US20050038310A1 - Hydrocarbon synthesis - Google Patents

Hydrocarbon synthesis Download PDF

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Publication number
US20050038310A1
US20050038310A1 US10/893,418 US89341804A US2005038310A1 US 20050038310 A1 US20050038310 A1 US 20050038310A1 US 89341804 A US89341804 A US 89341804A US 2005038310 A1 US2005038310 A1 US 2005038310A1
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Prior art keywords
hydrocarbon
recited
cataloreactant
oxygen
carbon number
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Ivan Lorkovic
Maria Noy
Jeffrey Sherman
Michael Weiss
Galen Stucky
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University of California
Reaction 35 LLC
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Individual
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Assigned to GRT, INC. reassignment GRT, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SHERMAN, JEFFREY H., WEISS, MICHAEL J.
Assigned to REGENTS OF THE UNIVERSITY OF CALIFORNIA, THE reassignment REGENTS OF THE UNIVERSITY OF CALIFORNIA, THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LORKOVIC, IVAN M., NOY, MARIA, STUCKY, GALEN D.
Publication of US20050038310A1 publication Critical patent/US20050038310A1/en
Priority to US11/091,130 priority patent/US20050171393A1/en
Priority to US12/080,594 priority patent/US20080188697A1/en
Priority to US12/217,311 priority patent/US7847139B2/en
Priority to US12/683,607 priority patent/US7964764B2/en
Priority to US13/107,611 priority patent/US8278493B2/en
Assigned to REACTION 35, LLC reassignment REACTION 35, LLC RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: HOOK, THOMAS W.
Assigned to REACTION 35, LLC reassignment REACTION 35, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GRT, INC.
Abandoned legal-status Critical Current

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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
    • C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • 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
    • C07C2521/10—Magnesium; 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
    • C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
    • 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
    • C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
    • 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
    • C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
    • 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
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/93—Process including synthesis of nonhydrocarbon intermediate
    • Y10S585/935—Halogen-containing
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/943—Synthesis from methane or inorganic carbon source, e.g. coal

