CN103564066B - The frying fluid composition of the ester of aliphatic acid containing antierythrite four and its application - Google Patents
The frying fluid composition of the ester of aliphatic acid containing antierythrite four and its application Download PDFInfo
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Abstract
The present invention relates to one kind to fry fluid composition, is counted on the basis of the gross weight of the frying fluid composition, and the frying fluid composition includes following components：(1) 99.999 50.0 weight % edible oil and fat；(2) the 0.001 50.0 weight % ester of antierythrite aliphatic acid four.The invention further relates to the ester of antierythrite aliphatic acid four as the defoamer of frying fluid composition and/or the application of resistance to frying agent.The invention further relates to a kind of method for being used for reducing the foaming characteristic while the resistance to frying for improving the edible oil and fat of edible oil and fat.
Description
Technical field
The present invention relates to edible oil additive agent field, and more particularly, the present invention relates to one kind to include antierythrite fat
The frying fluid composition of sour four esters.The invention further relates to defoamer of the ester of antierythrite aliphatic acid four as frying fluid composition
And/or the application of resistance to frying agent.The invention further relates to a kind of for reducing the foaming characteristic of edible oil and fat while improving described edible
The method of the resistance to frying of grease.
Background technology
Sugar alcohol fatty acid ester (Alditols fatty acid esters) represents sugar alcohol and aliphatic acid (usually C8-C22
Aliphatic acid) esterification products, be a kind of fat substitute.Present people have developed xylitol, D-sorbite, maltitol
And the fatty acid ester of the sugar alcohol such as mannitol is widely used in food, medicine and cosmetic field as additive.
Antierythrite (Erythritol), also known as erythritol, red rabbitweed alcohol, chemical name is Erythritol.Knot
Structure formula is as shown in Equation 1, widely distributed in nature, be present in marine alga, mushroom class, fruits, lichens plant, microorganism,
In fermented food and animal body fluid etc..Antierythrite is a kind of bulk sweetener with refrigerant mouthfeel, not only possesses sugar
The institute of alcoholic product is functional, the features such as such as preventing carious tooth, suitable for patients with diabetes mellitus, also have unique lower energy content and
The characteristic of high dosis tolerata, belong to the feature sugar substitute of filled-type.
In view of the specific function of antierythrite, its derivative turns into one of study hotspot, erythrose alcohol ester in the world
Fat acid esters is exactly one of which extensively by derivative of concern.
Antierythrite fatty acid ester can be made by the esterification of antierythrite and corresponding aliphatic acid.For example,
Junkui Piao, Takashi Kobayashi, Shuji Adachi et al. is in Biochemical Engineering journal (Biochemical
Engineering Journal) the 79-84 pages of volume 14 of paper " passed through the antierythrite of fixed fat enzymatic 2003 years
The monoleate of antierythrite and dioleate (Synthesis of mono-and are synthesized with the condensation of oleic acid in acetone
dioleoyl erythritols through immobilized-lipase-catalyzed condensation of
Erythritol and oleic acid in acetone [J]) " in disclose esterification condensation by antierythrite and oleic acid
To prepare monoesters and diester.Antierythrite fatty acid ester has special trophic function characteristic, and it is providing low energy to human body
While, reduction fat accumulation, the effect that prevention diabetes, obesity occur can also be played.In addition, due to erythrose
Alcohol fatty acid ester includes hydrophilic segment and hydrophobic part simultaneously, is also used as functional additive, NMF etc., food,
Medicine, cosmetics and chemical field show wide application prospect.For example, in U.S. Patent No. US2006067902A1 and
Disclosed in Chinese Patent No. CN 1649664A antierythrite fatty acid ester cosmetics, coating, ink, memory material and
Application in terms of wetting agent.In July, 2009, GRAS tissues passed through antierythrite fatty acid ester as microcapsule wall material in food
Safety certification.Mentioned using antierythrite fatty acid ester as low-heat in United States Patent (USP) US 5,064,672 and US 5,536,524
Measure fat substitute.TOHKEMY 2005-13061 discloses the bacteriostatic agent being used as antierythrite fatty acid ester in food and beverage.
But so far there is not yet antierythrite fatty acid ester is used to improve oil during grease is heated and fried as lipid-improving agent
The document report of fat anti-foaming and resistance to frying performance.
Edible oil is during frying due to the presence of oxygen gas and water, high temperature and food component, it may occur that it is a series of such as
Hydrolysis, oxidation, the complex reaction of thermal polymerization, make frying oil in color and luster, flavor, viscosity, acid value, peroxide value, polar compound
Deterioration occurs for the quality of content etc., influences the frying performance of grease, or even produces harmful substance, has a strong impact on fried food
Flavor and quality.
In addition, during using edible oil fried food, the material such as starch, albumen in food can be dissolved into frying
In oil, make the increase of frying oil viscosity, cause frying oil constantly to produce white foam, after these foams flood food, operator
Member can be difficult the intensity of variation for observing food in color and luster texture, thus be difficult to the curing time for judging deep fried foodstuff.Moreover, decoct
Frying oil can also diffuse out pot and cause danger, greatly reduce the frying performance of grease and add fuel consumption.It is in addition, many when existing
In the case of foam, the subsidiary Chuck Steak of the food fried out, the mouthfeel of food and attractive in appearance can be also influenceed.It is fried in order to control
Oily foaming in journey, people's general knowledge develop some new technologies, and one of which method is to add silicone oil in frying oil.But thing
Real example is bright, and the anti-foaming effect of silicone oil e insufficient to the needs for meeting practical operation, and its biological degradability is also very low, with
Upper many disadvantages all seriously constrain application of the silicone oil in practical operation.Thus this area grease in the urgent need to address or frying
Oil and improves the outward appearance and mouthfeel of food in the foaming in heat substance process and the problem of intolerant to frying.
