DE1066577B - - Google Patents
Info
- Publication number
- DE1066577B DE1066577B DE1958P0021503 DEP0021503A DE1066577B DE 1066577 B DE1066577 B DE 1066577B DE 1958P0021503 DE1958P0021503 DE 1958P0021503 DE P0021503 A DEP0021503 A DE P0021503A DE 1066577 B DE1066577 B DE 1066577B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- castor oil
- water
- pressure vessel
- ricinic
- 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.)
- Pending
Links
- 239000004359 castor oil Substances 0.000 claims description 15
- 235000019438 castor oil Nutrition 0.000 claims description 15
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 15
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 claims description 12
- 229960003656 ricinoleic acid Drugs 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 238000007127 saponification reaction Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- JBYXPOFIGCOSSB-XBLVEGMJSA-N 9E,11E-octadecadienoic acid Chemical class CCCCCC\C=C\C=C\CCCCCCCC(O)=O JBYXPOFIGCOSSB-XBLVEGMJSA-N 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
kl. 12 ο 21kl. 12 ο 21
INTERNAT. KL. C 07 CINTERNAT. KL. C 07 C
PATENTAMTPATENT OFFICE
P 21503 IVb/12 οP 21503 IVb / 12 ο
ANMELDETAG: 9. OKTOBER 1958REGISTRATION DATE: OCTOBER 9, 1958
BEKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
AUSLEGESCHKIFT: 8. O KTO B E R 1959NOTICE
THE REGISTRATION
AND ISSUE OF THE
DISPLAY: 8 OCTOBER 1959
Es sind bisher zwei Verfahren zur Herstellung von Ricinensäure aus Ricinusöl bekannt. Bei dem einen Verfahren wird zuerst aus Ricinusöl Wasser abgespalten, wobei Ricinenöl entsteht, aus diesem erhält man dann durch Verseifung der Estergruppe die Salze der Ricinensäure, aus denen durch Behandlung mit Mineralsäure in bekannter Weise Ricinensäure erhalten werden kann.So far, two processes for the production of ricinic acid from castor oil are known. With the one In the process, water is first split off from castor oil, resulting in castor oil from which it is obtained one then by saponification of the ester group the salts of ricinenic acid, from which by treatment with Mineral acid can be obtained in a known manner ricinenic acid.
Bei dem anderen Verfahren wird zuerst das Ricinusöl verseift, und aus der entstandenen Ricinolsäure wird dann Wasser abgespalten, wobei ebenfalls die Ricinensäure entsteht.In the other process, the castor oil is saponified first, and then the ricinoleic acid formed is saponified water is then split off, which also produces ricinic acid.
Die bisher bekannten Verfahren sind also zweistufige Verfahren. Es wurde nun gefunden, daß man die Ricinensäure auch in einem Arbeitsgang herstellen kann, indem man das Ricinusöl in einem Druckgefäß in Gegenwart von Wasser, gegebenenfalls unter mechanischer Vermischung der beiden Flüssigkeiten, auf 250° C so weit erhitzt, daß sich in dem Druckgefäß ein Druck zwischen 40 und 150 atü, Vorzugsweise zwischen 40 und 70 atü, einstellt, wobei sich neben Glycerin Ricinensäure bildet.The previously known processes are therefore two-stage processes. It has now been found that one The ricinic acid can also be produced in one operation by placing the castor oil in a pressure vessel in the presence of water, if necessary with mechanical mixing of the two liquids, heated to 250 ° C. to such an extent that the pressure in the pressure vessel is between 40 and 150 atmospheres, preferably between 40 and 70 atmospheres, whereby ricinic acid is formed in addition to glycerine.
Nach dem Verfahren der Erfindung kann man also die Ricinensäure in einem Arbeitsgang aus dem Ricinusöl herstellen, wenn man dieses in Gegenwart von Wasser in einem Druckgefäß auf Temperaturen zwischen 250 und 340° C, vorzugsweise zwischen 250 und 285° C, erhitzt.According to the method of the invention, the ricinenic acid can be obtained from the in one operation Castor oil can be produced if this is brought to temperatures in the presence of water in a pressure vessel between 250 and 340 ° C, preferably between 250 and 285 ° C, heated.
Durch dieses neue Verfahren wird ein nicht zu erwartender technischer Fortschritt erzielt, denn man hätte nur erwarten können, daß die Hydrolyse des Ricinusöles in wesentlich kürzerer Zeit verläuft, daß dabei aber nur, oder zur Hauptsache, Ricinolsäure entsteht.This new procedure becomes an unexpected one Technical progress achieved, because one could only have expected that the hydrolysis of the Castor oil runs in a much shorter time, but that only, or mainly, ricinoleic acid arises.
