US2903369A - Edible oils - Google Patents

Edible oils Download PDF

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Publication number
US2903369A
US2903369A US641026A US64102657A US2903369A US 2903369 A US2903369 A US 2903369A US 641026 A US641026 A US 641026A US 64102657 A US64102657 A US 64102657A US 2903369 A US2903369 A US 2903369A
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Prior art keywords
oil
amine
taste
edible oils
added
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US641026A
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Hampson George Charlesworth
Freeman Ian Penn
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Lever Brothers Co
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Lever Brothers Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C11B5/005—Amines or imines

Definitions

  • This invention relates to edible oils and more particularly to a process for thetreatment'of edible oils.
  • edible oils may tend to develop an objectionable rubber-like taste on exposure to ultraviolet light or to radiation containing ultra-violet light, such as bright sunlight. This tendency is believed to be due to the presence of minute amounts of undesirable sulphur-containing impurities in the oil.
  • the present invention provides, therefore, a process which consists of incorporating a minor amount of a C C primary aliphatic amine in an edible oil.
  • the invention also includes edible oils containing a minor amount of a (I -C primary aliphatic amine.
  • Primary aliphatic amines for use according to the invention may have either straight or branched aliphatic hydrocarbon chains and may be saturated or unsaturated.
  • suitable amines there may be mentioned stearylamine, laurylamine, and oleylamine. These are all amines of the formula RNH where R is an aliphatic hydrocarbon radical containing 12 to 18 carbon atoms.
  • the amine may be added to the oil at any suitable stage in the processing of the oil provided that subsequent treatment does not destroy or substantially alter the amine.
  • the bleaching step should thus not be carried out after the amine has been added. It has been found preferable to add the amine at the end of the deodorization stage.
  • neutralised, bleached and filtered oil may be charged into the deodorizer and deodorization carried out in the normal way.
  • the amine may be added, either as such or as a solution in a portion of the oil, whilst the oil is cooling down.
  • the solution of the amine may, for example, be added at about 60 C. and open steam may then be allowed to pass through the oil for a short while before the treated oil is allowed to cool to its final dropping temperature.
  • the amine may be added to an oil which has not developed a rubber-like taste to prevent or reduce the formation of such a taste or it may be added to an oil in which a rubber-like taste has already developed, when it will serve to reduce or remove the rubber-like taste.
  • Example 1 A sample of crude coconut oil (free fatty acid 8%, sulphur content 12 p.p.m.) was neutralised by stirring with 2,903,369 Patented Sept. 8, 1959 4 N NaOH. After separating ofi the soap the oil was dried with 2% fullers earth and bleached with 1% activated fullers earth at 100-110" C. under carbon dioxide. The oil was then deodorized in an all-glass laboratory apparatus at 180 C. and a pressure of 1-2 mm. Hg for 3 rylamine remained free from rubbery flavour.
  • Example 2 ring with 4 N NaOH. After separating oil the soap, the
  • Example 3 A sample of crude coconut oil (free fatty acid 8%, sulphur content 12 p.p.m.) was neutralised by stirring with 4 N NaOH. After separating the soap, the oil was dried with 2% fullers earth and bleached with 1% activated fullers earth at 100-110 C. under carbon dioxide. The oil was then deodorized in an all-glass laboratory apparatus at 180 C. and a pressure of 1-2 mm. for 3 hours. The deodorized oil was then divided into two parts. To one part was added 0.02% laurylamine. Both samples were exposed to ultraviolet light for 30 seconds when the sample without laurylamine developed a strong rubbery flavour while the sample containing laurylamine remained free from rubbery flavour.
  • Example 4 A sample of refined, bleached and deodorized coconut oil (sulphur content 12 p.p.m.) had a slightly rubbery taste. 0.02%, by weight of the oil, of commercial oleylamine (derived from commercial oleine) which had been deodorized in an all-glass laboratory apparatus at C. and a pressure of 1-2 mms. for 3 hours, was added to the oil. After a short time the sample was examined and the rubbery taste had disappeared.
  • commercial oleylamine derived from commercial oleine
  • Process for producing an improved oil which comprises incorporating in an oil selected from the class consisting of coconut oil and palm kernel oil, a minor pro portion of an amine of the formula RNH where R is an aliphatic hydrocarbon radical containing 12 to 18 carbon atoms.
  • a composition comprising an oil selected from the class consisting of coconut oil and palm kernel oil and a minor proportion of an amine of the formula RNH; where R is an aliphatic hydrocarbon radical containing 12 to 18 carbonatoms.
  • a composition according to claim 12 wherein the amine is stearylamine.
  • composition according to claim 12 wherein the amine is laurylamine.
  • a composition according to claim 12 wherein the amine is oleylamine.
  • composition according to claim 16 wherein the amine is stearylamine.
  • composition according to claim 16 wherein the amine is laurylamine.
  • composition according to claim 16 wherein the amine is oleylamine.

