DE556797C - Process for the preparation of oil-soluble molybdenum compounds - Google Patents
Process for the preparation of oil-soluble molybdenum compoundsInfo
- Publication number
- DE556797C DE556797C DE1930556797D DE556797DD DE556797C DE 556797 C DE556797 C DE 556797C DE 1930556797 D DE1930556797 D DE 1930556797D DE 556797D D DE556797D D DE 556797DD DE 556797 C DE556797 C DE 556797C
- Authority
- DE
- Germany
- Prior art keywords
- molybdenum
- oil
- soluble
- compounds
- oils
- 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
- 239000005078 molybdenum compound Substances 0.000 title claims description 13
- 150000002752 molybdenum compounds Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 239000003921 oil Substances 0.000 claims description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical class [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 7
- 239000011733 molybdenum Substances 0.000 claims description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 8
- -1 naphthenic acid molybdenum compounds Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000002751 molybdenum Chemical class 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- MIWHXIORWMGKTM-UHFFFAOYSA-N molybdenum;phenol Chemical class [Mo].OC1=CC=CC=C1 MIWHXIORWMGKTM-UHFFFAOYSA-N 0.000 description 2
- 125000005608 naphthenic acid group Chemical class 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 239000002641 tar oil Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Chemical class CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Chemical class CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Chemical class CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Chemical class CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Chemical class CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IJJAYRJQIJBQMK-UHFFFAOYSA-N molybdenum hydrochloride Chemical compound Cl.[Mo] IJJAYRJQIJBQMK-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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Chemical class 0.000 description 1
- 229920005989 resin Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Description
Verfahren zur Herstellung von öllöslichen Molybdänverbindungen Es ist bekannt, Molybdänoxyde als Füllmittel bei der Herstellung von Farben, Lacken u. dgl. zur Erhöhung der Deckkraft zu verwenden. Eine Lösung der Molybdänoxyde in Ölen findet dabei jedoch nicht statt.Process for the production of oil-soluble molybdenum compounds Es is known, molybdenum oxides as a filler in the manufacture of paints and varnishes and the like to increase the opacity. A solution of the molybdenum oxides in However, there is no oiling.
Es wurde ferner vorgeschlagen, Phosphormolybdänsäure in Leinöl zwecks Herstellung von Anstrichmitteln u. dgl. einzubringen, wobei ein geringer Teil der Phosphormalyb.dänsäure gelöst werden kann. In Teeren, Kohlenwasserstoffen, wie Mineralölen u. dgl., ist diese Verbindung nicht löslich.It has also been proposed to use phosphomolybdic acid in linseed oil for the purpose Manufacture of paints and the like Phosphomalybdic acid can be dissolved. In tars, hydrocarbons, such as mineral oils and the like, this compound is not soluble.
Es wurde nun gefunden, daß sich in Ölen, insbesondere Kohlenwas.serstoffen, lösliche Verbindungen des Molybdäns in einfacher Weise dadurch herstellen lassen, daß man Salze des Molybdäns zusammen mit Phenolen oder mit hochmolekularen organischen Säuren erhitzt. Geeignete Molybdänsalze für diese Reaktion sind beispielsweise die Chloride, insbesondere die durch Behandeln von Oxyden des Molybdäns (Molybdäntrioxyd oder niedrige Oxyde) mit Halogenwasserstoff bei erhöhten Temperaturen (z. B. 200 bis 3oo°) erhaltene Molybdänverbindung. Als zweite Komponente für die Herstellung der öllöslichen Molybdänverbindungen eignen sich beispielsweise Naphthensäuren, Oleinsäure, Harzsäuren usw., ferner Phenole, insbesondere Phenol selbst. Beim Erhitzen der beiden Komponenten bilden sich Molybdänverbindungen der verwendeten. Säuren bzw. Phenole und gegebenenfalls ein leicht abtrennbarer Rückstand in geringer Menge. Die so erhaltenen Molybdänverbindungen, die in der Literatur bisher nicht beschrieben, sind, enthalten gegebenenfalls noch geringe Mengen Chlor; sie