C-glycoside amine derivatives and methods of making
Inventors
Jackson, Michael A. • Price, Neil P.
Assignees
United States, Represented Secretary Of Agriculture AS • US Department of Agriculture USDA
Publication Number
US-11192913-B2
Publication Date
2021-12-07
Expiration Date
2041-01-04
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Abstract
Disclosed are C-glycoside amine derivatives of the formula: R—CH2—C(CH3)—NH—R2 wherein R is a saccharide (e.g., as described in U.S. Pat. No. 8,314,219) and R2 is an acyl moiety derived from any ketone of the formula R3—C(O)—R3 wherein R3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated. In addition, a method for making the C-glycoside amine derivatives involving (1) reacting a saccharide (e.g., glucose) C-glycoside ketone with a catalyst (e.g., Rh), about 10 to about 25 fold excess NH3, and an organic solvent (e.g., methanol) to form a saccharide C-glycoside amine, and (2) reacting said saccharide C-glycoside amine with a catalyst (e.g., Rh), an organic solvent (e.g., methanol), and an acyl moiety derived from any ketone of the formula R3—C(O)—R3 wherein R3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated to form said C-glycoside amine derivative.
Core Innovation
The invention discloses C-glycoside amine derivatives with the formula R—CH2—C(CH3)—NH—R2, where R is a saccharide and R2 is an acyl moiety derived from ketones with C1 to C22 straight or branched chain hydrocarbons. It also describes compositions containing these derivatives and a two-step method for producing them: first, reacting a saccharide C-glycoside ketone with a catalyst (e.g., Rh), excess NH3, and an organic solvent to form a saccharide C-glycoside amine; second, reacting this amine with a catalyst, solvent, and the acyl moiety from a ketone to form the C-glycoside amine derivative.
The background identifies the increasing demand for biobased and sustainable chemicals, especially sugar-based surfactants composed of hydrophilic sugar head groups and hydrophobic alkyl tails. These surfactants are used as biodegradable emulsifiers in multiple industries but have limitations such as nonspecific regioselectivity in chemical esterification, the need for harsh solvents, acid chlorides, long reaction times, or complex catalyst systems in their synthesis.
This invention solves these problems by providing novel surfactants prepared from β-C-glycoside amines and medium chain ketones, with the sugar head groups derived from abundant or waste saccharides and the hydrophobic tails derived from ketonization of triacylglycerides from renewable sources. The methods employ reductive amination under mild conditions using Rh catalysts, avoiding the limitations and harsh conditions of known methods.
Claims Coverage
The patent contains three independent claims focusing on the compound, composition, and method of making the C-glycoside amine derivatives. The main inventive features are as follows.
C-glycoside amine derivative composition
A C-glycoside amine derivative of the formula R—CH2—C(CH3)—NH—R2 wherein R is a saccharide and R2 is an acyl moiety derived from any ketone R3—C(O)—R3 with R3 being a C1 to C22 straight or branched chain hydrocarbon, which may be saturated or unsaturated.
Composition containing C-glycoside amine derivatives
A composition comprising at least one C-glycoside amine derivative of the defined formula, optionally including a carrier.
Method for making C-glycoside amine derivatives
A two-step method involving: (1) reacting a saccharide C-glycoside ketone with a catalyst (e.g., Rh), about 10 to 25 fold excess NH3, and an organic solvent to produce a saccharide C-glycoside amine, and (2) reacting this amine with a catalyst, organic solvent, and an acyl moiety from a ketone R3—C(O)—R3 (C1 to C22 hydrocarbons) to yield the C-glycoside amine derivative.
The claims cover the novel compound structure of C-glycoside amine derivatives, compositions comprising these compounds, and an innovative mild reductive amination method using excess ammonia and Rh catalysts to form these derivatives with acyl moieties derived from a broad range of ketones.
Stated Advantages
The invention avoids the use of homogeneous catalysts, acid chlorides, harsh solvents, and long reaction times typical in known sugar ester preparation methods.
It produces biodegradable surfactants from abundant or waste-derived saccharides and renewable hydrophobic ketone sources.
The reductive amination method achieves high selectivity for primary amines avoiding secondary amine or dimer formation by using excess ammonia.
The resulting surfactants exhibit low critical micelle concentrations and surprising antimicrobial activity against diverse microorganisms with low minimum inhibitory concentrations.
Documented Applications
Use as biodegradable emulsifiers and surfactants in food, cosmetic, pharmaceutical, and detergent products.
Potential antibiotic activity applications against microorganisms relevant to food safety, human health, and agriculture.
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