Synthesis and properties of green sustainable carbonate-type nonionics containing polyoxyethylene chains.

A series of polyoxyethylene surfactants containing carbonate linkages as biodegradable and chemically recyclable segments was designed and synthesized by a green process. A two-step carbonate exchange reaction was used: dimethyl or diphenyl carbonate was reacted with 1-alkanol, and the product was reacted with poly (ethylene) glycol in the presence of a lipase or chemical catalyst. The obtained carbonate-type nonionics exhibited good surface-active properties such as a low critical micelle concentration value and a surface tension lowering action. They were readily biodegraded by activated sludge, furthermore, could be chemical recycled using a lipase.

[1]  K. Toshima,et al.  Synthesis and properties of polycarboxylate-type green surfactants with S- or N-linkages. , 2009, Journal of oleo science.

[2]  K. Toshima,et al.  Synthesis and Properties of Gemini-type Cationic Surfactants Containing Carbonate Linkages in the Linker Moiety Directed Toward Green and Sustainable Chemistry , 2009 .

[3]  B. Trost,et al.  The atom economy--a search for synthetic efficiency. , 1991, Science.

[4]  M. Arai,et al.  Synthesis of dimethyl carbonate from carbon dioxide and methanol in the presence of methyl iodide and base catalysts under mild conditions: effect of reaction conditions and reaction mechanism , 2001 .

[5]  K. Holmberg,et al.  Hydrolyzable nonionic surfactants: stability and physicochemical properties of surfactants containing carbonate, ester, and amide bonds. , 2005, Journal of colloid and interface science.

[6]  Zhimin Liu,et al.  Synthesis of dimethyl carbonate using CO2 and methanol: enhancing the conversion by controlling the phase behavior , 2002 .

[7]  K. Holmberg,et al.  Hydrolysis and biodegradation studies of surface-active esters , 2003 .

[8]  Hiroyuki Yasuda,et al.  Selective and high yield synthesis of dimethyl carbonate directly from carbon dioxide and methanol , 2002 .

[9]  Barry M. Trost,et al.  Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way , 1995 .

[10]  T. Kida,et al.  Novel hydrolyzable and biodegradable cationic gemini surfactants: 1,3-bis[(acyloxyalkyl)-dimethylammonio]-2-hydroxypropane dichloride , 2000 .

[11]  L. Lemiègre,et al.  Glycine betaine as a renewable raw material to “greener” new cationic surfactants , 2008 .

[12]  K. Toshima,et al.  Synthesis and properties of biodegradable and chemically recyclable cationic surfactants containing carbonate linkages. , 2007, Journal of oleo science.

[13]  K. Holmberg,et al.  Synthesis, stability, and biodegradability studies of a surface-active amide , 2005 .

[14]  K. Holmberg,et al.  Cationic ester-containing gemini surfactants: chemical hydrolysis and biodegradation. , 2007, Journal of colloid and interface science.

[15]  T. Kida,et al.  Novel hydrolyzable and biodegradable cationic gemini surfactants: Bis(ester-ammonium) dichloride having a butenylene or a butynylene spacer , 2001 .

[16]  M. J. Rosen,et al.  Relationship of structure to properties in surfactants. 9. Syntheses and properties of 1,2- and 1,3-alkanediols , 1980 .

[17]  K. Holmberg,et al.  Synthesis and chemical hydrolysis of surface-active esters , 2003 .

[18]  B. Różycka-Roszak,et al.  Calorimetric studies of the micellization of some amphiphilic betaine ester derivatives , 1988 .