CN108642097A - A kind of preparation method of three saturated fatty acid glycerides - Google Patents
A kind of preparation method of three saturated fatty acid glycerides Download PDFInfo
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Abstract
The present invention relates to glycerine Lipase absobed processing technique fields, and in particular to a kind of preparation method of three saturated fatty acid glycerides comprising：Glyceride containing saturated fatty acid residues, saturated fat bronsted lowry acids and bases bronsted lowry are subjected to catalysis reaction under the action of lipase, obtain three saturated fatty acid glyceride.The corresponding saturated fatty acid of wherein described saturated fatty acid residues is identical as the saturated fatty acid for participating in catalysis reaction, and the glyceride containing saturated fatty acid residues at least have there are one the ester bond or hydroxyl that are not combined with saturated fatty acid residues.On the basis of glyceride fraction has saturated fatty acid residues, sufficient amount of saturated fatty acid residues are provided by corresponding saturated fatty acid, and utilize the catalytic action of lipase so that its reaction condition is mild, side reaction is few, and the purity of three saturated fatty acid glycerides of generation is high.
Description
Technical field
The present invention relates to glycerine Lipase absobed processing technique fields, in particular to a kind of three saturated fatty acid glycerides
Preparation method.
Background technology
Three saturated fatty acid glyceride synthetic methods mainly have：Triglycerides is carried out under chemical catalyst effect random
Transesterification and glycerine are reacted with saturated fatty acid in high temperature (180 DEG C~200 DEG C).To glycerine three under chemical catalyst effect
The purity that ester carries out three saturated fatty acid glycerides of random transesterification preparation is not high.Glycerine and saturated fatty acid are in (180 DEG C of high temperature
~200 DEG C) reaction the shortcomings that be to react and need high temperature, technological reaction condition is harsh, and side reaction is more.
Invention content
The purpose of the present invention is to provide a kind of preparation method of three saturated fatty acid glycerides, enable to full to three
High with the purity of fatty glyceride, saturated fatty acid content is high on the positions sn-2, and reaction condition is simple, and side reaction is few.
The present invention solves its technical problem using following technical scheme to realize.
A kind of preparation method of three saturated fatty acid glyceride provided by the invention comprising：Saturated fatty acid will be contained
Glyceride, the saturated fat bronsted lowry acids and bases bronsted lowry of residue carry out catalysis reaction under the action of non-directional lipase, obtain three saturated fats
Acid glyceride.Wherein the corresponding saturated fatty acid of saturated fatty acid residues is identical as the saturated fatty acid for participating in catalysis reaction, and
Glyceride containing saturated fatty acid residues at least has that there are one the ester bonds or hydroxyl that are not combined with saturated fatty acid residues.
It is raw in situ by corresponding saturated fat bronsted lowry acids and bases bronsted lowry on the basis of glyceride fraction has saturated fatty acid residues
At Salt of saturated fatty acid sufficient amount of saturated fatty acid residues are provided, and using the catalytic action of non-directional lipase,
So that its reaction condition is mild, side reaction is few, and the purity of three saturated fatty acid glycerides of generation is high.
Specific implementation mode
It, below will be to embodiment party of the present invention to keep the purpose, technical scheme and advantage of embodiment of the present invention clearer
Technical solution in formula is clearly and completely described.The person that is not specified actual conditions in embodiment or embodiment, according to routine
The condition that condition or manufacturer suggest carries out.Reagents or instruments used without specified manufacturer, being can be by commercially available purchase
Buy the conventional products of acquisition.
The preparation method of three saturated fatty acid glycerides of embodiment of the present invention is specifically described below.
A kind of preparation method for three saturated fatty acid glyceride that some embodiments of the present invention provide comprising：It will
Glyceride containing saturated fatty acid residues, saturated fat bronsted lowry acids and bases bronsted lowry carry out catalysis reaction under the action of non-directional lipase,
Obtain three saturated fatty acid glycerides.
