DE732957C - Process for the production of high molecular weight waxy substances - Google Patents
Process for the production of high molecular weight waxy substancesInfo
- Publication number
- DE732957C DE732957C DEI62522D DEI0062522D DE732957C DE 732957 C DE732957 C DE 732957C DE I62522 D DEI62522 D DE I62522D DE I0062522 D DEI0062522 D DE I0062522D DE 732957 C DE732957 C DE 732957C
- Authority
- DE
- Germany
- Prior art keywords
- substances
- production
- molecular weight
- high molecular
- catalysts
- 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
- 239000000126 substance Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- -1 aliphatic alcohols Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G73/00—Recovery or refining of mineral waxes, e.g. montan wax
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Verfahren zur Herstellung hochmolekularer wachsartiger Stoffe Es ist bekannt, freie oder veresterte Carboxylgruppen enthaltende aliphatische Verbindungen in Gegenwart vorn Katalysatoren, die kohlendioxydabspaltend wirken, auf höhere Temperaturen zu erhitzen, die Ausgangs.stoffe auf diese Weise in Ketone überzuführen und diese anschließend zu reduzieren, z. B. durch Behandeln mit Wasserstoff unter Druck in Gegenwart von Hydrierungskatalysatoren. Dabei wurden als Ausgangsstoffe u. a.auch Stoffe verwendet, die durch Oxydation von Paraffinkohlen«vasserstoffen, Fetten, fetten Ölen, Fettsäuren oder Pechen erhalten wurden.Process for the production of high molecular weight waxy substances It is known aliphatic compounds containing free or esterified carboxyl groups in the presence of catalysts that split off carbon dioxide at higher temperatures to heat, to convert the starting materials in this way into ketones and these then reduce, e.g. B. by treating with hydrogen under pressure in Presence of hydrogenation catalysts. The starting materials also included Substances are used which are hydrogenated by the oxidation of paraffin carbons, fats, fatty oils, fatty acids or pitches were obtained.
Die so gewonnenen Erzeugnisse haben wie die Wachse allgemein die Eigenschaft, beim Überschreiten des Schmelzpunkts ihre Zähigkeit sprunghaft zu ändern, derart, daß sie sich noch wenige Gnade unterhalb des Schmelzpunkts in festem, wenn auch zum Teil weichem oder knetbarem Zustand befinden, wenige Grade oberhalb des Schmelzpunkts aber bereits leichtflüssig sind.The products obtained in this way, like waxes in general, have the property to change their toughness abruptly when the melting point is exceeded, in such a way, that they are still a few grace below the melting point in solid, though partly in a soft or kneadable state, a few degrees above the melting point but are already fluid.
Es wurde nun gefunden, daß man wachsartige E.rzeqgn:iss,e, deren Zähigkeit sich in der Nähe des Schmelzpunkts nur sehr wen g ändert, herstellen kann, wenn man die Rückstände, die man bei der Destillation von Fettsäuren erhält, mit Oxydationsmitteln behandelt, aus den Oxydationserzeugnissen durch Erhitzen mit Katalysatoren Kohlendioxyd abspaltet und die dabei entstehenden Ketone hydriert. Als Ausgangsstoffe können alle bei der Destillation natürlicher oder künstlich hergestellter Fettsäuren verbleibenden Rückstände dienen, wobei die Destillation unter gewöhnlichem oder vermindertem Druck, gegebenenfalls unter Verwendung von trägen Gasen oder Dä@mpfen,aausgeführt werden kann. Die Oxydation dieser Destillationsrückstände kann nach den Verfahren der Patente 405 850, 566 450 oder 579 988 ausgeführt werden. Die katalytische Behandlung der Oxydationserzeugnisse kann man so vornehmen, daß man sie auf Temperaturen oberhalb zoo° unter Zusatz von Katalysatoren erhitzt. Als Katalysatoren kümmen z. B. Nickel, Eisen, Mangan, Wolfrainsulfid oder Aluminiumoxyd oder deren Gemische in Betracht. Oft ist es vorteilhaft, sie aufTrägerstoffe, wieKieselgur, Kieselgel oder Bleicherde, aufzubringen. Die so erhaltenen, im wesentlichen aus hochmolekularen Ketonen bestehenden Stoffe werden, gegebenenfalls nach vorheri@geT Reinigung und Abtrennung der Katalysatoren, hydriert. Dies kann auf katalytischem Wege mit M'ass.erstoff und Katalysatoren, wie Nickel oder Kobalt, oder mit Natrium und Alkohol oder anderen reduzierend wirkenden chemischen Stoffen bewirkt werden. Bei der Hydrierung wird gleichzeitig eine weitgehende Reinigung erzielt, so daß aus den zum Teil braun und schwarz 6 e-, färbten Ausgangsstoffen helle, gelbe und Vt sogar farblose Endstoffe erhalten werden. Die -Hydrierung kann man zu den sekundären Alkoholen oder bis zur völligen Reduktion zu Kohlenwasserstoffen führen.It has now been found that waxy E.rzeqgn: iss, e, the viscosity of which changes only slightly near the melting point, can be produced if the residues obtained from the distillation of fatty acids are treated with oxidizing agents , carbon dioxide is split off from the oxidation products by heating with catalysts and the resulting ketones are hydrogenated. All residues remaining during the distillation of natural or artificially produced fatty acids can serve as starting materials, it being possible for the distillation to be carried out under normal or reduced pressure, if necessary using inert gases or vapors. The oxidation of these still bottoms can be carried out according to the procedures of patents 405,850 , 566,450 or 579,988. The catalytic treatment of the oxidation products can be carried out in such a way that they are heated to temperatures above zoo ° with the addition of catalysts. As catalysts z. B. nickel, iron, manganese, Wolfrainsulfid or aluminum oxide or mixtures thereof into consideration. It is often advantageous to apply them to substrates such as diatomaceous earth, silica gel or fuller's earth. The substances thus obtained, consisting essentially of high molecular weight ketones, are hydrogenated, if necessary after previous purification and separation of the catalysts. This can be achieved catalytically with hydrogen and catalysts such as nickel or cobalt, or with sodium and alcohol or other reducing chemical substances. During the hydrogenation, a high degree of purification is achieved at the same time, so that light, yellow and even colorless end materials are obtained from the starting materials, some of which are brown and black. Hydrogenation can lead to secondary alcohols or to complete reduction to hydrocarbons.
