CN108795998A - A method of reducing glyceride iodine number - Google Patents
A method of reducing glyceride iodine number Download PDFInfo
- Publication number
- CN108795998A CN108795998A CN201810724944.1A CN201810724944A CN108795998A CN 108795998 A CN108795998 A CN 108795998A CN 201810724944 A CN201810724944 A CN 201810724944A CN 108795998 A CN108795998 A CN 108795998A
- Authority
- CN
- China
- Prior art keywords
- glyceride
- fatty acid
- iodine number
- saturated fatty
- lipase
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
The present invention relates to glycerine Lipase absobed processing technique fields, and in particular to a method of reducing glyceride iodine number comprising：Glyceride is carried out catalysis under the action of lipase with Salt of saturated fatty acid to react, obtains the glyceride of the low iodine number.Sufficient amount of saturated fatty acid residues are provided by corresponding Salt of saturated fatty acid, and utilize the catalytic action of lipase so that its reaction condition is mild, and side reaction is few, and significantly reduces the iodine number of glyceride.
Description
Technical field
The present invention relates to glycerine Lipase absobed processing technique fields, in particular to a kind of side reducing glyceride iodine number
Method.
Background technology
It needs to produce the raw material that the lower glyceride of iodine number is used as Chemical Manufacture, but existing increase in the industrial production
The method of the saturation degree of glyceride is mainly carried out by chemical catalysis, and reaction needs high temperature, process conditions harsh.Cause
This, is there is an urgent need for a kind of simple process, the method that can effectively reduce glyceride iodine number.
Invention content
The purpose of the present invention is to provide a kind of methods reducing glyceride iodine number, can improve saturated fat in glyceride
The content of fat acid, so that the iodine number of glyceride effectively reduces, 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 method reducing glyceride iodine number provided by the invention comprising：Glyceride and Salt of saturated fatty acid are existed
Catalysis reaction is carried out under the action of lipase.-
On the basis of glyceride fraction has saturated fatty acid residues, provided by corresponding Salt of saturated fatty acid enough
The saturated fatty acid residues of quantity, and utilize the catalytic action of lipase so that its reaction condition is mild, and side reaction is few, raw
At glyceride iodine number it is low.
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.
A kind of method of reduction glyceride iodine number of embodiment of the present invention is specifically described below.
A kind of method for reduction glyceride iodine number that some embodiments of the present invention provide comprising：By glyceride with
Salt of saturated fatty acid carries out catalysis reaction under the action of lipase, obtains the glyceride of saturated fatty acid high-content.
Iodine number indicates a kind of index of degree of unsaturation in organic compound.(addition) iodine can be absorbed by referring in 100g substances
Grams.It is mainly used for the measurement of the substances such as grease, aliphatic acid, wax and polyesters.Degree of unsaturation is bigger, and iodine number is higher.
The glyceride can be monoglyceride, can also be diglyceride either triglycerides or diglyceride and sweet
The mixture of oily three esters.
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.
According to some embodiments, glyceride is the glyceride containing saturated fatty acid residues, it is preferable that the glyceride
Iodine number be more than 20, it is preferable that the corresponding saturated fatty acid of saturated fatty acid residues that glyceride contains at least with saturated fat
A kind of corresponding saturated fatty acid of hydrochlorate is identical.
On the basis of glyceride has the part ester bond of specific saturated fatty acid residues, it is capable of providing largely by introducing
The special fatty acid salt of special fatty acid residue, so that transesterification and esterification can occurs under the catalysis of lipase in it
Reaction, thereby reduces reaction condition so that side reaction is few, and the iodine number for generating glyceride is low.
According to some embodiments, the ratio of glyceride and Salt of saturated fatty acid be using Salt of saturated fatty acid as additive amount,
So that the ratio that the saturated fatty acid residues in reaction system account for total fatty acid residue is greater than or equal to 90%, preferably greater than
92%, more preferably greater than 95%.For example, can so that adding Salt of saturated fatty acid makes the saturated fatty acid in reaction system residual
The ratio of the total fatty acid residue of fiduciary point is 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97% or 98% etc..
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 reaction product of low iodine number.
