US3840574A - Process for the preparation of heatresistant and lightfast fatty acids - Google Patents

Process for the preparation of heatresistant and lightfast fatty acids Download PDF

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Publication number
US3840574A
US3840574A US00166993A US16699371A US3840574A US 3840574 A US3840574 A US 3840574A US 00166993 A US00166993 A US 00166993A US 16699371 A US16699371 A US 16699371A US 3840574 A US3840574 A US 3840574A
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US
United States
Prior art keywords
fatty acids
acid
carbon atoms
lightfast
acids
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Expired - Lifetime
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US00166993A
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English (en)
Inventor
S Naskar
G Renckhoff
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Dynamit Nobel AG
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Dynamit Nobel AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/08—Refining
    • C11C1/10—Refining by distillation
    • C11C1/103—Refining by distillation after or with the addition of chemicals

Definitions

  • This invention relates to the production of heat-resistant and lightfast fatty acids and more particularly to a process for producing such fatty acids in the presence of certain polycarboxylic acid additives.
  • the fatty acids can be heated, according to this invention in the presence of the polycarboxylic acids or the alkyl esters thereof by themselves.
  • an optimum effect is attained with respect to the light and thermal stability, and the color of the distilled fatty acid.
  • the treatment period is dependent on the treatment temperature. This period is about 2 to about 3 hours in case of a temperature of about 250 C. to 260 C., about 3 to about 4 hours at about 230 C. to about 240 C., and and about 5 to about 6 hours at about 220 C. to about 230 C.
  • the amount of the additives, i.e. acids or esters used to treat the fatty acids, is dependent on the type and quality of the crude fatty acids or the crude fatty acid mixtures.
  • C -C fatty acids stemming from palm nut oil or coconut oil and being extremely light-sensitive and heatsensitive, it is possible to add about 0.1 to about 0.2% of the aliphatic, cycloaliphatic, or hydroxypolycarboxylic acids, or the lower alkyl esters of the polycarboxylic acids, and about 0.1 to about 0.2% of the alkyl esters of titanic and/or zirconic acid;
  • sufiicient amounts are about 0.05 to about 0.1% of the polycarboxylic acids or the lower alkyl esters thereof, and about 0.05 to about 0.2% of alkyl esters of titanic or zirconic acid. It will be appreciated that larger amounts of the polycarboxylic acids or esters, e.g. up to about 0.5%, may be employed,
  • the polycarboxylic acids and the titanic or zirconic acid are left bound in the distillation residue, together with the impurities contained in the fatty acid.
  • the process of this invention has the advantage that the amount of unsaponifiable compounds in the distillate is no larger than in the distillate of the untreated fatty acid.
  • distillation residue of the thus-treated fatty acid does not contain any newly formed condensation products, which occur in the conventional treatment methods operating with boric acid or the esters thereof.
  • the boron compounds which have the effect of Lewis catalysts, promote the formation of unsaponifiable, undistillable condensation products.
  • high-boiling derivatives of the aliphatic and cycloaliphatic polycarboxylic acids and undistillable titanic acid and/or zirconic acid compounds are found in the distillation residue.
  • polycarboxylic acids to be employed according to this invention are oxalic acid, maleic acid, fumaric, itaconic, succinic acid, adipic acid, malic acid, tartaric acid, citric acid, and cyclopropane-, cyclobutane-, and cyclohexanedicarboxylic acid.
  • saturated and unsaturated aliphatic polycarboxylic acids are suitable.
  • the alkyl esters of these acids include partial and full esters such as monomethyl maleate, monobutyl itaconate and dimethyl maleate.
  • the source of the crude fatty acids can be natural fats and oils, as well as-synthetic fatty acids.
  • a large portion of these fatty acids is formed as a technical product during various stages of the refinery of nutrient oils and fats, for example during the deacidification by neutralization with an alkali, or during the direct distillation of nutrient oils and fats with a higher content of free acids under vacuum, decolorization, and deodorization.
  • the color stability characteristics of the fatty acids, treated according to this invention and those of the untreated fatty acids were determined by the heating of samples in a small glass tube having a diameter of 14 millimeters and a filling level of 115 millimeters to 200 C. during a period of 6 hours. This heating test was con-
  • the fatty acid blend is understood to mean the distillation cut of the untreated fatty acids containing predominantly (at least 80%) of fatty acids of the chain length set forth in the table.
  • the amount of additive employed is based on the weight of the fatty acids to be treated.
  • the test tubes were in each case covered by a cap.
  • the color intensity was measured in iodine color number units, wherein the iodine color number indicates how many milligrams of free iodine are contained in 100 milliliters of an aqueous iodine-potassium iodide solution at the same depth of color when measuring at a layer thickness of millimeters.
  • a fatty-acid forerunning (ii-4%) and a main run or fraction (90- 93%).
  • the first run from most of the treated technical fatty acids exhibits a strongly unpleasant odor and is not utilized.
  • amounting to 46% by weight of the unsaponifiable component was determined.
  • the hazen color unit of freshly distilled samples was determined.
  • the iodine color number of samples maintained for 6 hours at 200 C. was observed.
  • the iodine color number and the hazen unit were measured in the Lovibond 1000 comparator and the accessories thereof by Tintometer.
  • a process for the preparation of heat-resistant and lightfast fatty acids from crude fatty acids having a chain length of (l -C which comprises heating the crude fatty acids or the mixtures thereof with a polycarboxylic acid selected from the group consisting of an aliphatic polyor hydroxypolycarboxylic acid containing 2 to 10 carbon atoms, and a cycloaliphatic polycarboxylic acid containing 5 to 10 carbon atoms or a lower alkyl ester of said polycarboxylic acid to temperatures of about C. to about 280 C., for a period suflicient to improve the heat-resistant and lightfastness of the fatty acids and subsequently distilling ofif the fatty acids under a vacuum.
  • a polycarboxylic acid selected from the group consisting of an aliphatic polyor hydroxypolycarboxylic acid containing 2 to 10 carbon atoms, and a cycloaliphatic polycarboxylic acid containing 5 to 10 carbon atoms or a lower alkyl este
  • a process for the preparation of heat-resistant and lightfast fatty acids from crude fatty acids having a chain length of C -C which comprises heating the crude fatty acids or the mixtures thereof, with an additive selected from the group consisting of an aliphatic polycarboxylic acid or hydroxycarboxylic acid containing 2 to 10 carbon atoms, a cycloaliphatic polycarboxylic acid containing 5 to 10 carbon atoms, and an alkyl ester of said acids containing from 1 to 4 carbon atoms in the alkyl group to a temperature of from about 180 C. to about 280 C. under normal pressure for a period of from about 0.5 to about 8 hours and subsequently distilling off the fatty acids under a vacuum.
  • an additive selected from the group consisting of an aliphatic polycarboxylic acid or hydroxycarboxylic acid containing 2 to 10 carbon atoms, a cycloaliphatic polycarboxylic acid containing 5 to 10 carbon atoms, and an alkyl ester of said acids

