WO2023199790A1 - Composition d'huile/graisse pour friture ainsi que procédé de fabrication de celle-ci, procédé de fabrication d'aliment frit, et procédé conférant une odeur d'hydrogénation à un aliment frit - Google Patents

Composition d'huile/graisse pour friture ainsi que procédé de fabrication de celle-ci, procédé de fabrication d'aliment frit, et procédé conférant une odeur d'hydrogénation à un aliment frit Download PDF

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Publication number
WO2023199790A1
WO2023199790A1 PCT/JP2023/013898 JP2023013898W WO2023199790A1 WO 2023199790 A1 WO2023199790 A1 WO 2023199790A1 JP 2023013898 W JP2023013898 W JP 2023013898W WO 2023199790 A1 WO2023199790 A1 WO 2023199790A1
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WIPO (PCT)
Prior art keywords
oil
fat
frying
nonenal
fat composition
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Application number
PCT/JP2023/013898
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English (en)
Japanese (ja)
Inventor
恵理奈 肥山
瑞貴 山中
真祐 春口
里奈 清水
勇介 原
賀美 井上
Original Assignee
株式会社Ｊ－オイルミルズ
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Publication of WO2023199790A1 publication Critical patent/WO2023199790A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/10—General methods of cooking foods, e.g. by roasting or frying

