CN112980591A - Preparation method of low-iodine-value fatty acid product and low-iodine-value fatty acid product - Google Patents
Preparation method of low-iodine-value fatty acid product and low-iodine-value fatty acid product Download PDFInfo
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- B01D3/14—Fractional distillation or use of a fractionation or rectification column
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Abstract
The present application relates to a process for reducing the iodine value of a fatty acid product and a process for the preparation of a fatty acid product comprising at least one distillation step. Feeding a saturated fatty acid mixture into a distillation tower in the distillation step, and generating a fatty acid product, a low-boiling-point component and a tower bottom product after the treatment of the distillation step, wherein the saturated fatty acid mixture contains more than 0-1 wt% of pentadecene, and M is more than or equal to 1.2 and less than or equal to 5.0 in the distillation step, and is defined in the specification. Accordingly, the present application also provides fatty acid products prepared therefrom. The method has simple process, and the iodine value of the obtained fatty acid is less than 0.25gI2/100g。
Description
Technical Field
The present application relates to a process for the preparation of fatty acid products, particularly low iodine value fatty acid products, and a process for reducing the iodine value of fatty acid products. The application also provides a low iodine value fatty acid product prepared by the method.
Background
The iodine value is an index indicating the degree of unsaturation in an organic compound, and is an index indicating the number of grams of iodine that can be absorbed (added) in 100g of a substance, and is mainly used for measurement of substances such as fats and oils, fatty acids, waxes, and polyesters. The greater the degree of unsaturation, the higher the iodine number. The iodine value of the drying oil is greater than that of the non-drying oil.
The level of iodine value depends on the degree of unsaturation of the product, and hydrogenation is generally one of the methods for reducing the iodine value of fats and oils or fatty acids.
Hydrogenation of fats is usually carried out by using a catalyst such as nickel to convert unsaturated double bonds in the fats into saturated bonds through hydrogenation reaction, thereby achieving the purpose of reducing iodine value. The hydrogenation of fatty acids is more complicated than that of fats and oils, and fats and oils are generally selected as raw materials, and first hydrolyzed, and then the hydrolyzed fatty acids are hydrogenated, and for purification, the fatty acids are generally distilled after hydrogenation.
Theoretically, if all unsaturated fatty acids in the fatty acids are hydrogenated to saturated fatty acids (FAC pattern can be analyzed), the end point of the hydrogenation reaction is determined, but the Iodine Value (IV) actually remains even after all the fatty acids are hydrogenated. Saturated fatty acids are generally required in rubber and tires, and generally the higher the degree of saturation the better the product stability and therefore the lower the iodine number required the better.
In order to provide fatty acid products with lower iodine values and more stable properties, it is also desirable to provide a more convenient and efficient method of making or processing fatty acids.
Disclosure of Invention
In a first aspect, the present application provides a process for reducing the iodine value of a fatty acid product, said process comprising at least one distillation step in which a saturated fatty acid mixture fed to the at least one distillation step is subjected to a distillation step to produce a fatty acid product, a low boiling component and a bottoms product, wherein the saturated fatty acid mixture contains greater than 0 to 1 wt% pentadecenes,
wherein the content of pentadecene in the fatty acid product, the low-boiling component, the bottom product of the column is adjusted in the distillation step so that the condition of 1.2. ltoreq. M '5.0, preferably 1.3. ltoreq. M' 3.6 is satisfied, wherein
In a preferred aspect, the content of pentadecene in the fatty acid product, the low-boiling component, the bottom product of the column is adjusted in the distillation step so that the condition 1.8. ltoreq. N '3.0, preferably 2.0. ltoreq. N' 3.0 is simultaneously satisfied,
wherein the content of the first and second substances,
further preferably, the saturated fatty acid mixture comprises palmitic acid and/or stearic acid. For example, the saturated fatty acid mixture comprises greater than 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, or 99% by weight palmitic acid and/or stearic acid. Particularly preferably, the saturated fatty acid mixture comprises more than 95 wt.%, 96 wt.%, 97 wt.%, 98 wt.% or 99 wt.% of palmitic acid and/or stearic acid.
