Preparation and polymerization of vinyl esters of cyclic and polychloro fatty acids

Marvel, C. S.; Hill, Jorik; Cowan, J. C.; Friedrich, J. P.; O’Donnell, J

doi:10.1002/pol.1964.100020604

Cited by 6 publications

(3 citation statements)

References 10 publications

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“…These processes include heat treatment (with and without a hydrogenation catalyst), alkaline isomerization and catalytic hydrogenation. For the most part, researeh on CFA has fallen into four categories: studies of conditions which favor their formation (1,5,16,24), methods of purification (10,17), evaluation of their toxicity (6)(7)(8), and synthesis and evaluation of selected derivatives (2,9,14,15,22). Very little has been done to elucidate their structures specifically.…”

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C₁₈‐saturated cyclic acids from linseed oil: A structural study

Friedrich

1967

J Americ Oil Chem Soc

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The preparation of C18‐saturated cyclic acids from linseed oil by heat treatment in the presence of alkali, followed by hydrogenation and subsequent isolation of the cyclic fraction, gives rise to a series of at least 11 isomers as evidenced by GLC. Eight of these isomers have now been shown to be geometric pairs of positional isomers with the following general formula: {fx244–1} An unequivocal synthesis of isomers (x=0,1,2 and 3) indicates that the principal positional isomer (ca. 55%) of HCal is 9‐(2艂‐n‐propylcyclohexyl)‐nonanoic acid. This isomer undoubtedly results from the cyclization of 10,12,14‐octadecatrienoic acid present in the isomerized mixture. The predominance of this isomer is further substantiated by mass spectral analysis. The four positional isomers prepared constitute about 80% of the mixture as determined by gas‐liquid chromatography. The four synthetic aromatic positional isomers show single peaks whereas their hydrogenated counterparts show two peaks. Thus each of the positional isomers of saturated cyclic acids is composed of two geometric isomers.

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C₁₈‐saturated cyclic acids from linseed oil: A structural study

Friedrich

1967

J Americ Oil Chem Soc

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“…Vegetable oils (11) (Continued on next page) isomeric vinyl esters (II and III) can be prepared selectively (6. 75).…”

Section: Ch3(ch2)5co(ch2)ocooch=ch2mentioning

confidence: 99%

World-Wide Research, Polymerization Studies with Vinyl Esters of Acids Derived from Agricultural Products

Marvel¹,

Griffith²

1965

J. Agric. Food Chem.

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This paper is a review describing the results of previously reported experimental work on vinyl esters derived from agricultural products. In particular, the reactivity ratios of a wide variety of vinyl esters with other vinyl monomers are reviewed. Also, the properties of a variety of vinyl ester-vinyl chloride copolymers are surveyed.For the past eight years a research group has been working on the preparation of polymers from monomers obtained from various agricultural products. The work, initiated at the University of Illinois and continued at the University of Arizona, has dealt with a wide variety of monomers derived from cereal grains, oil seeds, animal fats, sugar cane, and naval stores. For this review, the topic is the polymerization of vinyl esters which have been synthesized from these various source materials. Reactivity RatiosOne of the first projects undertaken was a study of the reactivity ratios of the vinyl esters of a wide variety of acids with various other polymerizable monomers (ff) to learn something about the composition of the products which might be readily prepared and what charging ratios would lead to the most homogeneous products. Previous work had given values for vinyl acetate, vinyl formate, vinyl palmitate, vinyl stearate, and vinyl trifluoroacetate with such monomers as vinyl chloride, vinylidene chloride, acrylonitrile, styrene, methyl acrylate, and vinyl acetate.

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“…functionalities along the carbon chain have been synthesized from fatty acids of vegetable oil origin for copolymerization with vinyl chloride to evaluate their effectiveness as internal plasticizers (8)(9)(10)12). Preparation of vinyl esters from hydroxy fatty acids by reaction with acetylene is complicated by side reactions and leads to poor yields of the desired product.…”

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Synthesis of vinyl threo‐9, 10‐threo‐12, 13‐tetrahydroxystearates

O舗Donnell

Gast

Cowan

et al. 1967

J Americ Oil Chem Soc

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Methyl esters from vernonia oil containing cis-12,13-epoxy-cis-9-octadeeenoate were reacted with acetone in the presence of a boron trifluoride catalyst to yield trans-12,13-O-isopropylidene-9ene derivative I. Epoxidation of the unsaturation followed by reaction with acetone gave the isomeric trans,trans-di-O-isopropylidene derivatives III of 9,10:12,13-tetrahydroxystearates. The carboxylie acids of III were converted to vinyl esters and subsequent hydrolysis of the isopropylidene groups with boric acid produced vinyl threo-9,10-threo-12,13-tetrahydroxystearates. By the same sequence of reactions monoepoxidized methyl linoleate yielded an optically inactive derivative which had identical refractive index, Ig spectrum, and GLC data to III from vernonia methyl esters.

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Preparation and polymerization of vinyl esters of cyclic and polychloro fatty acids

Cited by 6 publications

References 10 publications

C₁₈‐saturated cyclic acids from linseed oil: A structural study

C₁₈‐saturated cyclic acids from linseed oil: A structural study

World-Wide Research, Polymerization Studies with Vinyl Esters of Acids Derived from Agricultural Products

Synthesis of vinyl threo‐9, 10‐threo‐12, 13‐tetrahydroxystearates

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Preparation and polymerization of vinyl esters of cyclic and polychloro fatty acids

Cited by 6 publications

References 10 publications

C18‐saturated cyclic acids from linseed oil: A structural study

C18‐saturated cyclic acids from linseed oil: A structural study

World-Wide Research, Polymerization Studies with Vinyl Esters of Acids Derived from Agricultural Products

Synthesis of vinyl threo‐9, 10‐threo‐12, 13‐tetrahydroxystearates

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C₁₈‐saturated cyclic acids from linseed oil: A structural study

C₁₈‐saturated cyclic acids from linseed oil: A structural study