US2199653A - Process of treating tall oil - Google Patents
Process of treating tall oil Download PDFInfo
- Publication number
- US2199653A US2199653A US217974A US21797438A US2199653A US 2199653 A US2199653 A US 2199653A US 217974 A US217974 A US 217974A US 21797438 A US21797438 A US 21797438A US 2199653 A US2199653 A US 2199653A
- Authority
- US
- United States
- Prior art keywords
- resin
- alcohol
- acids
- tall oil
- 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
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- 238000000034 method Methods 0.000 title description 29
- 239000003784 tall oil Substances 0.000 title description 28
- 235000014113 dietary fatty acids Nutrition 0.000 description 58
- 239000000194 fatty acid Substances 0.000 description 58
- 229930195729 fatty acid Natural products 0.000 description 58
- 150000004665 fatty acids Chemical class 0.000 description 42
- 239000002253 acid Substances 0.000 description 31
- 239000011347 resin Substances 0.000 description 29
- 229920005989 resin Polymers 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 235000019441 ethanol Nutrition 0.000 description 28
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 27
- 150000007513 acids Chemical class 0.000 description 26
- 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 16
- -1 fatty acid esters Chemical class 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003377 acid catalyst Substances 0.000 description 8
- 150000005846 sugar alcohols Polymers 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000470 constituent Substances 0.000 description 5
- 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 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 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 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 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-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- the invention relates in general to the refining-of talloil and in particular to a. process of separating the fatty acids from the resin acids normally present in tall oil.
- Tall oil or talloel which literally means pine oil is the resinous and fatty by-product obtained in the production of paper pulp from resin-bearing woods by the so-called sulphate process.
- wood is digested lo-with an alkaline liquor containing sodium sulphate during which operation tall oil and soaps thereof accumulate on the surface of the wasteliquors.
- the main constituentspf this oil after acidification comprise fatty acids and resinic I 15 acids each of which are valuable commodities in substantially pure form.
- Various processes have been proposed in an attempt to effect a separation of tall oil into its main constituents, i. e. fatty acids and resin acids.
- a specific object of theinvention is to provide 40 a process of recovering from tall oil both the fatty acids and the resin acids; each in a substantially pure and uncontaminated state.
- a further object of the invention is to provide an improved and more efiicient process of separating the main constituents in tall oil.
- polyhydric alcohols such as glycerol, glycol, diethylene glycol,
- Example I of methyl alcohol and 3 parts of sulfuric acid.
- the excess alcohol is then distilled off at reduced pressure and the product of reaction consisting of a mixture of methyl esters of fatty acids and of free resin acids is washed free from sulfuric acid.
- 3 parts of glycerol of 98% strength are then added and the mixture is heated at 280 C. for 8 hours. At the end of this period the acid value has dropped below 2.0.
- the methyl esters of the fatty acids are then distilled off at a pressure of 2 mm. mercury between 145 and 165 C.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with alow boiling alcohol, esterifying the resin acids with an alcohol having a higher boiling point than the first alcohol and distilling off the fatty acid esters thus formed.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with a monohydric alcohol, esterifying the resinacids with a polyhydric alcohol and distilling off the fatty acid ester thus formed.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with methyl alcohol in the presence of an acid catalyst, esterifying the resin acids with a polyhydric, alcohol and distilling off the fatty acid ester thus formed.
- a process of treating tall, oil to.separate the fatty acid components from the resin acidcomponents which comprises esterifying the fatty acids with ethyl alcohol in the presence of an acid catalyst, esterifying the resin acids with a polyhydric alcohol and distilling off the fatty acid ester thus formed.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fattyaci'ds with a butyl alcohol in the presence of an v acid catalyst, esterifying the resin acids with a polyhydric alcohol and distilling off the fatty acid ester thus formed.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with a monohydric alcohol having not more than 5 carbon atoms in the presence of an acid catalyst, esterifying the resin acids with glycerol and distilling off the fatty acid ester thus formed.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with methyl alcohol in the presence of an acid catalyst, esterifying the resin acids with glycerol and distillingoff the fatty acid ester thus formed.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with ethyl alcohol in the presence of an acid catalyst, esterifying the resin acid with glycerol and distilling oil the fatty acid ester thus formed.
- a process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with a butyl alcohol in the presence of an acid catalyst, esterifying the resin acids with glycerol and distilling off the fatty acid ester thus formed.
- the process of separating the fatty constituents from the resinous constituents of tall oil which comprises esterifying the fatty acids with an alcohol 01 the group that produces fatty acid esters of relatively high vapor pressure, esterii'ying the resin acids with an alcohol of the type that produces resin esters of low vapor pressure with respect to that of the fatty acid estersand separating the fatty acid esters by distillation.
- a process of recovering the fatty components from a mixture containing fatty acids and resin acids which comprises esterifying the fatty acids with a monohydric alcohol having no more than 5 carbon atoms, esteritying the resin acids 5 with a polyhydric alcohol and recovering the fatty acid esters thus produced by distillation.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented my 1, 1940 UNITED STATES PATENT OFFICE PROCESS OF TREATING TALL OIL .No Drawing. Application July 7, 1938,
. Serial No. 217,974
14 Claims.
The invention relates in general to the refining-of talloil and in particular to a. process of separating the fatty acids from the resin acids normally present in tall oil.