Definitions

  • Hydrogenated oils are widely used in oil and fat foods such as margarine, shortening, and butter cream, confectionery such as donuts, cakes, and chocolate, and as frying oil for other foods.
  • Hydrogenated oils include vegetable oils and fats such as soybean oil, rapeseed oil, palm oil, coconut oil, and palm kernel oil, or animal fats and oils such as whale oil, fish oil, beef tallow, and pork fat, in a temperature range of about 160°C to about 210°C. It is produced by hydrogenation in the presence of a nickel catalyst or the like at a temperature of . Hydrogenated oils are edible processed oils and fats that are solid at room temperature, are manufactured using inexpensive oil and fat raw materials, and have stable quality, so they are used in large quantities and in a wide range of applications.
  • Hydrogenated oils include extremely hydrogenated oils that are hydrogenated so that unsaturated fatty acids are completely eliminated, and partially hydrogenated oils and fats that are hydrogenated so that some unsaturated fatty acids remain.
  • partially hydrogenated fats and oils have an odor called "hydrogenated odor".
  • Hydrogenated odors tend to be perceived as imparting a sticky, elegant sweetness that is created as a result of food processing such as heating being applied to foods containing hydrogenated oils.
  • the cooked donuts are given a sweet cooking taste, which motivates consumers to purchase them and gives them a sufficient sense of satisfaction when eating them.
  • products using hydrogenated oils such as margarine and fat spreads have a unique richness and sweetness that enhance their flavor.
  • Patent Document 1 describes a hydrogenated oil flavoring agent consisting of (E)-6-octenal.
  • Patent Document 1 only describes that a hydrogenated oil flavor can be imparted to an oil and fat product with reduced hydrogenated oil, and does not mention that a hydrogenated oil flavor can be imparted to an oil and fat product that does not contain hydrogenated oil. This is insufficient.
  • the problem to be solved by the present invention is to provide a frying oil and fat composition that can impart a hydrogenated odor to foods and does not contain partially hydrogenated oil and fat, and a method for producing the frying oil and fat composition. Furthermore, another problem to be solved by the present invention is to provide a method for producing a fried food using the oil composition for frying, and a method for imparting a hydrogenated odor to a fried food using the oil composition for frying. That's true.
  • the present inventors have made repeated studies in view of the above-mentioned problems, and have developed an oil and fat composition for frying that contains cis-6-nonenal and trans-6-nonenal in a specific range of ratios and does not contain partially hydrogenated oil or fat. It was discovered that odor can be imparted.
  • the present invention has been completed based on these findings.
  • the present invention includes cis-6-nonenal and trans-6-nonenal, the content of cis-6-nonenal/the content of trans-6-nonenal is from 0.01 to 50, and partially hydrogenated.
  • This is an oil and fat composition for frying that does not contain any oil or fat.
  • the oil and fat composition for frying of the present invention preferably further contains at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil.
  • the frying oil/fat composition of the present invention preferably contains the oxidized oil, and the peroxide value of the oxidized oil is preferably 15 or more and 350 or less.
  • the oxidized fat is preferably at least one oxidized fat selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
  • the present invention uses cis-6-nonenal and trans-6-nonenal in a base oil such that the content of cis-6-nonenal/the content of trans-6-nonenal is 0.01 or more and 50 or less.
  • This is a method for producing a frying oil/fat composition, which includes a step of adding the oil/fat composition to an edible oil/fat, which does not contain a partially hydrogenated oil/fat.
  • the method for producing an oil and fat composition for frying of the present invention preferably includes a step of adding at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil to the edible oil and fat that is the base oil. Including further.
  • the method for producing an oil or fat composition for frying of the present invention is preferably performed by heat-treating the edible oil or fat, which is a raw material for the oxidized oil, while supplying air to oxidize the edible oil or fat so that the peroxide value becomes 15 or more and 350 or less.
  • the method further includes the step of processing to produce the oxidized fat.
  • the edible fat or oil used as a raw material for the oxidized fat or oil is preferably at least one selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
  • the amount of air supplied in the oxidation treatment is preferably 0.005 L/min or more and 10 L/min or less per 1 kg of the edible fat or oil.
  • the heating temperature in the oxidation treatment is preferably 50°C or more and 220°C or less.
  • the present invention provides cis-6-nonenal and trans-6-nonenal in a base such that the content of cis-6-nonenal/the content of trans-6-nonenal is from 0.01 to 50.
  • the frying oil composition includes a step of producing a frying oil composition by adding it to edible oil, which is oil, and a step of frying the fried seeds using the frying oil composition. This is a method of imparting a hydrogenated odor to fried foods without containing hydrogenated foods.
  • the oil and fat composition for frying of the present invention does not contain partially hydrogenated oil and fat, and can impart a hydrogenated odor to foods.
  • the method for producing a frying oil or fat composition of the present invention can produce a frying oil or fat composition that does not contain partially hydrogenated oil or fat and can impart a hydrogenated odor to foods.
  • fried foods can be produced using the above-mentioned oil and fat composition for frying.
  • hydrogenated odor can be imparted to fried foods using the above-mentioned frying oil/fat composition.
  • the oil and fat composition for frying of the present invention contains cis-6-nonenal and trans-6-nonenal. These are well-known compounds, such as cis-6-nonenal manufactured by Sigma Adrich and trans-6-nonenal manufactured by Sundia MediTech Company. Further, the content of cis-6-nonenal/content of trans-6-nonenal is 0.01 or more and 50 or less.
  • the content is 0.02 or more and 50 or less, 0.03 or more and 50 or less, 0.04 or more and 50 or less, 0.05 or more and 50 or less, 0.06 or more and 50 or less, 0.07 or more and 50 or less, and 0.08 or more. It may be 50 or less, or 0.09 or more and 50 or less.
  • the content is preferably 0.05 or more and 40 or less, more preferably 0.1 or more and 30 or less, even more preferably 0.15 or more and 25 or less, particularly preferably 1.0 or more and 20 or less, and most preferably 2.0. 10 or less. If the content of cis-6-nonenal/the content of trans-6-nonenal is too low or too high, the effect of the oil and fat composition for frying on imparting a hydrogenated odor to foods becomes weak.
