CN111471529B - Glycerol esterification method for high acid value oil - Google Patents
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- CN111471529B CN111471529B CN202010190259.2A CN202010190259A CN111471529B CN 111471529 B CN111471529 B CN 111471529B CN 202010190259 A CN202010190259 A CN 202010190259A CN 111471529 B CN111471529 B CN 111471529B
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
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- Chemical Kinetics & Catalysis (AREA)
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- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention provides a glycerol esterification method for high-acid-value grease, which comprises the following specific steps: mixing and heating glycerin, monoglyceride, a targeting inducer and high-acid-value grease under a vacuum condition to perform esterification reaction to obtain esterified grease; wherein the mass of the targeted inducer accounts for 0.1-5% of the mass of the high acid value grease; the mass of the glycerol accounts for 1-50% of that of the high-acid-value oil, and the mass of the monoglyceride is 1-10 times of that of the glycerol. According to the invention, through the synergistic effect of glycerol, monoglyceride and a targeted inducer, in the field of edible oil, the original oil characteristics can be improved, and the nutritional value can be improved, and in the field of biodiesel, the saturated fatty acid and the unsaturated fatty acid of the raw materials are separated through conventional physical means such as winterization and fractionation, so that the classification of the characteristics of the raw materials is realized, and the diversity of products can be enriched.
Description
Technical Field
The invention relates to the technical field of oil refining, in particular to a method for esterifying high-acid-value oil by glycerol.
Background
In the field of edible oil, alkali refining deacidification is generally adopted, but for high-acid-value oil with an acid value of more than 10mgKOH/g, the oil loss is large and the refining rate is low, so the alkali refining deacidification is not suitable for deacidification of the high-acid-value oil. Aiming at the problem of reducing the acid value of high acid value oil in the field of edible oil and high acid value raw oil in the field of biodiesel, the purpose of deacidifying the high acid value oil is mainly realized by a glycerol esterification process at present, but the process cannot selectively combine saturated fatty acid, unsaturated fatty acid and glycerol, so that the generated triglyceride contains a plurality of types of acylated fatty acid and the acylated fatty acid is completely distributed in the triglyceride without regularity, and the difficulty in subsequently classifying the triglyceride is high.
Disclosure of Invention
The invention aims to provide a method for esterifying high-acid-value oil and fat by glycerol aiming at the defects of the prior art.
In order to achieve the purpose, the invention adopts the technical scheme that: a glycerol esterification method for high-acid-value oil comprises the following specific steps: mixing and heating glycerin, monoglyceride, a targeting inducer and high-acid-value grease under a vacuum condition to perform esterification reaction to obtain esterified grease;
wherein the mass of the targeted inducer accounts for 0.1-5% of the mass of the high acid value grease; the mass of the glycerol accounts for 1-50% of that of the high acid value oil, the mass of the monoglyceride is 1-10 times of that of the glycerol, and the high acid value oil refers to oil with an acid value of more than 10 mgKOH/g.
Based on the above, the targeting inducer is CH 3 COOK、CH 3 COONa、AlCl 3 ·6H 2 O、Al 2 O 3 、SnO 2 、SbCl 2 、HgCl 2 、FeO、NiCl 2 ·6H 2 O、NaOH、MgCl 2 ·6H 2 O、MgO、MnCl 2 ·4H 2 O、PbCl 2 、ZnO、FeCl 3 ·6H 2 O、CdCl 2 ·2.5H 2 O、PbO、MnO 2 、ZnCl 2 、SnCl 2 ·2H 2 O、SnCl 4 ·5H 2 And O or a mixture of more than one of O.
Based on the above, the monoglyceride is one or a mixture of glycerol monolaurate, glycerol monomyristate, glycerol monopalmitate, glycerol monostearate, glycerol monooleate, glycerol monolinoleate, glycerol monolinolenate and glycerol monoarachidate.
Based on the above, the temperature for mixing, heating and esterifying glycerol, monoglyceride, a targeting inducer and high-acid-value grease under the vacuum condition is 100-300 DEG C
In the method for esterifying the high-acid-value oil by using the glycerol, the monoglyceride and the targeting inducer, free saturated fatty acids and free unsaturated fatty acids in the glycerol and the high-acid-value oil can be selectively combined to generate the glycerol esters with three same acylated fatty acids, such as tripalmitin, triolein and the like.
The specific reaction scheme is as follows:
formula 1:
formula 2:
formula 3:
formula 4:
wherein R is 1 ，R 2 ，R 3 Representing different types of fatty acid molecules.