In a second aspect, the present application provides a process for the production of a fatty acid product comprising a first distillation step in which a saturated fatty acid mixture is fed to a first distillation column and treated by the first distillation step to produce a first fatty acid product, a first low boiling component and a first bottoms product, wherein the saturated fatty acid mixture contains greater than 0 to 1 wt% pentadecene,
in the first distillation step, the value of M is adjusted such that 1.2. ltoreq. M.ltoreq.5.0, preferably 1.3. ltoreq. M.ltoreq.3.6, where
In a preferred aspect, the value of N is adjusted in the first distillation step such that 1.8. ltoreq. N.ltoreq.3.0, preferably 2.0. ltoreq. N.ltoreq.3.0, wherein,
in the saturated fatty acid mixture fed to the first distillation column, palmitic acid and/or stearic acid are preferably contained. For example, the saturated fatty acid mixture comprises greater than 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, or 99% by weight palmitic acid and/or stearic acid. Particularly preferably, the saturated fatty acid mixture comprises more than 95 wt.%, 96 wt.%, 97 wt.%, 98 wt.% or 99 wt.% of palmitic acid and/or stearic acid.
Preferably, the process for producing a fatty acid product further comprises a second distillation step in which the first bottoms product is fed to a second distillation column and treated by the second distillation step to produce a second fatty acid product, a second lower boiling component, and a second bottoms product.
Further preferably, the distillation treatment in the second distillation step comprises controlling the second column bottom temperature to 227-.
Further, in some embodiments of the process for producing a fatty acid product according to the present application, the process may further comprise a hydrogenation step prior to the first distillation step. In the hydrogenation step, the mixed fatty acids are hydrogenated to obtain a saturated fatty acid mixture. It is understood that mixed fatty acid means a mixture of one or more saturated fatty acids and/or one or more unsaturated fatty acids. In particular, in the present application, the mixed fatty acids typically comprise at least one unsaturated fatty acid, such as a C18 unsaturated fatty acid.
The mixed fatty acids may be obtained from a hydrolysis step. Thus, in some embodiments of the method of producing a fatty acid product according to the present application, the method may further comprise a hydrolysis step prior to the hydrogenation step. In the hydrolysis step, the raw material oil is hydrolyzed into mixed fatty acids. Specifically, in the hydrolysis step, the raw material oil or fat is hydrolyzed into a mixture of corresponding saturated fatty acids and/or unsaturated fatty acids to obtain mixed fatty acids, and glycerin formed therewith is removed.
As the raw material oil or fat, various oils and fats, for example, naturally occurring oils and fats, can be used. In the present application, the oil is preferably selected from the group consisting of soybean oil, rapeseed oil, peanut oil, cottonseed oil, sunflower oil, sesame oil, camellia oil, rice bran oil, linseed oil, corn oil, safflower oil, palm oil, olive oil, or any mixture thereof. Palm oil is particularly preferred. Further preferably, those fats and oils which are capable of generating C16 saturated or unsaturated fatty acids and/or C18 saturated or unsaturated fatty acids are selected for use in the present application.
In a third aspect of the present application, there is provided a fatty acid product having an Iodine Value (IV) of less than 0.25gI, obtained from a process for reducing the iodine value of a fatty acid product2/100g。
In a fourth aspect of the present application, there is provided a first fatty acid product having an Iodine Value (IV) of less than 0.25gI prepared by the foregoing process2/100g。
In a fifth aspect of the present application, there is provided a second fatty acid product having an Iodine Value (IV) of less than 0.25 gl produced by the foregoing process2/100g。
Drawings
In the drawings, there is shown in the drawings,
fig. 1 shows a distillation process comprising one distillation column (corresponding to one distillation step).
Figure 2 shows a distillation process comprising two distillation columns (corresponding to two distillation steps).
Detailed Description
The following describes in detail specific embodiments of the present application. In the method for preparing a fatty acid product or the method for reducing the iodine value in a fatty acid product according to the present application, the distillation step in the conventional preparation process is mainly improved. In particular, the applicant of the present application has unexpectedly found that during the preparation of fatty acid products, some low-melting point components, such as pentadecene, are generally formed along with the hydrolysis or subsequent hydrogenation of various fats and oils, and that by adjusting the content or ratio of the contents of pentadecene in each distillation product, the iodine value in the final fatty acid product obtained can be effectively reduced, thereby also effectively improving the stability of the fatty acid product. Further, the applicant has also found that even if two or more distillation steps are involved, two or more fatty acid products having different compositions but low iodine values can be obtained via the two or more distillation steps by only adjusting the content and/or content ratio of pentadecene in each fatty acid product in the first distillation step.
