DE1058041B - Process for the purification of low molecular weight saturated fatty acids - Google Patents
Process for the purification of low molecular weight saturated fatty acidsInfo
- Publication number
- DE1058041B DE1058041B DEF25198A DEF0025198A DE1058041B DE 1058041 B DE1058041 B DE 1058041B DE F25198 A DEF25198 A DE F25198A DE F0025198 A DEF0025198 A DE F0025198A DE 1058041 B DE1058041 B DE 1058041B
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- low molecular
- purification
- fatty acids
- saturated 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 235000003441 saturated fatty acids Nutrition 0.000 title claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 title claims description 4
- 238000000746 purification Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 10
- 239000012286 potassium permanganate Substances 0.000 claims description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
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
Verfahren zur Reinigung von niedermolekularen gesättigten Fettsäuren Bei der Herstellung niedermolekularer gesättigter Fettsäuren durch Oxydation der entsprechenden Aldehyde mit Sauerstoff erhält man Gemische, die außer der Säure und dem nicht umgesetzten Aldehyd mehr oder weniger gefärbte Verunreinigungen enthalten, die durch Destillieren nicht zu entfernen sind. Weiterhin verursachen sie intensive Färbungen, wenn die isolierte Carbonsäure mit starken Mineralsäuren, wie konzentrierter Schwefelsäure oder hochprozentiger Perchlorsäure, gemischt werden, wie dies z. B. bei Veresterungen, etwa von Cellulose, notwendig ist. Process for the purification of low molecular weight saturated fatty acids In the production of low molecular weight saturated fatty acids by oxidation of the corresponding aldehydes with oxygen one obtains mixtures which apart from the acid and the unreacted aldehyde contain more or less colored impurities, which cannot be removed by distillation. Furthermore, they cause intense Colorations when the isolated carboxylic acid is concentrated with strong mineral acids, such as Sulfuric acid or high percentage perchloric acid, are mixed, as z. B. is necessary in the case of esterifications, for example of cellulose.
Es hat nicht an Versuchen gefehlt, diese Nebenprodukte zu beseitigen, so z. B. durch mehrstündiges Erhitzen der Rohsäuren auf 80 bis 1500 C mit Sauerstoff in Gegenwart von Oxydationskatalysatoren (britische Patentschrift 448145) oder durch Behandeln mit Kaliumpermanganat, Salpetersäure oder Wasserstoffperoxyd (USA.-Patentschrift 2 225 421). There has been no lack of attempts to eliminate these by-products, so z. B. by heating the crude acids to 80 to 1500 C with oxygen for several hours in the presence of oxidation catalysts (British patent 448145) or by Treatment with potassium permanganate, nitric acid or hydrogen peroxide (USA.Patent 2 225 421).
Auf diese Weise kann jedoch nicht erreicht werden, daß beim Mischen der Carbonsäuren, z. B. mit konzentrierter Schwefelsäure, keine Färbungen mehr auftreten. Mit Salpetersäure behandelte Carbonsäuren enthalten außerdem noch kaum zu entfernende stickstoffhaltige Verunreinigungen. In this way, however, it cannot be achieved that when mixing the carboxylic acids, e.g. B. with concentrated sulfuric acid, no more colorations occur. In addition, carboxylic acids treated with nitric acid contain hardly any carboxylic acids that can be removed nitrogenous impurities.
Es wurde nun gefunden, daß man die farbigen bzw. farbgebenden Verunreinigungen dadurch praktisch völlig beseitigen kann, daß man das Oxydationsprodukt nach Abtrennen des nicht umgesetzten Aldehyds zunächst mit Hydrazin oder Hydrazinhydrat und danach mit wässeriger Kaliumpermanganatlösung behandelt und dann fraktioniert destilliert. It has now been found that the colored or coloring impurities can be removed can thereby be practically completely eliminated by separating the oxidation product of the unreacted aldehyde first with hydrazine or hydrazine hydrate and then treated with aqueous potassium permanganate solution and then fractionally distilled.
Besonders reine Säuren erhält man, wenn man die mit Hydrazinhydrat versetzten Rohsäuren vor der nachfolgenden Behandlung mit Kaliumpermanganatlösung destilliert. Particularly pure acids are obtained if you use those with hydrazine hydrate added crude acids before the subsequent treatment with potassium permanganate solution distilled.
Nach diesem Verfahren gelingt es leicht, Carbonsäuren herzustellen, die farblos sind und sich auch beim Mischen mit konzentrierter Schwefelsäure im Verhältnis 1:1 nicht verfärben. Es entstehen auch keine stickstoffhaltigen Produkte, die die Säuren verunreinigen. With this process it is easy to produce carboxylic acids, which are colorless and even when mixed with concentrated sulfuric acid in the 1: 1 ratio does not discolor. There are also no nitrogen-containing products, which contaminate the acids.