Formula 1 is the triglyceride formula.
Formula 2 glycerylation equation.
Formula 3 is the monoglyceride esterification equation.
Equation 4 is the molecular structure reforming equation for triglycerides.
In addition, through the synergistic action of glycerol, monoglyceride and a targeting inducer, the fatty acid bound to the original triglyceride molecule in the high-acid-value oil can be subjected to directional rearrangement, and glycerides having three identical acylated fatty acids, such as tripalmitin and triolein, can be similarly produced.
Compared with the prior art, the method has outstanding substantive characteristics and remarkable progress, and particularly has the following advantages:
(1) Since a triglyceride consists of 1 molecule of glycerol and 3 molecules of fatty acids, the combination of 3 hydroxyl groups of glycerol with different fatty acids may yield many different molecules of triacylglycerol. The fatty acid distribution in the natural oil triacylglycerol rarely contains three identical acylated fatty acids but consists of a plurality of different fatty acids. According to the high-acid-value oil glyceride esterification method provided by the invention, by utilizing the synergistic effect of the glycerol, the monoglyceride and the targeting inducer, the glycerol can be selectively combined with free saturated fatty acid and free unsaturated fatty acid in the high-acid-value oil to generate the glycerol esters with three same acylated fatty acids, such as tripalmitin, triolein and the like.
In addition, by utilizing the synergistic effect of glycerol, monoglyceride and a targeting inducer, the fatty acids bound to the original triglyceride molecules in the high-acid-value fat can be subjected to directional rearrangement, and glycerides having three identical acylated fatty acids, such as tripalmitin and triolein, can be similarly produced. Because the glyceride has three same acylated fatty acids, the subsequent classification can be further purified and classified according to the types of the acylated fatty acids, and a good foundation is laid for the subsequent improvement of the product quality.
Therefore, for edible oil and fat, the position distribution of fatty acid in triglyceride is an important factor influencing the nutrition of oil and fat, and the position distribution of fatty acid in triglyceride determines the absorption and metabolism of triglyceride and the application value of oil and fat. From the absorption point of view, the triglyceride absorption and digestion of different fatty acid compositions are different in human body, such as unsaturated fatty acid, medium-chain fatty acid which is more easily absorbed than long-chain saturated fatty acid, and fatty acid at Sn-2 position which is more easily absorbed than fatty acid at Sn-1,3. According to the scheme, the content of unsaturated fatty acid and saturated fatty acid distributed on the Sn-2 site and the Sn-1,3 site can be directionally changed through the synergistic effect of glycerol, monoglyceride and the targeting inducer, so that long-chain saturated fatty acid which is difficult to absorb is selectively and more combined on the Sn-2 site which is easier to absorb, the original oil characteristics are improved, and the nutritional value is improved. And for waste oil such as kitchen waste oil for producing biodiesel, the like nature of saturated fatty acid and unsaturated fatty acid can be automatically classified and gathered through the synergistic effect of glycerol, monoglyceride and a targeting inducer, namely, most of triglyceride of one type is combined with the unsaturated fatty acid, and most of triglyceride of the other type is combined with the saturated fatty acid, so that feasibility is provided for the multi-field application of the biodiesel at the source. Before raw oil enters a production system, separation of saturated fatty acid and unsaturated fatty acid can be realized through conventional winterization and fractionation, grading of raw material characteristics is realized, and diversity of products can be enriched.
Detailed Description
The technical solution of the present invention is further described in detail by the following embodiments.
Example 1
The embodiment provides a glycerol esterification method for high-acid-value grease, which comprises the following specific steps:
adding 1000kg of high acid value rice bran oil into a reactor, wherein the acid value is 23.4mgKOH/g, and the addition amount of glycerol is 27kg; the monoglyceride is glycerol monooleate, the addition amount of glycerol monooleate is 27kg, and the targeting inducer is CH 3 COOK+ZnO+SnO 2 The addition amount of the targeting inducer is 1kg. Then, a vacuum pump is started to keep the vacuum degree in the reactor at-0.08 MPa, the reaction temperature is 210 ℃, and the reaction time is 4 hours. After the reaction, the acid value was measured and found to be 2.3mgKOH/g.
And (3) determining the fatty acid position distribution of the high-acid-value rice bran oil by adopting Ultra Performance Liquid Chromatography (UPLC).