The present application provides, first in some embodiments, a process for reducing the iodine value of a fatty acid product comprising at least one distillation step in which a saturated fatty acid mixture fed is subjected to a distillation step to produce a fatty acid product, a low boiling component, and a bottoms product. It should be understood that "lower boiling component" refers herein to a mixture of volatile species that distills from the top of the distillation column in a distillation process. In particular, pentadecene is contained in the saturated fatty acid mixture, and thus pentadecene is also contained in the "low-melting-point component". It is also conceivable to additionally introduce into the saturated fatty acid mixture, before or simultaneously with the distillation, an appropriate amount of pentadecene. Advantageously, the content of pentadecene in the saturated fatty acid mixture is from more than 0 to 1% by weight, for example from more than 0 to 0.5% by weight. Thus, in the method according to the present invention, the iodine value in the fatty acid end product is effectively reduced by adjusting the content of pentadecene in the fatty acid product, the low-boiling component, and the bottom product to satisfy suitable conditions.
In some embodiments for reducing the iodine value of the fatty acid product, the amount of pentadecene in the fatty acid product, the low boiling point component, the bottoms product is adjusted such that the condition 1.2. ltoreq. M '5.0, preferably 1.3. ltoreq. M' 3.6 is met, wherein
Further, in the method for reducing the iodine value of a fatty acid product, it is preferable to reduce the iodine value of a fatty acid product by adjusting the content of pentadecene in the fatty acid product, the low-boiling component, the bottom product while satisfying the condition of 1.8. ltoreq. N '.ltoreq.3.0, preferably 2.0. ltoreq. N'.ltoreq.3.0,
wherein the content of the first and second substances,
it should be understood that the method of reducing the iodine value of a fatty acid (product) according to the present application may be implemented alone to treat the fatty acid or may be integrated into any other fatty acid related process.
In the present application, the iodine value of the fatty acid may be measured using a conventional apparatus or in a conventional manner in the art.
In the present application, the pentadecene content can be measured using the conventional measurement method of fatty acid composition in the art "determination of fatty acid in food of national standard for food safety" GB 5009.168-2016.
The present application also provides a process for the production of a fatty acid product comprising at least a first distillation step in which a saturated fatty acid mixture is fed to a first distillation column and processed by the first distillation step to produce a first fatty acid product, a first low-melting component and a first bottoms product. For example, fig. 1 shows a distillation process comprising one distillation column (corresponding to one distillation step). Pentadecene is contained in the saturated fatty acid mixture for process reasons, and can also be additionally introduced. Advantageously, the saturated fatty acid mixture contains more than 0 to 1% by weight of pentadecene.
In a preferred embodiment, the value of M is adjusted in the first distillation step of the process for the production of fatty acid products according to the present application such that 1.2. ltoreq. M.ltoreq.5.0, preferably 1.3. ltoreq. M.ltoreq.3.6, where M has the following meaning:
preferably, the saturated fatty acid mixture comprises palmitic acid (i.e. palmitic acid or palmitic acid) and/or stearic acid (i.e. stearic acid). It will be appreciated that other saturated fatty acids with different carbon chain lengths may also be included in the saturated fatty acid mixture, such as myristic acid (i.e. myristic acid), lauric acid (i.e. lauric acid).
C16 and C18 fatty acids are important fatty acids in the field of oil and fat chemical industry, and one of the sources thereof is refined palm Stearin (ST). Palm stearin is a solid ester of palm oil isolated under refrigeration conditions and is less costly to hydrogenate because of its higher saturated fat content. From the viewpoint of chemical equilibrium, increasing the amount of hydrogen and the amount of catalyst used in the hydrogenation process contributes to the reduction of the iodine value.
It is therefore advantageous if the content of hexadecanoic and/or octadecanoic acid in the saturated fatty acid mixture fed to the first distillation column is greater than 50%, 60%, 70%, 80%, 90% or 95% by weight. Most advantageously, the total content of palmitic and/or stearic acid in the saturated fatty acid mixture is at least 95 wt.%, for example at least 96 wt.%, 97 wt.%, 98 wt.% or 99 wt.%.
The applicants of the present application have surprisingly found that when the distillation step is adjusted to control the value of M at 1.2. ltoreq. M.ltoreq.5.0, in particular at 1.3. ltoreq. M.ltoreq.3.6, the iodine value, i.e.the degree of unsaturation, in the fatty acid product can be effectively controlled.