The content of the invention
The present inventor have developed the technical scheme to solve the above problems by in-depth study.
In the first aspect of the invention, there is provided one kind frying fluid composition, with the gross weight of the frying fluid composition
Counted on the basis of amount, the frying fluid composition includes following components：
(1) 99.999-50.0 weight % edible oil and fat；
(2) the 0.001-50.0 weight % ester of antierythrite aliphatic acid four.
In an embodiment of this aspect, the ester of antierythrite aliphatic acid four is by antierythrite and comprising 2-28
The ester of antierythrite aliphatic acid four that the aliphatic acid of the straight or branched of individual carbon atom is formed, the aliphatic acid of the straight or branched are excellent
Choosing includes 4-22 carbon atom, more preferably comprising 12-20 carbon atom, more preferably comprising 12-18 carbon atom, most preferably comprises
16-18 carbon atom；The aliphatic acid of the straight or branched be preferably laurate, palmitic acid, stearic acid, arachidic acid or it
Combination.
In another embodiment of this aspect, counted on the basis of the gross weight of the frying fluid composition, erythrose
The content of the ester of polyol fatty acid four is 0.01-35 weight %, preferably preferably 0.01-30 weight %, 0.1-20 weight %.
In another embodiment of this aspect, the edible oil and fat are selected from：Palm oil, soybean oil, high oleic acid sunflower
Seed oil, sunflower oil, cottonseed oil, rice bran oil, tea-seed oil, safflower seed oil, rapeseed oil, corn oil, peanut oil, sesame oil, olive
Oil, apricot kernel oil, walnut oil, linseed oil, fish oil, lard, butter, sheep oil, margarine, butter, shortening or any two
The mixture of kind or more kind oils.
In the second aspect of the invention, there is provided defoaming of the ester of antierythrite aliphatic acid four as frying fluid composition
Agent and/or the application of resistance to frying agent.In an embodiment of this aspect, using the gross weight of the frying fluid composition as base
Quasi- meter, the frying fluid composition include following components：
(1) 99.999-50.0 weight % edible oil and fat；
(2) the 0.001-50.0 weight % ester of antierythrite aliphatic acid four.
In another embodiment of this aspect, the ester of antierythrite aliphatic acid four is by antierythrite and comprising 2-
The ester of antierythrite aliphatic acid four that the aliphatic acid of the straight or branched of 28 carbon atoms is formed, the aliphatic acid of the straight or branched
4-22 carbon atom is preferably comprised, more preferably comprising 12-20 carbon atom, more preferably comprising 12-18 carbon atom, is most preferably wrapped
Containing 16-18 carbon atom；The aliphatic acid of the straight or branched be preferably laurate, palmitic acid, stearic acid, arachidic acid or
Combinations thereof.
In another embodiment of this aspect, counted on the basis of the gross weight of the frying fluid composition, erythrose
The content of the ester of polyol fatty acid four is 0.01-35 weight %, preferably preferably 0.01-30 weight %, 0.1-20 weight %.
In another embodiment of this aspect, the edible oil and fat are selected from：Palm oil, soybean oil, high oleic acid sunflower
Seed oil, sunflower oil, cottonseed oil, rice bran oil, tea-seed oil, safflower seed oil, rapeseed oil, corn oil, peanut oil, sesame oil, olive
Oil, apricot kernel oil, walnut oil, linseed oil, fish oil, lard, butter, sheep oil, margarine, butter, shortening or any two
The mixture of kind or more kind oils.
In the third aspect of the invention, there is provided a kind of to be used for reducing edible oil and fat rising during heating and frying
The method steeped while improve the resistance to frying of the edible oil and fat, this method comprise the following steps：
(a) edible oil and fat are heated to 50-80 DEG C；
(b) at a temperature of 50-80 DEG C, the ester of antierythrite aliphatic acid four is added in the edible oil and fat so that described
The ester of antierythrite aliphatic acid four is dissolved completely in the edible oil and fat, with the ester of antierythrite aliphatic acid four and edible oil and fat
Gross weight on the basis of count, the dosage of the ester of antierythrite aliphatic acid four is 0.001-50.0 weight %.
In an embodiment of this aspect, the ester of antierythrite aliphatic acid four is by antierythrite and comprising 2-28
The ester of antierythrite aliphatic acid four that the aliphatic acid of the straight or branched of individual carbon atom is formed, the aliphatic acid of the straight or branched are excellent
Choosing includes 4-22 carbon atom, more preferably comprising 12-20 carbon atom, more preferably comprising 12-18 carbon atom, most preferably comprises
16-18 carbon atom；The aliphatic acid of the straight or branched be preferably laurate, palmitic acid, stearic acid, arachidic acid or it
Combination.
In another embodiment of this aspect, the content of the ester of antierythrite aliphatic acid four is 0.01-35 weight %, preferably
0.01-30 weight %, preferably 0.1-20 weight %.
