Isobutene oxide, hydrolysis

Comparison of activation enthalpies for neutral hydrolysis of substituted oxi-ranes (propene oxide and butane oxides) [53] clearly demonstrates the preference of Beta pathways corresponding to the attack of water molecule on more substituted carbon atom (Fig. 10.13). Activation enthalpies lowering has been ascertained in the series ethene oxide>trans-2-butene oxide cis-2-butene oxide propene oxide > isobutene oxide. 

The competitiveness of the oxidation of isobutene compared to the conventional acetone cyanohydrin route (Equation 33) is not only related to its performance and better environmental standards but has to contend with the demands of other users for isobutene, particularly for MTBE and ETBE production. In fact the predominant methacrylic acid process is still the hydrolysis of acetone cyanohydrin however, the change of mood on the use of MTBE in gasoline blends in the USA, could signal a future shift of isobutene availability making it a more attractive feedstock for methacrylic acid production. 

Tribenzyl hydrazine is likely to be oxidized in air. In the presence of hydrazine, the C-O bonds of tert-butyl nitrate would be broken only to produce isobutene and hydrazine nitrate. Isopropyl nitrate is hydrolyzed in basic condition to produce 70-80 % isopropanol, 11-14 % propylene, and 8-14 % acetone. The hydrolysis process can be expressed as the following equation. 

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