Wherein the corresponding saturated fatty acid of saturated fatty acid residues is identical as the saturated fatty acid for participating in catalysis reaction, example
Such as, glyceride is that palmitic acid residues (are not excluded for other types containing non-palmitic acid residues containing having plenty of saturated fatty acid residues
Saturated fatty acid residues), then corresponding reaction raw materials saturated fatty acid is palmitic acid.And it is residual containing saturated fatty acid
The glyceride of base at least has that there are one the ester bonds or hydroxyl that are not combined with saturated fatty acid residues.I.e. as the glyceride of raw material
Including at least one of monoglyceride, diglyceride and triglycerides, and its part ester bond is full with (above-mentioned specified)
Obtained ester bond is combined with aliphatic acid.For example, the glyceride can be monoglyceride, can also be diglyceride or glycerine
The mixture of three esters or diglyceride and triglycerides.
It should be noted that catalysis reaction includes ester exchange reaction and esterification, when glyceride is mainly triglycerides
When, the mainly ester exchange reaction of progress, when glyceride includes partial glycerol diester or monoglyceride, there is also esterifications.
On the basis of glyceride has the part ester bond of specific saturated fatty acid residues, by introducing specific saturated fat
Acid provides abundant fatty acid residue, so that transesterification and esterification can occurs under the catalysis of non-directional enzyme in it, into
And reduce reaction condition so that side reaction is few, and the purity of three saturated fatty acid glycerides of generation is high, saturated fat on the positions sn-2
Fat acid content is high.
According to some embodiments, the ratio of glyceride and saturated fatty acid be using saturated fatty acid as additive amount so that
Saturated fatty acid residues in reaction system account for the ratio of total fatty acid residue and are greater than or equal to 90%, preferably greater than
92%, more preferably greater than 95%.For example, addition saturated fatty acid can be made to make the saturated fatty acid residues in reaction system
The ratio for accounting for total fatty acid residue is 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97% or 98% etc..
According to some embodiments, the molar ratio of alkali and saturated fatty acid is not more than 1, it is preferable that alkali and aliphatic acid rub
You are than being not more than 0.025, it is further preferred that with aliphatic acid molar ratio is 0.025~0.001. to alkali
In some embodiments, alkali NaOH, KOH, NaOC2H5、KOC2H5、NaOCH3、KOCH3, solid base catalyst and
Its mixture, it is further preferred that the alkali is NaOH or KOH.
By the setting of the reactant ratio, can enable to fully to meet ester exchange reaction or esterification into
Row, and then enable to fully be contacted between reactant, obtain the higher reaction product of purity.
According to some embodiments, the additive amount of non-directional lipase is the 0.05~10% of glyceride, it is therefore preferable to 0.1
~8%, in further preferred scheme, the additive amount of Novozym 435 is the addition of 4~8%, Lipase DF " Amano " 15
The additive amount that the additive amount that amount is 0.1~1%, LipozymeTLIM is 4~8%, LipaseAY30G is 0.1~1%.For example,
The additive amount of non-directional lipase can be 0.05%, 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.
The additive amount of non-directional enzyme has reaction process important influence, and additive amount is too low to can not reach catalytic effect, adds
Dosage is excessively high then to make cost increase, and can influence the contact in reaction process between reactant to a certain extent, causes anti-
It answers ineffective.Therefore, the catalysis to reaction can be fully achieved by the additive amount of the non-directional lipase of above range
Effect so that reaction carries out more thorough in the reaction time fixed shortly.
In some embodiments, lipase includes at least one of non-directional lipase, orientation lipase, it is preferable that fat
Fat enzyme be non-directional lipase, non-directional lipase include Novozym 435, Lipase DF " Amano " 15,
At least one of LipozymeTLIM and LipaseAY30G.For example, non-directional lipase can be Novozym 435 or
Lipase DF " Amano " 15, can also Novozym 435 and Lipase DF " Amano " 15 mixture.Preferably, non-fixed
It is Lipase DF " Amano " 15 to lipase.