Die neuen Erzeugnisse zeigen im Gegensatz zu den Wachsen oder wachsartigen Stoffen keinen scharfen Schmelzpunkt, sondern gehen innerhalb eines größeren Temperaturbereichs vom festen in .einen zähflüssigen Zustand über und behalten diesen Zustand noch his 2o bis 30' oberhalb des Erweichungspunkts bei. Sie können mit Vorteil für die verschiedensten Zwecke der wachsverarbeitenden Gewerbe ,angewandt «-erden, und zwar wegen der erwähnten geringen Zähigkeitsänderung in der Gegend des Schmelzpunkts gut als Vergußmassen.The new products show in contrast to the waxes or waxy Substances do not have a sharp melting point, but go within a larger temperature range from a solid to a viscous state and still retain this state his 2o to 30 'above the softening point. You can take advantage of that various purposes of the wax-processing industry, applied "-grounds, namely because of the mentioned small change in toughness in the area of the melting point good as casting compounds.
Die in dem folgenden Beispiel angegebenen Teile sind Gewichtsteile.The parts given in the following example are parts by weight.
Beispiel Bei der Destillation von I'ranfettsäuTen auf die in der Patentschrift 397 332 beschriebene Weise erhaltene Rückstände werden mit Salpetersäure oxydiert. 65o Teile des rohen, dunklen Oxydationserzeugnisses mit den Kennzahlen: Säurezahl 532, Verseifungszahl 602, Schmelzpunkt 70°, werden mit ioo Teilen Eisenpulver 8 Stunden lang auf 29o' erhitzt. Das schwarze, harte Ketongemisch, das folgende Kennzahlen hat: Säurezahl ,¢,2, Verseifungszahl 21, Schmelzpunkt ioo', wird mit 130/0 eines Nickel-Kieselgur-Katalysators bei 300° und Zoo Atm. Wasserstoffdruck io Stunden lang hydriert. Man erhält so ein braunes, wachsähnliches Erzeugnis mit nachstehenden Kennzahlen: Säurezahl 1,4, Verseif ungszali14,2, Schmelzbereich etwa 95 bis io2°. Es ist noch bei 130' sehr zähflüssig und eignet sich vorzüglich als Vergußmasse.EXAMPLE Residues obtained in the distillation of fatty acids in the manner described in patent specification 397 332 are oxidized with nitric acid. 65o parts of the raw, dark oxidation product with the codes: acid number 532, saponification number 602, melting point 70 °, are heated to 29 ° for 8 hours with 100 parts of iron powder. The black, hard ketone mixture, which has the following key figures: acid number, ¢, 2, saponification number 21, melting point 100 ', is treated with 130/0 of a nickel-kieselguhr catalyst at 300 ° and zoo atm. Hydrogenated under hydrogen pressure for 10 hours. This gives a brown, wax-like product with the following key figures: acid number 1.4, saponification rate 14.2, melting range about 95 to 10 °. It is still very viscous at 130 ' and is ideally suited as a potting compound.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI62522D DE732957C (en) | 1935-06-19 | 1935-06-19 | Process for the production of high molecular weight waxy substances |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI62522D DE732957C (en) | 1935-06-19 | 1935-06-19 | Process for the production of high molecular weight waxy substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE732957C true DE732957C (en) | 1943-03-19 |
Family
ID=7195704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI62522D Expired DE732957C (en) | 1935-06-19 | 1935-06-19 | Process for the production of high molecular weight waxy substances |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE732957C (en) |
-
1935
- 1935-06-19 DE DEI62522D patent/DE732957C/en not_active Expired
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