Intromolecular compounds of fatty acid triglycerides

FIELD: chemistry.

SUBSTANCE: invention relates to a product used in chocolate, margarine or shortening, obtained by melting a mixture of components (a) and (b), where component (a) contains triglyceride of disaturated medium-chain fatty acids and monosaturated long-chain fatty acid and (b) contains triglyceride of 1,3-disaturated long-chain fattya cids and 2-monosaturated long-chain fatty acid, wherein the bond length determined through X-ray diffraction, measured in the product is equal to greater than 65 Å, where the medium-chain fatty acid(s) contain(s) 6-12 carbon atoms, and the long-chain fatty acid(s) contain(s) 14-24 carbon atoms.

EFFECT: owing to formation of intramolecular compounds, fats and oil contain a larger amount of symmetrical triglycerides such as cocoa oil, and contain medium-chain fatty acids which do not form separate crystals and can endow the product with a smooth texture and prevent turbidity.

8 cl, 9 dwg, 17 tbl, 6 ex

 

The technical field to which the invention relates

The present invention relates to an intramolecular connections, at least two types of triglycerides of fatty acids having different molecular structure, and containing their food. Intramolecular connections are also referred to as crystalline compounds.

The prior art prior to the invention of

There are usually two types of triglycerides of fatty acids having different molecular structures that can form intramolecular bonds, and properties of the thus obtained intramolecular connections, often used methods of using such triglycerides, applying them in obtaining food such as chocolate, margarine and shortening (non-patent literature 1 and 2, patent literature 1-15). However, all these technologies relate to the intramolecular connections that receive a combination of triglycerides related to the type of St-U-St, and triglycerides related to the type of U-St U (ST: saturated fatty acid, U: unsaturated fatty acids).

On the other hand, it is known that the combination of triglyceride related to the type of St-U-St, and triglycerides related to the type St-St-St (ST: saturated fatty acid, U: unsaturated fatty acids), such as the triglyceride type pop (redial the Metin) (1,3-dipalmitoyl-2-reorgnization) and triglyceride type PPP (tripalmitin) (non-patent literature 2); and cocoa butter and substitute cocoa butter (CBS, solid-lauric fat and fatty oil) cannot form intramolecular connections and have no compatibility, and, in addition, each triglyceride independently crystallized with the formation of eutectic crystals.

Namely, to date, the combination of triglyceride related to the type of St-U-St, and triglycerides related to the type St-St-St (ST: saturated fatty acid, U: unsaturated fatty acids), are not capable of forming intramolecular connections, and therefore can not be obtained from foods containing these intramolecular compounds derived from these two types of triglycerides of fatty acids having different molecular structures, using their properties.

In addition, in recent years, frequent changes of the type(s) fatty acids, comprising the triglyceride, or changed their position to change the properties of fats and oils, i.e. triglycerides. For example, in patent literature 16 describes that triglyceride 1,3-di(S)-2-mono(X) type (SXS), where saturated fatty acid(s) (X)having 12 or less carbon atoms connected in the second position and saturated fatty acid(s) (S), having 16 or more carbon atoms connected by the first and third positions, is used as an agent to prevent pomutneniya, this triglyceride is produced by interesterification reaction using 1,3-specific lipase. Also, patent literature 17 describes what triglycerides, where one of the members of the fatty acid is a saturated fatty acid with 12 or less carbon atoms, and the remaining two fatty acids are saturated fatty acids with 16 or more carbon atoms, obtained by transesterification of natural fats and oils; and they are used as an agent for preventing carlivati, cocoa butter, palm oil, etc.

In addition, in patent literature 18 describes the triglyceride composition containing: triglyceride 1,3-di(S)-2-mono(X) type (SXS), where Caprylic acid (X), associated in the second position, and palmitic acid, or stearic acid (S)associated with the first and third positions; and triglyceride 1-mono(X)di(S) type (SSX), where Caprylic acid (X), related in the first or third positions, and palmitic acid, or stearic acid (S)connected across the second and third positions, or the first and second positions, are used as agents for preventing clouding of fat and dispersed in chocolate.

Also, in patent literature 19 describes how to obtain the symmetric triglycerides, which in the first and third positions are what I medium chain fatty acids, in sn, the second position is a long-chain fatty acid, and usefulness (use) thus obtained symmetric triglycerides, which in sn, the first and third positions are octanoic acid, and sn-second position is stearic acid, as substitutes for butter in chocolate.

Despite the above documents describing the receipt of intra-molecular compounds and their properties the following is a complete list of documents.

[Non-patent literature 1] Journal of Oleo Science, Vol. 42, No. 3, P 184 (1993)

[Non-patent literature 2] Journal of the Japanese Society for Synchrotron Radiation Research (hosyako), Vol. 11, No. 3, P 208 (1998)

[Patent literature 1] Japanese Patent No. 3464646

[Patent literature 2] Japanese Patent Unexamined Publication No. 2002-69484

[Patent literature 3] Japanese Patent Unexamined Publication No. 2003-213291

[Patent literature 4] Japanese Patent Unexamined Publication No. 2002-121584

[Patent literature 5] Japanese Patent Unexamined Publication No. 2004-285193

[Patent literature 6] Japanese Unexamined Patent Publication No. 2003-304807

[Patent literature 7] Japanese Unexamined Patent Publication No. 2003-213289

[Patent literature 8] Japanese Unexamined Patent Publication No. 2004-89006

[Patent literature 9] Japanese Unexamined Patent Publication No. 2004-305048

[Patent literature 10] Japanese Patent Unexamined Publication No. 2003-213287

[Patent literature 11] Japanese Patent Unexamined Publication No. 2003-210107

[Patent literature 12] Japanese Patent Unexamned Publication No. 2003-169601

[Patent literature 13] Japanese Patent Unexamined Publication No. 2003-169600

[Patent literature 14] Japanese Patent Unexamined Publication No. 2003-284491

[Patent literature 15] Japanese Patent Unexamined Publication No. Hei 4-135453

[Patent literature 16] Japanese Patent Unexamined Publication No. Hei 4-75593

[Patent literature 17] Japanese Patent Unexamined Publication No. Hei 5-311190

[Patent literature 18] Japanese Patent No. 3146589

[Patent literature 19] WO 2005/5586

Description of the invention

The object of the present invention are molecular compounds of triglycerides of fatty acids.

Another object of the present invention are foods containing intramolecular connections.

The present invention is made on the basis of the determination using rentgenodiffraction previously unknown intramolecular bond lengths compounds obtained by melting a mixture of two types of triglycerides of fatty acids having a specific structure.

The present invention relates to intra-molecular compound (a) triglyceride dynamising medium chain fatty acids and long-chain monounsaturated fatty acids and (b) triglyceride 1,3-dynamising long-chain fatty acids and 2-monounsaturated long-chain fatty acids, the length of the ties which valued rentgenodiffraction amounted to 65 Å or more.

Brief description of drawings

what a figure 1 shows the diffraction pattern of rentgenodiffraction intermolecular compound I-T of the present invention.

Figure 2 shows the diffraction pattern of rentgenodiffraction intermolecular compound I-N according to the present invention.

Figure 3 shows the diffraction pattern of rentgenodiffraction intermolecular compound I-S of the present invention.