According to some embodiments, the temperature that is catalyzed reaction is 30~90 DEG C, preferably 35~85 DEG C, it is further preferred that
LipozymeTLIM reaction temperatures are 65~70 DEG C, and 435 reaction temperatures of Novozym are 75~85 DEG C, Lipase DF " Amano "
15 reaction temperatures are 35~40 DEG C, and LipaseAY30G reaction temperatures are 35~40 DEG C；The time of catalysis reaction is 0.5~9 small
When, the preferred reaction time is 1~4 hour.Under the reaction temperature, reaction temperature is anti-relative to traditional chemical catalyst
Answer temperature relatively low, reaction is more prone to carry out, and can keep reaction temperature constant by way of heating water bath, water-bath adds
It is heated relatively uniform for heat, and heat transfer effect is good, so that reaction is more prone to carry out.It is of course also possible to select furnace body
Other mode of heatings such as heating carry out maintaining reaction temperature.
According to some embodiments, participate in reaction raw material saturated fatty acid be selected from palmitic acid, stearic acid, octanoic acid, capric acid,
Lauric acid, myristic acid or arachidic acid also may be used for example, reactant can be glyceride and palmitate containing palmitic acid residues
To be the glyceride containing stearic acid residue and stearic acid salt, or the glyceride containing lauric acid residue and laruate.It is excellent
Select palmitic acid or stearic acid, more preferable palmitic acid.
The purpose that alkali is added in selection in embodiments of the present invention is that alkali can be raw in situ with the aliphatic acid in reaction system
At fatty acid salt, it is a kind of strong base-weak acid salt, and ionizing power is strong, and fatty acid residue activity is strong, provides fatty acid residue energy
Power is much larger than free fatty or aliphatic ester, to accelerate the rate of ester exchange reaction, shortens the reaction time, it is possible to reduce fat
Fat enzyme dosage, reduces cost.
According to some embodiments, the glyceride containing saturated fatty acid residues can be cocoa butter, coconut oil, palm kernel
Oil, the hard ester of palm oil or 58 degree of palm oils.Preferably, the glyceride containing saturated fatty acid residues is the hard ester of palm oil, palm
Oily hard ester is a kind of palm oil for the high-melting-point (44~56 DEG C of fusing point) that will produce during producing edible palm oil.
According to some embodiments, carries out catalysis reaction and specifically include the glyceride containing saturated fatty acid residues, satisfy
Lipase is added after being mixed with fatty bronsted lowry acids and bases bronsted lowry, under conditions of being passed through inert gas, is stirred reaction.Pass through inert gas
Protection it can be reacted to avoid outside air and impact, and stir and can fully connect between reactant
It touches so that reaction is more fully quickly.
In some embodiments, the rotating speed stirred when being reacted is 300~600r/min, preferably 400~500r/min.
In some embodiments, inert gas can select nitrogen, neon, argon gas etc., it is preferable that inert gas is nitrogen
Gas.
Further include solvent in reaction system according to some embodiments, can be made by the way that solvent is added in the reaction system
The object that can dissolve between being conducive to reactant in a solvent of reactant and reaction product mutually flows, play in reaction process
With good mass transfer effect, so that reaction effect is more preferable.Simultaneously after completion of the reaction, solvent can also carry out product
Extraction.Solvent can be added in reaction system together with reactant, can also be added gradually to reactant during the reaction
In system.In some embodiments, solvent is n-hexane.In some embodiments, the additive amount of solvent is the matter of raw materials glycerine ester
1~2 times of amount.
According to some embodiments, soap in organic phase is removed by silica gel absorption after catalysis reaction, then concentrated.Example
Such as, after it can be filtered after catalysis is reacted, then the soap in organic phase removed by silica gel absorption.
A kind of preparation method for tripalmitin that some embodiments of the present invention provide comprising：It will contain
Glyceride, the palm bronsted lowry acids and bases bronsted lowry of palmitic acid residues carry out catalysis reaction under the action of non-directional lipase, obtain three palmitic acids
Glyceride.It is wherein triglycerides as the glyceride of raw material.
