Hydrogen sulfide suppression with amine derivative

• US 4,778,609 A
• Filed: 11/18/1987
• Issued: 10/18/1988
• Est. Priority Date: 04/25/1985
• Status: Expired due to Fees

• Current Assignee: The Lubrizol Corporation (Berkshire Hathaway Incorporated)
• Original Assignee: The Lubrizol Corporation (Berkshire Hathaway Incorporated)
• Inventors: Koch, Frederick W., Floyd, Robert L.
• Primary Examiner(s): Howard, Jacqueline V.
• Application Number:
  US07/121,984
• Time in Patent Office: 335 Days
• Field of Search: 252/32.7 E, 252/47.5, 252/50, 252/47, 252/32.5
• US Class Current: 508/331
• CPC Class Codes: C07G 99/002 Compounds of unknown constitution containing sulfur
• CPC Class Codes: C10M 135/02 Sulfurised compounds
• CPC Class Codes: C10M 135/04 Hydrocarbons
• CPC Class Codes: C10M 135/06 Esters, e.g. fats
• CPC Class Codes: C10M 2209/084 Acrylate; Methacrylate
• CPC Class Codes: C10M 2219/02 Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
• CPC Class Codes: C10M 2219/022 of hydrocarbons, e.g. olefines
• CPC Class Codes: C10M 2219/024 of esters, e.g. fats
• CPC Class Codes: C10M 2223/041 Triaryl phosphates
• CPC Class Codes: C10M 2223/045 Metal containing thio derivatives
• CPC Class Codes: C10M 2229/02 Unspecified siloxanes; Silicones
• CPC Class Codes: C10M 2229/05 containing atoms other than silicon, hydrogen, oxygen or carbon
• CPC Class Codes: C10N 2010/04 Groups 2 or 12
• CPC Class Codes: C10N 2040/20 Metal working
• CPC Class Codes: C10N 2040/22 with essential removal of material , e.g. cutting, grinding or drilling
• CPC Class Codes: C10N 2040/24 without essential removal of material , e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
• CPC Class Codes: C10N 2040/241 Manufacturing joint-less pipes
• CPC Class Codes: C10N 2040/242 Hot working
• CPC Class Codes: C10N 2040/243 Cold working
• CPC Class Codes: C10N 2040/244 of specific metals
• CPC Class Codes: C10N 2040/245 : Soft metals, e.g. aluminum
• CPC Class Codes: C10N 2040/246 : Iron or steel
• CPC Class Codes: C10N 2040/247 : Stainless steel
• CPC Class Codes: C10N 2070/02 : Concentrating of additives

Abstract

Functional fluids such as metal working fluids are disclosed which include an oil of lubricating viscosity, a sulfurized organic compound, and an amine derivative. The amine derivative is a hindered imine which is the reaction product obtained from reacting a primary amine connected to a tertiary alkyl group with an aldehyde or aldehyde reaction synthon. The inclusion of the hindered imine within the metal working fluid suppresses the generation of hydrogen sulfide gases during the use of the fluid thus improving the environmental and safety characteristics of the fluid.

Claims

1. A functional fluid, comprising:

(A) an oil of lubricating viscosity;

(B) a sulfurized organic compound selected from the group consisting of fats, alpha-olefins, fatty acid esters and triglycerides; and

(C) a hindered imine of general structural formula (I);

##STR4## wherein R₁, R₂, R₃ and R₄ are each independently an alkyl moiety containing 1 to 14 carbon atoms.

2. The fluid as claimed in claim 1, wherein R₄ is CH₂.

3. The fluid as claimed in claim 2, wherein R₁, R₂ and R₃ each independently an alkyl moiety containing 1 to 9 carbon atoms.

4. The fluid as claimed in claim 3, wherein the hindered imine (C) is present in the fluid in an amount in the range of from about 0.01% to about 5% by weight based on the weight of the fluid as a whole.

5. The fluid as claimed in claim 4, wherein the hindered imine (C) is present in an amount in the range of from about 0.10% to about 2.0% by weight based on the weight of the fluid as a whole and the functional fluid is a metal working fluid.

6. A metal working fluid, comprising:

(A) an oil of lubricating viscosity;

(B) a sulfurized organic compound selected from the group consisting of fats, fatty acid esters, alpha-olefins and triglycerides; and

(C) a hindered imine produced by reacting a primary amine connected to a tertiary alkyl group of general formula (II);

##STR5## wherein R₁, R₂ and R₃ are each independently an alkyl moiety containing 1 to about 14 carbon atoms, with an aldehyde or aldehyde reaction synthon.

7. The metal working fluid as claimed in claim 6, wherein the sulfurized organic compound (B) is obtained by reacting elemental sulfur with the organic compound in the presence of a catalyst.

8. The metal working fluid as claimed in claim 7, wherein the catalyst is selected from the group consisting of phosphoric acid and salts thereof effective in catalyzing the sulfurization of the organic compound and the reacting is carried out at a temperature in the range of about 100°

C. to about 250°

C.

9. The metal working fluid as claimed in claim 8, wherein the sulfurized organic compound of (B) is present in an amount of 0.1% to 20% by weight and the hindered imine (C) is present in an amount of about 0.1% to about 5% by weight based on the weight of the fluid.

10. The metal working fluid of claim 6, wherein the amine of formula (II) is t-butylamine.

11. The metal working fluid of claim 6, wherein the amine of formula (II) is reacted with paraformaldehyde.

12. The metal working fluid of claim 9, wherein the amine of formula (II) is t-butylamine which is reacted with paraformaldehyde.

13. A metal working fluid, comprising:

(A) an oil of lubricating viscosity;

(B) a sulfurized organic compound obtained by reacting an unsaturated aliphatic compound containing 12 to 28 carbon atoms with elemental sulfur in the presence of a catalyst selected from the group consisting of phosphoric acid and salts thereof; and

(C) a hindered imine of the following general structural formula;

##STR6## wherein R₁, R₂, and R₃ are each independently an alkyl moiety containing 1 to 9 carbon atoms.

14. The fluid as claimed in claim 13, wherein the sulfurized organic compound (B) is present in an amount of 0.1% to 20% by weight and the hindered imine (C) is present in an amount of about 0.1% to about 5% by weight based on the weight of the fluid.

15. The fluid as claimed in claim 14, wherein the aliphatic compound is selected from the group consisting of a fatty acid and a fatty acid ester of a monohydric alcohol.

16. The fluid as claimed in claim 15, wherein the aliphatic compound is a fatty acid containing 14 to 22 carbons.

17. The fluid as claimed in claim 13, wherein the catalyst is phosphoric acid.