CN111394403B - Preparation method and application of fatty acid glycerol mixed ester - Google Patents
Preparation method and application of fatty acid glycerol mixed ester Download PDFInfo
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- CN111394403B CN111394403B CN202010190307.8A CN202010190307A CN111394403B CN 111394403 B CN111394403 B CN 111394403B CN 202010190307 A CN202010190307 A CN 202010190307A CN 111394403 B CN111394403 B CN 111394403B
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- 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
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- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
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- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
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- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
- A23L3/3517—Carboxylic acid esters
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Abstract
The invention discloses a preparation method and application of fatty acid glycerol mixed ester, wherein the preparation method comprises the following steps: s1, heating the fatty acid, adding glycerol, tert-butyl alcohol and cyclodextrin, performing ultrasonic treatment, cooling and filtering to obtain an esterification reaction substrate; s2, adding lipase into the esterification reaction substrate obtained in the step S1, and stirring in vacuum to obtain the fatty acid glycerol mixed ester. The application is the application of the prepared fatty acid glycerol mixed ester in food. The invention greatly shortens the esterification reaction time, improves the conversion rate of fatty acid, saves the separation refining process, reduces the production cost, is suitable for industrial production, and simultaneously, the prepared fatty acid glycerol mixed ester can be directly used as a food emulsifier, improves the quality of food, has the antibacterial effect and prolongs the shelf life of the food.
Description
Technical Field
The invention relates to the technical field of food additives, in particular to a preparation method and application of fatty acid glycerol mixed ester.
Background
The fatty acid monoglyceride is called as monoglyceride for short, is a polyhydric alcohol type nonionic surfactant, is used as an excellent W/O type emulsifier, has an amphiphilic molecular structure, and consists of a lipophilic group and a hydrophilic group, wherein the lipophilic group consists of fatty acid and the hydrophilic group consists of glyceryl. The amphiphilic molecular structure is a precondition for generating surface activity, and enables the fatty acid monoglyceride to be easily enriched on the surface of a solution to be adsorbed, and the fatty acid monoglyceride and the monoglyceride are directionally arranged on the surface and the interface to generate the surface activity and the interface activity, so that the surface or interface tension is reduced. In view of the good surface activity of the fatty acid monoglyceride, the fatty acid monoglyceride is widely applied to food, cosmetic and pharmaceutical industries as an emulsifier, and has huge demand and wide market prospect.
At present, the fatty acid monoglyceride produced industrially is mainly prepared by a glycerolysis method, namely, the glycerol and animal and vegetable oil are subjected to glycerolysis reaction at a high temperature (220-260 ℃) in the presence of an alkali catalyst. The method has high reaction temperature, large energy consumption and more side reactions, the obtained product is a mixture of fatty acid monoglyceride, diglyceride and triglyceride, and the content of monoglyceride is about 50 percent generally. The method for preparing the fatty acid monoglyceride by the enzyme catalysis method has the advantages of mild reaction conditions, high selectivity and good product quality, and is a research hotspot which is widely concerned by scientists.
A process for preparing glyceride includes such steps as mixing glycerine with fatty acid, reaction at 100 deg.C with lipase Novozym 435 for 8 hr, steam distilling at 240 deg.C until the acid value of product is reduced to 5.0mg/g, stopping heating, cooling, water washing and dewatering to obtain the mixture of monoglyceride, diglyceride and triglyceride, in which the monoglyceride content is 40%.
Royal jelly and the like (enzymatic synthesis and characterization of fatty acid monoglyceride, food and fermentation industry, vol 43, 5 in 2017) respectively take methyl decanoate, methyl laurate, methyl myristate, methyl palmitate and methyl stearate as raw materials, tert-butyl alcohol as a reaction solvent, and the raw materials and glycerol are subjected to transesterification reaction under the catalysis of immobilized lipase to prepare corresponding fatty acid monoglyceride, and the obtained product is a mixture of fatty acid monoglyceride and a small amount of fatty acid diglyceride, wherein the mass fraction of the fatty acid monoglyceride is more than 91%, but the conversion rate of the raw material fatty acid methyl ester is low and is only 69.2-76.2%.
Therefore, a preparation method of food-grade fatty acid glycerol mixed ester, which has high conversion rate and is suitable for industrial production, is urgently needed.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method and application of fatty acid glycerol mixed ester, which has the advantages of mild production conditions, low cost and high raw material conversion rate and is suitable for industrial production.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing fatty acid glycerol mixed ester comprises the following steps:
s1, heating the fatty acid, adding glycerol, tert-butyl alcohol and cyclodextrin, performing ultrasonic treatment, cooling and filtering to obtain an esterification reaction substrate;
s2, adding lipase into the esterification reaction substrate obtained in the step S1, and stirring in vacuum to obtain the fatty acid glycerol mixed ester.
Preferably, the fatty acid in step S1 is at least one of caprylic acid, capric acid, myristic acid and stearic acid; further preferably, capric acid and myristic acid are present in a mass ratio of 2: 1.