In some embodiments, USU type triglycerides, such as 1,3- can also be synthesized with three saturated fatty acid glycerides
Two oleic acid -2- palmitic acids, three ester (OPO).
The feature and performance of the present invention are described in further detail with reference to embodiments.
Embodiment 1
Palmitic acid is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system account for
The ratio of total fatty acid residue is 90%, palmitic stearin 1000g and 1000ml n-hexane is put into four-hole boiling flask, water-bath
Heating mixes until after dissolving with palmitic acid and sodium methoxide.Wherein, the molar ratio of sodium methoxide and palmitic acid is 0.02.
Then, after being passed through nitrogen, under the conditions of bath temperature is 35 DEG C and rotating speed is 400r/min, add after being stirred until homogeneous
Enter 5g non-directional lipase Lipase DF " Amano " 15, insulated and stirred is reacted 4 hours.Centrifugation obtains organic phase supernatant, uses silicon
Glue is adsorbed and removed soap in organic phase, then molecular distillation removes free fatty and obtains faint yellow solid, tripalmitin
Content is that palmitic acid content is 88.5% on the positions 81.5%, sn-2.
Embodiment 2
Palmitic acid is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system account for
The ratio of total fatty acid residue is 92%, palmitic stearin 1000g and 1200ml n-hexane is put into four-hole boiling flask, water-bath
Heating mixes until after dissolving with palmitic acid and sodium hydroxide.Wherein, the molar ratio of sodium hydroxide and palmitic acid is 0.01.
Then, after being passed through nitrogen, under the conditions of bath temperature is 40 DEG C and rotating speed is 350r/min, add after being stirred until homogeneous
Enter 10g non-directional lipase LipaseAY30G, insulated and stirred is reacted 1 hour.Centrifugation obtains organic phase supernatant, uses silica gel absorption
Soap in organic phase is removed, then molecular distillation removes free fatty and obtains faint yellow solid, tripalmitin content is
Palmitic acid content is 90.5% on the position 81.3%, sn-2.
Embodiment 3
Palmitic acid is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system account for
The ratio of total fatty acid residue is 94%, palmitic stearin 1000g and 1500ml n-hexane is put into four-hole boiling flask, water-bath
Heating mixes until after dissolving with palmitic acid and potassium hydroxide.Wherein, the molar ratio of potassium hydroxide and palmitic acid is 0.025.
Then, after being passed through nitrogen, under the conditions of bath temperature is 85 DEG C and rotating speed is 500r/min, add after being stirred until homogeneous
Enter 50g non-directional lipase Novozym 435, insulated and stirred is reacted 1 hour.Centrifugation obtains organic phase supernatant, uses silica gel absorption
Soap in organic phase is removed, then molecular distillation removes free fatty and obtains faint yellow solid, tripalmitin content is
Palmitic acid content is 91.3% on the position 81.8%, sn-2.
Embodiment 4
Palmitic acid is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system account for
The ratio of total fatty acid residue is 94%, palmitic stearin 1000g and 1500ml n-hexane is put into four-hole boiling flask, water-bath
Heating mixes until after dissolving with palmitic acid and sodium ethoxide.Wherein, the molar ratio of sodium ethoxide and palmitic acid is 0.00125.
Then, after being passed through nitrogen, under the conditions of bath temperature is 65 DEG C and rotating speed is 400r/min, add after being stirred until homogeneous
Enter 40g non-directional Lipozyme TLIM, insulated and stirred is reacted 2 hours.Centrifugation obtains organic phase supernatant, uses silica gel absorption
Soap in organic phase is removed, then molecular distillation removes free fatty and obtains faint yellow solid, tripalmitin content is
Palmitic acid content is 93.1% on the position 85.1%, sn-2.
Embodiment 5
Palmitic acid is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system account for
The ratio of total fatty acid residue is 96%, palmitic stearin 1000g and 2000ml n-hexane is put into four-hole boiling flask, water-bath
Heating mixes until after dissolving with palmitic acid and potassium hydroxide.Wherein, potassium hydroxide and palmitic acid are 0.016.
