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
  • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
  • C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation

Definitions

• the invention relates to a process for the production of stable ozonized oils from unsaturated vegetable oils with removal of physiologically questionable low molecular weight aldehydes and ketones.
• the process according to the invention provides valuable products which are suitable for therapeutic and cosmetic use in humans and animals.
• reaction of ozone with unsaturated fatty acids produces peroxidic products as therapeutically valuable active substances and low-molecular aldehydes and ketones, especially malondialdehyde, as undesirable by-products.
• the peroxidic products are used, for example, in dermatology for fungal diseases, leg ulcers, poorly healing wounds, infected wounds and the like.
• the ketones and aldehydes formed as by-products are therapeutically ineffective and largely physiologically questionable. The latter is particularly true for malondialdehyde, which occurs in considerable quantities when ozonization of unsaturated vegetable oils is complete (see Registry of Toxic Effects of Chemical Substances, U.S. Department of Health and Human Services, 1984).
• the object of the invention is to provide ozonized products from unsaturated vegetable oils which are therapeutically valuable products, are stable for a long time and have the lowest possible content of low molecular weight aldehydes and ketones, in particular malondialdehyde.
• the invention relates to a process for producing stable ozonized oils from unsaturated vegetable oils by introducing an ozone-oxygen mixture into the oil until saturation, which is characterized in that after the ozonization, an extraction treatment in an acidic environment in the presence of a redox system, preferably a biological redox system which is capable of a moderate radical reaction and which carries out in the presence of an artificial or natural antioxidant or reducing agent.
• a redox system preferably a biological redox system which is capable of a moderate radical reaction and which carries out in the presence of an artificial or natural antioxidant or reducing agent.
• unsaturated vegetable oils are olive oil, safflower oil, wheat germ oil, linseed oil, almond oil, nut oil, sunflower oil, poppy seed oil, sesame oil, castor oil, croton oil, soybean oil and palm oil. Olive and safflower oils are preferred. Olive oil is especially preferred.
• the redox system used which is capable of radical reactions, acts in the organism both as an electron acceptor and as an electron donor.
• Preferred examples of redox systems are ascorbic acid, the essentially membrane-associated redox system vitamin E, vitamin A and the biological quinoid / benzoid systems. Ascorbic acid is particularly preferred.
• a pH of 3.5 to 6.5 has proven to be particularly suitable for carrying out the extraction treatment.
• ascorbic acid or citric acid can be used.
• antioxidants or reducing agents are butylated hydroxyanisole, gallate and hydrogen sulfite.
• the ozone-oxygen mixture is produced in compliance with the regulations for the production or filling of medical oxygen.
• the ozone is generated by a silent electrical discharge (absolutely nitrogen-free to avoid the formation of aggressive and reactive nitrogen oxides, especially radicals).
• the ozonization of the oil is carried out with a continuous pass with a gas flow in the range of 1 to 2 liters per minute.
• the ozone concentration used is preferably in the range from 50 to 70 ⁇ g per ml.
• the oil is bubbled through using a cylindrical vessel with the highest possible “water column” with thermostatting at about 20 ° C.
• a continuous flow is important, especially just before the saturation limit, which becomes apparent when the product solidifies at 20 ° C.
• For 12 liters with a total height of the cylindrical vessel of 60 cm and a diameter of approx. 20 cm, a uniform bubbling time of 180 to 300 hours is required, depending on the ozone concentration of the initial ozone-oxygen mixture.
• aqueous extraction solution For the extraction treatment, about 2 to 20, in particular 3 to 10 and preferably about 5 ml of aqueous extraction solution are used per 1 g of ozonized oil.
• the extraction is preferably carried out by shaking for 10 to 60 minutes. The shaking process can be carried out several times to increase the effectiveness. Any excess sulfite still present in the extract can be removed by shaking out the oily phase with 2% aqueous ascorbic acid solution.
• Particularly preferred combinations for the extraction treatment according to the invention are ascorbic acid + butylated hydroxyanisole, citric acid and butylated hydroxyanisole as well as ascorbic acid and hydrogen sulfite.
• the determination is based on the reaction of malondialdehyde with 2-methylindole in alcoholic-hydrochloric acid solution to form a stable, intensely colored complex.
• Determination of malondialdehyde in ozonized oil About 1 g of the solid oil is weighed exactly and warmed to liquefy under an N2 atmosphere (approx. 30 ° C). Since the oil is immiscible with the reagents, 1 ml of distilled H2O are added in addition to 2 ml of methyl indole and stirred with a magnetic stirrer under the N2 atmosphere during the 20 min reaction time to allow a complete reaction of the malondialdehyde. The alcoholic phase is then measured (after the fat has been removed) in comparison with the calibration series that is applied in parallel each time.
• the product obtained has a peroxide number (POZ) of 929 and a malondialdehyde content of 445 ⁇ g / g of oil.
• the extraction treatment removed 85 percent of the malondialdehyde, while the peroxide number only decreased by 5.7 percent.
• the aqueous extract contains no peroxides, while the malondialdehyde has almost completely passed into the aqueous phase.
• Samples of the ozonated olive oil produced according to Example 1 are subjected to different extraction treatments. For this purpose, 1 g ozonized oil is shaken out with various aqueous solutions for 15 minutes. The POZ and malondialdehyde content are then determined. The results are summarized in the table below.
• x) 1 means that the parameter in question has not been determined
• x) 2 excess sulfite was completely removed by shaking the oil with 10 ml H2O (2 g ascorbic acid / 100 ml), whereby the POZ and malondialdehyde content of the ozonated oil did not change significantly: the peroxide number decreased from 876 to 860, the malondialdehyde content from 68 ⁇ g / g to 52 ⁇ g / g.

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• Chemical & Material Sciences (AREA)
• General 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)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Fats And Perfumes (AREA)
• Cosmetics (AREA)
• Medicinal Preparation (AREA)

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• 1986
  • 1986-03-01 DE DE3606735A patent/DE3606735C2/de not_active Expired - Fee Related
• 1987
  • 1987-01-20 AT AT87100725T patent/ATE42965T1/de not_active IP Right Cessation
  • 1987-01-20 EP EP87100725A patent/EP0235528B1/fr not_active Expired

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