Figure 4 shows the diffraction pattern of rentgenodiffraction intermolecular compound II of the present invention.

Figure 5 shows the diffraction pattern of rentgenodiffraction intermolecular compound III according to the present invention.

Figure 6 shows the diffraction pattern of rentgenodiffraction intramolecular connections IV of the present invention.

7 shows the diffraction pattern of rentgenodiffraction product 1 of the present invention.

On Fig shows the diffractogram of rentgenodiffraction product 2 of the present invention.

Figure 9 shows the diffraction pattern of rentgenodiffraction product 3 according to the present invention.

Preferred variants of the embodiment of the present invention

Triglycerides dynamising medium chain fatty acids and long-chain monounsaturated fatty acids used as component (a) of the present invention, preferably have a medium chain fatty acid with 6 to 12 carbon atoms, more preferably from 6-10 carbon atoms and most preferably 8-10 carbon atoms. In particular, predpochtitelnye are octanoic acid and cekanova acid. In addition, these long-chain fatty acids are preferred acids 14-24 carbon atoms and more preferably 16-22 carbon atoms. In particular, preferred are long chain fatty acids with 16-18 carbon atoms, and they include palmitic acid and stearic acid. These fatty acids may have a non-branched chain or branched chain, preferred are acid with unbranched chain.

Preferred triglycerides dynamising medium chain fatty acids and long-chain monounsaturated fatty acids used as component (a) according to the present invention are 1,3-dynastyseries medium chain fatty acids and 2-monounsaturated long-chain fatty acid.

Two medium chain fatty acid triglycerides are dynamising medium chain fatty acids and long-chain monounsaturated fatty acids used as component (a)may be the same or different, but preferably they are the same.

Triglycerides dynamising medium chain fatty acids and long-chain monounsaturated fatty acids used as component (a) of the present invention, preferably are 8S8 triglycerides, in which the first and third the rd position presents octane acid, and a second position represented by stearic acid; 88S triglycerides, in which the first and second position presents octane acid, and the third position is represented by stearic acid; and S88 triglycerides, in which the first position is represented by stearic acid, and the second and third position presents octane acid.

Triglycerides dynamising medium chain fatty acids and long-chain monounsaturated fatty acids used as component (a) of the present invention, can be easily obtained, for example, by transesterification of natural fats and oils, in particular by transesterification with lipase. Including symmetric triglycerides, in which the first and third positions of the presented medium chain fatty acids and sn-second position presents long-chain fatty acid, preferably obtained by the method described in WO2005/5586. More specifically, the method preferably includes the stage random interesterification of triglycerides of medium chain fatty acids and triglycerides of long chain fatty acids by enzymes or chemical catalyst in the first reaction with obtaining the reaction products containing triglycerides having medium chain fatty acids and long-chain fatty acids as constituent fatty acids; peret is eficacia reaction products and monoether alcohol, medium chain fatty acids in the sn-1-m, 3rd provisions of specific enzymes in the second reaction; and removing (part or all) of monoamino alcohol, medium chain fatty acids and long-chain fatty acids from the reaction of a substance, the resulting second reaction with obtaining symmetrical triglycerides, in which the first and third positions of the presented medium chain fatty acids and sn-second position presents long-chain fatty acid.

Triglyceride 1,3-dynamising long-chain fatty acids and 2-monounsaturated long-chain fatty acids used as component (b) according to the present invention, preferably have a long-chain fatty acids 14-24 carbon atoms and more preferably 16-22 carbon atoms. In particular, preferred are long chain fatty acids with 16-18 carbon atoms, including palmitic acid and stearic acid. These unsaturated fatty acids may be a component (b), including those that have one or more double bond in the molecules, and preferred are those which have one double bond in the molecules. Namely, preferred is oleic acid, linoleic acid and linolenic acid, the most preferred is oleic acid. These fatty acids may have a non-branched chain or osvetleniyu chain, preferred are acid with unbranched chain.

Triglyceride 1,3-dynamising long-chain fatty acids and 2-monounsaturated long-chain fatty acids used as component (b) according to the present invention, preferably are POP triglycerides, in which the first and third position presents palmitic acid, and a second position represented by oleic acid (1,3-dipalmitoyl-2-oleoyl glycerin); triglycerides POS, in which the first and third position presents palmitic acid and stearic acid, and a second position represented by oleic acid (2-oleoyl, which stearoyl glycerin); and SOS triglycerides, in which the first and third position presents stearic acid, and a second position represented by oleic acid (1,3-distearoyl-2-oleoyl glycerol).

As triglyceride 1,3-dynamising long-chain fatty acids and 2-monounsaturated long-chain fatty acids used as component (b) according to the present invention can be used, for example, one of the naturally occurring components, such as cocoa butter, butter salavage tree, Shea butter, walnut oil, bassia, oil from mango seeds, oil kokum, stearin from cotton seeds, palm oil or fractions of these oils. With matrichnye triglycerides can be obtained by lipase (see reference Japanese Patent Unexamined Publication No. Sho 55-71797 or Japanese Unexamined Patent Publication No. Sho 62-155048 as examples).

In particular, preferred are the fats and oils containing a large number of symmetric triglycerides, such as POP, POS and SOS, and preferred are cocoa butter, stearin salavage tree, Shea stearin, oil nut bassia, oil from mango seeds, oil kokum and palm oil average fraction (PMF). In the case of the use of these fats and oils total triglyceride content-type POP (1,3-dipalmitoyl-2-oleoyl glycerin), triglyceride type POS (2-oleoyl, which stearoyl glycerol and triglyceride type SOS (1,3-distearoyl-2-oleoyl glycerin) is preferably 70 wt.% or more and most preferably 80 wt.% or more.

Intramolecular compounds of the present invention can be obtained by melting mixtures of triglycerides (a) and (b) by heating them up to 50 to 60°C. When mixing the components of triglycerides (a) and (b) may be used an organic solvent(s). In this case, the mass ratio of component (a)/component (b) is preferably from 5/95 to 95/5 by weight, more preferably from 20/80 to 80/20 by weight and most preferably from 30/70 to 70/30 by weight. On the other hand, the molar ratio of component (a)/component (b) is preferably about 1/1.

Preferred organic solvents include ketones, such as acetone and methylethyl ketone; hydrocarbons such as hexane and petroleum ether; aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol and propanol; hydrosport; and such ethers as simple diethyl ether; esters like ethyl acetate. Acceptable any organic solvents, if they dissolve the triglyceride to the point of boiling or below, and point their melting point is below the freezing temperature. Preferred are acetone, hexane, alcohols and hydrosport, and most preferred is acetone.

The intramolecular bond length of the compounds of the present invention can be calculated by setting d (Å, interplanar distance), the peak corresponds to the distance from the Miller index (001), which is observed at about 2θ=from 0 to 10° when using rentgenodiffraction (wavelength x-ray beam: λ=1,5405 Å). Intramolecular compounds of the present invention preferably have a bond length of 70 Å or more, more preferably from 70 to 85 Å and most preferably from 74 to 82 Å. For comparison, 100% cocoa butter, the peak of the (002) reflection, the connection 64 Å, observed at about 2θ=2,8°, which on the surface of it (004) is observed at about 2θ=5,5°.