Then, after being passed through nitrogen, under the conditions of bath temperature is 40 DEG C and rotating speed is 380r/min, add after being stirred until homogeneous
Enter 10g non-directional lipase Lipase DF " Amano " 15, insulated and stirred is reacted 2 hours.Centrifugation obtains organic phase supernatant, uses silicon
Glue is adsorbed and removed soap in organic phase, then molecular distillation removes free fatty and obtains faint yellow solid, tripalmitin
Content is that palmitic acid content is 93.8% on the positions 85.3%, sn-2.
Embodiment 6
Lauric acid is weighed according to the lauric acid residue amount of palm-kernel oil, so that the lauric acid residue in reaction system accounts for always
Fatty acid residue ratio be 90%, palm-kernel oil 1000g and 1000ml n-hexane is put into four-hole boiling flask, heating water bath
Until after dissolving, mixed with lauric acid and potassium methoxide.Wherein, potassium methoxide and lauric molar ratio are 0.02.
Then, after being passed through nitrogen, under the conditions of bath temperature is 85 DEG C and rotating speed is 400r/min, add after being stirred until homogeneous
Enter 80g non-directional lipase Novozym 435, insulated and stirred is reacted 0.5 hour.Centrifugation obtains organic phase supernatant, then uses silica gel
It is adsorbed and removed soap in organic phase, then molecular distillation removes free fatty and obtains faint yellow solid, laurin contains
Amount is that lauric acid content is 89.5% on the positions 82.3%, n-2.
Embodiment 7
Lauric acid is weighed according to the lauric acid residue amount of palm-kernel oil, so that the lauric acid residue in reaction system accounts for always
Fatty acid residue ratio be 92%, palm-kernel oil 1000g and 1200ml n-hexane is put into four-hole boiling flask, heating water bath
Until after dissolving, mixed with lauric acid and potassium ethoxide.Wherein, potassium ethoxide and lauric molar ratio are 0.0025.
Then, after being passed through nitrogen, under the conditions of bath temperature is 35 DEG C and rotating speed is 300r/min, add after being stirred until homogeneous
Enter 10g non-directional lipase Lipase DF " Amano " 15, insulated and stirred is reacted 2 hours.Centrifugation obtains organic phase supernatant, then uses
Silica gel absorption removes soap in organic phase, then molecular distillation removes free fatty and obtains faint yellow solid, thirdly lauric acid
Ester content is that lauric acid content is 91.4% on the positions 82.6%, sn-2.
Embodiment 8
Lauric acid is weighed according to the lauric acid residue amount of palm-kernel oil, so that the lauric acid residue in reaction system accounts for always
Fatty acid residue ratio be 97%, palm-kernel oil 1000g and 2000ml n-hexane is put into four-hole boiling flask, heating water bath
Until after dissolving, mixed with lauric acid and sodium hydroxide.Wherein, sodium hydroxide and lauric molar ratio are 0.0001.
Then, after being passed through nitrogen, under the conditions of bath temperature is 40 DEG C and rotating speed is 350r/min, add after being stirred until homogeneous
Enter 10g non-directional lipase Lipase DF " Amano " 15, insulated and stirred is reacted 5 hours.Centrifugation obtains organic phase supernatant, then uses
Silica gel absorption removes soap in organic phase, then molecular distillation removes free fatty and obtains faint yellow solid, thirdly lauric acid
Ester content is that lauric acid content is 95.4% on the positions 86.1%, sn-2.
Embodiment 9
Stearic acid is weighed according to the stearic acid residue weight of cocoa butter, so that the stearic acid residue in reaction system accounts for always
Fatty acid residue ratio be 93%, cocoa butter 1000g and 1500ml n-hexane is put into four-hole boiling flask, heating water bath is straight
To dissolving, with stearic acid and solid base catalyst (No. CAS:9049-93-8) mix.Wherein, solid base catalyst and tristearin
The molar ratio of acid is 0.016.
