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Process for making carboxylic acids
| Details |
Inventors: Rebrovic, Louis;
Assignee: Henkel Corporation (Plymouth Meeting, PA)
Primary Examiner: Dees; Jose G.
Assistant Examiner: Frazier; Barbara S.
Attorney, Agent or Firm: Szoke; Ernest G., Jaeschke; Wayne C., Drach; John E.
A carboxylic acid is made by contacting an organic compound having at least one olefinic bond with ozone to form a mixture of ozonization products; contacting the mixture of ozonization products with oxygen to form a mixture of oxidation products; contacting the mixture of oxidation products with oxygen in the presence of an effective amount of a catalyst selected from the group consisting of a manganese-exchanged X-zeolite, a manganese-exchanged Y-zeolite, a manganese-exchanged A-zeolite, or a combination thereof to form said carboxylic acid. |
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DETAILED DESCRIPTION OF THE INVENTION Other than in the claims and in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients or reaction conditions used herein are to be understood as modified in all instances by the term "about".
The first step in the process according to the invention involves the reaction of an organic compound having at least one olefinic bond with ozone.
The compound having at least one olefinic bond can be linear or cyclic.
If the compound having at least one double bond is a linear alkene, then 2 carboxylic acids will be formed which may or may not be different depending upon the position of the double bond.
For example, if 3-hexene is used, then 2 moles of propionic acid would be formed per mole of 3-hexene.
If 2-hexene is used, then 1 mole of acetic acid and 1 mole of butyric acid will be formed per mole of 2-hexene.
If the compound having at least one double bond also contains a functional group, then the resulting carboxylic acid may also contain the same functional group as long as the functional group is not susceptible to reaction with ozone or other substances in the process such as oxygen.
If the compound having at least one olefinic bond also contains a carboxylic acid functionality, then the resulting product may contain 1 mole of a dicarboxylic acid and 1 mole of a mono-carboxylic acid per mole of starting olefin depending upon the structure of the starting compound.
For example, if oleic acid is the compound having at least one olefinic bond, the product of the process according to the invention will produce one mole of pelargonic acid and one mole of azelaic acid per mole of oleic acid.
The process according to the invention is particularly useful in making pelargonic and azelaic acids from oleic acid, especially technical grade oleic acid which is comprised of, in addition to a major amount of oleic acid, a C.
sub.
12 saturated carboxylic acid; a C.
sub.
14 saturated carboxylic acid; a C.
sub.
14 monounsaturated carboxylic acid; a C
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Molecular Biology 
