Efficient synthesis of 1,6-hexamethylene diurethane through coupling transesterification and methoxycarbonylation with methyl phenyl carbonate as intermediate

Yong Yang; Jihai Tang; Xian Chen; Zhaoyang Fei; Mifen Cui; Xu Qiao

doi:10.1016/j.cjche.2014.11.033

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Efficient synthesis of 1,6-hexamethylene diurethane through coupling transesterification and methoxycarbonylation with methyl phenyl carbonate as intermediate

催化、动力学与反应工程 | Updated：2026-01-06

- Efficient synthesis of 1,6-hexamethylene diurethane through coupling transesterification and methoxycarbonylation with methyl phenyl carbonate as intermediate
- Chinese Journal of Chemical Engineering Vol. 23, Issue 7, Pages: 1147-1152(2015)
- Affiliations：
  
  1. 2 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University,Nanjing,China,210009
  2. 3 College of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaiyin,China,223003
- Author bio：
- Funds：
- DOI：10.1016/j.cjche.2014.11.033
  CLC：
- Published：2015
- Accepted：
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Yong Yang, Jihai Tang, Xian Chen, Zhaoyang Fei, Mifen Cui, Xu Qiao. Efficient synthesis of 1,6-hexamethylene diurethane through coupling transesterification and methoxycarbonylation with methyl phenyl carbonate as intermediate[J]. Chin.J.Chem.Eng., 2015, 23(7): 1147-1152.
DOI：

Yong Yang, Jihai Tang, Xian Chen, Zhaoyang Fei, Mifen Cui, Xu Qiao. Efficient synthesis of 1,6-hexamethylene diurethane through coupling transesterification and methoxycarbonylation with methyl phenyl carbonate as intermediate[J]. Chin.J.Chem.Eng., 2015, 23(7): 1147-1152. DOI： 10.1016/j.cjche.2014.11.033.

摘要

Abstract

A reaction coupling system of transesterification and methoxycarbonylation with methyl phenyl carbonate (MPC) as intermediate was established to efficiently prepare 1

6-hexamethylene diurethane (HDU) from 1

6-hexamethylene diamine (HDA). The feasibility of the system was explored using the thermodynamics analysis

the reaction mechanism and the experiment results. The optimal reaction was carried out to get higher HDU yield. The thermodynamic analysis showed that the methoxycarbonylation of HDA with MPC

the Gibbs free energy of which was negative

was a spontaneous process. Furthermore

the equilibrium constant of the methoxycarbonylation of HDA with MPC was much greater than that of the transesterification of dimethyl carbonate (DMC) with phenol

so the reaction coupling could be realized under mild conditions. The reaction mechanismanalysis indicated that phenoxy anion was the key species for reaction coupling. HigherMPC concentration was detected when sodium phenoxide was used as transesterification reactant with DMC

since the phenoxy anion of sodium phenoxide could be dissociated more easily. Sodium phenoxide was more suitable to prepare HDU through reaction coupling. A

yield of HDU as high as 98.3% could be reached under the optimal conditions of m

PhONa

DMC

= 0.027 and n

DMC

HDA

= 8/1 at 90 ℃ in 2 h.

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