US2525892A - Refining tall oil - Google Patents
Refining tall oil Download PDFInfo
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- US2525892A US2525892A US734232A US73423247A US2525892A US 2525892 A US2525892 A US 2525892A US 734232 A US734232 A US 734232A US 73423247 A US73423247 A US 73423247A US 2525892 A US2525892 A US 2525892A
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- Prior art keywords
- tall oil
- acid
- oil
- mixture
- resin
- 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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- 239000003784 tall oil Substances 0.000 title claims description 49
- 238000007670 refining Methods 0.000 title description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Chemical class 0.000 claims description 19
- 235000011007 phosphoric acid Nutrition 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 235000019645 odor Nutrition 0.000 description 12
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000011347 resin Chemical class 0.000 description 9
- 229920005989 resin Chemical class 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 238000007664 blowing Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000470 constituent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229940046892 lead acetate Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940065278 sulfur compound Drugs 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229940056932 lead sulfide Drugs 0.000 description 1
- 229910052981 lead sulfide Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000002966 varnish 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; DRIERS (SICCATIVES); TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
Definitions
- This invention relates to a process of refining tall oil.
- it relates to a process for producing tall oil having a high fatty acid content and having no objectionable odor.
- tall oil obtained as a by-product in the sulfate and soda pulping process, is an inexpensive source of fatty acids and resin acids its use in industry has been limited because of the oflensive odors associated with it, and because it exists as a mixture dimcult to separate into its constituents. It has been proposed to remove odors, reduce the tendency to crystallize, improve the color and otherwise refine tall oil by various methods such as heating, distilling with and without the aid of steam, treating with chemical agents, solvent extraction, treating with adsorbents such as fullers earth, etc., with varying degrees of success. Separation of the resin acid constituents from the fatty acid constituents is much more difilcult and requires involved treatment such as extraction with a selective.
- One object of this invention is to produce a refined tall oil. Another object is. to improve the odor of tall oil. A further object is to reduce substantially the resin acid content of tall oil to produce a fatty acid material of good commercial value.
- quantity of salt added should be such as to give a (H+) content equivalent to that obtained with from 0.1% to 0.5% of the acid.
- the temperature to which the mixture of phosphoric acid and tall oil should be heated is advancompounds is made possibleat temperatures far below those which result in pyroiytic decomposition of the tall oil.
- improvement results in that upon cooling of the treated tageously about 300 F. Good results are .obtained at temperatures in the range of about 280- 330 F. If the temperature is carried much above 350 F., there is no advantage to be gained as excessive mechanical and decomposition losses are encountered.
- Heating of the tall oil in the presence of phosphoric acid is continued until evolution of sulfides can no longer be detected by smell, reaction of the vapors on paper moistened with lead acetate solution, or other suitable means.
- the heating is preferably carried out in a vessel which is closed, except for a duct to carry our the vapors evolved, in order to exclude air and thereby prevent formation of pitch and oxidation products.
- the operation may be carried on by simply heating phosphoric acid and-tall oil to the temperature specified, the removal of the released sulfide bearing gas is facilitated by blowing a non-oxidizing as, for example carbon dioxide,
- steam may also exert some chemical, possibly hydrolytic, effect which is advantaseous. Blowing is also beneficial in that it causes the removal of some of the unsaponifiable constituents of tall oil at this point, and certain oily bodies in tall oil that are of foul odor and easily turn dark when exposed to air and/or light.
- the rate of introduction of gases is governed by the losses from the tall oil due to entrainment and distillation; such losses, preferably, should be in range of 2-5%. Because of the action of the phosphoric acid, any blowing operation in its presence is much more effective in the removal of undesirable odors than in its absence, permitting a substantial savings in heat and other costs since lower temperatures and shorter blowing times are required and less pyrolytic decomposition occurs. Also, such expedients as reduced pressure during blowing are unnecessary.
- the resin acid crystals form easily and rapidly and may be separated mechanically by filtration, centrifuging, etc. Crystals high in resin acid content, that is containing of the order of 80% to 90% of resin acids, are obtained and in amounts equal to between 25% and 30% of the weight of the tall oil. The liquid portion is correspondingly depleted of resin acid and increased in fatty acid content.
- Crude tall oil in the amount of 400 lbs., is pumped into stainless steel tank equipped with direct and indirect steam coils, and a recirculating pump. Circulation is started and 2 lbs. of phosphoric acid (85% H3PO4 content) is added directly to the charge.