According to some embodiments, lipase can be non-directional lipase, additive amount be glyceride 0.05~
10%, it is therefore preferable to 0.1~8%, in further preferred scheme, the additive amount of Novozym 435 is 4~8%, Lipase
The additive amount of DF " Amano " 15 is 0.1~1%, the addition that the additive amount of LipozymeTLIM is 4~8%, LipaseAY30G
Amount 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 can not
Reach catalytic effect, adding too much then makes cost increase, and can influence reactant in reaction process to a certain extent
Between contact, cause reaction effect bad.It therefore, can be fully by the additive amount of the non-directional lipase of above range
Reach the catalytic action to reaction so that reaction carries out more thorough in the reaction time fixed shortly.
In some embodiments, 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 for being catalyzed reaction is 30~90 DEG C, preferably 35~85 DEG C, is catalyzed the time of reaction
It it is 0.5~9 hour, the preferred reaction time is 1~4 hour.Under the reaction temperature, reaction temperature is relative to traditional chemistry
The reaction temperature of catalyst is relatively low, and reaction is more prone to carry out, and reaction temperature can be kept by way of heating water bath
Constant, it is heated relatively uniform for heating water bath, and heat transfer effect is good, so that reaction is more prone to carry out.Certainly, also may be used
To select other mode of heatings such as furnace body heating to carry out maintaining reaction temperature.
According to some embodiments, the corresponding saturated fatty acid in saturated fatty acid residues and Salt of saturated fatty acid is selected from
At least one of palmitic acid, stearic acid, octanoic acid, capric acid, lauric acid, myristic acid and arachidic acid, preferably palmitic acid, stearic acid, beans
At least one of cool acid, at least one of more preferable palmitic acid, stearic acid.For example, reactant can be residual containing palmitic acid
The glyceride and palmitate of base, can also be the glyceride containing stearic acid residue and stearic acid salt, or contain lauric acid
The glyceride and laruate of residue.In addition, saturated fatty acid can also be that palmitic acid, stearic acid are mixed with what certain proportion mixed
Close object.
Select the purpose of fatty acid salt to be in embodiments of the present invention, fatty acid salt as a kind of strong base-weak acid salt,
Ionizing power is strong, and fatty acid residue activity is strong, provides fatty acid residue ability and is much larger than free fatty or aliphatic ester, from
And accelerate the rate of ester exchange reaction, shorten the reaction time, it is possible to reduce fatty enzyme dosage reduces cost.
According to some embodiments, the glyceride containing saturated fatty acid residues can be cocoa butter, coconut oil, palm kernel
Oil or palm oil.Preferably, the glyceride containing saturated fatty acid residues is palm oil.
According to some embodiments, Salt of saturated fatty acid is saturated fat acid alkali metal salt, it is preferable that Salt of saturated fatty acid
For saturated fatty acid sodium or saturated fatty acid potassium.
According to some embodiments, carry out catalysis reaction specifically include glyceride is mixed with Salt of saturated fatty acid after be added
Lipase is stirred reaction under conditions of being passed through inert gas.It can be to avoid outside air by the protection of inert gas
It is reacted and is impacted, and stirring can come into full contact between reactant so that reaction is more fully quickly.
Further, catalysis reaction is carried out to preferably include to add after the glyceride containing saturated fatty acid residues is mixed with Salt of saturated fatty acid
Enter non-directional lipase, under conditions of being passed through inert gas, is stirred reaction.
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 centrifuged after catalysis is reacted, then the soap in organic phase removed by silica gel absorption.
It should be noted that the mass ratio of Salt of saturated fatty acid and glyceride can be with the iodine number and product of glyceride
The ratio of iodine number desired value is additive amount, so that Salt of saturated fatty acid is not less than glyceride feedstock with glyceride mass ratio
The iodine number ratio of iodine number and product iodine number desired value subtracts 1.
A kind of method for reduction glyceride iodine number that some embodiments of the present invention provide comprising：Palm will be contained
The glyceride of sour residue carries out catalysis under the action of non-directional lipase with palmitate and reacts, and obtains three palms of low iodine number
Acid glyceride.It is wherein triglycerides as the glyceride of raw material.
