US3836554A - Process for the lightening and color stabilization of fatty-acid fore-runnings - Google Patents
Process for the lightening and color stabilization of fatty-acid fore-runnings Download PDFInfo
- Publication number
- US3836554A US3836554A US00167014A US16701471A US3836554A US 3836554 A US3836554 A US 3836554A US 00167014 A US00167014 A US 00167014A US 16701471 A US16701471 A US 16701471A US 3836554 A US3836554 A US 3836554A
- Authority
- US
- United States
- Prior art keywords
- acid
- fatty
- forerunnings
- lightening
- silicon
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title abstract description 42
- 229930195729 fatty acid Natural products 0.000 title abstract description 42
- 239000000194 fatty acid Substances 0.000 title abstract description 42
- 150000004665 fatty acids Chemical class 0.000 title abstract description 42
- 238000000034 method Methods 0.000 title abstract description 20
- 238000011105 stabilization Methods 0.000 title abstract description 8
- 230000006641 stabilisation Effects 0.000 title description 5
- 229910052710 silicon Inorganic materials 0.000 abstract description 23
- 239000010703 silicon Substances 0.000 abstract description 23
- 238000010438 heat treatment Methods 0.000 abstract description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229910000519 Ferrosilicon Inorganic materials 0.000 description 1
- DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 239000000061 acid fraction Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- This invention relates to a unique process for the lightening and color stabilization of first fraction fatty acids or fatty-acid forerunnings wherein the fatty acids are heated with technical-grade silicon.
- this invention is directed to a process for the lightening and color stabilization of fatty-acid forerunnings having a chain length of C C which is characterized in that technical-grade silicon is employed in place of alkyl esters of silicic acid or polysilicic acid, respectively; the fatty acids are heated with about 0.1 to about 0.6%, preferably about 0.2 to about 0.3% by weight, of technical-grade silicon for a period of about 0.5 to about 4 hours, preferably about 1 to about 3 hours, under normal pressure to temperatures of about 180 C. to about 250 C., preferably about 200 C. to about 240 C.; and the acids are then distilled under vacuum. It will be understood that heating may be effected at higher pressures, i.e. about atmospheric, e.g. about 5 atmospheres gauge, but atmospheric pressure is generally preferred.
- the impurities in the fatty acids remain, after the treatment, in the distillation residue bound to the silicon.
- the process has the advantage that even after the treatment with technical-grade silicon and the subsequent distillation, the present distillate does not have any larger amounts of unsaponifiable compounds than the distillate of the untreated fatty acids.
- the distillation 3,836,554 Patented Sept. 17, 1974 residue of the treated fatty acids does not contain any newly formed condensation products, as is the case in the conventional processes for preventing discoloration utilizing boric acid or boric acid esters.
- the boron compounds have the effect of Lewis catalysts and promote the formation of unsaponifiable, nondistillable condensation products.
- the color stability of the fatty-acid forerunnings treated in accordance with this invention and for comparison purposes, the color stability of the untreated fatty-acid forerunnings were determined by heating samples in a capped glass tube having a diameter of 14 millimeters and a filling level of 115 millimeters to 200 C. for a period of 6 hours. This heating test was conducted in a drying oven equipped with a thermostat which was not opened during the entire duration of the test.
- the color intensity was measured in iodine color values wherein the iodine color value indicates how many milligrams of free iodine is contained in 100 milliliters of aqueous iodine-potassium iodide solution at the same depth of color when measured at a layer thickness of 25 millimeters.
- the iodine color value (ICV) and the hazen color value (HCV) were measured in a Lovibond 1000 comparator and its accessories by Tintometer. It will be appreciated that the process of the present invention can be conducted discontinuously as Well as continuously.
- EXAMPLE 1 (a) The fatty-acid forerunnings of coconut-palm nut refinery fatty acid employed, i.e. the untreated fatty acid fraction, exhibited the following composition in accordance with gas chromatographic analysis (numerical data in percent by weight): C -acid: 0.5; C -acidz 54.6; C acid: 42.8; C -acid: 1.8; and C -acid: 0.3. The acid fraction also contained about 2% of water. These forerunnings were dewatered under agitation and mixed, at a temperature of about 220 C., with 0.2% by weight of technical-grade silicon. Then the reaction mixture was heated to about 240 C., and this temperature was maintained for about 3 hours.
