GB1104294A - Production of lower alkanols and lower alkyl bromides - Google Patents
Production of lower alkanols and lower alkyl bromidesInfo
- Publication number
- GB1104294A GB1104294A GB4873363A GB4873363A GB1104294A GB 1104294 A GB1104294 A GB 1104294A GB 4873363 A GB4873363 A GB 4873363A GB 4873363 A GB4873363 A GB 4873363A GB 1104294 A GB1104294 A GB 1104294A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromide
- hydrogen bromide
- bromine
- carried out
- catalyst
- 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
Links
Classifications
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A C1-C8 alkyl bromide is produced from the corresponding alkane by reacting an excess of the alkane with bromine at elevated temperature to produce the bromide and hydrogen bromide, separating the hydrogen bromide, recovering the alkyl bromide, oxidizing the hydrogen bromide to produce bromine and recycling the bromine to the bromination step. If desired the alkyl bromide may be hydrolysed with water or steam at elevated temperature to give the corresponding alkanol and hydrogen bromide, and the hydrogen bromide separated and oxidized to bromine which is recycled to the bromination step. The bromination step is preferably carried out at 80-450 DEG C. and 1-200 atm. absolute and may be carried out in the presence of a catalyst, e.g. tetraethyl lead or other catalyst generating free radicals, ultraviolet light or a silent electric discharge. The oxidation of the hydrogen bromide may be carried out by molecular oxygen or nitric acid. If oxygen is used, e.g. in the form of air, a catalyst such as nitric acid, nitric oxide, a nitrate or nitrite is preferably also present.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4873363A GB1104294A (en) | 1963-12-10 | 1963-12-10 | Production of lower alkanols and lower alkyl bromides |
| DE19641468781 DE1468781A1 (en) | 1963-12-10 | 1964-11-25 | Production of lower alkanols and lower alkyl bromides |
| FR997838A FR1418479A (en) | 1963-12-10 | 1964-12-08 | Improvements in processes for the production of lower alkanols and lower alkyl bromides |
| BE656849D BE656849A (en) | 1963-12-10 | 1964-12-09 | |
| NL6414356A NL6414356A (en) | 1963-12-10 | 1964-12-10 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4873363A GB1104294A (en) | 1963-12-10 | 1963-12-10 | Production of lower alkanols and lower alkyl bromides |
| GB2966364 | 1964-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1104294A true GB1104294A (en) | 1968-02-21 |
Family
ID=26260016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4873363A Expired GB1104294A (en) | 1963-12-10 | 1963-12-10 | Production of lower alkanols and lower alkyl bromides |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE656849A (en) |
| DE (1) | DE1468781A1 (en) |
| GB (1) | GB1104294A (en) |
| NL (1) | NL6414356A (en) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1983000859A1 (en) * | 1981-09-01 | 1983-03-17 | George Andrew Olah | Methyl halides and methyl alcohol from methane |
| GB2120249A (en) * | 1982-05-15 | 1983-11-30 | British Petroleum Co Plc | Process for the production of methyl or ethyl mono-halide |
| US4523040A (en) * | 1981-09-01 | 1985-06-11 | Olah George A | Methyl halides and methyl alcohol from methane |
| US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US7579510B2 (en) | 2006-02-03 | 2009-08-25 | Grt, Inc. | Continuous process for converting natural gas to liquid hydrocarbons |
| 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 |
| 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 |
| 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 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990696A (en) * | 1988-12-29 | 1991-02-05 | Stauffer John E | Methyl alcohol process |
| US5185479A (en) * | 1992-04-21 | 1993-02-09 | Stauffer John E | Process for methyl alcohol |
-
1963
- 1963-12-10 GB GB4873363A patent/GB1104294A/en not_active Expired
-
1964
- 1964-11-25 DE DE19641468781 patent/DE1468781A1/en active Pending
- 1964-12-09 BE BE656849D patent/BE656849A/xx unknown
- 1964-12-10 NL NL6414356A patent/NL6414356A/xx unknown
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4523040A (en) * | 1981-09-01 | 1985-06-11 | Olah George A | Methyl halides and methyl alcohol from methane |
| WO1983000859A1 (en) * | 1981-09-01 | 1983-03-17 | George Andrew Olah | Methyl halides and methyl alcohol from methane |
| GB2120249A (en) * | 1982-05-15 | 1983-11-30 | British Petroleum Co Plc | Process for the production of methyl or ethyl mono-halide |
| US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
| US8415512B2 (en) | 2001-06-20 | 2013-04-09 | Grt, Inc. | Hydrocarbon conversion process improvements |
| US7964764B2 (en) | 2003-07-15 | 2011-06-21 | Grt, Inc. | Hydrocarbon synthesis |
| US7847139B2 (en) | 2003-07-15 | 2010-12-07 | Grt, Inc. | Hydrocarbon synthesis |
| 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 |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| US7880041B2 (en) | 2004-04-16 | 2011-02-01 | Marathon Gtf Technology, Ltd. | Process for converting gaseous alkanes to liquid hydrocarbons |
| US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US7560607B2 (en) | 2004-04-16 | 2009-07-14 | Marathon Gtf Technology, Ltd. | Process for converting gaseous alkanes to liquid hydrocarbons |
| 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 |
| US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US7348464B2 (en) | 2004-04-16 | 2008-03-25 | Marathon Oil Company | 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 |
| US7579510B2 (en) | 2006-02-03 | 2009-08-25 | Grt, Inc. | Continuous process for converting natural gas to liquid hydrocarbons |
| 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 |
| US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US9133078B2 (en) | 2010-03-02 | 2015-09-15 | Gtc Technology Us, Llc | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1468781A1 (en) | 1969-05-08 |
| NL6414356A (en) | 1965-06-11 |
| BE656849A (en) | 1965-06-08 |
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