- the indirect steam coil is turned on and when the temperature of the oil reaches about 220 F. the circulating pump is shut down as the direct steam (125 p. s. i.) is turned on.
- the temperature of the oil is increased to 300 F. and maintained 120 F. by means of the indirect coil for the remainder of the steam blowing.
- the vapors arising from the tank are tested periodically with strips of paper which have been dipped in a 10% solution of lead acetate.
- the treated oil is allowed to settle for about 2 hours after all heating has been terminated; hard black pitch in an amount equal to 0.5% of the original weight of the oil settles out leaving the hot oil dark red in color but clear and bright in appearance.
- the tall oil is then pumped through a cooler and delivered to a crystallizing tank and allowed to stand for two days.
- the product, practically a solidified mass, is forced out of the tank into a basket-type centrifuge by means of compressed air.
- the liquid portion of the tall oil passes from the centrifuge to a collect- Cry tal Crystals 5 Tan on Free 011 Moisture T Ash 0. 01 Unsaponiflables. 5. 37 0. 1!) Resin Acids 28. 35 83. 06 Fatty Acids (By difference 47. 66.
- tall oil is readily and cheaply freed of foul odors with simple, readily available equipment and a minimum of material and labor cost, and the resin acids of the oil are more easily removed so that a product rich in fatty acids is obtained.
- the resin acids obtained are suitable for use in varnishes, inks, papermaking size, etc., while the fatty acid-rich, sulfide-free tall oil is adapted for use in soaps, emulsifiers, plasticizers, etc.
- the steps which comprise adding to the tall oil a material from the group consisting of orthophosphoric acid and its acid salts in an amount equivalent to not more than 0.5% of orthophopsphoric acid on the weight of the tall oil, heating the mixture to a temperature not exceeding about 350-F. and passing a stream of non-oxidizing gas through the mixture.
- the step which comprises blowing steam through heated tall oil which contains a material selected from the group comprising orthophosphoric acid and its acid salts in an amount equivalent, to from 0.1% to 0.5% of orthophosphoric acid on the weight of the tall oil, the temperature of said heated tall oil not exceeding about 350 F.
- the steps which comprise adding a material from the group consisting of orthophosphoric acid and its acid salts in an amount equivalent to not more than 0.5 of orthophosphoric acid on the weight of the tall oil, heating the mixture to a temperature between 280 F. and 350 F. and passing steam through the mixture.
- Process of prcducing a refined tall oil free of objectionable odor which comprises adding from 0.1% to 0.5% of orthophosphoric acid to crude tall 011, heating' the mixture, passing steam through the mixture while it is maintained at a temperature between 280 F. and 330 F. until lead acetate paper fails to give a sulphide test after flve minutes exposure to the vapor eflluent, allowing the mixture to cool, and mechanically separating the precipitated crystals fromthe liquid portion of the mixture.
- the process of treating tall oil which comprises adding to the tall oil from 0.1% to 2 of tall oil until evolution of sulfide odors ceases, set-' tling out the insoluble materials from the hot tall oil and removing the settlings. cooling the tall oil, and separating from the tall oil the resin acid crystals which form.
Description
Patented Oct. 17, 1950 REFINING TALL OIL Louis E. Gates and Lee A. Radeker, Canton, N. 0.. assignors to The Champion Paper and Fibre gfllmpany, Hamilton, Ohio, a corporation of No Drawing. Application March 12, 1947,
Serial No. 734,232
6 Claims.
This invention relates to a process of refining tall oil. In particular it relates to a process for producing tall oil having a high fatty acid content and having no objectionable odor.
Although tall oil, obtained as a by-product in the sulfate and soda pulping process, is an inexpensive source of fatty acids and resin acids its use in industry has been limited because of the oflensive odors associated with it, and because it exists as a mixture dimcult to separate into its constituents. It has been proposed to remove odors, reduce the tendency to crystallize, improve the color and otherwise refine tall oil by various methods such as heating, distilling with and without the aid of steam, treating with chemical agents, solvent extraction, treating with adsorbents such as fullers earth, etc., with varying degrees of success. Separation of the resin acid constituents from the fatty acid constituents is much more difilcult and requires involved treatment such as extraction with a selective. solvent, fractional distillation, selective esterification, saponification, and other chemical steps, or combinations of these operations. These separation methods, even when employed in a large number of steps, do not yield a clear cut fraction of fatty acids or resin acids and are relatively expensive for the improvement gained.
