US2026395A - Process for increasing the vitamin content of vitamin bearing oils - Google Patents
Process for increasing the vitamin content of vitamin bearing oils Download PDFInfo
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- US2026395A US2026395A US663425A US66342533A US2026395A US 2026395 A US2026395 A US 2026395A US 663425 A US663425 A US 663425A US 66342533 A US66342533 A US 66342533A US 2026395 A US2026395 A US 2026395A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
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- the present invention it is rendered possible to increase the vitamin potency of vitamin bearing oils by almost any desired multiple.
- the process is carried out at moderate temperatures throughout and the harmful effects i which relatively high temperatures have upon vitamins is thereby fully avoided.
- the vitamins and any other active principles which may exist in the oil are automatically transferred from a portion of the oil which is i. destroyed to an unchanged portion, thereby securing the advantage of higher yields and avoiding the harmful eifects of extraction and distilling the solvents from the extracts.
- the finely concentrated oil. is of a light pale color with little but the natural taste and odor.
- An important object of the present invention is to leave unchanged a portion ofv the original vitamin bearing oil'so that this unchanged portion may be enriched and activated to substantially any desired degree with vitamins and other active principles in the original oil.
- a further important object of the invention is to utilize solvents for the water soluble soaps formed and not solvents for the concentrations of vitamins which take place in the unsaponifled portions of the original oil. This permits the use of a far wider range of solvents since organic solvents may be used and even synthetic solvents which are also soluble in water and will dissolve the water soluble soaps formed.
- I may achieve the objects of this invention in various different ways.
- I can break up a portion of the glycerides which compose the oil by means of an alkali, conveniently sodium or potassium hydroxide, although any alkali which will form water soluble soaps with the glycerides may be used.
- the unsaponiflable matter including the vitamins which was associated with these glycerides will now become associated with the unchanged portion of the oil.
- This oil is then separated from the snaps formed by dissolving the mixture in a suflicient quantity of aqueous alcohol or other mixtures capable of dissolving the soap.
- the solvent used may be any organic solvent or solvents which in conjunction with each other or with water have the power of dissolving the water soluble soaps so as to form solutions of relatively low viscosity.
- These solvent mixtures will dissolve the acid soaps present as well as the neutral soaps and permit the globules of oil to rise to the surface of the quiescent mixture and coalesce as a clear layer of oil.
- the utilization of a centrifuge on the mixture im-' proves the efllciency of the process and the clarity of the oil.
- a second method of effecting the objects of my invention may be carried out as follows.
- a quantity of oil is continuously agitated with a solution of an alkali which will form water soluble 40 soaps in aqueous alcohol or any of the soap solvent mixtures mentioned above until all interaction between the oil and alkali has ceased.
- a portion of the glycerides which compose the oil will have been saponified.
- the mixture will show an acid reaction to phenolphthalein dissolved in ethyl alcohol.
- the quantity of alkali used it must be remembered, is less than that necessary to completely saponify the oil.
- the actual amount of the alkali used will depend upon the degree to which it is desired to concentrate the oil. The amount of alkali used therefore affords the operator a conv trol over the concentration of vitamins desired in the final oil.
- Example I Cod liver oil may be used as the vitamin bearing oil, it being well known that this oil is rich in the fat-soluble vitamins known as A and "D.
- a and D fat-soluble vitamins
- Example II A quantity of cod liver oil is continuously agitated with a solution of potassium hydroxidein aqueous ethyl alcohol until the mixture shows an acid reaction to phenolphthalein in ethyl alcohol.
- the quantity of potassium hydroxide used must be less than that necessary to completely saponify the oil.
- the alcohol-water mixture used may suitably contain about 30% by volume of ethanol, of which about fifteen parts by weight should be used for each part of potassium hydroxide.
- the mixture is allowed to remain quiet until the unchanged oil has separated on top of the main body of the soap solution in the form of a thick emulsion.
