US3373174A - A method for improving color and the color and odor stability of fatty amides - Google Patents

A method for improving color and the color and odor stability of fatty amides Download PDF

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Publication number
US3373174A
US3373174A US419222A US41922264A US3373174A US 3373174 A US3373174 A US 3373174A US 419222 A US419222 A US 419222A US 41922264 A US41922264 A US 41922264A US 3373174 A US3373174 A US 3373174A
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US
United States
Prior art keywords
amide
color
solvent
borohydride
amides
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US419222A
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English (en)
Inventor
Edgar S Hammerberg
Sydney H Shapiro
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Armour and Co
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Armour and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Armour and Co filed Critical Armour and Co
Priority to US419222A priority Critical patent/US3373174A/en
Priority to SE16126/65A priority patent/SE311150B/xx
Priority to FR42395A priority patent/FR1459655A/fr
Priority to DE19651518520 priority patent/DE1518520A1/de
Priority to GB53676/65A priority patent/GB1070709A/en
Application granted granted Critical
Publication of US3373174A publication Critical patent/US3373174A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton

Definitions

  • This invention broadly relates to fatty amides and more particularly to a method for improving the color and the color and odor stability of fatty amides, and to the composition produced therefrom.
  • An object of this invention is to provide a novel purification process for fatty amides.
  • Another object is to provide an improved purification process for fatty amides which is economical.
  • Still another object is to provide a purification process for fatty amides which is relatively easy to perform, even by unskilled technicians.
  • a further object is to provide a purification process 1 which improves the original color of fatty amides.
  • a still further object is to provide a purification process which imparts color and odor stability to fatty amides.
  • Another object is to provide a purification process which leaves no undesirable residue in the finished amide so that the amide may be either stored or further processed without subsequent deleterious effect.
  • the invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the composition possessing the features, properties, and the relation of constituents, which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
  • amides may be greatly improved in amide content and reduced color by subjecting the crude amide to washing with a hydrocarbon to remove free fatty acids, nitriles, colored bodies, etc.,
  • the borohydride that may be used may comprise sodium borohydride, potassium borohydride and quaternary ammonium borohydride.
  • the hydrocarbon that is used to wash the amide is one having from 3 to 8 carbon atoms, and preferably, 5 to 8 carbon atoms so that the washing need not be done in a pressurized system to prevent volatilization of the hydrocarbon.
  • the amount of hydrocarbon used is from two to five times that of the amide and the washing is performed at room temperature. However, additional washes and even temperatures above room temperature may be used where the amide is not too soluble in the hydrocarbon, such as with saturated amides.
  • Example I A seven foot glass column, 1% inches in diameter, is filled with Armid O flakes (oleylamide).
  • Skelly-solve B (a commercial mixture of hydrocarbons, B referring to a hexane type with a boiling range of 146 to 156 F.) is then added flowing either up or down through the bed.
  • the amide is allowed to soak in the Skelly-solve B for approximately one hour before additional Skelly-solve B is passed through the bed.
  • the column is drained, and sodium borohydride added (0.05%, on the basis of weight of amide charged).
  • the flakes are then transferred to a distilling flask, and the solvent removed at reduced pressure. Yield, color, and percent free fatty acids are then measured.
  • Yields are generally in the range of 88.594%.
  • Example 11 200 gal. heptaiie is added to a 500 gal. Dopp kettle. Temperature of the heptane is 56 F. This kettle has twelve counter-rotating arms for mixing. However, no agitation is used during the Washing cycle because the soft wet flakes would be destroyed and the arms help to stabilize the bed. 1500 lbs. of Armid O flakes (2.85% F.F.A. and Gardner 4 color) is then added and the bed is leveled. At this stage about 3-4 inches of heptane is above the level of the Armid O. The Armid O is allowed to soak for one hour.
  • the heptane is then drained from the bottom of the kettle and fresh lieptane is simultaneou ly added to the top, maintaining a 4-5 inch level of heptane above the amide. After a total of 400 gal. has been added, the heptane is drained as completely as possible. 4 lb. sodium borohydride is then added. The batch is melted and the remaining heptane is distilled off. After all the heptane has been removed, the batch is drained, cooled, and packed in 50' lb. fiber drums. Yield is 1409 lbs. with a Gardner color of 1 and free fatty acid content of 0.1% as oleic acid.
  • Example 111 Armid (not solvent Washed) having an initial Gardner color of 4 is treated with 0.05% sodium borohydride and subjected to a heat stability test.
  • the test consists of holding Armid O in a capped 2 oz. bottle at an elevated temperature for at least 18 hours. A sample is considered to have passed the test if the final color is not darker than Gardner 10.
  • a control is also run concurrently without the borohydride. It will be found that the final color of the control will be about Gardner 11-12, whereas that containing borohydride will be about Gardner 7-8 or even better.
  • Example IV the batch size comprises a 2000 lbs. lot of Armid O.
  • the amide is solvent-washed, treated with 0.05% sodium borohydride, stripped of solvent, and drummed. The drums are then shipped to a distant loca- Table 11 illustrates the type of results that are obtainable when the amide of the above example is subjected to heat stability test such as described in Example Ill:
  • Example V A 500 gallon Dopp kettle is charged With 265 gallons of heptane and cooled to -75" P. Then 2000-2200 lbs. of Armid O flakes are added and the bed is leveled so that a few inches of solvent will be above the amide. The batch is soaked for 45 min., and then the solvent is drained from the bottom at a rate of about 3 gallons per minute. Simultaneously, fresh heptane is added at 65-75 F. to the top of the batch, maintaining a 2-3 inch level of lieptane above the amide.
  • the ratio of solvent to amide is preferably 3 parts to 1.
  • the washing is accomplished usually at room temperature, although with the higher amides, temperatures above room temperature to facilitate the Washing may be used.
  • the amides to which the technique of this invention has particular application are the fatty amides such as the C to C saturated and unsaturated amides, specifically, octyl amide, nonyl amide, decyl amide, undecyl amide, dodecyl amide, tridecyl amide, tetradecyl amide, pentadecyl amide, hexadecyl amide, heptadecyl amide, octadecyl amide, nonadecyl amide, eicosyl amide, henicosyl amide, docosyl amide, octenyl amide, nonenyl amide, decentyl amide, undecenyl amide, dodecenyl amide, tridecenyl amide, tetradecnyl amide, pentadecenyl amide, hexadecenyl amide, hepta
  • the borohydrides which are operable in the technique of this invention are sodium borohydride, potassium borohydride and quaternary ammonium borohydride.
  • the concentration ranges vary between 0.05 to 0.2% by weight of the amide.
  • a process for improving the color and odor stability of fatty amides comprising admixing 0.05 to 0.2% by weight of an alkaline-type borohydride with said fatty amides.
  • a process for improving the color and the color and odor stability of fatty amides comprising Washing said fatty amides with hydrocarbons, and then subsequently admixing 0.05 to 0.2% by weight of an alkaline-type borohydride with said fatty amides.
  • a color and odor stable fatty amide composition comprising at least one fatty amide admixed with 0.05 to 0.2% by weight of an alkaline-type borohydride.
  • composition of claim 5 wherein said borohydride comprises sodium borohydride.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US419222A 1964-12-17 1964-12-17 A method for improving color and the color and odor stability of fatty amides Expired - Lifetime US3373174A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US419222A US3373174A (en) 1964-12-17 1964-12-17 A method for improving color and the color and odor stability of fatty amides
SE16126/65A SE311150B (enExample) 1964-12-17 1965-12-13
FR42395A FR1459655A (fr) 1964-12-17 1965-12-15 Nouvelles amides grasses et procédé pour leur préparation
DE19651518520 DE1518520A1 (de) 1964-12-17 1965-12-16 Verfahren zur Verbesserung der Bestaendigkeit von Fettsaeureamiden
GB53676/65A GB1070709A (en) 1964-12-17 1965-12-17 Process for the stabilisation of amides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US419222A US3373174A (en) 1964-12-17 1964-12-17 A method for improving color and the color and odor stability of fatty amides