In some embodiments, USU type triglycerides, such as 1, bis- oil of 3- can also be synthesized with the glyceride of low iodine number
Three ester (OPO) of acid -2- palmitic acids.
The feature and performance of the present invention are described in further detail with reference to embodiments.
Embodiment 1
Potassium palmitate is weighed according to the palmitic acid residues amount of palm oil, so that the palmitic acid residues in reaction system account for always
Fatty acid residue ratio be 90%, palmitic stearin 1000g and 1000ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with potassium palmitate.After being passed through nitrogen, in bath temperature be 35 DEG C and rotating speed is 400r/min conditions
Under, 5g non-directional lipase Lipase DF " Amano " 15 are added after being stirred until homogeneous, insulated and stirred is reacted 4 hours.It centrifuges
Soap in organic phase is removed to organic phase supernatant, then with silica gel absorption, is concentrated to give faint yellow solid, the palmitic acid on the positions sn-2
Content is 89.5%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 7.3.
Embodiment 2
Potassium palmitate and potassium stearate are weighed according to the palmitic acid residues of palm oil and stearic acid residue weight, so that reaction
The ratio that palmitic acid residues and stearic acid residue in system account for total fatty acid residue is 92% and palmitic acid residues and tristearin
Sour residue ratio is 4:1, palmitic stearin 1000g and 1200ml n-hexane is put into four-hole boiling flask, heating water bath is until molten
Xie Hou is mixed with potassium palmitate and potassium stearate.After being passed through nitrogen, in bath temperature be 40 DEG C and rotating speed is 350r/min conditions
Under, 10g non-directional lipase LipaseAY30G are added after being stirred until homogeneous, insulated and stirred is reacted 1 hour.Centrifugation obtains organic
Phase supernatant, then soap in organic phase is removed with silica gel absorption, it is concentrated to give faint yellow solid, the palmitic acid on the positions sn-2 and tristearin
The sum of acid content is 88.5%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 7.0.
Embodiment 3
Sodium palmitate is weighed according to the palmitic acid residues amount of palm oil, so that the palmitic acid residues in reaction system account for always
Fatty acid residue ratio be 94%, palmitic stearin 1000g and 1500ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with sodium palmitate.After being passed through nitrogen, in bath temperature be 85 DEG C and rotating speed is 500r/min conditions
Under, 50g non-directional lipase Novozym 435 is added after being stirred until homogeneous, insulated and stirred is reacted 1 hour.Centrifugation obtains organic
Phase supernatant, then soap in organic phase is removed with silica gel absorption, it is concentrated to give faint yellow solid, the palmitic acid content on the positions sn-2 is
92.3%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 7.1.
Embodiment 4
Sodium palmitate is weighed according to the palmitic acid residues amount of palm oil, so that the palmitic acid residues in reaction system account for always
Fatty acid residue ratio be 94%, palmitic stearin 1000g and 2000ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with sodium palmitate.After being passed through nitrogen, in bath temperature be 65 DEG C and rotating speed is 400r/min conditions
Under, 40g non-directional Lipozyme TLIM are added after being stirred until homogeneous, insulated and stirred is reacted 2 hours.Centrifugation obtains organic
Phase supernatant, then soap in organic phase is removed with silica gel absorption, it is concentrated to give faint yellow solid, the palmitic acid content on the positions sn-2 is
93.5%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 5.1.
Embodiment 5
Potassium palmitate is weighed according to the palmitic acid residues amount of palm oil, so that the palmitic acid residues in reaction system account for always
Fatty acid residue ratio be 96%, palmitic stearin 1000g and 2000ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with potassium palmitate.After being passed through nitrogen, in bath temperature be 40 DEG C and rotating speed is 380r/min conditions
Under, 10g non-directional lipase Lipase DF " Amano " 15 are added after being stirred until homogeneous, insulated and stirred is reacted 2 hours.It centrifuges
Soap in organic phase is removed to organic phase supernatant, then with silica gel absorption, is concentrated to give faint yellow solid, the palmitic acid on the positions sn-2 contains
Amount is 94.8%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 5.6.