Preferably, the temperature rise in step S1 is heating the fatty acid to 60-70 ℃.
Preferably, the mass ratio of the fatty acid, the glycerol, the tert-butyl alcohol and the cyclodextrin in the step S1 is 1-2: 1: 1:0.3-0.5.
Preferably, the ultrasound treatment in step S1 is performed at 500-600kw for 10-20 min.
Preferably, the temperature reduction in step S1 is to 45-50 ℃.
Preferably, the filtration in step S1 is through a 0.45 micron cellulose acetate membrane.
Preferably, the lipase in step S2 is Novozym 435 lipase.
Preferably, the lipase is added in step S2 in an amount of 1.0-1.5% by mass of the fatty acid.
Preferably, the vacuum stirring in step S2 is: stirring at 45-50 deg.C under vacuum of 80-90Pa for 3-5 h.
The invention also provides application of the fatty acid glycerol mixed ester prepared by the preparation method in food.
Including but not limited to bread, dairy products, beverages, and the like.
The invention has the beneficial effects that:
(1) the method takes fatty acid and glycerol as raw materials, takes tert-butyl alcohol and cyclodextrin as solvents, and synthesizes fatty glyceride through esterification reaction under the action of lipase after ultrasonic pretreatment and filtration, so that the reaction time is shortened to 3-5h, the reaction time is greatly shortened, and the reaction efficiency is improved.
(2) The conversion rate of the fatty acid is high, the content of the fatty glyceride in the reactant is 95%, the fatty glyceride can be directly used for food emulsifiers, the separation and refining process is saved, the production cost is reduced, and the method is suitable for industrial production.
(3) The fatty acid glycerol mixed ester prepared by the invention can improve the quality of bread, has an antibacterial effect and can prolong the shelf life of food.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The sources of the raw materials used in the present invention are not limited, and the raw materials used in the present invention are all those commonly available in the art unless otherwise specified. The filter membrane used in this example was a cellulose acetate filter membrane.
Example 1
A method for preparing fatty acid glycerol mixed ester comprises the following steps:
s1, heating myristic acid to 60 ℃, adding glycerol, tert-butyl alcohol and cyclodextrin, performing ultrasonic treatment for 10min at 600kw, cooling to 50 ℃, and filtering through a 0.45-micron filter membrane to obtain an esterification reaction substrate;
the mass ratio of the fatty acid to the glycerol to the tert-butyl alcohol to the cyclodextrin is 1: 1: 0.3;
s2, adding Novozym 435 lipase into the esterification reaction substrate obtained in the step S1, and stirring for 5 hours at the temperature of 45 ℃ under the vacuum condition of 80Pa to obtain the fatty acid glycerol mixed ester;
the addition amount of the lipase is 1.5 percent of the mass of the fatty acid.
Example 2
A method for preparing fatty acid glycerol mixed ester comprises the following steps:
s1, heating the capric acid to 70 ℃, adding glycerol, tert-butyl alcohol and cyclodextrin, performing ultrasonic treatment for 20min at 500kw, cooling to 45 ℃, and filtering with a 0.45-micron filter membrane to obtain an esterification reaction substrate;
the mass ratio of the fatty acid to the glycerol to the tert-butyl alcohol to the cyclodextrin is 2: 1: 1: 0.5;
s2, adding Novozym 435 lipase into the esterification reaction substrate obtained in the step S1, and stirring for 3 hours at the temperature of 50 ℃ under the vacuum condition of 90Pa to obtain the fatty acid glycerol mixed ester;
the addition amount of the lipase is 1.0 percent of the mass of the fatty acid.
Example 3
A method for preparing fatty acid glycerol mixed ester comprises the following steps:
s1, heating the octanoic acid to 65 ℃, adding glycerol, tert-butyl alcohol and cyclodextrin, performing ultrasonic treatment for 15min at 550kw, cooling to 48 ℃, and filtering with a 0.45-micron filter membrane to obtain an esterification reaction substrate;
the mass ratio of the fatty acid to the glycerol to the tert-butyl alcohol to the cyclodextrin is 1.5: 1: 1: 0.4;
s2, adding Novozym 435 lipase into the esterification reaction substrate obtained in the step S1, and stirring for 4 hours at the temperature of 48 ℃ under the vacuum condition of 85Pa to obtain the fatty acid glycerol mixed ester;
the addition amount of the lipase is 1.2 percent of the mass of the fatty acid.
Example 4
A method for preparing fatty acid glycerol mixed ester comprises the following steps:
s1, heating capric acid and myristic acid in a mass ratio of 2:1 to 62 ℃, adding glycerol, tert-butyl alcohol and cyclodextrin, performing ultrasonic treatment for 18min at 520kw, cooling to 46 ℃, and filtering with a 0.45-micron filter membrane to obtain an esterification reaction substrate;
the mass ratio of the fatty acid to the glycerol to the tert-butyl alcohol to the cyclodextrin is 1.3: 1: 1: 0.35;
s2, adding Novozym 435 lipase into the esterification reaction substrate obtained in the step S1, and stirring for 4.8 hours at the temperature of 46 ℃ under the vacuum of 88Pa to obtain the fatty acid glycerol mixed ester;
the addition amount of the lipase is 1.1 percent of the mass of the fatty acid.