The determination steps are as follows: partially hydrolyzing triglyceride by using Sn-1,3 site specific lipase to form a free fatty acid and glyceride mixture, and directly derivatizing the free fatty acid in the mixture by using 2-bromoacetophenone to form phenylacetyl methyl ester; and saponifying the other mixture to extract free fatty acid and performing derivatization reaction.
The UPLC analysis shows that the unsaturated fatty acids (C18: 1, C18: 2) in the high acid value rice bran oil triglyceride are distributed more on the Sn-2 position than on the Sn-1,3 position, while the saturated fatty acids (C16: 0, C18: 0) are distributed less on the Sn-2 position, and are mainly distributed on the Sn-1,3 position.
After the reaction, UPLC analysis determines that the unsaturated fatty acids (C18: 1, C18: 2) in the esterified triglyceride of rice bran oil are distributed on the Sn-2 position and the Sn-1,3 in the same proportion, and the saturated fatty acids (C16: 0, C18: 0) are distributed on the Sn-2 position and the Sn-1,3 in the same proportion.
Therefore, the content of unsaturated fatty acid and saturated fatty acid distributed on the Sn-2 site and the Sn-1,3 site can be directionally changed through the synergistic effect of glycerol, monoglyceride and the targeting inducer, so that the original oil characteristics are improved, and the nutritional value is improved.
Example 2
The embodiment provides a glycerol esterification method for high-acid-value grease, which specifically comprises the following steps:
adding 1000kg of high acid value rice bran oil into a reactor, wherein the acid value is 23.4mgKOH/g, and the addition amount of glycerol is 100kg; the monoglyceride is glycerol monolaurate, the addition amount of glycerol monolaurate is 100kg, and the targeting inducer is CH 3 COOK+CH 3 COONa+AlCl 3 ·6H 2 O, the addition amount of the targeting inducer is 10kg. Then, a vacuum pump is started to keep the vacuum degree in the reactor at-0.08 MPa, the reaction temperature is 205 ℃, and the reaction time is 4 hours. After the reaction, the acid value was measured and found to be 2.4mgKOH/g.
And (3) determining the fatty acid position distribution of the high-acid-value rice bran oil by adopting Ultra Performance Liquid Chromatography (UPLC).
The determination steps are as follows: partially hydrolyzing triglyceride by using Sn-1,3 position specific lipase to form a free fatty acid and glyceride mixture, and then directly derivatizing the free fatty acid in the mixture by using 2-bromoacetophenone to form phenylacetyl methyl ester; and saponifying the other mixture to extract free fatty acid and performing derivatization reaction.
The UPLC analysis determined that the unsaturated fatty acids (C18: 1, C18: 2) in the high acid number bran oil triglyceride distributed more to the Sn-2 position than to the Sn-1,3 position, while the saturated fatty acids (C16: 0, C18: 0) distributed less to the Sn-2 position, primarily to the Sn-1,3 position.
After the reaction, UPLC analysis determines that the unsaturated fatty acids (C18: 1, C18: 2) in the esterified triglyceride of rice bran oil are distributed on the Sn-2 position and the Sn-1,3 in the same proportion, and the saturated fatty acids (C16: 0, C18: 0) are distributed on the Sn-2 position and the Sn-1,3 in the same proportion.
Therefore, the content of unsaturated fatty acid and saturated fatty acid distributed on the Sn-2 site and the Sn-1,3 site can be directionally changed through the synergistic effect of the glycerol, the monoglyceride and the targeting inducer, so that the original oil characteristics are improved, and the nutritional value is improved.
Example 3
The embodiment provides a glycerol esterification method for high-acid-value grease, which comprises the following specific steps:
adding 1000kg of high-acid-value kitchen waste oil into a reactor, wherein the acid value is 80mgKOH/g, the addition amount of glycerol is 382kg, monoglyceride is glycerol monopalmitate, the addition amount of glycerol monopalmitate is 764kg, and a targeted inducer is PbO + PbCl 2 +MnO 2 +Al 2 O 3 The amount of the target inducer added was 2kg. And starting a vacuum pump to keep the vacuum degree in the reactor at-0.09 MPa, the reaction temperature at 200 ℃ and the reaction time at 6h. After the reaction, the acid value was measured and found to be 1.1mgKOH/g.
The method for measuring the fatty acid position distribution of the kitchen waste oil is the same as that in example 1.
The measurement results show that 50% of unesterified high acid value kitchen waste oil is distributed at Sn-2 position by C18. The distribution ratios of the C16:0 acid at the Sn-1, sn-2 and Sn-3 positions are also substantially equivalent. Namely, the content of triolein was 49% and the content of tripalmitin was 23%.