- the bottom soap layer is then drawn off and the oil washed first with a quantity 10 of 30% ethanol solution, then with a dilute mineral acid to break up any remaining soap, and finally with water until the. washings are no longer acid.
- Example IlI.-A quantity of cod liver oil is continuously agitated at 50-55 C. with a solution of potassium hydroxide in a carbitol-water mixture until the mixture shows an acid reaction to phenolphthalein in ethyl alcohol. The mixture is then allowed to stand until the oil 20 has separated on top in the form of a thick emulsion. The bottom soap layer is then drawn off and the oil washed first with water, then with dilute mineral acid, and finally with water until the washings are no longer acid. 25
- the quantity of potassium hydroxide used depends upon the extent to which it is desired to concentrate the oil, but must be less than the amount necessary to completely saponify the oil used.
- the carbitol-water mixture may suit- 30 ably contain about 30% by volume of carbitol, of which about seventeen parts by weight should be used for each part of potassium hydroxide.
- Example I V.--A quantity of cod liver oil is continuously agitated at 50-55 C. with a quantity 3 of potassium hydroxide dissolved in a mixture of diacetone and water until the mixture shows an acid reaction to phenolphthalein when dissolved in alcohol.
- the quantity of potassium hydroxide used must be less than the amount neces- 40 sary to completely saponify the oil.
- the solvent solution may consist of about 4 parts by weight of diacetone and about 10 parts by weight of water for each part of potassium hydroxide used.
- the mixture is :5 allowed to stand until the oil has separated on top in the form of a concentrated emulsion.
- the bottom soap layer is then drawn off and the oil layer washed first with water, then with dilute mineral acid, and finally with water until the 50 washings are no longer acid.
- the oil is then steamed in vacuo to remove any remaining odor of the diacetone.
- Example V.--A quantity of cod liver oil is continuously agitated at 50-60 C. with a quan- 5 tiiy of potassium hydroxide dissolved in a mixture of diethylene glycol and water until the mixture shows an acid reaction to phenolphthalein dissolved in ethyl alcohol.
- the quantity of potassium hydroxide must be less than the 0) amount necessary to completely saponify the oil.
- the solvent solution may be a mixture consisting of 30% by volume of diethylene glycol and 70% by volume of water, of which about 17 parts by weight should be used for each part of potassium hydroxide.
- the mixture is allowed to stand until the oil has separated on top in the form of a thick emulsion.
- the bottom soap layer is then drawn off and the oil washed first with water, then with dilute acid, and again with water until the washings are no longer acid.
- Example VI.-A quantity oi cod liver oil is continuously agitated at 50-60 C. with a mixture of potassium hydroxide, water and butyl cellosolve until the mixture shows an acid reaction to phenolphthalein in ethyl alcohol.
- the quantity of potassium hydroxide must be less than the amount necessary to completely saponify the oil.
- the amount of solvents used should be about 3 parts by weight of butyl cellusolve and 12 parts by weight of water to each part of potassium hydroxide.
- the mixture is allowed to stand until the oil has separated on top in the form of a thick emulsion.
- the bottom layer of soap is then drawn oil and the oil layer washed first with water, then with dilute acid and again several times with water.
- the oil is then steamed in vacuo to remove any remaining odor of the butyl cellosolve.
- Aseadditional alkalies may be mentioned sodium carbonate and potassium carbonate.
- the following may also be used as solvents for the soaps formed: ethylene glycol, acetone, propanol (normal propyl alcohol), isopropanol (iso propyl alcohol) butanol (normal butyl alcohol), iso butanol (iso butyl alcohol) and butyl carbitol.
