Process for producing long chain amino acids and dibasic acids
AssigneeVitaworks IP, LLC
InventorsSongzhou Hu, Zhen Song
Life of this patent
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Abstract
There is disclosed a process for the production of dodecanedioic acid and 11-aminoundecanoic acid, comprising: (1) reacting castor oil with a primary or secondary amine to form a amide; (2) isomerizing the amide in the presence of a catalyst to form ketoamide; (3) reacting the ketoamide with hydroxylamine to form the oximeamide; (4) subjecting the oximeamide to Beckmann rearrangement to yield a mixture of two diamides; and (5) hydrolyzing the mixed diamides to produce dodecanedioic acid, 11-aminoundecanoic acid, hexylamine and heptanoic acid.
Claims10
A process for producing dodecanedioic acid and 11-aminoundecanoic acid, comprising:
- (a) reacting castor oil with a primary or secondary amine HNR1R2 to form an amide of the formula (Ib):
- in the absence or in the presence of at least one solvent, wherein R1 and R2 are each independently hydrogen, or C1 to C12 aliphatic or aromatic groups;
- (b) isomerizing (Ib) in the presence of at least one catalyst to form a ketoamide of the formula (IIa):
- (c) subjecting the ketoamide (IIa) to an oximation reaction with hydroxylamine or an ammoximation reaction with ammonia and hydrogen peroxide in the presence of an ammoximation catalyst to form an oximeamide of the formula (IIIc):
- (d) subjecting the oximeamide (IIIc) to Beckmann rearrangement to yield a mixture of diamides of the formula (IVe) and (IVf):
- (e) hydrolyzing the mixed diamides (IVe) and (IVf) with an acid or a base to dodecanedioic acid (Va), 11-aminoundecanoic acid (VIa), hexylamine (VIIa), and heptanoic acid (VIIIa) of the structures:
- and
- (f) separating dodecanedioic acid (Va), 11-aminoundecanoic acid (VIa), hexylamine (VIIa), and heptanoic acid (VIIIa).
- (g)
A process for producing dodecanedioic acid and 11-aminoundecanoic acid, comprising:
- (a) reacting castor oil with a primary or secondary amine HNR1R2 to form an amide of the formula (Ib):
- in the absence or in the presence of at least one solvent, wherein R1 and R2 are each independently hydrogen, or C1 to C12 aliphatic or aromatic groups;
- (b) hydrogenating (Ib) to form 12-hydroxystearic acid amide of the formula (Id):
- (c) oxidizing (Id) to form a ketoamide of the formula (IIa):
- (d) subjecting the ketoamide (IIa) to an oximation reaction with hydroxylamine or an ammoximation reaction with ammonia and hydrogen peroxide in the presence of an ammoximation catalyst to form an oximeamide of the formula (IIIc):
- (e) subjecting the oximeamide (IIIc) to Beckmann rearrangement to yield a mixture of diamides of the formulas (IVe) and (IVf):
- (f) hydrolyzing the mixed diamides (IVe) and (IVf) with an acid or a base to dodecanedioic acid (Va), 11-aminoundecanoic acid (VIa), hexylamine (VIIa), and heptanoic acid (VIIIa) of the structures:
- and
- (g) separating dodecanedioic acid (Va), 11-aminoundecanoic acid (VIa), hexylamine (VIIa), and heptanoic acid (VIIIa).
A process for producing dodecanedioic acid and 11-aminoundecanoic acid, comprising:
- (a) hydrogenating castor oil to form hydrogenated castor oil of the formula (Ic):
- (b) reacting hydrogenated castor oil (Ic) with a primary or secondary amine HNR1R2 to form a hydroxyamide of the formula (Id):
- in the absence or in the presence of at least one solvent, wherein R1 and R2 are each independently hydrogen, or C1 to C12 aliphatic or aromatic groups;
- (c) oxidizing (Id) to form a ketoamide of the formula (IIa):
- (d) subjecting the ketoamide (IIa) to an oximation reaction with hydroxylamine or an ammoximation reaction with ammonia and hydrogen peroxide in the presence of an ammoximation catalyst to form an oximeamide of the formula (IIIc):
- (e) subjecting the oximeamide (IIIc) to Beckmann rearrangement to yield a mixture of diamides of the formulas (IVe) and (IVf):
- (f) hydrolyzing the mixed diamides (IVe) and (IVf) with an acid or a base to dodecanedioic acid (Va), 11-aminoundecanoic acid (VIa), hexylamine (VIIa), and heptanoic acid (VIIIa) of the structures:
- and
- (g) separating dodecanedioic acid (Va), 11-aminoundecanoic acid (VIa), hexylamine (VIIa), and heptanoic acid (VIIIa).
Dependencies are inferred from the claim text.