Definitions

  • This invention relates generally to hydrocarbon oligomerization, and more particularly to a method of making hydrocarbons using cataloreactants.
  • U.S. Pat. Nos. 6,486,368, 6,472,572, 6,465,699, 6,465,696, and 6,462,243 disclose processes for converting alkanes into olefins, ethers, and alcohols. Many of the disclosed processes involve halogenation of an alkane, passing the halogenated products over a metal oxide to create products and metal halide, recovering the product(s), and regenerating the metal halide with oxygen or air to yield metal oxide and halogen for recycle to the process. Not described is alkane oligomerization: substantial coupling of the starting hydrocarbon to obtain product(s) of higher carbon number.
  • the chlorinated alkanes are contacted with a crystalline aluminosilicate catalyst in the hydrogen or metal-promoted form to produce gasoline range hydrocarbons with a high proportion of aromatics and a small percentage of light hydrocarbons (C 2 -C 4 ), as well as reforming the HCl.
  • the light hydrocarbons can be recycled for further processing over the oxyhydrochlorination catalyst.” All of these techniques for making higher alkanes from C 1 feedstocks suffer from the disadvantage that the hydrocarbon stream must be separated from an aqueous hydrohalic acid stream, and the hydrohalic acid stream must be recycled.
  • U.S. Pat. No. 4,795,843 discloses a process for oligomerizing halomethanes to products including ethyl benzene, toluene, and xylenes, using silica polymorph or silicalite catalysts. The process does not incorporate reactive neutralization of hydrogen halide, and appears to suffer from slow kinetics.
  • U.S. Pat. No. 4,373,109 discloses a process for converting heterosubstituted methanes, including methyl halides, by contacting such methanes with bifunctional acid-base catalysts at elevated temperatures, between 200 and 450° C., preferably between 250 and 375° C., to produce predominantly lower olefins, preferably ethylene and propylene.
  • the catalysts of preference are those derived from halides, oxyhalides, oxides, sulfides or oxysulfides of transition metals of Groups IV, V, VI, VIII of the Periodic Table, such as tantalum, niobium, zirconium, tungsten, titanium, and chromium, deposited on acidic oxides and sulfides such as alumina, silica, zirconia or silica-alumina. Neither the use of solid oxide-based halogen recovery nor the formation of alcohols or ethers is disclosed.
  • a related reference is “Ylide chemistry. 1. Bifunctional acid-base-catalyzed conversion of heterosubstituted methanes into ethylene and derived hydrocarbons. The onium-ylide mechanism of the C 1 ⁇ C 2 conversion” by George A. Olah et al. (J. Am. Chem. Soc. 106, 2143 (1984)).
  • a hydrocarbon having a carbon number C n is prepared by allowing a reactant hydrocarbon having a carbon number C m , where m ⁇ n, to react with a halogenating agent, thereby forming a halogenated hydrocarbon; allowing the halogenated hydrocarbon to contact a metal-oxygen cataloreactant, thereby forming a product hydrocarbon having an carbon number C n , where n ⁇ 2; recovering the product hydrocarbon; and regenerating the cataloreactant.
  • a hydrocarbon having a carbon number C n is formed by (i) forming a halogenated hydrocarbon by allowing a reactant hydrocarbon having a carbon number C m , where m ⁇ n, to react with a halogenating agent; (ii) forming a product hydrocarbon having a carbon number C n , where n ⁇ 2, by allowing the halogenated hydrocarbon to contact a metal-oxygen cataloreactant; (iii) recovering the product hydrocarbon; and (iv) regenerating the cataloreactant.
  • the method entails the steps of halogenation, oligomerization, product recovery, and cataloreactant regeneration.
  • the halogenated products may be separated from the unreacted (non-halogenated) hydrocarbon either before or after reaction with the metal-oxygen cataloreactant.
  • Neutralization of any hydrohalic acid formed during the synthesis is advantageously accomplished concommitantly with carbon-carbon coupling and/or cataloreactant regeneration.
  • the process is an integrated one and takes place, for example, in a zone reactor, as described, for example, in U.S. Pat. No. 6,525,230 (Grosso), the entire contents of which is incorporated by reference herein.
  • halogenation of methane or other hydrocarbons occurs within one zone of the reactor, and is followed by a condensation step in which the liberated hydrohalic acid is adsorbed within the same bifunctional material that catalyzes condensation of the halogenated hydrocarbon.
  • Hydrocarbon oligomerization (defined as carbon-carbon coupling) takes place within this zone of the reactor and yields product hydrocarbons which, in general, will have carbon numbers ranging from C 2 to C 20 , and may include alkanes, alkenes, alkynes, and/or aromatics.
  • Treatment with air or oxygen liberates halogen for use in subsequent halogenation steps, and regenerates the cataloreactant material for subsequent condensation or metathesis.
  • the need for recycling/recovering corrosive, aqueous hydrohalic acid is avoided because regeneration and recovery takes place in situ.
  • Higher hydrocarbon synthesis begins with a hydrocarbon feedstock: one or more reactant hydrocarbons, each having, independently, a carbon number C m , where m ⁇ n, C n being the carbon number of the target hydrocarbon(s).
  • reactant hydrocarbons include methane, ethane, propane, etc., with natural gas (predominately methane, but often including small amounts of C 2 and higher species) being preferred.