Then, after being passed through nitrogen, under the conditions of bath temperature is 40 DEG C and rotating speed is 400r/min, add after being stirred until homogeneous
Enter 5g non-directional lipase Lipase DF " Amano " 15, insulated and stirred is reacted 2 hours.Centrifugation obtains organic phase supernatant, then uses
Silica gel absorption removes soap in organic phase, then molecular distillation removes free fatty and obtains faint yellow solid, thirdly glycerol stearate
Ester content 82.3%, stearic acid content is 91.1% on the positions sn-2.
Embodiment 10
According to the stearic acid residue weight of cocoa butter weigh stearic acid so that the stearic acid residue in reaction system account for it is total
The ratio of fatty acid residue be 93%, cocoa butter 1000g and 1500ml n-hexane is put into four-hole boiling flask, heating water bath until
After dissolving, mixed with stearic acid and potassium hydroxide.Wherein, potassium hydroxide and stearic molar ratio are 0.001.
Then, after being passed through nitrogen, under the conditions of bath temperature is 75 DEG C and rotating speed is 440r/min, add after being stirred until homogeneous
Enter 60g non-directional lipase Novozym 435, insulated and stirred is reacted 1 hour.Centrifugation obtains organic phase supernatant, uses silica gel absorption
Soap in organic phase is removed, then molecular distillation removes free fatty and obtains faint yellow solid, glyceryl tristearate content is
Stearic acid content is 92.3% on the position 87.1%, sn-2.
Embodiment 11
Palmitic acid is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system account for
The ratio of total fatty acid residue is 85%, palmitic stearin 1000g and 2000ml n-hexane is put into four-hole boiling flask, water-bath
Heating mixes until after fusing with palmitic acid and sodium hydroxide.Wherein, sodium hydroxide and palmitic acid molar ratio are 0.016.
Then, after being passed through nitrogen, under the conditions of bath temperature is 40 DEG C and rotating speed is 380r/min, add after being stirred until homogeneous
Enter 10g non-directional lipase Lipase DF " Amano " 15, insulated and stirred is reacted 2 hours.Centrifugation obtains organic phase supernatant, uses silicon
Glue is adsorbed and removed soap in organic phase, then molecular distillation removes free fatty and obtains faint yellow solid, tripalmitin
Content is that palmitic acid content is 80.4% on the positions 64.6%, sn-2.
Embodiment 12
Palmitic acid is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system account for
The ratio of total fatty acid residue is 94%, and palmitic stearin 1000g is put into four-hole boiling flask, and heating water bath is until dissolving
Afterwards, it is mixed with palmitic acid and sodium hydroxide.Wherein, sodium hydroxide and palmitic acid molar ratio are 0.025.
Then, after being passed through nitrogen, under the conditions of bath temperature is 85 DEG C and rotating speed is 500r/min, add after being stirred until homogeneous
Enter 50g non-directional lipase Novozym 435, insulated and stirred is reacted 1 hour.After using 1500ml n-hexane extractions again, centrifuge
To organic phase supernatant, soap in organic phase is removed with silica gel absorption, then molecular distillation removes free fatty and obtains faint yellow solid,
Its tripalmitin content is that palmitic acid content is 88.2% on the positions 43.3%, sn-2.
Embodiment 13
According to the palmitic acid residues amount of palm oil weigh palmitic acid so that the palmitic acid residues in reaction system account for it is total
The ratio of fatty acid residue is 96%, palmitic stearin 1000g and 2000ml n-hexane is put into four-hole boiling flask, heating water bath
Until after dissolving, mixed with palmitic acid and potassium hydroxide.Wherein, potassium hydroxide and palmitic acid molar ratio are 0.016.It is passed through nitrogen
Afterwards, it is single-minded that 60g immobilizations 1,3 are added under the conditions of bath temperature is 65 DEG C and rotating speed is 380r/min, after being stirred until homogeneous
Property Lipozyme RMIM, insulated and stirred react 2 hours.Centrifugation obtains organic phase supernatant, is removed with silica gel absorption organic
Soap in phase, then molecular distillation remove free fatty and obtain faint yellow solid, and the palmitic acid content on the positions sn-2 is 76.6%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 20.3.