In another embodiment of this aspect, the edible oil and fat are selected from：Palm oil, soybean oil, high oleic acid sunflower
Seed oil, sunflower oil, cottonseed oil, rice bran oil, tea-seed oil, safflower seed oil, rapeseed oil, corn oil, peanut oil, sesame oil, olive
Oil, apricot kernel oil, walnut oil, linseed oil, fish oil, lard, butter, sheep oil, margarine, butter, shortening or any two
The mixture of kind or more kind oils.
Embodiment
The present invention will be further described in detail in herein below.It should be noted however that following
Embodiment only provides the concrete operations example of the present invention in an exemplary fashion, but protection scope of the present invention is not
It is only limitted to this.Protection scope of the present invention is only limited only by the claims that follow.Those skilled in the art can be apparently
Expect, can claims of the present invention limit protection domain within to embodiment of the present invention carry out it is various its
Its improvement and replacement, and remain able to realize identical technique effect, reach the final technical purpose of the present invention.
In the present invention, unless indicated to the contrary, all ratios are weight ratio, and all percentage is weight
Percentage, the unit of temperature for DEG C, the unit of pressure is pa.Room temperature refers to environment temperature conventional in laboratory, with season and position
Change is put, usually 25 DEG C.In addition, all number ranges that the present invention describes include end value and can included by disclosed in
The upper and lower bound of scope is combined mutually obtained new number range.If for example, disclose the weight of certain component
Percentage composition is 10 ~ 30 weight %, preferably 15 ~ 25 weight %, more preferably 20 ~ 23 weight %, then equivalent to also disclose with
Under number range：10 ~ 15 weight %, 10 ~ 25 weight %, 10 ~ 20 weight %, 10 ~ 23 weight %, 15 ~ 30 weight %, 15 ~
20 weight %, 15 ~ 23 weight %, 20 ~ 25 weight %, 23 ~ 25 weight %.
The present invention is reduced by the way that the ester of aliphatic acid four of antierythrite is added in edible oil and fat during high temperature frying
The foaming degree of edible oil and fat, while the stability of edible oil and fat can be improved, substantially reducing it can during high temperature frying
The problem of acidity, viscosity and the polar compounds content that can occur increase.
In the present invention, term " edible oil and fat " and " frying oil " are interchangeable, and are represented by plant refinement or people
Any oils that can be used for fried food that work synthesis technique obtains, including but not limited to palm oil, soybean oil, high oleic acid certain herbaceous plants with big flowers
Flower seed oil, sunflower oil, cottonseed oil, rice bran oil, tea-seed oil, safflower seed oil, rapeseed oil, corn oil, peanut oil, sesame oil, olive
Olive oil, apricot kernel oil, walnut oil, linseed oil, fish oil, lard, butter, sheep oil, margarine, butter, shortening, can also be
The mixture of two or more any above-mentioned oils, such as ready-mixed oil etc..
Antierythrite is a kind of polyalcohol for including four hydroxyls, and " ester of antierythrite aliphatic acid four " represents antierythrite
Four hydroxyls all with the product that is formed afterwards of aliphatic acid esterification, in other words, the esterification journey of the hydroxyl of its mesoerythrit
Spend for 100%.Formed after four esters, antierythrite is no longer comprising can be by forming ehter bond the hydroxyl that is condensed, therefore red moss
The ester of sugar alcohol fatty acid four can not possibly be as homologue (such as monoesters, diester and three esters) of its degree of esterification less than 100%, shape
Into dimer or polymer, this also result in the significant difference of the ester of antierythrite aliphatic acid four and its monoesters, diester and three esters.Hair
This will be described in detail below in an example by a person of good sense.Although the every kind of red moss used in specific examples below
In the ester of sugar alcohol fatty acid four, with antierythrite into four fatty acid residues of ester be all identical, but the present invention also include it
In the different situation of four fatty acid residues.For example, it is also possible to rubbed using one mole of antierythrite and two moles of laurate and two
You are esterified to form four esters stearic acid, or use one mole of antierythrite and laurate, palmitic acid, stearic acid and arachidic acid each one
Mole it is esterified.
In the present invention, the aliphatic acid for being esterified with antierythrite can be the aliphatic acid of straight or branched, can wrap
Containing 2-28 carbon atom, 4-22 carbon atom is preferably comprised, more preferably comprising 12-20 carbon atom, more preferably comprising 12-18
Carbon atom, most preferably comprise 16-18 carbon atom.In a preferred embodiment, the aliphatic acid of the straight or branched is
Laurate, palmitic acid, stearic acid, arachidic acid or combinations thereof.
In an embodiment of the invention, counted on the basis of the gross weight of the frying fluid composition finally obtained, it is red
The content of the ester of moss sugar alcohol fatty acid four is 0.001-50 weight, preferably 0.01-35 weight %, preferably 0.01-30 weight %, more preferably
0.1-20 weight %.Correspondingly, in fluid composition is fried, the content of edible oil and fat is 99.999-50.0 weight %, preferably
99.99-70 weight %, more preferably 99.9-80 weight %.According to the source and specific production of specific needs and edible oil and fat
Technique, described fry in fluid composition can also optionally include other additives well known in the art, such as preservative, color development
Agent, bleaching agent, acid, coagulator, raising agent, thickener, sweetener, quality improver, anticaking agent, enzyme preparation, fruit glaze agent,
Spices, nutrition fortifier etc..
