Nitrosamine inhibition

• US 5,223,644 A
• Filed: 02/03/1992
• Issued: 06/29/1993
• Est. Priority Date: 02/02/1991
• Status: Expired due to Term

• Current Assignee: Huntsman International LLC (Huntsman Corporation)
• Original Assignee: Albright & Wilson Limited
• Inventors: Blezard, Michael, Jones, Glyn R.
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): O SULLIVAN, PETER G
• Application Number:
  US07/829,982
• Time in Patent Office: 512 Days
• Field of Search: 564/2, 564/4, 564/298, 564/301, 564/5, 564/6, 564/197, 544/173, 544/383, 546/347, 548/337, 560/155, 560/205, 560/250
• US Class Current: 564/2
• CPC Class Codes: C07C 291/04 containing amino-oxide bonds
• CPC Class Codes: C09K 15/02 containing inorganic compounds

Abstract

Bicarbonates and/or carbonates are used in greater than catalytic amounts to inhibit the formation of nitrosamines during the preparation, storage and/or use of amine oxides.

Claims

1. A method of stabilizing an amine oxide in order to inhibit the formation of nitrosamines therein during storage or heating of said amine oxide, said method consisting essentially of adding to said amine oxide before, during or after the preparation thereof from 2.5% to 20% by weight (based on the weight of amine reacted to form said amine oxide) of a stabiliser selected from the group consisting of bicarbonates, carbonates and mixtures of said bicarbonates and carbonates.

2. The method of claim 1, in which said amine oxide is produced by reacting a tertiary amine with hydrogen peroxide in the presence of from 2.5% to 20% by weight (based on the weight of said amine) of said stabiliser.

3. The method of claim 2, in which said tertiary amine has the general formula R¹ R² R³ N, wherein R¹, R² and R³, which may be the same or different, are each selected from the group consisting of straight chain alkyl groups, branched chain alkyl groups, straight chain alkenyl groups, branched chain alkenyl groups and aralkyl groups.

4. The method of claim 3, in which said tertiary amine has the general formula (R)_m (R¹)_n N, wherein m=1 or 2 and n=(3-m), the R groups, which may be the same or different, are each selected from the group consisting of alkyl, alkenyl, alkyl-polyalkyleneoxy and alkenyl-polyalkyleneoxy groups having from 8 to 24 carbon atoms;

esteralkyl, esteralkenyl, amidoalkyl, amidoalkenyl, alkyl-amidopropyl, and alkenyl-amidopropyl groups having from 7 to 23 carbon atoms, and the R¹ groups, which may be the same or different, are each selected from the group consisting of alkyl, alkoxy, hydroxyalkyl and polyalkyleneoxy groups having from 1 to 4 carbon atoms.

5. The method of claim 2, in which said tertiary amine is a cyclic amine.

6. The method of claim 5, in which said tertiary amine is one selected from the group consisting of imidazolines, pyridines, N-substituted morpholines, and N-substituted piperazines.

7. The method of claim 2, 3, 4, or 5, in which the molar ratio of said amine to said hydrogen peroxide is from 1:

0.9 to 1;

1.1.

8. The method of claim 7, in which said molar ratio of amine to hydrogen peroxide is about 1:

1.

9. The method of claim 1, in which said stabiliser consists essentially of a bicarbonate selected from the group consisting of alkali-metal bicarbonates, alkaline-earth metal bicarbonates and ammonium bicarbonate.

10. The method of claim 9 in which said stabiliser consists essentially of a bicarbonate selected from the group consisting of sodium bicarbonate, potassium bicarbonate, magnesium bicarbonate and calcium bicarbonate.

11. The method of claim 1, in which the proportion of said stabiliser is from 6 to 10% by weight based on total weight of said amine.

12. The method of claim 1, in which said stabiliser also includes a carbonate selected from the group consisting of alkali metal carbonates, alkaline earth metal carbonates and ammonium carbonate.

13. The method of claim 12, in which said carbonate is one selected from the group consisting of sodium carbonate and potassium carbonate, added to said amine oxide after the preparation thereof.

14. The method of claim 12, in which said stabiliser consists essentially of sodium bicarbonate and sodium carbonate in a molar ratio of about 1:

1.

15. The method of claim 1, said method being carried out at a temperature of from 2°

C. to 85°

C.

16. The method of claim 15, in which said temperature is from 30°

C. to 50°

C.

17. The method of claim 15 or 16, in which said temperature is about 40°

C.