lösen sich in ölen- wie Teeren, Mineralölen, Produkten der Kohle-und Ölhydrierung sowie deren Destillations-, Umwandlungs- und Raffmationsprodukten, Rückständen u. dgl., ferner- auch- in fetten Ölen, gegebenenfalls unter Erwärmuing, auf. Die Löslichkeit der Naphthensäuremolybdänverbindungen in Ölen ist größer als die der Phenolmolybdänverbindungen. Man kann die Bildung der öllöslichen Molybdänverbindungen aus den Molybdänsalzen und den organischen Säuren bzw. den Phenolen ,auch in den angegebenen Ölen u. dgl. vornehmen und den Zusatz der organischen Säuren bzw. der Phenole weglassen, wenn die Öle u. dgl. organische Säuren, z. B. Naphthensäuren, oder Phenole in nennenswerter Menge enthalten. Gegebenenfalls können letztere auch vor dem Behandeln der Öle mit Molybdänsalzen in geeigneter Menge zugefügt werden.It has now been found that oils, especially hydrocarbons, allow soluble compounds of molybdenum to be produced in a simple manner by that one salts of molybdenum together with phenols or with high molecular weight organic Acids heated. Suitable molybdenum salts for this reaction are, for example Chlorides, especially those obtained by treating oxides of molybdenum (molybdenum trioxide or low oxides) with hydrogen halide at elevated temperatures (e.g. 200 up to 300 °) obtained molybdenum compound. As a second component for manufacturing of the oil-soluble molybdenum compounds are, for example, naphthenic acids, Oleic acid, resin acids, etc., also phenols, especially phenol itself. When heated of the two components form molybdenum compounds of the used. Acids or phenols and optionally an easily separable residue in a small amount. The molybdenum compounds obtained in this way, which have not yet been described in the literature, may contain small amounts of chlorine; they dissolve in oils such as tars, mineral oils, products of coal and oil hydrogenation as well as their distillation, Conversion and refining products, residues and the like, also in fats Oiling, if necessary with heating. The solubility of the naphthenic acid molybdenum compounds in oils is greater than that of the phenol molybdenum compounds. You can get education of the oil-soluble molybdenum compounds from the molybdenum salts and the organic ones Acids or the phenols, also in the specified oils and the like Do not add organic acids or phenols if the oils and the like are organic Acids, e.g. B. contain naphthenic acids or phenols in appreciable quantities. Possibly the latter can also be used in a suitable manner before treating the oils with molybdenum salts Amount to be added.
Man kann die öllöslichen Molybdänverbindungen beispielsweise als Katalysatoren oder in der Lackindustrie verwenden. Beispiel i Durch Überleiten von trockenem Chlorwasserstoffgas über Molybdäntrioxyd bei etwa 28o° wird eine Molybdänchlorwasserstoffverbindung als Sublimat erhalten. Von dieser Verbindung werden 48 Teile in fein gepulvertem Zustande in ioo Teile gereinigte Naphthensäure unter Erhitzen auf etwa 12o° und Rühren nach und nach eingebracht. Man erhält in einer Ausbeute von etwa 85% eine Naphthensäuremolybdänverbindüng, die 14.3o% Molybdän enthält; sie ist blau gefärbt, dickflüssig bis gallertartig und, besonders in der Wärme, in Mineral- und Teerölen u. dgl. löslich. Außerdem bildet sich bei der Behandlung der Naphthensäure mit der Molybdänchlorwassersloftverbindung in geringeren Mengen ein fester Rückstand, der sich durch vorsichtiges Veraschen und Erhitzen im Chlorwasserstoffstrom wieder in die Molybdänchlorwasserstoffverbindung überführen läßt. Beispiel e Von der gemäß Beispiel i erhaltenen Molybdänchlorwasserstoffverbindung werden 58 Teile in feingepulvertem, trockenem Zustande in ioo Teile Phenol unter Erhitzen auf i 1o bis i 5o° und Rühren nach und nach ein-, gebracht. Die in einer Ausbeute von etwa 850/0 erhaltene Phenolmolybdänverbindung, die i3% Molybdän enthält, entspricht in ihrem Aussehen und in ihrem Verhalten gegenüber Ölen u. dgl. im allgemeinen der gemäß Beispiel i erhaltenen Naphthensäuremolybdänverbindung. Wurde bei ihrer Bildung ein geringer fester Rückstand erhalten, so läßt sich dieser wie in Beispiel i angegeben aufarbeiten.The oil-soluble molybdenum compounds can be used, for example, as catalysts or use in the paint industry. Example i By passing dry hydrogen chloride gas over it Over molybdenum trioxide at about 280 ° it becomes a molybdenum hydrochloric acid compound received as a sublimate. 