In an embodiment of the invention, the ester of antierythrite aliphatic acid four is added into edible oil and fat in the following manner
In：Edible oil and fat are heated first, are preferably heated to 50-80 DEG C, but the temperature range can also be 60-70 DEG C, or
Person in the temperature change less than 50 DEG C or higher than 80 DEG C, then adds the ester of antierythrite aliphatic acid four described edible as needed
In grease, it is set to be dissolved completely in edible oil and fat.Wait after being completely dissolved, this can be cooled to normal temperature using grease, stayed
It is for later use, oil temperature can also be further increased to conventional food frying temperature, such as 150-200 DEG C, carried out immediately
Food frying operations.
The preferred embodiment of the present invention is illustrated below by way of specific embodiment, but these embodiments are only
The purpose illustrated, the scope of the present invention are defined by the claims, rather than are only limitted to these specific embodiments.
Embodiment
Prepare embodiment：The antierythrite fatty acid ester of four kinds of different esters of antierythrite aliphatic acid four and relatively low esterification degree
Synthesis and sign
In this preparation embodiment, corresponding erythrose is prepared using laurate, palmitic acid, stearic acid and arachidic acid respectively
The ester of polyol fatty acid four, for antifoam performance afterwards and anti-frying performance test embodiment.Also it is prepared in addition using palmitic acid
The antierythrite fatty acid ester of relatively low esterification degree is used for carrying out control experiment.
Prepare the ester of embodiment i antierythrites laurate four
Weigh 410 grams of (2.05 moles) laurate and 50 grams of (0.41 mole) antierythrites added in 2 liters of three-necked flask,
And reflux condensate device, mechanical agitator and addition funnel are installed for the flask.The burning is added using 1 liter of toluene as reflux solvent
In bottle, catalysts p-methyl benzenesulfonic acid (23 grams, 5 weight %) is then added.Start agitating device, the mixture is heated
To 135 DEG C, and in this temperature reflux 42 hours, after reaction terminates, unreacted antierythrite is filtered to remove while hot, is cooled to
Room temperature, 1 hour is stood, with Buchner funnel filtered off with suction, is washed with 1500 milliliters of saturated sodium bicarbonate aqueous solutions, then with 1200
Milliliter petroleum ether, then recrystallized with 800 milliliters of petroleum ethers, 300 grams of productions are obtained after air drying in vacuum drying oven
Thing.CDCl of the NMR of the AVANCE II models produced using Brooker (BRUKER) company to the product3Solution enters
OK1H NMR characterize (400MHz), as a result as follows:δ0.88(12H,t,J=6.9Hz),1.26(64H,m),1.60(8H,m),
2.31(8H,t,J=7.6Hz),4.15(2H,m),4.33(2H,m),5.28(2H,m).Nuclear-magnetism characterization result shows that product is red
The ester of moss sugar alcohol laurate four.
Prepare the ester of embodiment ii antierythrites palmitic acid four
The reaction system and nuclear-magnetism instrument in embodiment i made above are used in this experiment.Weigh 524.8 gram (2.05
Mole) palmitic acid and 50 grams of (0.41 mole) antierythrites add in three-necked flasks, 1 liter of toluene is added into the flask and is used as back
Solvent is flowed, then adds catalysts p-methyl benzenesulfonic acid (28.8 grams, 5 weight %).The mixture is small in 138 DEG C of backflows 48
When, after reaction terminates, unreacted reactant is filtered to remove while hot, is cooled to room temperature, is stood 1 hour, is taken out with Buchner funnel
Filtration filter, is washed with 1500 milliliters of saturated sodium bicarbonate aqueous solutions, then with 1500 milliliters of petroleum ethers, with 900 milliliters of stones
Oily ether is recrystallized, and obtains 330 grams of products after air drying in vacuum drying oven.To the CDCl of the product3Solution is carried out1H
NMR characterizes (400MHz), as a result as follows:δ0.88(12H,t,J=6.8Hz),1.26(96H,m),1.59(8H,m),2.31(8H,
t,J=7.6Hz),4.13(2H,m),4.33(2H,m),5.27(2H,m).Nuclear-magnetism characterization result shows product for antierythrite palm fibre
Palmitic acid four esters of acid.
Prepare the ester of embodiment iii antierythrites stearic acid four
The reaction system and nuclear-magnetism instrument in embodiment i made above are used in this experiment.Weigh 582.2 gram (2.05
Mole) stearic acid and 50 grams of (0.41 mole) antierythrites add in three-necked flasks, 1 liter of toluene is added into the flask and is used as back
Solvent is flowed, then adds catalysts p-methyl benzenesulfonic acid (31.6 grams, 5 weight %).The mixture is small in 145 DEG C of backflows 48
When, after reaction terminates, unreacted reactant is filtered to remove while hot, is cooled to room temperature, is stood 1 hour, is taken out with Buchner funnel
Filtration filter, is washed with 1500 milliliters of saturated sodium bicarbonate aqueous solutions, then with 1500 milliliters of petroleum ethers, with 1000 milliliters of stones
Oily ether is recrystallized, and obtains 350 grams of products after air drying in vacuum drying oven.To the CDCl of the product3Solution is carried out1H
NMR characterizes (400MHz), as a result as follows:δ0.88(12H,t,J=6.8Hz),1.26(112H,m),1.59(8H,m),2.30
(8H,t,J=7.7Hz),4.13(2H,m),4.35(2H,m),5.25(2H,m).Nuclear-magnetism characterization result shows that product is erythrose
The ester of alcohol stearic acid four.