In a further preferred embodiment, the value of N is adjusted such that 1.8. ltoreq. N.ltoreq.3.0, preferably 2.0. ltoreq. N.ltoreq.3.0,
wherein, the meaning of N is as follows,
the inventors have found that when the numerical ranges of the M value and the N value are satisfied at the same time, the iodine value of the obtained fatty acid product can be further effectively controlled to be less than 0.25gI2/100g。
In some particular embodiments, the process of the present application may comprise only one distillation step. In this case, the process may comprise only one distillation column, obtaining a fatty acid product whose Iodine Value (IV) may advantageously be less than 0.25gI2/100g。
As mentioned before, the process for the production of fatty acids according to the present application must comprise at least one distillation step, i.e. comprising at least one distillation column. When the production method includes two or more distillation steps, for the convenience of description, they are referred to as a first distillation step, a second distillation step, and the like, respectively, corresponding to a first distillation column and a second distillation column, respectively. It is understood that three distillation columns or more may be further included according to the production method of the present invention.
Preferably, the process for the preparation of a fatty acid product according to the present application may further comprise a second distillation step. In the second distillation step, the first bottoms product is fed to a second distillation column and subjected to distillation to produce a second fatty acid product, a second lower boiling component, and a second bottoms product. For example, fig. 2 shows a distillation process comprising two distillation columns (corresponding to two distillation steps). In the second distillation step, the distillation treatment comprises controlling the second column bottom temperature to 227-.
The inventors have found that the Iodine Value (IV) of the second fatty acid product obtained from the second distillation step or second distillation column may also advantageously be less than 0.25gI2/100g。
The composition of the second fatty acid product can be the same as, but is generally different from, the first fatty acid product. That is, the preparation process according to the present application, when comprising at least two, e.g. two, distillation steps, can obtain compositions that differ but that have iodine values that are both below 0.25gI2100g of two fatty acid products. This is quite convenient in industry, and different products can meet different application requirements.
In some embodiments, the preparation method according to the present application may start with a hydrolysis step. I.e. starting from the hydrolysis of fats & oils into fatty acid mixtures and glycerol. In principle, the method of the present application is applicable to various greases. Preferably, the present application is applicable to oils and fats selected from soybean oil, rapeseed oil, peanut oil, cottonseed oil, sunflower seed oil, sesame oil, camellia seed oil, rice bran oil, linseed oil, corn oil, safflower seed oil, palm oil, olive oil and the like. Preferred for use herein are fats and oils that produce C16 saturated and/or unsaturated fatty acids and/or C18 saturated and/or unsaturated fatty acids. In a preferred embodiment, palm oil is most preferred. In the hydrolysis step, the glycerol formed is also removed, giving a mixture of various fatty acids. The hydrolysis process of the fatty acid may be performed using a conventional process method or a conventional operation in the related art. It is understood that the mixed fatty acid obtained by hydrolysis may contain saturated or unsaturated fatty acids having other carbon numbers, such as C14 saturated/unsaturated fatty acid, C12 saturated/unsaturated fatty acid, C10 saturated/unsaturated fatty acid and C8 saturated/unsaturated fatty acid, in addition to C16 saturated/unsaturated fatty acid and C18 saturated/unsaturated fatty acid (including C18:1 fatty acid, C18:2 fatty acid, C18:3 fatty acid).
The hydrolysis process of the fats & oils is conventional in the art or may be carried out using a hydrolysis apparatus conventional in the art.
After hydrolysis, the resulting mixture containing saturated/unsaturated fatty acids is subjected to hydrogenation to convert the unsaturated fatty acids therein to saturated fatty acids. The hydrogenation step of the unsaturated fatty acid may be carried out using a conventional process or a conventional operation in the related art. A hydrogenation catalyst commonly used in hydrogenation processes is nickel (Ni). After the hydrogenation step a mixture of substantially saturated fatty acids is obtained. Preferably, the proportion of saturated fatty acids is up to 99% or more. In the mixture of saturated fatty acids, volatile components such as pentadecene are present in small amounts.
The hydrogenation process of (unsaturated) fatty acids is conventional in the art or may be carried out using hydrogenation equipment conventional in the art.