Example 5
This example differs from example 4 in that the fatty acids are myristic acid and stearic acid in a mass ratio of 1: 1.
Comparative example 1
This comparative example differs from example 4 in the absence of cyclodextrin.
Comparative example 2
This comparative example differs from example 4 in the absence of t-butanol.
Comparative example 3
This comparative example differs from example 4 in that conventional electromagnetic stirring was used instead of sonication.
Comparative example 4
This comparative example differs from example 4 in the absence of a filtration step.
The conversion rates of the fatty acids and the mass fractions of the fatty acid monoglyceride, fatty acid diglyceride, and fatty acid triglyceride obtained by detecting the products of examples 1 to 5 and comparative examples 1 to 4 by liquid chromatography are shown in table 1.
TABLE 1
Application effect experiment in bread:
the fatty acid glycerol mixed ester prepared in the examples 1-5 and the comparative examples 1-4 is added into flour according to the mass percent of 0.1%, and the bread is prepared according to the formula of GB/T14611-2008 'direct fermentation method for testing baking quality of wheat flour and bread by grain and oil test'. Loosening dough at room temperature for 20min, cutting into pieces, kneading dough, shaping, placing into bread mold, fermenting in a fermenting box with temperature of 30 deg.C and humidity of 85% for 90min, baking for 12min (upper fire 210 deg.C and lower fire 200 deg.C), cooling in aseptic operation table for 1h, packaging into food-grade sealed packaging bag, and testing.
Bread samples cooled for 1h in an aseptic worktop were taken and measured for volume and mass according to the method for volume replacement in reference GB/T20981-2007 bread. The calculation was performed as follows, with 3 replicates per sample, and the average was taken, where the bread specific volume P is volume (mL)/mass (g).
Placing the cooled and packaged bread in a constant temperature and humidity maintaining fermentation box (30 deg.C, humidity 70%), measuring the total bacterial colony growth of bread stored for 2, 4 and 6 days during storage period, and measuring according to the method of GB 4789.2-2016 (food microbiology test bacterial colony total determination), wherein the total bacterial colony of bread is less than 104The storage time of CFU/g is the shelf life. The results of the experiment are shown in table 2.
TABLE 2
As can be seen from Table 2, the fatty acid glycerol mixed esters prepared in examples 1 to 4 of the present invention can increase bread specific volume, improve bread quality, and at the same time, can inhibit bacterial growth and prolong shelf life.
In conclusion, the fatty acid glyceride is synthesized by taking fatty acid and glycerol as raw materials and tert-butyl alcohol and cyclodextrin as solvents through esterification reaction under the action of lipase after ultrasonic pretreatment and filtration, so that the reaction time is shortened to 3-5h, the reaction time is greatly shortened, and the reaction efficiency is improved;
the conversion rate of the fatty acid is high, and the content of the fatty glyceride in the reactant is 95%, so that the fatty glyceride can be directly used for food emulsifiers, a separation and refining process is saved, the production cost is reduced, and the method is suitable for industrial production;
the fatty acid glycerol mixed ester prepared by the invention can improve the quality of bread, has an antibacterial effect and can prolong the shelf life of food.
The present invention has been further described with reference to specific embodiments, which are only exemplary and do not limit the scope of the present invention. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be made without departing from the spirit and scope of the invention.
Claims (6)
1. A method for preparing fatty acid glycerol mixed ester is characterized by comprising the following steps:
s1, heating the fatty acid, adding glycerol, tert-butyl alcohol and cyclodextrin, performing ultrasonic treatment, cooling and filtering to obtain an esterification reaction substrate;
the mass ratio of the fatty acid to the glycerol to the tert-butyl alcohol to the cyclodextrin is 1.3: 1: 0.35;
the fatty acid is capric acid and myristic acid with the mass ratio of 2: 1;
the temperature is reduced to 46 ℃;
s2, adding lipase into the esterification reaction substrate obtained in the step S1, and stirring in vacuum to obtain the fatty acid glycerol mixed ester;
the lipase is Novozym 435 lipase;
the addition amount of the lipase is 1.1 percent of the mass of the fatty acid.
2. The method according to claim 1, wherein the temperature rise in step S1 is heating the fatty acid to 60 to 70 ℃.
3. The method as claimed in claim 1, wherein the sonication in step S1 is sonication at 600kw for 10-20min at 500-.
4. The method according to claim 1, wherein the filtration in step S1 is a 0.45 μm cellulose acetate membrane.
5. The method of claim 1, wherein the vacuum stirring in step S2 is: stirring at 45-50 deg.C under vacuum of 80-90Pa for 3-5 h.
6. Use of the fatty acid glycerol mixed ester produced by the production method according to any one of claims 1 to 5 in food.
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