Process for production of alkenediols
AssigneeStandard Oil Company (Indiana)
InventorGeorge R. Wood
Life of this patent
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Abstract
Alkenediols are produced by hydrolysis of a dibromoalkenes in the presence of alkali metal formate. In a preferred embodiment, alkenediols, and particularly 2-butene-1,4-diol, are produced in a series of steps comprising bromination of conjugated diene with cupric bromide, hydrolysis of the resulting dibromobutenes to alkenediols in the presence of alkali metal formate, and regeneration of cupric bromide and alkali metal formate such that only conjugated diene, oxygen and water are consumed.
Claims21
A process for production of alkenediol comprising (A) contacting conjugated diene of 4 to about 12 carbon atoms with cupric bromide under bromination conditions;
- (B) contacting a product from (A) comprising dibromoalkene containing 4 to about 12 carbon atoms corresponding to the formula R.sub.2 BrCCR:CRCBrR.sub.2 or R.sub.2 C:CRCBrRCBrR.sub.2 wherein each R is independently hydrogen or an alkyl radical of 1 to about 8 carbon atoms consistent with the conjugated diene employed in (A), or a mixture of dibromoalkenes of said formulae wherein the R groups are identical, with alkali metal formate under hydrolysis conditions;
- (C) separating alkenediol from the product of (B);
- and (D) contacting cuprous bromide, alkali metal bromide and formic acid by-products from steps (A) and (B) with molecular oxygen under conditions effective to regenerate cupric bromide and alkali metal formate.
A process for production of alkenediol comprising:
- (A) contacting conjugated diene of 4 to about 12 carbon atoms with cupric bromide under bromination conditions in an inert liquid medium;
- (B) contacting the product from (A) with alkali metal formate under hydrolysis conditions;
- (C) separating alkenediol from the product of (B);
- and
- (D) contacting solid cuprous bromide, alkali metal bromide and formic acid remaining after separation in (C) with molecular oxygen under conditions effective to regenerate cupric bromide and alkali metal formate.
A process for production of 2-butene-1,4-diol comprising the steps:
- (A) contacting 1,3-butadiene and cupric bromide in the presence of alkali metal formate and an inert liquid solvent for 1,3-butadiene under bromination conditions to form a reaction mixture comprising dibromobutenes, cuprous bromide and alkali metal formate;
- (B) substantially separating inert hydrocarbon solvent from the reaction mixture of (A);
- (C) combining the product remaining after separation in (B) with a solution of formic acid in water under hydrolysis conditions to form a reaction mixture comprising water, formic acid, 2-butene-1,4-diol, alkali metal formate, alkali metal bromide and cuprous bromide;
- (D) separating formic acid, water and a major portion of 2-butene-1,4-diol from the reaction mixture of (C) to form a concentrated slurry comprising alkali metal formate, alkali metal bromide, cuprous bromide and 2-butene-1,4-diol;
- (E) separating 2-butene-1,4-diol from the formic acid and water of (D);
- (F) contacting alkali metal formate, alkali metal bromide and cuprous bromide from (D) with molecular oxygen in the presence of formic acid and water under conditions effective to regenerate cupric bromide and alkali metal formate;
- (G) recycling cupric bromide and alkali metal formate from (F) to (A).
Dependencies are inferred from the claim text.