Intramolecular connection is about this connection can be used as components of food, such as fat and fatty oil. For example, they can be used as a fat or fatty oil as a component of chocolate, margarine, shortening and other Specific applications of margarine or shortening include the application of them to the test, when obvalivaniem, cream, filling for sandwiches, coating, spraying, frying, but are not limited to these. Used herein, the term "chocolate"is contained in the description of the present invention includes all kinds of chocolate, and fat, and fatty oils, food products, processed but not limited to those listed in the description.

According to the present invention as it relates to the intramolecular connections fats and oils that have not been known until now. These molecular compounds can be applied as part of the fats and oils that are included in the food composition. Due to the formation of intramolecular connections fats and oils contain a large number of symmetric triglycerides, such as cocoa butter and those that contain medium chain fatty acids that do not form separate crystals, and, in addition, can provide the product with a smooth texture and to prevent clouding.

These molecular compounds can be applied as part of the fats and oils that is W ill result in the composition of margarine or shortening. Due to the formation of intramolecular connections it is possible to prevent the gradual curing, and, in addition, has the advantage that in the absence of repeated deposition of crystals and the absence of the need of conservation.

The following additional Examples illustrate the present invention.

EXAMPLES

Example obtain 1 (Obtaining powdery lipase)

Low molecular weight components were separated using a UV device (SIP-0013, produced by Asahi Kasei Corporation) from the liquid lipase derived from Rhizomucor miehei, produced by Novozymes Japan Ltd. (brand: Palatase20000L), where the lipase is dissolved and dispersed in an aqueous solution to obtain an aqueous solution 1 containing a lipase (with a concentration of dry matter of 20.1 wt.%). More specifically, conduct UV filtering liquid lipase (Palatase20000L) while cooling on ice to the concentration of 1/2 volume and put the same number of 0,01M buffer phosphoric acid, pH 7. The same operations UV filter and the introduction of buffer phosphoric acid was carried out twice with obtaining a solution. Then there was an additional UV filtration of the solution and the thus obtained concentrated solution of lipase was seen as an aqueous solution 1 containing a lipase.

20 ml of milk (Koiwai Milk Oishisa-shitate produced Koiwai Dairy Products Co., Ltd: concentration of dry substances is to 12.9 wt.%) were introduced in a 20 ml aqueous solution of 1, containing a lipase. the pH of the thus obtained solution adjust to pH 6.8 to 6.9 aqueous solution of sodium hydroxide.

The volume ratio of concentrated solution of lipase (= aqueous solution 1 containing a lipase): milk was 1:1, and the solids content of the milk made 0.64-fold excess solids content in the aqueous solution 1 containing a lipase.

The solution was dried using spray drying in a spray dryer (SD-1000, produced by Tokyo Rikakikai Co., Ltd.) under the conditions of: inlet temperature 130°C, airflow from 0.7 to 1.1 m3/min and pressure of spray drying from 11 to 12 kPa to obtain a powdery lipase. The particles of the powdered lipase had a spherical shape, 90 wt.% or more powdered lipase had a diameter of 1 to 100 μm, and average particle diameter of 7.6 μm. The diameter of the particles was measured using the size distribution analyzer (LA-500) HORIBA, Ltd.

The concentration of solids in an aqueous solution containing a lipase, and dry matter of milk was measured by the following method.

Concentrations were measured as % Brix using analyzer sugar (BRX-242 produced C.I.S. Corporation).

Example obtain 2 (Getting MLCT A (8S8))

5 g of lipase QLM (Meito Sangyo Co., Ltd.) introduced 700 g of sunflower oil with you who akim oleic acid content (trade mark Olein-Rich, produced by Showa Sangyo Co., Ltd.) and 300 g tricaprylin (brand Tricaprylin, produced by Sigma Aldrich Japan) in 2000 ml reaction vessel. Then reaction was performed under continuous stirring the mixture with a stirrer at 50°C for 2 hours. The remaining enzymes were removed by filtration to obtain 980 g of the reaction products.

4900 g of ethyl ester octanoic acid (brand name Octanoic Acid Ethyl produced Inoue Perfumery Co., Ltd.) and 120 g of powdered enzyme obtained in example 1, 980 g of the reaction product was introduced into a 10 l reaction vessel. Then the enzymatic reaction was performed under continuous stirring by a stirrer at 40°C for 26 hours with obtaining 5600 g of the reaction products. Upon completion of the reaction, ethyl ester octanoic acid, ethyl ester oleic acid and tricaprylin was removed from the reaction products using molecular distillation apparatus of the centrifugal type (produced by NIPPON SHARYO, LTD.) obtaining 300 g of a substance containing triglyceride.

300 grams of a substance containing triglyceride, was placed in the reactor for the reaction it was administered 900 mg of Nickel catalyst and applied hydrogen pressure of 0.3 MPa. Then the substance was heated to 180° C and was stirred for 5 hours. After hydrogenation under pressure in the catalyst was removed by obtaining 300 g triacylglycerol is s, containing medium chain and long-chain fatty acids (MLCT) A (8S8).

Example for the preparation of 3 (Getting MLCT B (10S10))

5 g of 1,3-didecanoyl-2-linoleyl glycerin (produced by Osaka Synthetic Chemical Laboratories, Inc.) was dissolved in 100 ml of ethanol. 2.5 g of 10% charcoal coated with palladium (Wako Pure Chemical Industries, Ltd.) was introduced there and carried out the reaction in an atmosphere of hydrogen at 40°C for 3 hours. After filtration to remove coal coated with palladium and ethanol were obtained 3.5 g MLCT Century

Example 4 (Getting MLCT (88S))

230 g of oleic acid (brand: EXTRA OS-85, produced by NOF Corporation) and 69 g of powdered enzyme obtained in example 1, was introduced in 2070 g tricaprylin (brand: Tricaprylin, produced by Sigma Aldrich Japan) in 5000 ml reaction vessel. Then the enzymatic reaction was performed under continuous stirring the mixture with a stirrer at 40°C for 136 hours. The remaining enzymes were removed by filtration to obtain 2250 g of the reaction products. Upon completion of the reaction, octanoic acid, oleic acid, tricaprylin was removed from the reaction products using molecular distillation apparatus of the centrifugal type (produced by NIPPON SHARYO, LTD.) to obtain 270 g of a substance containing triglyceride.

270 grams of a substance containing triglyceride, was placed in the reactor for the reaction in not what about the introduced 810 mg of the Nickel catalyst and applied hydrogen pressure of 0.3 MPa. Then the substance was heated to 180° C and was stirred for 5 hours. After hydrogenation under pressure in the catalyst was removed to obtain 270 g MLCT (88S).

Example obtain 5 (Getting MLCT D (mixture 88S/8S8))

5 g of lipase QLM (Meito Sangyo Co., Ltd.) introduced 400 g of sunflower oil with high oleic acid content (trade mark Olein-Rich, produced by Showa Sangyo Co., Ltd.) and 600 g tricaprylin (brand: Tricaprylin, produced by Sigma Aldrich Japan) in 2000 ml reaction vessel. Then reaction was performed under continuous stirring the mixture with a stirrer at 40°C for 2 hours. The remaining enzymes were removed by filtration to obtain 980 g of the reaction products.

