Vinyl Ether Carboxylic Acid

Acetic acid adds in the presence of palladium catalysts to give ethylidene diacetate ch 3 ch oac 2.

Vinyl ether carboxylic acid.

Carboxylic acids without the need for derivatives or scavengers would be preferred for the synthesis of vinyl ether functional esters. Acid vinyl ether poly carboxylic acid prior art date 1990 04 10 legal status the legal status is an assumption and is not a legal conclusion. Carboxylic acid pka 4 5 4. Most of blocked carboxylic acids obtained were liquid.

A vinyl ether functionalized cyclic carbonate monomer 5 methyl 5 2 vinyloxy ethyl oxycarbonyl 1 3 dioxan 2 one mvec 2 was synthesized by a well established two step procedure from bis mpa. This would for example allow for fatty acids or other carboxylic acids to be used which can make the vinyl ether monomers more bio based 14 15 in this work we present a novel method that can be used to. Vinyl ethers are attractive alternatives to meth acrylates due to low allergenic hazards low toxicity and fast polymerization. 22 23 esterification of bis mpa with 2 chloroethyl vinyl ether followed by cyclization using ethyl chloroformate yielded cyclic carbonate monomer.

The facile general acid catalyzed conversion of 2 ethoxy 1 cyclopentene 1 carboxylic acid to cyclopentanone. The reaction of saturated carboxylic acids with vinyl ethers gave the corresponding esters. The reaction of vinyl ethers with carboxylic acids using iodine as a catalyst under solvent free conditions was investigated. Tan 2 yl acetic acid 12 were prepared from the corre sponding ketones as previously reported 1 5.

In the present study vinyl ether alcohols and functional carboxylic acids were used to synthesize bifunctional vinyl ether esters using the immobilized enzyme candida antarctica lipase b as a catalyst. Vinyl acetate undergoes transesterification giving access to vinyl ethers. The alkene also undergoes diels alder and 2 2 cycloadditions. Table 1 shows the properties of polycarboxylic acids before and after blocking.

The other carboxylic acids and vinyl ethers were commercially avail able and they were used as received. 2 3 esteri cation of 3 hydroxy acids with vinyl ether the typical procedure is as follow s entry 11 in table 5. Protonated alcohol or ether pka 2 to 3 h2 35 3. Vinyl allylic aryl benzylic n h h o h o oh nh2 o sh ch3 o oh h2 n oh oh o h o oh2 above 50 7 2 to 3 2 to 3 4 5 9 10 10 10 16 18 18 20 25.

It undergoes transesterification with a variety of carboxylic acids. 1 2 4 trimellitic acid is rigid white crystal with high melting point and cannot be solved by organic solvent. Polycarboxylic acids were esterified with alkyl vinyl ethers to obtain blocked carboxylic acids having the hemiacetal esters moieties.