AT77083B - Process for the hydration of unsaturated organic acids. - Google Patents
Process for the hydration of unsaturated organic acids.Info
- Publication number
- AT77083B AT77083B AT77083DA AT77083B AT 77083 B AT77083 B AT 77083B AT 77083D A AT77083D A AT 77083DA AT 77083 B AT77083 B AT 77083B
- Authority
- AT
- Austria
- Prior art keywords
- hydration
- organic acids
- unsaturated organic
- acids
- unsaturated
- Prior art date
Links
- 230000036571 hydration Effects 0.000 title claims description 5
- 238000006703 hydration reaction Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000007524 organic acids Chemical class 0.000 title claims description 3
- 235000005985 organic acids Nutrition 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- -1 ether acids Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Verfahren zur Hydratisierung ungesättigter organischer Säuren.
Zwischen den ungesättigten Säuren einerseits und den gesättigten Oxysäntcn und dufu Derivaten, wie Äthersäuren usw. andererseits, bestehen bekanntlich enge strukturelle Beziehungen ; die Oxy- und Äthersäuren sind schematisch als Hydratationsprodukte der
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indirel. t durch intermediare Addition von Schwefelsäure und hydrolytische Spaltung der so entstehenden Schwefelsäure-Ester. Zum Beispiel im Falle der Ölsäure :
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Diese Reaktion bietet aber nur einen geringen Ersatz; sie ist kostspieliger, ergibt infolge von Nebenreaktionen sehr dunkel gefärbte Piodukte, die durch Destillation nicht gereinigt werden können, und ist schliesslich fur viele Rohstoffe der Fettindustrie, insbesondere für
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Es wurde nun ein Verfahren gefunden, nach welchem dieser Umweg vermieden und gerade die mehrfach ungesättigten Säuren durch direkte Hydratisierung in Sauerstoff- derivate der gesättigten (Oxy- und Äthersauren) verwandelt werden. Erhitzt man nämlich die Salze der ungesättigten Säuren in wässeriger Lösung bei Gegenwart einer geringen
Menge einer alkalisch reagierenden Substanz unter Druck auf 200 bis 3006, so wird von denselben direkt Wasser angelagert ; die Doppelbindungen verschwinden (die Jodzahl geht kontinuierlich zurück) und es treten Hydroxyl- und Äthergruppen auf (die Acetylzahl wächst mit dem Fortschreiten der Reaktion).
Wahrscheinlich bilden sich pritnar nur Oxy- sauren, von denen ein erheblicher Teil sekundär (unter Abspaltung von je einem Molekül
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<Desc/Clms Page number 2>
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auftretenden bedeutenden Dampfdrücke genügen, es ist aber unter Umständen vorteilhaft den Druck duehEinpressen von inerten Gasen zu erhöhen.
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Process for the hydration of unsaturated organic acids.
It is well known that there are close structural relationships between the unsaturated acids, on the one hand, and the saturated oxygens and their derivatives, such as ether acids, etc., on the other; the oxy and ether acids are shown schematically as the products of hydration
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indirel. t through the intermediate addition of sulfuric acid and hydrolytic cleavage of the sulfuric acid esters thus formed. For example in the case of oleic acid:
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This reaction offers little substitute, however; it is more expensive, gives very dark colored products as a result of side reactions, which cannot be purified by distillation, and is ultimately for many raw materials in the fat industry, especially for
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A process has now been found which avoids this detour and converts the polyunsaturated acids into oxygen derivatives of the saturated (oxy and ether acids) by direct hydration. Namely, if the salts of the unsaturated acids are heated in aqueous solution in the presence of a small amount
If the amount of an alkaline substance under pressure is 200 to 3006, water is directly attached to it; the double bonds disappear (the iodine number decreases continuously) and hydroxyl and ether groups appear (the acetyl number increases as the reaction proceeds).
Probably only oxyacids are formed, a considerable part of which is secondary (with splitting off of one molecule each)
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The significant vapor pressures that occur are sufficient, but it may be advantageous to increase the pressure by injecting inert gases.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT77083T | 1914-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT77083B true AT77083B (en) | 1919-07-10 |
Family
ID=3598707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT77083D AT77083B (en) | 1914-05-30 | 1914-05-30 | Process for the hydration of unsaturated organic acids. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT77083B (en) |
-
1914
- 1914-05-30 AT AT77083D patent/AT77083B/en active
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