CN114181778A - Preparation method of ruminant trans-fatty acid - Google Patents
Preparation method of ruminant trans-fatty acid Download PDFInfo
- Publication number
- CN114181778A CN114181778A CN202111372593.0A CN202111372593A CN114181778A CN 114181778 A CN114181778 A CN 114181778A CN 202111372593 A CN202111372593 A CN 202111372593A CN 114181778 A CN114181778 A CN 114181778A
- Authority
- CN
- China
- Prior art keywords
- fatty acid
- butter
- trans
- free fatty
- urea
- 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.)
- Pending
Links
Images
Classifications
-
- 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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- 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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Feed For Specific Animals (AREA)
- Fodder In General (AREA)
Abstract
The invention discloses a preparation method of trans-fatty acid of ruminant, which comprises the following steps: (1) performing saponification reaction on butter and sodium hydroxide ethanol solution in 85-90 deg.C water bath, adding sulfuric acid solution, stirring at 45-50 deg.C water bath for 20-30min, dissolving, standing, and collecting upper layer oily substance to obtain butter free fatty acid; (2) adding urea into anhydrous ethanol according to a certain proportion, performing rotary reflux at 70-85 deg.C, adding certain butter free fatty acid, refluxing at 77 deg.C, and standing at-5 deg.C for inclusion; vacuum filtering to obtain filtrate, rotary evaporating the filtrate at 65 deg.C to remove ethanol, dissolving with 60 deg.C deionized water, extracting upper layer oily substance, drying with anhydrous sodium sulfate, and filtering to obtain ruminant trans-fatty acid product. The preparation method of the trans-fatty acid of the ruminant, which is disclosed by the invention, has the advantages of simple process, strong operability, low production cost and low energy consumption, and is easy to realize large-scale continuous production.
Description
Technical Field
The invention belongs to the technical field of trans-fatty acid preparation, and particularly relates to a preparation method of trans-fatty acid of ruminants.
Background
Currently, there are two main methods for preparing high-content ruminant trans-fatty acid products: firstly, the feeding of the ruminants is changed, the trans-fatty acid composition of animal meat products and dairy products is different due to different stocking seasons and different feed fatty acid compositions, and the varieties of trans-fatty acid isomers of the ruminants are rich, and the dairy products and the trans-fatty acids of the ruminants are 57% higher than those of the ruminants mainly fed with the feeds in winter when the ruminants mainly feed the grass in summer; when 5.2% sunflower oil (containing 69% linoleic acid) is added into the feed, the content of trans-fatty acid in ruminant animals can also be increased. Therefore, the feed is changed to feed the dairy cows, and the butter product with higher trans-fatty acid content of the ruminants can be obtained, and the disadvantages of time and labor consumption, need of sites and the dairy cows and high cost investment are overcome; secondly, chemical synthesis of ruminant trans-fatty acids, in which 11t 18: 1 accounts for 60% of total ruminant trans-fatty acids, is often used to represent ruminant trans-fatty acids at 11t 18: 1 and I-TFA at 9t 18: 1 in experiments. Swain found that the chemical base isomerization of vegetable oil rich in linoleic acid synthesized 11t 18: 1 with higher purity. The method has certain dangerousness due to high temperature and pressure in the reaction process and long-time high temperature and pressure maintenance, and in addition, the trans-fatty acid of the ruminant is a mixture of trans-monounsaturated fatty acid, although the 11t 18: 1 is the fatty acid which is representative of the trans-fatty acid of the ruminant, the whole appearance of the trans-fatty acid of the ruminant cannot be reflected.
Studies report that urea encapsulation removes saturated fatty acids from butter, thereby enriching more monounsaturated fatty acids. Therefore, the invention adopts a urea inclusion method, takes the content of the trans-monounsaturated fatty acid as an index, researches the influence of main conditions such as the ratio of free fatty acid to urea, the ratio of the free fatty acid to ethanol, the inclusion time and the like in the urea inclusion process on the content of the trans-monounsaturated fatty acid in the product, and researches the influence of the three factors on the preparation of the trans-fatty acid of the ruminant by adopting a response surface method, thereby researching the optimal preparation process parameters of the trans-fatty acid of the ruminant.