Tall oil or talloel which literally means pine oil is the resinous and fatty by-product obtained in the production of paper pulp from resin-bearing woods by the so-called sulphate process. In the sulphate process wood is digested lo-with an alkaline liquor containing sodium sulphate during which operation tall oil and soaps thereof accumulate on the surface of the wasteliquors. The main constituentspf this oil after acidification comprise fatty acids and resinic I 15 acids each of which are valuable commodities in substantially pure form. Various processes have been proposed in an attempt to effect a separation of tall oil into its main constituents, i. e. fatty acids and resin acids. One process comprises 10 esterifying the fatty acids in tall oil with a low boiling alcoholand separating the resulting fatty ester from the free rosin acids by alkali extrac-\ so distilled off. While the foregoing and other known processes have been employed with varying degrees of success, the fact remains that only a partial separation is effected thereby. The resulting fatty acids and their esters are invariably contaminated with appreciable quantities of resin acids.
The general object of the invention is'to obviate the foregoing and other disadvantages.
A specific object of theinvention is to provide 40 a process of recovering from tall oil both the fatty acids and the resin acids; each in a substantially pure and uncontaminated state.
A further object of the invention is to provide an improved and more efiicient process of separating the main constituents in tall oil.
Other objects will in part be obvious and will in part appear hereinafter. It has now been found thata more complete separation of tall oil into its fatty and resinous 5o constituents can be efiected according to the invention by first subjecting the fatty acids in tall oil to the esterifying action of an alcohol of the kind that will result in esters of relatively high vapor pressure and esterifying the resin acids with a different alcohol of the type that produces partially or completely refined state.
- like may be .used. Esterification of the resin acids For a fuller understanding of the nature and objects of the invention, reference should be had esters of low vapor pressure. The resulting mixture comprises relatively low boiling fatty'acid esters and higher boiling resin esters. The fatty acid esters may be distilled off under reduced pressure from the resin esters with or without the 5 useof steam distillation. The fatty acid esters thus obtained are practically free from contamination with resin acids or esters thereof which remain in the still.
The invention accordingly comprises rthe sevl0 er-al steps and the relation of one or more of such steps with respect to each of the others thereof, which will be exemplified in the process hereinafter disclosed, and the scope of the invention,
will be indicated in the claims. 16:
In carrying out the process of the invention the tall oil to be treated may be in the crude or Any suitable relatively low boiling alcohol having a low. carbon content preferably not more than 5 car- 20 bon atoms may be used in the esterification of the fatty acids. Examples of. such alcohols include, inter alia monohydric alcohols such as the methyl, ethyl, propyl, isopropyl, butyl, isobutyl,
etc. alcohols. For the esterification of the rosin 25.
acids, it is preferred to employ polyhydric alcohols, such as glycerol, glycol, diethylene glycol,
triethylene glycol,'propylene glycol, sorbitol, mannitol or any other alcohol that will produce resin esters having a boiling point sufliciently high with 30 respect to that of the fatty acid ester formed to. permit a complete separation of the latter by distillation. While any suitable polyhydric alcohol may be used, it is highly preferred to employ glycerol for various reasons including cost and efficiency of operation.
During the step of esterifying the fatty acids,
suitable catalysts, such as sulfuric acid, hydrochloric acid, naphthalene-fl-sulfonic acid or the may be carried out without the use of a catalyst,
but it is preferred to accelerate the reaction by addition of such catalyzing agents as finely divided zinc, tin, zinc oxide, magnesium oxide or the like.
to the following examples which are given merely to furthr illustrate the invention and are not to be construed in a limiting sense, all parts given being by weight:
Example I of methyl alcohol and 3 parts of sulfuric acid. The excess alcohol is then distilled off at reduced pressure and the product of reaction consisting of a mixture of methyl esters of fatty acids and of free resin acids is washed free from sulfuric acid. 3 parts of glycerol of 98% strength are then added and the mixture is heated at 280 C. for 8 hours. At the end of this period the acid value has dropped below 2.0. The methyl esters of the fatty acids are then distilled off at a pressure of 2 mm. mercury between 145 and 165 C.
The methyl esters consist of a straw-colored liquid, are substantially free from rosin and have an acid value of 1.9. They may be used as such in the various industries or they may be split into their fatty acids, or they may be sulfated, phosphated or hydrogenated according to-known procedures. The still residue consisting mainly of glycerides of the resin acids is a viscous browncolored oil having an acid value of 0.45.
Example II Gaseous hydrochloride is passed into 30 parts of ethyl alcohol until a solution of 5% thereof in the alcohol is obtained. 100 parts of crude tall oil having a rosin content of 37.5% are then added and the mixture is refluxed for 5 hoursto effect esterification of the fatty acids. The excess alcohol is then distilled off under reduced pressure.