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Description
Pate ted Dec. 31, 1935 UNITED STATES PROCESS FOR INCREASING THE VITAMIN CONTENT OF VITAMIN BEARING OILS Horatio Porter Loomis, Vineland, N. 1., assigninto Silmo Chemical Company, Inc., Vineland,
No Drawing. Application March as, 1933, Serial No. 663,425
11 Claims. (Cl. 167-81) This invention relates to a new article and a process for increasing the vitamin content of vitamin bearing oils. 7
The use of vitamins both for human consumption and animal consumption has increased considerably in the last few years. The usual practice in the art of extracting vitamins from vitamin bearing oils is to form a soap of the saponii'lable portion of the oil. Then the soap is 3 extracted and the unsaponiiiable matter containing the vitamins is recovered. The methods of extraction used, no matter how carefully carried out, are ineflicient both from the point of yield and from the point of quality. In using 3 the extraction method, regardless of what solvent was used, the vitamin containing medium carried with it a dark color and an increased odor of whatever oil was used as starting material.
A further disadvantage inherent in the extraction methods heretofore used is that the solvent had to be distilled in order to recover the unsaponiflable matter. In the distillation the heat applied caused considerable damage to both vitamins A and D.
i According to the present invention it is rendered possible to increase the vitamin potency of vitamin bearing oils by almost any desired multiple. The process is carried out at moderate temperatures throughout and the harmful effects i which relatively high temperatures have upon vitamins is thereby fully avoided. In my invention the vitamins and any other active principles which may exist in the oil are automatically transferred from a portion of the oil which is i. destroyed to an unchanged portion, thereby securing the advantage of higher yields and avoiding the harmful eifects of extraction and distilling the solvents from the extracts. As a result the finely concentrated oil.is of a light pale color with little but the natural taste and odor.
An important object of the present invention is to leave unchanged a portion ofv the original vitamin bearing oil'so that this unchanged portion may be enriched and activated to substantially any desired degree with vitamins and other active principles in the original oil.
A further important object of the invention is to utilize solvents for the water soluble soaps formed and not solvents for the concentrations of vitamins which take place in the unsaponifled portions of the original oil. This permits the use of a far wider range of solvents since organic solvents may be used and even synthetic solvents which are also soluble in water and will dissolve the water soluble soaps formed.
Other and further objects of this invention will become apparent from the more detailed I description of the invention set forth below, it 5 being distinctly understood that various changes may be made therein by those skilled in the art without departing from the broad scope and spirit of the invention. Bearing in mind the broad principles outlined 1 above, I may achieve the objects of this invention in various different ways. In one method I can break up a portion of the glycerides which compose the oil by means of an alkali, conveniently sodium or potassium hydroxide, although any alkali which will form water soluble soaps with the glycerides may be used. The unsaponiflable matter including the vitamins which was associated with these glycerides will now become associated with the unchanged portion of the oil. This oil is then separated from the snaps formed by dissolving the mixture in a suflicient quantity of aqueous alcohol or other mixtures capable of dissolving the soap.
In general the solvent used may be any organic solvent or solvents which in conjunction with each other or with water have the power of dissolving the water soluble soaps so as to form solutions of relatively low viscosity. These solvent mixtures will dissolve the acid soaps present as well as the neutral soaps and permit the globules of oil to rise to the surface of the quiescent mixture and coalesce as a clear layer of oil. The utilization of a centrifuge on the mixture im-' proves the efllciency of the process and the clarity of the oil.
A second method of effecting the objects of my invention may be carried out as follows. A quantity of oil is continuously agitated with a solution of an alkali which will form water soluble 40 soaps in aqueous alcohol or any of the soap solvent mixtures mentioned above until all interaction between the oil and alkali has ceased. At such time a portion of the glycerides which compose the oil will have been saponified. At this point the mixture will show an acid reaction to phenolphthalein dissolved in ethyl alcohol. The quantity of alkali used, it must be remembered, is less than that necessary to completely saponify the oil. The actual amount of the alkali used .will depend upon the degree to which it is desired to concentrate the oil. The amount of alkali used therefore affords the operator a conv trol over the concentration of vitamins desired in the final oil. II
- ber of 159.9 and 186.9 respectively, will give a' layer washed with a portion of the solvent mixture previously used and then with a dilute mineral acid to break up any remaining traces of soap. The process may be hastened and somewhat higher recovery realized by using a centrifuge to separate the oil. The amount and concentration of the solvent mixture used will depend upon the kind of solvent or solvents and upon the kind of alkali used, the limiting conditions being that the resulting soap solution must be clear and sufliciently fluid to allow the oil to separate therefrom.
