US2309273A - Making deting oils - Google Patents
Making deting oils Download PDFInfo
- Publication number
- US2309273A US2309273A US2309273DA US2309273A US 2309273 A US2309273 A US 2309273A US 2309273D A US2309273D A US 2309273DA US 2309273 A US2309273 A US 2309273A
- Authority
- US
- United States
- Prior art keywords
- oil
- drying
- making
- oils
- pyrosulphate
- 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
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- 239000003921 oil Substances 0.000 title description 40
- 238000001035 drying Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000004359 castor oil Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- KAQHZJVQFBJKCK-UHFFFAOYSA-L potassium pyrosulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OS([O-])(=O)=O KAQHZJVQFBJKCK-UHFFFAOYSA-L 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F5/00—Obtaining drying-oils
- C09F5/06—Obtaining drying-oils by dehydration of hydroxylated fatty acids or oils
Definitions
- the presentinvention relates to the manufacture of drying oils from glyceride oils having one or more hydroxyl groups in the fatty acid radiheating at a temperature of say 300 C. into an unsaturated acid with two double bonds in a conjugated neighbouring position and thereafter esterifying the acid thus obtained with a suitable alcohol.
- Alkali metal pyrosulphate such as the sodium and potassium
- the said substances are solids that do not melt or liquefy during ordinary running of the process, they can accordingly be easily and readily and completely removed from the oil after the heating operation, they can be employed without causing undesirable darkening of the oil under treatment, they are cheap and can be produced easily and cheaply and from materials that are readily available everywhere (e. g. alkali metal bisulphate including alter-cake or alkali metal sulphate or many other commonly found alkali metal salts and sulphuric acid), and the drying oils produced may have a desirably low acid number.
- Example First part.-Castor oil is stirred with 1% by weight of finely divided potassium pyrosulphate, and heated under vacuum whilst passing carbon dioxide through the liquid at a temperature from 180-240 C. for 4 hours. The temperature is slowly raised during the heating process until the distillation of water has ceased.
- Second port-The mixture may then be further heated for 3 hours at a temperature of 280 C. under the same working conditions in order to form a stand 011.
- a high grade drying oil product is obtained with valuable technical properties.
- the product of the first part" of the process (if filtered from the pyrosulphate) is a drying oil, light in color, of strong drying properties and with an acid number very little above that of the castor oil employed as starting material.
- oils which are esters of hydroxy fatty acids can be treated by this process to produce drying oils, e. g. ,thetriglyceride of dihydroxystearic .acid. a
- a small percentage of the pyrosulphate is sufiicient, e. g. from 0.1% to 5% may be employed, but preferably 0.2% to 1.5% is most satisfactory.
- the potassium salt the sodium salt, or mixture of the sodium and potassium salts are also suitable;
- temperatures given in the example are suitable and satisfactory, but various temperatures in the first part of the process substantially over C. and up to 260 C. may be used. In the second part of the process, temperatures over 260 0., up to 300 (2., may be used. It is hardly necessary to state that the higher temperatures, especially it continued for a long time,
- time element given in the example is satisfactory. But, with somewhat higher temperatures, correspondingly shorter time periods can be used.
- the carbon dioxide can be replaced by other ity, and usable-for all the common uses of drying oils.
- the drying oil produced by the present process has excellent drying properties, similar to those of Chinese tung oil, and shows a very fine light yellow color. With driers added, a film of the oil dries rapidly, to a strong film.
- a stand oil can be produced from these drying oils, e. g. as in the second part of the above example.
- the temperature for the formation may be 260-300 C., preferably 270 to 280 C.
- a process of making a drying oil which comprises heating a glyceride oil which is an ester of'a hydroxy fatty acid, in the presence of a small amount of a pyrosulphateas a dehydrating catalyst, to a temperature substantially above 150 C., for a sufficient time to cause splitting off of water from the hydroxyl groups of the hydroxy fatty acid radical, and continuing the heating until substantial drying properties are developed in the oil, the pyrosulphate being one that is a solid and which remains solid throughout the process.
- a process of making a drying oil which comprises heating castor oil with not more than a few percent of an alkali metal pyrosulphate, to over C., until an oil having drying properties is produced.
- a process of making a drying oil which comprises heating castor oil with not more than a few percent of an alkali metal pyrosulphate, to substantially over 150 C., while passing a current of an inert gas through said oil, until an oil having drying properties is produced.
- a process of making a drying oil which comprises heating castor oil with not more than a few percent of an alkali metal pyrosulphate, to substantiallyover 150 C., while the oil is under a pressure substantially below atmospheric, until an oil having drying properties is produced. 7
- a process of making a drying oil which comprises heating castor oil mixed with not more than a few percent of pyrosulphate of an alkali metal, to about to 240 C., for about 4 hours, while said oil is under vacuum and while passing a current of an inert gas through said oil.
- a process of making a drying oil which comprises heating castor oil mixed with not more than a few percent of a pyrosulphate of an alkali metal, to about 180 to 240 C., for about 4 hours, while said oil is under vacuum and while passing a current of an inert gas through said oil, and thereafter heating the said material to about 270 to 300 C., until thickening to stand oil consistency is effected.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
Description
Patented Jan. 26, 1943 MAKING DRYING OILS Remmet Priester, Deventer, Netherlands; vested in the Alien Property Custodian No Drawing. Application October 24, 1940, Serial In the Netherlands January 6,
6 Claims. (Cl. 260-398) The presentinvention relates to the manufacture of drying oils from glyceride oils having one or more hydroxyl groups in the fatty acid radiheating at a temperature of say 300 C. into an unsaturated acid with two double bonds in a conjugated neighbouring position and thereafter esterifying the acid thus obtained with a suitable alcohol. 1
For obviousreasons, a process which causes the splitting off of water from the -hydroxyl groups of the hydroxy fatty acid radicals present in the castor or like oil, without causing liberation of any considerable amount of free acid from the glyceride oil, is advantageous. Such a reaction has heretofore been suggested, using sulphuric acid or certain other substances as the catalyst. Among the very satisfactory catalysts originally described in my earlier cases (including Ser. No. 181,467 filed Dec. 23, 1937, of which the present case is in major part 'a continuation and which has now matured into Patent 2,226,830,) may be mentioned pyrosulphate such as K2820: potassium pyrosulpl'iate.