The oil was cooled to 0 ℃ for 6h and then filtered to obtain two main types of triglycerides, namely triolein and tripalmitin. The triolein is subjected to subsequent ester exchange reaction to obtain the biodiesel, and the biodiesel with the property can be used as fuel and is an ideal raw material for producing epoxy resin by deep processing.
The tripalmitin is subjected to subsequent ester exchange reaction to obtain the biodiesel, and the biodiesel with the property can be used as fuel and is an ideal raw material for producing fatty alcohol by deep processing. The purposes of the kitchen waste oil on the raw material layer are subdivided, and the adaptability of the market is stronger.
Example 4
The embodiment provides a glycerol esterification method for high-acid-value grease, which comprises the following specific steps:
adding 1000kg of high-acid-value kitchen waste oil into a reactor, wherein the acid value is 80mgKOH/g, the addition amount of glycerol is 200kg, monoglyceride is glycerol mono-myristate, the addition amount of glycerol mono-myristate is 400kg, and a targeting inducer is NiCl 2 ·6H 2 O+NaOH+MgCl 2 ·6H 2 O, the addition amount of the targeting inducer is 10kg. And starting a vacuum pump to keep the vacuum degree in the reactor at-0.09 MPa, the reaction temperature at 200 ℃ and the reaction time at 6h.
After the reaction, the acid value was measured and found to be 1.2mgKOH/g.
The method for measuring the fatty acid position distribution of the kitchen waste oil is the same as that in example 1.
The measurement results showed that the high acid value kitchen waste oil 50% C18. The distribution ratios of the C16:0 acids at the Sn-1, sn-2 and Sn-3 positions are also substantially equivalent. Namely, the content of triolein was 47% and the content of tripalmitin was 24%.
The oil was cooled to 0 ℃ for 6h and then filtered to obtain two main types of triglycerides, namely triolein and tripalmitin. The triolein is subjected to subsequent ester exchange reaction to obtain the biodiesel, and the biodiesel with the property can be used as fuel and is an ideal raw material for producing epoxy resin by deep processing.
Comparative experiment 1
The comparative test provides a glycerol esterification method for high acid value oil, which has the same specific steps as those in the example 1, and the difference is that: in this comparative test, 1000kg of high acid value rice bran oil having an acid value of 23.4mgKOH/g and 27kg of glycerin were added to a reactor. Then, a vacuum pump is started to keep the vacuum degree in the reactor at-0.08 MPa, the reaction temperature is 210 ℃, and the reaction time is 4 hours. After the reaction, the acid value was measured and found to be 12.0mgKOH/g.
Comparative experiment 2
The comparative test provides a glycerol esterification method for high acid value grease, which has the same specific steps as those in the example 1, and the difference is that: in the comparative test, 1000kg of high acid value rice bran oil is added into a reactor, the acid value is 23.4mgKOH/g, and the addition amount of glycerol is 27kg; the monoglyceride was glycerol monooleate, and the amount of glycerol monooleate added was 27kg. Then, a vacuum pump is started to keep the vacuum degree in the reactor at-0.08 MPa, the reaction temperature is 210 ℃, and the reaction time is 4 hours. After the reaction, the acid value was measured and found to be 11.1mgKOH/g.
Comparative experiment three
The comparative test provides a glycerol esterification method for high acid value grease, which has the same specific steps as those in the example 1, and the difference is that: in this comparative test, 1000kg of high acid value rice bran oil having an acid value of 23.4mgKOH/g and 27kg of glycerin were added to a reactor. Then, a vacuum pump is started to keep the vacuum degree in the reactor at-0.08 MPa, the reaction temperature is 210 ℃, and the reaction time is 4 hours. After the reaction, the acid value was measured and found to be 10.5mgKOH/g.
Comparative experiment No. four
The comparative test provides a glycerol esterification method for high acid value oil, which has the same specific steps as those in the example 3, and the difference is that: 1000kg of high acid value kitchen waste oil is added into a reactor in the comparative test, the acid value is 80mgKOH/g, and the addition amount of glycerol is 300kg. And starting a vacuum pump to keep the vacuum degree in the reactor at-0.09 MPa, the reaction temperature at 210 ℃ and the reaction time at 6h. After the reaction, the acid value was measured and found to be 8.9mgKOH/g.
