EP0108571A2 - Verfahren zum Reinigen von ungesättigten fetten Ölen - Google Patents

Verfahren zum Reinigen von ungesättigten fetten Ölen Download PDF

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Publication number
EP0108571A2
EP0108571A2 EP83306586A EP83306586A EP0108571A2 EP 0108571 A2 EP0108571 A2 EP 0108571A2 EP 83306586 A EP83306586 A EP 83306586A EP 83306586 A EP83306586 A EP 83306586A EP 0108571 A2 EP0108571 A2 EP 0108571A2
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EP
European Patent Office
Prior art keywords
oil
process according
unsaturated
fatty acid
unsaturated fatty
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.)
Withdrawn
Application number
EP83306586A
Other languages
English (en)
French (fr)
Other versions
EP0108571A3 (de
Inventor
Hideo Ishiwatari
Suzuko Koshiba
Takeshi Koresawa
Masanori Aizawa
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.)
Dai-Ichi Croda Chemicals KK
Shiseido Co Ltd
Original Assignee
Dai-Ichi Croda Chemicals KK
Shiseido Co Ltd
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 Dai-Ichi Croda Chemicals KK, Shiseido Co Ltd filed Critical Dai-Ichi Croda Chemicals KK
Publication of EP0108571A2 publication Critical patent/EP0108571A2/de
Publication of EP0108571A3 publication Critical patent/EP0108571A3/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/10—Refining fats or fatty oils by adsorption
    • 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
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation

Definitions

  • the present invention relates to a process for treating unsaturated fatty oils to obtain a purified unsaturated neutral oil of low odor, low color and high stability. More specifically, the present invention relates to a process for substantially eliminating the characteristic odor and color of such an unsaturated fatty oil, such that the purified fatty oil product is essentially "water-white” and has an odor level no greater than that of heavy mineral oil USP.
  • unsaturated fatty oils comprise a triglyceride of a higher fatty acid or an ester of a higher fatty alcohol with a higher fatty acid. Whilst they contain a relatively large number of carbon atoms, they are nevertheless liquid or viscous because of their unsaturation. They are of broad utility. Synthetic unsaturated oils such as oleyl oleate are known and are frequently used as, for example, starting materials in the production of cosmetics. Some unsaturated oils may also be useful as components of pharmaceutical preparations or dietary supplements.
  • One known way of stabilizing an unsaturated fatty oil of which the fatty acid portion is a polyene, having two or more unsaturated bonds which may or may not be conjugated is to subject it to selective hydrogenation to hydrogenate a small portion of the total polyene content.
  • the product so formed has greatly improved storage stability.
  • this selective hydrogenation treatment is not satisfactory, because it does not sufficiently reduce or eliminate the characteristic smell of the unsaturated fatty oil starting material. For instance, even hardened beef tallow or purified stearic acid which have been treated in this way still have their characteristic smell.
  • the oil is subjected to column chromatography: the oil is dissolved in a non-polar solvent, and passed at least once through a column of an adsorbent for the polar impurities such as pigments and odor-producing substances. The solvent is then evaporated off.
  • the process of this invention produces a product which is much more stable against oxidative deterioration than oils which have been treated simply to selective hydrogenation or simply to column chromatography.
  • the product is also essentially "water-white,” and has an odor level no greater than that of heavy mineral oil USP.
  • water-white is frequently used in industry to describe a liquid which is clear and essentially colorless in moderately thick layers.
  • the process of the invention is useful for purifying unsaturated fatty oils comprising unsaturated esters of higher fatty alcohols with higher fatty acids or .the triglycerides of unsaturated higher fatty acids.
  • oils such as land animal oils (e.g., beef tallow, mink oil, and neats-foot oil), fish oils (e.g., orange r-oughy-oil, cod liver oil, and shark liver oil), marine animal oils (e.g., sperm oil), and vegetable oils (e.g., olive oil, palm oil, peanut oil, corn oil, castor oil, coconut oil, tsubaki oil, tea oil, sesame oil, almond oil, soybean oil, avocado oil, sunflower oil, safflower oil, wheat germ oil, apricot kernal oil, peach kernal oil, meadowfoam oil, jojoba oil, rapeseed oil, and sasanqua oil), and synthetic unsaturated oils such as crude oleyl ole
  • any procedure may be used which can convert the polyene fatty acid or alcohol moiety in the unsaturated ester or the triglyceride, selectively into a monoene moiety and simultaneously reduce trace amounts of peroxides, aldehydes, ketones, and other impurities contained in the unsaturated fatty oil.
  • a typical example of such a procedure is a catalytic hydrogenation in which a small amount of a nickel or copper-chromium catalyst is added to the unsaturated fatty oil, and the mixture contacted with hydrogen under atmospheric or elevated pressure with heating.
  • the selective hydrogenation is carried out at a temperature of 100 to 200°C under a pressure of not more than 3 atm.
  • a suitable catalyst is that available under the name "NIKKI N 103B" (manufactured by Nikki Kagaku KK of Tokyo, Japan).
  • Other examples include those available under the trade names “Nysel” (manufactured by Harshaw Catalysts of Beachwood, Ohio) and “Girdler” (manufactured by United Catalysts Inc. of Louisville, Kentucky).
  • the amount of catalyst used may be small and is usually not nore than 2 - 3% by weight of the unsaturated fatty oil.
  • non-polar solvent we prefer to use aliphatic hydrocarbons (e.g., petroleum ether, n-hexane, n-pentane), halogenated hydrocarbons (e.g., carbon tetrachloride), and similar liquids.
  • aliphatic hydrocarbons e.g., petroleum ether, n-hexane, n-pentane
  • halogenated hydrocarbons e.g., carbon tetrachloride
  • the number of passes through the column and the dwell time on each pass can vary and will be chosen as best in any particular case having regard to the required extent of purification, the nature of the non-polar solvent and the nature of the adsorbent.
  • the selective hydrogenation effects reduction of any peroxides, aldehydes, and ketones which are present, to produce a substantially colorless, transparent and odorless unsaturated fatty oil product. Further, at least some of the oxidizable substances are thus reduced to non-oxidizable substances so that the resistance of the unsaturated fatty oil product to oxidative deterioration with time is increased.
  • the column chromatography (before or after the selective hydrogenation) removes polar impurities from the unsaturated fatty oil, whereby any color is reduced and the resistance to oxidative deterioration is enhanced.
  • the unsaturated neutral oil produced is normally substantially odorless and colorless and has an excellent storage stability.
  • This orange roughy-oil had an acid value of 0.19, a saponification value of 102.8 and an iodine value of 89.5.
  • the orange roughy-oil was subjected to selective hydrogenation under the conditions as shown in Table 1.
  • the unsaturated fatty oils obtained by the above selective hydrogenation had the properties shown in Table 2.
  • the unsaturated fatty oil there was used a yellow brown sperm oil having a strong characteristic smell, of which the properties were as shown in Table 7.
  • the sperm oil was subjected to selective hydrogenation under the conditions as shown in Table 8.
  • the purified oil was subjected to selective drogenation under the conditions as shown in Table 12
  • Samples (50 g) of the purified unsaturated fatty oils obtained in Examples 1, 3 and 5 (Samples A, B and C), the intermediary purified unsaturated fatty oils (unsaturated fatty oils subjected to selective hydrogenation alone) (Samples D and E) and the intermediary purified unsaturated fatty oil (unsaturated fatty oil subjected to recirculated column chromatography alone) (Sample F) were charged in 100 ml volume glass flasks and allowed to stand in a desiccator at 50 + 2°C. At intervals of one hour, the POV value was measured and the smell was examined. As to the smell, the results after 30 days are shown in Table 14. The POV value is summarized in Figure 1 of the accompanying drawing.
  • the accompanying drawing shows the test results on the resistance to oxidation with time of the unsaturated fatty oils as follows: A----- Example 1; B----Example 2; C----- Example 3; D----- Orange raffi-oil treated by selective hydrogenation alone; E----- sperm oil treated by selective hydrogenation alone; F----- olive oil treated by circulatory column chromatography alone.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
EP83306586A 1982-11-04 1983-10-28 Verfahren zum Reinigen von ungesättigten fetten Ölen Withdrawn EP0108571A3 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP194015/82 1982-11-04
JP19401582A JPS5984992A (ja) 1982-11-04 1982-11-04 油脂の精製方法

Publications (2)

Publication Number Publication Date
EP0108571A2 true EP0108571A2 (de) 1984-05-16
EP0108571A3 EP0108571A3 (de) 1985-03-06

Family

ID=16317529

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83306586A Withdrawn EP0108571A3 (de) 1982-11-04 1983-10-28 Verfahren zum Reinigen von ungesättigten fetten Ölen

Country Status (2)