  • the starting hydrocarbon has a carbon number between 1 and 10. Mixtures of hydrocarbons may also be used.
  • the reactant hydrocarbons are allowed to react with a halogenating agent.
  • a halogenating agent include molecular halogen (e.g., bromine, chlorine, etc.), alkyl halides (e.g., dibromomethane, bromoform, carbon tetrabromide), and condensed halides, such as metal bromides, which may be present as a solid, liquid, supported, or unsupported material.
  • Molecular halogens are preferred, with bromine (Br 2 ) being most preferred.
  • Bromine is a liquid at room temperature, less reactive than chlorine and fluorine, and easy to handle. Bromine also has favorable energetics.
  • Halogenation of the reactant hydrocarbon may proceed in a number of ways, depending in part on the desired product(s) and in part on the feed.
  • an alkane is halogenated with molecular halogen using heat, light, or other electromagnetic radiation to drive the reaction, with heat being preferred.
  • heat is preferred.
  • temperatures of from 375 to 450° C. are utilized, with the range being important, if not critical.
  • an ideal temperature range where all steps occur at roughly the same temperature, is 450 to 550° C.
  • individual reaction steps might be carried out at temperatures above or below this range.
  • Halogenation preferably occurs at a pressure between 0.1 and 200 atm, for the subsequent carbon-carbon step.
  • Low pressure favors less carbon-carbon coupling (i.e., a smaller average molecular weight of product), while high pressure favors higher coupling.
  • Processes for light olefins are likely to run at the same 60 to 200 psia that methanol to olefin (MTO) processes are run at, although higher pressures may alternatively be utilized.
  • MTO methanol to olefin
  • pressures around 350 psia, as used in methanol to gasoline (MTG) processes are envisioned. As a practical matter, running below atmospheric (more conservatively, below 2 psia) or above 100 atm is unlikely.
  • halogenation ideally is carried out at an alkane:halogen ratio of between 1:10 and about 100:1, on a volume by volume basis.
  • alkane:halogen ratios of less than 1:10 (i.e., more halogen)
  • multi-halogenated hydrocarbons will be formed, typically leading to complete oxidation (i.e., CO 2 ) upon subsequent contact with the metal-oxygen cataloreactant.
  • alkane:halogen ratios higher than 100:1 the conversion to a halogenated hydrocarbon will be too low, perhaps 1% or less, and it is nearly impossible to imagine an economical process at such conversion levels. (30-60% conversion are more likely lower limits).
  • Altering the ratio of halogen to alkane or other hydrocarbon feedstock may have a marked impact on product distribution. For example, one may choose to control the degree of halogenation in order to reduce aromatic formation in the production of lower olefins or fuels. A second example is minimizing formation of highly halogenated methane in order to reduce the formation of alkynes.
  • a key feature of the invention is the use of a metal-oxygen cataloreactant, which facilitates carbon-carbon coupling, i.e., hydrocarbon oligomerization.
  • metal-oxygen cataloreactant is used herein to refer to a cataloreactant material containing both metal and oxygen. While not bound by theory, it is believed that the material catalyzes carbon-carbon coupling via hydrogen halide (e.g., HBr) elimination and alkylidene insertion into cationically activated C—H and possibly C—C bonds.
  • the cataloreactant also acts as a halogen release and sequestering agent, and offers the possibility of obtaining a tunable coupling product distribution, including the ability to produce oxygenates if desired, while simultaneously trapping and recovering halogen, emitting only water as a byproduct. Treatment with air or oxygen regenerates the cataloreactant.
  • Nonlimiting examples of metal-oxygen cataloreactants include zeolites, doped zeolites, metal oxides, mixed metal oxides, metal oxide-impregnated zeolites, and similar materials, as well as mixtures of such materials.
  • Nonlimiting examples of dopants include calcium and magnesium, and their oxides and/or hydroxides.
  • Zeolites are available from a variety of sources, including Zeolyst International (Valley Forge, Pa.). Specific examples include doped-ZSM-5 and doped mordenite (where, e.g., calcium and/or magnesium are the dopants).
  • Pore size and acidity are particularly expected to be important. Acidity may be used to control chain length and functionality, and pore size may control chain length and functionality. Zeolites of particular pore-size may selectively produce benzene, toluene, para-xylene, ortho-xylene, meta-xylene, mixed xylenes, ethyl benzene, styrene, linear alkyl benzene, or other aromatic products. The use of pore size is not limited to aromatic products.
  • a metal oxide/zeolite composite is prepared by mixing a zeolite with a metal nitrate (e.g., calcium nitrate) or hydrated species thereof.
  • a metal nitrate e.g., calcium nitrate
  • the metal-oxygen cataloreactant is regenerated by treatment with air or oxygen, typically at a temperature of from 200 to 900° C. This converts metal halide species into metal-oxygen species.
  • a number of variables, including feed composition, feed location in the reactor, temperature, pressure, metal oxide composition, and reactor residence time may alter the product distribution.
