CN103436360A - Method for producing glyceride compositions - Google Patents
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- CN103436360A CN103436360A CN2013102267775A CN201310226777A CN103436360A CN 103436360 A CN103436360 A CN 103436360A CN 2013102267775 A CN2013102267775 A CN 2013102267775A CN 201310226777 A CN201310226777 A CN 201310226777A CN 103436360 A CN103436360 A CN 103436360A
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Abstract
The invention provides a method for producing glyceride compositions and a method of reducing the content of at least one compound selected from a group consisting of fatty acid ester of glycidyl esters and fatty acid ester of trichloropropane-1,2-diol in the glyceride composition or inhibiting its production of the compound. The method for producing glyceride composition is characterized in that: the glyceride compositions are treated with deodorization process at 100-240 DEG Celsius, and the glyceride compositions contain at least one compound selected from a group composed of trichloropropane-1, 2-diol, fatty acid ester of trichloropropane-1, 2-diol, glycidyl esters, and fatty acid ester of glycidyl esters; and/or 3 mass % or more of diglyceride, wherein, before the deodorization process, in the deodorization process and/or after the deodorization process, the glyceride compositions are exposed in the acid environment by the method (1) that the glyceride compositions are allowed to contact with 0.01-10 mass % of phosphoric acid activated active carbon or 0.001-0.7 mass % of inorganic acid at 100-180 DEG Celsius.
Description
The application is to be dividing an application of September 3, application number in 2010 are 201010277986.9, denomination of invention is " glyceride composition and preparation method thereof " patent application the applying date, and its full content is hereby expressly incorporated by reference
Technical field
The present invention relates to a kind of glyceride composition, glyceride composition the preparation method, reduce in glyceride composition and be selected from fatty acid ester and 3-chloropropane-1 by Racemic glycidol, the method of the content of at least one compound in the group that the fatty acid ester of 2-glycol forms and inhibition are selected from fatty acid ester and 3-chloropropane-1 by Racemic glycidol, the method for the generation of at least one compound in the group that the fatty acid ester of 2-glycol forms.
Background technology
In recent years, did various trials for the local flavor and the stability that improve grease.The reduction of the qualities such as the local flavor of grease and stability is relevant with various factors, has disclosed the method for reply various factors.For example, as the deteriorated smelly trial of frying oils fat of the generation that suppresses to follow the thermooxidizing resolvent, patent documentation 1 discloses a kind of method that makes in grease to contain as the xitix of antioxidant etc.According to this method, by the state with the aqueous solution adds in grease by grease insoluble organic acids such as xitix, and carry out processed under high temperature and high decompression, can make antioxidant be contained in grease, like this, even long-time use also is difficult to produce, to add thermal degradation when smelly.
Yet the chemical reactions such as polymerization, can occur in the known unstable chemcial property of the ethylene oxide structure as the ternary cyclic ethers and reactive high.And the 3-chloropropane class of being combined with halogen is easily reaction also.Although be trace in a part of glyceride composition but have the fatty acid ester as a kind of Racemic glycidol of the epoxide with such ethylene oxide structure, cause most probably the chemical transformation such as polymerization.And, the 3-chloropropane-1 that can derive from the fatty acid ester of Racemic glycidol, the fatty acid ester of 2-glycol also causes same chemical reaction most probably.Due to polymerization etc. and deteriorated grease can produce foam and offending smell when fried, avoid its existence as far as possible.
But the method for the interpolation antioxidant as patent documentation 1 can't reduce fatty acid ester or 3-chloropropane-1 of already present Racemic glycidol in grease, the fatty acid ester of 2-glycol.Fatty acid ester or 3-chloropropane-1 that in other existing methods, not yet report reduces the Racemic glycidol in grease, the concrete grammar of the fatty acid ester of 2-glycol, its research and development are expected always.
Patent documentation 1: No. 01/096506th, International Publication.
Summary of the invention
The present invention carries out in view of the above problems, purpose is to provide a kind of less fatty acid ester and 3-chloropropane-1 of selecting free Racemic glycidol of containing, the glyceride composition of at least one compound in the group that the fatty acid ester of 2-glycol forms, the preparation method of this glyceride composition, reduce fatty acid ester and 3-chloropropane-1 of selecting free Racemic glycidol in glyceride composition, the method of the content of at least one compound in the group that the fatty acid ester of 2-glycol forms, and the fatty acid ester and 3-chloropropane-1 that suppress to select free Racemic glycidol, the method of the generation of at least one compound in the group that the fatty acid ester of 2-glycol forms.
The present application people specially grinds for addressing the above problem repeatedly, discovery by carrying out the deodorization processing to glyceride composition at specific temperature, or further be exposed in sour environment, or deodorization is processed under the cold condition lower than typical temperature, or in the acid number of specialized range heat treated, can reduce fatty acid ester or 3-chloropropane-1 of the Racemic glycidol in glyceride composition, the fatty acid ester of 2-glycol, and, by same method, can expect to reduce Racemic glycidol or 3-chloropropane-1 with identical functional group, the fatty acid ester of 2-glycol, thereby completed the present invention, wherein, described glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms, and/or contain in mass triglyceride more than 3%.The present invention is specific as follows.
(1) a kind of preparation method of glyceride composition, it is characterized in that: under the temperature condition of 100 ℃～240 ℃, glyceride composition is carried out to the deodorization processing, above-mentioned glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms and contain in mass the triglyceride more than 3%, perhaps above-mentioned glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms or contain in mass the triglyceride more than 3%.
