Processes for making unsaturated aliphatic hydrocarbons, including vinyl acetate from ethylene glycol diacetate

A process for converting substituted, saturated aliphatic hydrocarbon to unsaturated aliphatic hydrocarbon-containing chemical, said substituted, saturated aliphatic hydrocarbon-containing compound being represented by the structure

• wherein R1 and R2 are the same or different and are selected from the group consisting of hydrogen and alkyl of one to six carbon atoms;
• Y1, Y2, Y3 and Y4 are the same or different and selected from the group consisting of hydrogen and an electron-withdrawing moiety selected from the group consisting of hydroxyl;
• halogen;
• substituted and unsubstituted alkoxy of 1 to 4 carbons;
• substituted and unsubstituted acyl of 1 to 4 carbons;
• unsubstituted and substituted aryl of 6 to 20 carbons;
• sulfuryl;
• sulfonyl of 1 to 4 carbons;
• nitro of 0 to 4 carbons;
• and phosphoryl, and preferably, at least one of Y1 and Y2 and at least one of Y3 and Y4 is an electron withdrawing moiety, comprising:
• passing the feedstock to a cavitation apparatus, said feedstock comprising the substituted, saturated aliphatic hydrocarbon-containing chemical;
• passing the feedstock through a cavitation apparatus to provide cavitation features and provide a two-phase liquid-gas mixture containing at least a major portion of the substituted, saturated aliphatic hydrocarbon-containing chemical in the liquid state and vapor phase bubbles then collapsing the bubbles resulting in localized areas of increased pressure and temperature sufficient to convert at least a portion of the saturated aliphatic hydrocarbon-containing chemical to unsaturated aliphatic hydrocarbon and provide a product mixture;
• and
• separating unsaturated aliphatic hydrocarbon from the product mixture.

A process for converting ethylene glycol diacetate to vinyl acetate comprising:

• admixing an ethylene glycol diacetate-containing feedstock with a substantially non-reactive compound having a normal boiling point less than that of ethylene glycol diacetate to provide a liquid-liquid mixture;
• passing the liquid-liquid mixture through a hydrodynamic cavitation apparatus to provide cavitation features to provide a two-phase liquid-gas mixture containing the ethylene glycol diacetate in the liquid state and the non-reactive compound in the gaseous state in the form of vapor phase bubbles by reducing the pressure to at or below the liquid/vapor pressure threshold for the non-reactive compound then collapsing the bubbles resulting in localized areas of increased pressure and temperature sufficient to convert at least a portion of the ethylene glycol diacetate to vinyl acetate and acetic acid and provide a product mixture;
• and
• separating vinyl acetate from the product mixture.