Embodiment 6
Potassium laurate is weighed according to the lauric acid residue amount of palm-kernel oil, so that the lauric acid residue in reaction system accounts for
The ratio of total fatty acid residue is 90%, palm-kernel oil 1000g and 1000ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with potassium laurate.After being passed through nitrogen, in bath temperature be 85 DEG C and rotating speed is 400r/min conditions
Under, 40g non-directional lipase Novozym 435 is added after being stirred until homogeneous, insulated and stirred is reacted 0.5 hour.Centrifugation is had
Machine phase supernatant, then soap in organic phase is removed with silica gel absorption, it is concentrated to give solid, the lauric acid content on the positions sn-2 is
89.4%.
Wherein, the iodine number of the palm-kernel oil reacted is 30, and the iodine number of the glyceride product obtained after reaction is 7.3.
Embodiment 7
Potassium laurate is weighed according to the lauric acid residue amount of palm-kernel oil, so that the lauric acid residue in reaction system accounts for
The ratio of total fatty acid residue is 92%, palm-kernel oil 1000g and 1200ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with potassium laurate.After being passed through nitrogen, in bath temperature be 35 DEG C and rotating speed is 300r/min conditions
Under, 10g non-directional lipase Lipase DF " Amano " 15 are added after being stirred until homogeneous, insulated and stirred is reacted 2 hours.It centrifuges
Soap in organic phase is removed to organic phase supernatant, then with silica gel absorption, is concentrated to give solid, the lauric acid content on the positions sn-2 is
91.3%.
Wherein, the iodine number of the palm-kernel oil reacted is 30, and the iodine number of the glyceride product obtained after reaction is 6.9.
Embodiment 8
Sodium laurate is weighed according to the lauric acid residue amount of palm-kernel oil, so that the lauric acid residue in reaction system accounts for
The ratio of total fatty acid residue is 97%, palm-kernel oil 1000g and 2000ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with sodium laurate.After being passed through nitrogen, in bath temperature be 40 DEG C and rotating speed is 350r/min conditions
Under, 10g non-directional lipase Lipase DF " Amano " 15 are added after being stirred until homogeneous, insulated and stirred is reacted 5 hours.It centrifuges
Soap in organic phase is removed to organic phase supernatant, then with silica gel absorption, is concentrated to give solid, the lauric acid content on the positions sn-2 is
95.4%.
Wherein, the iodine number of the palm-kernel oil reacted is 30, and the iodine number of the glyceride product obtained after reaction is 5.0.
Embodiment 9
Potassium stearate 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 2000ml n-hexane is put into four-hole boiling flask, heating water bath is straight
To dissolving, mixed with potassium stearate.After being passed through nitrogen, under the conditions of bath temperature is 40 DEG C and rotating speed is 400r/min, stir
It mixes to uniformly rear and 5g non-directional lipase Lipase DF " Amano " 15 is added, insulated and stirred is reacted 2 hours.Centrifugation obtains organic
Phase supernatant, then soap in organic phase is removed with silica gel absorption, the stearic acid content being concentrated to give on the positions solid sn-2 is 91.6%.
Wherein, the iodine number of the cocoa butter reacted is 28, and the iodine number of the glyceride product obtained after reaction is 5.7.
Embodiment 10
Potassium stearate 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, mixed with potassium stearate.After being passed through nitrogen, under the conditions of bath temperature is 75 DEG C and rotating speed is 440r/min, stir
It mixes to uniformly rear and 60g non-directional lipase Novozym 435 is added, insulated and stirred is reacted 1 hour.Centrifugation obtains in organic phase
Clearly, then with silica gel absorption soap in organic phase is removed, is concentrated to give solid, the stearic acid content on the positions sn-2 is 91.3%.
Wherein, the iodine number of the cocoa butter reacted is 28, and the iodine number of the glyceride product obtained after reaction is 6.2.
Embodiment 11
Potassium palmitate is weighed according to the palmitic acid residues amount of palm oil, so that the palmitic acid residues in reaction system account for always
Fatty acid residue ratio be 85%, palmitic stearin 1000g and 2000ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with potassium palmitate.After being passed through nitrogen, in bath temperature be 40 DEG C and rotating speed is 380r/min conditions
Under, 10g non-directional lipase Lipase DF " Amano " 15 are added after being stirred until homogeneous, insulated and stirred is reacted 2 hours.It centrifuges
Soap in organic phase is removed to organic phase supernatant, then with silica gel absorption, is concentrated to give faint yellow solid, the palmitic acid on the positions sn-2 contains
Amount is 81.4%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 18.