Publications (1)

Publication Number Publication Date
US3373174A true US3373174A (en) 1968-03-12

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US419222A Expired - Lifetime US3373174A (en) 1964-12-17 1964-12-17 A method for improving color and the color and odor stability of fatty amides

Country Status (5)

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US (1) US3373174A (enExample)
DE (1) DE1518520A1 (enExample)
FR (1) FR1459655A (enExample)
GB (1) GB1070709A (enExample)
SE (1) SE311150B (enExample)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527821A (en) * 1968-01-16 1970-09-08 Gulf Research Development Co Olefinic hydrocarbon stabilized by sodium borohydride particles
US3529001A (en) * 1968-07-10 1970-09-15 Us Agriculture Process for decolorizing n,n-disubstituted amides
US5419815A (en) * 1992-08-15 1995-05-30 Hoechst Ag Process for purifying fatty acid amides
WO1995018095A1 (en) * 1993-12-27 1995-07-06 Finetex, Inc. Process for making n-acyl taurides
WO1996040619A1 (en) * 1995-06-07 1996-12-19 The Procter & Gamble Company Process for preparing amides of n-alkyl polyhydroxyalkyl amines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5728852A (en) * 1995-08-09 1998-03-17 Kao Corporation Method for producing monohydroxyalkylamides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB802860A (en) * 1957-04-03 1958-10-15 Standard Oil Co Refining alcohols
US3159276A (en) * 1963-05-03 1964-12-01 Allied Chem Ethanolamines
US3207790A (en) * 1961-07-06 1965-09-21 Dow Chemical Co Process for reducing the color of discolored alkanolamines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB802860A (en) * 1957-04-03 1958-10-15 Standard Oil Co Refining alcohols
US3207790A (en) * 1961-07-06 1965-09-21 Dow Chemical Co Process for reducing the color of discolored alkanolamines
US3159276A (en) * 1963-05-03 1964-12-01 Allied Chem Ethanolamines

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527821A (en) * 1968-01-16 1970-09-08 Gulf Research Development Co Olefinic hydrocarbon stabilized by sodium borohydride particles
US3529001A (en) * 1968-07-10 1970-09-15 Us Agriculture Process for decolorizing n,n-disubstituted amides
US5419815A (en) * 1992-08-15 1995-05-30 Hoechst Ag Process for purifying fatty acid amides
WO1995018095A1 (en) * 1993-12-27 1995-07-06 Finetex, Inc. Process for making n-acyl taurides
US5434276A (en) * 1993-12-27 1995-07-18 Finetex, Inc. Process for making N-acyl taurides
WO1996040619A1 (en) * 1995-06-07 1996-12-19 The Procter & Gamble Company Process for preparing amides of n-alkyl polyhydroxyalkyl amines

Also Published As

Publication number Publication date
SE311150B (enExample) 1969-06-02
GB1070709A (en) 1967-06-01
DE1518520A1 (de) 1969-03-06
FR1459655A (fr) 1966-11-18

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