The structures of maleic anhydride adducts of essentially pure oleic, linoleic and linolenic methyl esters have been determined. The cleavage of the methyl oleate adduct yields a product with a succinyl structure, with or without shift of the double bond; four isomeric structures are possible. The first adduct of maleic anhydride with methyl linoleate is a succinyl derivative followed by a shift into the conjugated isomer with whi& the second maleic anhydride reacts via a 1-4 Diels Alder addition to yield a second adduct having a cyclohexene structure. The first two moles of maleic anhydride add to methyl linolenate to form di-succinyl derivatives followed by a shift into conjugated diene and triene. The third maleic anhydride adds via a 1-4 addition to yield a disuccinyl and one 1-4 adduct. A number of isomers are possible for the linoleate and linolenate adduct. Uber die Reaktion des Maleinsaureanhydrids mit isolierten cisungesattigten FettsaureesternDie Strukturen der Maleinsaureanhydrid-Addukte von reinem U1-, Linol-und Linolensaure-methylester wurden ermittelt. Die Spaltung des Methyloleat-Addukts ergab ein Produkt mit einer Bernsteinsaure-Struktur mit oder ohne Veranderung der Lage der Doppelbindung, wobei vier isomere Strukturen moglich sind. Bei der Reaktion von Maleinsaureenhydrld mit Methyllinolet entsteht zunadxt ein Bernsteinsaure-Derivat, das in das konjugierte Isomere iibergeht. Letzteres reagiert weiter mit Maleinsaureanhydrid gemiiD einer Diels-Alder-Addition unter Bildung eines zweiten Addukts rnit einer Cyclohexen-Struktur. Aus Methyllinolenat entstehen zunachst durch die Reaktion mit zwei Molekiilen des Maleinsaureanhydrids die Dibernsteinsaure-Derivate, die in konjugierte Diene und Triene iibergehen. Durch Anlagerung eines weiteren Maleinsaureanhydrid-Molekiils ge-maD einer 1,4-Addition entstehen ein Uibernsteinsaure-Derivat sowie ein 1,4-Addukt. Linolat-und Linolenat-Addukte ergeben moglid~erweise mehrere Isomere. Angew. Chem. 62, 475 [1950].

Sodium hydroxide catalyzed glycerolysis of linseed oil is greatly enhanced by increase in temperature but only moderately by increase in catalyst concentration. That the active catalyst under these conditions is the glyceroxide ion and not the hydroxide ion was confirmed by performing the reaction with freshly prepared sodium glyceroxide. In all cases alcohol solubility is reached before the reaction attains equilibrium. Component glycerides analysis at these points shows that the monoglycerides content at alcohol solubility is about 35% and at equilibrium about 45%. Further, there are about twice as many 1,3‐diglycerides as either 1,2‐diglycerides or triglycerides. Component fatty acid analysis of these individual glycerides shows that all the fatty acids of the parent oil are present in every one of these glyceride types and in about the same proportions. Monoglycerides in the early stages of reaction are richer in saturated fatty acids indicating that the catalyst attacks the primary alcoholic ester portion of glycerides first. Similarities in the fatty acid compositions of 1‐and 2‐monoglycerides at these early stages indicate that the latter are formed by acyl migration from the former. Based on these observations a mechanism for glycerolysis has been proposed.

Lead tetraacetate in the presence of catalytic amounts of Cu(II) has been shown to be very effective for the conversion oi carboxylic acids to terminal olefins with one less carbon atom. The advantage of this method is that a reaction temperature of only 8OOC is needed and it yields very few side products. This low reaction temperature makes it ideal for the decarboxylation of drying oil derived fatty acids which contain very reactive internal unsaturation. This paper describes the use of lead tetraacetate to produce 17 carbon terminal polyolefins from unsaturated fatty acids with pyridine and lithium acetate as catalyst. The products of these reactions were analyzed by IR for disappearance of the carbonyl peak and appearance of peaks due to terminal unsaturation. IR spectra gave very little evidence of isomerization of the cis internal double bonds to the trans isomers. O l e 5 e aur Fattiouren von trodmenden Ulen d u d oxidative DecarboxyUerung auf katalytischem WegeBleitetraacetat ist in Gegenwart katalytismer Mengen von Cu(1I)-Salzen sehr wirksam bei der Umwandlung von Carbonsauren in endstandige Olefine mit einer um 1 C-Atom geringerm Kohlenstoffkette. Diese Methode hat den Vorteil. daD die Reaktionstemperatur niedrig ist (800 C) und nur wenige Nebenprodukte gebildet werden. Wegen der niedrigen Reaktionstemperatur ist die Methode hervorragend geeignet zur Decarboxylierung von Fettsauren der trodmenden ale, die sehr reaktive Doppelbindungen enthalten. Die vorliegende Arbeit behandelt die Herstellung von endstandigen Olefinen mit 17 C-Atomen aus ungesattigten Fettsauren unter Vexwendung von Bleitetraacetat und Pyridin mit Lithiumacetat als Katalysatur. Mit Hilfe der IR-Spektroskopie wurden die Reaktionsprodukte auf das Verschwinden der Carbonylbande und das Auftreten der fur endstiindige olefinische Doppelbindungen charakteristischen Peaks untersuht. Die IR-Spektren deuten darauf hin, daO sich die innenstandigen cis-Doppelbindungen nur in geringem AusmaD zu den trans-Doppelbindungen umlagen.

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Conclusions It seems quite apparent that the use of drying oils in classical varnishes is giving way to the use of oils in similarly functioning coatings or drying oil‐free coatings. The chemistry of drying oils in the varnish‐cooking process is not too clearly established but appears to be one of ester interchange between oil and resin. More research in this area is indicated. However if future research is to be undertaken, it must be justified. In view of the declining varnish market, this is doubtful. Lack of data makes it impossible accurately to correlate oil and resin functionality into a usable mathematical relationship.