  • Production of alkanes, olefins and aromatics from methane has been detected and confirmed. Also expected is the ability to produce alkanes and olefins of particular branching (including mono-methyl branched alcohols), alcohols, diols, ethers, halogenated hydrocarbons, aromatics including benzene, styrene, ethyl benzene, toluene, xylenes, and linear alkyl benzenes, and hydrocarbons suitable for fuels such as gasoline, diesel, and jet fuel.
  • Control of the feed composition can control the product distribution.
  • hydrogen halide produced in the halogenation may be neutralized (to form water or alcohol) with the same metal-oxygen compound producing the hydrocarbon product(s), or with a separate metal-oxygen compound in a distinct reactor. Shifting the hydrogen halide neutralization location may shift the product distribution, including functionality, chain length, and branching. For example, concurrent neutralization and product formation may be expected to drive the production of alcohols, which may or may not undergo further reactions such as coupling or dehydration.
  • water addition to the feed may shift product distribution. In particular, the addition of water may favor alcohol products. The addition of water may also control degree and type of branching and chain length.
  • hydrogen addition may alter the product distribution. Hydrogen may increase alkanes at the expense of other functionalities, something particularly useful for producing fuels. Hydrogen may also reduce coking and help control the chain length and branching.
  • carbon-carbon oligomerization may proceed by a number of pathways. Even single-hydrocarbon feedstocks may yield more than one product.
  • controlled halogentation is used to produce predominately one isomer in favor of another (e.g., selective formation of 1-butene or 2-butene).
  • Mixed feedstocks such as raw natural gas, may give rise to oligomerization of multiple halogenated hydrocarbons (e.g., ethyl halide, dihaloethane, methyl halide, methyl dihalide, propyl halide, propyl dihalide, etc.).
  • an alkyl halide is purposefully introduced to create desired branched products.
  • An example would be oligomerization of methyl halide (from methane) with ethyl halide or a higher alkyl halide to produce, selectively, methyl, ethyl, propyl, isopropyl, or tertiary butyl (or other) branching.
  • Another example might be the synthesis of styrene from ethyl halide, methyl halide, and dihalomethane.
  • the reaction of halogenated hydrocarbon with a metal-oxygen cataloreactant takes place in a fluidized bed.
  • a fixed bed is employed.
  • Different alkyl halides may be introduced at different locations in the reactor.
  • One example is the introduction of methyl halides at one location in a reactor to produce benzene, to which ethyl halides are added, producing styrene or ethyl benzene.
  • Another example is the introduction of methyl halides at one location in a reactor to produce benzene, to which alkyl halides are added, producing linear alkyl benzene.
  • Product separation is accomplished by any suitable method. Nonlimiting examples include distillation, adsorption, and extraction. Product(s) may be recovered from the solid by stripping with steam, carbon dioxide, or other means.
  • Methane at 15 psia was bubbled through bromine at 1° C. at a rate of 5 cc/min.
  • the output stream from the second reactor contained no brominated products. Based on the methane consumed in the bromination reactor, 10% ethylene, 31% propylene, 3% propane, and 21% butanes/butenes were detected; 65% overall. Trace amounts of C 6 species were also detected.
  • a doped mordenite (Zeolyst CBV 21A, doped with both Ca and Mg). (5 g) was prepared according to Example 1, and used as the cataloreactant in a hydrocarbon synthesis substantially similar to that described above in Example 2. The product output was 30% ethylene, 5% ethane, 10% propylene, 3% propane, 5% butanes/butenes. Multiple runs and cataloreactant regeneration established reproducibility.
  • oligomerization processes described herein are also intended to encompass halogenation of olefin feedstocks using a hydrogen halide (e.g., HBr) or molecular halogen; halogenation of acetylenes (alkynes) using hydrogen halide or molecular halogen; halogenation of alcohols or ethers using hydrogen halide or molecular halogen; and halogenation of alkanes using molecular halogen and a catalyst that controls the halogenation.
  • a hydrogen halide e.g., HBr
  • halogenation of acetylenes (alkynes) using hydrogen halide or molecular halogen halogenation of alcohols or ethers using hydrogen halide or molecular halogen
  • alkanes using molecular halogen and a catalyst that controls the halogenation.
  • the catalyst may control one or both of the degree of halogenation (number of halogens per molecule) and the position of halogenation (e.g. terminal vs. internal halogenation for a long chain alkane).
  • degree of halogenation number of halogens per molecule
  • position of halogenation e.g. terminal vs. internal halogenation for a long chain alkane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US10/893,418 2003-07-15 2004-07-15 Hydrocarbon synthesis Abandoned US20050038310A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US10/893,418 US20050038310A1 (en) 2003-07-15 2004-07-15 Hydrocarbon synthesis
US11/091,130 US20050171393A1 (en) 2003-07-15 2005-03-28 Hydrocarbon synthesis
US12/080,594 US20080188697A1 (en) 2003-07-15 2008-04-03 Hydrocarbon synthesis
US12/217,311 US7847139B2 (en) 2003-07-15 2008-07-02 Hydrocarbon synthesis
US12/683,607 US7964764B2 (en) 2003-07-15 2010-01-07 Hydrocarbon synthesis
US13/107,611 US8278493B2 (en) 2003-07-15 2011-05-13 Hydrocarbon synthesis