Wird die Behandlung des Ricinusöles in einem Druckgefäß bei niederen Temperaturen durchgeführt oder unterwirft man Ricinusöl der Verseifung oder der Twitchell-Spaltung, so erhält man nur Ricinolsäure. The treatment of the castor oil is carried out in a pressure vessel at low temperatures or if castor oil is subjected to saponification or Twitchell cleavage, only ricinoleic acid is obtained.
300; g Ricinusöl mit folgenden Kennzahlen300 ; g castor oil with the following key figures
Säurezahl 6,0Acid number 6.0
Verseifungszahl 179,5Saponification Number 179.5
Jodzahl nach W ob urn 86,7Iodine number according to W ob around 86.7
Hydroxylzahl 153,4Hydroxyl number 153.4
werden in einem Druckgefäß mit 450 ecm Wasser bei 263° C, also bei 50 atü, 9 Stunden erhitzt. Nach der Entspannung trennt sich das Gemisch in zwei Schichten, deren obere zu 90,4% aus Ricinensäure und. zu 9,6% aus Nebenprodukten, besonders nicht umgesetztem Ricinusöl besteht, während die untere das Glycerin, in Wasser gelöst, enthält.are heated in a pressure vessel with 450 ecm of water at 263 ° C, i.e. at 50 atmospheres, for 9 hours. After Relaxation separates the mixture into two layers, the upper 90.4% of ricinic acid and. to 9.6% consists of by-products, especially unreacted castor oil, while the lower one is the Contains glycerine dissolved in water.
Verfahren zur Herstellung
von Ricinensäure aus RicinusölMethod of manufacture
of ricinic acid from castor oil
Anmelder:Applicant:
Pintsch Bamag Aktiengesellschaft,
Berlin NW 87, Reuchlinstr. 10-17Pintsch Bamag Aktiengesellschaft,
Berlin NW 87, Reuchlinstr. 10-17
Dr. Ernst Hügel, Hamburg-Altona,Dr. Ernst Huegel, Hamburg-Altona,
und Dr. Dietrich Spannuth, Hamburg,and Dr. Dietrich Spannuth, Hamburg,
sind als Erfinder genannt wordenhave been named as inventors
Man erhält nach der Abtrennung des Glycerins eine Fettsäure mit folgenden Kennzahlen:After the glycerine has been separated off, a fatty acid with the following key figures is obtained:
Säurezahl , 175,0Acid number, 175.0
Verseif ungszahlSaponification number
(also ein Spaltgrad von 90,4%) ... 193,5(i.e. a degree of splitting of 90.4%) ... 193.5
Jodzahl nach Woburn 146,8Woburn iodine number 146.8
Hydroxylzahl 37,5Hydroxyl number 37.5
3OO g Ricinusöl mit den im Beispiel 1 genannten Kennzahlen werden in einem Druckgefäß mit 450 ecm Wasser bei 275° C, also- 60 atü, etwa 9 Stunden erhitzt. Nach der Abtrennung des Glycerins wird eine Fettsäure in einer Ausbeute von 96,8% mit folgenden Kennzahlen erhalten:3OO g of castor oil with those mentioned in Example 1 Key figures are heated in a pressure vessel with 450 ecm of water at 275 ° C, i.e. -60 atü, for about 9 hours. After separating the glycerin, a fatty acid is obtained in a yield of 96.8% with the following Get key figures:
Säurezahl 189,7 'Acid number 189.7 '
Verseif ungszahlSaponification number
(also ein Spaltgrad von 96,8«/») . .. 195,9(ie a degree of gap of 96.8 «/»). 195.9
Jodzahl nach Woburn 149Woburn iodine number 149
Hydroxylzahl 14,5Hydroxyl number 14.5
Wie diese Beispiele, besonders Beispiel 2, zeigen, erhält man aus dem Ricinusöl nach dem Verfahren der Erfindung in der Hauptsache Ricinensäure, wie aus der hohen Jodzahl und der niedrigen Hydroxylzahl hervorgeht.As these examples, especially Example 2, show, castor oil is obtained by the process of Invention mainly ricinic acid, such as from the high iodine number and the low hydroxyl number emerges.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1958P0021503 DE1066577B (en) | 1958-10-09 | 1958-10-09 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1958P0021503 DE1066577B (en) | 1958-10-09 | 1958-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1066577B true DE1066577B (en) | 1959-10-08 |
Family
ID=592651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1958P0021503 Pending DE1066577B (en) | 1958-10-09 | 1958-10-09 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1066577B (en) |
-
1958
- 1958-10-09 DE DE1958P0021503 patent/DE1066577B/de active Pending
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