GB796085A - Hydrocarbon conversion process - Google Patents

Hydrocarbon conversion process

Info

Publication number
GB796085A
GB796085A GB2487556A GB2487556A GB796085A GB 796085 A GB796085 A GB 796085A GB 2487556 A GB2487556 A GB 2487556A GB 2487556 A GB2487556 A GB 2487556A GB 796085 A GB796085 A GB 796085A
Authority
GB
United Kingdom
Prior art keywords
benzene
olefine
iodine
naphthalene
used
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.)
Expired
Application number
GB2487556A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to US796085XA priority Critical
Application filed by Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB796085A publication Critical patent/GB796085A/en
Application status is Expired legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/42Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
    • C07C5/54Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an acceptor system containing at least two compounds provided for in more than one of the sub-groups C07C5/44 - C07C5/50

Abstract

Hydrocarbons containing at least three carbon atoms and non-aromatic carbon-to-hydrogen bonds are converted into hydrocarbons containing a new carbon-to-carbon linkage and having a higher carbon to hydrogen ratio by heating with an hydrogen-accepting olefine and a proportion of iodine (or hydrogen iodide, alkyl iodides or other compound which liberates iodine under the reaction conditions) of at least 0.05 mol. per mol. of hydrocarbon to be converted at at least 300 DEG C. to effect carbonto-hydrogen bond cleavage in the hydrocarbon feed and convert the olefine to paraffin. Conversions which may be effected are dehydrogenation of alkanes or aralkanes, e.g. isobutane to isobutene, n-butane to butenes and butadiene, ethyl benzene to styrene, o-methyl ethyl benzene to o-methyl styrene, and n-butyl benzene to 4 - phenyl - butadiene - 1,3; dehydrocoupling, e.g. propylene to diallyl, isobutene to dimethallyl, toluene to dibenzyl and stilbene; dehydrocyclization often with aromatization, e.g. n-hexane to benzene, n-heptane to toluene, n-octane to m-xylene and ethyl benzene, 2,5-dimethyl hexane to p-xylene, hexadiene-1,3 to benzene, hexane-1 to cyclohexene, o-diethylbenzene to naphthalene, o-methyl propyl benzene to naphthalene, n-butyl benzene to naphthalene, 2,3-diethyl naphthalene to anthracene, butylcyclohexane to naphthalene, and butylcyclopentane to indene; and dehydrogenation, often with aromatization of hydroaromatic hydrocarbons, e.g. cyclohexane to cyclohexene and benzene, and methylcyclohexane to toluene. In the case of acyclic hydrocarbons containing a quaternary carbon atom, dealkylation and/or isomerization may occur, e.g. 2,2,5-trimethylhexane gives p- and m-xylenes. The olefine used should be such that the sum of the standard free energy change for the hydrogenation of the olefine to the corresponding paraffin and the standard free energy change for the conversion of the hydrocarbon, both measured at the desired reaction temperature, is a negative number. Ethylene is preferred being most suitable thermodynamically but higher olefines can be used, e.g. propylene, the butenes, pentenes and hexenes, particularly when aromatization occurs. In converting alkanes to alkenes or alkadienes, the olefine should have fewer carbon atoms and be of no greater degree of branching than the alkane. The olefine may be regenerated from the paraffin produced, e.g. by cracking and recycled to the reaction zone. It may be used mixed with other olefines and/or paraffins. The ratio of olefine to hydrocarbon feed employed expressed in theoretical equivalents (theories) may be 0.1 to 10. The total amount of iodine (or equivalent) added may be 0.1 to 0.8 theory; where an iodine compound is used some elemental iodine is also preferably added. Reaction temperatures of 400-600 DEG C., pressures of subatmospheric to 10 atmospheres and residence times of 0.01 second to 5 minutes may be used. In an example, n-butane is dehydrogenated to butenes and butadiene with varying amounts of iodine and ethylene using a small amount of helium as a diluent. Specifications 793,135, 793,214 and 793,215 are referred to.
GB2487556A 1955-12-22 1956-08-14 Hydrocarbon conversion process Expired GB796085A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US796085XA true 1955-12-22 1955-12-22

Publications (1)

Publication Number Publication Date
GB796085A true GB796085A (en) 1958-06-04

Family

ID=22151619

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2487556A Expired GB796085A (en) 1955-12-22 1956-08-14 Hydrocarbon conversion process

Country Status (1)

Country Link
GB (1) GB796085A (en)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US7847139B2 (en) 2003-07-15 2010-12-07 Grt, Inc. Hydrocarbon synthesis
US7880041B2 (en) 2004-04-16 2011-02-01 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US8008535B2 (en) 2004-04-16 2011-08-30 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US8053616B2 (en) 2006-02-03 2011-11-08 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8367884B2 (en) 2010-03-02 2013-02-05 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
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
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8415512B2 (en) 2001-06-20 2013-04-09 Grt, Inc. Hydrocarbon conversion process improvements
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US7847139B2 (en) 2003-07-15 2010-12-07 Grt, Inc. Hydrocarbon synthesis
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US7880041B2 (en) 2004-04-16 2011-02-01 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US8232441B2 (en) 2004-04-16 2012-07-31 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US8008535B2 (en) 2004-04-16 2011-08-30 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons
US8053616B2 (en) 2006-02-03 2011-11-08 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US8921625B2 (en) 2007-02-05 2014-12-30 Reaction35, LLC Continuous process for converting natural gas to liquid hydrocarbons
US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8415517B2 (en) 2008-07-18 2013-04-09 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US9133078B2 (en) 2010-03-02 2015-09-15 Gtc Technology Us, Llc Processes and systems for the staged synthesis of alkyl bromides
US8367884B2 (en) 2010-03-02 2013-02-05 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
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
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
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
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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