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
  • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
• • 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
  • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
• • 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
  • C11B15/00—Solidifying fatty oils, fats, or waxes by physical processes
• • C—CHEMISTRY; METALLURGY
  • C40—COMBINATORIAL TECHNOLOGY
  • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
  • C40B40/00—Libraries per se, e.g. arrays, mixtures
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
  • Y02E50/00—Technologies for the production of fuel of non-fossil origin
  • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

• the present invention relates to a novel synergistic solid/semi solid organic composition a process for producing such organic composition and a method of solidifying liquid neutral organic compounds using lipid modulators
• the present invention provides a method of solidification, isolation, identification and/or separation of liquid neutral organic compounds and/or mixture of organic molecules or colloids
• the invention encompasses hpid-modulated alteration of the physical properties of vegetable oils, essential oils, mineral oils and organic solvents
• Organic compounds are chemical compounds containing carbon atoms arranged in chains or ⁇ ngs, together with smaller amounts of other elements, mainly hydrogen and oxygen These organic compounds are present either in liquid, solid or gaseous form at ambient temperature These organic compounds may be negatively or positively charged or devoid of charge In other words, it may have a deficiency or excess of electrons on a particular object, giving rise to a positive or negative charge respectively
• Organic compounds can be saturated or unsaturated ones These can be vegetable oils essential oils, mineral oils chemical solvents, etc
• Organic compounds have various phvsical properties such as color, odor, physical state, solubility, melting point, boiling point freezing point etc , and alteration of one or more of such properties are required in order to make them suitable for specific industrial usage or application In other words, modification of physical state of the organic compounds is essential/desirable for their various applications in the industry
• Organic compounds include a group of compounds referred to as fatty acids, fatty alcohols and sterols which were originally found to be constituents of microbial, animal and vegetable fats and fatty oils Alternatively, the fatty acids, fatty alcohols and sterols can also be synthesized chemically The esters of fatty acids are their derivatives with alcohol
• US Patent 5,476,993 discloses a process of reversibly solidifying hydrocarbons for transportation and storage This process involves mixing hydrocarbons like crude oil with a hydrocarbon wax The wax is melted and heated to a temperature above the solidification temperature for the mixture and mixed with the oil
• the disadvantage of this process is that it employs large quantities of wax and is restricted to solidifying only crude oil that later under goes fractional distillation to separate various fractions
• hydrocarbon wax to solidify edible oils, essential oils and organic solvents
• the present invention provides a novel synergistic solid /semi-solid organic composition
• a novel synergistic solid /semi-solid organic composition comprising (a) at least one saturated long chain fatty acid and/or its glycerol esters, or at least one saturated long chain fatty alcohols, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof and (b) one or more liquid neutral organic compounds, said ingredients (a) being present in a ratio between 0.1 to 40 percent by weight and the remaining part from (b); and a process for producing the reversing synergistic solid/semi-solid composition.
• the main object of the invention is to provide a novel, reversible and synergistic solid/semi-solid composition.
• Another object of the invention is to provide a synergistic solid /semi-solid organic composition
• a synergistic solid /semi-solid organic composition comprising (a) at least one saturated long chain fatty acid and/or its glycerol esters, or at least one saturated long chain fatty alcohols, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof and (b) one or more liquid neutral organic compounds.
• One more object of the invention relates to a solidification of uncharged organic liquid by physical method which method is reversible. Yet another object of the invention relates to a process for producing a novel, reversible and synergistic solid/semi-solid composition
• Still another object of the invention is to provide a reversible process for producing a novel, reversible and synergistic solid/semi-solid composition
• Table 1 represents the analysis of fatty acid composition of Triacylglycerols (TAG) obtained from mature kokum (G. indica) seeds at 120 days after flowering
• TAG contained more than 59% of stearic acid (C sub 18 0) and 35 % of oleic acid (C sub 18.1)
• the solid oil from kokum seed was mixed with various neutral liquid organic compounds and the tubes were heated to melt the fat and kept at 4 deg. C after mixing It was observed that the liquid organic compounds were solidified Once the organic is solidified at 4 deg celsius it remains solid at NTP The solidified locate can be reconverted into liquid of identical nature by simple physical process. Therefore, the present solidification process does not involve any chemical reaction.
