A process for the synthesis of a carbon labeled organic compound containing a carbon labeled carboxyl group is described. A method of using carbon labeled organic compounds containing a carbon labeled carboxyl group according to the present disclosure; a process for manufacturing labeled pharmaceuticals and agrochemicals comprising synthesis of carbon labeled organic compounds containing a carbon labeled carboxyl group according to the present disclosure; and a process for producing tracers comprising synthesis of carbon labeled organic compounds containing a carbon labeled carboxyl group according to the present disclosure are also described.

A method of increasing a density of carboxylic acids on a surface of a carbon nanoparticle is disclosed. The method includes contacting an oxygen-containing functional group on a surface of a carbon nanoparticle with a reducing agent to provide a hydroxyl group; reacting the hydroxyl group with a diazoacetate ester in the presence of a transition metal catalyst to provide an ester, the diazoacetate ester having the structure wherein R is a C1-8 hydrocarbyl, preferably tert-butyl, methyl, ethyl, isopropyl, allyl, benzyl, pentafluorophenyl, or N-succinimidyl; and cleaving the ester to provide a carboxylic acid group. Surface-functionalized carbon nanoparticles made by the method are also disclosed.

A method of increasing a density of carboxylic acids on a surface of a carbon nanoparticle is disclosed. The method includes contacting an oxygen-containing functional group on a surface of a carbon nanoparticle with a reducing agent to provide a hydroxyl group; reacting the hydroxyl group with a diazoacetate ester in the presence of a transition metal catalyst to provide an ester, the diazoacetate ester having the structure wherein R is a C1-8 hydrocarbyl, preferably tert-butyl, methyl, ethyl, isopropyl, allyl, benzyl, pentafluorophenyl, or N-succinimidyl; and cleaving the ester to provide a carboxylic acid group. Surface-functionalized carbon nanoparticles made by the method are also disclosed.

The present disclosure provides method for isolating a long chain dicarboxylic acid such as a substantially pure or pure long chain dicarboxylic acid from a fermentation broth containing microbial cells.

The present disclosure provides method for isolating a long chain dicarboxylic acid such as a substantially pure or pure long chain dicarboxylic acid from a fermentation broth containing microbial cells.

A process for the preparation of cis-2-alkenoic acid or an alkali metal salt thereof, comprising rearranging 1,3-dibromo-2-alkanone in an alkaline environment in the presence of a catalytically effective amount of an alkali metal salt of cis-2-alkenoic acid, and isolating from the reaction mixture cis-2-alkenoic acid, either in the form of the free acid or in the form of the alkali metal salt.

A process for the preparation of cis-2-alkenoic acid or an alkali metal salt thereof, comprising rearranging 1,3-dibromo-2-alkanone in an alkaline environment in the presence of a catalytically effective amount of an alkali metal salt of cis-2-alkenoic acid, and isolating from the reaction mixture cis-2-alkenoic acid, either in the form of the free acid or in the form of the alkali metal salt.

Methods for producing cycloaddition products comprising: reacting a diene with a dienophile in the presence of one or more boron-based catalysts of Formula I or Formula II are provided. In particular, the methods can be used to prepare 4-methyl-3-cyclohexene-1-carboxylic acid and 3-methyl-3-cyclohexene-1-carboxylic acid, including bio-based versions thereof. The cycloaddition products can be advantageously used in the production of terephthalic acid and isophthalic acid, and ultimately, poly(ethylene terephthalate), and bio-based versions thereof. ##STR00001##
BOBL.sub.4Formula II

Methods for producing cycloaddition products comprising: reacting a diene with a dienophile in the presence of one or more boron-based catalysts of Formula I or Formula II are provided. In particular, the methods can be used to prepare 4-methyl-3-cyclohexene-1-carboxylic acid and 3-methyl-3-cyclohexene-1-carboxylic acid, including bio-based versions thereof. The cycloaddition products can be advantageously used in the production of terephthalic acid and isophthalic acid, and ultimately, poly(ethylene terephthalate), and bio-based versions thereof. ##STR00001##
BOBL.sub.4Formula II

A method of reducing an aromatic ring or a cyclic, allylic ether in a compound includes preparing a reaction mixture including a compound including an aromatic moiety or a cyclic, allylic ether moiety, an alkali metal, and either ethylenediamine, diethylenetriamine, triethylenetetramine, or a combination thereof, in an ether solvent; and reacting the reaction mixture at from 20 C. to 30 C. for a time sufficient to reduce a double bond in the aromatic moiety to a single bond or to reduce the cyclic, allylic ether moiety.