US2583028A - Improvement of color and color stability of saturated fatty acids - Google Patents
Improvement of color and color stability of saturated fatty acids Download PDFInfo
- Publication number
- US2583028A US2583028A US195462A US19546250A US2583028A US 2583028 A US2583028 A US 2583028A US 195462 A US195462 A US 195462A US 19546250 A US19546250 A US 19546250A US 2583028 A US2583028 A US 2583028A
- Authority
- US
- United States
- Prior art keywords
- color
- fatty acids
- fatty acid
- saturated fatty
- improvement
- 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.)
- Expired - Lifetime
Links
- 235000003441 saturated fatty acids Nutrition 0.000 title claims description 13
- 150000004671 saturated fatty acids Chemical class 0.000 title claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 31
- 229930195729 fatty acid Natural products 0.000 claims description 31
- 239000000194 fatty acid Substances 0.000 claims description 31
- 150000004665 fatty acids Chemical class 0.000 claims description 31
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 28
- 229910015900 BF3 Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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
- C11C1/08—Refining
- C11C1/10—Refining by distillation
- C11C1/103—Refining by distillation after or with the addition of chemicals
Definitions
- the present invention relates to the preparation of saturated higher fatty acids having improved color and color stability.
- the process comprises the treatment of higher saturated fatty acids with a small quantity of boron trifiuoride at a temperature within the approximate range of 70-200 C. for a time period of 2 to 4 hours.
- Small quantities of boron tri fluoride are sufficient to accomplish the desired results.
- A; of 1% by weight of boron trifluoride based on the weight of the fatty acid is sufficient to produce a material improvement in color and color stability.
- One-half of l% by weight of boron trifiuoride is usually sufficient to accomplish the maximum improvement of color and color stability. Quantities of boron trifluoride in excess of of 1% may be used but the improvement in results from the use of the excess usually does not justify the increased cost.
- the boron trifluoride may be used in the form of boron trifluoride itself, which is a gas. It is usually more convenient, however, to employ the boron trifiuoride in the form of its ether complex, in which case it will be appreciated that a sufiiciently increased quantity of the complex should be employed to provide the desired quantity of boron trifluoride.
- the time required is in the upper portion of the time range, and accordingly it is preferred-to carry out the process at temperatures within the range of 1501'75 C. at which temperatures the time required is in the lower portion of the time range.
- the treatment involves the admixture of the boron trifluoride with the fatty acid while the latteris in a liquid condition.
- the admixture may be effected at room temperatures.
- these may be melted first and the boron trifiuoride added thereto.
- the resulting mixture is then heated to temperatures within the range mentioned above and agitated for the time period described.
- the mixture is cooled to about 100 C. and then washed with water until the boron trifiuoride is removed.
- the product is then dried and subjected to distillation. The product obtained upon distillation is much improved in color, in color stability on aging, and in color stability on heating to 205 C.
- the Coleman Junior spectrophotometer was used for the determination of the color of the samples. Color of the samples was determined at five wave lengths- 400, 425, 450, 475, and 500 millimicrons. The color values are stated in percentage transmittance compared with distilled water values: 100 at each of the wave lengths.
- a tube of distilled water was placed in the instrument and the instrument was adjusted such that the reading was equal to 100% at that wave length. Then the distilled water tube was removed and the fatty acid sample was placed in the instrument. The instrument reading was then recorded as a measure of the fatty acid color at that wave length. The instrument readings at the five wave lengths were then averaged numerically and this average figure was designated as the color value in these examples.
- the color of the sample was first determined and the color value was recorded. The melted sample was then poured into a 50 ml. Nessler tube and heated for 2 hours at 205 C. The color of the heat treated sample was again determined in the spectrophotometer and the value was expressed as the color value after heating.
- Example 1 Treated and Freshly Distilled Pefore Flaked Product Treatment 1 Week 2 Weeks 4 Weeks As melted After heating 2 hours at 205 C.
