http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2016028851-A1

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filingDate 2015-08-19-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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publicationDate 2016-02-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber WO-2016028851-A1
titleOfInvention Esterified anhydropentitols and methods of making the same
abstract Amphipathic amine-esters derived from anhydropentitols are prepared through a short sequence of synthetic steps. The process is initiated by the esterification of an anhydropentitol with a fatty acid chloride or a lipase enzyme to form anhydropentitol fatty acid esters, preferably leaving at least one free hydroxyl. The free hydroxyl group(s) are then sulfonated, forming sulfonated anhydropentitol fatty acid esters. The sulfonyl moiety on the sulfonated anhydropentitol fatty acid esters are then subject to nucleophilic displacement by a hydrophilic moiety, illustrated by a primary amine such as AEE or AEEA. The synthetic pathway is efficient and affords modest to high yields of target amphiphilic compounds, which are useful at least as surfactants and plasticizer substitutes for petroleum derived compounds.
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