US778980A - Process of producing fatty acids. - Google Patents
Process of producing fatty acids. Download PDFInfo
- Publication number
- US778980A US778980A US18673803A US1903186738A US778980A US 778980 A US778980 A US 778980A US 18673803 A US18673803 A US 18673803A US 1903186738 A US1903186738 A US 1903186738A US 778980 A US778980 A US 778980A
- Authority
- US
- United States
- Prior art keywords
- fatty acids
- acidulated
- aromatic bases
- derivatives
- producing 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
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title description 14
- 229930195729 fatty acid Natural products 0.000 title description 14
- 239000000194 fatty acid Substances 0.000 title description 14
- 150000004665 fatty acids Chemical class 0.000 title description 14
- 238000000034 method Methods 0.000 title description 13
- 125000003118 aryl group Chemical group 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000501754 Astronotus ocellatus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- ZOLJFBQEKSZVCB-UHFFFAOYSA-N n-phenyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=CC=C1 ZOLJFBQEKSZVCB-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Definitions
- My invention relates to a process of producing fatty acids; and it consists in heating acidulated derivatives of aromatic bases with sulfuric acid and separating the fatty acids produced therebyfrom the sulfates of the aromatic bases which are formed in the process.
- the value of this process substantially depends on the fact that the acidulated derivatives of aromatic bases on a commercial scale are obtained in the form of compounds or mixtures containing the radicals of more than one fatty acid and eventually several aromatic bases. From these compounds of acidulated derivatives of aromatic bases especially only some constituents-for instance, that containing the radical of stearic acidare separated by fractional distillation or by other known processes for further use, whereas the remaining mixture frequently cannot be profitably employed.
- my invention is adapted to, produce valuable productsnamely, fatty acids and sulfates of aromatic bases from the said compounds of acidulated derivatives of aromatic bases.
- the performance of my invention may be seen from the following example: I heat a compound of acidulated derivatives of anilin of one hundred parts in weight with sixty-six parts of sulfuric acid of forty-two-percent. concentration up to about 250 centigrade. When doing so, the sulfuric acid combines with the anilin, whereas the fatty acids are freed in a substantially pure form and in a condition adapted to be saponified by alkali in aqueous solution,forming then a soap which gives a clear solution in water.
- The'reactions taking place may be seen from the following formula: l
- R is identical to (111E135 for stearic acid, or,. in-other words, if stearic anilid is the particular raw material treated then R will be C11H35.
- the reaction between the acidulated derivations of anilin and the sulfuric acid is preferably performed in a closed vessel to avoid the evaporation of Water from the sulfuric acid.
- the time of reaction depends in wide ranges from the more orless intimate mixture of the components during the process. For this reason it'is advisable to provide the vessel of reaction with agitating means.
- the temperature of 250 centigrade above mentioned may be varied. However, lowertemperatures generally require more time for finishing the reaction.
- the sulfate of anilin may be used for the production of anilin in awell-known manner or it may be used for some other purpose for'instance, for the production of sulfanilic acid-in a known manner by heating the sulfate of anilin, after evaporation of its solution,
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
' UNITED STATES Patented January 3, 1905.
PATENT 'OFFICE.
PROCESS OF PRODUCING FATTY ACIDS.
SPECIFICATION forming part of Letters Patent No. 778,980, dated January 3, 1905.
Application filed December 26, 1903. Serial No. 186,738.
To all whom it may concern.-
Be it known that I, OSOAR LIEBREIOH, a citizen of the German Empire, residing at Berlin, Germany, have invented a new and useful Improvement in and Relating to Processes of Producing Fatty Acids, of which the follow ing is a specification.
My invention relates to a process of producing fatty acids; and it consists in heating acidulated derivatives of aromatic bases with sulfuric acid and separating the fatty acids produced therebyfrom the sulfates of the aromatic bases which are formed in the process.
