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WO2018047032A2 - Procédé de conversion sélective d'hydrocarbures en fraction c2 et composition de gaz de synthèse - Google Patents

Procédé de conversion sélective d'hydrocarbures en fraction c2 et composition de gaz de synthèse Download PDF

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Publication number
WO2018047032A2
WO2018047032A2 PCT/IB2017/055120 IB2017055120W WO2018047032A2 WO 2018047032 A2 WO2018047032 A2 WO 2018047032A2 IB 2017055120 W IB2017055120 W IB 2017055120W WO 2018047032 A2 WO2018047032 A2 WO 2018047032A2
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WIPO (PCT)
Prior art keywords
hydrogenation
hydrocarbon source
pyrolysis
natural gas
acetylene
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English (en)
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WO2018047032A3 (fr
Inventor
Krishnan Sankaranarayanan
Pankaj S. GAUTAM
Aghaddin Mamedov
Sreekanth Pannala
Balamurali Nair
Istvan Lengyel
David West
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SABIC Global Technologies BV
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SABIC Global Technologies BV
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Publication of WO2018047032A3 publication Critical patent/WO2018047032A3/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
    • C07C2/78—Processes with partial combustion
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
    • C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
    • C01B3/32—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air
    • C01B3/34—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents
    • C01B3/36—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents using oxygen or mixtures containing oxygen as gasifying agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
    • C07C4/04—Thermal processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/02—Processes for making hydrogen or synthesis gas
    • C01B2203/025—Processes for making hydrogen or synthesis gas containing a partial oxidation step
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/04—Integrated processes for the production of hydrogen or synthesis gas containing a purification step for the hydrogen or the synthesis gas
    • C01B2203/0415—Purification by absorption in liquids
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/04—Integrated processes for the production of hydrogen or synthesis gas containing a purification step for the hydrogen or the synthesis gas
    • C01B2203/042—Purification by adsorption on solids
    • C01B2203/043—Regenerative adsorption process in two or more beds, one for adsorption, the other for regeneration
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/04—Integrated processes for the production of hydrogen or synthesis gas containing a purification step for the hydrogen or the synthesis gas
    • C01B2203/046—Purification by cryogenic separation
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/04—Integrated processes for the production of hydrogen or synthesis gas containing a purification step for the hydrogen or the synthesis gas
    • C01B2203/0465—Composition of the impurity
    • C01B2203/0475—Composition of the impurity the impurity being carbon dioxide
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/06—Integration with other chemical processes
    • C01B2203/061—Methanol production
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/06—Integration with other chemical processes
    • C01B2203/062—Hydrocarbon production, e.g. Fischer-Tropsch process
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/12—Feeding the process for making hydrogen or synthesis gas
    • C01B2203/1205—Composition of the feed
    • C01B2203/1211—Organic compounds or organic mixtures used in the process for making hydrogen or synthesis gas
    • C01B2203/1235—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/12—Feeding the process for making hydrogen or synthesis gas
    • C01B2203/1205—Composition of the feed
    • C01B2203/1211—Organic compounds or organic mixtures used in the process for making hydrogen or synthesis gas
    • C01B2203/1235—Hydrocarbons
    • C01B2203/1241—Natural gas or methane
    • 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
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • 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
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/44—Palladium

