DE3340711A1 - Process for the preparation of paraffinic hydrocarbon solvents from vegetable oils - Google Patents
Process for the preparation of paraffinic hydrocarbon solvents from vegetable oilsInfo
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- DE3340711A1 DE3340711A1 DE19833340711 DE3340711A DE3340711A1 DE 3340711 A1 DE3340711 A1 DE 3340711A1 DE 19833340711 DE19833340711 DE 19833340711 DE 3340711 A DE3340711 A DE 3340711A DE 3340711 A1 DE3340711 A1 DE 3340711A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
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- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/45—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
- C10G3/46—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof in combination with chromium, molybdenum, tungsten metals or compounds thereof
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- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
- C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
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- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/54—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids characterised by the catalytic bed
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/85—Chromium, molybdenum or tungsten
- C07C2523/88—Molybdenum
- C07C2523/882—Molybdenum and cobalt
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/85—Chromium, molybdenum or tungsten
- C07C2523/88—Molybdenum
- C07C2523/883—Molybdenum and nickel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- C07C2529/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
- C07C2529/14—Iron group metals or copper
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- C07C2529/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
- C10G2300/1014—Biomass of vegetal origin
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- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4018—Spatial velocity, e.g. LHSV, WHSV
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Beschreibung description
Die vorliegende Erfindung betrifft allgemein ein Verfahren zur Herstellung von Paraffin-Kohlenwasserstoffen aus aus pflanzlichen ollen.The present invention relates generally to a method of manufacture of paraffin hydrocarbons from vegetable oils.
Paraffinische Kohlenwasserstoffe, die auch als Alkane bezeichnet werden, sind Verbindungen aus Wasserstoff und Kohlenstoff, die Strukturen haben, in denen das Kohlenstoffatom nur einfache Valenzbindungen bildet und die in offenen Ketten angeordnet sind, die gerade oder verzweigt sein können. Das Verhältnis von Kohlenstoffatomen zu Wasserstoffatomen in allen paraffinischen Kohlenwasserstoffen kann ausgedrückt werden durch die allgemeine Formel CnH2n+2 Paraffinische Kohlenwasserstoffe sind charakterisiert im allgemeinen durch ein Fehlen von auffälliger chemischer Reaktivität ebenso wie durch das niedrigste spezifische Gewicht der flüssigen Kohlenwasserstoffe (der Bereich geht von etwa 0,62 bis 0,77). Paraffinische Kohlenwasserstoffe kommen in Erdöl und Erdgas vor und können getrennt werden von Erdöl durch fraktionierte Destillation. Van Nostrand's Scientific Encyclopedia, 5th Ed., S. 1294-1299. Die physikalischen Eigenschaften paraffinischer Kohlenwasserstoffe machen diese Verbindungen gut geeignet zum Gebrauch als organische Lösungsmittel. Im Hinblick auf die erschöpfbare Natur des natürlichen Erdöls und seiner augenblicklich stark unbeständigen Kosten, ebenso wie auf die Tatsache, daß bestimmte Regionen und Länder sehr kleine oder minimale Quantitäten an natürlichem Erdölhaben, besteht ein Bedarf für ein Verfahren, das wirtschaftlich paraffinische Kohlenwasserstoffe aus alternativen Quellen von Rohmaterial herstellen kann. Ein derartiges Verfahren muß wirtschaftlich paraffinische Kohlenwasserstoffe aus Rohmaterialien produzieren, die sowohl leicht zugänglich oder ersetzbar als auch nicht unerschwinglich teuer sind.Paraffinic hydrocarbons, also known as alkanes, are compounds of hydrogen and carbon that have structures in which the carbon atom only forms simple valence bonds and those in open chains are arranged, which can be straight or branched. The ratio of carbon atoms to hydrogen atoms in all paraffinic hydrocarbons can be expressed are given by the general formula CnH2n + 2 are paraffinic hydrocarbons generally characterized by a lack of noticeable chemical reactivity as well as the lowest specific weight of the liquid hydrocarbons (the range is from about 0.62 to 0.77). Paraffinic hydrocarbons come in petroleum and natural gas and can be separated from petroleum by fractional Distillation. Van Nostrand's Scientific Encyclopedia, 5th Ed., Pp. 1294-1299. the physical properties of paraffinic hydrocarbons make these compounds well suited for use as an organic solvent. In terms of the exhaustible The nature of natural petroleum and its currently highly volatile cost, as well as the fact that certain regions and countries are very small or minimal Having quantities of natural petroleum there is a need for a process that economically produces alternative paraffinic hydrocarbons Can produce sources of raw material. Such a process must be economical produce paraffinic hydrocarbons from raw materials that are both easily accessible or replaceable as well as not prohibitively expensive.