(2) according to the preparation method of (1) described glyceride composition, it is characterized in that, above-mentioned glyceride composition contains fatty acid ester and 3-chloropropane-1 of selecting free Racemic glycidol, at least one in the group that the fatty acid ester of 2-glycol forms.
(3) according to the preparation method of (1) or (2) described glyceride composition, it is characterized in that, above-mentioned glyceride composition is treated oil.
(4) according to the preparation method of the described glyceride composition of any one in (1)～(3), it is characterized in that, the acid number of above-mentioned glyceride composition is 2～30, before above-mentioned deodorization is processed, above-mentioned glyceride composition is carried out to heat treated.
(5) according to the preparation method of the described glyceride composition of any one in (1)～(3), it is characterized in that, before above-mentioned deodorization is processed, above-mentioned glyceride composition is exposed in sour environment.
(6) according to the preparation method of the described glyceride composition of any one in (1)～(3), it is characterized in that, after above-mentioned deodorization is processed, above-mentioned glyceride composition is exposed in sour environment.
(7) according to the preparation method of (5) or (6) described glyceride composition, it is characterized in that, above-mentioned being exposed in sour environment is to make above-mentioned glyceride composition contact acid processing aid.
(8) according to the preparation method of (7) described glyceride composition, it is characterized in that, above-mentioned acid processing aid is at least one in the group of selecting free atlapulgite, acid gac and mineral acid to form.
(9) according to the preparation method of (8) described glyceride composition, it is characterized in that, above-mentioned mineral acid is at least one in the group of selecting free sulfuric acid, phosphoric acid, nitric acid and hydrochloric acid to form.
(10) according to the preparation method of the described glyceride composition of any one in (5)～(9), it is characterized in that, above-mentioned being exposed in sour environment carried out under 20 ℃～260 ℃.
(11) glyceride composition that in a kind of basis (1)～(10), the described preparation method of any one obtains.
(12) a kind of glyceride composition, it is characterized in that: contain in mass the triglyceride more than 3%, and contain with 3-chloropropane-1,2-glycol conversion amount meter adds up to content to be less than the free 3-chloropropane-1 of choosing of 10ppm, 2-glycol, 3-chloropropane-1, at least one in the group that the fatty acid ester of the fatty acid ester of 2-glycol, Racemic glycidol and Racemic glycidol forms.
(13) food of a kind of containing (11) or (12) described glyceride composition.
(14) a kind of fatty acid ester and 3-chloropropane-1 of selecting free Racemic glycidol of reducing in glyceride composition, at least one in the group that the fatty acid ester of 2-glycol forms or suppress the method for its generation, aforesaid method is characterised in that, under the temperature condition of 100 ℃～240 ℃, above-mentioned glyceride composition is carried out to the deodorization processing, above-mentioned glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms and contain in mass the triglyceride more than 3%, perhaps above-mentioned glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms or contain in mass the triglyceride more than 3%.
(15) according to fatty acid ester and 3-chloropropane-1 of selecting free Racemic glycidol in (14) described minimizing glyceride composition, at least one in the group that the fatty acid ester of 2-glycol forms or suppress the method for its generation, aforesaid method is characterised in that, glyceride composition is exposed in sour environment, carry out the deodorization processing under the temperature condition of 100 ℃～240 ℃, above-mentioned glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms and contain in mass the triglyceride more than 3%, perhaps above-mentioned glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms or contain in mass the triglyceride more than 3%.
According to the present invention, can obtain less fatty acid ester and 3-chloropropane-1 of selecting free Racemic glycidol of containing, the glyceride composition of at least one compound in the group that the fatty acid ester of 2-glycol forms.
Embodiment
Below, describe embodiments of the present invention in detail.In the present invention, to be lipid acid be combined on glycerine and form with 1～3 ester bond glyceryl ester, and except the main component triglyceride level (triglyceride) of grease, it also should comprise triglyceride (diacylglycerol), monoglyceride (monoester acyl glycerine).
The preparation method of glyceride composition of the present invention is characterised in that: under the temperature condition of 100 ℃～240 ℃, glyceride composition is carried out to the deodorization processing, described glyceride composition contains and selects free 3-chloropropane-1,2-glycol (hereinafter referred to as 3-MCPD), 3-chloropropane-1, at least one in the group that the fatty acid ester of the fatty acid ester of 2-glycol (hereinafter referred to as the 3-MCPD fatty acid ester), Racemic glycidol and Racemic glycidol forms, and/or contain in mass the triglyceride more than 3%.That is, in the preparation method of glyceride composition of the present invention, the glyceride composition of at least one in the group that (A) contained to the fatty acid ester composition that selects free 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol; (B) contain in mass the glyceride composition of the triglyceride more than 3%; Or any one glyceride composition that (C) contains at least one in the group that the fatty acid ester that selects free 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol forms and contain in mass the glyceride composition of the triglyceride more than 3% carries out the deodorization processing under 100 ℃～240 ℃ temperature condition.If the glyceride composition before above-mentioned deodorization is processed is the triglyceride contained in mass more than 3%, more preferably the content of triglyceride in mass 10%～98%, more preferably in mass 60%～93%.Here, the diglyceride content of glyceride composition can utilize vapor-phase chromatography (AOCS Offical Method Cd 11b-91) to measure.