- Control Freshly distilled and untreated, 77.
- Example 2 One hundred parts by weight of a commercial distilled palmiticacid and 1 part by weight of boron trifluoride ethyl ether complex were heated for 4 hours at 150 C'. The product was then cooled to 100 C., washed with water and dried in vacuo, and distilled. The color and color ill . 4 stability of the product were determined and the color values obtained are as follows:
- the process is applicable to higher saturated fatty acids in general. Those derived from ordinary animal and vegetable fats and oils will contain from 8 to about 22 carbon atoms. The process may be applied to isolated saturated fatty acids and to selected fractions of the saturated fatty acids derived from fats or oils, or to complete mixtures of saturated fatty acids occurring in a fat or oil. v It will be apparent that other variations may also be made in the process without departing from the spirit of the invention.
- Process of treating higher saturated fatty acids which comprises mixing a small quantity of boron trifluoride with the fatty acid, heating the mixture to a temperature within the approximate range of -200 C. for a period of from 2 to 4 hours, thereafter washing the mixture with water to remove boron trifluoride, and distilling the residue to recover the fatty acid.
- Process of treating higher saturated fatty acids which comprises mixing approximately 1% of boron trifluoride ethyl ether complex based on the Weight of the fatty acid, with the fatty acid, heating the mixture to a temperature within the approximate range of 150-175 C. for a period of from 2 to 4 hours, thereafter washing the mixture with water to remove boron trifluoride, and distilling the residue to recovery the fatty acid.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 22, 1952 IMPROVEMENT OF COLOR AND COLOR STA- BILITY OF SATURATED FATTY ACIDS David E. Terry and Donald T. Warner, Minneapolis, Minn.,' assignors toGeneral Mills, Inc., a
corporation of Delaware No Drawing. Application November 13,, 1950, Serial No. 195,462
3 Claims. (Cl. 260-398.5)
The present invention relates to the preparation of saturated higher fatty acids having improved color and color stability.
For many uses to which higher saturated fatty acids are put, it is essential that the fatty acids possess a light color and that the color be stable over long periods of time. Fatty acids for such uses are commonly produced by the fractional distillation of hydrolyzed animal and vegetable oils, or from waste products resulting from the processing of such oils. duced, these fatty acids have a fair degree of whiteness but are not sufficiently light in color to be used for many industrial applications. It is essential, therefore, to improve the initial color of these fatty acid products.
While the fatty acids mitially produced by distillation may have a fair color, this color rapidly deteriorates on storage and the product'after a reasonable storage period possesses such a poor color that it can be used only for uses which command a low price.
This degradation in color is apparently caused by certain color forming bodies which are present in the fatty acids initially, but which are colorless at that point. Upon exposure to air and light these color forming bodies are converted into compounds which are colored and which thus color the entire body of fatty acid.
It is essential, therefore, to treat these fatty acid products not only to improve their initial color, but to give the'fatty acid products'color stability for a long period of time.
l-leretofore the improvement in color of fatty acids and fatty products has been accomplished by various bleaching methods, principally by means of the use of various bleaching agents such as the bleaching earths, activated carbon, and the like. These methods have been subject to various disadvantages. The bleaching agents employed are relatively expensive and in their use they entrain considerable quantities of the fatty acids being treated thereby reducing the tion to provide a novel process of treating higher saturated fatty acids with boron trifiuoride to improve the initial color and to improve the color stability of the fatty acids.
The process comprises the treatment of higher saturated fatty acids with a small quantity of boron trifiuoride at a temperature within the approximate range of 70-200 C. for a time period of 2 to 4 hours. Small quantities of boron tri fluoride are sufficient to accomplish the desired results. Thus A; of 1% by weight of boron trifluoride based on the weight of the fatty acid is sufficient to produce a material improvement in color and color stability. One-half of l% by weight of boron trifiuoride is usually sufficient to accomplish the maximum improvement of color and color stability. Quantities of boron trifluoride in excess of of 1% may be used but the improvement in results from the use of the excess usually does not justify the increased cost. The boron trifluoride may be used in the form of boron trifluoride itself, which is a gas. It is usually more convenient, however, to employ the boron trifiuoride in the form of its ether complex, in which case it will be appreciated that a sufiiciently increased quantity of the complex should be employed to provide the desired quantity of boron trifluoride.