By the methods above set forth I find it possible to increase the potency of vitamin bearing oils by about 800% or more. Furthermore, crude oils having a high acid content, dark color and disagreeable odor can be used and the resulting product will be low in acid content, light in color and have very little odor. The physical and chemical constants of the oil except for the content of unsaponifiable matter is but little altered during the process if proper precautions are .taken. For example a crude 011 containing Vitamin concentrated product containing but 0.19% free fatty acids calculated to oleic acid, and having a specific gravity of .9211 at 25 C. and an iodine number (Hanus) and saponification number of 155.0 and 187.0 respectively. The percentage of unsaponifiable matter will increase practically in direct proportion to the fraction of the oil saponified.
Example I.Cod liver oil may be used as the vitamin bearing oil, it being well known that this oil is rich in the fat-soluble vitamins known as A and "D. For breaking up the desired proportion of the glycerides I prefer to use sodium hydroxide solution having a gravity of about 35 B., although the strength of the alkali may be rather widely varied and any alkali which forms water soluble soaps may be used.
To a given quantity of theoil is added an amount of this alkali solution necessary to saponify a predetermined portion of the oil. The alkali is added very slowly while the reaction mixture is kept moderately agitated. Both the alkali and the oil are preferably at ordinary room temperature. After the mixture becomes thick enough so that there can be no settling, the agitat'ion is discontinued and the mixture allowed to stand until it shows an acid reaction to phenolphthalein when dissolved in ethyl alcohol. A period of twenty-four hours is usually 'sufficient. Water and methanol are then added until there .are present for each pound of caustic added 1 gallons of water and onegallon of methanol. The mixture is heated to about 40 C. and agitated moderately until the soap is all dissolved. The mixture is then allowed to remain quiet until the oil has separated on top, or run through a centrifugal machine to separate the oil.
Example II .A quantity of cod liver oil is continuously agitated with a solution of potassium hydroxidein aqueous ethyl alcohol until the mixture shows an acid reaction to phenolphthalein in ethyl alcohol. The quantity of potassium hydroxide used must be less than that necessary to completely saponify the oil. The alcohol-water mixture used may suitably contain about 30% by volume of ethanol, of which about fifteen parts by weight should be used for each part of potassium hydroxide. After the reaction is complete 5 the mixture is allowed to remain quiet until the unchanged oil has separated on top of the main body of the soap solution in the form of a thick emulsion. The bottom soap layer is then drawn off and the oil washed first with a quantity 10 of 30% ethanol solution, then with a dilute mineral acid to break up any remaining soap, and finally with water until the. washings are no longer acid.
Example IlI.-A quantity of cod liver oil is continuously agitated at 50-55 C. with a solution of potassium hydroxide in a carbitol-water mixture until the mixture shows an acid reaction to phenolphthalein in ethyl alcohol. The mixture is then allowed to stand until the oil 20 has separated on top in the form of a thick emulsion. The bottom soap layer is then drawn off and the oil washed first with water, then with dilute mineral acid, and finally with water until the washings are no longer acid. 25
The quantity of potassium hydroxide used depends upon the extent to which it is desired to concentrate the oil, but must be less than the amount necessary to completely saponify the oil used. The carbitol-water mixture may suit- 30 ably contain about 30% by volume of carbitol, of which about seventeen parts by weight should be used for each part of potassium hydroxide.
Example I V.--A quantity of cod liver oil is continuously agitated at 50-55 C. with a quantity 3 of potassium hydroxide dissolved in a mixture of diacetone and water until the mixture shows an acid reaction to phenolphthalein when dissolved in alcohol. The quantity of potassium hydroxide used must be less than the amount neces- 40 sary to completely saponify the oil. The solvent solution may consist of about 4 parts by weight of diacetone and about 10 parts by weight of water for each part of potassium hydroxide used.