Prepare the ester of embodiment iv antierythrites arachidic acid four
The reaction system and nuclear-magnetism instrument in embodiment i made above are used in this experiment.Weigh 639.6 gram (2.05
Mole) arachidic acid and 50 grams of (0.41 mole) antierythrites add in three-necked flasks, 1 liter of toluene is added into the flask and is used as back
Solvent is flowed, then adds catalysts p-methyl benzenesulfonic acid (34.5 grams, 5 weight %).The mixture is small in 145 DEG C of backflows 56
When, after reaction terminates, unreacted reactant is filtered to remove while hot, is cooled to room temperature, is stood 1 hour, is taken out with Buchner funnel
Filtration filter, is washed with 1500 milliliters of saturated sodium bicarbonate aqueous solutions, then with 1500 milliliters of petroleum ethers, with 1200 milliliters of stones
Oily ether is recrystallized, and obtains 380 grams of products after air drying in vacuum drying oven.To the CDCl of the product3Solution is carried out1H
NMR characterizes (400MHz), as a result as follows:δ0.88(12H,t,J=6.9Hz),1.26(128H,m),1.61(8H,m),2.32
(8H, t, J=7.8Hz), 4.13 (2H, m), 4.35 (2H, m), 5.26 (2H, m) nuclear-magnetism characterization results show that product is antierythrite
The ester of arachidic acid four.
Prepare embodiment v：The preparation of the ester of antierythrite palmitic acid one
Weigh 105 grams of (0.41 mole) palmitic acids and 150 grams（1.23 mole）Antierythrite adds 2 liters of three-necked flask
In, and reflux condensate device, mechanical agitator and addition funnel are installed for the flask.1 liter of hexamethylene is added as reflux solvent
Enter in the flask, then add phase transfer catalyst cetyl trimethylammonium bromide（7.65 grams, 3 weight %）And catalytic reaction
Agent p-methyl benzenesulfonic acid（5.1 grams, 2 weight %）.Start agitating device, the mixture is heated to 95 DEG C, and in this temperature reflux
8 hours, after reaction terminates, unreacted antierythrite is filtered to remove while hot, is cooled to room temperature, is stood 1 hour, is leaked with Bu Shi
Struggle against filtered off with suction, is washed with 1500 milliliters of saturated sodium bicarbonate aqueous solutions, then with 800 milliliters of petroleum ethers, is dried in vacuum
80 grams of products are obtained in case after air drying.Petroleum ether is solvent, product：Petroleum ether=1:3（Weight/volume）, 80 DEG C have been heated
Fully dissolved, 25 DEG C of crystallizations.Obtained product purity more than 98% is crystallized twice.Use German Brooker（Bruker）Company produces
AVANCE II types NMRs to the CDCl of the product3Solution is carried out1H NMR characterize (400MHz), as a result as follows:δ
0.88(3H,t,J=6.8Hz),1.25(24H,m),1.64(2H,m),2.39(2H,t,J=7.6Hz),3.71(1H,dd,J=
5.6Hz),3.81(1H,dd,J=4Hz),3.97(1H,dd,J=5.6Hz),4.07(1H,dd,J=5.6Hz),4.45(1H,m),
5.14(1H,m).As a result prove that it is the ester of antierythrite palmitic acid one that product, which is made,.
Prepare embodiment vi：The preparation of antierythrite palm acid diesters
The reaction system and NMR in embodiment i made above are used in this experiment.Weigh 210 gram (0.82
Mole) palmitic acid and 50 grams（0.41 mole）Antierythrite is added in three-necked flask, and 1 liter of toluene is added into the flask and is used as back
Solvent is flowed, then adds catalysts p-methyl benzenesulfonic acid（7.8 grams, 3 weight %）.The mixture is small in 130 DEG C of backflows 24
When, after reaction terminates, unreacted antierythrite is filtered to remove while hot, is cooled to room temperature, is stood 1 hour, is used Buchner funnel
Filtered off with suction, washed with 1500 milliliters of saturated sodium bicarbonate aqueous solutions, then with 1200 milliliters of petroleum ethers, in vacuum drying oven
220 grams of products are obtained after middle air drying.Petroleum ether is solvent, product：Petroleum ether=1:3（Weight/volume）, 80 DEG C have been heated
Fully dissolved, 25 DEG C of crystallizations.Obtained product purity more than 98% is crystallized twice.To the CDCl of the product3Solution is carried out1H NMR tables
Levy (400MHz), it is as a result as follows:δ0.88(6H,t,J=6.8Hz),1.26(48H,m),1.61(4H,m),2.32(4H,t,J=
7.6Hz),3.80(2H,dd,J=4Hz),4.08(2H,dd,J=5.6Hz),5.32(2H,m).Nuclear-magnetism characterization result shows product
For antierythrite palm acid diesters.