After the reactions were received 400 g of distilled component of the reacted oil using molecular distillation apparatus of the centrifugal type (produced by NIPPON SHARYO, LTD.) at a temperature of 240°C and a pressure of 1 PA.

400 g of the thus obtained compounds containing triglyceride, was placed in the reactor for the reaction it was administered 1200 mg of Nickel catalyst and applied hydrogen pressure of 0.3 MPa. Then the substance was heated to 180° C and was stirred for 5 hours. After hydrogenation under pressure in the catalyst was removed to obtain 400 g of MLCT D (mixture 88S/8S8).

In Tables 1 and 2 shows the results from the ATA analysis GLC triglyceride compositions MLCT, obtained in the examples get 2-5. The ratio of positional isomers: (88S+S88)/8S8 was determined on the basis of the fact that the ratio of positional isomers of compounds containing triglyceride did not change when hydrobromide during the analysis of the distilled component before hydrobromide or HPLC (Ag ion column). The MLCT ratio B containing dekanovu acid as a main component, defined as follows.

Table 1
Composition (wt.%)888R+R+R88S+S888S88SS+SS8+S8S
MLCT A00,23,6for 95.30,9
MLCT C6,02,985,32,23,6
MLCT D0,8the 3.860,232,42,8

Table 2
Composition (wt.%)1010S+S101010S10More
MLCT2,9for 95.21,8

In Tables 888 indicates that the first, second and third position of the glycerol esters represented by octanoic acid; R indicates that the sn-1 and sn-2 positions of glycerol presents esters of octanoic acid and sn-3 position of the glycerol ether represented by palmitic acid; and 10S10 indicates that the sn-1 and sn-3 positions of the glycerol esters represented by decanoas acid and sn-2 position of the glycerol ether represented by stearic acid.

Example 1 (Getting intermolecular compound I of the MLCT A (8S8) and cocoa butter)

MLCT AND (8S8) and cocoa butter (brand: D Cocoa Butter, produced by Daito Sasao Co., Ltd.) were mixed in a mass ratio of 39.5:60,5, kept at 50°C for 30 minutes and kept at a temperature of 33°C for 30 minutes. Then the mixture was stirred at 5°C for 2 hours and was temperarolly her with getting intermolecular compound I-T, with a bond length of 75 Å. Similarly, MLCT and A cocoa butter) and mass ratio of 39.5:60,5, kept at a temperature of 50°C for 30 minutes and kept at 5°C for 2 hours to obtain intermolecular compound I-N, with a bond length of 75 Å.

MLCT A, cocoa butter and acetone were mixed in a mass ratio of 39.5:60,5:500, overheated up to 50°C To produce acetone solution. Then the solution was cooled on ice, precipitated crystals were filtered and dried to obtain intermolecular compound I-S, with a bond length of 75 Å.

Example 2 (Getting intramolecular connections II of the MLCT B (10S10) and cocoa butter)

MLCT (10S10) and cocoa butter (brand: D Cocoa Butter, produced by Daito Sasao Co., Ltd.) were mixed in a mass ratio 41,2:58,5, kept at 50°C for 30 minutes and kept at 5°C for 2 hours to obtain intermolecular compound (II), bond length 77 Å.

Example 3 (Getting intermolecular compound III of the MLCT C (88S) and cocoa butter)

MLCT (88S) and cocoa butter (brand: D Cocoa Butter, produced by Daito Sasao Co., Ltd.) were mixed in a mass ratio of 42.6:57,4, kept at 50°C for 30 minutes and kept at 5°C for 2 hours to obtain intermolecular compound III with a bond length of 75 Å.

Example 4 (Getting intramolecular connections IV of the MLCT D (88S/8S8) and cocoa butter)

MLCT D (88/8S8) and cocoa butter (brand: D Cocoa Butter, produced by Daito Sasao Co., Ltd.) were mixed in a mass ratio of 41.0:59,0, kept at 50°C for 30 minutes and kept at 5°C for 2 hours to obtain intermolecular compound IV with a bond length of 75 Å.

Table 3 shows the results of GLC analysis triglyceride compositions (wt.%), used cocoa butter (brand: D Cocoa Butter, produced by Daito Sasao Co., Ltd.).

Table 3
Composition (wt.%)POPPOSSOSOther
Cocoa butter16,7a 38.526,018,8

In intramolecular junctions I-T, I-N, I-S and II-IV obtained in Examples 1-4, the formation of intra-molecular compounds is confirmed by rentgenodiffraction. Measurement conditions are listed as following.

Device for measuring: RINT 2100 Ultima +, produced by Rigaku Corporation X-ray: Cu K - α 1 40 kV/40 mA λ=1,5405.

The goniometer: Ultima+ Horizontal Goniometer Type I.

Figure 1-6 shows the results of rentgenodiffraction (pattern) intramolecular compounds I-T, I-N, I-S and II-IV obtained in Examples 1-4, the Tables 4-9 shows the data of their measurements.

Table 4
(Intramolecular connection I-T)
2θ (°)The metric d (Å)Strength (cps)
2,38037,08993714
3,52025,0800331
5,84015,1209595
6,98012,653617
7,76011,383421
8,18010,799824
10,5208,402341
12,9006,856925
16,4605,3810107
16,8605,254358
19,304,5952559
20,9604,234825
22,3403,976266
22,9003,880396
23,903,7201169
24,8403,581433
26,8803,314120
27,1203,285323
28,0803,175117
29,7403,001651

You can see that the peak corresponds to the (002) reflection parameter bond length 75 Å at 2θ=2,380°, the peak corresponds to the (003) reflection at 2θ=3,520°, the peak corresponds to the (005) reflection at 2θ=5,840°, and the peak corresponds to the (006) reflection at 2θ=2,380°.

td align="center"> Strength (cps)
Table 5
(Intramolecular connection I-N)
2θ (°)The metric d (Å)
2,50035,30991965
3,64024,2534325
5,92014,9167702
7,06012,510421
of 834010,593017
10,5808,354762
13,0006,804434
16,5405,355276
17,6205,029315
19,4004,5717259
20,8604,254920
21,2204,183518
21,9004,055132
22,240 3,993951
22,9203,876966
23,0603,853763
24,0603,6957120
24,9603,564536
27,0003,299627
28,0203,181815

You can see that the peak corresponds to the (002) reflection of the setting linkage 74 Å at 2θ=2,500°, the peak corresponds to the (003) reflection at 2θ=3,640°, the peak corresponds to s (005) reflection at 2θ=5,920°, the peak corresponds to the (006) reflection at 2θ=7,060°, the peak corresponds to the (007) reflection at 2θ=of 8340°, and the peak corresponds to the (009) reflection at 2θ=10,580°.

Table 6
(Intramolecular connection I-S)
2θ (°)The metric d (Å)Strength (cps)
2,26039,05901967
3,42025,8131147
5,72015,4378260
10,5408,386416
16,4205,3941122
16,7605,285456
17,9804,929429
19,2604,6046631
19,9204,453536
22,1804,004645
22,5403,941457
22,7603,903874
23,3203,811351
23,7603,7417129

You can see that the peak corresponds to the (002) reflection of the setting linkage 77 Å at 2θ=2,60°, the peak corresponds to the (003) reflection at 2θ=3,420°, and the peak corresponds to the (005) reflection at 2θ=5,720°.