And if the glyceride composition before above-mentioned deodorization is processed is at least one in the group that contains the fatty acid ester composition that selects free 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol, utilize the aftermentioned method in 3-MCPD conversion amount, more than the preferred 3ppm of total content of the fatty acid ester of the 3-MCPD in glyceride composition, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol, more preferably more than 10ppm, further preferred 10ppm～200ppm, most preferably 10ppm～100ppm.In addition, the preparation method of glyceride composition of the present invention has the fatty acid ester of minimizing Racemic glycidol and the effect of 3-MCPD fatty acid ester, therefore, if at least one compound contained in above-mentioned glyceride composition in the group that the fatty acid ester that selects free Racemic glycidol and 3-MCPD fatty acid ester form is just more effective.
And, although the fatty acid ester of structure and Racemic glycidol and the similar Racemic glycidol of 3-MCPD fatty acid ester and 3-MCPD are not included in common food oils, the preparation method of glyceride composition of the present invention also has the effect that reduces Racemic glycidol and 3-MCPD.
In the present invention, content assaying method as fatty acid ester, 3-MCPD and the 3-MCPD fatty acid ester of Racemic glycidol, Racemic glycidol, used the German official method (DGF Standard Methods C-III 18 (09)) of above-mentioned substance being measured in 3-MCPD conversion amount.
Specifically, gather oil sample and add internal standard substance, then adding therein the methanol solution of sodium methylate, making it at room temperature to react, carrying out the saponification of ester and decompose.Then, add and mix containing after the salt solution and hexane of acetate in minute, then removing hexane.Now, the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol, Racemic glycidol all is converted into 3-MCPD.Afterwards, derivative with phenylo boric acid, use hexane extraction, use the gas chromatography mass analytical equipment to measure.Then, the ionic strength of the relatively interior mark of the color atlas that uses gas chromatography mass analytical equipment mensuration to obtain and 3-MCPD, like this, just can calculate fatty acid ester, the 3-MCPD of Racemic glycidol in grease, Racemic glycidol, the total amount of 3-MCPD fatty acid ester by free 3-MCPD.
Like this, in the modulator approach of above-mentioned German official method working sample, the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol, Racemic glycidol all is converted into 3-MCPD.Therefore, the value of utilizing German official method to measure has just become the 3-MCPD scaled value of total content of the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol, Racemic glycidol.In addition, because determinand is plant wet goods glyceride composition, the material that the German official of the above-mentioned use of deducibility method is measured is fatty acid ester and the 3-MCPD fatty acid ester of Racemic glycidol.
The preparation method of glyceride composition of the present invention is characterised in that the glyceride composition of any one in above-mentioned (1)～(3) is carried out to the deodorization processing under the temperature condition of 100 ℃～240 ℃ of 240 ℃～260 ℃ low of the deodorization temperatures used than common oil and fat preparation method, temperature is preferably 100 ℃～235 ℃, more preferably 160 ℃～225 ℃, most preferably be 200 ℃～215 ℃.In addition, from preparing the also aspect of good glyceride composition of local flavor, the preparation method of glyceride composition of the present invention preferably, after the wet distillation of 240 ℃～260 ℃ is processed (common deodorization processing), carries out the deodorization processing at the temperature condition of 100 ℃～240 ℃.Condition beyond deodorization temperature is not particularly limited, still, preferably reduces pressure or be blown into water vapour, more preferably under reduced pressure be blown into water vapour.And preferably deodorization time is at 15～150 minutes, more preferably at 40～100 minutes.
In the preparation method of glyceride composition of the present invention, above-mentioned glyceride composition also can be used treated oil.By using treated oil, can prepare the better glyceride composition of local flavor.For treated oil, for example can use refining according to a conventional method rapeseed oil, soybean oil, rice bran oil, Thistle oil, raisin seed oil, Trisun Oil R 80, wheatgerm oil, Semen Maydis oil, Oleum Gossypii semen, sesame oil, peanut oil, oleum lini, perilla oil, sweet oil, plam oil and coconut wet goods vegetables oil; The two or more mixed oils that mix of above-mentioned vegetables oil; Or the super liquid oil of the palm olein oil, palm stearin, the palm that are put forward by above-mentioned plant oil content and palm middle distillate decile are carried edible oil; The winterized stearin of above-mentioned vegetables oil and transesterify wet goods; And this edible oil directly prepared by esterification of Triglycerides,C8-10.The process for purification of vegetables oil has chemical refining (chemical refining) and physics refining (physical refining), and wherein any process for purification can in use.The former chemical refining is the method usually adopted in vegetables oil refining, squeezing from material plant, the crude oil after extracting through degumming process, depickling process, decolouring processing, dewaxing treatment and deodorization processing etc. and made with extra care, become treated oil.And the latter's physics refining be the refining upper method of often using of plam oil and coconut wet goods, from the crude oil of the squeezings such as raw material palm and coconut through degumming process, decolouring process, deacid-deodoring processing and being made with extra care, become treated oil.
