Phthalate derivatives

The principal solvolysis reactions for PET are methanolysis with dimethyl terephthalate and ethylene glycol as products, glycolysis with a mixture of polyols and BHET as products, and hydrolysis to form terephthalic acid and ethylene glycol. The preferred route is methanolysis because the DMT is easily purified by distillation for subsequent repolymerization. However, because PET bottles are copolyesters, the products of the methanolysis of postconsumer PET are often a mixture of glycols, alcohols, and phthalate derivatives. The separation and purification of the various products make methanolysis a cosdy process. In addition to the major product DMT, methanol, ethylene glycol, diethylene glycol, and 1,4-cyclohexane dimethanol have to be recovered to make the process economical.1... 

As with pyridazines, phthalazines, the other benzopyridazines, were also prepared most frequently through the condensation of hydrazines with carbonyl-containing compounds, typically phthalate derivatives. Recently, Napoletano and co-workers demonstrated the condensation of hydroxylactone 189 and hydrazine to afford phthalazones 190. After POCI3 chlorination, advanced intermediates for a novel series of PDE4 inhibitor I, phthalazines 191 were prepared <00BMC2235>. 

It is not known with certainty whether any of DEHP phase I metabolites are less toxic than the others, so shifting the metabolism toward phthalic acid or a particular oxidized phthalate derivative might not change the toxicity. 

Optically pure (+)-l-octyn-3-ol may be obtained by recrystallization of the half acid phthalate with (+)-a-methylbenzyl amine (Aldrich Chemical Company). The half acid phthalate salt Is made by heating equal molar amounts of l-ocytn-3-ol and phthalic anhydride. This half acid phthalate derivative... 

Is a waxy solid which does not lend itself to recrystallization. Attempts to form crystalline salts of the phthalate derivative with achiral alkyl amines only lead to waxy solids or thick oils. The phthalic amine salt made with racemic l-octyn-3-ol requires 3-4 recrystal 1 Izations from methylene chloride to resolve enantiomers. The first recrystallization may take several days, with successive recrystal 1Izations becoming easier. If the 86% ee l-octyn-3-ol is used to make the phthalic amine salt only one facile recrystalHzation is needed to provide optically-pure alcohol. The pure amine salt melts at 132-134°C. The enantiomeric purity of the salt may be determined by NMR by observing the ethynyl hydrogen doublets at 6 2.48 (minor) and 2.52 (major) (CDClj solvent). 

Tritylsodium has been used in the preparation of acid phthalate derivatives of tertiary alcohols by the following procedure. " An ethereal solution of tritylsodium... 

Cyclohexanol is used for the production of adipic acid and caprolactam for making nylon. Its phthalate derivatives are used for plasticizers. It is used as a stabilizer for soaps and detergents as a solvent for lacquers, varnishes, and shellacs and as a dye solvent for textiles. 

Bu, T., Liu, M., Zheng, L., Guo, Y., and Lin,X. (2010). a-Glucosidase inhibition and the in vivo hypoglycemic effect of butyl-isobutyl-phthalate derived from the Laminaria japonica rhizoid. Phytother. Res. 24,1588-1591. 

Figure 9.20 HPLC separation of phthalate derivatives of polypropylene glycol. oligomers separated in Figure 9.5 [37]. By permission of Dr Alfred Hiithig Verlag GmbH.

Though MOM deprivation product 2.2.21 was accidentally obtained, it was still useful to test two key reactions for total synthesis Wessely oxidative dearomatization reaction and intramolecular Diels-Alder reaction (Fig. 2.20). A pair of diethyl phthalate derivative 2.2.22 with the ratio of 2 1 and 95 % yield could be obtained from phenol 2.2.21 in acetic acid solvent with the presence of lead tetraacetate at room temperature after 5 min. Then, we tried intennolecular Diels-Alder reaction. Unfoitunately, both substrate 2.2.22 and dimethyl acetylene dicarboxylate were not producing Diels-Alder product 2.2.23 under toluene refluxing or sealing mbe heating conditions, only gave the results of raw material recovery. 

Ideally a plasticiser should maintain the flexibility of a polymer over as wide a temperature range as possible. In practice, a certain proportion of low temperature plasticisers such as sebacates or adipates is often added to the phthalate or other primary plasticiser to give optimum low temperature properties, although certain phthalates derived from straight chain alcohols are appreciably better than DOP (di-octyl phthalate) or DiOP (di-iso-octyl phthalate) in this respect. 

Deoxychoiatic acid Deoxychoiic acid 5P-Deoxycholic acid 7-Deoxycholic acid. See Desoxycholic acid 4-Deoxytetronic acid. See Butyrolactone DEP. See Diethyl phthalate Derivative of N-all l tallow propylene diamine CAS 68803-75-8... 

Li, Y, Qian, Z.-J., and Kim, S.-K. (2008) Cathepsin B inhibitory activities of three new phthalate derivatives isolated from seahorse, Hippocampus kudu Bleeker. Bioorg. Med. Chem. Lett., 18, 6130-6134. 

---