Prepare embodiment vii：The preparation of the ester of antierythrite palmitic acid three
The reaction system and NMR in embodiment i made above are used in this experiment.Weigh 315 gram (1.23
Mole) palmitic acid and 50 grams（0.41 mole）Antierythrite is added in three-necked flask, and 1 liter of toluene is added into the flask and is used as back
Solvent is flowed, then adds catalysts p-methyl benzenesulfonic acid（14.6 grams, 4 weight %）.The mixture is small in 133 DEG C of backflows 36
When, after reaction terminates, unreacted antierythrite is filtered to remove while hot, is cooled to room temperature, is stood 1 hour, is used Buchner funnel
Filtered off with suction, washed with 1500 milliliters of saturated sodium bicarbonate aqueous solutions, then with 1500 milliliters of petroleum ethers, with 700 milliliters
Petroleum ether is recrystallized, and obtains 240 grams of products after air drying in vacuum drying oven.Petroleum ether is solvent, product：Petroleum ether
=1:3（Weight/volume）, 80 DEG C of heating are completely dissolved, 25 DEG C of crystallizations.Obtained product purity more than 98% is crystallized twice.To this
The CDCl of product3Solution is carried out1H NMR characterize (400MHz), as a result as follows:δ0.88(9H,t,J=6.8Hz),1.26(72H,
m),1.64(6H,m),2.39(6H,m),3.73(1H,m),3.85(1H,m),3.97(1H,m),4.23(1H,m),4.65(1H,
m),5.24(1H,m).Nuclear-magnetism characterization result shows that product is the ester of antierythrite palmitic acid three.
Testing example：Use the other polynary of antierythrite fatty acid ester made from embodiment made above and preparation
Alcohol fatty acid ester has carried out frying experiment.
Table 1 below lists embodiment 1-70 experiment condition and result.Soybean oil is used in these embodiments, is listed in table
The ester of antierythrite four and the contents of other additives be the weight hundred for counting to obtain on the basis of frying oil composition total weight
Fraction.For example, in embodiment 8 display represents the frying that the embodiment uses using 5.0% ester of antierythrite laurate four
The ester of antierythrite laurate four of soybean oil of the oil comprising 95.0 weight % and 5.0 weight %.The wood used in embodiment 51-67
Sugar alcohol palmitic acid five-ester, xylitol laurate five-ester, xylitol stearic acid five-ester, the ester of D-sorbite palmitic acid six, D-sorbite
The ester of laurate six and the ester of D-sorbite stearic acid six are according to By J.F.Carson, Jr., W.D.Maclay report documents institute
The step of stating synthesizes.（By J.F.Carson, Jr., W.D.Maclay.Xylitol esters of fatty acids [J]
.J.Am.Chem.Soc, 1994,66 (9):1609-1610.）
In each embodiment 1-70, the frying experiment of French fries is followed the steps below：Weigh 500 grams of corresponding frying oils
Composition, it is respectively put into 1000 milliliters of beaker, 180 DEG C is heated on Electromagnetic Heating agitator, is keeping the bar of constant temperature
The frying experiment of French fries is carried out under part.In the morning, French fries are fried 5 times using the frying fluid composition in beaker, every time using 20g
French fries are fried 4 minutes.After having fried, French fries are taken out, then keep 180 DEG C of constant temperature to add remaining frying fluid composition in beaker
Heat 3 hours, carry out the frying operations of 5 French fries respectively in an identical manner again in the afternoon, oil sample 100 is taken out after being fried
Gram, then stop heating, natural cooling, frying in so far the 1st day terminates.The frying of 3 days is carried out as stated above, after frying terminates
Acid number, polar compound, viscosity and the bubble high level of detection frying terminal oil sample, while 3 groups of parallel tests are carried out, calculate average
Value, as a result collects and is listed in table 1.
Acid value measuring：Carried out with reference to national standard GB/T5530.
Polar compounds content determines：Use edible oil quality detector testo 270（Purchased from testo companies）Measure is decocted
Fried content of polar compound in grease.
Viscosimetric analysis：Use SVM 3000G2 dynamic viscosity admeasuring apparatus（Anton Paar companies）Determine the viscous of frying fat and oil
Degree.
Steep high level measure：The commercially available potato slices of constant-quality are put into 180 DEG C to treat in frying oil, recorded 5 ~ 20 seconds
When highest bubble high level, be this time bubble high level.
In the test result provided in table, the result of " before frying " is that the oil sample in beaker is not carrying out the feelings of any frying
The result measured under condition, and the result of " after frying " is final result of the same oil sample after frying in 3 days.