In the preparation method of glyceride composition of the present invention, preferably before carrying out above-mentioned deodorization processing, the above-mentioned glyceride composition that is 2～30 by acid number carries out heat treated.Glyceride composition after the above-mentioned glyceride composition that acid number is 2～30 can be used original acid number with regard to high glyceride composition and acid adding adjustment acid number, preferably used the above-mentioned glyceride composition that acid number is 2～15.In addition, the acid of using when adjusting acid number is free fatty acids preferably.Here so-called free fatty acids refers to free fatty acids and salt thereof.Be not particularly limited for free fatty acids, still, preferably use the lipid acid of carbon number 12～22, such as enumerating palmitinic acid, oleic acid, linolic acid, stearic acid and linolenic acid etc.
Preferably 100 ℃～260 ℃ of temperature during heat treated, more preferably 160 ℃～245 ℃, further preferably 200 ℃～225 ℃.In the preparation method of glyceride composition of the present invention, so-called heat treated, as long as heat, there is no other special restrictions, but particularly, can list simple heating, the lower heating of decompression, limit be blown into the heating of water vapour limit and under reduced pressure limit be blown into the heating means such as water vapour limit heating.For the condition beyond temperature, there is no particular restriction, but preferably reduce pressure or be blown into water vapour, more preferably under the decompression, is blown into water vapour.And there is no particular restriction for time of heat treated, but preferably 40～100 minutes.
In the preparation method of glyceride composition of the present invention, also can, before above-mentioned deodorization is processed or after above-mentioned deodorization processing, above-mentioned glyceride composition be exposed in sour environment.From the local flavor this point, preferably before deodorization is processed, be exposed to sour environment, and if be exposed to sour environment after deodorization is processed in, fatty acid ester, 3-chloropropane-1 of reducing Racemic glycidol, on the 2-glycol, effect is high.In the preparation method of glyceride composition of the present invention, for the method that above-mentioned glyceride composition is exposed to sour environment, there is no particular restriction, such as enumerating the method that makes above-mentioned glyceride composition contact acid processing aid and add organic acid method that carbon number is 1～22 etc. in above-mentioned glyceride composition, also can and with more than two kinds of aforesaid method.
And, be exposed in sour environment and preferably carry out under 20 ℃～260 ℃.If make it to contact the method for acid processing aid, be more preferably at 20 ℃～200 ℃ and carry out, most preferably at 100 ℃～180 ℃.Add if adopt the organic acid method that carbon number is 1～22, be more preferably at 100 ℃～260 ℃ and carry out, most preferably carry out at 180 ℃～260 ℃.
Make during above-mentioned glyceride composition contacts the method for acid processing aid, for acid processing aid, there is no particular restriction, such as enumerating: be acid processing aid, the aqueous solution and be the processing aid of acid processing aid, interior acid gas-containing and sour residual processing aid etc.Specifically can enumerate carclazyte, gac, silica gel, ion exchange resin, flocculating aids, zeolite, fiber, catalyzer, enzyme, above-mentioned auxiliary agent is carried out to auxiliary agent after acid treatment and mineral acid etc., these auxiliary agents both can be used alone and also can share.In the present invention, so-called carclazyte refers to and take montmorillonite as main clay.To carclazyte, there is no particular restriction, comprises acidic white earth or as atlapulgite any of the acidic white earth that is subjected to activation.In the present invention, so-called gac raw material can be used such as coke, synthetic graphite, charcoal, bone black, glass carbon, carbon fiber, carbon black and silk etc.Particularly preferably timber, kind skin, cereal residue, bark and coconut handle etc. derive from the gac raw material of plant, most preferably timber.The activation method of gac raw material is known several different methods such as steam activation, gas activation and chemical activation, with the raw material of any activation method activation wherein, all is suitable for using.Preferred chemical activation in above-mentioned activation method.In chemical activation method, more preferably use the activation such as zinc chloride, phosphoric acid and calcium chloride, most preferably use phosphoric acid activation.And, even the gac raw material of alkali activation is acidity and also is suitable for using if be treated to afterwards.In the present invention, so-called flocculating aids can be used diatomite, Mierocrystalline cellulose and perlite etc.Fiber can be used man-made fiber, vegetable fibre and animal fibre etc.In these processing aids, acid processing aid preferred acidic carclazyte of the present invention or acid gac, be more preferably and share acidic white earth and acid gac.There is no particular restriction for the addition of processing aid, but if the processing aid beyond mineral acid is preferably 0.01%～10% with respect to glyceride composition in mass, more preferably 1%～7%.Processing aid beyond mineral acid is generally solid, preferably makes it to contact rear filtration and removes.
In using the method for mineral acid as acid processing aid, to the kind of mineral acid, there is no particular restriction, such as enumerating sulfuric acid, phosphoric acid, nitric acid and hydrochloric acid etc., above-mentioned acid can be used separately or mixed and use.In above-mentioned mineral acid, sulfuric acid, phosphoric acid, nitric acid and the hydrochloric acid this point that is easy to get calmly considers it is preferred.And, preferably to above-mentioned glyceride composition, add mineral acid and use, but because addition is few, so, from controlling the addition aspect, preferably mineral acid is added with the aqueous solution.Preferably after just completing deodorization and processing and the temperature of above-mentioned glyceride composition add inorganic aqueous acid to above-mentioned glyceride composition while reaching more than 100 ℃, more preferably at 100 ℃～200 ℃.There is no particular restriction for the addition of mineral acid, with respect to glyceride composition, is preferably 0.001%～0.7% in mass, is more preferably 0.001%～0.05%.After mineral acid is added and contacting, preferably by washing, wait and remove mineral acid.
