Process for reducing the levels of fatty acid contaminants in polyhydroxy fatty acid amide surfactants

• US 5,188,769 A
• Filed: 03/26/1992
• Issued: 02/23/1993
• Est. Priority Date: 03/26/1992
• Status: Expired due to Term

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Scheibel, Jeffrey J., Gosselink, Eugene P., Mao, Mark H., Connor, Daniel S., Severson, Roland G. Jr., Murch, Bruce P.
• Primary Examiner(s): Albrecht, Dennis
• Application Number:
  US07/857,853
• Time in Patent Office: 334 Days
• Field of Search: 536/53, 554/61, 554/65, 554/68, 252/357, 252/529, 252/548, 252/551
• US Class Current: 510/433
• CPC Class Codes: C07C 231/02 from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
• CPC Class Codes: C11D 1/525 Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
• CPC Class Codes: Y10S 516/07 Organic amine, amide, or n-base containing

Abstract

The synthesis of polyhydroxy fatty acid amide surfactants exemplified by the compound C₁₁ H₂₃ C(O)N(CH₃)CH₂ [CHOH]₄ CH₂ OH by reacting a fatty acid ester with an N-alkyl sugar amine can result in contamination of the product surfactant by residual sources of fatty acids. These residual fatty acids may be unacceptable in high sudsing detergent compositions, such as dishwashing liquids, especially with Ca or Mg cations. The process of this invention reacts such contaminants with alkyl amines or, especially, ethanolamine, to convert them into fatty alkyl- or alkanolamides, which are quite acceptable in fully-formulated detergent compositions for home or industrial use.

Claims

1. In a process for preparing a primary reaction product comprising a polyhydroxy fatty acid amide surfactant, said reaction product containing undesirable amounts of free fatty acids or nascent source of fatty acids, said process comprising a primary reaction between a sugar-derived or glyceraldehyde-derived polyhydroxy amine and a fatty acid ester, said primary reaction being carried out at a temperature below about 100°

C. so as to minimize formation of cyclized by-products in said reaction product, the improvement which comprises running the primary reaction under substantially water-free conditions, whereby the formation of free fatty acids and soaps is minimized, and adding to said primary reaction product an amine reaction which is a member selected from the group consisting of ammonia, short-chain alkyl amines and short-chain hydroxyalkyl amines and subjecting said reaction product to a secondary reaction, whereby the total level of residual nascent and free fatty acid present in said primary reaction product is reduced to below about 1%, by weight.

2. A process according to claim 1, wherein said primary reaction product is prepared by a primary reaction of a C₈ -C₂₂ fatty acid ester and a polyhydroxy amine.

3. A process according to claim 2, wherein the fatty acid ester is a methyl ester, and said primary reaction is carried out in the presence of a base catalyst.

4. A process according to claim 3, wherein the primary reaction is carried out in a hydroxy solvent in the presence of an alkoxide catalyst.

5. A process according to claim 1, wherein the amine reaction in said secondary reaction is a C₁ -C₄ primary alkyl amine or C₁ -C₄ primary hydroxyalkyl amine.

6. A process according to claim 5, wherein said amine reactant used in said secondary reaction is monoethanolamine, and wherein said secondary reaction is carried out at a temperature of from about 50°

C. to about 90°

C.

9. In a process for preparing a detergent composition containing a source of calcium ions, magnesium ions, or mixtures thereof, said detergent composition comprising a polyhydroxy fatty acid amide surfactant which is prepared by reacting a fatty acid ester and a sugar-derived or glyceraldehyde-derived polyhydroxy amine to provide a polyhydroxy fatty acid amide surfactant reaction product which is undersirably contaminated with interfering amounts of residual fatty acids or nascent fatty acids, the improvement which comprises adding to said detergent composition the polyhydroxy fatty acid amide surfactant prepared according to claim 1 which is substantially free of said residual fatty acids or nascent fatty acids, whereby undesirable interactions between said calcium or magnesium ions and said residual fatty acid are minimized.

10. A process according to claim 9 wherein said detergent composition is in liquid form and contains at least about 0.10% by weight of added calcium ion, magnesium ions, or mixtures thereof and less than about 1.0% by weight of residual fatty acid or nascent fatty acids.

11. A process according to claim 10 wherein said liquid detergent composition contains a source of calcium and magnesium ions and comprises less than about 0.3% by weight of residual fatty acids or nascent fatty acids.

12. A process according to claim 10 wherein said liquid detergent composition contains a source of calcium ions and comprises less than about 0.1% by weight of residual fatty acids or nascent fatty acids.

7. An improved process for preparing polyhydroxy fatty acid amide surfactants comprising:

(a) a primary amidation reaction conducted under substantially water-free conditions between a fatty acid ester and a sugar-derived or glyceraldehyde-derived polyhydroxyamine to prepare a polyhydroxy fatty acid amide surfactant which is contaminated with residual nascent fatty acids, followed by;

(b) a secondary reaction which comprises admixing and reacting with the reaction product of primary reaction (a) an amine reactant which is a member selected from the group consisting of ammonia, short-chain alkyl amines and short-chain hydroxy alkly amines, whereby the level of residual nascent fatty acids and free fatty acids is lowered to below about 0.5% by weight in the final surfactant.

8. A process according to claim 7 wherein said amine reactant is a member selected from the group consisting of monoethanolamine and 1-amino-2-propanol.