When comparing intermolecular compound I-T compounds with intramolecular I-N and I-S their pattern was similar, with the parameter d is varied, in addition, it appears that they are similar/similar.

Table 7
(Intramolecular connection II)
2θ (°)The metric d (Å)Strength (cps)
2,30038,3798476
3,44025,663142
5,66015,601370
6,70013,181840
BYR 7,78011,354217
8,24010,721318
10,1408,716317
12,3407,1668 25
16,5605,3810136
16,8605,2543130
17,4205,086622
18,2004,220327
19,3204,5904824
19,9604,444751
20,6604,295617
22,2403,9939127
23,2203,8275179
23,9803,7079335
24,7203,598534
24,9803,561753
27,2203,273416

You can see that the peak corresponds to the (002) reflects the Yu parameter linkage 77 Å at 2θ=2,300°, the peak corresponds to the (003) reflection at 2θ=3,440°, the peak corresponds to s (005) reflection at 2θ=5,660°, and the peak corresponds to the (006) reflection at 2θ=6,700°.

Table 8
(Intramolecular compound III)
2θ (°)The metric d (Å)Strength (cps)
2,34037,72391262
3,50025,223396
3,96022,294338
5,74015,3841188
10,1608,699219
10,4208,482721
14,5206,095316
15,2605,801415
16,9205,235833
17,280 5,127526
17,8204,973323
20,4604,3372278
21,6004,1108132
23,0203,860335
23,6803,7542289
25,7403,458236
26,5603,353321
28,1203,170717

You can see that the peak corresponds to the (002) reflection parameter bond length 75 Å at 2θ=2,340°, the peak corresponds to the (003) reflection at 2θ=3,500°, and the peak corresponds to the (005) reflection at 2θ=5,740°.

Table 9
(Intramolecular compound IV)
2θ (°)The metric d (Å)Strength (cps)
2,38037,099 1401
3,58024,659867
5,84015,1209150
10,5408,386425
16,5205,361651
19,4404,5624211
20,4204,3456141
20,6004,3080160
21,3604,156421
21,6404,103331
22,9803,866936
23,6803,7542179
25,0403,553318
25,7603,545630

You can see that the peak with the corresponds to (002) reflection parameter bond length 75 Å at 2θ=2,380°, the peak corresponds to the (003) reflection at 2θ=3,580°, and the peak corresponds to the (005) reflection at 2θ=5,840°.

Table 10 shows the parameters of the bond lengths of the two fats and oils, forming intra-molecular compounds, such as cocoa butter and MLCT. The peaks indicate the parameters bond lengths fats and oils, which were not visible when rentgenodiffraction above intramolecular connections, and, in addition, shows the formation of intramolecular connections.

Table 10
Cocoa butter and MLCT
Fats and oilsParameter bond length (Å)The structure of the circuit
Cocoa butter IV452CL
V633CL
MLCT A463CL
MLCT B453CL
MLCT C483CL

Example 5 (production of chocolate containing intramolecular compounds of the present invention).

Chocolate n who were given according to the recipe, in Table 11. Conducted thermoregulation as control, and product 1-T and then they were moulded and cooled for 30 minutes at 5°C. the product 1-N the temperature of the chocolate product was 40°C, then cooled at 5°C for 30 minutes without tempering and casting. The resulting chocolate was stored at 20°C for weeks and conducted an assessment of razrabyvaemoy, Shine and ability to melt in your mouth.

Table 11
Recipe of chocolate (wt.%)
ControlThe product (1-T of the present invention)The product (1-N according to the present invention)
Powdered sugar50,650,650,6
Cocoa36,036,036,0
* (cocoa butter)(19,8)(19,8)(19,8)
Cocoa butter12,9
MLCT A12,912,9
Lecithin0,50,50,5

(The results of the evaluation chocolate)

Were evaluated separability from chocolate shapes, razrabyvaemoy, brilliance and ability to melt in your mouth chocolate products obtained in the above way.

The evaluation results are shown in Table 12. Product 1 of the present invention showed good results compared with the control, regardless of whether carried out or not thermoregulation.

Table 12
The results of the evaluation chocolate
ControlThe product (1-T of the present invention)The product (1-N according to the present invention)
The separability from the form
Razrabyvaemoy
Glitter
Characteristics melting point

Criteria

The separability from the form:: separated without effort
: separates with effort
: not separated
Razrabyvaemoy:easy razzhevyvaya
: razzhevyvaya with effort
: not razzhevyvaya (sticks)
Shine:
(estimate by eye)
:very good
: good, but partly dull
: Shine no
Features the specific melting in the mouth: : good
poor

Example 6 (Getting chocolate paste containing intramolecular compounds of the present invention)

Have introduced a variety of fats and oils in accordance with the formulation of Table 13 in Couverture Selectionne Noir (produced by Daito Cacaco Co., Ltd.; the oil content of 40%) to give the chocolate product. The temperature of the chocolate was 40°C, the chocolate was placed in Petri dishes with a diameter of 5 cm and cooled at 5°C for 5 minutes. Then the chocolate is kept at a temperature of 20°C and evaluated the stability of the fat to the opacity, brilliance and ability to melt in your mouth.

Table 13
Recipe chocolate paste (wt.%)
ControlProduct 2 of the present inventionProduct 3 of the present invention
Chocolate glaze505050
Lauric hard butter15
MLCT C 15
MLCT D15

(The results of the evaluation chocolate paste)

Were evaluated the stability turbidity fat, brilliance and ability to melt in your mouth chocolate products obtained in the above way. The evaluation results are shown in Table 14. Products 2 and 3 according to the present invention showed a good stability of fat to increased turbidity in comparison with the control. As the glitter and the ability to melt in your mouth got good grades, was also demonstrated good taste thanks to the use of a large amount of cocoa butter or cocoa mass.

Table 14
The results of the evaluation chocolate glaze
ControlProduct 2 of the present inventionProduct 3 of the present invention
The stability of the fat to increased turbidity (20°C)2(+)
4(++)
30(-)30(-)
Glitter
Characteristics melting point

Criterion

Test for resistance to clouding of the fat number of days:

(+): partial opacity

(++): complete opacity.

Products 1-N, 2 and 3 obtained according to the present invention, were thinly ostrovany knife at a temperature of 20°C. 3 g of chips were placed on filter paper and washed with 150 g of ice water with a temperature of 5°C. Then the precipitate was dried in dessicator and put on the plate, held its measurement using rentgenodiffraction. Although the position of the peaks vary to some extent, but due to the impact of solids non-fat chocolate peaks poorly expressed, this confirms that products 1 and 3, obtained according to the present invention, formed intramolecular compounds of the present invention.

7 and 9 shows the results of measurement (diffraction pattern), and in Tables 15 and 17 the data of these measurements.