At the organic acid carbon number 1～22, add in the method for above-mentioned glyceride composition, to organic acid, there is no particular restriction, such as enumerating Citric Acid, acetic acid, oxysuccinic acid, lauric acid, tetradecanoic acid, palmitinic acid, stearic acid, twenty diacid, oleic acid, linoleic acid plus linolenic acid etc., above-mentioned acid can be used alone or as a mixture.In above-mentioned acid, from favorable solubility this point grease, the lipid acid such as preferred lauric acid, tetradecanoic acid, palmitinic acid, stearic acid, twenty diacid, oleic acid, linoleic acid plus linolenic acid.And, from improving dispersed aspect, preferably with the state of the aqueous solution, add the water-soluble organic acid of the crystallized forms such as Citric Acid and oxysuccinic acid.Preferably after processing just end, deodorization adds aqueous solutions of organic acids to above-mentioned glyceride composition.The temperature of above-mentioned glyceride composition, preferably more than 100 ℃, is more preferably 100 ℃～260 ℃, most preferably is 180 ℃～260 ℃.To the organic acid addition, there is no particular restriction, preferably reaches 10ppm～20% with respect to glyceride composition in mass, is more preferably the acid number that is added into glyceride composition and reaches 2～30.And, after being exposed to sour environment, preferably to the organic acid of carbon number 1～4, adopt filtration or washing to remove, the means such as the organic acid employing distillation to carbon number more than 5 are removed.
Glyceride composition of the present invention is characterised in that it is that the preparation method of the glyceride composition by the invention described above obtains.Utilize glyceride composition of the present invention can reduce fatty acid ester, 3-MCPD fatty acid ester, Racemic glycidol, the 3-MCPD of Racemic glycidol, maybe can suppress the generation of fatty acid ester and the 3-MCPD fatty acid ester of Racemic glycidol, so, can expect when fried with resulting glyceride composition to be difficult for producing foam and local flavor is difficult for variation.
Glyceride composition of the present invention is characterised in that: contain in mass the triglyceride more than 3%, and, in 3-MCPD conversion amount, the total content of at least one in the group of selecting the fatty acid ester of free 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol to form is no more than 10ppm.Although glyceride composition of the present invention contains a certain amount of above triglyceride, because of the fatty acid ester containing Racemic glycidol and Racemic glycidol less, so can expect when fried to be difficult for the generation foam and local flavor is difficult for variation.In addition, the content of preferably glycerine diester is in mass 60%～98%, and in 3-MCPD conversion amount, and the total content of at least one in the group of selecting the fatty acid ester of free 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol to form is less than 3ppm.
Food of the present invention is characterised in that the glyceride composition that comprises the invention described above.Because fatty acid ester and the 3-MCPD fatty acid ester of the Racemic glycidol in the glyceride composition used as raw material are less, so utilize food of the present invention to be difficult in advance producing foam when fried and local flavor is difficult for variation.As food likely contain grease food all may become object.For example flavor oil, mayonnaise, chocolate, sauce, oleomargarine, edible fat spread and milk wet goods.
Method of the present invention is the method that reduces the content of at least one compound in the group that the fatty acid ester that selects free Racemic glycidol in glyceride composition and 3-MCPD fatty acid ester form or suppress its generation.The method is by glyceride composition is carried out to the deodorization processing under 100 ℃～240 ℃ temperature condition, thereby the fatty acid ester of the Racemic glycidol in the minimizing glyceride composition/or the content of the fatty acid ester of 3-MCPD or suppress its generation, wherein, described glyceride composition contains at least one in the group that the fatty acid ester that selects free 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol forms, and/or contains in mass the glyceride composition of the triglyceride more than 3%.The condition that deodorization is processed is identical with the preparation method of above-mentioned glyceride composition.In addition, by above-mentioned glyceride composition is exposed in sour environment, further under 100 ℃～240 ℃ temperature condition, deodorization is processed, and can further reduce at least one compound in the group that the fatty acid ester that selects free Racemic glycidol and 3-MCPD fatty acid ester form or further suppress its generation.
[embodiment]
Embodiments of the invention are described in more detail below, and the present invention is not subject to any restriction of these records.
Possibility to the fatty acid ester that reduces the 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and the Racemic glycidol that contain in glyceride composition is discussed.
The research of the exposure condition under<sour environment >
[raw material glyceride composition 1]
Add fatty acid ester (the Racemic glycidol stearate of 0.256g Racemic glycidol in utilizing refining soybean vegetable seed mixing treated oil (mixing oil of soybean bleached oil and the vegetable seed bleached oil) 1600g of ordinary method; Tokyo HuaCheng Industry Co., Ltd's system) and the 3-MCPD fatty acid ester of 0.192g (1-stearyl--3-chloropropane glycol; Wako Pure Chemical Industries, Ltd.'s system), obtain raw material glyceride composition 1(after mixing and count 85.35ppm with 3-MCPD conversion amount).
[comparative example 1]
By raw material glyceride composition 1 under reduced pressure 110 ℃ stir 20 minutes, obtain the glyceride composition of comparative example 1.
[embodiment 1]
Add in mass 5% gac (the phosphoric acid activation gac: CA1 with respect to the amount of this raw material glyceride composition 1 in raw material glyceride composition 1, Japan NORIT Co., Ltd. system), under reduced pressure 110 ℃ were stirred after 20 minutes, filter and remove gac, obtain the glyceride composition of embodiment 1.