6.5 parts of glycerol of 90% strength and .3 part of zinc oxide are then added and the mixture is heated under an atmosphere of CO2 at 235 to 240 C. for 6 hours. The ethyl esters of the fatty acids are then distilled off at 15 mm. mercury between 200 and 220? C. 1
Example!!! 100 parts of a distilled tall oil ,having al-rosin content of 23% are refluxed with 60 parts of nbutyl alcohol and 5 parts of naphthalene-p-sulfonic acid for 8 hours. The excess butyl alcohol is then distilled off at reduced pressure and the naphthalene sulfonic acid is washed out of the mixture. 4 parts of glycerol of 90% strength and .3 part of magnesium oxide are then added and the mixture is heated between 260-to 270 C. for 6 hours or until the acid value has dropped below 5.0. The butyl esters of the fatty acids are then distilled off at a pressure of 3 mm. mercury between 200 and 215 C.
While the present invention is particularly adapted for the treatment of tall oil, it is within the purview of the invention to employ the process for separating resin acids and fatty acids present in any mixture.
Since certain changes may be made in carrying out the above process without departing from the scope of the invention, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.
It is also to be understood that the following claims are intended to cover all the generic and specific features of the invention herein described, and all statements of the scope of the invention, which as a matter of language might be said to fall therebetween.
Having described my invention, what I claim as new and desire to secure by Letters Patent is:
1. In a process of treating tall oil to separate the fattyacid .components from the resin acid componentsthe steps which comprise esterifying the fatty acids with a low boiling alcohol and subsequently esterifying the resin acids with an alcohol having a higher boiling pointthan the first alcohol.
2. In a process of treating tall oil to separate the fatty acid components from t resin acid components, the steps which comprise esterifying the fatty acids with a monohydric alcohol and subsequently esterifying the resin acids with a polyhydric alcohol.
3. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with alow boiling alcohol, esterifying the resin acids with an alcohol having a higher boiling point than the first alcohol and distilling off the fatty acid esters thus formed.
4. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with a monohydric alcohol, esterifying the resinacids with a polyhydric alcohol and distilling off the fatty acid ester thus formed.
5. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with a monohydric alcohol in the presence of an acid catalyst, esterifying the resin acids with a polyhydric alcohol and distilling of! the fatty acid ester thus formed.
' 6. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with methyl alcohol in the presence of an acid catalyst, esterifying the resin acids with a polyhydric, alcohol and distilling off the fatty acid ester thus formed. 1
-'7. A process of treating tall, oil to.separate the fatty acid components from the resin acidcomponents which comprises esterifying the fatty acids with ethyl alcohol in the presence of an acid catalyst, esterifying the resin acids with a polyhydric alcohol and distilling off the fatty acid ester thus formed.
8. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fattyaci'ds with a butyl alcohol in the presence of an v acid catalyst, esterifying the resin acids with a polyhydric alcohol and distilling off the fatty acid ester thus formed.
9. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with a monohydric alcohol having not more than 5 carbon atoms in the presence of an acid catalyst, esterifying the resin acids with glycerol and distilling off the fatty acid ester thus formed.
10. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with methyl alcohol in the presence of an acid catalyst, esterifying the resin acids with glycerol and distillingoff the fatty acid ester thus formed.
11. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with ethyl alcohol in the presence of an acid catalyst, esterifying the resin acid with glycerol and distilling oil the fatty acid ester thus formed.
12. A process of treating tall oil to separate the fatty acid components from the resin acid components which comprises esterifying the fatty acids with a butyl alcohol in the presence of an acid catalyst, esterifying the resin acids with glycerol and distilling off the fatty acid ester thus formed.
13. The process of separating the fatty constituents from the resinous constituents of tall oil which comprises esterifying the fatty acids with an alcohol 01 the group that produces fatty acid esters of relatively high vapor pressure, esterii'ying the resin acids with an alcohol of the type that produces resin esters of low vapor pressure with respect to that of the fatty acid estersand separating the fatty acid esters by distillation.
14. A process of recovering the fatty components from a mixture containing fatty acids and resin acids which comprises esterifying the fatty acids with a monohydric alcohol having no more than 5 carbon atoms, esteritying the resin acids 5 with a polyhydric alcohol and recovering the fatty acid esters thus produced by distillation.
ERNEST SEGESSEMANN.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US217974A US2199653A (en) | 1938-07-07 | 1938-07-07 | Process of treating tall oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US217974A US2199653A (en) | 1938-07-07 | 1938-07-07 | Process of treating tall oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2199653A true US2199653A (en) | 1940-05-07 |
Family
ID=22813246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US217974A Expired - Lifetime US2199653A (en) | 1938-07-07 | 1938-07-07 | Process of treating tall oil |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2199653A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2491660A (en) * | 1947-01-15 | 1949-12-20 | Du Pont | Preparation of esters of terephthalic acid |
-
1938
- 1938-07-07 US US217974A patent/US2199653A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2491660A (en) * | 1947-01-15 | 1949-12-20 | Du Pont | Preparation of esters of terephthalic acid |
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