One object of this invention is to produce a refined tall oil. Another object is. to improve the odor of tall oil. A further object is to reduce substantially the resin acid content of tall oil to produce a fatty acid material of good commercial value. These and other objects are attained in a relatively simple, economical manner.
We have discovered that the addition of very small amounts of orthophosphoric acid or its acid salts to tall oil followed by heating to a moderate temperature results in marked improvements in the tall oii thus treated. There are at least two definite improvements resulting from this treatment. In the first place the sulfur compounds, which are present in thetall oil in some not very well understood combination, are released much sulfuring. This release ofthe malodorous sulfur specified'is over and above the amount necessary to neutralize any soaps present in the tall oil. Larger amounts of phosphoric acid, of the order of 1% to 2%. afford some improvement over the smaller amounts, but in most cases it is not sumcient to warrant the additional cost. The acid or salt is added before 200 F. is reached and in ei-'- 2o ther case, good agitation is maintained. The
quantity of salt added should be such as to give a (H+) content equivalent to that obtained with from 0.1% to 0.5% of the acid.
The temperature to which the mixture of phosphoric acid and tall oil should be heated is advancompounds is made possibleat temperatures far below those which result in pyroiytic decomposition of the tall oil. In the second place improvement results in that upon cooling of the treated tageously about 300 F. Good results are .obtained at temperatures in the range of about 280- 330 F. If the temperature is carried much above 350 F., there is no advantage to be gained as excessive mechanical and decomposition losses are encountered.
Heating of the tall oil in the presence of phosphoric acid is continued until evolution of sulfides can no longer be detected by smell, reaction of the vapors on paper moistened with lead acetate solution, or other suitable means. The heating is preferably carried out in a vessel which is closed, except for a duct to carry our the vapors evolved, in order to exclude air and thereby prevent formation of pitch and oxidation products.
Although the operation may be carried on by simply heating phosphoric acid and-tall oil to the temperature specified, the removal of the released sulfide bearing gas is facilitated by blowing a non-oxidizing as, for example carbon dioxide,
nitrogen, etc., through the hot mixture. We have i found steam to be particularly advantageous for this purpose. It is possible that the steam. may also exert some chemical, possibly hydrolytic, effect which is advantaseous. Blowing is also beneficial in that it causes the removal of some of the unsaponifiable constituents of tall oil at this point, and certain oily bodies in tall oil that are of foul odor and easily turn dark when exposed to air and/or light.
The rate of introduction of gases is governed by the losses from the tall oil due to entrainment and distillation; such losses, preferably, should be in range of 2-5%. Because of the action of the phosphoric acid, any blowing operation in its presence is much more effective in the removal of undesirable odors than in its absence, permitting a substantial savings in heat and other costs since lower temperatures and shorter blowing times are required and less pyrolytic decomposition occurs. Also, such expedients as reduced pressure during blowing are unnecessary.
After cooling of the treated tall oil the resin acid crystals form easily and rapidly and may be separated mechanically by filtration, centrifuging, etc. Crystals high in resin acid content, that is containing of the order of 80% to 90% of resin acids, are obtained and in amounts equal to between 25% and 30% of the weight of the tall oil. The liquid portion is correspondingly depleted of resin acid and increased in fatty acid content.
It is well known that the separation of the fatty acid from the resin acid content by various distillation methods is very unsatisfactory in obtaining sharp separations. However, by using this filtered product of our process as the starting material in a fractional distillation, a greatly improved separation can be obtained because of the higher ratio of fatty acids to resin acids at the beginning of the operation. Similarly separation of the fatty acids from the resin acids by esterification or selective solvent extraction is more effective when carried out on our improved tall oil than on a crude oil.
The invention is illustrated by the following example:
Crude tall oil, in the amount of 400 lbs., is pumped into stainless steel tank equipped with direct and indirect steam coils, and a recirculating pump. Circulation is started and 2 lbs. of phosphoric acid (85% H3PO4 content) is added directly to the charge. Next the indirect steam coil is turned on and when the temperature of the oil reaches about 220 F. the circulating pump is shut down as the direct steam (125 p. s. i.) is turned on. The temperature of the oil is increased to 300 F. and maintained 120 F. by means of the indirect coil for the remainder of the steam blowing. The vapors arising from the tank are tested periodically with strips of paper which have been dipped in a 10% solution of lead acetate. When a treated strip remains in the vapors for 5 minutes with no appreciable darkening due to formation of lead sulfide all the steam is shut off. Total steaming time is approximately 6 hours. The blown oil has a pleasant, faint, caramel-like odor as compared to the original foul sulfur-compound odor.