[embodiment 2]
Except using in mass 5% atlapulgite (vitriolization carclazyte: Suisawa Chemical Industry Co., Ltd.'s system) replace 5% gac, obtain the glyceride composition of embodiment 2 by method similarly to Example 1.
[embodiment 3]
Add in mass 5% atlapulgite (the vitriolization carclazyte: Suisawa Chemical Industry Co., Ltd.'s system) with respect to the amount of this raw material glyceride composition 1 in raw material glyceride composition 1, after under reduced pressure normal temperature (28 ℃) stirs 20 minutes, filter and remove atlapulgite, obtain the glyceride composition of embodiment 3.
[raw material glyceride composition 2]
Raw material glyceride composition 1 and soybean bleached oil are mixed with weight ratio 83:17, obtain raw material glyceride composition 2(and count 14.30ppm with 3-MCPD conversion amount).
[embodiment 4]
Add in mass 5% gac (the phosphoric acid sensitization gac: CA1 with respect to the amount of this raw material glyceride composition 2 in raw material glyceride composition 2, Japan NORIT Co., Ltd. system), under decompression 110 ℃ stir 20 minutes after, filter and remove gac, obtain the glyceride composition of embodiment 4.
[embodiment 5]
Except using in mass 5% atlapulgite (vitriolization carclazyte: Suisawa Chemical Industry Co., Ltd.'s system) replace 5% gac, obtain the glyceride composition of embodiment 5 by method similarly to Example 4.
[raw material glyceride composition 3]
Raw material glyceride composition 1 and soybean bleached oil are mixed with weight ratio 86:14, obtain raw material glyceride composition 3(and count 11.65ppm with 3-MCPD conversion amount).
[embodiment 6]
Add in mass 5% gac (the phosphoric acid sensitization gac: CA1 with respect to the amount of this raw material glyceride composition 3 in raw material glyceride composition 3, Japan NORIT Co., Ltd. system), under decompression 110 ℃ stir 20 minutes after, filter and remove gac, obtain the glyceride composition of embodiment 6.
[embodiment 7]
Except using in mass 5% atlapulgite (vitriolization carclazyte: Suisawa Chemical Industry Co., Ltd.'s system) replace 5% gac, obtain the glyceride composition of embodiment 7 by method similarly to Example 6.
(quantitative method)
Quantitatively carrying out according to German official method (DGF Standard Methods C-III 18 (09)) of the fatty acid ester of the 3-MCPD in glyceride composition, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol.In the method, due to modulation during working sample fatty acid ester and the 3-MCPD fatty acid ester of Racemic glycidol be converted to 3-MCPD, so the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol is all measured as free 3-MCPD.
Add the internal standard substance (3-MCPD-d5 20 μ g/mL solution) of 50 μ L in the sample 100mg of raw material glyceride composition 1～3, embodiment 1～7 and comparative example 1 after, the sodium methoxide solution (0.5mol/L methyl alcohol) that adds therein 1mL, make it at room temperature to react, carry out the saponification of ester and decompose.Subsequently, add 3mL to contain the salt solution (20%) of acetate in minute, after mixing, remove hexane.Then, add and mix containing after the 3mL salt solution (20%) and 3mL hexane of acetate in minute, then removing hexane.Now, Racemic glycidol is converted to 3-MCPD, and the fatty acid ester of Racemic glycidol is converted to 3-MCPD when ester bond disconnects.Then, utilize the phenylo boric acid aqueous solution (25%) of 250 μ L derivative, use the 2mL hexane extraction, measure with the gas chromatography mass analytical equipment.
The color atlas that utilizes the mensuration of above-mentioned gas chromatography mass analytical equipment to obtain, relatively as the ionic strength of interior target 3-MCPD-d5 and 3-MCPD, then calculate fatty acid ester, the 3-MCPD of Racemic glycidol in glyceride composition, Racemic glycidol, the total amount of 3-MCPD fatty acid ester by being converted into free 3-MCPD.
(GC-MS analysis condition)
Analytical equipment: Agilent Technology company system, type 6890GC
Cylinder: Restek company system, the long 30m of ProductName Rtx-5MS(, diameter 0.25mm)
Column temperature: 60 ℃ (1 minute)～190 ℃ (6 ℃/minutes of heat-up rates)～280 ℃ (20 ℃/minutes of heat-up rates)
Detector: MS(EI, the SIM pattern)
Non-shunting: inject 1 μ L
Carrier gas: He
Table 1
Proved by the gac of use mineral acid activation and the carclazyte of vitriolization and processed, the total amount of the fatty acid ester of the 3-MCPD in glyceride composition, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol (3-MCPD conversion amount) significantly reduces (table 1: embodiment 1～7, raw material glyceride composition 1～3, comparative example 1).In addition, consider the amount of fatty acid ester and the 3-MCPD of the Racemic glycidol added in glyceride composition, the fatty acid ester of Racemic glycidol and the minimizing of 3-MCPD are clearly.
[raw material glyceride composition 4]
Add fatty acid ester (the Racemic glycidol stearate of the Racemic glycidol of 20.8mg in utilizing refining soybean vegetable seed mixing oil (mixing oil of soybean bleached oil and the vegetable seed bleached oil) 160g of ordinary method; Tokyo HuaCheng Industry Co., Ltd's system) and the 3-MCPD fatty acid ester of 16.0mg (1-stearyl--3-chloropropane glycol; Wako Pure Chemical Industries, Ltd.'s system), obtain raw material glyceride composition 4(after mixing and count 70.61ppm with 3-MCPD conversion amount).