As mentioned before, the key point of the present application is to control the parameters related to the pentadecene content, including the value of M and the value of N, for example by adjusting the vacuum, the amount of steam, the temperature (profile) and the flow in the first distillation column, where M and N are:
in an advantageous embodiment, the iodine value of the fatty acid product produced can be effectively reduced when the content of pentadecene in each product is adjusted such that 1.2. ltoreq. M.ltoreq.5.0 and 1.8. ltoreq. N.ltoreq.3.0. In a particularly advantageous embodiment, when the content of pentadecene in each product is adjusted such that 1.3. ltoreq. M.ltoreq.3.6 and 2.0. ltoreq. N.ltoreq.3.0, the iodine value of the fatty acid product produced can be further effectively reduced, and even the iodine value in the fatty acid product obtained from the distillation column can be effectively controlled to be less than 0.25gI2100g of the total weight. Advantageously, depending on the process design, multiple (e.g., two) iodine values each below 0.25gI can be achieved simultaneously2100g of fatty acid product but with different composition.
It should be understood that features, characteristics, components or steps described in a particular aspect, embodiment or example of the present application may be applied to any other aspect, embodiment or example described herein unless incompatible therewith.
The above disclosure generally describes the present application, which is further exemplified by the following examples. These examples are described merely to illustrate the present application and do not limit the scope of the present application. Although specific terms and values are employed herein, they are to be understood as exemplary and not limiting the scope of the application. Unless otherwise indicated, the experimental methods and techniques described herein are those conventional in the art.
Examples
In this example, refined palm Stearin (ST) was used as the starting material. ST is common oil from C16 and C18, and the basic physicochemical indexes of ST raw materials from three different batches are shown in the following Table 1, wherein the Iodine Value (IV) is a value for measuring the degree of unsaturation, the Saponification Value (SV) is mainly used for measuring the oil component, AV is the acid value, and PV is the peroxide value. The fatty acid composition of the three batches of the ST oil and fat are shown in table 2 below.
1. Analysis of starting materials
Table 1: basic physicochemical indexes of ST
Table 2: fatty Acid Composition (FAC) in raw oil and fat (wt%)
| C14 | C16 | C17 | C18:0 | C18:1 | C18:2 | C18:3 | |
| Starting materials 1 | 1.17 | 59.51 | 0.13 | 6.4 | 26.2 | 5.88 | 0.46 |
| Raw material 2 | 1.16 | 58.12 | 0.34 | 5.9 | 26.5 | 6.51 | 0.94 |
| Raw material 3 | 1.15 | 57.89 | 0.11 | 5.4 | 27.1 | 6.58 | 1.44 |
The ST oil and fat raw materials 1 to 3 were subjected to hydrolysis and hydrogenation treatment as follows.
2. Hydrolysis of fats and oils
The grease raw materials 1-3 enter the bottom of the hydrolysis tower after being preheated respectively, purified water (containing condensed water) is added from the top of the tower, 60bar steam (the temperature is about 270 ℃) is sprayed into an oil/water mixture to hydrolyze the oil under high temperature and high pressure, the oil is hydrolyzed in the process of continuously floating up because the density of the oil is less than that of the water, and the hydrolysis degree can be more than 99% without using a catalyst under the process condition. The fatty acid is separated from the upper end.
3. Hydrogenation of fatty acids
The grease raw materials 1-3 are hydrolyzed to obtain corresponding fatty acid mixtures respectively, and the compositions of the fatty acid mixtures are the same as the above table 2. The fatty acid mixture is preheated and heated, dried to remove water, pumped into a reaction tank, simultaneously added with catalyst Ni (0.15%) and hydrogen, and reacted at the temperature of 190-210 ℃ and the pressure of 25 bar. The fatty acids after completion of the reaction were taken out of the reaction tank and then introduced into a filtration unit, and then the catalyst was removed, thereby obtaining a hydrogenated fatty acid mixture (the respective compositions are shown in table 3).
Table 3: composition of hydrogenated fatty acid mixture,% by weight
From the point of view of fatty acid saturation, the unsaturated fatty acids have been substantially fully hydrogenated. The basic physicochemical indices of the fatty acid mixture before and after hydrogenation were examined and are shown in tables 4 and 5, respectively. In addition, in addition to pentadecene, volatile components such as heptadecene and pentenal were detected in the volatile components of fatty acids. The weight percent pentadecene content in the mixed fatty acids before and after hydrogenation was also determined in tables 4 and 5. The fatty acid composition in the mixture was measured by the method described in GB 5009.168-2016 national food safety Standard for determination of fatty acids in foods.
