Abstract: A lubricating composition containing one or more esters obtained as a reaction product from a reaction mixture of a glycerol component, a fatty acid component, and a carboxylic acid component wherein said glycerol component comprises glycerol, glycerol oligomers, or combinations thereof and further wherein said glycerol oligomers comprise linear chains, branched chains, cyclic chains, or combinations thereof and further wherein said glycerol oligomers have at least 2 repeat glycerol units and further no more than about 32 repeat glycerol units; wherein said fatty acid component comprises alkyl groups having at least about 8 carbon atoms and further wherein said alkyl groups have no more than about 32 carbon atoms; wherein said carboxylic component has at least one carbon atom per molecule and no more than about 8 carbon atoms per molecule; and wherein the fatty acid component comprises at least 50 percent by weight of the fatty acid component of oleic acid; wherein the fatty acid component comprises at least

Abstract: The present invention comprises the use of hexamethylene diamine (HMDA) and its salts formed with organic or inorganic acids as an inhibitor for shales and clay found in drilling and producing petroleum oil and gas wells. When HMDA is added to the aqueous base of a drilling fluid, the resultant mixture inhibits shale and clays to impart and/or increase permanent permeability stability in reservoirs. Thus, with the use of the present invention, a more environmentally acceptable, chloride free, water base drilling fluid may be used in place of an oil base drilling fluid, or fluid with the heretofor more commonly used potassium additives. The present invention may be used as a completion fluid, and as a drill-in fluid.