The treated oil is allowed to settle for about 2 hours after all heating has been terminated; hard black pitch in an amount equal to 0.5% of the original weight of the oil settles out leaving the hot oil dark red in color but clear and bright in appearance. The tall oil is then pumped through a cooler and delivered to a crystallizing tank and allowed to stand for two days. The product, practically a solidified mass, is forced out of the tank into a basket-type centrifuge by means of compressed air. The liquid portion of the tall oil passes from the centrifuge to a collect- Cry tal Crystals 5 Tan on Free 011 Moisture T Ash 0. 01 Unsaponiflables. 5. 37 0. 1!) Resin Acids 28. 35 83. 06 Fatty Acids (By difference 47. 66. 27 10.63 Acid N o. 169 161 Baponiflcation N o. 177 177 180 The process makes it possible to obtain high yields of resin acids without resorting to the use of refrigeration or other expensive equipment and procedures. Resin acid crystals in the amount of 10% to 15% by weight can be separated from crude tall oil upon prolonged standing, whereas phosphoric acid treated tall oil yields 25% to 30% of resin acid crystals on the weight of the oil.
By the process of this invention tall oil is readily and cheaply freed of foul odors with simple, readily available equipment and a minimum of material and labor cost, and the resin acids of the oil are more easily removed so that a product rich in fatty acids is obtained. The resin acids obtained are suitable for use in varnishes, inks, papermaking size, etc., while the fatty acid-rich, sulfide-free tall oil is adapted for use in soaps, emulsifiers, plasticizers, etc.
We claim:
1. In the process of refining tall oil the steps which comprise adding to the tall oil a material from the group consisting of orthophosphoric acid and its acid salts in an amount equivalent to not more than 0.5% of orthophopsphoric acid on the weight of the tall oil, heating the mixture to a temperature not exceeding about 350-F. and passing a stream of non-oxidizing gas through the mixture.
2. In the process of purifying tall oil, the step which comprises blowing steam through heated tall oil which contains a material selected from the group comprising orthophosphoric acid and its acid salts in an amount equivalent, to from 0.1% to 0.5% of orthophosphoric acid on the weight of the tall oil, the temperature of said heated tall oil not exceeding about 350 F.
3. In the process of purifying tall oil, the steps which comprise adding a material from the group consisting of orthophosphoric acid and its acid salts in an amount equivalent to not more than 0.5 of orthophosphoric acid on the weight of the tall oil, heating the mixture to a temperature between 280 F. and 350 F. and passing steam through the mixture.
4. The process of treating tall oil which comprises adding to the tall oil orthophosphoric acid in an amount equal to between 0.1% to 2% on the tall oil, heating the mixture to temperature between 280 F. and 330 F., passing steam through the mixture until there is no further evolution of sulphide odors, cooling the mixture, and mechanically separating the crystals which form.
5. Process of prcducing a refined tall oil free of objectionable odor which comprises adding from 0.1% to 0.5% of orthophosphoric acid to crude tall 011, heating' the mixture, passing steam through the mixture while it is maintained at a temperature between 280 F. and 330 F. until lead acetate paper fails to give a sulphide test after flve minutes exposure to the vapor eflluent, allowing the mixture to cool, and mechanically separating the precipitated crystals fromthe liquid portion of the mixture.
6. The process of treating tall oil which comprises adding to the tall oil from 0.1% to 2 of tall oil until evolution of sulfide odors ceases, set-' tling out the insoluble materials from the hot tall oil and removing the settlings. cooling the tall oil, and separating from the tall oil the resin acid crystals which form.
LOUIS E. GATES. LEE A. RADEER.
