US1736802A - Process of treating talloel - Google Patents
Process of treating talloel Download PDFInfo
- Publication number
- US1736802A US1736802A US22324127A US1736802A US 1736802 A US1736802 A US 1736802A US 22324127 A US22324127 A US 22324127A US 1736802 A US1736802 A US 1736802A
- Authority
- US
- United States
- Prior art keywords
- talloel
- treating
- acid
- fatty acid
- alcohol
- 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
- 238000000034 method Methods 0.000 title description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- 229930195729 fatty acid Natural products 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000001117 sulphuric acid Substances 0.000 description 7
- 235000011149 sulphuric acid Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- -1 fatty acid ester Chemical class 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 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 1
- 240000002989 Euphorbia neriifolia Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
- C11B13/005—Recovery of fats, fatty oils or fatty acids from waste materials of residues of the fabrication of wood-cellulose (in particular tall-oil)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Definitions
- the invention is concerned with the same problem, resulting in the separation of the majority of the fatty acid'from the t-alloel ways of obtaining this result.
- One well known method consists in first of all distilling the talloel and thereupon subjecting the distillate to a further fractional distillation.
- the fatty acid ester solution is washed out with H O or 50% alcohol after separation of the lower layer, then freed from benzene by distillation and now forms a yellow oil, which smells like olive oil.
- the alcohol is removed from the aqueousalcoholic resin soap solution by distillation, the remaining aqueoussoap solution is decomposed by diluted sulphuric acid whilst esterification of the fatty acids but not of the stirring with benzene.
- the talloel esterified in this manner is then distilled in any known way.
- the term talloel which literally means pine oil is a liquid resin.
- the ester mixture is now mixed with such a quantity of aqueous caustic soda solution that ing the split off or separated alcohol.
- acids are separated from the soap by decomposition with dilute mineral acid.
- Th quantity of y The p ocess of eat ng ta loel to sepacid which considerably varies in talloel a alkali used depends on the. content of resifig onthe content of sulphuric acid.
- Thecooled solution is then stirred thor oughly twice with benzene or, for instance,
- arate the liquid fatty acid componentsthereupper layer contains the fatty acid ethyl es-- terification mixture.
- the step which comprises subjecting the talloel to the action of an esterifyingmixture comprising alcohol and sulphuric acidto esterify only the fatty acid components.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Nov. 26, 1929 PATENT OFFICE WILLI SCHULTZE, OF HALLE-ON-THE-SAILE, GERMANY PROCESS TREATINGJPALLOEL 7 Ho Drawing. Application filed September 80, 1927, Serial No. 223,241, and in Germany October 11, 1926.
-si1lt hitherto obtained has not been satisfac- 10 (in some cases up to 90%). There are two steam or under vacuum or both, one can scptory however.
The invention is concerned with the same problem, resulting in the separation of the majority of the fatty acid'from the t-alloel ways of obtaining this result. One well known method consists in first of all distilling the talloel and thereupon subjecting the distillate to a further fractional distillation.
Applicants method which is described sub sequently is based on esterifying the talloel according to methods which merely effect an ters and unsaponifiable matter dissolved in benzene, the lower layer the soda soaps of the resin-acids in aqueous-alcoholic solution.
The fatty acid ester solution is washed out with H O or 50% alcohol after separation of the lower layer, then freed from benzene by distillation and now forms a yellow oil, which smells like olive oil.
By careful distillation, for instance, with arate the fatty acid esters from the unsaponifiable matter and thus obtain the esters absolutely pure.
-The alcohol is removed from the aqueousalcoholic resin soap solution by distillation, the remaining aqueoussoap solution is decomposed by diluted sulphuric acid whilst esterification of the fatty acids but not of the stirring with benzene. The extraction of esv resinic acids contained in the talloel. for instance the talloel is treated with alcohol and concentrated sulphuric acid; about 100 kg. talloel, 25 kg. alcohol and 4 kg. concentrated sulphuric acid of 66 B. The talloel esterified in this manner is then distilled in any known way. The term talloel which literally means pine oil is a liquid resin.