Embodiment 12
Potassium palmitate is weighed according to the palmitic acid residues amount of palmitic stearin, so that the palmitic acid residues in reaction system
The ratio for accounting for 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 potassium palmitate.After being passed through nitrogen, under the conditions of bath temperature is 85 DEG C and rotating speed is 500r/min, stir to equal
50g non-directional lipase Novozym 435 is added after even, insulated and stirred is reacted 1 hour.After 2000mL n-hexane extractions, from
Gains in depth of comprehension remove soap in organic phase to organic phase supernatant, with silica gel absorption, are concentrated to give faint yellow solid, the palmitic acid on the positions sn-2
Content is 87.2%.
Wherein, the iodine number of the palmitic stearin reacted is 35, and the iodine number of the glyceride product obtained after reaction is
19.5。
Embodiment 13
Potassium palmitate is weighed according to the palmitic acid residues amount of palm oil, so that the palmitic acid residues in reaction system account for always
Fatty acid residue ratio be 96%, palmitic stearin 1000g and 2000ml n-hexane is put into four-hole boiling flask, water-bath adds
Heat mixes until after dissolving with potassium palmitate.After being passed through nitrogen, in bath temperature be 65 DEG C and rotating speed is 380r/min conditions
Under, 60g 1,3 specific lipase Lipozyme RMIM of immobilization are added after being stirred until homogeneous, insulated and stirred is reacted 2 hours.
Soap in organic phase is removed with silica gel absorption again, is concentrated to give faint yellow solid, the palmitic acid content on the positions sn-2 is 74.6%.
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.The iodine number of the glyceride product obtained after reaction is 12.5.
Embodiment 15
The present embodiment is differed only in embodiment 5, and the non-directional lipase Lipase DF " Amano " 15 of addition are
100g.The iodine number of the glyceride product obtained after reaction is 5.2.
Embodiment 16
The present embodiment is differed only in embodiment 5, and the bath temperature for being catalyzed reaction is 30 DEG C.What is obtained after reaction is sweet
The iodine number of grease product is 14.5.
Embodiment 17
The present embodiment is differed only in embodiment 5, and the bath temperature for being catalyzed reaction is 90 DEG C.What is obtained after reaction is sweet
The iodine number of grease product is 29.2.
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, the palm on the positions sn-2
Acid content is 63.6%.
Wherein, the iodine number of the palmitic stearin reacted is 35, and the iodine number of the glyceride product obtained after reaction is
24.8。
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, the palm on the positions sn-2
Acid content is 64.2%.
Wherein, the iodine number of the palmitic stearin reacted is 35, and the iodine number of the glyceride product obtained after reaction is
23.2。
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 1.5 hours.Centrifugation obtains
Organic phase supernatant, then soap in organic phase is removed with silica gel absorption, it is concentrated to give faint yellow solid, the palmitic acid content on the positions sn-2
It is 78%.
Wherein, the iodine number of the palm oil reacted is 35, and the iodine number of the glyceride product obtained after reaction is 17.
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 it is found that the additive amount of Salt of saturated fatty acid has larger impact to the purity of three obtained saturated fatty acid glycerides, when
Its additive amount makes the saturated fatty acid residues in reaction system account for the ratio of total fatty acid residue at 90%, can obtain
The higher product of purity.By comparative example 3 and embodiment 12 it is found that solvent is added in the reaction system is conducive to catalysis instead
The effect answered improves the purity of product.It is compared according to embodiment 5 and embodiment 13, it can be seen that astaticism lipase
Relative orientation lipase plays good catalytic effect in the preparation method of embodiments of the present invention.By by embodiment 5
Comparison is carried out with embodiment 14 and 15 as can be seen that the additive amount of lipase is not more, and iodine number is smaller.By by embodiment
5 are compared with embodiment 16 and embodiment 17, it can be seen that temperature is excessively high and temperature is too low, and catalysis reaction effect can be shown
It writes and is 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 the chemistry of fatty acid salt
Production obtains three saturated fatty acid glycerides under catalysis or fatty enzyme effect, method its reaction condition in embodiment of the present invention
Mildly, 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
Salt provides sufficient amount of saturated fatty acid residues, and utilizes the catalytic action of lipase so that its reaction condition is mild, secondary
Reaction is few, so that the glyceride iodine number generated is low.