Table 15
Product 1-N on the right is briteney
2θ (°)The metric d (Å)Strength (cps)
2,26039,05901160
3,44025,6631142
5,78015,2777226
7,66011,531816
10,5008,418224
14,1006,275916
15,5805,682918
16,4005,4006119
16,7605,285467
17,9204,945832
19,2404,6093560
19,8204,475741
22,200 4,001059
22,8203,8937116
23,3203,811364
23,8803,7232188
24,7803,590047
25,9803,426818
27,0403,294824
27,9403,190722

You can see that the peak corresponds to the (002) reflection parameter bond length 75 Å at 2θ=2,260°, the peak corresponds to the (003) reflection at 2θ=3,440°, and the peak corresponds to the (005) reflection at 2θ=5,780°.

Table 16
(Product 2 of the present invention)
2θ (°)The metric d (Å)Strength (cps)
2,12041,6381227
5,540 21
of 7.92011,153818
15,6805,646918
16,2605,446818
16,9605,223520
20,4604,3372123
20,7604,275260
21,4804,133543
23,5403,7762102
25,3803,506425
26,2603,390923
26,5603,353328
28,8603,091126

You can see that the peak corresponds to the (002) reflection parameter bond length 75 Å at 2θ=2,120°, and the peak corresponds to the (005) reflection is ri 2θ=5,540°.

Table 17
(Product 3 according to the present invention)
2θ (°)The metric d (Å)Strength (cps)
2,14041,2490635
3,30026,751562
5,62015,7123110
7,70011,472017
15,2205,816517
16,3005,433528
16,8005,272924
18,0204,918615
19,1604,628495
20,2204,388149
20,5004,328842/td>
21,1204,203130
21,4204,144929
22,7203,910621
23,2003,830869
23,8603,767357
24,2803,662820
24,8403,581420
27,5203,238418
28,8603,091116

You can see that the peak corresponds to the (002) reflection parameter bond length 75 Å at 2θ=2,140°, the peak corresponds to the (003) reflection at 2θ=3,300°, and the peak corresponds to the (005) reflection at 2θ=5,620°.

1. Product used in chocolate, margarine or shortening, obtained by melting a mixture of components (a) and (b), where component (a) contains a triglyceride dynamising medium chain fatty acids and long-chain monounsaturated fatty acids and (b) contains triglyceride 1,3-dynamising long-chain fatty acids and 2-monounsaturated long-chain fatty acids, moreover, the bond length determined by rentgenodiffraction measured the product is 65 Å or more, and the medium chain fatty acid(s) has from 6 to 12 carbon atoms, and long chain fatty acid(s) is from 14 to 24 carbon atoms.

2. The product according to claim 1, where the medium chain fatty acid(s) has from 6 to 10 carbon atoms, and long chain fatty acid(s) is from 14 to 24 carbon atoms.

3. The product according to claim 1, where the medium chain fatty acid(s) has from 8 to 10 carbon atoms, and long chain fatty acid(s) has from 16 to 18 carbon atoms.

4. Product according to any one of claims 1 to 3, where (a) triglyceride dynamising medium chain fatty acids and long-chain monounsaturated fatty acid is a triglyceride 1,3-dynamising medium chain fatty acids and 2-monounsaturated long-chain fatty acids.

5. Product according to any one of claims 1 to 3, where (b) triglyceride 1,3-dynamising long-chain fatty acids and 2-monounsaturated long-chain fatty acids is one, two or more types selected from 1,3-dipalmitoyl-2-oleoyl glycerin, 1,3-distearoyl-2-oleoyl glycerol and 2-oleoyl, which stearoyl glycerin.

6. Product according to any one of claims 1 to 3, where (b) triglyceride 1,3-dynamising long-chain fatty acids and 2-monounsaturated long-chain fatty acids is the tsya cocoa butter.

7. Product according to any one of claims 1 to 3, where the bond length is determined by rentgenodiffraction is 70 Å or more.

8. Product according to any one of claims 1 to 3, where the bond length is determined by rentgenodiffraction is from 70 to 85 Å.



 

Same patents:

FIELD: power industry.

SUBSTANCE: hydrocarbon fuel obtaining method involves contacting of glycerides of fatty acids with C1-C5 alcohol in presence of solid double cyanide of metals as catalyst at temperature of within 150-200°C during 2-6 hours, cooling of the above reaction mixture to temperature within 20-35°C, filtration of reaction mixture for separation of catalyst with further removal of unreacted alcohol from the obtained filtrate by vacuum distillation so that hydrocarbon fuel is obtained; at that, one metal of catalyst is Zn2+, and the second one is Fe ion.

EFFECT: high output of hydrocarbon fuels.

11 cl, 9 ex, 2 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing carboxylic esters via esterification of carboxylic acids and/or re-esterification of carboxylic esters with methanol or ethanol in the presence of a metallic catalyst, in which the reaction takes place at temperature higher than 150°C, said metallic catalyst is an alkali-earth metal salt and an aliphatic carboxylic acid containing 10-24 carbon atoms, and at the end of esterification or re-esterification, respectively, the metallic catalyst is extracted and then reused as a liquid catalyst in the method of producing carboxylic esters via esterification of carboxylic acids and/or re-esterification of carboxylic esters with methanol or ethanol in the presence of a catalyst. The advantage of the method lies in that, in the initial mixture, free fatty acids can be present in any concentrations. These free fatty acids are also esterified in the said reaction to fatty acid alkyl esters. Hence, low-quality fat/oil can be processed. Another advantage of the method is that, the esterification/re-esterification reaction can also take place in the presence of water. Thus, water-containing material, particularly hydrous alcohol, can also be used. Unreacted free fatty acids or glycerides are returned for esterification/re-esterification, owing to which no losses occur. In contrast to processes without catalysts, the disclosed method has an advantage in that, the reaction can take place with amounts of alcohol which are a little higher than stoichiometric amounts, which markedly increases profitability of the method.

EFFECT: improved method of producing carboxylic esters.

5 cl, 4 tbl, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing a composition of 1,3-dioleoyl-2-palmitoyl glyceride (OPO), meant for producing a human milk fat substitute, comprising (i) fractionation of palm oil or derivative thereof to obtain palm oil stearin with iodine value (IV) 4-11; (ii) enzymatic transesterification of palm oil stearin obtained at step (i) with oleic acid or non-glyceride ester thereof using 1,3-lipase; (iii) separation of the fraction containing OPO glyceride obtained at step (ii) from palmitic acid or palmitic non-glyceride esters.

EFFECT: increase in amount of OPO formed in the product and improved edible quality of the product.

13 cl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to catalysts, particularly used in hydrogenating plant oil and unsaturated fats and can be used in food, perfumery, pharmaceutical, petrochemical and oil-refining industry. Described is a catalyst which contains palladium in amount of 0.1-5.0 wt % and ruthenium in ratio Pd:Ru=1-100 in form of bimetallic particles with size 1-6 nm deposited on a carbon support. Described is a method of preparing the catalyst, involving preliminary combined hydrolysis of palladium (II) and ruthenium (III) chlorides at pH 5-10 and then bringing the precursor into contact with the carbon support and liquid-phase reduction. Described also is a method of hydrogenating triglycerides of plant oil and fats at temperature 80-200°C and pressure 2-15 atm using the catalyst described above.

EFFECT: high efficiency of the method of preparing the catalyst.

2 cl, 5 ex, 2 tbl

FIELD: chemistry.