<acid-treated research >
[embodiment 8]
For raw material glyceride composition 4, add in mass with respect to its sulfuric acid of 0.025%, under normal pressure, 150 ℃ are stirred 10 minutes, obtain the glyceride composition of embodiment 8.
Table 2
Proved that the total amount (3-MCPD conversion amount) of utilizing sulfuric acid to carry out the fatty acid ester of its 3-MCPD of acid-treated glyceride composition, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol significantly reduces (table 2: embodiment 8).In addition, consider the amount of fatty acid ester and the 3-MCPD fatty acid ester of the Racemic glycidol added in glyceride composition, both reductions are clearly.
The research of<deodorization condition >
[embodiment 9]
To the glyceride composition of raw material glyceride composition 1 while be blown into water vapour (total amount: in mass with respect to the glyceride composition amount 3%) under reduced pressure (4torr) 210 ℃ of deodorizations 90 minutes, obtain the glyceride composition of embodiment 9.
Table 3
Calculate 3-MCPD conversion amount according to the quantitative method of above-mentioned record.Proof is processed the total amount (table 3: embodiment 9) of the fatty acid ester that has reduced 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol by carrying out at low temperatures deodorization.
The research of<deodorization condition and acid number and heat treated condition >
The glyceride composition that modulation contains a large amount of triglycerides, by processing with atlapulgite, can modulate the sample that the total content of the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol reduces.Then, studied the temperature of heat treated and had or not the interpolation free fatty acids to suppress on the generation of the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol the impact produced.
[raw material glyceride composition 5]
Mixing oil with lipase to refining according to a conventional method soybean bleached oil and vegetable seed bleached oil carries out partial hydrolysis and carries out molecular distillation.Further at 250 ℃ of lower deodorizations glyceride composition of 1.5 hours, adding 5% atlapulgite (V2F in mass, the vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, remove by filter atlapulgite, obtaining that raw material glyceride composition 5(glyceryl ester forms is mono-glycerides 0.6%, triglyceride 88.7% and triglyceride level 10.7% by weight, with 3-MCPD conversion amount, counts 0.76ppm).
[embodiment 10]
Acid number by glyceride composition 5(glyceride composition: 0.2) under normal pressure 220 ℃ process 90 minutes, obtain the glyceride composition of embodiment 10.
[embodiment 11]
Except the acid number for making glyceride composition reaches 5.8, add palmitinic acid, employing method similarly to Example 10 obtains the glyceride composition of embodiment 11.
[embodiment 12]
Except the acid number for making glyceride composition reaches 10.9, add palmitinic acid, employing method similarly to Example 10 obtains the glyceride composition of embodiment 12.
[embodiment 13]
Except temperature is reached 230 ℃, employing method similarly to Example 10 obtains the glyceride composition of embodiment 13.
[embodiment 14]
Except temperature is reached 230 ℃, employing method similarly to Example 11 obtains the glyceride composition of embodiment 14.
[embodiment 15]
Except temperature is reached 230 ℃, employing method similarly to Example 12 obtains the glyceride composition of embodiment 15.
[comparative example 2]
Except temperature is reached 240 ℃, employing method similarly to Example 10 obtains the glyceride composition of comparative example 2.
[embodiment 16]
Except temperature is reached 240 ℃, employing method similarly to Example 11 obtains the glyceride composition of embodiment 16.
[embodiment 17]
Except temperature is reached 240 ℃, employing method similarly to Example 12 obtains the glyceride composition of embodiment 17.
Table 4
Calculate 3-MCPD conversion amount according to the quantitative method of above-mentioned record.The more low total amount (3-MCPD conversion amount) (table 3: raw material glyceride composition 5, embodiment 10～17, comparative example 2) that more can suppress the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol of temperature in heat treated.When carrying out deodorization and process such pyroprocessing, add palmitinic acid for making acid number reach 5.8 or 10.9, proved that so, along with high temperature, the generation of the fatty acid ester of 3-MCPD, 3-MCPD fatty acid ester, Racemic glycidol and Racemic glycidol is significantly inhibited (table 3: embodiment 10～12, embodiment 13～15, comparative example 2 and embodiment 16～17).
[raw material glyceride composition 6]
With lipase, the rice bran oil extracted is according to a conventional method carried out to partial hydrolysis, after depickling, in mass the rice bran oil of this depickling added to 2% atlapulgite (V2F, the vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 105 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained the rice bran oil of decolouring.Then, while the rice bran oil of this decolouring is blown into under reduced pressure (4torr) 240 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain treated oil (raw material glyceride composition 6).In addition, utilizing vapor-phase chromatography (AOCS Official Method Cd 11b-91) to measure diglyceride content in raw material glyceride composition 6 is in mass 7%.
[reference example 1]
In mass raw material glyceride composition 6 is added to 0.1% atlapulgite (V2F, the vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filter and remove atlapulgite, obtain again bleached oil (glyceride composition of reference example 1).
[embodiment 18]
In mass raw material glyceride composition 6 is added to 0.5% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 240 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 18.