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 method reducing glyceride iodine number, which is characterized in that it includes：
Glyceride is carried out catalysis with Salt of saturated fatty acid under the action of lipase to react.
2. the method according to claim 1 for reducing glyceride iodine number, which is characterized in that the glyceride and the saturation
In the reaction system of fatty acid salt saturated fatty acid residues account for total fatty acid residue ratio be greater than or equal to 90%, preferably greatly
In 92%, more preferably greater than 95%.
3. the method according to claim 1 for reducing glyceride iodine number, which is characterized in that the additive amount of the lipase 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 lipase, more excellent
Selection of land, the non-directional lipase include Novozym 435, Lipase DF " Amano " 15, LipozymeTLIM and
At least one of LipaseAY30G.
4. it is according to claim 1 reduce glyceride iodine number method, which is characterized in that be catalyzed reaction temperature be 30~
90 DEG C, preferably 40~80 DEG C, the time for being catalyzed reaction are 0.5~9 hour, preferably 1~4 hour.
5. the method according to claim 1 for reducing glyceride iodine number, which is characterized in that the glyceride is to contain saturation
The glyceride of fatty acid residue, it is preferable that the iodine number of the glyceride is more than 20, it is preferable that the saturation that the glyceride contains
A kind of corresponding saturated fatty acid of fatty acid residue saturated fatty acid at least corresponding with the Salt of saturated fatty acid is identical.
6. the method according to claim 1 for reducing glyceride iodine number, which is characterized in that the glyceride includes glycerine one
At least one of ester, diglyceride and triglycerides.
7. the method according to claim 1 for reducing glyceride iodine number, it is characterised in that right in the Salt of saturated fatty acid
The saturated fatty acid answered is selected from least one of palmitic acid, stearic acid, octanoic acid, capric acid, lauric acid, myristic acid or arachidic acid, excellent
Select at least one of palmitic acid, stearic acid, myristic acid and lauric acid, at least one of more preferable palmitic acid and stearic acid.
8. the method according to claim 1 for reducing glyceride iodine number, which is characterized in that the Salt of saturated fatty acid is full
And fatty acid alkali metal salt, it is preferable that the Salt of saturated fatty acid is saturated fatty acid sodium or saturated fatty acid potassium.
9. the method according to claim 1 for reducing glyceride iodine number, which is characterized in that carry out catalysis reaction and specifically include
The lipase is added after the glyceride is mixed with the Salt of saturated fatty acid, under conditions of being passed through inert gas, into
Row is stirred to react.
10. the method according to claim 1 for reducing glyceride iodine number, which is characterized in that also wrapped in the reaction system
Include solvent, the preferred n-hexane of solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810724944.1A CN108795998B (en) | 2018-07-04 | 2018-07-04 | Method for reducing iodine value of glyceride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810724944.1A CN108795998B (en) | 2018-07-04 | 2018-07-04 | Method for reducing iodine value of glyceride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108795998A true CN108795998A (en) | 2018-11-13 |
| CN108795998B CN108795998B (en) | 2021-11-19 |
Family
ID=64074434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810724944.1A Active CN108795998B (en) | 2018-07-04 | 2018-07-04 | Method for reducing iodine value of glyceride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108795998B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN114934080A (en) * | 2022-04-06 | 2022-08-23 | 西北大学 | Preparation method of phospholipid type DHA |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101258230A (en) * | 2005-09-08 | 2008-09-03 | 荷兰洛德斯克罗科兰有限公司 | Process for producing dioleyl palmitoyl glyceride |