Disclosure of Invention
Aiming at the defects and problems in the prior art, the invention aims to provide a preparation method of trans-fatty acid of ruminant.
The invention is realized by the following technical scheme:
a preparation method of ruminant trans-fatty acid comprises taking butter as raw material, and obtaining butter free fatty acid by saponification and acid hydrolysis; the free fatty acid of the butter and the urea are subjected to inclusion reaction by a urea inclusion method, saturated fatty acid in the free fatty acid of the butter is removed, and the content of trans-fatty acid of the ruminant is increased.
The preparation method comprises the following specific steps:
(1) preparation of butter free fatty acids
Performing saponification reaction on butter and 1mol/L sodium hydroxide ethanol solution in a water bath at 85-90 ℃;
then sequentially cooling and vacuum filtering to obtain saponified substance;
adding 0.5mol/L sulfuric acid solution into saponified substance, stirring at 45-50 deg.C water bath for 20-30min to completely dissolve the saponified substance, standing, collecting upper layer oily substance, and washing with hot purified water to neutral to obtain butter free fatty acid;
(2) removal of saturated fatty acids by urea encapsulation
Adding urea into absolute ethyl alcohol according to a certain proportion, and carrying out rotary reflux at the temperature of 70-85 ℃ to completely dissolve the urea;
adding certain butter free fatty acid, refluxing at 77 deg.C, and clathrating at-5 deg.C;
and after the inclusion is finished, carrying out vacuum filtration to obtain a filtrate, carrying out rotary evaporation on the filtrate at 65 ℃, removing ethanol, dissolving the filtrate by using deionized water at 60 ℃, extracting an upper-layer oily substance, drying by using anhydrous sodium sulfate, and filtering to obtain the ruminant trans-fatty acid product.
Preferably, the mass ratio (g/g) of the free fatty acid of the yellow oil to the urea in the step (2) is 1: 1.5-1.2.5; the mass ratio (g/mL) of butter free fatty acid to ethanol is 1: 2-1: 4.
Compared with the prior art, the preparation method of the trans-fatty acid of the ruminant has the advantages of simple process, strong operability, low production cost and low energy consumption, and is easy to realize large-scale continuous production.
Drawings
FIG. 1 is a curved view of interaction response of three factors in trans-fatty acid of ruminant, wherein (A) is the ratio of free fatty acid to urea and the ratio of free fatty acid to ethanol; (B) the ratio of butter free fatty acid to urea and the inclusion time; (C) the ratio of butter free fatty acid to ethanol and the inclusion time.
Detailed Description
The invention will be further described with reference to the accompanying drawings.
Example 1 preparation of ruminant trans fatty acids
(1) Preparation of butter free fatty acid. Putting a certain amount of butter into a beaker in a constant-temperature water bath kettle at 90 ℃, adding the butter into 1mol/L NaOH ethanol solution when the butter is completely melted into liquid, magnetically stirring the mixture for 2 hours at a material-liquid ratio of 1: 6, carrying out saponification reaction, taking out the beaker, cooling the beaker to room temperature, carrying out vacuum filtration to obtain a saponified substance, adding 0.5mol/L sulfuric acid solution into the saponified substance, stirring the saponified substance in the water bath kettle at 50 ℃ to dissolve the substance, standing and layering the substance, dividing the substance into three layers to ensure that the pH value of the upper-layer oily substance is about 2-3, taking the upper-layer oily substance, and washing the upper-layer oily substance with hot purified water to be neutral to obtain the butter free fatty acid.
