CN104178531A - Method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil - Google Patents
Method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil Download PDFInfo
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Abstract
The invention relates to a method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil. The method is characterized by comprising the following steps: (1) addition of reaction raw materials: adding phytosterin, high-acid-value grease and molecular sieve into a reaction kettle, adding 100-200ppm of antioxidant, heating to 45-60 DEG C, stirring and carrying out ultrasonic treatment to obtain a premixture, wherein the mole ratio of the phytosterin to free fatty acids in the high-acid-value grease is 1:1-5:1; (2) enzymatic ester exchange reaction: adding 5-40 g/L lipase into the premixture, and stirring to react at 45-60 DEG C under normal pressure for 6-12 hours; and (3) carrying out after-treatment on the product to obtain the functional grease containing rich phytosterin ester. The method can obviously lower the acid value of the high-acid-value vegetable oil and generate the new functional active component phytosterin ester, and the product is simple for separation and purification; and thus, the method can easily implement large-scale amplification.
Description
Technical field
The present invention relates to utilize high valent acid vegetable oil to produce the preparation method who is rich in plant sterol ester biodiesel, be specifically related to utilize high valent acid vegetable oil for raw material, the method that is rich in plant sterol ester biodiesel by the one step preparation of lipase-catalyzed esterification method, belongs to grease deep processing and higher value application field.
Background technology
Normal its acid value of vegetables oil of producing is generally lower, but in particular cases, as high in moisture in oil plant, preserve the effect etc. that has enzyme in improper and processing, cause the acid value of lipids produced higher, wherein more typically have high-acid-value wheat-germ oil and high acid value Rice pollard oil.High acid value grease mainly refers to that acid value is greater than the grease of 20mgKOH/g.The representative of high acid value grease---Rice pollard oil not only its lipid acid constituent ratio is more reasonable, and contain abundant thiaminogen, squalene, VE (tocopherol, tocotrienols), the various active material such as sterol, therefore there is raising immunizing power, reduce cholesterol, regulate blood fat, the physiologically actives such as atherosclerosis, being described as by nutritionist " nutrition oil ", is a kind of desirable food oils.In rice bran, contain active higher lipolytic enzyme, cause the free fatty acid content in Rice pollard oil higher, generally, more than 10%, some is even between 30%-40%.At present, high acid value grease is mainly used in depickling and becomes low acid value grease, preparation biofuel and lipid acid etc.High acid value grease carries out depickling meeting according to conventional grease acid stripping method and has the problems such as environmental pollution is serious, energy consumption large, neutral grease yield is low.Traditional alkali-refining deacidification method can be reduced to specified requirement by Rice pollard oil acid number, but alkali refining runs off the nutritive ingredient such as thiaminogen in Rice pollard oil in a large number, meanwhile, because soap is carried secretly the emulsification of grease and inevitable fat saponification, have a strong impact on oil and fat refining yield.Along with the development of biotechnology, this reaction conditions gentleness of zymotechnic, the novel process technology that catalytic efficiency is high have caused relevant scholar's attention.Using is at present that to adopt glycerine or monoglyceride be esterifying agent as acyl acceptor comparatively widely, reaches the object of depickling with free fatty acids generation esterification.
Plant sterol ester has not only retained plant sterol and has reduced that cholesterin and regulating blood-fat, anti-inflammatory are brought down a fever, the physiologically active such as anticancer, also have better fat-soluble, at grease or containing the more broad range of application in fatty foods.In addition, the absorption rate of plant sterol ester is 5 times of plant sterol, and has better Lowering cholesterol effect, is a kind of novel functional food ingredient.2010, plant sterol ester was listed in new food resource by the Ministry of Health of China.
The free fatty acids generation enzymatic esterification of the present invention using plant sterol as acry radical donor and in the high-acid value grease such as Rice pollard oil or wheatgerm oil; can obviously reduce on the one hand the acid value of high-acid value grease; can generate on the other hand new functional active components-plant sterol ester, finally can obtain the biodiesel that is rich in plant sterol ester.At present, the report that carries out plant sterol ester study on the synthesis is both at home and abroad more, but not yet relates to taking high-acid value greases such as high acid value Rice pollard oil, wheatgerm oils as raw material, and the research report of plant sterol ester biodiesel is rich in preparation.
Summary of the invention
The object of the present invention is to provide a kind of high valent acid vegetable oil that utilizes to produce the method that is rich in plant sterol ester biodiesel, the acid value of high-acid value grease (rice bran wet goods) can obviously fall in the method on the one hand, can generate on the other hand new functional active components---plant sterol ester, product is without auxiliary separation and purification, easy and simple to handle.