  • the content of cis-6-nonenal contained in the oil and fat composition for frying of the present invention is preferably 0.01 ppm or more and 10 ppm or less, more preferably 0.05 ppm or more and 8 ppm or less, and still more preferably 0.1 ppm or more and 5 ppm or less. Particularly preferably 0.15 ppm or more and 3 ppm or less, most preferably 0.2 ppm or more and 1 ppm or less.
  • the content of trans-6-nonenal contained in the frying oil and fat composition of the present invention is preferably 0.005 ppm or more and 10 ppm or less, more preferably 0.01 ppm or more and 5 ppm or less, and even more preferably 0.02 ppm or more and 3 ppm or less. Particularly preferably 0.03 ppm or more and 1 ppm or less, most preferably 0.04 ppm or more and 0.5 ppm or less.
  • the frying oil composition of the present invention can impart a hydrogenated odor to foods with higher efficiency.
  • the total content of cis-6-nonenal and trans-6-nonenal contained in the oil and fat composition for frying of the present invention is preferably 0.1 ppm or more and 20 ppm or less, more preferably 0.2 ppm or more and 10 ppm or less, and even more preferably It is 0.3 ppm or more and 5 ppm or less, particularly preferably 0.4 ppm or more and 2 ppm or less, and most preferably 0.4 ppm or more and 1 ppm or less.
  • the frying oil composition of the present invention can impart a hydrogenated odor to foods with higher efficiency.
  • the frying oil/fat composition of the present invention does not contain partially hydrogenated oil/fat.
  • the partially hydrogenated fat or oil in the present invention means a hydrogenated fat or oil having an iodine value of 4 or more.
  • the frying oil/fat composition of the present invention can impart a hydrogenated odor to foods even if it does not contain partially hydrogenated oil/fat.
  • the oil and fat composition for frying of the present invention preferably further contains at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, and more preferably further contains oxidized oil.
  • Oxidized fats and oils are obtained by oxidizing raw material edible fats and oils.
  • the edible fats and oils used as raw materials for oxidation treatment are not particularly limited as long as they are edible and edible, but include rapeseed oil, soybean oil, palm oil, corn oil, olive oil, sesame oil, linseed oil, perilla oil, Vegetable oils and fats such as safflower oil, sunflower oil, cottonseed oil, rice oil, peanut oil, shea butter, monkey fat, cacao butter, palm kernel oil, coconut oil, grapeseed oil, macadamia nut oil, coconut oil, evening primrose oil; microbial fats and oils Animal fats and oils such as beef tallow, lard, milk fat, chicken oil, and fish oil; Synthetic fats and oils such as medium-chain fatty acid triglycerides; and the like.
  • the edible fats and oils used as raw materials for oxidation treatment include milk fat, arachidonic acid-containing fat, sunflower oil, macadamia nut oil, rapeseed oil, soybean oil, corn oil, grapeseed oil, lard, coconut oil, rice oil, and linseed oil.
  • the oil is at least one type of oil selected from the group consisting of milk fat, arachidonic acid-containing oil, sunflower oil, and macadamia nut oil.
  • the peroxide value of edible oils and fats generally distributed in the market is about 0 to 10, but the peroxide value is increased to about 15 to 350.
  • the range of peroxide value (hereinafter sometimes referred to as "POV") may be in the range of 20 to 300, and may be in the range of 25 to 290. , may be in the range of 40 or more and 270 or less, and may be in the range of 60 or more and 250 or less.
  • the peroxide value can be measured in accordance with "Standard Oil and Fat Analysis Test Method 2.5.2 Peroxide Value" (Japan Oil Chemists' Society).
  • the oils and fats to be subjected to oxidation treatment may be used alone or in combination of two or more types, but when two or more types are used together, the peroxide value of the entire mixed oil after oxidation treatment may be within the above range.
  • two or more types of fats and oils may be oxidized separately and then mixed, as long as the peroxide value of the entire mixed oil obtained by mixing after the oxidation treatment is within the above range.
  • the above milk fat is obtained from raw milk, cow's milk, special milk, etc. and has an oil and fat content of 95% by mass or more and 100% by mass or less.
  • Examples include anhydrous milk fat, clarified butter, and the like.
  • Anhydrous milk fat refers to milk etc. from which almost all components other than milk fat have been removed, and is sometimes expressed as AMF (Anhydrous Milk Fat, butter oil).
  • Clarified butter is butter with the fat content removed.
  • the milk fat used in the present invention is preferably anhydrous milk fat or clarified butter, more preferably anhydrous milk fat. Further, the fat content of the milk fat is preferably 98% by mass or more and 100% by mass or less, more preferably 99% by mass or more and 100% by mass or less.
  • the arachidonic acid-containing fat or oil refers to a fat or oil containing arachidonic acid.
  • arachidonic acid there is no particular restriction on the origin of arachidonic acid, and those obtained from various animals and plants, microorganisms, algae, etc. are commercially available, and those skilled in the art can use these known ones as appropriate, but it is preferably derived from microorganisms.
  • the content of arachidonic acid in the arachidonic acid-containing oil is not particularly limited, but is preferably 5% by mass or more, more preferably 8% by mass or more, and preferably 10% by mass or more. More preferred.
  • the proportion of oleic acid in the total amount of constituent fatty acids is preferably 70% by mass or more and 100% by mass or less, more preferably 75% by mass or more and 95% by mass or less.
  • the content is preferably 80% by mass or more and 90% by mass or less.
  • the content of oleic acid in the total amount of constituent fatty acids shall be measured in accordance with the method described in "Standard Oil and Fat Analysis Test Method 2.5.23-2013 Fatty Acid Composition (Capillary Gas Chromatography Method” (Japan Oil Chemists' Society)) I can do it.
  • oxidized edible oils and fats are compositions made up of an extremely large variety of chemical substances, and it is either impossible to investigate and identify each chemical substance contained, or it may be extremely excessive. This method is not practical because it requires a large amount of financial expenditure and time.
  • the content of at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil contained in the oil and fat composition for frying of the present invention is preferably 1 ppm or more and 30,000 ppm or less, more preferably 100 ppm or more. It is 25,000 ppm or less, more preferably 250 ppm or more and 23,000 ppm or less, particularly preferably 500 ppm or more and 21,000 ppm or less.
  • the oil and fat composition for frying of the present invention can impart a hydrogenated odor to foods with higher efficiency.
