXiangtan UniversityXiangtanChina
  2. 2.Hunan Collaborative Innovation Center of New Chemical Technologies for Environmental Benignity and Efficient Resource UtilizationXiangtanChina

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