For achieving the above object, the technical solution used in the present invention is as follows: a kind of high valent acid vegetable oil that utilizes is produced the method that is rich in plant sterol ester biodiesel, it is characterized in that it comprises the steps:
(1) pre-treatment of raw material: reaction solvent adopts anhydrous sodium sulphate to dewater, 80 DEG C of-120 DEG C of vacuum-drying 8-12h of plant sterol, the moisture content of reaction solvent is controlled at below 0.1wt%, the moisture content of plant sterol is controlled at below 1wt%, and the moisture content of high acid value grease is controlled at below 0.2wt%;
(2) input of reaction raw materials: press plant sterol, the mol ratio of the free fatty acids in high acid value grease is the molecular-weight average of the acid value/2 × free fatty acids of amount of substance (the mole number)=high-acid value grease of 1:1-5:1[free fatty acids], the proportioning of plant sterol and reaction solvent is 100-400mmol:1L, the add-on of molecular sieve is that 100g/L (is in every liter of solvent, to add 100g molecular sieve, also can adopt solventless method, using raw material high-acid value grease as solvent), by plant sterol (100-400mM), high acid value grease (high-acid value grease) (20-400mM), reaction solvent (or solvent-free), molecular sieve (100g/L) adds in reactor, add 100-200ppm antioxidant [being that in solvent (referring to reaction solvent or/and high acid value grease), the concentration of antioxidant is 100-200ppm], being heated to 45-60 DEG C stirs and supersound process, treatment time is 30-60 minute, obtain pre-composition,
(3) enzymatic interesterification procedure: add 5-40g/L lipase (adding 5-40g lipase in every liter of pre-composition) in pre-composition, within the scope of 45-60 DEG C, stirring reaction 6-12h under condition of normal pressure, stops heating, naturally cools to room temperature;
(4) aftertreatment of product: after completion of the reaction, centrifugal lipase, the molecular sieve removed, after being cooled to 4 DEG C, remove by filter unreacted plant sterol, vacuum rotary steam is removed reaction solvent (when reactionless solvent, without vacuum rotary steam), obtain being rich in sterol ester biodiesel (low acid value and be rich in plant sterol ester).
Press such scheme, described plant sterol is that any one or two kinds in Stigmasterol, Sitosterol, brassicasterol, campesterol are above by the mixture of any proportioning.
Press such scheme, described high valent acid vegetable oil comprise acid value between the Rice pollard oil of 20-100mgKOH/g, wheatgerm wet goods vegetables oil any one or more than two kinds by the mixture of any proportioning, do not comprise waste grease.
Press such scheme, described reaction solvent (being the reaction solvent of enzymatic esterification) be normal hexane, octane-iso, hexanaphthene, normal heptane etc. one or two or more kinds by the mixture of any proportioning.Also can adopt solventless method,, using high acid value grease itself as solvent, additionally not add other solvent.
Press such scheme, described lipase (free or immobilized), comprises the candida rugosa lipase, Candida lipalytica Lipase, antarctic candidia lipase or the pseudomonas cepacia lipase that derive from microorganism fermentation.Preferably derive from the lipase of candida rugosa lipase, antarctic candidia lipase or Candida lipolytica.
Press such scheme, described antioxidant is the fat-soluble antioxidants such as natural VE, fat-soluble tea polyphenol or Ascorbyl Palmitate, preferably fat-soluble tea polyphenol.
Press such scheme, the power of described supersound process is 100-300w, and ultrasonic frequency is 25-40Hz.
The present invention is taking the high acid value such as plant sterol and Rice pollard oil, wheatgerm oil vegetables oil as raw material; utilize free fatty acidies a large amount of in high-acid value grease as acry radical donor; employing derives from candiyeast; the lipase of the microorganisms such as the false silk of onion Zymomonas mobilis is catalyzer; by the method for enzymatic esterification; the biodiesel of plant sterol ester is rich in preparation, can effectively reduce the acid value of stock oil simultaneously.By optimizing the conditions such as sterol concentration, temperature of reaction, time, lipase kind and addition, obtain optimal processing parameter.Present method can realize deep processing and the higher value application of the high acid value such as Rice pollard oil, wheatgerm oil vegetables oil, can effectively improve utilization ratio and the added value of high acid value vegetables oil, has reduced loaded down with trivial details chemical deacidification step simultaneously.