SUBSTANCE: present invention relates to a reesterification catalyst and its preparation method. The invention describes a reesterification catalyst of general formula: Zn3M2(CN)n(ROH)·xZnCl2·yH2O, where R is tertiary butyl and M is a transition metal ion selected from Fe, Co and Cr; x lies between 0 and 0.5, y lies between 3 and 5 and n equals 10 or 12. Described is a method of preparing the catalyst, involving the following steps: a) dissolving ZnCb in a mixture of water and tertiary butanol, b) adding the said solution obtained from step a) to an aqueous solution of K4Fe(CN)6 while stirring, c) adding a ternary block copolymer of poly(ethylene glycol)-block-poly(propylene glycol)-block-poly(ethylene glycol) (EO20-PO70-EO20; molecular weight of approximately 5800), dissolved in a mixture of tert-butanol and water, to the above mentioned mixture obtained at step (b) while stirring and at temperature 25°C-70°C, d) filtering the reaction mixture obtained at step (c) to obtain a solid product ad then washing with distilled water and drying at temperature 20-50°C and e) activating the said dried solid product at temperature 150-200°C to obtain the desired reesterification catalyst.

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12 cl, 2 tbl, 12 ex

FIELD: food industry.

SUBSTANCE: invention relates to compositions of breast milk fat substitutes, methods of their production, compositions of fat bases and methods of their production; baby formula containing specified substitutes. Composition of fat base according to invention includes mixture of triglycerides of vegetable origin, characterised by the fact that less than 50% of remains of fatty acids bound in sn-2 position are saturated; and/or amount of remains of saturated fatty acids bound in sn-2 position of glycerin frame makes less than approximately 43.5% of overall amount of remains of saturated fatty acids, 45-65% parts of unsaturated fatty acids in sn-1 and sn-3 positions make parts of oleic acid and/or 7-15% parts of unsaturated fatty acids in sn-1 and sn-3 positions make parts of linoleic acid. Composition of breast milk fat substitute according to invention includes mixture of at least 25% or at least 30% of specified composition of fat base according to the invention and up to 75% or accordingly up to 70% of at least one vegetable oil, in which specified vegetable oil is randomised. Baby formula according to invention includes composition of fat base or composition of breast milk fat substitute.

EFFECT: compositions of fat base make it possible to optimally imitate breast milk fat and are suitable for use in various baby formulas, and methods of production provide for low consumption of fat bases in process of their production.

28 cl, 17 tbl

FIELD: food industry.

SUBSTANCE: invention relates to compositions of breast milk fat substitutes, methods of their production, compositions of fat bases and methods of their production; baby formula containing specified substitutes. Composition of fat base according to invention includes mixture of triglycerides of vegetable origin, characterised by the fact that less than 50% of remains of fatty acids bound in sn-2 position are saturated; and/or amount of remains of saturated fatty acids bound in sn-2 position of glycerin frame makes less than approximately 43.5% of overall amount of remains of saturated fatty acids, 45-65% parts of unsaturated fatty acids in sn-1 and sn-3 positions make parts of oleic acid and/or 7-15% parts of unsaturated fatty acids in sn-1 and sn-3 positions make parts of linoleic acid. Composition of breast milk fat substitute according to invention includes mixture of at least 25% or at least 30% of specified composition of fat base according to the invention and up to 75% or accordingly up to 70% of at least one vegetable oil, in which specified vegetable oil is randomised. Baby formula according to invention includes composition of fat base or composition of breast milk fat substitute.

EFFECT: compositions of fat base make it possible to optimally imitate breast milk fat and are suitable for use in various baby formulas, and methods of production provide for low consumption of fat bases in process of their production.

28 cl, 17 tbl

FIELD: process engineering.

SUBSTANCE: invention relates to oil-and-fat industry. Method and system for fermentative treatment of initial material containing lipides comprises brining initial material in contact with process admixture, passing initial material at, in fact, constant flow rate through treatment system that includes several reactors with ferments and stationary layer connected in series. Reactors with stationary layer may be serviced individually while initial material flow rate being, in fact, constant in cutting one reactor off for servicing purposes. Process admixture is, in fact, dehydrated silicon dioxide with pore size exceeding 150 angstrom. Said admixture may be placed in one or several reactors above layer of ferment, or be placed in pretreatment system that includes one or several reactors.

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32 cl, 6 dwg, 20 tbl, 6 ex

FIELD: chemistry.

SUBSTANCE: method involves hydrogenation of polyunsaturated triglycerides in the presence of a noble metal and hydrogen catalyst deposited on a substrate. The noble metal catalyst is a composite of a solid substrate, noble metal particles and a polymer. Temperature of the process lies between 30°C and 200°C and hydrogen pressure is equal to 1-200 bars. Hydrogenated edible oil has iodine number between 60 and 80, between 2.5 and 9 trans-isomers, SC10 between 39 and 47 g/100 g and maximum SC35 of 15 g/100 g, preferably between 2 and 15 g/100 g, where SC10 and SC35 denote content of solid fat at 10°C and 35°C, determined via AOCS method for establishing content of solid fat. Also, frying oil based on hydrogenation of edible oil, has iodine number of at least 80 and content of trans-isomers between 0.5 and 5 wt %. Hydrogenated oil is obtained using the method described above.

EFFECT: invention reduces isomerisation products and enables formation of only a small amount of additional saturated products.

15 cl

FIELD: chemistry.

SUBSTANCE: rape-seed oil is treated with ethyl alcohol through re-esterification in volume ratio 0.5-1.0:10-15 until achieving homogeneous state. The obtained mixture is fed into a reactor in which re-esterification takes place at temperature 250-280°C, pressure 15-20 MPa, for 5-10 minutes. The mixture is cooled and then fed into an extractor. The mixture is the extracted with carbon dioxide in supercritical conditions with carbon dioxide flow rate of 20-35 l/h, temperature 240-260°C and pressure 15-20 MPa. The obtained homogeneous mixture is fed into a first separator for separation of glycerine from the end product at pressure 0.5 MPa and temperature 20-30°C. The end product is fed into a second separator for separation of fatty acid ethyl alcohol from carbon dioxide at pressure 0.2-0.3 MPa and temperature 5-10°C. The end product is fed into the second separator for separation of carbon dioxide at pressure 0.1-0.15 MPa and temperature 10-20°C. Carbon dioxide separated in the second separator is preferably recycled.

EFFECT: simple process.

2 cl, 1 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing carboxylic esters via esterification of carboxylic acids and/or re-esterification of carboxylic esters with methanol or ethanol in the presence of a metallic catalyst, in which the reaction takes place at temperature higher than 150°C, said metallic catalyst is an alkali-earth metal salt and an aliphatic carboxylic acid containing 10-24 carbon atoms, and at the end of esterification or re-esterification, respectively, the metallic catalyst is extracted and then reused as a liquid catalyst in the method of producing carboxylic esters via esterification of carboxylic acids and/or re-esterification of carboxylic esters with methanol or ethanol in the presence of a catalyst. The advantage of the method lies in that, in the initial mixture, free fatty acids can be present in any concentrations. These free fatty acids are also esterified in the said reaction to fatty acid alkyl esters. Hence, low-quality fat/oil can be processed. Another advantage of the method is that, the esterification/re-esterification reaction can also take place in the presence of water. Thus, water-containing material, particularly hydrous alcohol, can also be used. Unreacted free fatty acids or glycerides are returned for esterification/re-esterification, owing to which no losses occur. In contrast to processes without catalysts, the disclosed method has an advantage in that, the reaction can take place with amounts of alcohol which are a little higher than stoichiometric amounts, which markedly increases profitability of the method.