• the percentage of kokum fat required for such a solidification process is given in Table 2a. Table 2a. Percent Kokum Fat Required for Solidification of Organic Liquids at Four Degrees Celsius
• the lipid catalyst or the solidifying agent was purified from kokum fat using various column chromatographic procedures and C18 reverse phase High Performance Liquid Chromatography. The structure of the purified compound was elucidated
• the purified compounds were identified as saturated fatty acids (stearic and palmitic acids)
• the purified saturated fatty acids were capable of solidifying liquid vegetable oils, essential oils, mineral oil and organic solvents
• free fatty acids were obtained from kokum fat by enzymatic (lipase) hydrolysis and tested for solidifying property
• the free fatty acids from kokum fat showed solidifying activity
• the fatty acids obtained from kokum fat were fractionated into individual fatty acids on C sub 18 reverse phase silica thin layer chromatography. Individual fatty acids were eluted from the thin layer chromatogram plates, used for solidification activity, and found to exhibit the similar property
• the present invention describes a simple and a cost-effective method of altering physical properties of liquid neutral organic compounds by using one or more fatty acids their glycerol esters, fatty alcohols, dicarboxylic acids, sterols and mixtures thereof without involving chemical reactions
• One embodiment of the invention provides a novel synergistic solid/semi-solid organic composition, said composition comprising (a) at least one saturated long chain fatty acid and/or its glycerol ester, or at least one saturated long chain fatty alcohol, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof and (b) a liquid neutral organic compound, said ingredient (a) being present in an amount between 0 1 to 40 percent by weight
• Another embodiment of the invention relates to a process for producing a novel synergistic solid/semi-solid organic composition, said process comprising mixing (a) at least one saturated long chain fatty acid and/or its glycerol ester, or at least one saturated long chain fatty alcohol, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof in an amount between 0.1 to 40 percent by weight with (b) a liquid neutral organic compound It is also possible to perform the process at varying pressures with corresponding modification in respect of other parameters of the process The pressure can vary between 200 torr to 2500 torr.
• Yet another embodiment of the invention relates to a method of solidifying liquid neutral organic compounds or their mixtures, said method comprising adding one or more fatty acids having a chain length of C sub 10 to C sub 31, their glycerol esters or both or at least one saturated long chain fatty alcohol, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof at a concentration of
• the preferred fatty acids employed in the present invention can be selected from decanoic acid, hendecanoic acid, aminohendecanoic acid, dodecanoic acid, aminododecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid docosanoic acid, t ⁇ cosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, t ⁇ acontanoic acid and hent ⁇ acontanoic acid
• the preferred esters of this invention can be selected from t ⁇
• the preferred liquid neutral organic compounds used in the present invention can be selected from vegetable oils such as coconut oil, groundnut oil, olive oil, palm oil, mustard oil, sunflower oil, neem oil, cottonseed oil, rapeseed oil, soybean oil, sesame oil, corn oil, castor oil, safflower oil, rice bran oil, linseed oil, corn oil, poppy oil, fish oil, tall oil and tung oil, essential oils such as mint oil, camphor oil, cinnamon oils, citrus oil, lemon oil, orange oil, Cyprus oil, eucalyptus oil, geranium oil, jasmine oil, lavender oil, lemon grass oil, rose oil, sandalwood oil, turpentine oil, clove oil, pepper oil and cardamom oil mineral oils such as crude fossil oil, petroleum, diesel and kerosene, and neutral organic solvents such as mono-, di- or t ⁇ -hyd ⁇ c alcohols, acetone, acetonit ⁇ le, aniline, benzene butanol, n
• the mixture is gradually allowed to solidify at ambient temperature or allowed to cool and solidify at a temperature in the range of 2 deg. C to 10 deg.C or allowed to cool down at a controlled rate of 0.1 deg. C to 1 deg. C per minute to enhance thermal stability.
• the process comprises taking a required part of the fatty acids or their glycerol esters or at least one saturated long chain fatty alcohol, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof in an appropriate vessel and heating the substance till it melts and adding such molten agent with a required part of the desired liquid neutral organic compound followed by heating the mixture and mixing both the liquids thoroughly.
• the mixture is gradually allowed to solidify at ambient temperature or allowed to cool and solidify at a temperature in the range of 2 deg. C to 10 deg. C or allowed to cool down at a controlled rate of 0.1 deg. C to 1 deg. C per minute to enhance thermal stability.
• the invention describes a novel process of altering the physical properties such as melting and freezing points of edible oils, non edible oils, essential oils, mineral oils and organic solvents in a temperature dependent manner using fatty acids of chain length C sub. 10 to C sub. 31 and/or saturated fatty acids esters of glycerol or both or at least one saturated long chain fatty alcohol, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof.
• fatty acids of chain length C sub. 10 to C sub. 31 and/or saturated fatty acids esters of glycerol or both or at least one saturated long chain fatty alcohol, or at least one dicarboxylic acid, or at least one sterol or mixtures thereof One of the many advantages of this process is that it does not alter the chemical nature of the above mentioned compounds. Using this invention, the conversion of vegetable oils into higher quality vegetable fats in terms of palatability without chemical hydrogenation and the attendant trace metal contamination was achieved.