Useful result of the present invention is:
1. whole reaction is carried out under low-temperature atmosphere-pressure, and without nitrogen protection, product is difficult for being oxidized, and equipment is simple, easy and simple to handle;
2. a step enzymatic esterification just can obviously reduce the acid value of high acid value vegetables oil, obtains sterol ester active function composition simultaneously; And product is substantially without separation and purification; Reaction conditions gentleness;
3. can produce by the ratio of controlling two kinds of raw materials (plant sterol and high-acid value grease) biodiesel that is rich in different content sterol ester, to be applicable to the needs of variant production;
4. the method has raw material eurytropy, is applicable to Rice pollard oil, the multiple high acid value vegetable oil raw materials of wheatgerm wet goods.
Embodiment
In order to understand better the present invention, further illustrate content of the present invention below in conjunction with embodiment, but content of the present invention is not only confined to the following examples.
Embodiment 1:
Utilize high valent acid vegetable oil to produce a method that is rich in plant sterol ester biodiesel, it comprises the steps:
(1) pre-treatment of raw material: reaction solvent (normal hexane) adopts anhydrous sodium sulphate dewater (moisture <0.1wt%), 80 DEG C of vacuum-drying 12h of Sitosterol (plant sterol) (moisture <1wt%), high-acid value grease adopts Rice pollard oil (moisture <0.2wt%, acid value 20mgKOH/g);
(2) input of reaction raw materials: by 5L normal hexane, 207g plant sterol (Sitosterol, 100mM), Rice pollard oil 1400g (acid value 20mgKOH/g, containing free fatty acids 100mM), (add-on is 50g/L to molecular sieve, be 250g) add in reactor, add natural VE antioxidant 200ppm, (time is 30 minutes to be heated to 45 DEG C of stirrings supersound process, the power of supersound process is 100w, ultrasonic frequency is 25Hz), obtain pre-composition;
(3) enzymatic interesterification procedure: add 25g (5g/L) antarctic candidia lipase, stirring reaction 12h under 45 DEG C of condition of normal pressure, stops heating, naturally cools to room temperature;
(4) aftertreatment of product: after completion of the reaction, centrifugal lipase (antarctic candidia lipase), molecular sieve and the unreacted plant sterol removed, vacuum rotary steam is removed normal hexane, obtains being rich in plant sterol ester biodiesel, and overall yield of reaction is greater than 88%.Wherein plant sterol ester content is greater than 20wt%, and product acid value is less than 5.0mgKOH/g, and peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 2:
Utilize high valent acid vegetable oil to produce a method that is rich in plant sterol ester biodiesel, it comprises the steps:
(1) pre-treatment of raw material: reaction solvent (octane-iso) adopts anhydrous sodium sulphate dewater (moisture <0.1wt%), 100 DEG C of vacuum-drying 10h of Stigmasterol (plant sterol) (moisture <1wt%), wheatgerm oil for high-acid value grease (moisture <0.2wt%, acid value 40mgKOH/g);
(2) input of reaction raw materials: by 5L octane-iso, 414g plant sterol (Stigmasterol 200mM), wheatgerm oil 700g (acid value 40mgKOH/g, containing free fatty acids 100mM), (add-on is 50g/L to molecular sieve, be 250g), add fat-soluble tea polyphenol antioxidant 150ppm, add in reactor, (time is 50 minutes to be heated to 55 DEG C of stirrings supersound process, the power of supersound process is 200w, ultrasonic frequency is 30Hz), obtain pre-composition;
(3) enzymatic interesterification procedure: add 100g (20g/L) antarctic candidia lipase in pre-composition, stirring reaction 10h under 55 DEG C of condition of normal pressure, stops heating, naturally cools to room temperature.
(4) aftertreatment of product: after completion of the reaction, centrifugal lipase (antarctic candidia lipase), molecular sieve and the unreacted plant sterol removed, vacuum rotary steam is removed octane-iso, obtains being rich in plant sterol ester biodiesel, and overall yield of reaction is greater than 85%.Wherein plant sterol ester content is greater than 30wt%, and product acid value is less than 4.5mgKOH/g, and peroxide value is less than 3.0meq/kg.Illustrate that the present invention can obviously reduce wheatgerm oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 3:
Utilize high valent acid vegetable oil to produce a method that is rich in plant sterol ester biodiesel, it comprises the steps:
(1) pre-treatment of raw material: reaction solvent (normal heptane) adopts anhydrous sodium sulphate dewater (moisture <0.1wt%), 120 DEG C of vacuum-drying 8h of brassicasterol (moisture <wt%), high-acid value grease adopts Rice pollard oil (moisture <0.2wt%, acid value is 100mgKOH/g);
(2) input of reaction raw materials: by 5L normal heptane, 828g plant sterol (brassicasterol 400mM), Rice pollard oil 280g (acid value 100mgKOH/g, fatty acids 80mM), (add-on is 50g/L to molecular sieve, be 250g), add L Quicifal antioxidant 200ppm, add in reactor, (time is 60 minutes to be heated to 60 DEG C of stirrings supersound process, the power of supersound process is 300w, ultrasonic frequency is 40Hz), obtain pre-composition;
(3) enzymatic interesterification procedure: add 200g (40g/L) Candida lipalytica Lipase in pre-composition, stirring reaction 12h under 60 DEG C of condition of normal pressure, stops heating, naturally cools to room temperature.