REFERENCES CITED The following references are of record in the tile 0! this patent:
' UNITED STATES PATENTS 2,441,198 Babayan May 11, 1948
Claims (1)
1. IN THE PROCESS OF REGINING TALL OIL THE STEPS WHICH COMPRISE ADDING TO THE TALL OIL A MATERIAL FROM THE GROUP CONSSITING OF ORTHOPHOSPHORIC ACID AND ITS ACID SALTS IN AN AMOUNT EQUIVALENT TO NOT MORE THAN 0.5% OF ORTHOPHOPSPHORIC ACID ON THE WEIGHT OF THE TALL OIL, HEATING THE MIXTURE TO A TEMPERATURE NOT EXCEEDING ABOUT 350*F. AND PASSING A STREAM OF NON-OXIDIZING GAS THROUGH THE MIXTURE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US734232A US2525892A (en) | 1947-03-12 | 1947-03-12 | Refining tall oil |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US734232A US2525892A (en) | 1947-03-12 | 1947-03-12 | Refining tall oil |
Publications (1)
Publication Number | Publication Date |
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US2525892A true US2525892A (en) | 1950-10-17 |
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ID=24950835
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US734232A Expired - Lifetime US2525892A (en) | 1947-03-12 | 1947-03-12 | Refining tall oil |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2791577A (en) * | 1952-05-05 | 1957-05-07 | Albemarle Paper Mfg Company | Process for refining tall oil |
EP1870445A1 (en) * | 2006-06-21 | 2007-12-26 | Linde Aktiengesellschaft | Process for producing tall oil and use of heating in the production of tall oil |
EP3666865A1 (en) * | 2018-12-14 | 2020-06-17 | UPM-Kymmene Corporation | Process for purifying renewable feedstock comprising fatty acids |
EP3666866A1 (en) * | 2018-12-14 | 2020-06-17 | UPM-Kymmene Corporation | Process for purifying feedstock comprising fatty acids |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1973790A (en) * | 1931-08-29 | 1934-09-18 | Sherwin Williams Co | Method of purifying vegetable oils |
US2223850A (en) * | 1937-10-18 | 1940-12-03 | Continental Res Corp | Process for refining and obtaining valuable products from tall oil |
US2235462A (en) * | 1938-08-11 | 1941-03-18 | Champion Paper & Fibre Co | Manufacture of an improved tall oil |
US2240365A (en) * | 1939-07-11 | 1941-04-29 | Colgate Palmolive Peet Co | Method of treating tall oil |
US2434699A (en) * | 1945-04-10 | 1948-01-20 | Ralph H Huff | Refining unsaturated acids and esters |
US2441198A (en) * | 1945-06-18 | 1948-05-11 | Ridbo Lab Inc | Tall oil treatment |
-
1947
- 1947-03-12 US US734232A patent/US2525892A/en not_active Expired - Lifetime
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1973790A (en) * | 1931-08-29 | 1934-09-18 | Sherwin Williams Co | Method of purifying vegetable oils |
US2223850A (en) * | 1937-10-18 | 1940-12-03 | Continental Res Corp | Process for refining and obtaining valuable products from tall oil |
US2235462A (en) * | 1938-08-11 | 1941-03-18 | Champion Paper & Fibre Co | Manufacture of an improved tall oil |
US2240365A (en) * | 1939-07-11 | 1941-04-29 | Colgate Palmolive Peet Co | Method of treating tall oil |
US2434699A (en) * | 1945-04-10 | 1948-01-20 | Ralph H Huff | Refining unsaturated acids and esters |
US2441198A (en) * | 1945-06-18 | 1948-05-11 | Ridbo Lab Inc | Tall oil treatment |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2791577A (en) * | 1952-05-05 | 1957-05-07 | Albemarle Paper Mfg Company | Process for refining tall oil |
EP1870445A1 (en) * | 2006-06-21 | 2007-12-26 | Linde Aktiengesellschaft | Process for producing tall oil and use of heating in the production of tall oil |
WO2007147837A1 (en) * | 2006-06-21 | 2007-12-27 | Linde Aktiengesellschaft | Process for producing tall oil and use of heating in the production of tall oil |
US20090227767A1 (en) * | 2006-06-21 | 2009-09-10 | Linde Aktiengesellschaft | Process for producing tall oil and use of heating in the production of tall oil |
EP3666865A1 (en) * | 2018-12-14 | 2020-06-17 | UPM-Kymmene Corporation | Process for purifying renewable feedstock comprising fatty acids |
EP3666866A1 (en) * | 2018-12-14 | 2020-06-17 | UPM-Kymmene Corporation | Process for purifying feedstock comprising fatty acids |
US20200190426A1 (en) * | 2018-12-14 | 2020-06-18 | Upm-Kymmene Corporation | Process for purifying feedstock comprising fatty acids |
US20200190427A1 (en) * | 2018-12-14 | 2020-06-18 | Upm-Kymmene Corporation | Process for purifying renewable feedstock comprising fatty acids |
US10947478B2 (en) * | 2018-12-14 | 2021-03-16 | Upm-Kymmene Corporation | Process for purifying feedstock comprising fatty acids |
US11053452B2 (en) * | 2018-12-14 | 2021-07-06 | Upm-Kymmene Corporation | Process for purifying renewable feedstock comprising fatty acids |
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