EFFECT: improved method of producing carboxylic esters.

5 cl, 4 tbl, 3 ex

FIELD: chemistry.

SUBSTANCE: raw material composition based on fatty acids or esters of fatty acids, obtained by hydrolysis of oil from seeds or by re-etherification of oil from seeds with C1-8-alkanol, contains more than 70 wt % of unsaturated fatty oleic acid, and less than 1.5 milliequivalents of admixture(s), poisoning methathesis catalyst, per kilogram of composition, after purification with adsorbent. Admixture contains one or more organic hydroperoxides. Method of olefin methathesis lies in contacting of raw composition, obtained from seed oil and containing one or more unsaturated fatty acids or esters of unsaturated fatty acids, with lower olefin in presence of catalyst based on phosphororganic transition metal complex. Used raw material composition contains less than 25 milliequivalents of admixture(s), poisoning methathesis catalyst, per kilogram of raw material composition, able to inhibit methathesis catalyst. As a result of reaction olefin with shortened chain and unsaturated acid or unsaturated ester with shortened chain is obtained. Method of obtaining complex polyether polyepoxide lies in carrying out the following stages. At the first stage raw material compositiojn, obtained from seed oil, containing one or more unsaturated fatty acids or esters of fatty acids, contacts with lower olefin in presence of olefin methathesis catalyst. Used raw material composition contains less than 25 milliequivalents of admixture(s), poisoning methathesis catalyst, per kilogram of composition. At the second stage (re)etherification of obtained unsaturated acid with shortened chain or unsaturated ester with shortened chain with polyol is carried out. At the third stage epoxidation of obtained complex polyether polyolefin is carried out with epoxidising agent optionally in presence of catalyst. Method of obtaining α,ω-oxoacid, complex α,ω-oxyester and/or α,ω-diol with shortened chain lies in carrying out the following stages. At the first stage raw material composition, obtained from seed oil, containing one or more unsaturated fatty acids or esters of fatty acids contacts with lower olefin in presence of olefin methathesis catalyst. Used raw material composition contains less than 25 milliequivalents of admixture(s), poisoning methathesis catalyst, per kilogram of composition. At the second stage hydroformilation is carried out with hydrating of obtained unsaturated acid or ester with shortened chain in presence of hydroformiolation/hydration catalyst.

EFFECT: increase of catalyst serviceability and obtaining chemical compounds with high productivity.

25 cl, 3 tbl, 12 ex

FIELD: medicine, pharmaceutics.

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EFFECT: producing formulations suited for application to hypercholesterolemia therapy and prophylaxis.

3 cl, 4 tbl, 6 ex

FIELD: organic chemistry, labeled compounds.

SUBSTANCE: invention relates to new tritium-labeled 2-arachidonoyl-[1,3-3H]-glycerol of the formula: CH3-(CH2)4-(CH=CHCH2)4-(CH2)2-COOCH-(C3HHOH)2 able to bind and activate cannabinoid receptors. This compound can be used in analytical, bioorganic chemistry, biochemistry and applied medicine.

EFFECT: valuable properties of compound.

1 ex

The invention relates to new compounds with the structure associated 1,3-propane diol, having the ability to penetrate lipid barriers, formula 1, where R1denotes an acyl group or a group of fatty alcohol, derived from C12-30preferably C16-30the fatty acids preferably with two or more double bonds in the CIS - or TRANS-position, and R2denotes hydrogen, acyl group or the group of fatty alcohol, which is the same or different from that specified for R1or is a biologically active residue that is different from the rest of Niacin, the chemical structure of which allows you to connect with 1,3-propane diol through the available carboxyl, alcohol or amino group

The invention relates to organic chemistry, in particular, to a method for producing 2,6-dimethyl-10-methylene-4-C1-C4arcoxia - bonil-2,6,11-dodecatrien

FIELD: chemistry.

SUBSTANCE: method involves mixing starting low-sulphur diesel fuel with a product of re-esterification of plant oil with an aliphatic alcohol - butyl ether of rape-seed oil acids obtained in the presence of concentrated sulphuric acid. The starting diesel fuel is preferably mixed with butyl ether of rape-seed oil acids in weight ratio between 99:1 and 95:5. Antioxidant additive Agidol-12 is additionally added to the said mixture in amount of 0.1 wt %.

EFFECT: obtaining diesel fuel with higher lubricating power.

3 cl, 2 tbl, 8 ex

Catalyst and method // 2316396

FIELD: organic synthesis and catalysts.

SUBSTANCE: invention relates to esterification method utilizing organotitanium or organozirconium catalyst and provides catalytic composition useful in preparation of esters, including polyesters, which contains (i) product of reaction between metal M alcoholate or condensed alcoholate selected from titanium, zirconium, and hafnium alcoholates, (ii) alcohols containing at least two hydroxy groups, (iii) 2-hydroxycarboxylic acid, and (iv) base, wherein molar ratio of base to hydroxycarboxylic acid is within the range between 0.01:1 and 0.79:1. Esterification reaction in presence of above catalyst is also described.

EFFECT: avoided yellowness in final product, raised temperature for the beginning of crystallization and crystallization temperature of polyester.

14 cl, 4 tbl, 20 ex

FIELD: biotechnology, in particular production of antibiotic pravastatin from compactin using microbiological transformation.

SUBSTANCE: microbiological compactin conversion to pravastatin is carried out by cultivation of strain Mortierella maculata n. sp. E-97 capable to hydrolyze pravastatin under deep anaerobic conditions. Broth for strain cultivation contains digestible carbon and nitrogen sources and mineral salts. Pravastatin is isolated from broth and purified. In claim of invention structural formulae of compactin (formula I) and pravastatin (formula II) are provided.

EFFECT: industrial scale method for pravastatin production.

56 cl, 1 dwg, 8 ex

-ketocarboxylic acids" target="_blank">

The invention relates to an improved method of transesterification of esters-ketocarboxylic acid with the structural formula (I), the alcohol of formula (II) R3HE, and R1, R2, R3means a branched, unbranched or cyclic, saturated or unsaturated C1-C6is an alkyl group or benzyl group, and R1and R2are not the same, which are used as, for example, intermediates for biologically active substances for agro - and pharmaceutical industry, as solvents, and so on

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing a composition of 1,3-dioleoyl-2-palmitoyl glyceride (OPO), meant for producing a human milk fat substitute, comprising (i) fractionation of palm oil or derivative thereof to obtain palm oil stearin with iodine value (IV) 4-11; (ii) enzymatic transesterification of palm oil stearin obtained at step (i) with oleic acid or non-glyceride ester thereof using 1,3-lipase; (iii) separation of the fraction containing OPO glyceride obtained at step (ii) from palmitic acid or palmitic non-glyceride esters.

EFFECT: increase in amount of OPO formed in the product and improved edible quality of the product.

13 cl, 2 ex

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