Application of the antierythrite fatty acid ester of table 1 in soybean oil frying
In following embodiment 71-135, above example 1-70 operating procedure is repeated, but use rapeseed oil generation
For soybean oil as edible oil and fat, the ester of measure antierythrite aliphatic acid four and other additives answering in rapeseed oil frying
With.The poly- antierythrite fatty acid ester used in embodiment 135 is with reference to the more benevolence report literature procedure synthesis of Wang.（The more benevolence of Wang gather sweet
The synthesis application of oil and fat acid esters and the market development [J] Surfactant Industries, 1998,2:1-2.）
Application of the antierythrite fatty acid ester of table 2 in rapeseed oil frying
It can see from above experimental data, by the way that the ester of antierythrite aliphatic acid four is added in frying oil, heating
During frying, the foaming of grease is significantly reduced, in addition, after long-time frying operations process, the acid number of frying oil,
Viscosity and polar compound increase degree receive significant suppression so that grease has preferably frying performance.Inventor is also
Although it has furthermore been found that sour six esters of xylose polyol fatty acid five-ester and polyoxyethylensorbitan fatty be all 100% esterification linear saturation it is more
First alcohol fatty acid ester, with the structure of antierythrite quite it is similar, but when these esters are added in frying oil, can not rise
To the significant effect for reducing foaming and improving resistance to frying property.Applicant also further using the monoesters of antierythrite, diester and
Three esters and its oligomer have carried out contrast experiment, as a result find when the esterification degree of antierythrite is less than 100%, reduce
The effect bubbled and improve resistance to frying property is also considerably insignificant.In summary, the present inventor extremely surprisingly has found,
When the ester of antierythrite aliphatic acid four that esterification degree is 100% is added in edible oil and fat, it can heat and fry
Foaming is substantially reduced in journey and improves resistance to frying, improves the performance of frying oil, extends its service life so that frying culinary art behaviour
Make significantly to simplify, improve the mouthfeel of fried food.
It is another advantage of the present invention that compared with silicone oil used in prior art, the ester of antierythrite aliphatic acid four
It is a kind of fat substitute of low energy, there is the similar physicochemical property of conventional fat, internal digestion and metabolism speed is compared with glycerine three
Ester is slow, and compared with the indigestion of noenergy sucrose Polyester, it is higher to the security of human body, reducing the accumulation of body fat
There are various disease effects caused by prevention high fat meal simultaneously.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not limited to the substantial technological content model of the present invention
Enclose, substantial technological content of the invention is broadly to be defined in the right of application, any technology that other people complete
Entity or method, if with the right of application defined in it is identical, also or a kind of equivalent change, will
It is considered as being covered by among the right.
All it is incorporated as referring in this application in all documents that the present invention refers to, it is independent just as each document
It is incorporated as with reference to such.In addition, it is to be understood that after the above of the present invention has been read, those skilled in the art can be right
The present invention makes various changes or modifications, and these equivalent form of values equally fall within the application appended claims limited range.
Claims (27)
1. one kind frying fluid composition, counted on the basis of the gross weight of the frying fluid composition, the frying fluid composition bag
Containing following components：
(1) 99.99-70.0 weight % edible oil and fat；
(2) the 0.01-30.0 weight % ester of antierythrite aliphatic acid four.
2. frying fluid composition as claimed in claim 1, it is characterised in that the ester of antierythrite aliphatic acid four is by red moss
The ester of antierythrite aliphatic acid four that the aliphatic acid of sugar alcohol and the straight or branched comprising 2-28 carbon atom is formed.
3. frying fluid composition as claimed in claim 2, it is characterised in that the aliphatic acid of the straight or branched includes 4-22
Individual carbon atom.
4. frying fluid composition as claimed in claim 2, it is characterised in that the aliphatic acid of the straight or branched includes 12-
20 carbon atoms.
5. frying fluid composition as claimed in claim 2, it is characterised in that the aliphatic acid of the straight or branched includes 12-
18 carbon atoms.
6. frying fluid composition as claimed in claim 2, it is characterised in that the aliphatic acid of the straight or branched includes 16-
18 carbon atoms.
7. frying fluid composition as claimed in claim 2, it is characterised in that the aliphatic acid of the straight or branched is bay
Acid, palmitic acid, stearic acid, arachidic acid or combinations thereof.
8. frying fluid composition as claimed in claim 1, it is characterised in that using the gross weight of the frying fluid composition as base
Quasi- meter, the content of the ester of antierythrite aliphatic acid four is 0.1-20 weight %.
9. frying fluid composition as claimed in claim 1, it is characterised in that the edible oil and fat are selected from：Palm oil, soybean
Oil, high oleic sunflower oil, sunflower oil, cottonseed oil, rice bran oil, tea-seed oil, safflower seed oil, rapeseed oil, corn oil, peanut
Oil, sesame oil, olive oil, apricot kernel oil, walnut oil, linseed oil, fish oil, lard, butter, sheep oil, margarine, butter, rise
The mixture of butter or two or more any oils.
10. the ester of antierythrite aliphatic acid four is as the defoamer of frying fluid composition and/or the application of resistance to frying agent；Decocted with described
Counted on the basis of the gross weight of frying oil composition, the frying fluid composition includes following components：
(1) 99.99-70.0 weight % edible oil and fat；
(2) the 0.01-30.0 weight % ester of antierythrite aliphatic acid four.
11. application as claimed in claim 10, it is characterised in that the ester of antierythrite aliphatic acid four be by antierythrite with
The ester of antierythrite aliphatic acid four that the aliphatic acid of straight or branched comprising 2-28 carbon atom is formed.
12. application as claimed in claim 11, it is characterised in that it is former that the aliphatic acid of the straight or branched includes 4-22 carbon
Son.
13. application as claimed in claim 11, it is characterised in that the aliphatic acid of the straight or branched includes 12-20 carbon
Atom.
14. application as claimed in claim 11, it is characterised in that the aliphatic acid of the straight or branched includes 12-18 carbon
Atom.
15. application as claimed in claim 11, it is characterised in that the aliphatic acid of the straight or branched includes 16-18 carbon
Atom.