[embodiment 19]
In mass raw material glyceride composition 6 is added to 0.5% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 230 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 19.
[embodiment 20]
In mass raw material glyceride composition 6 is added to 1% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 220 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 20.
[embodiment 21]
In mass raw material glyceride composition 6 is added to 1% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 200 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 21.
Table 5
※ reference example 1 local flavor is slightly poor, embodiment 18～21 excellent flavors.
Calculate 3-MCPD conversion amount according to the quantitative method of above-mentioned record.Proved that embodiment 18～21 can reduce the 3-MCPD conversion amount in treated oil, also can make with extra care out sapid edible oil.In addition, then deodorization temperature is lower, and the effect that reduces 3-MCPD conversion amount is better, and the atlapulgite amount while decolouring again in mass is if 0.5%, and the effect that reduces 3-MCPD conversion amount is remarkable.
[raw material glyceride composition 7]
The glyceride composition of 85% vegetable seed bleached oil (the Nisshin Oil Mills, Ltd's system) in mass and 15% 5 is mixed, the mixing oil that obtains, while being blown under reduced pressure (4torr) 240 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, is obtained to treated oil (raw material glyceride composition 7).The diglyceride content of measuring in raw material glyceride composition 7 by vapor-phase chromatography (AOCS OfficiAl MethoD CD 11b-91) is 13.3% in mass.
[reference example 2]
In mass raw material glyceride composition 7 is added to 0.1% atlapulgite (V2F, the vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filter and remove atlapulgite, obtain again bleached oil (glyceride composition of reference example 2).
[embodiment 22]
In mass raw material glyceride composition 7 is added to 0.5% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 240 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 22.
[embodiment 23]
In mass raw material glyceride composition 7 is added to 0.5% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 230 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 23.
[embodiment 24]
In mass raw material glyceride composition 7 is added to 1% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 220 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 24.
[embodiment 25]
In mass raw material glyceride composition 7 is added to 1% atlapulgite (V2F, vitriolization carclazyte, Suisawa Chemical Industry Co., Ltd.'s system), under reduced pressure 110 ℃ were stirred after 20 minutes, filtered and removed atlapulgite, obtained bleached oil again.Then, while to this again bleached oil be blown under reduced pressure (4torr) 200 ℃ of deodorizations of water vapour (in mass to oil 3%) 90 minutes, obtain the glyceride composition of embodiment 25.
Table 6
※ reference example 2 local flavors are slightly poor, embodiment 22～25 excellent flavors.
Calculate 3-MCPD conversion amount according to the quantitative method of above-mentioned record.Proved that embodiment 22～25 can reduce the 3-MCPD conversion amount in treated oil, also can make with extra care out sapid edible oil.In addition, then deodorization temperature is lower, and the effect that reduces 3-MCPD conversion amount is better, if then the atlapulgite amount while decolouring be 0.5% in mass, the effect that reduces 3-MCPD conversion amount is remarkable.
Claims (4)
1. the preparation method of a glyceride composition, it is characterized in that, under the temperature condition of 100 ℃～240 ℃, glyceride composition is carried out to the deodorization processing, described glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms and contain in mass the triglyceride more than 3%, perhaps described glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms or contain in mass the triglyceride more than 3%, wherein,
Before described deodorization is processed, described deodorization process in and/or after described deodorization processes, the method by (1) is exposed to described glyceride composition in sour environment,
(1) make the contact of described glyceride composition 0.01%～10% phosphoric acid activation gac or 0.001%～0.7% mineral acid in mass in mass at 100 ℃～180 ℃.
2. the preparation method of glyceride composition according to claim 1, is characterized in that, described glyceride composition is treated oil.
3. the preparation method of glyceride composition according to claim 2, is characterized in that, described mineral acid is at least one in the group of selecting free sulfuric acid, phosphoric acid, nitric acid and hydrochloric acid to form.
4. a fatty acid ester that reduces in glyceride composition to select free Racemic glycidol and 3-chloropropane-1, at least one in the group that the fatty acid ester of 2-glycol forms or suppress the method for its generation, described method is characterised in that, under the temperature condition of 100 ℃～240 ℃, described glyceride composition is carried out to the deodorization processing, described glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms and contain in mass the triglyceride more than 3%, perhaps described glyceride composition contains and selects free 3-chloropropane-1, the 2-glycol, 3-chloropropane-1, the fatty acid ester of 2-glycol, at least one in the group that the fatty acid ester of Racemic glycidol and Racemic glycidol forms or contain in mass the triglyceride more than 3%, wherein,
Before described deodorization is processed, described deodorization process in and/or after described deodorization processes, the method by (1) is exposed to described glyceride composition in sour environment,
(1) make the contact of described glyceride composition 0.01%～10% phosphoric acid activation gac or 0.001%～0.7% mineral acid in mass in mass at 100 ℃～180 ℃.
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- 2010-09-03 CN CN201310226777.5A patent/CN103436360B/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102010786A (en) | 2011-04-13 |
| TW201108943A (en) | 2011-03-16 |
| CN102010786B (en) | 2014-05-07 |
| JP5973530B2 (en) | 2016-08-23 |
| JP2011074358A (en) | 2011-04-14 |
| JP2015045023A (en) | 2015-03-12 |
| TWI522044B (en) | 2016-02-21 |
| JP5700503B2 (en) | 2015-04-15 |
| CN103436360B (en) | 2015-04-22 |
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