US2388412A - Fractionation of tall oil - Google Patents
Fractionation of tall oil Download PDFInfo
- Publication number
- US2388412A US2388412A US331602A US33160240A US2388412A US 2388412 A US2388412 A US 2388412A US 331602 A US331602 A US 331602A US 33160240 A US33160240 A US 33160240A US 2388412 A US2388412 A US 2388412A
- Authority
- US
- United States
- Prior art keywords
- tall oil
- liquefied
- fatty acids
- propane
- temperature
- 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
- 239000003784 tall oil Substances 0.000 title description 22
- 238000005194 fractionation Methods 0.000 title description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 24
- 235000014113 dietary fatty acids Nutrition 0.000 description 18
- 229930195729 fatty acid Natural products 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- 150000004665 fatty acids Chemical class 0.000 description 18
- 229930195733 hydrocarbon Natural products 0.000 description 17
- 150000002430 hydrocarbons Chemical class 0.000 description 17
- 239000001294 propane Substances 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000000605 extraction Methods 0.000 description 9
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 8
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 8
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241001249542 Leonia <angiosperm> Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011345 viscous material 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
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
Definitions
- This invention is concerned with the fractionation of tall oil.
- Tall oil is composed principally of rosin acids and fatty acids. The most valuable part of tall oil is its fatty acid content.
- a process of refining and fractionation of tall oil has been described. The method outlined therein is particularly applicable to a batch process.
- We have discovered that the fatty acid content of tall oil can be separated from the other constituents in a continuous process using liquefied, normally gaseous, hydrocarbons. The advantages of the present process are that it makes possible economies in heat'and equipment as well as increasing the yield of substantially pure fatty acids.
- the fatty acids are extracted from crude tall oil by liquefied, normally gaseous, hydrocarbons at temperatures such that only fatty acids are soluble in the hydrocarbon solvent.
- the extraction is most economically carried out in a continuous counter-current manner.
- Crude tall oil is introduced at one end of the extraction system and a liquefied, normally gaseous, hydrocarbon introduced at the other end of'the extraction system.
- a solution of fatty acid dissolved in the liquefied, normally gaseous, hydrocarbon is withdrawn from one end of the system and a liquid composed primarily of rosin, in which some of the liquefied, normally gaseous, hydrocarbon is dissolved, is withdrawn from the other end.
- the simplest type of contacting equipment such as a packed tower can be employed.
- Crude tall oil which has been preheated to the proper temperature is introduced close to the top of the tower.
- a liquefied, normally gaseous, hydrocarbon is introduced close to the bottom of the tower.
- hydrocarbon solution of fatty acids is withdrawn from the top of the tower while a liquid composed principally of rosin, in which a small percentage of the liquefied, normally gaseous, hydrocarbon is dissolved, is withdrawn from the base of the tower.
- the temperature at which the extraction is carried out is a function of the composition of the olvent employed and the ratio of volume of tall oil treated to volume of solvent used. If it is desirable, a temperature gradient can be maintained between the two ends of the extraction system. In counter-current processes of this type, it is desirable that the two immiscible liquids be as fluid as possible and differ widely. in density. As the tall oil is a very viscous material at room (oi. zoo-47.5)
- propane is the preferred solvent.
- propane a. temperature of about C. is used. Rosin is substantially insoluble in liquidv propane at 90 0.
- the high temperature end of the system is that at which the fatty acid solution leaves the system.
- a temperature gradient is employed, a condition exists that is similar to reflux in a distillation.
- Any undesirable material that dissolves in the hydrocarbon phase at the cold end of the system precipitates at the hot end of the system. This permits the amount of solvent that must be circulated to fractionate a. given quantity of tall oil to be reduced.
- the solvent present in each phase is conveniently, readily and inexpensively separated from each phase by distillation. The solvent is then returned to the extraction step. Because the solvent is so easily recovered, the process is operated with very low solvent losses.
- the products of this process are substantially pure fatty acids, secured in yields that are almost quantitative, and rosin containing all the other constituents of tall oil except the fatty acids.