Embodiment 14
The present embodiment is differed only in embodiment 5, and the non-directional lipase Lipase DF " Amano " 15 of addition are
0.5g.Tripalmitin content is that palmitic acid content is 85.9% on the positions 75.8%, sn-2 in product obtained by the reaction.
Embodiment 15
The present embodiment is differed only in embodiment 5, and the non-directional lipase Lipase DF " Amano " 15 of addition are
100g.Tripalmitin content is that palmitic acid content is 86.8% on the positions 80.6%, sn-2 in product obtained by the reaction.
Embodiment 16
The present embodiment is differed only in embodiment 5, and the bath temperature for being catalyzed reaction is 30 DEG C.Product obtained by the reaction
Middle tripalmitin content is that palmitic acid content is 80.6% on the positions 65.8%, sn-2.
Embodiment 17
The present embodiment is differed only in embodiment 5, and the bath temperature for being catalyzed reaction is 90 DEG C.Product obtained by the reaction
Middle tripalmitin content is that palmitic acid content is 79.3% on the positions 64.2%, sn-2.
Comparative example 1
Palmitic stearin 30kg is weighed in 100L pilot reactors, sodium palmitate 5kg is added, leads to nitrogen, heating stirring.
Then, reaction temperature is stablized at 180 DEG C, rotating speed 300r/min, reacts 12h.50 DEG C are down to, n-hexane dissolution solid is added,
Centrifugation obtains organic phase supernatant, and silica gel absorption removes soap in organic phase, is concentrated to give faint yellow solid, tripalmitin
Content is that palmitic acid content is 63.6% on the positions 40.7%, sn-2..
Comparative example 2
Palmitic stearin 30kg is weighed in 100L pilot reactors, sodium palmitate 5kg is added, leads to nitrogen, heating stirring.
Then, reaction temperature is stablized at 185 DEG C, rotating speed 400r/min, reacts 20h.50 DEG C are down to, n-hexane dissolution solid is added,
Water is added and adsorbs soap.Filtering, silica gel absorption remove soap in organic phase, are concentrated to give faint yellow solid, tripalmitin
Content is that the palmitic acid content on the positions 41.2%, sn-2 is 64.2%.
Comparative example 3
According to the palmitic acid residues amount of palm oil weigh palmitic acid so that the palmitic acid residues in reaction system account for it is total
The ratio of fatty acid residue is 96%, palmitic stearin 1000g and 1500ml n-hexane is put into four-hole boiling flask, heating water bath
Until after dissolving, mixed with palmitic acid.After being passed through nitrogen, under the conditions of bath temperature is 40 DEG C and rotating speed is 380r/min, stir
It mixes to uniformly rear and 10g non-directional lipase Lipase DF " Amano " 15 is added, insulated and stirred is reacted 2 hours.Centrifugation is had
Machine phase supernatant, then soap in organic phase is removed with silica gel absorption, it is concentrated to give faint yellow solid, tripalmitin content is
Palmitic acid content on the position 51.2%, sn-2 is 78%.
Embodiment 10 is arrived by embodiment 1, it can be seen that three saturated fats that embodiment is prepared through the invention
The purity of acid glyceride reaches 80% or more, and reaction condition is mild, and side reaction is few.Pass through comparative example 5 and embodiment
11 comparisons are it is found that the additive amount of saturated fatty acid has larger impact to the purity of three obtained saturated fatty acid glycerides, when it
Additive amount makes the saturated fatty acid residues in reaction system account for the ratio of total fatty acid residue at 90%, can obtain pure
Spend higher product.By comparison example 3 and embodiment 12 it is found that solvent is added in the reaction system is conducive to catalysis reaction
Effect improves the purity of product.It is compared according to embodiment 5 and embodiment 13, it can be seen that astaticism lipase is opposite
Orientation lipase plays good catalytic effect in the preparation method of embodiments of the present invention.By by embodiment 5 and in fact
It applies example 14 and 15 and carries out comparison as can be seen that the additive amount of lipase is not more, three saturated fatty acid glyceride contents are higher.