  • the frying oil and fat composition of the present invention may appropriately contain auxiliaries that are commonly added to edible foods.
  • auxiliaries include antioxidants, antifoaming agents, emulsifiers, fragrances, flavoring agents, pigments, and physiologically active substances.
  • Specific examples include ascorbic acid fatty acid ester, lignan, coenzyme Q, ⁇ -oryzanol, tocopherol, and silicone.
  • the method for producing the oil and fat composition for frying of the present invention comprises combining cis-6-nonenal and trans-6-nonenal in a ratio of cis-6-nonenal content/trans-6-nonenal content of 0.01 or more. It includes a step of adding it to edible fats and oils that are base oils so that it becomes 50 or less.
  • Examples of the edible fats and oils that are the base oil include rapeseed oil (including high oleic acid type), soybean oil, palm oil, palm kernel oil, corn oil, olive oil, sesame oil, linseed oil, perilla oil, safflower oil, and sunflower oil.
  • vegetable oils such as cottonseed oil, rice oil, peanut oil, coconut oil, shea butter, monkey fat, cacao butter, grapeseed oil, macadamia nut oil, coconut oil, evening primrose oil, beef tallow, pork fat, chicken fat, milk fat, etc.
  • Examples include animal fats and oils, medium chain fatty acid triglycerides, and the like.
  • processed oils and fats such as these fractionated oils (medium melting point part of palm oil, soft fractionated palm oil, hard fractionated palm oil, etc.), transesterified oil, and the like can be mentioned.
  • Edible fats and oils may be used alone or in combination of two or more.
  • the oxidized oil/fat is obtained by oxidizing the edible fat/oil serving as the raw material, as described above.
  • the method for producing an oil or fat composition for frying of the present invention preferably includes heat treatment while supplying air to the edible oil or fat that is the raw material for the oxidized oil or fat, so that the edible oil or fat is oxidized to have a peroxide value of 15 or more and 350 or less.
  • the method further includes a step of producing the oxidized fat.
  • the cumulative amount of heating temperature (°C) x heating time (hours) is: heating temperature (°C) before changing the temperature x heating time (hours) before changing the temperature + It can be calculated as the heating temperature (°C) after changing the temperature x the heating time (hours) after changing the temperature, or the integral value of the heating temperature (°C) over the heating time (hours).
  • oxygen may be supplied by taking in oxygen from the open space of the container by stirring or by blowing oxygen into the container.
  • Air or the like may be used as the oxygen source. This promotes the oxidation of the edible oil and fat used as the raw material.
  • the amount of oxygen supplied is preferably in a range of 0.001 L/min or more and 2 L/min or less per 1 kg of the edible fat or oil.
  • the flow rate is preferably in the range of 0.005 L/min or more and 10 L/min or less, and more preferably 0.01 L/min or more and 5 L/min or less per 1 kg of the fat or oil.
  • the method of imparting a hydrogenated odor to fried foods of the present invention is to combine cis-6-nonenal and trans-6-nonenal with a ratio of cis-6-nonenal content/trans-6-nonenal content of 0. 01 or more and 50 or less to produce a frying oil/fat composition by adding it to an edible oil/fat that is a base oil, and a step of frying the fried seeds using the frying oil/fat composition.
  • partially hydrogenated fats and oils are not used in the fried food, a hydrogenated odor is imparted to the fried food.
  • cis-6-nonenal and trans-6-nonenal are mixed so that the content of cis-6-nonenal/content of trans-6-nonenal is 0.01 or more and 50 or less.
  • the method includes a step of adding to an edible oil or fat that is a base oil to produce an oil or fat composition for frying, and a step of frying fried seeds using the oil or fat composition for frying.
  • Examples of the fried foods include, but are not limited to, donuts, fried bread, curry bread, piroshki, corn dogs, croutons, karinto, fried rice crackers, snacks, fritters, pork cutlets, chicken cutlets, fried chicken, fried chicken, and fried fish. , tempura, croquettes, minced meat cutlets, fries, chicken nuggets, hash browns, fried tofu, instant ramen, etc.
  • Comparative example 5 The donut dough was fried in the same manner as the donut dough using the oil and fat composition consisting only of the base oil. The results are shown in Table 6.
  • Control example 1 The donut dough was fried in the same manner as the donut dough using an oil and fat composition consisting of 60% by mass of the refined palm oil and 40% by mass of hydrogenated rapeseed fat (manufactured by J-Oil Mills Co., Ltd.). The results are shown in Table 6.
  • the donuts fried using the frying fat compositions of Comparative Examples 1 to 4 that do not contain cis-6-nonenal are somewhat similar to the control donuts fried using the frying fat composition of Comparative Example 1.
  • the flavor was not similar to that of the control donut.
  • the donuts fried using the frying fat composition of Comparative Example 5 that did not contain cis-6-nonenal and trans-6-nonenal did not have a flavor similar to the control donut.
  • the donuts fried using the frying oil and fat compositions of Examples 1 to 25 had a flavor very similar to or similar to the control donut.
  • Comparative example 7 The commercially available fried chicken was fried in the same manner as the fried chicken using the oil and fat composition consisting only of the base oil. The results are shown in Table 8.
  • Control example 2 The commercially available fried chicken was fried in the same manner as the fried chicken using an oil and fat composition consisting of 60% by mass of the purified palm oil and 40% by mass of hydrogenated rapeseed fat (manufactured by J-Oil Mills Co., Ltd.). The results are shown in Table 8.
  • Examples 33 to 38 and Comparative Example 8 Refined palm oil (manufactured by J-Oil Mills Co., Ltd.) was used as the base oil, and each component was added to the base oil at a concentration shown in Table 9 to prepare each oil and fat composition for frying. . 30 parts by mass of water was added to 100 parts by mass of a commercially available donut raw material (donut ball mix manufactured by Nihon Shokuken Co., Ltd.) and mixed, and the resulting dough was mixed by hand until it became a moist ball. An appropriate amount of the donut dough was shaped into a round shape and fried with each of the above frying oil and fat compositions at 160° C. for 5 minutes. The results are shown in Table 9.
  • the donuts fried using the frying fat composition of Comparative Example 8 that does not contain trans-6-nonenal are somewhat similar to the control donuts fried using the frying fat compositions of Control Examples 1 and 2. It was flavorful. On the other hand, the donuts fried using the frying oil and fat compositions of Examples 33 to 38 had a flavor very similar to or similar to the control donut.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Edible Oils And Fats (AREA)