- one liquid phase consisting essentially of fatty acids dissolved in the liquefied hydrocarbon and a second phase consisting essentially of liquid rosin containing some dissolved hydrocarbon.
- a process of treating tall oil and recovering a' fatty acid fraction and a rosin fraction therefrom which comprises passing preheated tall oil to the upper section of a continuous countercurrent extraction tower, counter-currently passing liquid propane at a temperature of substantially 90 C. into the lower section of said tower; continuously withdrawing from the upper portion of the tower a liquid fraction consisting of fatty acids dissolved in propane and continuously withdrawing from the lower end of the system a liquid rosin fraction containing some dissolved propane. 5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
Patented Nov. 6, 1945 Arthur W. Hixson, Leonia, N.
New York, N. Y., Foundation, aware J., and Ralph Miller,
assignors to The Chemical Incorporated, acorporation of Del- No Drawing. Application April 25, 1940,
. Serial No. 331,602
Claims.
This invention is concerned with the fractionation of tall oil.
Tall oil is composed principally of rosin acids and fatty acids. The most valuable part of tall oil is its fatty acid content. In our copending application Serial No. 264,780, filed March 9, 1939, U. S. Patent 2,247,496, a process of refining and fractionation of tall oil has been described. The method outlined therein is particularly applicable to a batch process. We have discovered that the fatty acid content of tall oil can be separated from the other constituents in a continuous process using liquefied, normally gaseous, hydrocarbons. The advantages of the present process are that it makes possible economies in heat'and equipment as well as increasing the yield of substantially pure fatty acids.
The fatty acids are extracted from crude tall oil by liquefied, normally gaseous, hydrocarbons at temperatures such that only fatty acids are soluble in the hydrocarbon solvent. The extraction is most economically carried out in a continuous counter-current manner. Crude tall oil is introduced at one end of the extraction system and a liquefied, normally gaseous, hydrocarbon introduced at the other end of'the extraction system. A solution of fatty acid dissolved in the liquefied, normally gaseous, hydrocarbon is withdrawn from one end of the system and a liquid composed primarily of rosin, in which some of the liquefied, normally gaseous, hydrocarbon is dissolved, is withdrawn from the other end. The simplest type of contacting equipment such as a packed tower can be employed. Crude tall oil which has been preheated to the proper temperature is introduced close to the top of the tower. A liquefied, normally gaseous, hydrocarbon is introduced close to the bottom of the tower. The
hydrocarbon solution of fatty acids is withdrawn from the top of the tower while a liquid composed principally of rosin, in which a small percentage of the liquefied, normally gaseous, hydrocarbon is dissolved, is withdrawn from the base of the tower.
The temperature at which the extraction is carried out is a function of the composition of the olvent employed and the ratio of volume of tall oil treated to volume of solvent used. If it is desirable, a temperature gradient can be maintained between the two ends of the extraction system. In counter-current processes of this type, it is desirable that the two immiscible liquids be as fluid as possible and differ widely. in density. As the tall oil is a very viscous material at room (oi. zoo-47.5)
temperature, it is desirable to operate at elevated temperatures. For this reason, propane is the preferred solvent. When propane is employed, a. temperature of about C. is used. Rosin is substantially insoluble in liquidv propane at 90 0.,
while the fatty acids present in tall oil are co pletely miscible with propane at 90 C. If a mixture of hydrocarbons is employed, the best temperature will be a function of the composition 'of the solvent.
If a mixture of propane and ethane is used, a. lower temperature is maintained during the extraction than is used when propane is employed alone. If butane or isobutane is employed, the temperature must be raised for optimum results. Any combination of liquefied, normally gaseous, hydrocarbons can be used.
If a temperature radient is maintained, the high temperature end of the system is that at which the fatty acid solution leaves the system. When a temperature gradient is employed, a condition exists that is similar to reflux in a distillation. The same advantages that accrue from the use of reflux in a distillation can be obtained by use of a temperature gradient. Any undesirable material that dissolves in the hydrocarbon phase at the cold end of the system precipitates at the hot end of the system. This permits the amount of solvent that must be circulated to fractionate a. given quantity of tall oil to be reduced.