(4) aftertreatment of product: after completion of the reaction, centrifugal lipase (Candida lipalytica Lipase), molecular sieve and the unreacted plant sterol removed, vacuum rotary steam is removed normal heptane, obtains being rich in plant sterol ester biodiesel, and overall yield of reaction is greater than 84%.Wherein plant sterol ester content is greater than 50%, and product acid value is less than 4.0mgKOH/g, and peroxide value is less than 4.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 4 (not adding solvent, taking Rice pollard oil as solvent):
Utilize high valent acid vegetable oil to produce a method that is rich in plant sterol ester biodiesel, it comprises the steps:
(1) pre-treatment of raw material: 80 DEG C of vacuum-drying 12h of campesterol (plant sterol) (moisture <1wt%), high-acid value grease adopts Rice pollard oil (moisture <0.2wt%, acid value 20mgKOH/g);
(2) input of reaction raw materials: by 207g campesterol (100mM), Rice pollard oil 700g (acid value 20mgKOH/g, fatty acids 50mM), (add-on is 50g/L to molecular sieve, be 250g) add in reactor, add natural VE antioxidant 200ppm, (time is 30 minutes to be heated to 50 DEG C of stirrings supersound process, the power of supersound process is 200w, and ultrasonic frequency is 25-40Hz), obtain pre-composition;
(3) enzymatic interesterification procedure: add 25g (5g/L) antarctic candidia lipase, stirring reaction 12h under 50 DEG C of condition of normal pressure, stops heating, naturally cools to room temperature;
(4) aftertreatment of product: after completion of the reaction, centrifugal lipase, molecular sieve and the unreacted plant sterol removed, obtains being rich in plant sterol ester biodiesel, and overall yield of reaction is greater than 85%.Wherein sterol ester content is greater than 30wt%, and acid value is less than 4.0mgKOH/g, and peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 5:
Substantially the same manner as Example 2, difference is in step (1): plant sterol is the mixture of Stigmasterol and Sitosterol, and the quality of Stigmasterol and Sitosterol respectively accounts for 1/2; Obtain being rich in plant sterol ester biodiesel, overall yield of reaction is greater than 86%.Wherein plant sterol ester content is greater than 30wt%, and acid value is less than 5.0mgKOH/g, and peroxide value is less than 4.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 6:
Substantially the same manner as Example 3, difference is: antarctic candidia lipase is substituted by candida rugosa lipase; Natural VE antioxidant changes 100ppm into; Obtain being rich in plant sterol ester biodiesel, overall yield of reaction is greater than 85%.Wherein plant sterol ester content is greater than 50wt%.Acid value is less than 6.0mgKOH/g, and peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 7:
Substantially the same manner as Example 3, difference is: antarctic candidia lipase is substituted by pseudomonas cepacia lipase; Rice pollard oil changes Rice pollard oil and wheatgerm oil into, and the quality of Rice pollard oil, wheatgerm oil respectively accounts for 1/2; The biodiesel that obtains being rich in plant sterol ester, overall yield of reaction is greater than 85%.Wherein plant sterol ester content is greater than 50wt%, and acid value is less than 5.0mgKOH/g, and peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 8:
Substantially the same manner as Example 3, difference is: antarctic candidia lipase is substituted by pseudomonas cepacia lipase; Rice pollard oil changes Rice pollard oil and wheatgerm oil into, and the quality of Rice pollard oil, wheatgerm oil respectively accounts for 1/2; The biodiesel that obtains being rich in plant sterol ester, overall yield of reaction is greater than 85%.Wherein plant sterol ester content is greater than 50wt%, and acid value is less than 5.0mgKOH/g, and peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Embodiment 9:
Substantially the same manner as Example 1, difference is: high-acid value grease adopts Rice pollard oil (moisture <0.2wt%, acid value 20mgKOH/g) and wheatgerm oil (moisture <0.2wt%, acid value 100mgKOH/g), the quality of Rice pollard oil and wheatgerm oil respectively accounts for 1/2; Obtain being rich in plant sterol ester biodiesel, overall yield of reaction is greater than 88%.Wherein plant sterol ester content is greater than 20wt%, and product acid value is less than 6.0mgKOH/g, and peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Rice pollard oil acid value and obtain the biodiesel that is rich in plant sterol ester.
