US1867665A - Refining method of vegetable oils to be used as solvents for injection medicines - Google Patents
Refining method of vegetable oils to be used as solvents for injection medicines Download PDFInfo
- Publication number
- US1867665A US1867665A US391112A US39111229A US1867665A US 1867665 A US1867665 A US 1867665A US 391112 A US391112 A US 391112A US 39111229 A US39111229 A US 39111229A US 1867665 A US1867665 A US 1867665A
- Authority
- US
- United States
- Prior art keywords
- oil
- vegetable oils
- solvents
- refining method
- free fatty
- 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
- 239000002904 solvent Substances 0.000 title description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 title description 7
- 239000008158 vegetable oil Substances 0.000 title description 7
- 239000003814 drug Substances 0.000 title description 5
- 238000002347 injection Methods 0.000 title description 5
- 239000007924 injection Substances 0.000 title description 5
- 238000000034 method Methods 0.000 title description 5
- 238000007670 refining Methods 0.000 title description 5
- 229940079593 drug Drugs 0.000 title 1
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 19
- 235000021588 free fatty acids Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- -1 aromatic alcohols Chemical class 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000010999 medical injection Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 230000001131 transforming effect Effects 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
Classifications
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/06—Refining fats or fatty oils by chemical reaction with bases
Definitions
- This invention relates to a refining method of vegetable oils'to be used for medical purposes. It comprises removing glycerine and free fatty acids, the productsof oil by decomposition, contained in the oil to be refined, and transforming free fatty acid which possibly remain in trace in the treated oil into an ester with aromatic alcohol.
- the object of this invention is to obtain a neutral 1 solvent for oil-soluble substances to be used for hypodermicor muscular injection, which is never followed by irritation or pain. 7
- Olive oil for example, which has been used hitherto as a solvent of oil-soluble injecting medicine, such as camphor, has its acidity from 2 to 8 and its exponent'of hydrogen-ion is from 2 to 4. It apparently contains glycerine and free fatty acid which have been produced by decomposition of oil.
- the ex-' ponent of hydrogen-ion of human blood being 7, the large difference of the number between olive oil and human blood as well as the presence of free fatty acid in the oil gives intolerable pain and the injected part often suppurates, if the injected medicine is dissolved in olive oil.
- glycerine and free fatty acids contained in vegetable oil are at first removed as completely-- as possible, and a trace of free fatty acid that cannot be removed anyhow, is neutralized by transforming same into an ester with aromatic alcohol.
- the acidi't of the treated oil becomes perfectly nil and its e 011%113 n account'of these facts, if the oil refined in this way is used as a solvent of an injection medicine, the unfavorable effects above mentioned can be successfully avoided.
- aromatic alcohols only are used to transform free fatty acid into an ester thereof. This is because:
- the mixture is shaken so as to make a homo-' geneous milky liquid. After it is maintained about half an hour at a temperature of from 50 to 60 C. it is poured into a separating funnel, Where the mixture sep- 4 -aratesin 3 to 4 hours into two layers oil and milky mixture of the refined oil with diswater, whereupon the water layer is re- 'moved. This washing operation shouldbe repeated several times till the removed Water becomes non-acidic. In order to remove the water which closely mixes with the oil, red heated table salt of about 50 grams or other harmless dehydrating agent which is not soluble in oil is thrown in the oil, and the latter is filtered when it becomes transparent.
- the concentration number of hydrogen-ion in the tilled water is 6.3 at the largest, and this number can never be increased how many times the washing operation is repeated.
- a refining method of vegetable oils to be used as solvents for medical injection which comprises removing the greater-portion of glycerine and free fatty acid contained in the oil, and transformlng free fatty .acid
- a refining method of vegetable oils to be used as solventsfor medical injection which comprises repeatedly washing the oil with water until the washed-Water is non-acidic, and adding thereto benzyl alcohol and heating same so as to make free fatty acid in the oil esterified.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
Description
35- of hydrogen-ion increases closely to Patented July 19, 1932 UNITED STATES PATENT OFFICE HEISAKU EATAKEYAMLA AND HOTORI WATANABE, O F KOBE, JAPAN BEE'INING METHOD OF ,VEGETABLE OILS TO BE USED AS SOLVENTS FOR INJECTION MEDICINES No Drawing. Application filed September 7, 1929, Serial No. 391,112, and in Japan September 12, 1928.
This inventionrelates to a refining method of vegetable oils'to be used for medical purposes. It comprises removing glycerine and free fatty acids, the productsof oil by decomposition, contained in the oil to be refined, and transforming free fatty acid which possibly remain in trace in the treated oil into an ester with aromatic alcohol. The object of this invention is to obtain a neutral 1 solvent for oil-soluble substances to be used for hypodermicor muscular injection, which is never followed by irritation or pain. 7
Olive oil, for example, which has been used hitherto as a solvent of oil-soluble injecting medicine, such as camphor, has its acidity from 2 to 8 and its exponent'of hydrogen-ion is from 2 to 4. It apparently contains glycerine and free fatty acid which have been produced by decomposition of oil. The ex-' ponent of hydrogen-ion of human blood being 7, the large difference of the number between olive oil and human blood as well as the presence of free fatty acid in the oil gives intolerable pain and the injected part often suppurates, if the injected medicine is dissolved in olive oil.