Country Link
EP (1) EP0108571A3 (de)
JP (1) JPS5984992A (de)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4629588A (en) * 1984-12-07 1986-12-16 W. R. Grace & Co. Method for refining glyceride oils using amorphous silica
US4880574A (en) * 1984-12-07 1989-11-14 W. R. Grace & Co.-Conn. Method for refining glyceride oils using partially dried amorphous silica hydrogels
US4902527A (en) * 1987-05-14 1990-02-20 Lever Brothers Company Confectionery fats
EP0424066A3 (en) * 1989-10-16 1991-10-16 The Procter & Gamble Company Polyol polyester synthesis
EP0429995A3 (en) * 1989-11-20 1991-12-11 Helios Oljarna Domzale D.O.O. Process for hydrogenation of oils
EP0412624A3 (en) * 1989-08-08 1991-12-18 W.R. Grace & Co.-Conn. Method for refining wax esters using amorphous silica
TR24766A (tr) * 1989-10-16 1992-05-01 Procter & Gamble Poliol polyester sentezi.
US5401862A (en) * 1992-02-19 1995-03-28 Nestec S.A. Process for decoloring fatty acid esters
US6280659B1 (en) * 1996-03-01 2001-08-28 David W. Sundin Vegetable seed oil insulating fluid
WO2004065532A1 (de) * 2003-01-22 2004-08-05 Cognis Ip Management Gmbh Geruchsminderung von ölkomponenten durch adsorption mit polymeren adsorbentien
RU2352549C2 (ru) * 2002-04-29 2009-04-20 Дау Глобал Текнолоджиз Инк. Интегрированные химические способы промышленного применения растительных масел из семян
WO2009105351A1 (en) * 2008-02-21 2009-08-27 Dow Global Technologies Inc. Separation of natural oil-derived aldehydes or hydroxy methyl esters using process chromatography
EP2196523A4 (de) * 2007-10-12 2011-04-20 Nippon Suisan Kaisha Ltd Verfahren zur herstellung von hochreinem kaiserbarsch-öl
JP2024511558A (ja) * 2021-03-02 2024-03-14 カーギル インコーポレイテッド バイオ原料油誘電性流体を製造するための方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0733350B2 (ja) * 1985-12-07 1995-04-12 日清製油株式会社 改質された中鎖脂肪酸トリグリセリドの製造法
JPH02196738A (ja) * 1989-01-25 1990-08-03 Nobuhisa Shimizu 高級アルコールの製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2589097A (en) * 1947-06-19 1952-03-11 Procter And Gamblc Company Retardation of development of reversion flavor in hydrogenated fats and oils

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4629588A (en) * 1984-12-07 1986-12-16 W. R. Grace & Co. Method for refining glyceride oils using amorphous silica
US4880574A (en) * 1984-12-07 1989-11-14 W. R. Grace & Co.-Conn. Method for refining glyceride oils using partially dried amorphous silica hydrogels
US4902527A (en) * 1987-05-14 1990-02-20 Lever Brothers Company Confectionery fats
EP0412624A3 (en) * 1989-08-08 1991-12-18 W.R. Grace & Co.-Conn. Method for refining wax esters using amorphous silica
EP0424066A3 (en) * 1989-10-16 1991-10-16 The Procter & Gamble Company Polyol polyester synthesis
TR24766A (tr) * 1989-10-16 1992-05-01 Procter & Gamble Poliol polyester sentezi.
US5318790A (en) * 1989-10-16 1994-06-07 The Procter & Gamble Company Polyol polyester purification
EP0429995A3 (en) * 1989-11-20 1991-12-11 Helios Oljarna Domzale D.O.O. Process for hydrogenation of oils
US5401862A (en) * 1992-02-19 1995-03-28 Nestec S.A. Process for decoloring fatty acid esters
US6280659B1 (en) * 1996-03-01 2001-08-28 David W. Sundin Vegetable seed oil insulating fluid
RU2352549C2 (ru) * 2002-04-29 2009-04-20 Дау Глобал Текнолоджиз Инк. Интегрированные химические способы промышленного применения растительных масел из семян
US7576227B2 (en) 2002-04-29 2009-08-18 Union Carbide Chemicals & Plastics Technology Corporation Integrate chemical processes for industrial utilization of seed oils
WO2004065532A1 (de) * 2003-01-22 2004-08-05 Cognis Ip Management Gmbh Geruchsminderung von ölkomponenten durch adsorption mit polymeren adsorbentien
US7459574B2 (en) 2003-01-22 2008-12-02 Cognis Ip Management Gmbh Reducing the odor of oil components by means of adsorption with polymeric adsorbing agents
EP2196523A4 (de) * 2007-10-12 2011-04-20 Nippon Suisan Kaisha Ltd Verfahren zur herstellung von hochreinem kaiserbarsch-öl
US8399694B2 (en) 2007-10-12 2013-03-19 Nippon Suisan Kaisha, Ltd. Process for producing highly purified orange roughy oil
CN101821369B (zh) * 2007-10-12 2014-01-29 日本水产株式会社 高度精制燧鲷油的制造方法
WO2009105351A1 (en) * 2008-02-21 2009-08-27 Dow Global Technologies Inc. Separation of natural oil-derived aldehydes or hydroxy methyl esters using process chromatography
JP2024511558A (ja) * 2021-03-02 2024-03-14 カーギル インコーポレイテッド バイオ原料油誘電性流体を製造するための方法

Also Published As

Publication number Publication date
JPS5984992A (ja) 1984-05-16
EP0108571A3 (de) 1985-03-06
JPH0420037B2 (de) 1992-03-31

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Inventor name: ISHIWATARI, HIDEO

Inventor name: AIZAWA, MASANORI

Inventor name: KOSHIBA, SUZUKO

Inventor name: KORESAWA, TAKESHI