Description

United States. Patent M 1 2,903,369 EDIIBLE OILS George Charlesworth Hampson, Neston, Wirrahaud Ian Penn Freeman, Prenton, Birkenhead, England, assignors to Lever Brothers Company, New York, N.Y., a corporation of Maine No Drawing. Application February 19, 1957 Serial No. 641,026
Claims priority, application Great Britain February 23, 1956 19 Claims. (Cl. 99-163) This invention relates to edible oils and more particularly to a process for thetreatment'of edible oils.
It has been found that edible oils may tend to develop an objectionable rubber-like taste on exposure to ultraviolet light or to radiation containing ultra-violet light, such as bright sunlight. This tendency is believed to be due to the presence of minute amounts of undesirable sulphur-containing impurities in the oil.
We have found that this tendency to develop an objectionable taste may be prevented or reduced by incorporating in the oil a minor amount of a C C primary aliphatic amine.
The present invention provides, therefore, a process which consists of incorporating a minor amount of a C C primary aliphatic amine in an edible oil.
The invention also includes edible oils containing a minor amount of a (I -C primary aliphatic amine.
Primary aliphatic amines for use according to the invention may have either straight or branched aliphatic hydrocarbon chains and may be saturated or unsaturated. As examples of suitable amines there may be mentioned stearylamine, laurylamine, and oleylamine. These are all amines of the formula RNH where R is an aliphatic hydrocarbon radical containing 12 to 18 carbon atoms.
Edible oils which may be treated according to the invention include coconut oil, and palm kernel oil.
As little as 0.01% of the amine, by weight of the oil, may reduce the tendency of the oil to develop an objectionable taste. Usually about 0.02% will be used and not more than 0.05% should be required. It may be possible to relate the amount of amine required to the sulphur content of the oil.
The amine may be added to the oil at any suitable stage in the processing of the oil provided that subsequent treatment does not destroy or substantially alter the amine. The bleaching step should thus not be carried out after the amine has been added. It has been found preferable to add the amine at the end of the deodorization stage.
For example, neutralised, bleached and filtered oil may be charged into the deodorizer and deodorization carried out in the normal way. The amine may be added, either as such or as a solution in a portion of the oil, whilst the oil is cooling down. The solution of the amine may, for example, be added at about 60 C. and open steam may then be allowed to pass through the oil for a short while before the treated oil is allowed to cool to its final dropping temperature.
The amine may be added to an oil which has not developed a rubber-like taste to prevent or reduce the formation of such a taste or it may be added to an oil in which a rubber-like taste has already developed, when it will serve to reduce or remove the rubber-like taste.
The following examples illustrate the invention.
Example 1 A sample of crude coconut oil (free fatty acid 8%, sulphur content 12 p.p.m.) was neutralised by stirring with 2,903,369 Patented Sept. 8, 1959 4 N NaOH. After separating ofi the soap the oil was dried with 2% fullers earth and bleached with 1% activated fullers earth at 100-110" C. under carbon dioxide. The oil was then deodorized in an all-glass laboratory apparatus at 180 C. and a pressure of 1-2 mm. Hg for 3 rylamine remained free from rubbery flavour.
Example 2 ring with 4 N NaOH. After separating oil the soap, the
oil was dried with 2% fuller's earth and bleached with 1% activated fullers earth at ll0 C. under carbon dioxide. The oil was then deodorized in an all-glass laboratory apparatus at 180 C. and a pressure of l-2 mm. for 3 hours. The deodorized oil was then divided into two parts. To one part was added 0.02% stearylamine. Both samples were exposed to ultra-violet light for 30 seconds, when the sample without stearylamine developed a strong rubbery flavour while the sample containing stearylamine remained free from rubbery flavour.
