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(12) Patent Application Publication (10) Pub. No.: US 2008/0314758 A1 Gross0 Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2008/0314758 A1 Gross0 Et Al US 20080314758A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0314758 A1 Gross0 et al. (43) Pub. Date: Dec. 25, 2008 (54) PROCESS FOR CONVERTING Related U.S. Application Data HYDROCARBON FEEDSTOCKS WITH ELECTROLYTC RECOVERY OF HALOGEN (60) Provisional application No. 60/930,220, filed on May 14, 2007. (75) Inventors: Philip Grosso, Auburn, CA (US); Publication Classification Eric W. McFarland, Santa Barbara, (51) Int. Cl CA (US); Jeffrey H. Sherman, we WE FL C25B 3/06 (2006.01) s C25B 3/00 (2006.01) Correspondence Address: (52) U.S. Cl. .......... 205/431; 205/462; 205/451; 204/277 CHRISTIE, PARKER & HALE, LLP (57) ABSTRACT PO BOX 7O68 PASADENA, CA 91109–7068 (US) An improved continuous process for converting methane, natural gas, and other hydrocarbon feedstocks into one or more higher hydrocarbons, methanol, amines, or other prod (73) Assignee: GRT, INC. ucts comprises continuously cycling through hydrocarbon halogenation, product formation, product separation, and (21) Appl. No.: 12/152,515 electrolytic regeneration of halogen, optionally using an improved electrolytic cell equipped with an oxygen depolar (22) Filed: May 14, 2008 ized cathode. NATURAL GAS w RECYCLE & WENT 24 WET BROMINE HYDROGEN BROMINATION --2O 18-- - -- 17 ELECTROLYSIs s 19 COOLER CELS C ACID/BASE FOR pH CONTROL AQUEOUS NaBr A. AQUEOUS NaOH/NaBr ORGANICS 15- -13 14 HBr ABSORPTION NaBr- ORGANICS Aoys & 12- PRODUCT RECOVERY SEPARATION NCS PRODUCT Patent Application Publication Dec. 25, 2008 Sheet 1 of 11 US 2008/0314758A1 © Patent Application Publication Dec. 25, 2008 Sheet 3 of 11 US 2008/0314758A1 IyyanLy?ISwºTV80LVNSºº Patent Application Publication Dec. 25, 2008 Sheet 4 of 11 US 2008/0314758 A1 3)--CEDOGZ -- - - - - - - - - - - - - - - - - - - - - - - - - - Patent Application Publication Dec. 25, 2008 Sheet 5 of 11 US 2008/0314758 A1 Patent Application Publication US 2008/0314758A1 OO+,N ZÓI,H. OO}})TvO'BHOOLOGIE-OJ,S[\OQN||NOOT\/>''OèHO-SSEOZH9+Bxoº<--SNº:10-TE --Woo Patent Application Publication Dec. 25, 2008 Sheet 8 of 11 US 2008/0314758A1 uGHb+bugt-,HXO HODNbz+ cae TWOOÈHOHSSBOOÀ?dTWO|WEHOOLOETE–OH)),SnOnNLINOO “H+STOHOOTv-ATOds--SNOJIOETH+ssºwoladonºoo HODNÁz+?ugb+,Hb ÕHb SNO}}|OBTIEDZ Patent Application Publication Dec. 25, 2008 Sheet 10 of 11 US 2008/0314758A1 SGÏO=L‘O),007=|• %/°/6°NOIS(BANOOugºHO• ()/(f)I,H. 90—||O %O’||Z. Patent Application Publication Dec. 25, 2008 Sheet 11 of 11 US 2008/0314758A1 %00INOISèJEANOOugºHO• S0’G=L‘O),GZ7=|• //(f)I,H. 9O-ZO ?”,„g CITE!),24 46 O| +QW ég.V US 2008/0314758 A1 Dec. 25, 2008 PROCESS FOR CONVERTING 0007 Typically, the reforming process is coupled with HYDROCARBON FEEDSTOCKS WITH complete oxidation to provide energy to drive the otherwise ELECTROLYTC RECOVERY OF HALOGEN endothermic reaction. The resulting overall reaction produces both carbon oxides and hydrogen and can be operated nearly CROSS REFERENCE TO RELATED isoergically: APPLICATION 0001. This application claims the benefit of priority to U.S. Provisional Application No. 60/930,220, filed May 14, 0008 Alternatively, hydrogen can be produced by disso 2007, the entire contents of which are incorporated by refer ciation of water: ence herein. 0009. Although energetically unfavorable, the reaction FIELD OF THE INVENTION can be driven by electrolysis using 2x10 Coulombs per 0002 The present invention is directed to a process for gram-mole H. Water is the source of both the hydrogen and converting natural gas and other hydrocarbon feedstocks into the oxygen, and the high activation energy for oxygen pro higher-value products, such as fuel-grade hydrocarbons, duction requires over potentials of approximately 1.6 Volts methanol, and aromatic compounds. and a stoichiometric current. In practice, the electrical energy required is approximately 300 kJ/mol H. BACKGROUND OF THE INVENTION 0010 Inhalogen production by electrolysis of halide salts, e.g. the chloralkali process, halogen (Cl) and alkali base 0003 U.S. patent application Ser. No. 1 1/703,358 (“the (NaOH) are produced from the haloanion and water in an 358 application.”), entitled “Continuous Process for Con aqueous solution of salt (NaCl). Water is again the source of verting Natural Gas to Liquid Hydrocarbons', filed Feb. 5, the hydrogen. Similarly, bromine can be produced from bro 2007, based on U.S. Provisional Application No. 60/765,115, mine salts (NaBr). In the latter instance, the production of filed Feb. 3, 2006, describes a continuous process for reacting molecular halogen from the haloanion is energetically and molecular halogen with a hydrocarbon feedstock to produce kinetically advantageous compared to oxygen production, higher hydrocarbons. In one embodiment, the process