16. application as claimed in claim 11, it is characterised in that the aliphatic acid of the straight or branched is laurate, palm
Acid, stearic acid, arachidic acid or combinations thereof.
17. application as claimed in claim 10, it is characterised in that counted on the basis of the gross weight of the frying fluid composition,
The content of the ester of antierythrite aliphatic acid four is 0.1-20 weight %.
18. application as claimed in claim 10, it is characterised in that the edible oil and fat are selected from：Palm oil, soybean oil, high oil
Sour sunflower oil, sunflower oil, cottonseed oil, rice bran oil, tea-seed oil, safflower seed oil, rapeseed oil, corn oil, peanut oil, sesame
Oil, olive oil, apricot kernel oil, walnut oil, linseed oil, fish oil, lard, butter, sheep oil, margarine, butter, shortening or
The mixture of two or more any oils of person.
19. a kind of be used for reducing foaming of the edible oil and fat during heating and frying while improve the resistance to of the edible oil and fat
The method of frying property, this method comprise the following steps：
(a) edible oil and fat are heated to 50-80 DEG C；
(b) at a temperature of 50-80 DEG C, the ester of antierythrite aliphatic acid four is added in the edible oil and fat so that the red moss
The ester of sugar alcohol fatty acid four is dissolved completely in the edible oil and fat, with the total of the ester of antierythrite aliphatic acid four and edible oil and fat
Counted on the basis of weight, the dosage of the ester of antierythrite aliphatic acid four is 0.01-30.0 weight %.
20. method as claimed in claim 19, it is characterised in that the ester of antierythrite aliphatic acid four be by antierythrite with
The ester of antierythrite aliphatic acid four that the aliphatic acid of straight or branched comprising 2-28 carbon atom is formed.
21. method as claimed in claim 20, it is characterised in that it is former that the aliphatic acid of the straight or branched includes 4-22 carbon
Son.
22. method as claimed in claim 20, it is characterised in that the aliphatic acid of the straight or branched includes 12-20 carbon
Atom.
23. method as claimed in claim 20, it is characterised in that the aliphatic acid of the straight or branched includes 12-18 carbon
Atom.
24. method as claimed in claim 20, it is characterised in that the aliphatic acid of the straight or branched includes 16-18 carbon
Atom.
25. method as claimed in claim 20, it is characterised in that the aliphatic acid of the straight or branched is laurate, palm
Acid, stearic acid, arachidic acid or combinations thereof.
26. method as claimed in claim 19, it is characterised in that the content of the ester of antierythrite aliphatic acid four is 0.1-20 weights
Measure %.
27. method as claimed in claim 19, it is characterised in that the edible oil and fat are selected from：Palm oil, soybean oil, high oil
Sour sunflower oil, sunflower oil, cottonseed oil, rice bran oil, tea-seed oil, safflower seed oil, rapeseed oil, corn oil, peanut oil, sesame
Oil, olive oil, apricot kernel oil, walnut oil, linseed oil, fish oil, lard, butter, sheep oil, margarine, butter, shortening or
The mixture of two or more any oils of person.
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| CN201210262336.6A CN103564066B (en) | 2012-07-26 | 2012-07-26 | The frying fluid composition of the ester of aliphatic acid containing antierythrite four and its application |
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| CN104738360B (en) * | 2015-02-11 | 2017-08-01 | 河南工业大学 | It is a kind of to eliminate the method that corn oil fries foam |
| CN108236018B (en) * | 2016-12-27 | 2022-02-18 | 丰益(上海)生物技术研发中心有限公司 | Special natural defoamer compound mixture for frying grease |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1151105A (en) * | 1994-05-06 | 1997-06-04 | 卡夫食品有限公司 | Method for making reduced calorie peanut products |
| CN1219850A (en) * | 1996-04-29 | 1999-06-16 | 普罗克特和甘保尔公司 | Process for preparing improved oven-finished French fried potato strips |
| CN1220581A (en) * | 1996-05-02 | 1999-06-23 | 普罗克特和甘保尔公司 | Parfried food products containing low levels of free fatty acids and polymers |
| CN101919451A (en) * | 2009-06-16 | 2010-12-22 | 嘉里特种油脂（上海）有限公司 | Grease combination and application thereof |
| CN102524909A (en) * | 2010-12-31 | 2012-07-04 | 丰益(上海)生物技术研发中心有限公司 | Antibacterial composition containing erythritol fatty acid esters and preparation method and application of antibacterial composition |
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2012
- 2012-07-26 CN CN201210262336.6A patent/CN103564066B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1151105A (en) * | 1994-05-06 | 1997-06-04 | 卡夫食品有限公司 | Method for making reduced calorie peanut products |
| CN1219850A (en) * | 1996-04-29 | 1999-06-16 | 普罗克特和甘保尔公司 | Process for preparing improved oven-finished French fried potato strips |
| CN1220581A (en) * | 1996-05-02 | 1999-06-23 | 普罗克特和甘保尔公司 | Parfried food products containing low levels of free fatty acids and polymers |
| CN101919451A (en) * | 2009-06-16 | 2010-12-22 | 嘉里特种油脂（上海）有限公司 | Grease combination and application thereof |
| CN102524909A (en) * | 2010-12-31 | 2012-07-04 | 丰益(上海)生物技术研发中心有限公司 | Antibacterial composition containing erythritol fatty acid esters and preparation method and application of antibacterial composition |
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