DE932668C - Process for the preparation of oxygen-containing compounds - Google Patents
Process for the preparation of oxygen-containing compoundsInfo
- Publication number
- DE932668C DE932668C DEP11802D DEP0011802D DE932668C DE 932668 C DE932668 C DE 932668C DE P11802 D DEP11802 D DE P11802D DE P0011802 D DEP0011802 D DE P0011802D DE 932668 C DE932668 C DE 932668C
- Authority
- DE
- Germany
- Prior art keywords
- oxygen
- containing compounds
- preparation
- hydrogenation
- acid number
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/06—Peroxides; Ozonides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Fats And Perfumes (AREA)
Description
Verfahren zur Herstellung von sauerstoffhaltigen Verbindungen Zusatz zum Patent 931 407 Im Patentg3I 407 ist gezeigt, daß manHydroxylverbindungen erhält, wenn man die bei der Oxydation hydroaromatischer Kohlenwasserstoffe, wie Cyclohexan, mit Sauerstoff oder Sauerstoff enthaltenden Gasen erhaltenen sauren Oxydationsrüclrstände derart einer katalytischen Hydrierung unterwirft, daß das Hydrierungserzeugnis praktisch keine Säurezahl mehr besitzt, aber noch sauerstoffhaltig ist.Process for the production of oxygen-containing compounds additive for patent 931 407 In patent g3I 407 it is shown that hydroxyl compounds are obtained if the oxidation of hydroaromatic hydrocarbons, such as cyclohexane, acidic oxidation residues obtained with oxygen or gases containing oxygen subjected to catalytic hydrogenation such that the hydrogenation product is practical no longer has an acid number, but still contains oxygen.
Es wurde nun gefunden, daß man bei der erwähnten Behandlung andere wertvolle sauerstoffhaltige Verbindungen erhält, wenn man die Hydrierung schon abbricht, sobald die Säurezahl erheblich zurückgegangen ist, das Hydrierungserzeugnis jedoch noch eine verhältnismäßig hohe Esterzahl aufweist. Die so erhaltenen Ilydrierungserzeugnisse sind gelbe bis leicht braun gefärbte, in Wasser unlösliche Verbindungen, die nur zum Teil unzersetzt destillierbar sind und Gemische esterartiger Verbindungen, die außerdem freie Hydroxyl- und Carboxylgruppen enthalten, darstellen. Diese Verbindungen können für sich oder nach Veresterung der freien Carboxylgruppen mit ein- oder mehrwertigen Alkoholen z. B. als Weichmachungsmittel oder hochwertige Schmiermittel Verwendung finden. It has now been found that the treatment mentioned different valuable oxygen-containing compounds are obtained if the hydrogenation is interrupted, however, once the acid number has decreased significantly, so does the hydrogenation product still has a relatively high ester number. The Ilydration products thus obtained are yellow to light brown colored, water-insoluble compounds that only are partially distillable without decomposition and mixtures of ester-like compounds that also contain free hydroxyl and carboxyl groups represent. These connections can by themselves or after esterification of the free carboxyl groups with mono- or polyvalent ones Alcohols e.g. B. as a plasticizer or high-quality lubricant use Find.
Für die bei dem Verfahren einzuhaltenden Bedingungen gilt sinngemäß das im Hauptpatent Gesagte. The same applies to the conditions to be complied with during the procedure what was said in the main patent.
Beispiel Ein Oxydationserzeugnis, das aus Cyclohexan durch Oxydation mit Luft bei I500 und 10 atü Druck unter solchen Bedingungen erhalten wurde, daß I5 % des eingesetzten Cyclohexans umgesetzt wurden, wird durch die Destillation unter gewöhnlichem Druck von nicht umgesetztem Cyclohexan und vom Reaktionswasser, sodann durch Vakuumdestillation bis 600 bei I7 mm Hg vom entstandenen Cyclohexanol und Cyclohexanon und schließlich durch Filtration von der entstandenen Adipinsäure befreit. Man erhält einen dunklen, viskosen, in Wasser unlöslich sauren Oxydationsrückstand mit folgenden Kennzahlen: Säurezahl . I75 Verseifungszahl ..... 602 Hydroxylzahl ....... 95. Example An oxidized product obtained from cyclohexane by oxidation with air at I500 and 10 atm Pressure obtained under such conditions was that 15% of the cyclohexane used have been converted, is due to the distillation under normal pressure of unreacted cyclohexane and of the water of reaction, then by vacuum distillation to 600 at 17 mm Hg of the resulting cyclohexanol and cyclohexanone and finally by filtration of the adipic acid formed freed. A dark, viscous, acidic oxidation residue which is insoluble in water is obtained with the following key figures: acid number. I75 saponification number ..... 602 hydroxyl number ....... 95.
Man leitet diesen sauren Oxydationsrückstand bei etwa 280° unter 300 atü Wasserstoffdruck über einen auf Bimsstein niedergeschlagenen, mit Chrom aktivierten Kupferkatalysator mit einer Belastung von stündlich 2 l je Liter Kontaktraum. Man erhält ein aus zwei Schichten bestehendes Erzeugnis . die eine Schicht ist Reaktionswasser, die andere, ölige, hat folgende Kennzahlen: Säurezahl , 3 I3' Verseifungszahl ..... 239 Hydroxylzahl ....... 246. This acidic oxidation residue is passed under at about 280 ° 300 atmospheres of hydrogen pressure on a pumice stone with chrome activated copper catalyst with an hourly load of 2 l per liter of contact space. A product consisting of two layers is obtained. one layer is reaction water, the other, oily one, has the following key figures: acid number, 3 I3 'saponification number ..... 239 hydroxyl number ....... 246.
Beim Erhitzen von je 100 Gewichtsteilen der öligen Schicht mit 2 Gewichtsteilen Glycerin unter Einleiten von Stickstoff auf I8o0 erhält man ein Estergemisch mit der Säurezahl 2. When heating 100 parts by weight of the oily layer with 2 Parts by weight of glycerol with the introduction of nitrogen to 180 gives an ester mixture with the acid number 2.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP11802D DE932668C (en) | 1945-02-21 | 1945-02-21 | Process for the preparation of oxygen-containing compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP11802D DE932668C (en) | 1945-02-21 | 1945-02-21 | Process for the preparation of oxygen-containing compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
DE932668C true DE932668C (en) | 1955-09-05 |
Family
ID=7363689
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP11802D Expired DE932668C (en) | 1945-02-21 | 1945-02-21 | Process for the preparation of oxygen-containing compounds |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE932668C (en) |
-
1945
- 1945-02-21 DE DEP11802D patent/DE932668C/en not_active Expired
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