(2) The urea inclusion method removes saturated fatty acids. Adding urea into absolute ethyl alcohol according to a certain proportion, and carrying out rotary reflux at the temperature of 85 ℃ to completely dissolve the urea; adding certain butter free fatty acid, refluxing at 77 deg.C, and clathrating at-5 deg.C; and after the inclusion is finished, carrying out vacuum filtration to obtain filtrate, carrying out rotary evaporation on the filtrate at 65 ℃, removing ethanol, dissolving the filtrate by using deionized water at 60 ℃, extracting an upper-layer oily substance, drying by using anhydrous sodium sulfate, and filtering to obtain the concentrate containing the ruminant trans-fatty acid.
Example 2 Single factor test of Urea to butter free fatty acid ratio
Weighing 10g of butter free fatty acid obtained in the step (1), carrying out the step (2) according to the conditions that the ratio of urea to ethanol is 1: 3, the inclusion time is 12h, and the ratio of the butter free fatty acid to urea is 1: 1, 1: 1.5, 1: 2, 1: 2.5 and 1: 3, and examining the influence of the ratio of the butter free fatty acid to urea on the trans-fatty acid content of ruminants in the product, wherein the results are shown in Table 1.
TABLE 1 Effect of butter free fatty acid to Urea ratio on the Trans-monounsaturated fatty acid content of the product (% by area)
Note: fatty acid refers to the fatty acid composition and content of the product prepared, wherein SFA: a saturated fatty acid; MUFA: monounsaturated fatty acids; PUFA: a polyunsaturated fatty acid; C-MUFA: cis-monounsaturated fatty acids; T-MUFA: trans-monounsaturated fatty acids; CLA: conjugated linoleic acid.
Example 3 Single factor test of ethanol to butter free fatty acid ratio
The influence of the ratio of butter free fatty acid to ethanol on the trans-fatty acid content of ruminants in the product was examined for 12h under the conditions that the ratio of butter free fatty acid to urea was 1: 1 and the ratio of urea to ethanol was 1: 1, 1: 2, 1: 3, 1: 4, 1: 5, and the results are shown in Table 2.
TABLE 2 Effect of butter free fatty acid to ethanol ratio on Trans-monounsaturated fatty acid content in the product (% by area)
Note: fatty acid refers to the fatty acid composition and content of the product prepared, wherein SFA: saturated fatty acids MUFA: monounsaturated fatty acid PUFA: polyunsaturated fatty acid C-MUFA: cis-monounsaturated fatty acid T-MUFA: trans-monounsaturated fatty acid CLA: conjugated linoleic acid
Example 4 Single factor test for Inclusion time
The influence of the extraction time on the trans-fatty acid content of ruminants in the product is examined by taking the ratio of free fatty acid to urea of butter as 1: 2, the ratio of urea to ethanol as 1: 3 and the inclusion time as 8, 10, 12, 14 and 16h, and the results are shown in Table 3.
TABLE 3 Effect of inclusion time on the content of trans-monounsaturated fatty acids in butter oil (% by area)
Note: fatty acid refers to the fatty acid composition and content of the product prepared, wherein SFA: saturated fatty acids MUFA: monounsaturated fatty acid PUFA: polyunsaturated fatty acid C-MUFA: cis-monounsaturated fatty acid T-MUFA: trans-monounsaturated fatty acid CLA: conjugated linoleic acid
Example 5 response surface optimization test
On the basis of the single-factor test result, three factors are selected by combining the design principle of the Box-Behnken center combined test as shown in Table 4: the ratio of butter free fatty acid to urea (a), the ratio of urea to ethanol (B), and the inclusion time (C) were used as independent variables, and the ruminant trans-fatty acid content in the product was used as a response value, and all experimental data were analyzed using software Design-expert V8.06, and the results are shown in table 5 and fig. 1.
TABLE 4 Box-Behnken design factors and horizon table
TABLE 5 response surface test design and results
The samples prepared in the examples were subjected to acid methyl esterification and gas chromatography analysis as follows:
weighing 2mg of sample in a 15mL test tube by adopting an acid methyl esterification method, respectively adding 2mL of 14% boron trifluoride-methanol solution and 1mL of toluene, flushing nitrogen, sealing, heating in a 90 ℃ water bath for 60min, cooling to room temperature, adding 3mL of n-hexane and 1mL of ultrapure water, uniformly mixing, centrifuging at 2000rpm/min for 10min, taking 2mL of supernatant, drying by using nitrogen, adding 1mL of chromatographically pure hexane for redissolving, transferring to a sample bottle, and measuring by GC.