Example 3 A sample of crude coconut oil (free fatty acid 8%, sulphur content 12 p.p.m.) was neutralised by stirring with 4 N NaOH. After separating the soap, the oil was dried with 2% fullers earth and bleached with 1% activated fullers earth at 100-110 C. under carbon dioxide. The oil was then deodorized in an all-glass laboratory apparatus at 180 C. and a pressure of 1-2 mm. for 3 hours. The deodorized oil was then divided into two parts. To one part was added 0.02% laurylamine. Both samples were exposed to ultraviolet light for 30 seconds when the sample without laurylamine developed a strong rubbery flavour while the sample containing laurylamine remained free from rubbery flavour.
Example 4 A sample of refined, bleached and deodorized coconut oil (sulphur content 12 p.p.m.) had a slightly rubbery taste. 0.02%, by weight of the oil, of commercial oleylamine (derived from commercial oleine) which had been deodorized in an all-glass laboratory apparatus at C. and a pressure of 1-2 mms. for 3 hours, was added to the oil. After a short time the sample was examined and the rubbery taste had disappeared.
On exposure to ultra-violet light for 30 seconds, no rubbery taste developed. A sample of the coconut oil without added oleylamine, on exposure to ultra-violet light for 30 seconds, developed a strong rubbery flavour.
We claim:
1. Process for producing an improved oil, which comprises incorporating in an oil selected from the class consisting of coconut oil and palm kernel oil, a minor pro portion of an amine of the formula RNH where R is an aliphatic hydrocarbon radical containing 12 to 18 carbon atoms.
2. Process according to claim 1 wherein said oil has a rubber-like taste.
3. Process according to claim 1 wherein the oil is coconut oil.
4. Process according to claim 1 wherein the oil is palm kernel oil.
5. Process according to claim 1 wherein the oil is coconut oil and the amine is stearylamine.
6. Process according to claim 1 wherein the oil is palm kernel oil and the amine is stearylamine.
7. Process according to claim 1 wherein the oil is coconut oil and the amine islaurylamine.
8. Process according to claim 1 wherein the oil is palm kernel oil and the amine is laurylamine.
9. Process according to claim 1 wherein the oil is coconut oil and the amine is oleylamine.
10. Process according to claim 1 wherein the oil is palm kernel oil and the amine is oleylamine.
11. A composition comprising an oil selected from the class consisting of coconut oil and palm kernel oil and a minor proportion of an amine of the formula RNH; where R is an aliphatic hydrocarbon radical containing 12 to 18 carbonatoms.
12. A composition containing coconut oil together with 0.01 to 0.05% of its weight of an amine of the formula RNH where R is an aliphatic hydrocarbon radical containing 12 to 18 carbon atoms.
13. A composition according to claim 12 wherein the amine is stearylamine.
14. A composition according to claim 12 wherein the amine is laurylamine.
15. A composition according to claim 12 wherein the amine is oleylamine.
16. A composition containing palm kernel oil together with 0.01 to 0.05% of its weight of an amine of the formula RNH where R is an aliphatic hydrocarbon radical containing 12 to 18 carbon atoms.
17. A composition according to claim 16 wherein the amine is stearylamine.
18. A composition according to claim 16 wherein the amine is laurylamine.
19. A composition according to claim 16 wherein the amine is oleylamine.
References Cited in the file of'this patent UNITED STATES PATENTS Hunt et al. Dec. 8, 1936 Klaui Sept. 25, 1956

Claims (1)

1. PROCEES FOR PRODUCING AN IMPROVED OIL, WHICH COMPRISES INCORPORATING IN AN OIL SELECTED FROM THE CLASS CONSISTING OF COCONUT OIL AND PALM KERNEL OIL, A MINOR PROPORTION OF AN AMINE OF THE FORMULA RNH2 WHERE R IS AN ALIPHATIC HYDROCARBON RADICAL CONTAINING 1I TO 18 CARBON ATOMS.
US641026A 1956-02-23 1957-02-19 Edible oils Expired - Lifetime US2903369A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2063602A (en) * 1935-02-15 1936-12-08 Du Pont Stabilization of animal and vegetable fats and oils
US2764520A (en) * 1952-08-20 1956-09-25 Hoffmann La Roche Stabilized vitamin a compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2063602A (en) * 1935-02-15 1936-12-08 Du Pont Stabilization of animal and vegetable fats and oils
US2764520A (en) * 1952-08-20 1956-09-25 Hoffmann La Roche Stabilized vitamin a compositions

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