Table 4: basic physicochemical index of fatty acid mixture of different sources before hydrogenation
Table 5: basic physicochemical indexes of fatty acid mixture of different sources after hydrogenation
4. Distillation of hydrogenated fatty acid mixtures
The distillation process used in the examples is schematically illustrated in fig. 2, and the hydrogenated fatty acid mixture is subjected to further distillation treatment.
The hydrogenated fatty acid was fed to the distillation column, and the values of M and N in the distillation column were controlled by adjusting the degree of vacuum in the distillation column (adjustment range 9-30mbar), the temperature (adjustment range 227 ℃ -235 ℃), the amount of steam (adjustment range 6800-.
Table 6: m and N values obtained by adjustment in examples 1 to 6
| Examples | Source of feed | M | N |
| 1 | Starting materials 1 | 3.6 | 3.0 |
| 2 | Starting materials 1 | 2.8 | 2.8 |
| 3 | Raw material 2 | 1.9 | 2.2 |
| 4 | Raw material 3 | 1.3 | 2.0 |
| 5 | Starting materials 1 | 5.0 | 2.5 |
| 6 | Starting materials 1 | 4.5 | 1.8 |
Product a was obtained from distillation column and analyzed as shown in table 7 below:
table 7: indices of fatty acid product A from distillation column
Trace means less than 0.005mmol/kg
As can be seen from the fatty acid product A obtained from the distillation column of examples 1 to 6, the iodine value IV thereof was controlled to be<0.25gI2/100g。
The bottom product obtained from the bottom of the distillation column is the heavy phase remaining after removal of its low-boiling components and product A. The indices of the heavy phase are shown in table 8 below. The bottom product from the first distillation column is fed to the second distillation column as feed for product B.
Table 8: index of bottom product of distillation tower
Trace means less than 0.005mmol/kg
The lower boiling components from the distillation column were also analyzed and are shown in Table 9.
Table 9: index of low-boiling-point component of distillation column
Trace means less than 0.005mmol/kg
In the second distillation column, the bottom temperature was controlled to 227-.
Table 10: indexes of fatty acid product B of distillation tower II
Trace means less than 0.005mmol/kg
The iodine number IV of the fatty acid product B obtained from the distillation column, in particular examples 1 to 4, can also be controlled<0.25gI2/100g。
Comparative examples 7 to 10
In comparative examples 7 to 10, the source of the raw material, hydrolysis, hydrogenation and the like in the previous steps were the same as in examples 1 to 6. In the distillation step, the values of M and N were controlled in the ranges shown in Table 11 below by adjusting parameters such as the degree of vacuum, the amount of vapor, the temperature and/or the flow rate.
TABLE 11
| Comparative examples | Source of feed | M | N |
| 7 | Raw material 2 | 1.0 | 2.2 |
| 8 | Raw material 2 | 0.8 | 3.1 |
| 9 | Raw material 3 | 2.1 | 1.6 |
| 10 | Raw material 3 | 3.0 | 3.3 |
At this time, the fatty acid product A obtained by distillation of one column was examined, and the indices are shown in Table 12 below.
Table 12: indices of fatty acid product A from distillation column
Trace means less than 0.005mmol/kg
It can be seen that the fatty acid IV values of the products A of comparative examples 7 to 10 were all much greater than 0.25gI2/100g。
The bottom product obtained from the bottom of the distillation column is the heavy phase remaining after removal of its low-boiling components and product A. The indices of the heavy phase are shown in table 13 below. The bottom product from the first distillation column is fed to the second distillation column as feed for product B.
Table 13: index of distillation column bottom product
The lower boiling components from the distillation column were also analyzed and are shown in Table 14.
Table 14: index of low-boiling-point component of distillation column
The bottom temperature of the second distillation column was controlled to 227-.
Table 15: indexes of fatty acid product B of distillation tower II
Trace means less than 0.005mmol/kg
It is clear that the IV values of the fatty acid products of comparative examples 7-10 are not ideal.