48 parts of this compound are finely powdered Condition cleaned in 100 parts Naphthenic acid with heating about 120 ° and stirring gradually introduced. One obtains in a yield of about 85% a naphthenic acid molybdenum compound containing 14.3o% molybdenum; she is blue in color, viscous to gelatinous and, especially in the warmth, in mineral and tar oils and the like are soluble. In addition, naphthenic acid is formed during treatment a solid residue with the molybdenum chlorohydrate compound in smaller quantities, which is restored by careful ashing and heating in a stream of hydrogen chloride can be converted into the molybdenum hydrochloric acid compound. Example e From the according to Example i obtained molybdenum hydrogen chloride are 58 parts in finely powdered, dry state in 100 parts of phenol with heating to 10 to 15 ° and stirring little by little brought in. The phenol molybdenum compound obtained in a yield of about 850/0, which contains i3% molybdenum, corresponds in its appearance and in its behavior towards it Oils and the like in general of the naphthenic acid molybdenum compound obtained according to Example i. If a small solid residue was obtained when it was formed, it can be work up as indicated in example i.
Beispiel 3 Von der gemäß Beispiel i hergestellten Molybdänchlonvasserstoffverbindung werden Sog in fein zerkleinertem Zustande in ioog Stearinsäure bei 17o° nach und nach eingetragen und i/2 Stunde lang gerührt. Man. erhält etwa 1i8 g einer bei Zimmertemperatur festen, blaugefärbten Verbindung mit einem Molybdängehalt von 13,66%, die in Mineral- und Teerölen, zum Teil schon in der Kälte löslich ist. Beispiel 4 Es wird eine 6%ige Lösung von Thymol in Benzol hergestellt. Nach dem Erwärmen wird in diese Lösung etwas von der feingepulverten, gemäß Beispiel i hergestellten Molybdänchlorwasserstoffverbindung unter Rühren eingebracht, wobei sich die Flüssigkeit durch Auflösen der beschriebenen Verbindung sofort tiefblau färbt.Example 3 Of the molybdenum-chlorohydrogen compound prepared according to Example i suction in a finely crushed state in 10o stearic acid at 170 ° gradually after entered and stirred for 1/2 hour. Man. receives about 1i8 g of one at room temperature solid, blue-colored compound with a molybdenum content of 13.66%, which is found in mineral and tar oils, some of which are already soluble in the cold. Example 4 It becomes a 6% Solution made of thymol in benzene. After heating, it will be in this solution some of the finely powdered molybdenum hydrochloride compound prepared according to Example i introduced with stirring, the liquid being dissolved by dissolving the described Connection immediately turns deep blue.
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE556797T | 1930-08-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE556797C true DE556797C (en) | 1932-08-17 |
Family
ID=6564888
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1930556797D Expired DE556797C (en) | 1930-08-20 | 1930-08-20 | Process for the preparation of oil-soluble molybdenum compounds |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE556797C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3047500A (en) * | 1958-04-04 | 1962-07-31 | Sinclair Research Inc | Lubricant including a molybdenum-containing organic material |
US3202688A (en) * | 1958-04-04 | 1965-08-24 | Sinclair Research Inc | Molybdenum chloride alkylphenolates |
USRE30642E (en) | 1980-01-23 | 1981-06-09 | Halcon Research & Development Corp. | Process for preparing molybdenum acid salts |
-
1930
- 1930-08-20 DE DE1930556797D patent/DE556797C/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3047500A (en) * | 1958-04-04 | 1962-07-31 | Sinclair Research Inc | Lubricant including a molybdenum-containing organic material |
US3202688A (en) * | 1958-04-04 | 1965-08-24 | Sinclair Research Inc | Molybdenum chloride alkylphenolates |
USRE30642E (en) | 1980-01-23 | 1981-06-09 | Halcon Research & Development Corp. | Process for preparing molybdenum acid salts |
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