Definitions

  • the discovery is premised on conversion of low value hydrocarbons ⁇ e.g., heavy residue or petroleum coke) to C2 hydrocarbons while simultaneously producing other building block chemicals such as syngas.
  • Embodiments of the invention include processes for the production of C2 hydrocarbons (C2H2 and/or C2H4) in an energy and carbon efficient process.
  • Certain embodiments are directed to an energy and carbon efficient process for conversion of hydrocarbon source to C2 hydrocarbons can include: (a) combusting in a first reaction zone a hydrocarbon source containing natural gas in the presence of oxygen to produce combustion products; (b) mixing the combustion products with a second hydrocarbon source in a second reaction zone in which pyrolysis occurs forming pyrolysis products that include C2H2, C2H4, and CO2, the second reaction zone being heated by the combustion in the first reaction zone; (c) quenching the pyrolysis reaction product; (d) subjecting the C2H2 to hydrogenation forming C2H4; and (e) subjecting the CO2 to hydrogenation forming a syngas.
  • the hydrocarbon source can be a mixture of natural gas and heavy hydrocarbons.
  • the hydrocarbon source can be a mixture of natural gas and petcoke.
  • the hydrocarbon source can be a mixture of natural gas and heavy residue.
  • the hydrocarbon source can be a mixture of natural gas and heavy oil.
  • the hydrocarbon source can be a mixture of natural gas and naphtha.
  • the second hydrocarbon source can be ethane, propane, naphtha, or combinations thereof.
  • pyrolysis can result in an acetylene (C2H2) yield of at least 20, 25, 30, 35% or more. The C2H2 can be separated from the pyrolysis products and then subjected to hydrogenation.
  • the C2H2 can be separated by selective solvation in a N- methyl-2-pyrrolidone ( MP) solvent.
  • unreacted H2 in the hydrogenation reaction can be recycled to the combustion zone.
  • the process can further include separating CO2 from the pyrolysis product by amine absorption.
  • the process can also include converting separated CO2 to methanol or olefins.
  • the unreacted H2 from acetylene hydrogenation can be used for CO2 hydrogenation.
  • the process can further include reacting the CO2 hydrogenation product and the pyrolysis product to form methanol.
  • natural gas refers to a naturally occurring hydrocarbon gas mixture consisting primarily of methane, but can include varying amounts of other higher alkanes, and sometimes a small percentage of carbon dioxide, nitrogen, hydrogen sulfide, or helium.
  • the term "heavy residue” refers to polyalkylbenzenes such as polyethylbenzenes (PEB's) and multi-ring compounds.
  • petroleum coke refers to a carbonaceous solid delivered from oil refinery coker units or other cracking processes.
  • heavy hydrocarbons refers to hydrocarbons which are solid or extremely viscous at standard processing conditions.
  • heavy hydrocarbons include materials asphaltenes, tars, paraffin waxes, coke, refining residuum, and other similar residual hydrocarbon materials.
  • heavy hydrocarbons include any material that comprises a majority of hydrocarbon materials with a molecular weight range of about 700 to 2,000,000.
  • heavy oil refers to heavy crude, oil sands bitumen, bottom of the barrel and residue left over from refinery processes (e.g., visbreaker bottoms), and any other lower quality material that contains a substantial quantity of high boiling hydrocarbon fractions (e.g., that boil at or above 343 °C, more particularly at or above about 524 °C.
  • Non-limiting examples of heavy oil feedstocks include Lloydminster heavy oil, Cold Lake bitumen, Athabasca bitumen, atmospheric tower bottoms, vacuum tower bottoms, residuum (or "resid"), resid pitch, vacuum residue, and nonvolatile liquid fractions that remain after subjecting crude oil, bitumen from tar sands, liquefied coal, oil shale, or coal tar feedstocks to distillation, hot separation, and the like and that contain higher boiling fractions and/or asphaltenes.
  • naphtha refers to flammable liquid hydrocarbon mixtures.
  • wt.% refers to a weight percentage of a component, a volume percentage of a component, or molar percentage of a component, respectively, based on the total weight, the total volume of material, or total moles, that includes the component.
  • 10 grams of component in 100 grams of the material is 10 wt.% of component.
  • the methods of the present invention can "comprise,” “consist essentially of,” or “consist of particular ingredients, components, compositions, etc. disclosed throughout the specification.
  • a basic and novel characteristic of the methods of the present invention are their abilities to convert low value hydrocarbons into C2 hydrocarbons and carbon oxides.
  • FIG. 1 shows a schematic of one embodiment of the combustion/pyrolysis process in combination with an amine separation system.
  • FIG. 2 shows a schematic of one embodiment of the syngas production process.
  • aspects of the invention relate to a process for the conversion of natural gas and/or any hydrocarbon feed such as heavy residue or petcoke to useful products, such as C2 hydrocarbons (acetylene and/or ethylene).
  • the process can include the simultaneous production of syngas compositions making the overall process a high carbon efficient process.
  • aspects of the current invention are directed to methods that result in a more carbon efficient process.
  • the current invention can be used to convert a wide range of hydrocarbon feedstock, such as heavy residue or petcoke, which are low value hydrocarbons, to more useful products such as C2 hydrocarbons while simultaneously producing other useful products such as syngas.
  • Oxidative pyrolysis of methane is accompanied by selective oxidation reactions that generate high amounts of heat:
  • the oxidative pyrolysis process conditions can depend from the CH4/O2 ratio and can require a critical ratio for elimination of coke and soot formation.
  • the ratio of acetylene to syngas ratio can also depend from the process conditions and the CH4/O2 ratio.
  • One embodiment described herein includes two main reaction zones and one quenching zone.
  • the first reaction zone where preheated methane can be combusted, serves to supply the necessary heat for the second reaction zone, where a fresh feed of methane can be injected for pyrolysis and mixed with the combustion products of the first zone ⁇ See, FIG. 1).