Abstract

L'invention fournit notamment une composition d'huile/graisse pour friture qui contient un composé conférant une odeur d'hydrogénation à un aliment frit, et un procédé de fabrication de cette composition d'huile/graisse pour friture.　La composition d'huile/graisse pour friture de l'invention contient un cis-6-nonénal et un trans-6-nonénal, teneur en cis-6-nonénal / teneur en trans-6-nonénal étant supérieur ou égal à ０,０１ et inférieur ou égal à ５０, mais ne contient pas d'huile/graisse partiellement hydrogénée. Le procédé de fabrication de composition d'huile/graisse pour friture de l'invention inclut une étape au cours de laquelle le cis-6-nonénal et le trans-6-nonénal, sont additionnés à une huile/graisse comestible consistant en une huile de base de sorte que teneur en cis-6-nonénal / teneur en trans-6-nonénal est supérieur ou égal à ０,０１ et inférieur ou égal à ５０. Cette composition d'huile/graisse pour friture ne contient pas d'huile/graisse partiellement hydrogénée.
PCT/JP2023/013898 2022-04-13 2023-04-04 Composition d'huile/graisse pour friture ainsi que procédé de fabrication de celle-ci, procédé de fabrication d'aliment frit, et procédé conférant une odeur d'hydrogénation à un aliment frit WO2023199790A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101124979A (zh) * 2007-08-31 2008-02-20 张之涤 天然乳品香料及其制备方法
JP2009089684A (ja) * 2007-10-11 2009-04-30 Nisshin Oillio Group Ltd 低トランス脂肪酸油脂組成物
WO2014167957A1 (fr) * 2013-04-10 2014-10-16 長谷川香料株式会社 Agent permettant de communiquer une flaveur d'huile hydrogénée

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101124979A (zh) * 2007-08-31 2008-02-20 张之涤 天然乳品香料及其制备方法
JP2009089684A (ja) * 2007-10-11 2009-04-30 Nisshin Oillio Group Ltd 低トランス脂肪酸油脂組成物
WO2014167957A1 (fr) * 2013-04-10 2014-10-16 長谷川香料株式会社 Agent permettant de communiquer une flaveur d'huile hydrogénée

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KEPPLER J. G., SCHOLS J. A., FEENSTRA W. H., MEIJBOOM P. W.: "Components of the hardening flavor present in hardened linseed oil and soybean oil", JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, SPRINGER, DE, vol. 42, no. 3, 1 March 1965 (1965-03-01), DE , pages 246 - 249, XP009549401, ISSN: 0003-021X, DOI: 10.1007/BF02541140 *

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