By the way that embodiment 5 and embodiment 16 and embodiment 17 are compared, it can be seen that temperature is excessively high and temperature is too low, and catalysis is anti-
Effect is answered can be significantly deteriorated.By the way that embodiment 1-10 and comparative example 1-3 are compared, it can be seen that its it is opposite with only in fat
It is produced under the action of the chemical catalysis or lipase of fat hydrochlorate and obtains three saturated fatty acid glycerides, in embodiment of the present invention
Its reaction condition of method is mild, side reaction is reduced, and purity greatly improves.
In conclusion on the basis of glyceride fraction has saturated fatty acid residues, pass through corresponding saturated fatty acid
Sufficient amount of saturated fatty acid residues are provided with the generated in-situ Salt of saturated fatty acid of alkali, and utilize non-directional lipase
Catalytic action so that its reaction condition is mild, and side reaction is few, so that the purity of three saturated fatty acid glycerides generated
It is high.
Embodiments described above is a part of the embodiment of the present invention, instead of all the embodiments.The reality of the present invention
The detailed description for applying example is not intended to limit the range of claimed invention, but is merely representative of the selected implementation of the present invention
Example.Based on the embodiments of the present invention, those of ordinary skill in the art are obtained without creative efforts
Every other embodiment, shall fall within the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of three saturated fatty acid glycerides, which is characterized in that it includes：
Glyceride containing saturated fatty acid residues, saturated fat bronsted lowry acids and bases bronsted lowry are subjected to catalysis reaction under the action of lipase,
Obtain three saturated fatty acid glyceride；
The corresponding saturated fatty acid of wherein described saturated fatty acid residues is identical as the saturated fatty acid for participating in catalysis reaction,
And the glyceride containing saturated fatty acid residues at least has that there are one the ester bonds or hydroxyl that are not combined with saturated fatty acid residues
Base.
2. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that the glyceride with
The ratio that saturated fatty acid residues in the reaction system of the saturated fatty acid account for total fatty acid residue is greater than or equal to
90%, preferably greater than 92%, more preferably greater than 95%.
3. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that the lipase
Additive amount is the 0.05~10% of the glyceride, it is therefore preferable to 0.1~8%, it is preferable that the lipase is non-directional fat
Enzyme, it is highly preferred that the non-directional lipase include Novozym 435, Lipase DF " Amano " 15, LipozymeTLIM and
At least one of LipaseAY30G.
4. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that be catalyzed the temperature of reaction
Degree is 30~90 DEG C, and preferably 35~85 DEG C, the time for being catalyzed reaction is 0.5~9 hour, preferably 1~4 hour.
5. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that the glyceride packet
Include at least one of monoglyceride, diglyceride and triglycerides.
6. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that the saturated fat
Acid is selected from palmitic acid, stearic acid, octanoic acid, capric acid, lauric acid, myristic acid or arachidic acid, preferably palmitic acid or stearic acid, more preferably
Palmitic acid.
7. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that the alkali with it is described
The molar ratio of saturated fatty acid is not more than 1.
8. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that the alkali is
NaOH、KOH、NaOC2H5、KOC2H5、NaOCH3、KOCH3, solid base catalyst and its mixture, it is further preferred that the alkali
For NaOH or KOH.
9. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that carry out catalysis reaction
It specifically includes and institute is added after mixing the glyceride containing saturated fatty acid residues with the saturated fatty acid and the alkali
Lipase is stated, under conditions of being passed through inert gas, is stirred reaction.
10. the preparation method of three saturated fatty acid glyceride according to claim 1, which is characterized in that the reactant
Further include solvent in system, the preferred n-hexane of solvent.
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| WO2020007334A1 (en) * | 2018-07-04 | 2020-01-09 | 嘉必优生物技术（武汉）股份有限公司 | Tri-saturated fatty acid glyceride and usu-type triglyceride |
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