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US48736403P 2003-07-15 2003-07-15
US10/893,418 US20050038310A1 (en) 2003-07-15 2004-07-15 Hydrocarbon synthesis

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US12/217,311 Continuation US7847139B2 (en) 2003-07-15 2008-07-02 Hydrocarbon synthesis

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EP (1) EP1682465A1 (fr)
JP (2) JP2007525477A (fr)
AU (1) AU2004268935B2 (fr)
CA (1) CA2532367C (fr)
MX (1) MXPA06000470A (fr)
NO (1) NO20060166L (fr)
RU (1) RU2366642C2 (fr)
WO (1) WO2005021468A1 (fr)

Cited By (17)

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US20050234276A1 (en) * 2004-04-16 2005-10-20 Waycuilis John J Process for converting gaseous alkanes to liquid hydrocarbons
US20060100469A1 (en) * 2004-04-16 2006-05-11 Waycuilis John J Process for converting gaseous alkanes to olefins and liquid hydrocarbons
WO2007107031A1 (fr) * 2006-03-23 2007-09-27 Eth Zurich Production d'hydrocarbures saturés en c2 à c5
US20080275284A1 (en) * 2004-04-16 2008-11-06 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
WO2008148113A1 (fr) * 2007-05-24 2008-12-04 Grt, Inc. Réacteur à zones comprenant la capture et la libération réversibles d'halogénure d'hydrogène
US20090247796A1 (en) * 2004-04-16 2009-10-01 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US20090308759A1 (en) * 2008-06-13 2009-12-17 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US20110218374A1 (en) * 2010-03-02 2011-09-08 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8536393B2 (en) 2009-05-13 2013-09-17 Shell Oil Company Integrated process to produce C4+ hydrocarbons with removal of brominated organic impurities
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems

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US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US20050171393A1 (en) * 2003-07-15 2005-08-04 Lorkovic Ivan M. Hydrocarbon synthesis
US20050038310A1 (en) 2003-07-15 2005-02-17 Lorkovic Ivan M. Hydrocarbon synthesis
EP1735255A4 (fr) * 2004-04-16 2012-01-04 Marathon Gtf Technology Ltd Procede de conversion d'alcanes gazeux en hydrocarbures liquides
US20060229228A1 (en) * 2005-04-11 2006-10-12 Zachary John Anthony Komon Method of making alkoxylates
KR101335397B1 (ko) 2006-02-03 2013-12-02 지알티, 인코포레이티드 할로겐으로부터 가벼운 기체를 분리하는 방법
NZ588129A (en) 2006-02-03 2012-06-29 Grt Inc Continuous process for converting natural gas to liquid hydrocarbons
EA201200888A1 (ru) * 2007-05-14 2013-02-28 Грт, Инк. Способ конверсии углеводородного сырья с электролитическим извлечением галогенов
KR101740419B1 (ko) 2008-07-18 2017-05-26 지알티, 인코포레이티드 천연 가스를 액체 탄화수소로 변환시키는 연속 공정
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RU2366642C2 (ru) 2009-09-10
WO2005021468A1 (fr) 2005-03-10
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JP2007525477A (ja) 2007-09-06
US20080269534A1 (en) 2008-10-30
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JP2012092134A (ja) 2012-05-17
NO20060166L (no) 2006-04-05

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