According to this invention, glycerine and free fatty acids contained in vegetable oil are at first removed as completely-- as possible, and a trace of free fatty acid that cannot be removed anyhow, is neutralized by transforming same into an ester with aromatic alcohol. In this way, the acidi't of the treated oil becomes perfectly nil and its e 011%113 n account'of these facts, if the oil refined in this way is used as a solvent of an injection medicine, the unfavorable effects above mentioned can be successfully avoided.
In this invention aromatic alcohols only are used to transform free fatty acid into an ester thereof. This is because:
1. Aromatic alcohols are esterified with free fatty acids easier than fatty, alcohols.
For example, olein acid and benzyl alcohol are easily esterified when they are slightly heated, while theacid and fatty alcohol are scarcely esterified without using a catalyzer or a dehydrating agent as sulphuric acid or high pressure.
2. The ester made from an aromatic alco- 1101 and a high grade fatty acid has local narcotic effect'to human body, and when it ais absorbed into human body it is .easily oxidized and the excess of aromatic alcohol, if
any, changes into harmless hippuric acid and is excreted. Contrary to this, the fatty acids with low molecular weight, such as ethyl or methyl alcohol, gives a great pain i fication those which have OH group in sidechain of benzene ring, for example, benzyl alcohol .Oomon phenyl ethyl alcohol Oom- 011,011,
cinnamic alcohol oxybenzyl alcohol omon which has OH groups in benzene ring as well as .in side chain, and other oxyaromatic a1- cohols. These alcohols can be used in this invention, but mono and poly phenols with one or more OH groups in benzene ring should not be used, because these phenols have irrita-' tive and destructive effects to physical tissue.
This invention is further described referring to an example.
The vegetable oil to be treated should be decolored at first if itis colored one. Such decoloration can be easily attained by heat- 1 v ing the oil to'which a suitable quantity of acidic white clay and animal charcoal have been added.- Two liters of such decolored oil is taken in a flask and is heated on water bath, to which is added 300 c. c. of distilled water at atemperature of about 100 C., and
the mixture is shaken so as to make a homo-' geneous milky liquid. After it is maintained about half an hour at a temperature of from 50 to 60 C. it is poured into a separating funnel, Where the mixture sep- 4 -aratesin 3 to 4 hours into two layers oil and milky mixture of the refined oil with diswater, whereupon the water layer is re- 'moved. This washing operation shouldbe repeated several times till the removed Water becomes non-acidic. In order to remove the water which closely mixes with the oil, red heated table salt of about 50 grams or other harmless dehydrating agent which is not soluble in oil is thrown in the oil, and the latter is filtered when it becomes transparent.
In spite of such a refining treatment, the concentration number of hydrogen-ion in the tilled water is 6.3 at the largest, and this number can never be increased how many times the washing operation is repeated.
This means that a trace of free fatty acid still remains in the oil. Then 3% in volume of benzyl alcohol is addedto the oil and is heated on water bath at a temperature of about 60 C. to C. in order to esterify the free fatty acid. In order to remove the water produced due to esterification carbondioxide which has been dried by passing through sulphuric acid is bubbled in the oil. When the water is removed, the oil is heated under reduced pressure in order to remove excess benzyl alcohol which may remain in the o1 non-acidic, and the injection in which the oil is used as its solvent gives no pain at all, and there is no possibility of harming the injected part of the human body.
Claims:
1. A refining method of vegetable oils to be used as solvents for medical injection, which comprises removing the greater-portion of glycerine and free fatty acid contained in the oil, and transformlng free fatty .acid
which remain in trace in the oil into an ester by combination with an aromatic alcohol.
2. A refining method of vegetable oils to be used as solventsfor medical injection, which comprises repeatedly washing the oil with water until the washed-Water is non-acidic, and adding thereto benzyl alcohol and heating same so as to make free fatty acid in the oil esterified.
HEISAKU HATAKEYAMA. HOTORI WATANABE.
The refined oil thus obtained is perfectly
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1867665X | 1928-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1867665A true US1867665A (en) | 1932-07-19 |
Family
ID=16194253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US391112A Expired - Lifetime US1867665A (en) | 1928-09-12 | 1929-09-07 | Refining method of vegetable oils to be used as solvents for injection medicines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1867665A (en) |
-
1929
- 1929-09-07 US US391112A patent/US1867665A/en not_active Expired - Lifetime
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