Gas chromatography, chromatographic conditions: the column was a CP-Sil88 fused silica capillary column (100 m.times.0.25 mm. times.0.2 μm). The carrier gas and fuel gas were N2 and H2, respectively. The FID temperature and the injection port temperature were both 250 ℃. Temperature programming for 86 min: maintaining at 45 deg.C for 4min, heating to 175 deg.C at 13 deg.C/min, maintaining for 27min, heating to 215 deg.C at 4 deg.C/min, and maintaining for 35 min. Fatty acid analysis was referenced to the fatty acid 463 standard map.
As a result: the relation between the main conditions such as the ratio of free fatty acid to urea, the ratio of free fatty acid to ethanol, the inclusion time and the like and the purity of the trans-monounsaturated fatty acid in the urea inclusion process is researched. The influence of the three factors on the preparation of the trans-monounsaturated fatty acid is researched by adopting a response surface method, and the optimal conditions for preparing the trans-monounsaturated fatty acid product are obtained, namely the ratio of butter free fatty acid to urea is 1: 2, the inclusion time of the butter free fatty acid to ethanol is 1: 2 is 20 hours, and the content of the extractable trans-monounsaturated fatty acid product is about 12.28 percent.
The foregoing merely represents preferred embodiments of the invention, which are described in some detail and detail, and therefore should not be construed as limiting the scope of the invention. It should be noted that, for those skilled in the art, various changes, modifications and substitutions can be made without departing from the spirit of the present invention, and these are all within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (3)
1. A preparation method of trans-fatty acid of ruminant is characterized in that: the preparation method takes butter as a raw material, and obtains butter free fatty acid through saponification and acid hydrolysis; the free fatty acid of the butter and the urea are subjected to inclusion reaction by a urea inclusion method, saturated fatty acid in the free fatty acid of the butter is removed, and the content of trans-fatty acid of the ruminant is increased.
2. The method for preparing trans fatty acids of ruminants according to claim 1, wherein the method comprises the following specific steps:
(1) preparation of butter free fatty acids
Performing saponification reaction on butter and 1mol/L sodium hydroxide ethanol solution in a water bath at 85-90 ℃;
then sequentially cooling and vacuum filtering to obtain saponified substance;
adding 0.5mol/L sulfuric acid solution into saponified substance, stirring at 45-50 deg.C water bath for 20-30min to completely dissolve the saponified substance, standing, collecting upper layer oily substance, and washing with hot purified water to neutral to obtain butter free fatty acid;
(2) removal of saturated fatty acids by urea encapsulation
Adding urea into absolute ethyl alcohol according to a certain proportion, and carrying out rotary reflux at the temperature of 70-85 ℃ to completely dissolve the urea;
adding certain butter free fatty acid, refluxing at 77 deg.C, and clathrating at-5 deg.C;
and after the inclusion is finished, carrying out vacuum filtration to obtain a filtrate, carrying out rotary evaporation on the filtrate at 65 ℃, removing ethanol, dissolving the filtrate by using deionized water at 60 ℃, extracting an upper-layer oily substance, drying by using anhydrous sodium sulfate, and filtering to obtain the ruminant trans-fatty acid product.
