Synthesis and Characterization of Trimesoylamidoamine†

doi:10.7503/cjcu20150957

Abstract

Abstract:

Trimesoylamidoamine(TMAAM) is a novel compound, which can be used as a key functional monomer to fabricate antifouling and chlorine-tolerant polyamide reverse osmosis membrane by interfacial polymerization. Trimesoyl chloride(TMC) and 1,3-diamino-2-propanol(DAP) were used as raw materials to synthesize TMAAM via three-step method including esterification, amidation and ester aminolysis reactions successively. The effects of methanol dosage, type and amount of the acid binding agent, and DAP dosage on the reactions were discussed. The reaction mechanism of ester aminolysis was also explored. The chemical structure of TMAAM was identified via infrared spectra(IR), nuclear magnetic resonance(NMR) and high-resolution mass spectragraph(HRMS). This three-step method has some advantages including mild reaction conditions, easy operation, convenient post treatment and favorite reaction economy. The top total product yield of three reactions was 57%.

Key words: Trimesoylamidoamine, 1,3-Diamino-2-propanol, Trimesoyl chloride, Composite acid binding agent(Ed.: W, Z)

TrendMD:

CHEN Xiaolin, WU Hao, LIU Lifen, GAO Congjie. Synthesis and Characterization of Trimesoylamidoamine^†[J]. Chem. J. Chinese Universities, 2016, 37(5): 983.

Figures/Tables 7

Scheme 1 Synthetic routes of compound TMAAM

Fig.1 Effects of CH3OH dosages on the yield of MOCPCAP

Table 1 Effects of acid binding agent varieties on the reaction time and the yield of MOCPCAP

Acid binding agent	Reaction time/h	Yield(%)	Acid binding agent	Reaction time/h	Yield(%)
Catalyst-free	2.5	20	Triethylamine(TEA)/DMF	2	53
Triethylamine(TEA)	2	45	Imidazole/Pyridine	2	45
Imidazole	2	45	Na₂CO₃	2.5	19
Pyridine	2	48	NaOH	2.5	15

Fig.2 Effects of acid binding agent dosages on the yield of MOCPCAP

Scheme 2 Ester group amidation reaction proposed mechanism

Fig.3 Effects of DAP dosages on the yield of TMAAM

Scheme 3 Structure of TMAAM

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