- fraction I 7.0% by weight was obtained; as fraction II, 82.6% by weight, and as fraction III, 6.3% by weight, based on the anhydrous fatty-acid forerunnings employed.
- the amount of residue was 4.1% by weight.
- EXAMPLE 2 Fatty-acid forerunnings from the pressure cleaving, i.e. cracking, of coconut oil and palm nut oil were dewatered at 450 torr and mixed at a temperature of 220 C., with 0.2% by weight of technical-grade silicon. During a period of 3 hours a temperature of 240 C. was then maintained. Subsequently, the temperature was reduced by cooling to 90 C. and the thus-treated fatty acid forerunnings were distilled under a vacuum of 1-2 tort over a small distillation column; within about 2 hours three fractions were taken off.
- fraction I 7.5% was obtained; as fraction II, 82.2% 'by weight, and as fraction III, 6.5% by weight.
- the residue was 3.8% by weight.
- silicon of greater or less purity may also be efiectively employed, the technical-grade being preferred because of its availability and cost.
- silicon known products which are silicon in mixture with certain impurities or silicon produced by melting and refining processes, which products are silicides of some metals, partly the metals being present as impurities, partly metals being present as a desired metal content, i.e. in ferro silicon alloys.
- metals are e.g. alkali metals and/or alkaline earth metals as Na, K, Mg or Ca; Al, B or Ti; heavy metals as Ni, Fe, Mn as caused by raw materials of said melting processes, while other elements as C, P, 0, N, S are present as impurities of only small amount.
- Some of these products having only silicon contents of 15 to 45 wt. percent, most of 45 to 98 wt. percent Si.
- a process for the lightening and color-stabilization of fatty acid forerunnings containing from 8 to 12 carbon atoms which comprises heating the fatty acids with about 0.1 to 0.6% by weight of technical-grade silicon for about 0.5 to about 4 hours under normal pressure at a temperature of about C. to about 250 C. and thereafter recovering the treated fatty acids by distillation.
Landscapes
- 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)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038804A DE2038804C3 (de) | 1970-08-05 | 1970-08-05 | Verfahren zur Aufhellung und Farbstabilisierung von Vorlauffettsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3836554A true US3836554A (en) | 1974-09-17 |
Family
ID=5778856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00167014A Expired - Lifetime US3836554A (en) | 1970-08-05 | 1971-07-28 | Process for the lightening and color stabilization of fatty-acid fore-runnings |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3836554A (fr) |
| BE (1) | BE769985R (fr) |
| DE (1) | DE2038804C3 (fr) |
| DK (1) | DK134822C (fr) |
| FR (1) | FR2105848A6 (fr) |
| GB (1) | GB1352408A (fr) |
| IT (1) | IT985508B (fr) |
| NL (1) | NL7108954A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1970
- 1970-08-05 DE DE2038804A patent/DE2038804C3/de not_active Expired
-
1971
- 1971-06-29 NL NL7108954A patent/NL7108954A/xx unknown
- 1971-07-13 GB GB3289671A patent/GB1352408A/en not_active Expired
- 1971-07-14 BE BE769985A patent/BE769985R/fr active
- 1971-07-14 DK DK347171A patent/DK134822C/da active
- 1971-07-28 US US00167014A patent/US3836554A/en not_active Expired - Lifetime
- 1971-08-05 FR FR7128805A patent/FR2105848A6/fr not_active Expired
- 1971-08-05 IT IT27218/71A patent/IT985508B/it active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1352408A (en) | 1974-05-08 |
| IT985508B (it) | 1974-12-10 |
| BE769985R (fr) | 1972-01-14 |
| DK134822C (da) | 1977-07-18 |
| DK134822B (da) | 1977-01-24 |
| DE2038804B2 (fr) | 1979-05-03 |
| DE2038804A1 (de) | 1972-02-10 |
| DE2038804C3 (de) | 1980-01-17 |
| FR2105848A6 (fr) | 1972-04-28 |
| NL7108954A (fr) | 1972-02-08 |
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