• essential oils, mineral oils and organic solvents can be solidified at ambient temperatures, which have several industrial applications
• the solidified oils can be used in food and feed, dairy and dairy products, cosmetics, healthcare, paints and dyes, lubricants petrochemical and refining, fuels, organic solvents, waxes, storing and transportation laboratory applications, environmental protection, and several other industries
• Yet another embodiment of the invention relates to a method of solidifying oils using lipids as activators/catalysts which can find application in the manufacture of vegetable butter, margarine, ghee substitute, chocolate preparation, confectioneries, shoe polish, cosmetic lotions, lubricants, etc It relates to a simple and economical method of obtaining solid fat without chemical hydrogenation, having physical properties that are close to those of chemically hydrogenated products Physical properties of the lipid catalyst derived solid fats are analyzed by melting point apparatus with different percentage of lipids and the melting points of the solids so prepared were determined.
• One of the many advantages of the invention is that it provides a substitute process for chemical hydrogenation Hydrogenation is a process of converting unsaturated fatty acids in liquid oils to a saturated form which in turn converts liquid oil into a solid fat useful in margarine preparation and shortening applications
• the hydrogenation is an expensive process, creates undesirable trans-fatty acids, and may contain traces of metal contamination The cost and other factors associated with chemical hydrogenation can be avoided if
• the prepared solidified oils are especially desirable for human consumption.
• Common additives such as stabilizer, flavoring agent, emulsifier, anti-spattering agent, colorant, antioxidant, etc. can be added to the solidified oils of the present invention.
• the applicants observed that when the organic liquid is not neutral then such organic liquid does not solidify by the present method, which establishes that the present invention is restricted to solidification of uncharged liquid/solvents.
• the solid oils are obtained by a simple process of mixing two raw materials and the mixture is then used as such without fractionation.
• the products prepared in this way have physical characteristics, which are advantageous presumably because of the natural rearrangement of the various constituent molecules that were present initially.
• Fatty acids C sub. 10 to C sub. 31
• Fatty acids C sub. 10 to C sub. 31
• Each fatty acid or fatty acid derivative was used separately and in mixture with other fatty acids/derivatives to solidify seed oils, essential oils, mineral oils and organic solvent.
• the minimum quantity (percent, w/w) of solidifying agent required to solidify each class of organic liquid at 25 deg. C was determined.
• the melting temperature of each solidified fatty acid/organic liquid mixture was determined.
• the ability of the agent to solidify organic liquids was enhanced by the presence of an additional hydroxyl group in the middle of the fatty acid chain
• the presence of a hydroxyl group at the ⁇ -carbon (adjacent to carbonyl carbon) in C sub 18 fatty acid was found to adversely affect the ability to solidify seed oils, as compared to stearic acid
• the additional hydroxyl group in the middle of the chain was observed to play a synergistic role
• Dihydroxystea ⁇ c acids with the hydroxyl groups adjacent to each other in 'threo or 'erythro' conformation in the middle of the fatty acid chain also solidified all classes of organic liquids studied, but the same compounds showed decreased solidification ability as compared to stea ⁇ c acid or 12-hydroxystea ⁇ c acid Thus, more than one hydroxyl group in the middle of the fatty acid chain was found to adversely affect the solidification ability
• Fatty acids and their derivatives were mixed in equal ratios by weight and used to solidify organic liquids. It was observed that there was no synergistic effect due to the mixing of the solidifying agents.
• the rate of evaporation of volatile mineral oils and solvents was found to decrease after solidification.
• the rate of evaporation was inversely proportional to the chain length of the fatty acid used for solidification.
• fatty acids it was observed that cholesterol, cholic acid and deoxycholic acid can also solidify seed oil in amounts comparable to long-chain saturated fatty acids
• the mechanism of the present invention may be thought of as a) the fatty acids by virtue of having hydrophobic and a charged hydrophilic components align themselves in a head to tail linear and perhaps perpendicular fashion to create a lattice structure with sufficient spacing for the other liquid neutral organic compounds embedded in the lattice to form a gel to solid structure. b) alternatively, they could also form a large spherical monolayer entrapping the neutral organic compounds in the interior hydrophobic environment thus, leading to the change of liquid to solid physical form.
• Glycerol esters of C sub 12, C sub. 14, C sub 16 and C sub 18 fatty acids (trilaurin, trimyristin, tripalmitin, and tristearin) and hydrogenated vegetable oils were used as solidifying agents to solidify liquid oils.