Because of the enormous difference in volatility between the solvents employed and tall oil, the solvent present in each phase is conveniently, readily and inexpensively separated from each phase by distillation. The solvent is then returned to the extraction step. Because the solvent is so easily recovered, the process is operated with very low solvent losses.
The products of this process are substantially pure fatty acids, secured in yields that are almost quantitative, and rosin containing all the other constituents of tall oil except the fatty acids.
We claim:
1. The process of extracting fatty acids from tall oil by contacting same with a liquefied, normally gaseous, hydrocarbon at elevated temperatures at which the rosin is insoluble in the liquefied hydrocarbons in a continuous counter-current system, continuously withdrawing from said.
system one liquid phase consisting essentially of fatty acids dissolved in the liquefied hydrocarbon and a second phase consisting essentially of liquid rosin containing some dissolved hydrocarbon.
2. The process of extracting fatty acids from tall oil comprising subjecting said oil to a mixture of liquefied, normally gaseous, hydrocarbons at elevated temperatures of the order of 90 C. sufflciently high to distribute the fatty acids and the rosin respectively into two liquid phases in a continuous counter-current relation.
3. A process in accordance with claim 1 in which the solvent is propane and in which the temperature in the system is maintained about 90 C.
4. A process of treating tall oil and recovering a' fatty acid fraction and a rosin fraction therefrom which comprises passing preheated tall oil to the upper section of a continuous countercurrent extraction tower, counter-currently passing liquid propane at a temperature of substantially 90 C. into the lower section of said tower; continuously withdrawing from the upper portion of the tower a liquid fraction consisting of fatty acids dissolved in propane and continuously withdrawing from the lower end of the system a liquid rosin fraction containing some dissolved propane. 5. A process in accordance with claim 4 in which the two withdrawn fractions are separately treated to recover the contained propane and recycling the recovered propane for further extraction of tall oil.
ARTHUR W. HIXSON.
RALPH MILLER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US331602A US2388412A (en) | 1940-04-25 | 1940-04-25 | Fractionation of tall oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US331602A US2388412A (en) | 1940-04-25 | 1940-04-25 | Fractionation of tall oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2388412A true US2388412A (en) | 1945-11-06 |
Family
ID=23294622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US331602A Expired - Lifetime US2388412A (en) | 1940-04-25 | 1940-04-25 | Fractionation of tall oil |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2388412A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567541A (en) * | 1946-07-26 | 1951-09-11 | Swift & Co | Manufacture of higher alcohols |
| US4308200A (en) * | 1980-07-10 | 1981-12-29 | Champion International Corporation | Extraction of coniferous woods with fluid carbon dioxide and other supercritical fluids |
| EP2602306A1 (en) * | 2011-12-08 | 2013-06-12 | Invico Tech AB | Process for obtaining a diesel like fuel |
| WO2013083768A1 (en) * | 2011-12-08 | 2013-06-13 | Invico Tech Ab | Process for obtaining a diesel like fuel |
-
1940
- 1940-04-25 US US331602A patent/US2388412A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567541A (en) * | 1946-07-26 | 1951-09-11 | Swift & Co | Manufacture of higher alcohols |
| US4308200A (en) * | 1980-07-10 | 1981-12-29 | Champion International Corporation | Extraction of coniferous woods with fluid carbon dioxide and other supercritical fluids |
| EP2602306A1 (en) * | 2011-12-08 | 2013-06-12 | Invico Tech AB | Process for obtaining a diesel like fuel |
| WO2013083768A1 (en) * | 2011-12-08 | 2013-06-13 | Invico Tech Ab | Process for obtaining a diesel like fuel |
| US9487717B2 (en) | 2011-12-08 | 2016-11-08 | Invico Tech Ab | Process for obtaining a diesel like fuel |
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