4 At the lower portion of the temperature range, the time required is in the upper portion of the time range, and accordingly it is preferred-to carry out the process at temperatures within the range of 1501'75 C. at which temperatures the time required is in the lower portion of the time range.
The treatment involves the admixture of the boron trifluoride with the fatty acid while the latteris in a liquid condition. In the case of fatty acids which are liquid at normal temperature, the admixture may be effected at room temperatures. In the case of the higher melting fatty acids, these may be melted first and the boron trifiuoride added thereto. The resulting mixture is then heated to temperatures within the range mentioned above and agitated for the time period described. Following the treatment, the mixture is cooled to about 100 C. and then washed with water until the boron trifiuoride is removed. The product is then dried and subjected to distillation. The product obtained upon distillation is much improved in color, in color stability on aging, and in color stability on heating to 205 C.
In the following examples the Coleman Junior spectrophotometer was used for the determination of the color of the samples. Color of the samples was determined at five wave lengths- 400, 425, 450, 475, and 500 millimicrons. The color values are stated in percentage transmittance compared with distilled water values: 100 at each of the wave lengths. Thus, for
example, a tube of distilled water was placed in the instrument and the instrument was adjusted such that the reading was equal to 100% at that wave length. Then the distilled water tube was removed and the fatty acid sample was placed in the instrument. The instrument reading was then recorded as a measure of the fatty acid color at that wave length. The instrument readings at the five wave lengths were then averaged numerically and this average figure was designated as the color value in these examples.
In the heat stability test the color of the sample was first determined and the color value was recorded. The melted sample was then poured into a 50 ml. Nessler tube and heated for 2 hours at 205 C. The color of the heat treated sample was again determined in the spectrophotometer and the value was expressed as the color value after heating.
The storage of the fatty acid samples for the tests. after 1, 2 and 4 weeks was accomplished by flaking the fatty acid samples and then storing them in glass bottles with free exposure to the air. These samples were tested at intervals for color stability both before and after heating at 205 C. 7
Example 1 Treated and Freshly Distilled Pefore Flaked Product Treatment 1 Week 2 Weeks 4 Weeks As melted After heating 2 hours at 205 C.
Control: Freshly distilled and untreated, 77.
Freshly distilled and untreated, heated 2 hours at 205 0., 39.
Example 2 One hundred parts by weight of a commercial distilled palmiticacid and 1 part by weight of boron trifluoride ethyl ether complex were heated for 4 hours at 150 C'. The product was then cooled to 100 C., washed with water and dried in vacuo, and distilled. The color and color ill . 4 stability of the product were determined and the color values obtained are as follows:
The process is applicable to higher saturated fatty acids in general. Those derived from ordinary animal and vegetable fats and oils will contain from 8 to about 22 carbon atoms. The process may be applied to isolated saturated fatty acids and to selected fractions of the saturated fatty acids derived from fats or oils, or to complete mixtures of saturated fatty acids occurring in a fat or oil. v It will be apparent that other variations may also be made in the process without departing from the spirit of the invention.
We claim as our invention:
1. Process of treating higher saturated fatty acids which comprises mixing a small quantity of boron trifluoride with the fatty acid, heating the mixture to a temperature within the approximate range of -200 C. for a period of from 2 to 4 hours, thereafter washing the mixture with water to remove boron trifluoride, and distilling the residue to recover the fatty acid.
2. Process of treating higher saturated fatty acids which comprises mixin approximately /2 of 1% of boron trifluoride based on the weight of the fatty acid, with the fatty acid, heating the mixture to a temperature within the approximate range of -1'75" C. for a period of from 2 to 4 hours, therafter washing the mixture with water to remove boron trifluoride, and distilling the residue to recover the fatty acid.