3. The method of claim 1, wherein the method comprises the steps of: the mass ratio (g/g) of the free fatty acid of the yellow oil to the urea in the step (2) is 1: 1.5-1.2.5; the mass ratio (g/mL) of butter free fatty acid to ethanol is 1: 2-1: 4, and the inclusion time is 12-20 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111372593.0A CN114181778A (en) | 2021-11-18 | 2021-11-18 | Preparation method of ruminant trans-fatty acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111372593.0A CN114181778A (en) | 2021-11-18 | 2021-11-18 | Preparation method of ruminant trans-fatty acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114181778A true CN114181778A (en) | 2022-03-15 |
Family
ID=80602181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111372593.0A Pending CN114181778A (en) | 2021-11-18 | 2021-11-18 | Preparation method of ruminant trans-fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114181778A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113736568A (en) * | 2021-08-25 | 2021-12-03 | 安徽天凯生物科技有限公司 | Preparation process of water-soluble fatty acid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN107312805A (en) * | 2017-08-07 | 2017-11-03 | 中国农业大学 | A kind of preparation and its application of the polyunsaturated fatty acid rich in CLA |
| CN108822959A (en) * | 2018-06-28 | 2018-11-16 | 中国科学院新疆理化技术研究所 | A kind of enrichment method and purposes of marrow oil unsaturated fatty acid |
-
2021
- 2021-11-18 CN CN202111372593.0A patent/CN114181778A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN107312805A (en) * | 2017-08-07 | 2017-11-03 | 中国农业大学 | A kind of preparation and its application of the polyunsaturated fatty acid rich in CLA |
| CN108822959A (en) * | 2018-06-28 | 2018-11-16 | 中国科学院新疆理化技术研究所 | A kind of enrichment method and purposes of marrow oil unsaturated fatty acid |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113736568A (en) * | 2021-08-25 | 2021-12-03 | 安徽天凯生物科技有限公司 | Preparation process of water-soluble fatty acid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104529772B (en) | A kind of simulated moving bed chromatography prepares high-purity EPA ester and the method for DHA ester monomer | |
| CN104651422B (en) | A kind of method that triglyceride type DHA and EPA are extracted from deep-sea fish | |
| Homayooni et al. | Concentrations of omega-3 fatty acids from rainbow sardine fish oil by various methods. | |
| KR20020042432A (en) | Method for isolating high-purified unsaturated fatty acids using crystallization | |
| CN105219813B (en) | A kind of method that enzyme process prepares bis- oleic acid -2- palmitic acid of 1,3-, three ester in subcritical system | |
| CN102690283B (en) | Method for extracting lecithin from egg yolk | |
| CN105503580B (en) | A kind of extraction separation method of nervonic acid | |
| CN108084020B (en) | Method for preparing omega-7 fatty acid ester by using grease as raw material | |
| CN114181778A (en) | Preparation method of ruminant trans-fatty acid | |
| CN107200767A (en) | A kind of preparation method of blood-sugar decreasing active Corosolic acid | |
| CN112592268A (en) | Method for separating EPA (eicosapentaenoic acid) in fish oil by using continuous chromatographic system | |
| CN102320953B (en) | Method for preparing natural alpha-linolenic acid from crude oil of idesia polycarpa var.vestita diels | |
| CN103467432B (en) | A kind of method extracting vitamin E from deodorizer distillate of idesia polycarpa oil | |
| CN115010596A (en) | Method for enriching eicosapentaenoic acid in fish oil raw material | |
| CN104418726A (en) | Extraction method of [alpha]-linolenic acid | |
| TW201808277A (en) | Method for extracting and purifying conjugated triene linolenic acid comprising extracting, esterfying and purifying | |
| CN101024609B (en) | Process for producing shikimic acid | |
| CN108250066A (en) | A kind of isolation and purification method of high-purity unrighted acid | |
| CN110590545A (en) | Method for completely separating oleic acid and linoleic acid | |
| CN106892791A (en) | Extract method and the medicine containing squalene of plant source spiny dogfish ene compositions and its preparation method and application | |
| CN103351298A (en) | Purification method of 1,3-diglyceride | |
| CN107739296B (en) | Method for collecting oleic acid from tea oil | |
| CN105418575A (en) | Method for extracting natural vitamin E through two-step reextraction method | |
| CN105177073B (en) | A kind of method preparing Phosphatidylserine | |
| CN110642711B (en) | Method for separating alpha-linolenic acid from peony seed oil |
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 |