Method for accelerating oxime production

• US 5,334,762 A
• Filed: 02/04/1993
• Issued: 08/02/1994
• Est. Priority Date: 02/04/1993
• Status: Expired due to Fees

• Current Assignee: Cytec Technology Corp.
• Original Assignee: Zeneca Incorporated (Astrazeneca PLC)
• Inventors: Gosciniak, Donald J., Neilan, James P.
• Primary Examiner(s): O SULLIVAN, PETER G
• Application Number:
  US08/013,278
• Time in Patent Office: 544 Days
• Field of Search: 502/152, 556/87, 556/94, 556/95, 564/259
• US Class Current: 564/259
• CPC Class Codes: C07C 249/08 by reaction of hydroxylamines with carbonyl compounds

Abstract

A method for preparing oximes where an aldehyde or ketone is reacted with hydroxylamine or its salt in the presence of a catalytic amount of an organotin(IV) compound such as monoalkyltin(IV), dialkyltin(IV) and aryltin(IV). The organotin(IV) compound is represented by the formula I:

(R.sup.1).sub.n SnX.sub.m-n                                (I)

where R¹ is independently selected from alkyl of 1 to 18 carbons or aryl, X is halogen, oxygen, hydroxyl, OR¹, R² CO₂ --, R² O₂ C--(Z)_y --CO₂ -- or R² CO₂ (CH₂)_y S--, R² is alkyl of 1 to 18 carbons or aryl, Z is selected from CH₂ or CH═CH, where y is 0 to 6, n is 1 or 2 and m is 4 except that when X is oxygen, n is 2 and m is 3. Exemplary of the organotin(IV) compounds are butyltin tris(2-ethylhexanoate), dibutyltin diacetate and diphenyltin dichloride.

Claims

1. A method for preparing oximes, comprising:

reacting an aldehyde or ketone with hydroxylamine or a salt thereof in the presence of a catalytic amount of an organotin(IV) compound selected from the group consisting of monoalkyltin(IV), dialkyltin(IV) and aryltin(IV) compounds.

2. The method of claim 1 wherein the organotin(IV) compound is represented by the formula:

space="preserve" listing-type="equation">(R.sup.1).sub.n SnX.sub.m-n (I)

where R¹ is independently selected from alkyl of 1 to 18 carbons or aryl, X is halogen, oxygen, hydroxyl, OR¹, R² CO₂ --, R² O₂ C--(Z)_y --CO₂ --, or R² CO₂ (CH₂)_y S--, R² is alkyl of 1 to 18 carbons or aryl, Z is selected from CH₂ or CH═

CH, where y is 0 to 6, n is 1 or 2 and m is 4 except that when X is oxygen, n is 2 and m is 3.

3. The method of claim 1 wherein the organotin(IV) compound is selected from the group consisting of dibutyltin diacetate, dibutyltin dilaurate, dibutyltin di-2-ethylhexanoate, dibutyltin-S-S-bis(isooctylmercaptoethanoate), dibutyl tin oxide, dibutyltin dichloride, diphenylbutyltin tris-(2-ethylhexanoate), dibutyltin maleate, butyl tin tris(2-ethylhexanoate) and butyltin S,S'"'"'-tris(isooctylmercaptoethanoate).

4. The method of claim 1 wherein the aldehyde is a 2'"'"'-hydroxyarylaldehyde.

5. The method of claim 4 wherein the 2'"'"'-hydroxyarylaldehyde is salicylaldehyde or 5-nonylsalicylaldehyde.

6. The method of claim 1 wherein the aldehyde is benzaldehyde.

8. The method of claim 1 wherein the organotin(IV) compound is present in an amount of at least about 0.005%.

9. The method of claim 8 wherein the organotin(IV) compound is present in an amount of about 0.005% to about 0.2%.

7. The method of claim i wherein the ketone is acetophenone or 2'"'"'-hydroxyacetophenone.