After the reaction is complete the mixture is :5 allowed to stand until the oil has separated on top in the form of a concentrated emulsion. The bottom soap layer is then drawn off and the oil layer washed first with water, then with dilute mineral acid, and finally with water until the 50 washings are no longer acid. The oil is then steamed in vacuo to remove any remaining odor of the diacetone.
Example V.--A quantity of cod liver oil is continuously agitated at 50-60 C. with a quan- 5 tiiy of potassium hydroxide dissolved in a mixture of diethylene glycol and water until the mixture shows an acid reaction to phenolphthalein dissolved in ethyl alcohol. The quantity of potassium hydroxide must be less than the 0) amount necessary to completely saponify the oil. The solvent solution may be a mixture consisting of 30% by volume of diethylene glycol and 70% by volume of water, of which about 17 parts by weight should be used for each part of potassium hydroxide.
After the reaction-is complete the mixture is allowed to stand until the oil has separated on top in the form of a thick emulsion. The bottom soap layer is then drawn off and the oil washed first with water, then with dilute acid, and again with water until the washings are no longer acid.
Example VI.-A quantity oi cod liver oil is continuously agitated at 50-60 C. with a mixture of potassium hydroxide, water and butyl cellosolve until the mixture shows an acid reaction to phenolphthalein in ethyl alcohol. The quantity of potassium hydroxide must be less than the amount necessary to completely saponify the oil. The amount of solvents used should be about 3 parts by weight of butyl cellusolve and 12 parts by weight of water to each part of potassium hydroxide.
After the reaction is complete the mixture is allowed to stand until the oil has separated on top in the form of a thick emulsion. The bottom layer of soap is then drawn oil and the oil layer washed first with water, then with dilute acid and again several times with water. The oil is then steamed in vacuo to remove any remaining odor of the butyl cellosolve.
In my use of cellosolve mixtures I may use either ethyl cellosolve or methyl ceilosolve, each being a satisfactory solvent of the organic class I have described above.
Aseadditional alkalies may be mentioned sodium carbonate and potassium carbonate. The following may also be used as solvents for the soaps formed: ethylene glycol, acetone, propanol (normal propyl alcohol), isopropanol (iso propyl alcohol) butanol (normal butyl alcohol), iso butanol (iso butyl alcohol) and butyl carbitol.
The above detailed description sets forth the invention in its preferred practical form, but it is to be understood that the invention is fully commensurate with the appended claims.
l. The process of making a predetermined concentrated vitamin oil from a vitamin containing oil which comprises saponifying a portion of the saponiflable portion of said vitamin containing oil with an alkali hydroxide, then dissolving the acid soaps and neutral soaps formed in aqueous alcohol whereby the unsaponifled and unsaponiflable portion containing the concentrated vitamins and active principles is released from said saponified portion so that a separation may take place and then separating the saponifled portion from the unsaponifled and unsaponiflable portion.
2. The process of making a predetermined concentrated vitamin oil from a vitamin containing 011 which comprises saponifying a portion of the saponiflable portion of said vitamin containing oil with an alkali hydroxide, then dissolving the acid soaps and neutral soaps formed in a solvent whereby the unsaponifled and unsaponiiiable portioncontaining the concentrated vitamins and active principles is released from said saponifled portion so that a separation may take place and then separating the saponifled portion from the unsaponifled and unsaponiflable portion.
3. The process of making a predetermined concentrated vitamin oil from a vitamin containing oil which comprises saponifying a portion of the sapqniflable.-portion,-.,of said..vitamin containing oil with a solution of sodium hydroxide, then dissolving the acid soaps and neutral soaps formed in a solvent whereby the unsaponifled and unsaponiilable portion containing the concentrated vitamins and active principles is released from said saponifled portion so that a separation may take place and then separating the saponifled portion from the unsaponifled and unsaponiflable portion.
