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Biomass-Derived Poly(ether-amide)s Incorporating Hydroxycinnamates
Brianna M Upton1, Andrea M Kasko2
1Department of Chemistry and Biochemistry , University of California, Los Angeles , Los Angeles , California 90095 , United States.
Abstract:
Lignin-derived chemicals have great potential as feedstock to produce polymeric materials, due to the low cost and high abundance of lignin biomass. Lignin is one of the few nonpetroleum sources of aromatic carbon, a desirable moiety in high-performance polymers. Herein we describe the synthesis and characterization of a series of 21 poly(ether-amide)s that incorporate hydroxycinnamates derived from lignin. Three different hydroxycinnamates (coumaric acid, ferulic acid, sinapinic acid) were incorporated into dimers, and then copolymerized with a series of seven aliphatic and aromatic diamines via interfacial polymerization. The resultant polymers exhibited poor solubility in standard organic solvents (excluding DMF), but exhibited moderate glass transition temperatures and moderate thermal stabilities. Additionally, the polymers exhibit excellent resistance to hydrolysis. The modularity of this synthetic approach could be used to rapidly generate diverse polymers with a broad range of well-tuned properties.
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01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
01:29Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
02:36Crown Ethers
02:28Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
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02:17Physical Properties of Ethers
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
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