As a specific example, I mix 100 kilos of talloel with 25 kilos alcohol and 4 kilos sul-' phuric acid of 66 B and heat the mixture under a reflux for two hours. The reaction mixture is then left at rest until the sulphuric acid layer has separated out is a bottom layer. The sulphuric acid layer is drawn off and discarded.
The ester mixture is now mixed with such a quantity of aqueous caustic soda solution that ing the split off or separated alcohol. The
acids are separated from the soap by decomposition with dilute mineral acid.
According to the methods referredto it is possible to obtain from the talloel, fatty acids which contain such a small amount of resin acids, that they can befurther used indus-- trially, which was impossible according to methods employed hitherto owing to the detthe unesterified resin-acid and residue of sulrimental, Content 0f resinphuric acid are neutralized. The end or final pointof the neutralizatidn is ascertained by testing with an indicator, for instance, phenolphthalein. A slight excess of; caustic soda Having now particularly described and ascertained the nature of my said invention and in what manner the same is to be performed, I declare that what I claim is should preferably be used. Th quantity of y The p ocess of eat ng ta loel to sepacid which considerably varies in talloel a alkali used depends on the. content of resifig onthe content of sulphuric acid.
Thecooled solution is then stirred thor oughly twice with benzene or, for instance,
with about 25% of the neutralized esterifying mixture. Two layers are formed. The
" arate the liquid fatty acid componentsthereupper layer contains the fatty acid ethyl es-- terification mixture.
2. The process of treating talloelto separate the liquid fatty acid components thereof from the resinic acid components thereof which comprises treating the talloel with a mixture of alcohol and sulphuric acid to esterify only the liquid fatty acids, and thenseparating the esterified fatty acids from the esterification mixture.
3. In the process of treating talloel to separate the liquid fatty acid components thereof from the resinic acid components thereof, the step which com rises su jecting the talloel to the action 0 an esterifying agent to esterify only the liquid fatty acid compo-v nents. 1
4. In the process of treating talloel to separate the liquid fatty acid components thereof from the resinic acid components thereof, the step which comprises subjecting the talloel to the action of an esterifyingmixture comprising alcohol and sulphuric acidto esterify only the fatty acid components.
5. The process of recovering the liquid I fatty acids occurring in talloel which comprises subjecting the talloel to the action of an esterifyin agent to esterify only the liquid fatty aci 5 contained therein, se arating the fatty acid esters so prepared mm the esterification mixture and then treating the esters with a hydrolytic agent to obtain the free fatty acids.
In testimony whereof I have signed my name to this'specificationt WILLI SCHULTZE.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1736802X | 1926-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1736802A true US1736802A (en) | 1929-11-26 |
Family
ID=7741203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US22324127 Expired - Lifetime US1736802A (en) | 1926-10-11 | 1927-09-30 | Process of treating talloel |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1736802A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573890A (en) * | 1948-09-04 | 1951-11-06 | Pittsburgh Plate Glass Co | Separation of tall oil components |
| US4101535A (en) * | 1976-04-01 | 1978-07-18 | Hudson Pulp & Paper Corp. | Method and apparatus for recovering saponified tall oil |
| US20070015904A1 (en) * | 2003-02-21 | 2007-01-18 | Setsuo Sato | Process for obtaining fatty acid alkyl esters, rosin acids and sterols from crude tall oil |
| EP4172296A4 (en) * | 2020-06-26 | 2024-07-10 | Molcycle Oy | PROCESS FOR PROCESSING SOAPS FROM BLACK LIQUEUR |
-
1927
- 1927-09-30 US US22324127 patent/US1736802A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573890A (en) * | 1948-09-04 | 1951-11-06 | Pittsburgh Plate Glass Co | Separation of tall oil components |
| US4101535A (en) * | 1976-04-01 | 1978-07-18 | Hudson Pulp & Paper Corp. | Method and apparatus for recovering saponified tall oil |
| US20070015904A1 (en) * | 2003-02-21 | 2007-01-18 | Setsuo Sato | Process for obtaining fatty acid alkyl esters, rosin acids and sterols from crude tall oil |
| EP4172296A4 (en) * | 2020-06-26 | 2024-07-10 | Molcycle Oy | PROCESS FOR PROCESSING SOAPS FROM BLACK LIQUEUR |
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