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
US00166993A 1970-08-03 1971-07-28 Process for the preparation of heatresistant and lightfast fatty acids Expired - Lifetime US3840574A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2038468A DE2038468C3 (de) 1970-08-03 1970-08-03 Verfahren zur Herstellung hitzebeständiger und lichtstabiler Fettsäuren

Publications (1)

Publication Number Publication Date
US3840574A true US3840574A (en) 1974-10-08

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Family Applications (1)

Application Number Title Priority Date Filing Date
US00166993A Expired - Lifetime US3840574A (en) 1970-08-03 1971-07-28 Process for the preparation of heatresistant and lightfast fatty acids

Country Status (9)

Country Link
US (1) US3840574A (fr)
JP (1) JPS5221005A (fr)
BE (1) BE770539R (fr)
DE (1) DE2038468C3 (fr)
DK (1) DK138996C (fr)
FR (1) FR2107811A6 (fr)
GB (1) GB1353175A (fr)
IT (1) IT1044914B (fr)
NL (1) NL7108952A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4650611A (en) * 1981-07-20 1987-03-17 Henkel Kommanditgesellschaft Auf Aktien Process for the preparation of fatty acid alkyl esters having improved processing properties

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3125494B1 (fr) 2021-07-20 2023-09-15 Psa Automobiles Sa Procédé et dispositif de contrôle d’un système de régulation adaptative de vitesse d’un véhicule

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4650611A (en) * 1981-07-20 1987-03-17 Henkel Kommanditgesellschaft Auf Aktien Process for the preparation of fatty acid alkyl esters having improved processing properties

Also Published As

Publication number Publication date
DK138996C (da) 1979-04-23
FR2107811A6 (fr) 1972-05-12
GB1353175A (en) 1974-05-15
JPS5221005A (en) 1977-02-17
JPS5546678B2 (fr) 1980-11-25
DE2038468A1 (de) 1972-02-10
NL7108952A (fr) 1972-02-07
BE770539R (fr) 1972-01-27
DE2038468C3 (de) 1979-08-30
DE2038468B2 (de) 1979-01-04
IT1044914B (it) 1980-04-21
DK138996B (da) 1978-11-27

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