In der vorliegenden Erfindung werden paraffinische Kohlenwasserstoffe hergestellt aus höheren Fettsäure-Glycerinestern in einem katalytischen Crack-prozess, wobei Y-Zeolith, Kobalt-Molybdän oder Nickel-Molybdän zusammen mit Aluminiumoxid verwendet wird.In the present invention, paraffinic hydrocarbons are used made from higher fatty acid glycerol esters in a catalytic cracking process, where Y-zeolite, cobalt-molybdenum or nickel-molybdenum together with aluminum oxide is used.
Im Verfahren der vorliegenden Erfindung sind entweder gesättigte oder ungesättigte Fettsäuren ausreichend als Rohmaterial. Deshalb ist eine Hydrierung nicht erforderlich. Ein gesättigter Fettsäureglycerinester kann erhalten werden aus biologischen Quellen, wie Kokosnußöl und ein ungesättigter Fettsäureglycerinester kann erhalten werden aus biologischen Quellen wie einem medizinischen Nußöl (physic nut oil). Während man solche erneuerbaren Quellen verwendet, kann eine Versorgung von paraffinischen Kohlenwasserstoffen hergestellt werden in Ländern, die keine natürlichen Erdöllagerstätten haben. Weiterhin ist gemäß dem Verfahren der vorliegenden Erfindung das Rohmaterial, das erforderlich ist um paraffinische Kohlenwasserstoffe zu produzieren, nicht eine nicht erneuerbare Quelle, die mit der Zeit erschöpft wird. Deshalb ist es die erste Aufgabe der vorliegenden Erfindung, paraffinische Kohlenwasserstoffe aus biologischen Materialien herzustellen.In the process of the present invention are either saturated or unsaturated fatty acids sufficient as raw material. That is why there is a hydrogenation not mandatory. A saturated fatty acid glycerol ester can be obtained from biological sources such as coconut oil and an unsaturated fatty acid glycerol ester can be obtained from biological sources such as a medicinal nut oil (physic nut oil). While using such renewable sources, one can supply of paraffinic hydrocarbons are produced in countries that do not have any have natural oil deposits. Furthermore, according to the method of the present Invention of the raw material required to produce paraffinic hydrocarbons to produce, not a non-renewable source that depletes over time will. Therefore, it is the first object of the present invention to make paraffinic Manufacture hydrocarbons from biological materials.
Diese und weitere Aufgaben und Vorteile der vorliegenden Erfindung werden offensichtlich für Fachleute in Verbindung mit der folgenden Beschreibung der bevor zu ten Ausführungsform.These and other objects and advantages of the present invention will become apparent to those skilled in the art in connection with the following description the before to th embodiment.
In der bevorzugten Ausführungsform eines Verfahrens in Ubereinstimmung mit der vorliegenden Erfindung wird ein Glycerinester einer höheren Fettsäure katalytisch gecrackt durch einen Katalysator, in dem der Träger Aluminiumoxid ist, das Aluminiumsilikat-Y-Zeolith in Kristallform oder Kobalt-Molybdän oder Nickel-Molybdän enthält. Der Gehalt des Katalysators an Aluminosilikat-Y-Zeolith sollte zwischen annäherungsweise 5 und 50 Gew.-% betragen, wobei der Bereich von 10 bis etwa 30 Gew.-% bevorzugt ist. Der Kobaltgehalt des Katalysators sollte zwischen annähernd 3 bis 10 Gew.-% liegen, wobei der Bereich von 4 bis etwa 6 Gew.-% bevorzugt ist. Der Nickelgehalt des Katalysators sollte zwischen etwa 3 und 10 Gew.-% liegen, wobei der Bereich von etwa 4 bis 6 Gew.-% bevorzugt ist. Der Molybdängehalt des Katalysators sollte zwischen etwa 10 und 20 Gew.-% liegen, wobei der Bereich von etwa 13 bis 18 Gew.-% bevorzugt ist.In the preferred embodiment of a method in accordance with the present invention, a glycerol ester of a higher fatty acid becomes catalytic cracked by a catalyst in which the support is aluminum oxide, the aluminum silicate Y zeolite in crystal form or contains cobalt-molybdenum or nickel-molybdenum. The content of the The aluminosilicate Y zeolite catalyst should be between approximately 5 and 50% by weight, with the range from 10 to about 30% by weight being preferred. Of the The cobalt content of the catalyst should be between approximately 3 to 10% by weight, with the range from 4 to about 6 weight percent being preferred. The nickel content of the catalyst should be between about 3 and 10% by weight, with the range from about 4 to 6 % By weight is preferred. The molybdenum content of the catalyst should be between about 10 and 20% by weight, with the range of about 13 to 18% by weight being preferred.
Während des Verfahrens der vorliegenden Erfindung sollte der Reaktionsdruck, der in dem Reaktor angewendet wird, der hauptsächlich durch Wasserstoff angewendet wird, zwischen etwa 9,8 und 196 bar (10 und 200 kg/cm2) liegen, wobei der Bereich von etwa 29,4 bis 147 bar (30 bis 150 kg/cm2) bevorzugt ist. Die Reaktionstemperatur des Reaktors sollte zwischen etwa 30000 und 6000C, vorzugsweise zwischen 350 und 4500C liegen.During the process of the present invention, the reaction pressure, which is used in the reactor which is mainly used by hydrogen will be between about 9.8 and 196 bar (10 and 200 kg / cm2), the range being from about 29.4 to 147 bar (30 to 150 kg / cm2) is preferred. The reaction temperature of the reactor should be between about 30,000 and 6000C, preferably between 350 and 4500C.
Die Erfindung wird an einigen Beispielen ausgeführt.The invention is carried out using a few examples.
Das ölprodukt in den folgenden Beispielen wurde gesammelt bei einer Temperatur von bis zu 330"C und das Produkt wurde analysiert durch Gaschromatographie.The oil product in the following examples was collected at a Temperature up to 330 "C and the product was analyzed by gas chromatography.
Beispiel l In diesem Beispiel, das in Tabelle 1 aufgezeichnet ist, werden paraffinische Kohlenwasserstoffe produziert aus Kokosnußöl, das gesättigte Fettsäureglycerinester zu etwa 91 Gew.-% und ungesättigte Fettsäureglycerinester zu etwa 8 Gew.-% enthält. Der Siedepunkt des Rohmaterials war etwa 2900C bis 552"C. Das katalytische Cracken wurde durchgeführt innerhalb eines Festbettreaktors, in der der Reaktionsdruck etwa 147 bar (150 kg/cm2) betrug mit einer Wasserstoff-Fluß rate von 1200 ml H2 pro ml Beschickungsmaterial. Die Reaktionstemperatur wurde zwischen etwa 400"C und 410"C gehalten und die l.h.s.v. (stündliche Flüssigkeitsraumgeschwindigkeit) wurde bei etwa 0,3 pro Stunde gehalten. Der Katalysator, der in dem ersten Beispiel verwendet wurde, war Y-Zeolith-Aluminiumoxid und die Ausbeute an paraffinischen Wasserstoffen war 58,4 Gew.-% mit anderen Kohlenwasserstoffen, die etwa 1,5 Gew.-% des Produktes umfaßten. Die paraffinischen Kohlenwasserstoffe, die erhalten wurden, hatten Kohlenstoffzahlen zwischen 4 und 19.Example l In this example recorded in Table 1, Paraffinic hydrocarbons are produced from coconut oil, the saturated one Fatty acid glycerol esters to about 91% by weight and unsaturated fatty acid glycerol esters contains about 8 wt .-%. The boiling point of the raw material was about 2900C to 552 "C. The catalytic cracking was carried out inside a fixed bed reactor, in the reaction pressure was about 147 bar (150 kg / cm2) with a hydrogen flow rate of 1200 ml H2 per ml feed material. The reaction temperature was between held around 400 "C and 410" C and the l.h.s.v. (liquid hourly space velocity) was held at about 0.3 per hour. The catalyst used in the first example was used, Y-zeolite-alumina and the yield was paraffinic Hydrogen was 58.4 wt% with other hydrocarbons being about 1.5 wt% of the product included. The paraffinic hydrocarbons that were obtained had carbon numbers between 4 and 19.
B e i s p i e 1 II In diesem Beispiel war der verwendete Katalysator Kobalt-Molybdän in Kugelform. Dasselbe Rohmaterial wurde in einen Festbettreaktor eingeführt mit einer l.h.s.v. von 1,0 pro Stunde. Die Reaktionstemperatur wurde bei etwa 3800C gehalten, wogegen der Druck innerhalb des Reaktors etwa 29 bar (30 kg/cm2) erhalten wurde mit einer Wasserstoff-Flußrate von 500 ml H2 pro ml Rohmaterial. Das erhaltene Produkt war reich an geradkettigen Kohlenwasserstoffen, in denen die Kohlenstoffzahl zwischen 6 und 19 war.EXAMPLE 1 II In this example, the catalyst used was Cobalt-molybdenum in spherical form. The same raw material was put into a fixed bed reactor introduced with a l.h.s.v. from 1.0 per hour. The reaction temperature was kept at about 3800C, while the pressure inside the reactor was about 29 bar (30 kg / cm2) was obtained with a hydrogen flow rate of 500 ml H2 per ml of raw material. The product obtained was rich in straight chain hydrocarbons in which the Carbon number was between 6 and 19.
B e i s p i e 1 III In diesem Beispiel wurde dasselbe Rohmaterial verwendet, wie in den ersten beiden Beispielen. Der Katalysator in diesem Beispiel war Nickel-Molybdän in zylindrischer Form. Ein Festbettreaktor wurde verwendet, in dem der Druck bei etwa 29 bar (30 kg/cm2) gehalten wurde, mit einer Wasserstoff-Flußrate von 500 ml H2 pro ml Rohmaterial. Die Reaktionstemperatur wurde bei etwa 3800C gehalten und die l.h.s.v. war 1,0 pro Stunde. Das resultierende Produkt war reich an geradkettigen Kohlenwasserstoffen mit einer Kohlenstoffzahl zwischen 6 und 19.Example 1 III In this example, the same raw material was used used as in the first two examples. The catalyst in this example was nickel-molybdenum in a cylindrical shape. A fixed bed reactor was used by maintaining the pressure at about 29 bar (30 kg / cm2) with a hydrogen flow rate of 500 ml H2 per ml of raw material. The reaction temperature was maintained at about 3800C and the l.h.s.v. was 1.0 per hour. The resulting product was rich in straight chain Hydrocarbons with a carbon number between 6 and 19.
B e i s p i e 1 IV In diesem Beispiel wurde medizinisches Nußöl verwendet als Beispiel für einen ungesättigten Fettsäureglycerinester. Das katalytische Cracken wurde durchgeführt in einem Festbett innerhalb eines Reaktors mit einem Y-Zeolith-Aluminiumoxid-Katalysator. Die Reaktionstemperatur wurde bei etwa 3900C gehalten, während der Reaktionsdruck bei etwa 147 bar (150 kg/cm2) gehalten wurde. Die l.h.s.v. war 0,3 pro Stunde und das resultierende Produkt war reich an paraffinischen Kohlenwasserstoffen mit einer Kohlenstoffzahl zwischen 5 und 19.EXAMPLE 1 IV Medicinal nut oil was used in this example as an example of an unsaturated fatty acid glycerol ester. Catalytic cracking was carried out in a fixed bed within a reactor with a Y-zeolite-alumina catalyst. The reaction temperature was maintained at about 3900C while the reaction pressure was held at about 147 bar (150 kg / cm2). The l.h.s.v. was 0.3 per hour and the resulting product was rich in paraffinic hydrocarbons with a Carbon number between 5 and 19.
Vergleichsbeispiel l Für Vergleichs zwecke wurde ein oberes Rückstandsöl aus dem Mittleren Osten katalytisch gecrackt in einem Festbettreaktor, der einen Kobalt- Molybdän-Aluminiumoxid- Katalysator hatte. Die Reaktionstemperatur wurde bei etwa 3900C gehalten, während der Reaktionsdruck bei 147 bar (150 kg/cm2) gehalten wurde mit einer Wasserstoff-Flußrate von 930 ml H2 pro ml Beschickungsmaterial. Die l.h.s.v. wurde bei 0,3 pro Stunde gehalten. Die erhaltene Ausbeute war nur 17 Gew.-% von paraffinischen Kohlenwasserstoffen.Comparative Example 1 For comparative purposes, a top residue oil was used from the Middle East catalytically cracked in a fixed bed reactor, the one Cobalt molybdenum alumina Had catalyst. The reaction temperature was kept at about 3900C, while the reaction pressure was 147 bar (150 kg / cm2) was maintained at a hydrogen flow rate of 930 ml H2 per ml of feed. The l.h.s.v. was held at 0.3 per hour. The yield obtained was only 17 % By weight of paraffinic hydrocarbons.
V e r g 1 e i c h s b e i s p i e 1 II In diesem Beispiel wurde das obere Rückstandöl aus dem Mittleren Osten noch einmal verwendet in einem Festbettreaktor, der nun einen Y-Zeolith- Aluminiumoxid-Katalysator hatte. Die Reaktionstemperatur wurde bei etwa 3900C gehalten mit einem Reaktionsdruck von 147 bar (150 kg/cm2) und einer Wasserstoff-Flußrate von etwa 1200 ml H2 pro ml Rohmaterial. Die l.h.s.v. war 0,3 pro Stunde. Die Ausbeute an paraffinischen Kohlenwasserstoffen war 24,4 Gew.-%.V e r g 1 e i c h s b e i s p i e 1 II In this example, the Upper residual oil from the Middle East reused in a fixed bed reactor, which now had a Y-zeolite-alumina catalyst. The reaction temperature was kept at about 3900C with a reaction pressure of 147 bar (150 kg / cm2) and a hydrogen flow rate of about 1200 ml H2 per ml of raw material. The l.h.s.v. was 0.3 per hour. The yield of paraffinic hydrocarbons was 24.4 Wt%.
Tabelle 1
Claims (21)
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Application Number | Priority Date | Filing Date | Title |
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JP57196058A JPS59108088A (en) | 1982-11-10 | 1982-11-10 | Production of paraffin hydrocarbon |
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DE3340711A1 true DE3340711A1 (en) | 1984-09-27 |
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ID=16351492
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19833340711 Withdrawn DE3340711A1 (en) | 1982-11-10 | 1983-11-10 | Process for the preparation of paraffinic hydrocarbon solvents from vegetable oils |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS59108088A (en) |
BR (1) | BR8306186A (en) |
DE (1) | DE3340711A1 (en) |
IN (1) | IN160770B (en) |
PH (1) | PH19755A (en) |
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FR2607803A1 (en) * | 1986-12-08 | 1988-06-10 | Univ Paris Curie | Process for pressure hydrocracking of vegetable oils or of fatty acids derived from the said oils |
EP1681337A1 (en) * | 2005-01-14 | 2006-07-19 | Neste Oil OYJ | Method for the manufacture of hydrocarbons |
WO2007068796A2 (en) * | 2005-12-12 | 2007-06-21 | Neste Oil Oyj | Process for producing a branched hydrocarbon component |
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CZ301347B6 (en) * | 2005-10-05 | 2010-01-27 | Másílko@Rostislav | Process for preparing hydrocarbon mixtures with high content of n-paraffins |
US7850841B2 (en) | 2005-12-12 | 2010-12-14 | Neste Oil Oyj | Process for producing a branched hydrocarbon base oil from a feedstock containing aldehyde and/or ketone |
US7888542B2 (en) | 2005-12-12 | 2011-02-15 | Neste Oil Oyj | Process for producing a saturated hydrocarbon component |
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-
1982
- 1982-11-10 JP JP57196058A patent/JPS59108088A/en active Granted
-
1983
- 1983-11-03 PH PH29810A patent/PH19755A/en unknown
- 1983-11-10 BR BR8306186A patent/BR8306186A/en not_active IP Right Cessation
- 1983-11-10 DE DE19833340711 patent/DE3340711A1/en not_active Withdrawn
-
1984
- 1984-04-11 IN IN317/DEL/84A patent/IN160770B/en unknown
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2607803A1 (en) * | 1986-12-08 | 1988-06-10 | Univ Paris Curie | Process for pressure hydrocracking of vegetable oils or of fatty acids derived from the said oils |
EP1681337A1 (en) * | 2005-01-14 | 2006-07-19 | Neste Oil OYJ | Method for the manufacture of hydrocarbons |
WO2006075057A2 (en) * | 2005-01-14 | 2006-07-20 | Neste Oil Oyj | Method for the manufacture of hydrocarbons |
WO2006075057A3 (en) * | 2005-01-14 | 2006-12-28 | Neste Oil Oyj | Method for the manufacture of hydrocarbons |
CZ301347B6 (en) * | 2005-10-05 | 2010-01-27 | Másílko@Rostislav | Process for preparing hydrocarbon mixtures with high content of n-paraffins |
WO2007068796A3 (en) * | 2005-12-12 | 2007-08-09 | Neste Oil Oyj | Process for producing a branched hydrocarbon component |
US7967973B2 (en) | 2005-12-12 | 2011-06-28 | Neste Oil Oyj | Process for producing a hydrocarbon component |
WO2007068797A2 (en) * | 2005-12-12 | 2007-06-21 | Neste Oil Oyj | Process for producing a branched hydrocarbon component |
EP2881453A1 (en) * | 2005-12-12 | 2015-06-10 | Neste Oil Oyj | Process for producing a hydrocarbon component |
EP2881452A1 (en) * | 2005-12-12 | 2015-06-10 | Neste Oil Oyj | Process for producing a hydrocarbon component |
US8715486B2 (en) | 2005-12-12 | 2014-05-06 | Neste Oil Oyj | Process for producing a hydrocarbon component |
US8394258B2 (en) | 2005-12-12 | 2013-03-12 | Neste Oil Oyj | Process for producing a hydrocarbon component |
US7501546B2 (en) | 2005-12-12 | 2009-03-10 | Neste Oil Oj | Process for producing a branched hydrocarbon component |
US8053614B2 (en) | 2005-12-12 | 2011-11-08 | Neste Oil Oyj | Base oil |
WO2007068796A2 (en) * | 2005-12-12 | 2007-06-21 | Neste Oil Oyj | Process for producing a branched hydrocarbon component |
US7850841B2 (en) | 2005-12-12 | 2010-12-14 | Neste Oil Oyj | Process for producing a branched hydrocarbon base oil from a feedstock containing aldehyde and/or ketone |
US7888542B2 (en) | 2005-12-12 | 2011-02-15 | Neste Oil Oyj | Process for producing a saturated hydrocarbon component |
US7998339B2 (en) | 2005-12-12 | 2011-08-16 | Neste Oil Oyj | Process for producing a hydrocarbon component |
WO2007068797A3 (en) * | 2005-12-12 | 2007-08-02 | Neste Oil Oyj | Process for producing a branched hydrocarbon component |
WO2007090884A3 (en) * | 2006-02-09 | 2007-09-20 | Shell Int Research | Fluid catalytic cracking process |
WO2007090884A2 (en) * | 2006-02-09 | 2007-08-16 | Shell Internationale Research Maatschappij B.V. | Fluid catalytic cracking process |
CN101454424B (en) * | 2006-05-25 | 2012-07-04 | 英国石油国际有限公司 | Hydrogenation process |
WO2007138254A1 (en) * | 2006-05-25 | 2007-12-06 | Bp Oil International Limited | Hydrogenation process |
WO2008157465A3 (en) * | 2007-06-15 | 2009-11-19 | E. I. Du Pont De Nemours And Company | Catalytic process for converting renewable resources into paraffins for use as diesel blending stocks |
WO2008157465A2 (en) * | 2007-06-15 | 2008-12-24 | E. I. Du Pont De Nemours And Company | Catalytic process for converting renewable resources into paraffins for use as diesel blending stocks |
WO2011012440A3 (en) * | 2009-07-27 | 2011-07-21 | Total Petrochemicals Research Feluy | A process for the production of bio-naphtha from complex mixtures of natural occurring fats & oils |
EP2290045A1 (en) * | 2009-07-27 | 2011-03-02 | Total Petrochemicals Research Feluy | A process for the production of bio-naphtha from complex mixtures of natural occurring fats and oils |
US8624071B2 (en) | 2009-07-27 | 2014-01-07 | Total Petrochemicals Research Feluy | Process for the production of bio-naphtha from complex mixtures of natural occurring fats and oils |
WO2014111598A2 (en) * | 2013-01-21 | 2014-07-24 | Total Research & Technology Feluy | A process for the production of bio-naphtha from complex mixtures of natural occurring fats & oils |
WO2014111598A3 (en) * | 2013-01-21 | 2014-10-16 | Total Research & Technology Feluy | Process for the production of bio-naphtha from complex mixtures of natural occurring fats & oils |
Also Published As
Publication number | Publication date |
---|---|
IN160770B (en) | 1987-08-01 |
JPS59108088A (en) | 1984-06-22 |
PH19755A (en) | 1986-06-26 |
BR8306186A (en) | 1984-06-12 |
JPS6158510B2 (en) | 1986-12-11 |
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