Alkali metal pyrosulphate, such as the sodium and potassium, are very useful, and possess important advantages over many of the catalysts proposed in the prior art, particularly in that the said substances are solids that do not melt or liquefy during ordinary running of the process, they can accordingly be easily and readily and completely removed from the oil after the heating operation, they can be employed without causing undesirable darkening of the oil under treatment, they are cheap and can be produced easily and cheaply and from materials that are readily available everywhere (e. g. alkali metal bisulphate including alter-cake or alkali metal sulphate or many other commonly found alkali metal salts and sulphuric acid), and the drying oils produced may have a desirably low acid number.
Formore compleuely describing the process, I givle the following specific example, from Ser. No. 18 .487: a j
Example First part.-Castor oil is stirred with 1% by weight of finely divided potassium pyrosulphate, and heated under vacuum whilst passing carbon dioxide through the liquid at a temperature from 180-240 C. for 4 hours. The temperature is slowly raised during the heating process until the distillation of water has ceased.
Second port-The mixture may then be further heated for 3 hours at a temperature of 280 C. under the same working conditions in order to form a stand 011. After elimination of the catalyst in the usual way (e. g. by filtration or straining) a high grade drying oil product is obtained with valuable technical properties.
The product of the first part" of the process (if filtered from the pyrosulphate) is a drying oil, light in color, of strong drying properties and with an acid number very little above that of the castor oil employed as starting material.
Instead of castor 011, other oils which are esters of hydroxy fatty acids can be treated by this process to produce drying oils, e. g. ,thetriglyceride of dihydroxystearic .acid. a
It will be understood that a small percentage of the pyrosulphate is sufiicient, e. g. from 0.1% to 5% may be employed, but preferably 0.2% to 1.5% is most satisfactory. Instead of the potassium salt, the sodium salt, or mixture of the sodium and potassium salts are also suitable;
The temperatures given in the example are suitable and satisfactory, but various temperatures in the first part of the process substantially over C. and up to 260 C. may be used. In the second part of the process, temperatures over 260 0., up to 300 (2., may be used. It is hardly necessary to state that the higher temperatures, especially it continued for a long time,
may cause a higher acidity of the oil.
The time element given in the example is satisfactory. But, with somewhat higher temperatures, correspondingly shorter time periods can be used.
The carbon dioxide can be replaced by other ity, and usable-for all the common uses of drying oils.
As set forth in my copending case 181,468 filed December 23, 1937 (now Patent 2,226,831), there may be a substantial rise in acid number in the oil, during the second part of the process, and this can be prevented by adding glycerol to the oil, before or during or after the first part of the process, and before the second part of the'process. The amount of such glycerol may be about 1% or from 0.5 to 3%, more or less. Other not easily volatile active alcohols can be similarly used, e. g. sorbitol, cetyl alcohol, glycol, pentaerythritol, r alkylene oxides such as ethylene oxide can be introduced into the oil, e. g. with the current of inert gas, during the second part of the process.
The drying oil produced by the present process has excellent drying properties, similar to those of Chinese tung oil, and shows a very fine light yellow color. With driers added, a film of the oil dries rapidly, to a strong film. A stand oil can be produced from these drying oils, e. g. as in the second part of the above example. The temperature for the formation may be 260-300 C., preferably 270 to 280 C.
I claim:
1. A process of making a drying oil which comprises heating a glyceride oil which is an ester of'a hydroxy fatty acid, in the presence of a small amount of a pyrosulphateas a dehydrating catalyst, to a temperature substantially above 150 C., for a sufficient time to cause splitting off of water from the hydroxyl groups of the hydroxy fatty acid radical, and continuing the heating until substantial drying properties are developed in the oil, the pyrosulphate being one that is a solid and which remains solid throughout the process.
2. A process of making a drying oil which comprises heating castor oil with not more than a few percent of an alkali metal pyrosulphate, to over C., until an oil having drying properties is produced.
3. A process of making a drying oil which comprises heating castor oil with not more than a few percent of an alkali metal pyrosulphate, to substantially over 150 C., while passing a current of an inert gas through said oil, until an oil having drying properties is produced.
4. A process of making a drying oil which comprises heating castor oil with not more than a few percent of an alkali metal pyrosulphate, to substantiallyover 150 C., while the oil is under a pressure substantially below atmospheric, until an oil having drying properties is produced. 7
5. A process of making a drying oil which comprises heating castor oil mixed with not more than a few percent of pyrosulphate of an alkali metal, to about to 240 C., for about 4 hours, while said oil is under vacuum and while passing a current of an inert gas through said oil.
6. A process of making a drying oil which comprises heating castor oil mixed with not more than a few percent of a pyrosulphate of an alkali metal, to about 180 to 240 C., for about 4 hours, while said oil is under vacuum and while passing a current of an inert gas through said oil, and thereafter heating the said material to about 270 to 300 C., until thickening to stand oil consistency is effected.
REMMET PRIESTER.
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US2309273A true US2309273A (en) | 1943-01-26 |
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US2309273D Expired - Lifetime US2309273A (en) | Making deting oils |
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