Ch_322b_16.02 - Chapter 16.2 lecture note

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Syntheses of Aldehydes Industrial Syntheses from Petroleum Formaldehyde is the most important industrial aldehyde. Annual production in the United States is close to 8 billion pounds per year. It is produced by way of methanol (another important industrial chemical) by the scheme below. Petroleum and natural gas CH 4 [O] CO H 2 CH 3 OH methanol over 11 billion pounds produced annually in US O 2 catalytic Ag 600-650 o C HCH O = formaldehyde over 8 billion pounds per year of formalin solution (37% by weight) are produced annually in the US Much of the formaldehyde is used to produce a class of polymers called phenol-formaldehyde resins. A resin is a polymer with a three-dimensional network of repeating units. The first commercially successful synthetic polymer was Bakelite, a phenol-formaldehyde resin developed by Leo Baekeland in 1909.
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Laboratory or General Synthetic Methods Because aldehydes are between primary alcohols and carboxylic acids in an oxidation-reduction sequence, they are synthesized by both selective oxidation of primary alcohols and selective reduction of carboxylic acid derivatives. RCH 2 OH RCH O = RCOOH [O] [H] [O] [H] or RCOX Oxidation Oxidation of primary and secondary alcohols under vigorous conditions yields carboxylic acids and ketones , respectively RCH 2 OH [O] RCH O = [O] RCOOH RCHR' OH [O] RCR' O =
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