3. Process of treating higher saturated fatty acids which comprises mixing approximately 1% of boron trifluoride ethyl ether complex based on the Weight of the fatty acid, with the fatty acid, heating the mixture to a temperature within the approximate range of 150-175 C. for a period of from 2 to 4 hours, thereafter washing the mixture with water to remove boron trifluoride, and distilling the residue to recovery the fatty acid.
DAVID E. TERRY. DONALD T. WARNER.
No references cited.
Claims (1)
1. A PROCESS OF TREATING HIGHER SATURATED FATTY ACIDS WHICH COMPRISES MIXING A SMALL QUANTITY OF BORON TRIFLUORIDE WITH THE FATTY ACID, HEATING THE MIXTURE TO A TEMPERATURE WITHIN THE APPROXIMATE RANGE OF 70-200* C. FOR A PERIOD OF FROM 2 TO 4 HOURS, THEREAFTER WASHING THE MIXTURE WITH WATER TO REMOVE BORON TRIFLUORIDE, AND DISTILLING THE RESIDUE TO RECOVER THE FATTY ACID.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US195462A US2583028A (en) | 1950-11-13 | 1950-11-13 | Improvement of color and color stability of saturated fatty acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US195462A US2583028A (en) | 1950-11-13 | 1950-11-13 | Improvement of color and color stability of saturated fatty acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2583028A true US2583028A (en) | 1952-01-22 |
Family
ID=22721513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US195462A Expired - Lifetime US2583028A (en) | 1950-11-13 | 1950-11-13 | Improvement of color and color stability of saturated fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2583028A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2862943A (en) * | 1954-10-07 | 1958-12-02 | Gen Mills Inc | Purification of fatty acids |
| US3396182A (en) * | 1966-01-21 | 1968-08-06 | Scm Corp | Process for recovery of purified saturated higher fatty acid from fatty acid fractions |
| DE2939242A1 (en) | 1978-09-27 | 1980-04-17 | Nippon Oils & Fats Co Ltd | METHOD FOR PURIFYING FATTY ACIDS |
| US4650611A (en) * | 1981-07-20 | 1987-03-17 | Henkel Kommanditgesellschaft Auf Aktien | Process for the preparation of fatty acid alkyl esters having improved processing properties |
| DE19531806C1 (en) * | 1995-08-30 | 1997-04-10 | Henkel Kgaa | Fine distillation of 6-24C fatty acids from plant or animal fats etc. |
| US20060167291A1 (en) * | 2003-07-10 | 2006-07-27 | Akzo Nobel N.V. | Process for preparing purified fatty acids |
-
1950
- 1950-11-13 US US195462A patent/US2583028A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2862943A (en) * | 1954-10-07 | 1958-12-02 | Gen Mills Inc | Purification of fatty acids |
| US3396182A (en) * | 1966-01-21 | 1968-08-06 | Scm Corp | Process for recovery of purified saturated higher fatty acid from fatty acid fractions |
| DE2939242A1 (en) | 1978-09-27 | 1980-04-17 | Nippon Oils & Fats Co Ltd | METHOD FOR PURIFYING FATTY ACIDS |
| US4650611A (en) * | 1981-07-20 | 1987-03-17 | Henkel Kommanditgesellschaft Auf Aktien | Process for the preparation of fatty acid alkyl esters having improved processing properties |
| DE19531806C1 (en) * | 1995-08-30 | 1997-04-10 | Henkel Kgaa | Fine distillation of 6-24C fatty acids from plant or animal fats etc. |
| US20060167291A1 (en) * | 2003-07-10 | 2006-07-27 | Akzo Nobel N.V. | Process for preparing purified fatty acids |
| US7560579B2 (en) | 2003-07-10 | 2009-07-14 | Oleon N.V. | Process for preparing purified fatty acids |
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