Comparative experiment five
This comparative experiment provides a method for glycerol esterification of high acid value oils, the specific steps are substantially the same as those in example 3, except that: in the comparative test, 1000kg of high-acid-value kitchen waste oil with the acid value of 80mgKOH/g, 400kg of glycerol is added into a reactor, monoglyceride is glycerol mono-arachidic acid ester, and the addition of the glycerol mono-arachidic acid ester is 800kg. And starting a vacuum pump to keep the vacuum degree in the reactor at-0.09 MPa, the reaction temperature at 200 ℃ and the reaction time at 6h. After the reaction, the acid value was measured and found to be 9.2mgKOH/g.
Comparative experiment six
This comparative experiment provides a method for glycerol esterification of high acid value oils, the specific steps are substantially the same as those in example 3, except that: in the comparative test, 1000kg of high-acid-value kitchen waste oil with the acid value of 80mgKOH/g and the addition amount of 500kg of glycerol is added into a reactor, and a targeting inducer is PbO + PbCl 2 +MnO 2 +Al 2 O 3 The addition amount of the targeting inducer is 1kg. And starting a vacuum pump to keep the vacuum degree in the reactor at-0.09 MPa, the reaction temperature at 200 ℃ and the reaction time at 6h. After the reaction, the acid value was measured and found to be 8.9mgKOH/g.
Respectively measuring the fatty acid position distribution of the high-acid-value rice bran oil esterified by the high-acid-value oil glyceride esterification method provided by the comparison tests I to III and the fatty acid position distribution of the high-acid-value kitchen waste oil esterified by the high-acid-value oil glyceride esterification method provided by the comparison tests IV to VI by adopting ultra-high performance liquid chromatography (UPLC), wherein the results show that the distribution proportions of C18:1 acid in the comparison tests I to VI in Sn-1 position, sn-2 position and Sn-3 position are different; the distribution ratios of the C16:0 acids at the Sn-1, sn-2 and Sn-3 positions are also different. Therefore, the glycerol esterification method of the high-acid-value grease provided by the invention can effectively reduce the acid value of the high-acid-value grease and better play a role in directionally changing the contents of unsaturated fatty acid and saturated fatty acid distributed on the Sn-2 position and the Sn-1,3 position only by simultaneously adding the three materials into the high-acid-value grease by utilizing the synergistic effect of glycerol, monoglyceride and a targeted inducer.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention and not to limit it; although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art will understand that: modifications to the specific embodiments of the invention or equivalent substitutions for parts of the technical features may be made; without departing from the spirit of the invention, it is intended to cover all modifications within the scope of the invention as claimed.
Claims (2)
1. A glycerol esterification method for high-acid-value oil comprises the following specific steps:
mixing glycerol, monoglyceride, a targeting inducer and high-acid-value grease under a vacuum condition, heating and carrying out esterification reaction to obtain esterified grease, wherein the esterified grease is used as a raw material for producing biodiesel;
wherein the mass of the targeted inducer accounts for 0.1-5% of the mass of the high acid value grease; the mass of the glycerol accounts for 1-50% of the mass of the high acid value oil, the mass of the monoglyceride is 1-10 times of the mass of the glycerol, and the high acid value oil is oil with an acid value of more than 10 mgKOH/g;
the target inducer is PbO + PbCl 2 +MnO 2 +Al 2 O 3 、NiCl 2 •6H 2 O+NaOH+MgCl 2 •6H 2 O；
The monoglyceride is one or more of glycerol monolaurate, glycerol monopalmitate, glycerol monostearate, glycerol monooleate, glycerol monolinoleate, glycerol monolinolenate and glycerol mono-arachidate.
2. The method for glycerol esterification of high acid value oils and fats according to claim 1, wherein: and (2) mixing, heating and esterifying the glycerol, the monoglyceride, the targeting inducer and the high acid value grease under the vacuum condition at the temperature of 100-300 ℃.
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| CN1358709A (en) * | 2000-12-15 | 2002-07-17 | 住友化学工业株式会社 | Method for preparing fatty acid ester |
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| CN1358709A (en) * | 2000-12-15 | 2002-07-17 | 住友化学工业株式会社 | Method for preparing fatty acid ester |
Non-Patent Citations (3)
| Title |
|---|
| Modification of Vegetable Oils. IV. Reesterification of Fatty Acids with Glycerol;R. O. FEUGE et al;《OIL & SOAP》;19451231;第202-207页 * |
| 米糠油化学酯化脱酸的研究;马传国 等;《中国油脂》;20081231;第33卷(第12期);第36-39页 * |
| 马传国 等.米糠油化学酯化脱酸的研究.《中国油脂》.2008,第33卷(第12期),第36-39页. * |
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