GB632820A - Improvements in or relating to the production of organic compounds by chemical transformation of methane or its sulfonated and/or oxygenated derivatives - Google Patents

Improvements in or relating to the production of organic compounds by chemical transformation of methane or its sulfonated and/or oxygenated derivatives

Info

Publication number
GB632820A
GB632820A GB13401/47A GB1340147A GB632820A GB 632820 A GB632820 A GB 632820A GB 13401/47 A GB13401/47 A GB 13401/47A GB 1340147 A GB1340147 A GB 1340147A GB 632820 A GB632820 A GB 632820A
Authority
GB
United Kingdom
Prior art keywords
methane
methanol
products
hydrolysis
sulphonic acid
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
GB13401/47A
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.)
Houdry Process Corp
Original Assignee
Houdry Process Corp
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
Application filed by Houdry Process Corp filed Critical Houdry Process Corp
Publication of GB632820A publication Critical patent/GB632820A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/48Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide

Abstract

Sulphur trioxide and methane are reacted at 100-450 DEG C. under superatmospheric pressure and one or more of the following separated from the products: methanol, methyl sulphates, methane sulphonic acid and methionic acid, and their methyl esters. Preferably a sulphonation catalyst is used such as a Group 2B metal, particularly mercury, or a sulphate thereof. Pressures are generally below 5000, e.g. 100-2500 p.s.i. Natural gas or other gas consisting mainly of methane with some ethane may be used. Sulphur oxides may be separated from the products for re-use, if necessary after oxidizing the dioxide to trioxide. Condensation or distillation of the products admits of separation thereof or hydrolysis by steam distillation yields methanol or its esters and a residue yielding sulphonic acids. Methane sulphonic acid or its ester may be pyrolyzed at 225-500 DEG C., for example by refluxing at 325 DEG C., with addition of water if required, to give methanol. Disulphonated derivatives of methane may be converted to methanol, for example, by hydrolysis to methane sulphonic acid and sulphuric acid, and pyrolysis of the former. Methanol or dimethyl ether obtained from the reaction products may be subjected to the action of dehydrating and condensing agents such as metallic polyhalides, whose hydrolysis may be suppressed by addition of gaseous halides, such as halides of zinc, cadmium or thorium, particularly zinc chloride. At preferred temperatures of 375-650 DEG C., and pressures below 5000 p.s.i., hydrocarbons of 4 or more carbon atoms including aromatics are obtained. Isobutane or other isoparaffins, and olefins, may be separated and used to produce alkylates or polymers. In examples, methane and sulphur trioxide are reacted alone or in presence of mercury sulphate, at temperatures between 230 DEG and 300 DEG C., and pressures of 820-1350 p.s.i., molar ratios of SO3 : CH4 being from 0.59 to 10. Methanol obtained by hydrolysis of the products is heated with zinc chloride to give branched lower hydrocarbons, and hexamethylbenzene. The Specification as open to inspection under Sect. 91 comprises also the pyrolysis of methane sulphonic acid and the dehydration, condensation of methanol or dimethyl ether, however said initial materials are prepared, and includes additional examples thereof. This subject-matter does not appear in the Specification as accepted.
GB13401/47A 1946-05-31 1947-05-19 Improvements in or relating to the production of organic compounds by chemical transformation of methane or its sulfonated and/or oxygenated derivatives Expired GB632820A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US632820XA 1946-05-31 1946-05-31

Publications (1)

Publication Number Publication Date
GB632820A true GB632820A (en) 1949-12-05

Family

ID=22048171

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13401/47A Expired GB632820A (en) 1946-05-31 1947-05-19 Improvements in or relating to the production of organic compounds by chemical transformation of methane or its sulfonated and/or oxygenated derivatives

Country Status (1)

Country Link
GB (1) GB632820A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10132526A1 (en) * 2001-07-09 2003-01-30 Ruhrgas Ag Production of alkane derivatives from alkane, especially methanol from methane, involves oxidative reaction with sulfur trioxide to form alkyl sulfate, reaction with auxiliary acid and separation of the resulting ester
EP1558353A2 (en) * 2002-11-05 2005-08-03 Alan K. Richards Anhydrous conversion of methane and other light alkanes into methanol and other derivatives, using radical pathways and chain reactions with minimal waste products
US7282603B2 (en) 2003-06-21 2007-10-16 Richards Alan K Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds
WO2009017925A1 (en) * 2007-07-27 2009-02-05 Dow Global Technologies Inc. Process for selective, partial, substantially solvent-free, oxidation of methane to methanol and/or a methanol derivative with a heterogeneous catalyst and sulfur trioxide
RU2496772C1 (en) * 2012-08-06 2013-10-27 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "ДАГЕСТАНСКИЙ ГОСУДАРСТВЕННЫЙ УНИВЕРСИТЕТ" Method of producing methanesulphonic acid
WO2018219726A1 (en) * 2017-05-30 2018-12-06 Basf Se Process for the production of alkanesulfonic acids

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10132526A1 (en) * 2001-07-09 2003-01-30 Ruhrgas Ag Production of alkane derivatives from alkane, especially methanol from methane, involves oxidative reaction with sulfur trioxide to form alkyl sulfate, reaction with auxiliary acid and separation of the resulting ester
EP1558353A4 (en) * 2002-11-05 2010-03-10 Alan K Richards Anhydrous conversion of methane and other light alkanes into methanol and other derivatives, using radical pathways and chain reactions with minimal waste products
EP1558353A2 (en) * 2002-11-05 2005-08-03 Alan K. Richards Anhydrous conversion of methane and other light alkanes into methanol and other derivatives, using radical pathways and chain reactions with minimal waste products
US7282603B2 (en) 2003-06-21 2007-10-16 Richards Alan K Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds
US8242300B2 (en) 2007-07-27 2012-08-14 Dow Global Technologies Llc Process for selective, partial, substantially solvent-free, oxidation of methane to methanol and/or a methanol derivative with a heterogeneous catalyst and sulfur trioxide
CN101808967A (en) * 2007-07-27 2010-08-18 陶氏环球技术公司 Adopt heterogeneous catalyst and sulphur trioxide with methane selectively, solvent-freely be oxidized to the method for methyl alcohol and/or carbinol derivatives partly, basically
WO2009017925A1 (en) * 2007-07-27 2009-02-05 Dow Global Technologies Inc. Process for selective, partial, substantially solvent-free, oxidation of methane to methanol and/or a methanol derivative with a heterogeneous catalyst and sulfur trioxide
CN101808967B (en) * 2007-07-27 2014-05-07 陶氏环球技术有限责任公司 Process for selective, partial, substantially solvent-free, oxidation of methane to methanol and/or a methanol derivative with a heterogeneous catalyst and sulfur trioxide
RU2496772C1 (en) * 2012-08-06 2013-10-27 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "ДАГЕСТАНСКИЙ ГОСУДАРСТВЕННЫЙ УНИВЕРСИТЕТ" Method of producing methanesulphonic acid
WO2018219726A1 (en) * 2017-05-30 2018-12-06 Basf Se Process for the production of alkanesulfonic acids
CN110678444A (en) * 2017-05-30 2020-01-10 巴斯夫欧洲公司 Process for producing alkanesulfonic acids
US10894766B2 (en) 2017-05-30 2021-01-19 Basf Se Process for the production of alkanesulfonic acids
CN110678444B (en) * 2017-05-30 2023-01-10 巴斯夫欧洲公司 Process for producing alkanesulfonic acid

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