Each raw material that the present invention is cited, and the bound of the each raw material of the present invention, interval value, and the bound of processing parameter (as temperature, time etc.), interval value can realize the present invention, do not enumerate embodiment at this.
Claims (9)
1. utilize high valent acid vegetable oil to produce a method that is rich in plant sterol ester biodiesel, it is characterized in that it comprises the steps:
(1) input of reaction raw materials: be 1:1-5:1 by the mol ratio of the free fatty acids in plant sterol, high acid value grease, the add-on of molecular sieve is 100g/L, plant sterol, high acid value grease, molecular sieve are added in reactor, add 100-200ppm antioxidant, being heated to 45-60 DEG C stirs and supersound process, treatment time is 30-60 minute, obtains pre-composition;
(2) enzymatic interesterification procedure: add 5-40g/L lipase in pre-composition, within the scope of 45-60 DEG C, stirring reaction 6-12h under condition of normal pressure, stops heating, naturally cools to room temperature;
(3) aftertreatment of product: after completion of the reaction, centrifugal lipase, the molecular sieve removed, removes by filter unreacted plant sterol after being cooled to 4 DEG C, obtains being rich in plant sterol ester biodiesel.
2. a kind of high valent acid vegetable oil that utilizes according to claim 1 is produced the method that is rich in plant sterol ester biodiesel, it is characterized in that: the raw material in step (1) needs pre-treatment: 80 DEG C of-120 DEG C of vacuum-drying 8-12h of plant sterol, the moisture content of plant sterol is controlled at below 1wt%, and the moisture content of high acid value grease is controlled at below 0.2wt%.
3. a kind of high valent acid vegetable oil that utilizes according to claim 1 is produced the method that is rich in plant sterol ester biodiesel, it is characterized in that: step (1) Raw also comprises reaction solvent, the proportioning of plant sterol and reaction solvent is 100-400mmol:1L, and reaction solvent adds in reactor together with plant sterol, high acid value grease, molecular sieve; Reaction solvent adopts anhydrous sodium sulphate to dewater, and the moisture content of reaction solvent is controlled at below 0.1wt%; In step (3), vacuum rotary steam is removed reaction solvent.
4. a kind of high valent acid vegetable oil that utilizes according to claim 1 is produced the method for plant sterol ester biodiesel of being rich in, and it is characterized in that: described plant sterol is that any one or two kinds in Stigmasterol, Sitosterol, brassicasterol, campesterol are above by the mixture of any proportioning.
5. a kind of high valent acid vegetable oil that utilizes according to claim 1 is produced the method that is rich in plant sterol ester biodiesel, it is characterized in that: described high valent acid vegetable oil comprise acid value between the Rice pollard oil of 20-100mgKOH/g, wheatgerm wet goods vegetables oil any one or more than two kinds by the mixture of any proportioning, do not comprise waste grease.
6. a kind of high valent acid vegetable oil that utilizes according to claim 3 is produced the method for plant sterol ester biodiesel of being rich in, and it is characterized in that: described reaction solvent be normal hexane, octane-iso, hexanaphthene, normal heptane etc. one or two or more kinds by the mixture of any proportioning.
7. a kind of high valent acid vegetable oil that utilizes according to claim 1 is produced the method that is rich in plant sterol ester biodiesel, it is characterized in that: described lipase can be free or immobilized form, comprise the candida rugosa lipase, Candida lipalytica Lipase, antarctic candidia lipase or the pseudomonas cepacia lipase that derive from microorganism fermentation.
8. a kind of high valent acid vegetable oil that utilizes according to claim 1 is produced the method that is rich in plant sterol ester biodiesel, it is characterized in that: described antioxidant is natural VE, fat-soluble tea polyphenol or Ascorbyl Palmitate.
9. a kind of high valent acid vegetable oil that utilizes according to claim 1 is produced the method that is rich in plant sterol ester biodiesel, it is characterized in that: the power of described supersound process is 100w-300w, and ultrasonic frequency is 25-40Hz.
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| CN114736739A (en) * | 2022-03-21 | 2022-07-12 | 中国农业科学院油料作物研究所 | Method for deacidifying by lipid enzyme method and synchronously preparing functional lipid |
| CN114736739B (en) * | 2022-03-21 | 2023-08-25 | 中国农业科学院油料作物研究所 | Method for synchronously preparing deacidification and functional lipid by using oil enzymatic method |
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