requiring a lower over potential (1.1 V versus 1.6V): includes the steps of alkane halogenation, “reproportion ation of polyhalogenated compounds to increase the amount of monohalides that are formed, oligomerization (C-C cou 10011. With 2x10 Coulombs per gram-mole H, and the pling) of alkyl halides to form higher carbon number prod required electrical energy reduced significantly (compared to ucts, separation of products from hydrogen halide, continu H2O alone) to approximately 200 kJ/g mol H. ous regeneration of halogen, and recovery of molecular 0012 Many attempts have been made to develop eco halogen from water. Hydrohalic acid (e.g., HBr) is separated nomically viable hydrogen production processes. In prin from liquid hydrocarbons in a liquid-liquid phase splitter, and ciple, hydrocarbons can be directly oxidized electrochemi then converted into molecular halogen (e.g., bromine) by cally using oxygen (as in a solid oxide fuel cell) and/or water reaction with a source of oxygen in the presence of a metal to produce hydrogen; however this typically leads to com oxide catalyst. The 358 application is incorporated by refer plex, difficult to separate intermediates and is not economi ence herein in its entirety. cally useful. Another means of removing hydrogen from 0004. The 358 application represents a significant hydrocarbons is by stepwise partial oxidation with a halogen, advance in the art of C–H bond activation and industrial processes for converting a hydrocarbon feedstock into higher (preferably bromine). The major advantage is that complete value products. The present invention builds on the 358 oxidation of hydrocarbon to carbon dioxide cannot occur and application by employing electrolysis to regenerate molecu the hydrogen is transferred to the less stable HBr (AH, lar halogen (e.g., Br, Cl) from hydrohalic acid (e.g., HBr, tion -36 kJ/mol), rather than water (AH, -286 HCl). kJ/mol): 0005 Electrolysis of aqueous solutions to produce hydro gen and oxygen is a known way of producing hydrogen with electrical energy. Similarly, halogens have been produced by electrolysis of halide brines or metal halide vapor. Conven 0013 Final products after removal of HBr depend on the tional hydrogen production relies on reforming of hydrocar reaction conditions and may consist of mixtures of coke and bons with water (steam) to produce carbon monoxide and brominated and perbrominated hydrocarbons: C+C.HBr,+ molecular hydrogen: C.Br. Combustion of these final products in an oxygen atmo sphere containing trace water may be used to produce heat and carbonoxides and to convert the residual bromine to HBr: 0006. The energetically unfavorable reforming reaction can be compared to the exothermic complete oxidation of 0014. Another process for making hydrogen, based on hydrocarbons in oxygen to produce the low-energy products HBr electrolysis, reportedly yields energy savings of about water and carbon dioxide: 25% relative to water electrolysis. However, this process requires that bromine produced in electrolysis be converted back to HBr, and this conversion step is a major disadvantage of the HBr electrolysis route to hydrogen. In contrast, the US 2008/0314758 A1 Dec. 25, 2008 present invention uses the bromine generated in electrolysis and base such that more than sufficient alkali is available to to produce valuable products, rather than simply converting it react with the alkyl bromides to achieve alkaline conditions. back to HBr, The acid removed in the disproportionation step is later recombined with the excess alkali after methanol and other SUMMARY OF THE INVENTION products have been formed and separated. 0015 The present invention combines the thermal (non 0019. In some embodiments it may be necessary to main electrochemical) reactivity of halogens (preferably bromine) tain the anolyte in acidic condition, which may require a small with hydrocarbons to produce hydrogen halide (preferably amount of acid to be added. The separation of a portion of the HBr) and reactive alkyl halides or other carbon-containing acid can be accomplished by a liquid phase process or, alter intermediates that may be converted to Subsequent products, natively, by the use of a regenerable solid reactant or adsor more readily than the original hydrocarbon, with the facile bent. Acid can also be provided from an external source, electrolysis of hydrogen halides or halide Salts to create an either from on-site or off-site generation. Alternatively, an overall process with significantly higher efficiency. The use overall excess of acid can be achieved by removal of a small of halogens prevents the total oxidation of the hydrocarbon to amount of alkali from the system. carbon dioxide and allows Subsequent production of partial 0020. In a third aspect of the invention, a continuous pro oxidation products. cess for
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