4. The process of making a predetermined concentrated vitamin oil from a vitamin containing oil which comprises adding an alkali slowly to the said vitamin containing 011, said alkali being of a predetermined amount .so as to saponiiy only a predetermined portion of the saponifiable portion of said vitamin containing 011, then agitating said mixture, said reaction being carried out at normal room temperature, then dissolving the acid soaps and neutral soaps formed in a solvent 5 whereby the unsaponifled and unsaponifiable portion containing the concentrated vitamins and active principles is released from said saponifled portion so that.a separation may take place and then separating the saponifled portion from the unsaponified and'unsaponifiable portion.
5. The process of making a predetermined concentrated vitamin oil from a vitamin containing oil which comprises saponifying a calculated portion of the saponifiable portion of the vitamin containing oil with alkali hydroxide, then adding aqueous alcohol to dissolve the soaps formed whereby the unsaponifled and unsaponiflable portion containing the concentrated vitamins and active principles is released from said saponifled portion so that a separation may take place, heating the mixture to about 40 C. and slowly agitating the same.
6. The process of making a predetermined concentrated vitamin oil from a vitamin containing so that a partition may take place and then separating the unsaponitled and unsaponiiiable portion containing the concentrated vitamins and active principles from the saponiiied portion.
7. The process of making a predetermined concentrated vitamin oil from a vitamin containing oil which comprises saponiiying a portion of the saponiflable portion of said vitamin containing oil with an alkali hydroxide, then dissolving the acid soaps and neutral soaps formed in a solvent whereby the unsaponiiied and unsaponiflable portion containing the concentrated vitamins and active principles is released from said saponiiled portion so that a partition may take place, then drawing ofl the'lower layer of soap solution, then washing the oil layer with aqueous alcohol and then washing the oil layer with a dilute'acid.
8. A new vitamin concentrated oil derived from a vitamin containing oil having a light pale color, slight odor and having a low content of saponiiiable matter as secured from the process set forth in claim 2.
9. The process of making a predetermined concentrated vitamin oil from a vitamin. containing oil which comprises saponifying a portion of the saponifiable portion of said vitamin containing 6 oil with an alkali hydroxide and then dissolving the acid soaps and neutral soaps formed in a solution of diethylene glycol whereby the unsaponified and unsaponiflable portion containing the concentrated vitamins and active principles is released from said saponifled portion so that a separation may take place and then separating the saponified portion from the unsaponifled and unsaponiflable portion.
10. The process of making a predetermined concentrated vitamin oil from a vitamin containing oil which comprises saponifying a portion of the saponiflable portion of said vitamin containing oil with an alkali hydroxide and then dissolving the acid soaps and neutral soaps formed in a solution of diacetone whereby the unsaponified and unsaponiflable portion containing the concentrated vitamins and active principles is released from said saponiiied portion so that a separation may take place and then separating the saponified portion from the unsaponified and unsaponifiable portion.
11. The process of making a predetermined concentrated vitamin oil from a vitamin contain-- ing oil which comprises saponifying a. portion of the sapom'flable portion of said vitamin containing oil with an alkali hydroxide and then dissolving the acid soaps and neutral soaps formed in a solvent whereby the unsaponified and unsaponifiable portion containing the concentrated vitamins and active principles is released from said saponiiied portion so that a separation may take place.
HORATIO PORTER LOOMIS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US663425A US2026395A (en) | 1933-03-29 | 1933-03-29 | Process for increasing the vitamin content of vitamin bearing oils |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US663425A US2026395A (en) | 1933-03-29 | 1933-03-29 | Process for increasing the vitamin content of vitamin bearing oils |
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| Publication Number | Publication Date |
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| US2026395A true US2026395A (en) | 1935-12-31 |
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| US663425A Expired - Lifetime US2026395A (en) | 1933-03-29 | 1933-03-29 | Process for increasing the vitamin content of vitamin bearing oils |
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1933
- 1933-03-29 US US663425A patent/US2026395A/en not_active Expired - Lifetime
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