903. Some derivatives of cis-1 : 2 : 3 : 6-tetrahydrophthalic anhydride

Gill, J. E.; Munro, J. D.

doi:10.1039/jr9520004630

Cited by 7 publications

(5 citation statements)

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“…The epoxyhexahydrophthalate esters (4, 70) can be prepared by epoxidation of the corresponding unsaturated tetrahydrophthalic acid esters with preformed peracetic acid or by in situ techniques (2, 3, 7, 9) employing hydrogen peroxide. The reaction can be represented schematically as:…”

Section: Methodsmentioning

confidence: 99%

Vinyl Epoxy Plasticizers -The Epoxyhexahydrophthalates"

Greenspan¹,

Gall²

1958

Ind. Eng. Chem.

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The alkyl epoxyhexahydrophthalates represent a new class of improved epoxy plasticizers with built-in stabilizing properties, protecting poly(viny1 chloride) resins against degradation caused by heat and light. They are primary plasticizers and show excellent compatibility at high concentration use levels with no evidence of bleed after prolonged exposure to light.As combination stabilizer-plasticizers they are applicable to a wide range of vinyl resin formulations and products-e. g., hose, toys, flooring, packaging, film, and foam THE epoxy plasticizers, widely used in vinyl resin processing, are epoxy fatty acid esters (5, 6, 72, 13)) prepared by epoxidation of unsaturated fatty acid esters of mono-and polyhydric alcohols. A new series, alkyl epoxyhexahydrophthalates, has been developed in these laboratories in a broad program of research on epoxy plasticizers. The epoxyhexahydrophthalates combine the excellent stabilizing properties of the epoxy fatty acid esters with the good over-all plasticizing properties of the phthalates. They are compatible with poly(viny1 chloride) at primary use levels and show no evidence of bleed, sometimes observed with specific epoxy fatty acid ester plasticizers at high use levels, after prolonged exposure to ultraviolet or diffused light. ExperimentalThe epoxyhexahydrophthalate esters (4, 70) can be prepared by epoxidation of the corresponding unsaturated tetrahydrophthalic acid esters with preformed peracetic acid or by in situ techniques (2,3, 7,9) employing hydrogen peroxide.The reaction can be represented schematically as:The tetrahydrophthalate esters were made by esterifying n-butyl, n-hexyl, isooctyl, and n-decyl alcohols (Enjay Co., Inc.) with tetrahydrophthalic anhydride (National Aniline Division) in the presence of an acid catalyst, water-washed, and vacuum-distilled.The in situ epoxidation process (8) is illustrated below for the preparation of di-2-ethylhexylepoxyhexahydrophthalate.One hundred grams of di-2-ethylhexyltetrahydrophthalate (Union Carbide Chemicals) and 20 grams of benzene were weighed into a three-necked flask equipped with a reflux condenser, thermometer, and a mechanical stirrer; 7.7 grams of glacial acetic acid and 1.

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Section: Methodsmentioning

confidence: 99%

Vinyl Epoxy Plasticizers -The Epoxyhexahydrophthalates"

Greenspan¹,

Gall²

1958

Ind. Eng. Chem.

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“…(122). esters were prepared by the addition of the elements of the corresponding hypohalous acid (12,59,65). The chlorohydrins of the 1 acid and the 4 anhydride were prepared by the opening of oxide rings with hydrogen chloride (59, 65).…”

Section: C==nc6hioch3-pmentioning

confidence: 99%

“…The epoxides of the 1 acid and of the 4 esters were synthesized by the reactions of the chlorohydrins with base (59,65). The epoxides of the 4 anhydride and of the 4 esters were prepared by the epoxidation of the double bond with peracetic acid Í59).…”

Section: C==nc6hioch3-pmentioning

confidence: 99%

“…The addition of bromine to the tetrahydrophthalic acids appears to have been a successful reaction in general (14,59,127) except that the dibromide of the 1 acid could not be isolated directly (14). It was prepared by hydrolysis of the dibromide of the dimethyl ester.…”

Section: B Addition Reactions Of the Carbon-carbon Double Bondmentioning

confidence: 99%

“…Small amounts of optically active impurities could have accounted for the results, however. On the basis of the expected configurations the reactions were as follows: The cis-4 anhydride has been treated (59) with peracetic acid under anhydrous conditions (54) to yield the corresponding epoxide. The action of water caused polymer formation.…”

Section: B Addition Reactions Of the Carbon-carbon Double Bondmentioning

confidence: 99%

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