Die Mengen an Hydrazinhydrat und Kaliumpermanganat, die zur Reinigung erforderlich sind, richten sich nach der Menge der Nebenprodukte. Ein Zusatz in der Höhe von jeweils etwa 0,1 bis etwa 0,5 O/o, berechnet auf die Rohsäure, reicht in fast allen Fällen aus, um eine gute Wirkung zu erzielen. The amounts of hydrazine hydrate and potassium permanganate necessary for cleaning required depend on the amount of by-products. An addition in the amount in each case from about 0.1 to about 0.5%, calculated on the raw acid, ranges in almost all cases in order to achieve a good effect.
Beispiel 1 Ein durch Oxydieren von Acetaldehyd mit Sauerstoff in Gegenwart von 0,10/o Manganacetat hergestelltes Oxydationsgemisch wird von nicht umgesetztem Aldehyd durch Destillation befreit, mit 10/o Hydrazinhydrat versetzt und destilliert. Das Destillat wird mit 10/b Kaliumpermanganat in Form einer konzentrierten wässerigen Lösung gemischt und nochmals destilliert. Die Essigsäure, die als Destillat anfällt, ist farblos und zeigt beim Mischen mit konzentrierter Schwefelsäure keine Farbreaktionen. Example 1 A by oxidizing acetaldehyde with oxygen in The presence of 0.10 / o manganese acetate produced oxidation mixture is not freed converted aldehyde by distillation, treated with 10 / o hydrazine hydrate and distilled. The distillate is concentrated with 10 / b potassium permanganate in the form of a aqueous solution mixed and distilled again. The acetic acid used as a distillate is colorless and does not show any when mixed with concentrated sulfuric acid Color reactions.
Beispiel 2 Rohe Propionsäure, die durch Oxydieren von Propionaldehyd mit Sauerstoff und anschließendes Abtrennen der leicht siedenden Produkte hergestellt wurde, wird wie im Beispiel 1 mit Hydrazinhydrat und Kaliumpermanganatlösung behandelt. Die Säure ist nach der Behandlung nicht gefärbt und gibt beim Mischen mit konzentrierter Schwefelsäure keine Farbreaktion. Example 2 Crude propionic acid obtained by oxidizing propionaldehyde with oxygen and subsequent separation of the low-boiling products is treated as in Example 1 with hydrazine hydrate and potassium permanganate solution. The acid is not colored after treatment and gives when mixed with concentrated Sulfuric acid no color reaction.
Beispiel 3 Ein durch Oxydieren von Butyraldehyd mit Sauerstoff hergestelltes Oxydationsgemisch wird durch Destillieren von niedrigsiedenden Bestandteilen befreit, mit 0,50:a Hydrazinhydrat gemischt und destilliert. Das Destillat wird mit 0,50/0 Kaliumpermanganat in Form einer konzentrierten wässerigen Lösung gemischt. Bei der destillativen Aufarbeitung fällt eine farblose Buttersäure an, die sich beim Versetzen mit konzentrierter Schwefelsäure nicht verfärbt. Example 3 One made by oxidizing butyraldehyde with oxygen Oxidation mixture is freed from low-boiling components by distillation, mixed with 0.50: a hydrazine hydrate and distilled. The distillate is 0.50 / 0 Potassium permanganate mixed in the form of a concentrated aqueous solution. In the Work-up by distillation results in a colorless butyric acid, which dissolves when it is added not discolored with concentrated sulfuric acid.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25198A DE1058041B (en) | 1958-03-07 | 1958-03-07 | Process for the purification of low molecular weight saturated fatty acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25198A DE1058041B (en) | 1958-03-07 | 1958-03-07 | Process for the purification of low molecular weight saturated fatty acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1058041B true DE1058041B (en) | 1959-05-27 |
Family
ID=7091527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF25198A Pending DE1058041B (en) | 1958-03-07 | 1958-03-07 | Process for the purification of low molecular weight saturated fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1058041B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0487284A3 (en) * | 1990-11-19 | 1993-01-07 | Hoechst Celanese Corporation | Removal of carbonyl impurities from a carbonylation process stream |
-
1958
- 1958-03-07 DE DEF25198A patent/DE1058041B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0487284A3 (en) * | 1990-11-19 | 1993-01-07 | Hoechst Celanese Corporation | Removal of carbonyl impurities from a carbonylation process stream |
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