| CN101679909A (en) * | 2007-02-28 | 2010-03-24 | 荷兰洛德斯克罗科兰有限公司 | Process for producing a glyceride composition |
| CN102523744A (en) * | 2010-09-10 | 2012-06-27 | 株式会社钟化 | Method for producing tri-saturated fatty acid glyceride-containing fat compositions |
| CN102858931A (en) * | 2010-04-22 | 2013-01-02 | 株式会社钟化 | Liquid oil and fat, and production method therefor |
| CN103103226A (en) * | 2012-11-10 | 2013-05-15 | 江南大学 | Method for preparing soybean phospholipid with low iodine value |
| CN104087626A (en) * | 2014-07-07 | 2014-10-08 | 嘉必优生物工程（武汉）有限公司 | Method for preparing composition containing 2-palmitin |
-
2018
- 2018-07-04 CN CN201810724944.1A patent/CN108795998B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101258230A (en) * | 2005-09-08 | 2008-09-03 | 荷兰洛德斯克罗科兰有限公司 | Process for producing dioleyl palmitoyl glyceride |
| CN101679909A (en) * | 2007-02-28 | 2010-03-24 | 荷兰洛德斯克罗科兰有限公司 | Process for producing a glyceride composition |
| CN102858931A (en) * | 2010-04-22 | 2013-01-02 | 株式会社钟化 | Liquid oil and fat, and production method therefor |
| CN102523744A (en) * | 2010-09-10 | 2012-06-27 | 株式会社钟化 | Method for producing tri-saturated fatty acid glyceride-containing fat compositions |
| CN103103226A (en) * | 2012-11-10 | 2013-05-15 | 江南大学 | Method for preparing soybean phospholipid with low iodine value |
| CN104087626A (en) * | 2014-07-07 | 2014-10-08 | 嘉必优生物工程（武汉）有限公司 | Method for preparing composition containing 2-palmitin |
| CN106591386A (en) * | 2014-07-07 | 2017-04-26 | 嘉必优生物技术（武汉）股份有限公司 | Preparation method of composition containing 2-tripalmitin |
Non-Patent Citations (3)
| Title |
|---|
| 冯瑞军: "脂肪酶催化红花油水解的选择性研究", 《陕西科技大学学报》 * |
| 班婷婷: "醇溶性大豆磷脂与棕榈酸酶促酸解反应的研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 胡晓中等: "脂肪酶在脂质分析和油脂工业上应用", 《粮食与油脂》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN114934080A (en) * | 2022-04-06 | 2022-08-23 | 西北大学 | Preparation method of phospholipid type DHA |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108795998B (en) | 2021-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4268527A (en) | Method for producing cacao butter substitute | |
| CN102010786B (en) | Glyceride composition and preparing method thereof | |
| CN102757988B (en) | Preparation method of 1,3-dioleoyl-2-palmitoyl triglyceride | |
| CN108865445A (en) | A method of reducing glyceride iodine number | |
| KR100286955B1 (en) | Synthesis of Acetoglyceride Fats | |
| JPS6339233B2 (en) | ||
| JPH05507100A (en) | Methods of preparing triglycerides and triglyceride compositions | |
| CN108795998A (en) | A method of reducing glyceride iodine number | |
| US4806632A (en) | Process for the post-hydrogenation of sucrose polyesters | |
| CN108823255A (en) | A kind of preparation method of three saturated fatty acid glycerides | |
| JPH0338837B2 (en) | ||
| CN108796000A (en) | Three saturated fatty acid glycerides of one kind and USU type triglycerides | |
| CN111094312B (en) | Preparation method of sucrose ester | |
| CN105767216B (en) | High oleic acid grease composition and preparation method thereof | |
| CN108642097A (en) | A kind of preparation method of three saturated fatty acid glycerides | |
| CN108795999A (en) | A kind of preparation method of three saturated fatty acid glycerides | |
| CN112841313A (en) | Preparation method of oil rich in OPL and OPO and product thereof | |
| CN106086096B (en) | A kind of method for efficiently preparing phenolic acid glyceride | |
| JPS6322798B2 (en) | ||
| EP0428249B1 (en) | Transesterification of triglycerides | |
| NZ772540B2 (en) | Method for lowering iodine value of glyceride | |
| JP2711391B2 (en) | Method for producing reformed oil | |
| JP4945838B2 (en) | Oil and fat manufacturing method | |
| JPH0327199B2 (en) | ||
| JP6904009B2 (en) | Oil and fat manufacturing method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |