EP3663380A1 - Procédé de fabrication continue d'oléfines et d'essence de pyrolyse à partir d'un triester de la glycérine - Google Patents

Procédé de fabrication continue d'oléfines et d'essence de pyrolyse à partir d'un triester de la glycérine Download PDF

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Publication number
EP3663380A1
EP3663380A1 EP18211110.4A EP18211110A EP3663380A1 EP 3663380 A1 EP3663380 A1 EP 3663380A1 EP 18211110 A EP18211110 A EP 18211110A EP 3663380 A1 EP3663380 A1 EP 3663380A1
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European Patent Office
Prior art keywords
oil
glycerol
range
triester
mixture
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.)
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Application number
EP18211110.4A
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German (de)
English (en)
Inventor
Heinrich Laib
Ronny RAQUET
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BASF SE
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BASF SE
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Publication date
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Priority to EP18211110.4A priority Critical patent/EP3663380A1/fr
Publication of EP3663380A1 publication Critical patent/EP3663380A1/fr
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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
    • 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
    • C10G3/47—Catalytic treatment characterised by the catalyst used containing platinum group metals or compounds thereof
    • 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
    • C10G3/50—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids in the presence of hydrogen, hydrogen donors or hydrogen generating compounds
    • 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
    • C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G9/34—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils by direct contact with inert preheated fluids, e.g. with molten metals or salts
    • C10G9/36—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils by direct contact with inert preheated fluids, e.g. with molten metals or salts with heated gases or vapours
    • 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
    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/20—C2-C4 olefins

Definitions

  • the invention relates to a process for the continuous production of olefins and pyrolysis gasoline from a triester of glycerol or a mixture of triesters of glycerol.
  • Steam cracking is a petrochemical process in which long-chain hydrocarbons [e.g. Gasoline (also called raw gasoline), naphtha] can be converted into short-chain hydrocarbons in the presence of water vapor.
  • the main products are olefins, methane and pyrolysis gasoline.
  • Pyrolysis gasoline is a by-product of ethylene production by steam splitting gasoline in a canned furnace. It typically boils in the range of 30 to 220 ° C and, depending on the chemical nature of the gasoline used, contains 45 to 60% by weight of benzene, toluene and xylene, as well as 10 to 15% by weight of higher-boiling aromatics.
  • fractions of unsaturated compounds such as olefins, diolefins and polymer are contained in the pyrolysis gasoline, which are determined by the bromine number, diene number and the gum test (ASTM D381). ( EP 24 299 B1 , BASF AG).
  • illustration 1 shows schematically as an example, as part of a steam cracking system, a canned furnace (III) with convection zone (I) and radiation zone (II), the tubes of the preheater in the convection zone, the canned pipe system in the radiation zone and a quench cooler for the cracked gas.
  • Figure 2 shows as an excerpt from illustration 1 the plant part modified according to a preferred embodiment of the method according to the invention for the continuous hydrogenation of the triester of the glycerol or the mixture of triesters of the glycerol with hydrogen in pipes with hydrogenation catalyst filling in the convection zone (I) of the canned furnace (III).
  • the heated feed stream e.g. 100 ° C hot, e.g. naphtha
  • the heated feed stream is usually at elevated pressure (> 1 bar), particularly at a pressure in the range from 6 to 15 bar, e.g. at about 12 bar, in the convection zone (I ) of a canned furnace (III) preheated to a temperature in the range from 550 to 600 ° C.
  • Process steam at a temperature of 180 to 200 ° C is also added in this zone (hence the name steam cracking).
  • the process steam serves to bring about a reduction in the partial pressure of the individual reaction participants.
  • it partially prevents the finished reaction products (olefins / alkenes) from accumulating (polymerization) and cools the heating coil in the convection zone.
  • the now more completely gaseous feed stream reaches the radiation zone (II).
  • the hot cracked gas is suddenly cooled in a heat exchanger to a temperature in the range of approximately 350 to 400 ° C (this is often a high-pressure feed water cooler) .
  • the hot cracked gas is then additionally cooled with quench oil to a temperature in the range from 150 to 170 ° C. for the subsequent fractionation.
  • bionaphtha from triesters of glycerol is known.
  • DE 60312446 T3 Neste Oil Oyj
  • a hydrocarbon component of biological origin from biological starting materials such as vegetable oils, animal fats and similar materials, this component being particularly useful in diesel fuels.
  • the invention had for its object to provide an improved process for the production of olefins and pyrolysis gasoline from renewable raw materials, which is more economical, in particular with regard to investment and energy costs, and which delivers the products in high yield and selectivity.
  • a process for the continuous production of olefins and pyrolysis gasoline from a triester of glycerol or a mixture of triesters of glycerol is characterized in that first the triester or glycerol is hydrogenated in the presence of a hydrogenation catalyst at a temperature in the range from 100 to 400 ° C to form a gaseous product stream containing a hydrocarbon or a mixture of hydrocarbons and each reaction water vapor, continuously hydrogenated and then the hydrocarbon (s) in the gaseous product stream without the addition of further water vapor in a metallic tubular reactor continuously at a temperature splits in the range from 780 to 850 ° C, particularly 790 to 830 ° C, very particularly 800 to 825 ° C.
  • the continuous splitting is carried out particularly at an absolute pressure in the range from 2 to 5 bar, very particularly 2.5 to 4.5 bar.
  • the residence time ⁇ of the cleavage products in the tubular reactor is preferably 0.1 to 0.5 s, particularly preferably 0.2 to 0.4 s.
  • the invention thus comprises the use of renewable raw materials in the form of a triester of glycerol or in the form of a mixture of triesters of glycerol in steam cracker plants, also called ethylene plants, that is to say in canned furnaces in which, for example, Naphtha would be used, without the use of additional steam, for the production of olefins and pyrolysis gasoline.
  • the olefins produced according to the invention are particularly ethylene and propylene.
  • the pyrolysis gasoline produced according to the invention is particularly a mixture comprising benzene, toluene and xylene, in particular containing 45 to 60% by weight of the aromatics benzene, toluene and xylene and, in addition, 10 to 15% by weight of higher-boiling aromatics.
  • fractions of unsaturated compounds such as olefins, diolefins and / or polymer may also be present in the pyrolysis gasoline, which can be determined, for example, by the bromine number, diene number or the gum test (ASTM D381).
  • the triester of glycerin is particularly a triester of the glycerol molecule [HO-CH 2 -C (H) (OH) -CH 2 -OH] with three fatty acid molecules [R 1 -COOH, R 2 -COOH, R 3 - COOH]:
  • R 1 , R 2 and R 3 are identical or different fatty acid residues and are particularly, independently of one another, saturated or unsaturated alkyl residues, very particularly C 6 -C 24 alkyl residues.
  • the mixture of triesters of glycerol is preferably a vegetable oil which is a renewable raw material. Almost all known vegetable oils and mixtures thereof, from two or more of these oils, can be used as the starting material. Particular examples are palm oil, grape seed oil, hemp oil, soybean oil, cottonseed oil, wheat germ oil, corn oil, sunflower oil, rapeseed oil or castor oil. Palm oil is a particularly preferred oil as a feed. A cleaning pretreatment of the oil, for example distillation, may be advantageous or necessary.
  • the continuous hydrogenation is carried out at a temperature in the range from 100 to 400 ° C., especially 120 to 380 ° C., very particularly 140 to 360 ° C., for example also 100 to 200 ° C.
  • the continuous hydrogenation is carried out in particular at an absolute pressure in the range from 3 to 12 bar, very particularly 4 to 11 bar.
  • the hydrogenation catalyst preferably contains one or more metals from Group VIII and / or Vlb and / or IB of the Periodic Table of the Elements, in particular Pd, Pt, Cu, Ni, Cu / Ni, Cu / Ni / Co , Ni / Mo or Co / Mo.
  • Supported hydrogenation catalysts are particularly preferred, the support being in particular aluminum oxide, zirconium dioxide or silicon dioxide.
  • An example of a very particularly preferred hydrogenation catalyst is a Pd catalyst with aluminum oxide as a carrier, for example 0.1 to 0.5% by weight of Pd (based on the catalyst mass) on aluminum oxide.
  • Other typical examples are Ni / Mo / aluminum oxide and Co / Mo / aluminum oxide catalysts.
  • the hydrogenation catalyst is particularly preferably arranged as a fixed catalyst bed in the metallic tubular reactor.
  • the metal of the tubular reactor for the hydrogenation consists especially of a steel which has the required stability under the corresponding reaction conditions (temperature, hydrogen presence, running time). In a special embodiment, the metal is the same as that used for the pipes in the convection zone (I) of a canned furnace (III) becomes.
  • the tube of the tube reactor is the same as the tube or a part of the tube which is used in the convection zone (I) of a canned furnace (III).
  • the gaseous fission product obtained contained components as follows (measured at 35 ° C. and 1 bar). GC analysis gas phase V1 V2 V3 V4 V5 Hydrogen [ml / min.] 265 250 150 50 12.5 Fission product Vol .-% Vol .-% Vol .-% Vol .-% H2 22.28 19.98 16.66 11.79 10.12 CO2 nb 4.17 4.39 4.75 4.86 CO 10.12 8.60 9.21 9.72 9.93 methane 18.38 18.98 20.24 20.09 20.63 Ethylene 30.98 30.19 31.16 33.21 33.99 Propylene 7.62 7.72 7.64 8.86 9.15 1,3-butadiene 2.44 2.69 2.54 3.02 3.07 benzene 1.57 1.66 2.22 1.25 1.12 toluene 0.21 0.15 0.26 0.09 0.08 total 93.60 94.14 94.32 92.78 92.95

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  • 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)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP18211110.4A 2018-12-07 2018-12-07 Procédé de fabrication continue d'oléfines et d'essence de pyrolyse à partir d'un triester de la glycérine Withdrawn EP3663380A1 (fr)

Priority Applications (1)

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EP18211110.4A EP3663380A1 (fr) 2018-12-07 2018-12-07 Procédé de fabrication continue d'oléfines et d'essence de pyrolyse à partir d'un triester de la glycérine

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EP18211110.4A EP3663380A1 (fr) 2018-12-07 2018-12-07 Procédé de fabrication continue d'oléfines et d'essence de pyrolyse à partir d'un triester de la glycérine

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119798024A (zh) * 2025-03-14 2025-04-11 江西省林业科学院 一种甘油三酯类化合物制备α-烯烃的方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024299B1 (fr) 1979-08-04 1983-01-26 BASF Aktiengesellschaft Procédé pour l'obtention de composés aromatiques à partir de benzine pyrolisée
US20070015947A1 (en) * 2005-05-19 2007-01-18 Marker Terry L Production of olefins from biorenewable feedstocks
US20100292517A1 (en) * 2007-06-12 2010-11-18 Ifp Production of vapour-cracking loads with a high yield of the resulting ethylene, propylene and polymers by hydroprocessing of vegetable oils
WO2014111598A2 (fr) 2013-01-21 2014-07-24 Total Research & Technology Feluy Procédé de production de bionaphta à partir de mélanges complexes de graisses et huiles d'origine naturelle
EP2770040A2 (fr) * 2013-02-26 2014-08-27 Basf Se Procédé de fabrication de bio-hydrocarbures
DE60312446T3 (de) 2002-09-06 2017-04-27 Neste Oil Oyj Vefahren zur Herstellung einer Kohlenwasserstoffkomponente biologischer Herkunft
US20170298280A1 (en) * 2014-10-13 2017-10-19 Total Research & Technology Feluy Process for the Production of High Value Chemicals from Biologically Produced Materials

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024299B1 (fr) 1979-08-04 1983-01-26 BASF Aktiengesellschaft Procédé pour l'obtention de composés aromatiques à partir de benzine pyrolisée
DE60312446T3 (de) 2002-09-06 2017-04-27 Neste Oil Oyj Vefahren zur Herstellung einer Kohlenwasserstoffkomponente biologischer Herkunft
US20070015947A1 (en) * 2005-05-19 2007-01-18 Marker Terry L Production of olefins from biorenewable feedstocks
US20100292517A1 (en) * 2007-06-12 2010-11-18 Ifp Production of vapour-cracking loads with a high yield of the resulting ethylene, propylene and polymers by hydroprocessing of vegetable oils
WO2014111598A2 (fr) 2013-01-21 2014-07-24 Total Research & Technology Feluy Procédé de production de bionaphta à partir de mélanges complexes de graisses et huiles d'origine naturelle
US20150353864A1 (en) * 2013-01-21 2015-12-10 Total Research & Technology Feluy Process for the Production of Bio-Naphtha from Complex Mixtures of Natural Occurring Fats & Oils
EP2770040A2 (fr) * 2013-02-26 2014-08-27 Basf Se Procédé de fabrication de bio-hydrocarbures
US20170298280A1 (en) * 2014-10-13 2017-10-19 Total Research & Technology Feluy Process for the Production of High Value Chemicals from Biologically Produced Materials

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
L. KNIEL; O. WINTER; K. STORK: "Ethylene: Keystone to the Petrochemical Industry", 1980, MARCEL DEKKER INC.
SIEHE Z.B. D. GLIETENBERG ET AL.: "Ullmanns Encyklopädie der technischen Chemie", vol. 8, 1974, VERLAG CHEMIE, pages: 158 - 194
WEISSERMEHL K ET AL: "Kapitel 3 - Olefine", 1990, INDUSTRIELLE ORGANISCHE CHEMIE, BEDEUTENDE VOR- UND ZWISCHENPRODUKTE,, PAGE(S) 63 - 81, ISBN: 978-3-527-26731-6, XP009512811 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119798024A (zh) * 2025-03-14 2025-04-11 江西省林业科学院 一种甘油三酯类化合物制备α-烯烃的方法

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