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Efficient Processes to Produce Polyalkylated Oligo-ethyl-polyamines

Detailed Technology Description

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Supplementary Information

Patent Number: US8658829B2
Application Number: US13522803A
Inventor: Elangovan, Arumugasamy
Priority Date: 8 Feb 2010
Priority Number: US8658829B2
Application Date: 18 Jul 2012
Publication Date: 25 Feb 2014
IPC Current: C07C020960
US Class: 564481 | 564511 | 564512
Assignee Applicant: NDSU Research Foundation,Fargo
Title: Method of producing polyalkylated oligoalkylenepolyamines
Usefulness: Method of producing polyalkylated oligoalkylenepolyamines
Summary: The process is useful for preparing polyalkylated oligoalkylenepolyamine, which is: a pentaalkyldialkylenetriamine, e.g. a pentaalkyldiethylenetriamine or pentaalkyldipropylenetriamine; tetraalkylalkylenediamine, e.g. a tetraalkylethylenediamine or tetraalkylpropylenediamine; a penta-(n-alkyl)-diethylenetriamine and/or tetra-(n-alkyl)-ethylenediamine; N,N,N',N'',N'''-pentaethyldiethylenetriamine; N,N,N',N''-tetraethylethylenediamine; or penta-(n-alkyl)-dipropylenetriamine and/or tetra-(n-alkyl)-propylenediamine (claimed). The polyalkylated oligoalkylenepolyamine is useful as: ligands in a variety of chemical transformations, e.g. as ligands for metal species in homogeneous atom transfer radical polymerization reactions; and antiwear lubrication additives.
Novelty: Preparing polyalkylated oligoalkylenepolyamine comprises contacting oligoalkylenepolyamine with reagent composition comprising alkyl bromide/alkyl chloride, basic agent e.g. potassium carbonate, and iodide salt e.g. potassium iodide

Industry

Chemical/Material

Sub Category

Chemical/Material Application

*Abstract

Certain Polyalkylated Oligo-ethyl-polyamines such as TMEDA, TEEDA and PEDETA are useful intermediates in organic synthesis and analytical chemistry and used extensively in inorganic chemistry as ligands for a variety of metal complexes. In spite of high demands, PEDETA (penta-ethyl-di-ethylene-triamne) has not been available in industrial scales due to the difficulty in the realization of complete alkylation of the starting material using conventional methods. This novel method describes a process of obtaining PEDETA that is pure and without any side or incomplete alkylated product. The process involves no work-up and is thus environmentally friendly. In addition, the reaction time and work-up process is drastically reduced from the conventional synthesis method.

Country/Region

USA