• the above-mentioned agent was mixed at 20-40 percent of total weight with various quantities of liquid oils selected from the group comprising of edible, non-edible liquid oils, and essential oils The mixture was heated to melt the agent and was allowed to solidify at 4 deg. C. The results are summarized in Table
• Example 3 Various commercially available fatty acids were tested for solidification ability and the results of such experiments are given in the following examples which are provided by way of illustration and not by limitation. Saturated fatty acids from C sub 10 to C sub 31 were tested for their ability to solidify various organic liquids like sunflower oil, lavender oil, diesel, petrol, kerosene and acetone. Fatty acids of varying chain-lengths were mixed with the indicated amounts of oil/solvent. The tubes were heated to melt the saturated fatty acids and were kept at 25 deg C for solidification. The melting temperatures of the solidified mixtures were determined and the results are summarized in Tables 4 and 5
• Nonacosanoic acid 4 46-50 5 59-66 nd nd
• Modified saturated fatty acids from C sub. 6 to C sub. 30 were tested for their ability to solidify various organic liquids like sunflower oil, lavender oil, diesel, petrol, kerosene and acetone.
• the modified fatty acids of various chain-lengths were mixed with the indicated amounts of oil/solvent.
• the tubes were heated to melt the modified saturated fatty acids, mixed thoroughly and kept at 25 deg. C for solidification. The melting temperatures of the solidified mixtures were determined. The results are summarized in Table 6 and 7.
• Table 6 Minimum Percent of Modified Fatty Acid Required for the Solidification of Organic Liquids and Melting Point (MP) of the Solidified Mixture
• 2-hydroxyeicasanoic 8 45-50 10 72-75 10 55-60 ;
• Stearic acid was used as an agent to solidify various organic liquids like solvents, ethanol, methanol, liquid fatty acids, and triolein. Stearic acid was mixed with various amounts of organic liquids and tubes heated to melt the agent. After thorough mixing, the tubes were left at 25 deg. C for solidification. The melting temperatures of the solidified mixtures were determined. The results are summarized in Table 8.
• the mixture of fatty acids, modified fatty acids and fatty alcohols, were used in 1 : 1 ratio for solidification of organic liquids.
• the above-mentioned 1 : 1 mixtures of agents were mixed with the indicated amounts of oil/solvent.
• the tubes were heated to melt the agents and the contents were mixed thoroughly.
• the tubes were then kept at 25 deg. C for solidification.
• the melting temperatures of the solidified mixtures were determined.
• the melting temperature of the solid was determined c) Five grams of stearic acid were taken m a 250-ml beaker and heated to melt the said fatty acid To the melted fatty acid, 95 grams of commercially available geraniol were added and mixed by stirring The mixture was heated up to 70 deg C and the mixture was incubated at 26 to 28 deg C for about 2 hours The solidified product remained solid at ambient temperature The melting temperature of the solid was determined
• the melting temperature of the solid was determined d) Four grams of behenic acid was taken in a 250-ml beaker and heated at 80 deg C to melt the said fatty acid To the melted fatty acid, 95 grams of commercially available acetone was added and mixed by stirring The mixture was heated up to 40 deg C The mixture was cooled and kept at 26 to 28 deg C for about 2 hours The solidified product remained solid at ambient temperature The melting temperature of the solid was determined
• the method of liquefaction of the solid/semi-solid preparations consisted of taking 100 grams of the solid, melting it to the state of liquid. To the melted mixture, 17 grams of sodium hydroxide (17 percent weight/weight aqueous sodium hydride solution) was added and stirred for 10 minutes. After alkali treatment, the mixture was filtered. To the filtrate equal amount of hot water was added, stirred and allowed to settle. The aqueous layer was removed and the process was repeated again. The moisture in the oil was removed under reduced pressure.
• the free fatty acid added in the original preparation was removed by the alkaline treatment as described above. Fifty milliliters of concentrated hydrochloric acid (12 N) was added until the pH became acidic and the free fatty acid was separated by filtration. Alternatively, the added fatty acids or their glycerol esters were recovered by fractional distillation.
• the method of liquefaction of the solid/semi-sohd preparations consisted of taking 100 grams of the solidified mixture, melting it to the state of liquid To the melted mixture 17 grams of sodium hydroxide (17 percent weight/weight aqueous sodium hydroxide solution) was added and stirred for 10 minutes After alkali treatment, the mixture was filtered to remove the salts of fatty acids The filtrate (starting commodity) was recovered
• the solidified oil or solidified organic solvent was melted to liquefy the solid

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