Claims (10)
1. A process for reducing the iodine value of a fatty acid product, said process comprising at least one distillation step in which a saturated fatty acid mixture fed to the at least one distillation step is subjected to a distillation step to produce a fatty acid product, low boiling components and a bottoms product, wherein the saturated fatty acid mixture contains greater than 0 to 1 wt% pentadecenes,
wherein the content of pentadecene in the fatty acid product, the low-boiling component, the bottom product of the column is adjusted in the distillation step so that the condition of 1.2. ltoreq. M '5.0, preferably 1.3. ltoreq. M' 3.6 is satisfied, wherein
Preferably, wherein the content of pentadecene in the fatty acid product, the low-boiling component, the bottom product of the column is adjusted in said distillation step so that the condition 1.8. ltoreq. N '.ltoreq.3.0, preferably 2.0. ltoreq. N'.ltoreq.3.0 is simultaneously satisfied, wherein
2. A process for the production of a fatty acid product comprising a first distillation step in which a saturated fatty acid mixture is fed to a first distillation column and subjected to a first distillation step to produce a first fatty acid product, a first low boiling component and a first bottoms product, wherein the saturated fatty acid mixture contains greater than 0 to 1 wt% pentadecenes,
in the first distillation step, the value of M is adjusted such that 1.2. ltoreq. M.ltoreq.5.0, preferably 1.3. ltoreq. M.ltoreq.3.6, where
3. The production method according to claim 2, wherein the value of N is adjusted in the first distillation step so that 1.8. ltoreq. N.ltoreq.3.0, preferably 2.0. ltoreq. N.ltoreq.3.0, wherein
4. The production method according to any one of claims 1 to 3, wherein the saturated fatty acid mixture contains palmitic acid and/or stearic acid,
preferably, the saturated fatty acid mixture comprises more than 50 wt.%, 60 wt.%, 70 wt.%, 80 wt.%, 90 wt.%, 95 wt.%, 96 wt.%, 97 wt.%, 98 wt.% or 99 wt.% of palmitic acid and/or stearic acid.
5. The production process according to any one of claims 2 to 4, further comprising a second distillation step in which the first bottom product is fed to a second distillation column, resulting in a second fatty acid product, a second lower boiling component and a second bottom product after being treated by the second distillation step,
preferably, the distillation treatment comprises controlling the temperature at the bottom of the second column to 227-.
6. The production method according to any one of claims 2 to 5, further comprising, before the first distillation step, a hydrogenation step in which mixed fatty acids are hydrogenated to thereby obtain the saturated fatty acid mixture.
7. The production method according to claim 6, further comprising, before the hydrogenation step, a hydrolysis step of: hydrolyzing raw material grease into the mixed fatty acid;
preferably, the raw oil is selected from soybean oil, rapeseed oil, peanut oil, cottonseed oil, sunflower seed oil, sesame oil, camellia seed oil, rice bran oil, linseed oil, corn oil, safflower seed oil, palm oil, olive oil, or any mixture thereof, more preferably palm oil.
8. A fatty acid product having an iodine value of less than 0.25 gl produced by the process of any of claims 1-22/100g。
9. A first lipid prepared by the method of any one of claims 2 to 7Fatty acid products having an iodine value of less than 0.25gI2/100g。
10. A second fatty acid product having an iodine value of less than 0.25gI produced by the process of any of claims 3 to 72/100g。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1150448A (en) * | 1994-07-16 | 1997-05-21 | 汉克尔股份两合公司 | Unsaturated fats with improved low-temp behaviour |
| CN1802428A (en) * | 2003-06-10 | 2006-07-12 | 阿彻-丹尼尔斯-米德兰公司 | Method for the production of fatty acids having a low trans-fatty acid content |
| CN106883933A (en) * | 2015-12-16 | 2017-06-23 | 丰益油脂科技（连云港）有限公司 | Coconut oil production method and coconut oil obtained by this method |
-
2019
- 2019-12-12 CN CN201911280728.3A patent/CN112980591A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1150448A (en) * | 1994-07-16 | 1997-05-21 | 汉克尔股份两合公司 | Unsaturated fats with improved low-temp behaviour |
| US5917097A (en) * | 1994-07-16 | 1999-06-29 | Henkel Kommanditgesellschaft Auf Aktien | Unsaturated fatty compounds with improved low-temperature behavior |
| CN1802428A (en) * | 2003-06-10 | 2006-07-12 | 阿彻-丹尼尔斯-米德兰公司 | Method for the production of fatty acids having a low trans-fatty acid content |
| CN106883933A (en) * | 2015-12-16 | 2017-06-23 | 丰益油脂科技（连云港）有限公司 | Coconut oil production method and coconut oil obtained by this method |
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