The value of this process substantially depends on the fact that the acidulated derivatives of aromatic bases on a commercial scale are obtained in the form of compounds or mixtures containing the radicals of more than one fatty acid and eventually several aromatic bases. From these compounds of acidulated derivatives of aromatic bases especially only some constituents-for instance, that containing the radical of stearic acidare separated by fractional distillation or by other known processes for further use, whereas the remaining mixture frequently cannot be profitably employed. Now my invention is adapted to, produce valuable productsnamely, fatty acids and sulfates of aromatic bases from the said compounds of acidulated derivatives of aromatic bases. At the same time my new process cheapens the production of acidulated derivatives of aromatic bases and of pure glycerin from glucerids of fatty acids, the so-called fats and oils, in accordance with my invention for which I have obtained Letters Patent in the United States numbered 7 41, 585. In performing the last-named process I obtain besides pure glycerin a mixture of several acidulated derivatives of aromatic bases. As above stated, only some constituents of such mixture are practically directly used, whereas the others at this time for themselves have less technical value, so that itwould be desirable to dissociate same, so as to form free fatty ate the aromatic bases.
vention realizes this effect.
Now my present in- Therefore by the combination of my said former process forming the subject-matter of my said United acids and to regenerpound of acidulated derivatives of aromatic.
bases with sulfuric acid, fatty acids and sulfates of aromatic bases.
Obviously I can use for my combined process every kind of cheap fat or oil, and I obtain the following valuable products in comparatively pure condition: acidulated derivatives of aromatic bases, anhydrous glycerin, fatty acids, and sulfates of aromatic bases.
The performance of my invention may be seen from the following example: I heat a compound of acidulated derivatives of anilin of one hundred parts in weight with sixty-six parts of sulfuric acid of forty-two-percent. concentration up to about 250 centigrade. When doing so, the sulfuric acid combines with the anilin, whereas the fatty acids are freed in a substantially pure form and in a condition adapted to be saponified by alkali in aqueous solution,forming then a soap which gives a clear solution in water. The'reactions taking place may be seen from the following formula: l
QCGHS. NH.
'stearic anili In this formula R is identical to (111E135 for stearic acid, or,. in-other words, if stearic anilid is the particular raw material treated then R will be C11H35. I
The reaction between the acidulated derivations of anilin and the sulfuric acid is preferably performed in a closed vessel to avoid the evaporation of Water from the sulfuric acid. The time of reaction depends in wide ranges from the more orless intimate mixture of the components during the process. For this reason it'is advisable to provide the vessel of reaction with agitating means.
The temperature of 250 centigrade above mentioned may be varied. However, lowertemperatures generally require more time for finishing the reaction.
The sulfate of anilin may be used for the production of anilin in awell-known manner or it may be used for some other purpose for'instance, for the production of sulfanilic acid-in a known manner by heating the sulfate of anilin, after evaporation of its solution,
' up to 250 centigrade.
The decomposition of the acidulated derivatives of aromatic bases by sulfuric acid is a remarkable effect, because alkali is not suitable for this purpose. a
Having fully described iny invention, what 1. The process of producing fatty acids 'consisting in heating acidulated derivatives of aromatic bases with sulfuric acid and separating the fatty acids and the sulfates of the aromatic bases produced thereby.
and finally separating the resulting fatty acids I and sulfates of aromatic bases.
In testimony whereof I have signed this specification in the presence of two subscribing witnesses. I
' OSCAR LIEBRElCEL Witnesses:
WOLDEMAR HAUPT, HENRY HAsPEa
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18673803A US778980A (en) | 1903-12-26 | 1903-12-26 | Process of producing fatty acids. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18673803A US778980A (en) | 1903-12-26 | 1903-12-26 | Process of producing fatty acids. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US778980A true US778980A (en) | 1905-01-03 |
Family
ID=2847464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US18673803A Expired - Lifetime US778980A (en) | 1903-12-26 | 1903-12-26 | Process of producing fatty acids. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US778980A (en) |
-
1903
- 1903-12-26 US US18673803A patent/US778980A/en not_active Expired - Lifetime
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