Diphenolic acid

Diphenic acid, bl41 Diphenolic acid, b205 Diphenyl, bl38 Diphenylacetone, d767 Diphenylbenzenes, t7 thru t9 sym-Diphenylcarbazide, d746 Diphenyldiazene, a312... 

Levulinic acid Glucose, fructose, xylose 1,4-Pentanediol, 5-methyl-2-pyrrolidone, acrylic acid, diphenolic acid, methyl tetrahydofuran (MTHF), levulinate ester, succinic acid, jS-acetyl-acrylic acid, y-valero-lactone Bozell etal., 2000 Keenan etal., 2004 Werpy and Petersen, 2004 Chang etal., 2007... 

Synthesis. Five different polyaryl ethers were made from the condensation product, resulting from the reaction of phenol and levulinic acid, commonly referred to as diphenolic acid, and one or more of the following monomers bisphenol A, dichlorodiphenyl sulfone, 2,6-dichloro-benzonitrile, and 4,4 -difluorobenzophenone. The resulting polymers were subsequently methylated such that the common monomer becomes (1) ... 

Because the procedure used in making these polymers is similar (10), it is sufficient to describe one, namely, the synthesis of the ter-polyether from bisphenol A, diphenolic acid, and dichlorodiphenyl sulfone, whose polymerization scheme is ... 

NMR Characterization. The structures of the polyarylethers A-K (Table I) were confirmed through their NMR spectra. As an example of the NMR data, observe the spectrum in Figure 1 for sample K, the condensation product of disodium salt of diphenolic acid and 2,6-di-chlorobezonitrile which was subsequently methylated as discussed above. 

Diphenolic acid, the condensation product of levulinic acid and phenol, is useful in the preparation of modified phenol-formaldehyde resins, polyether resins, or as monocarboxylic acid chain stoppers in alkyd resins (152). It can be substituted for bisphenol-A, the primary raw material in the production of epoxy resins (153). 

One day a salesman from Quaker Oats stopped by and said levulinic acid would soon be available very inexpensively from Quaker Oats. The moment I heard that, I made the bisphenol by reacting levulinic acid with phenol to make what is now called diphenolic acid. A few weeks later, I sent a note off to JACS. Soon Johnson Wax wanted to buy the patent for which we d applied. Our director of research asked me, What should we charge for this I said It was two days work if we got ten thousand dollars, we would be well paid, but they must want it very badly, so ask for a million Well, he got it. Then, of course, lawyers descended on my lab to make sure everything I worked on was really patented, but I had already seen to that. 

Levulinic acid can be converted by known processes to the solvents, tetrahydrofuran and 2-methylfuran, to succinic acid, to 5-aminolevulinic acid for weed control (see Chap. 11) and to diphenolic acid. Diphenolic acid may be useful in waterborne epoxy coatings and other resins. If a suitable acid catalyst that can be left in the resin can be found, it may be possible to convert diphenolic acid, by self-acylation, to an analogue of phenol-formaldehyde resins, thus eliminating the use of the carcinogenic... 

Scheme 30 Preparation of diphenolic acid, succinic acid, and 5-bromolevulinic acid from LA...

Diphenolic acid (DPA) 88, a condensation product of LA and two molecules of phenol, is considered to be a renewable analogue of bisphenol A (BPA), a high-volume chemical used to make polycarbonate plastics. BPA is known to have estrogenic activity [222], which has led to its withdrawal from some markets. Thus, DPA has the potential to displace BPA across the range of its polymer applications [223]. 

Fig. 4 Some possible reactions of protein-bound lysine with o-diphenolic acids.

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