  • water or heavy oil can be used as a coolant.
  • the gas after cooling can be fed to an acetylene absorbing unit where liquid phase acetylene is hydrogenated to ethylene in the presence of hydrogenation catalyst ⁇ See, for example FIG. 1).
  • acetylene absorbing unit where liquid phase acetylene is hydrogenated to ethylene in the presence of hydrogenation catalyst ⁇ See, for example FIG. 1).
  • hydrogenation catalyst ⁇ See, for example FIG. 1.
  • n-methyl-2-pyrrolidone ( MP), dimethylformamide (DMF), acetone, tetrahydrofuran (TUF), dimethylsulfoxide (DMSO), monomethylamine (MMA) and chloroform can be used to preferentially absorb acetylene from a gas stream.
  • the solvent containing absorbed acetylene can then be subjected to hydrogenation in the liquid phase.
  • Hydrogenation conditions can include a temperature of about 200 °C to about 300 °C, or greater than, equal to, or between any two of 200 °C, 210 °C, 220 °C, 230 °C, 240 °C, 250 °C, 260 °C, 270 °C, 280 °C, 290 °C and 300 °C.
  • acetylene hydrogenation can be carried out in liquid phase.
  • the final products of the process are C2H4 and CO2.
  • the molar ratio of C2H4 and CO2 in weight basis can be within 1.3 - 1.45.
  • the total process can be described as follows:
  • CO2 with hydrogen can be used for syngas conversion reactions such as syngas to methanol or syngas to olefins, which requires only a limited amount of CO2.
  • the present invention utilizes the CO2 by-product of methane to acetylene process for generation of syngas composition for further processing, which increases the economics of the process significantly.
  • Separation of the products from the methane to acetylene reactor can involve separation of CO2 from the product stream and then separation of the C2 hydrocarbons. Separation of CO2 can be conducted by any known method, for example, by amine adsorption. Separation of C2 hydrocarbons from the product stream can include cold box separation or pressure swing adsorption (PSA). In one aspect, after separation of C 2 hydrocarbons, CO2 can be mixed with H 2 in the necessary ratio to produce a syngas composition having an appropriate H2/CO2/CO ratio for methanol or olefins synthesis (See, for example, FIG. 2).
  • a portion of the syngas composition can be used for hydrogenation of acetylene.
  • the gas composition produced during the hydrogenation of acetylene can contain more CO and less hydrogen, and can be mixed with the CO2 hydrogenation gas mixture.
  • the adjusted syngas composition can be used for methanol or olefins synthesis depending on the composition of syngas generated from CO2 hydrogenation reaction.
  • the CO2 byproduct can be converted to syngas using hydrogenating agent, e.g., hydrogen or any suitable compound that can provide hydrogen for hydrogenation reaction. Hydrogenation of CO2 to syngas composition can be described by the following reactions:
  • Reaction (5) is an equilibrium controlled reaction and depends on the H2/CO2 ratio, for example:
  • Catalysts for CO2 hydrogenation to syngas can include mixed oxides of redox metals, for example, chromium (Cr), iron (Fe), manganese (Mn), or copper (Cu) based oxides.
  • a Cr based industrial Catofin® (CB&I, U.S.A.) catalyst can be used, Such a catalyst can produce a desired syngas mixture for methanol production.
  • the composition of syngas can depend on the molar H2/CO2 ratio and from the reaction temperature. With variation of the process conditions, it is possible to direct the process for different purposes.
  • the process can be applied for converting of wide range hydrocarbons, such as heavy residue and also low value carbon resources such as petcoke.
  • the hydrocarbon feed can be a mixture of different hydrocarbons, such as mixture of natural gas with heavy residue, mixture of natural gas with ethane, propane, or mixture of methane with naphtha, or mixture of methane with petcoke.
  • the Hydrogenation results were: (i) C2H2 conversion - 96.3 % mol, (ii) C2H4 selectivity - 91.5 % mol, (iii) C2H6 selectivity - 3.1 % mol, and (iv) CH4 selectivity - 5.4% mol.
  • the green oil (e.g., a mixture of C 4 to C20 olefins and paraffins), which was produced as a byproduct, was separated from the liquid phase and recycled back to the combustion zone.
  • the portion of the gas not used for hydrogenation step after separation of CO2 was recycled back to the combustion zone for generation of heat.
  • a syngas composition produced from the pyrolysis step was mixed with the syngas composition produced from CO2 hydrogenation step and used for methanol synthesis or olefins production.
  • the syngas composition produced from pyrolysis step was used for heat generation and as a CO2 hydrogenation syngas to be used for methanol synthesis.
  • the flow rates of gas components were as following: H2 - 112 cc/min and CO2 - 25 cc/min.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Inorganic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention cocnerne des procédés pour la production d'hydrocarbures C2 (C2H2 et/ou C2H4) dans un processus efficace en termes d'énergie et de carbone.
PCT/IB2017/055120 2016-09-08 2017-08-24 Procédé de conversion sélective d'hydrocarbures en fraction c2 et composition de gaz de synthèse Ceased WO2018047032A2 (fr)

Applications Claiming Priority (2)

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US201662384903P 2016-09-08 2016-09-08
US62/384,903 2016-09-08

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WO2018047032A2 true WO2018047032A2 (fr) 2018-03-15
WO2018047032A3 WO2018047032A3 (fr) 2018-09-13

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Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007082746A1 (fr) * 2006-01-23 2007-07-26 Saudi Basic Industries Corporation Procédé de production d'éthylène à partir de gaz naturel avec intégration de chaleur
JP5592250B2 (ja) * 2007-04-27 2014-09-17 サウディ ベーシック インダストリーズ コーポレイション 二酸化炭素の合成ガスへの接触水素化
US8551434B1 (en) * 2012-06-29 2013-10-08 Saudi Basic Industries Corporation Method of forming a syngas mixture
WO2015069840A1 (fr) * 2013-11-11 2015-05-14 Saudi Basic Industries Corporation Procédé pour l'hydrogénation du co2 dans des réacteurs métalliques adiabatiques
EP3261990A1 (fr) * 2015-02-23 2018-01-03 SABIC Global Technologies B.V. Procédés d'hydrogénation de dioxyde de carbone en gaz de synthèse

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