GB597634A - Improvements in or relating to the production of alkyl chlorides - Google Patents
Improvements in or relating to the production of alkyl chloridesInfo
- Publication number
- GB597634A GB597634A GB675244A GB675244A GB597634A GB 597634 A GB597634 A GB 597634A GB 675244 A GB675244 A GB 675244A GB 675244 A GB675244 A GB 675244A GB 597634 A GB597634 A GB 597634A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphuric acid
- chloride
- per cent
- treated
- esters
- 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
- 150000001348 alkyl chlorides Chemical class 0.000 title abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 9
- 235000011149 sulphuric acid Nutrition 0.000 abstract 7
- 239000001117 sulphuric acid Substances 0.000 abstract 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- -1 sulphuric acid ester Chemical class 0.000 abstract 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-Chlorobutane Chemical group CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 abstract 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-Chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 abstract 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N Isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 abstract 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N Isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- 229940038926 butyl chloride Drugs 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkyl chlorides are prepared by reacting gaseous hydrogen chloride with a sulphuric acid ester of an acyclic aliphatic alcohol containing not less than three carbon atoms in the molecule in the presence of water in an amount of not less than 8 per cent by weight calculated on the total sulphuric acid present in said ester or esters and as the free acid, if any, at a reaction temperature between room temperature and 60 DEG C. It is preferred to use sulphuric acid esters containing less than a molar proportion of alcohol per mole. of acid since free sulphuric acid accelerates the reaction. The spent liquids remaining after removal of the resulting alkyl chlorides may be reacted with acyclic aliphatic olefines having at least three carbon atoms to reform sulphuric acid esters which may be reacted as above with hydrogen chloride. A cyclic process comprises absorbing such olefines in sulphuric acid containing at least 8 per cent of water, treating the resulting alkyl sulphuric acid esters with hydrogen chloride, removing the alkyl chlorides formed and repeating the cycle with the spent liquor obtained. In examples: (1) secondary butyl alcohol is reacted with aqueous sulphuric acid yielding a mixture of sulphuric acid esters containing 16.3 per cent water and the mixture is treated with hydrogen chloride to form secondary butyl chloride; (2) propylene is absorbed in aqueous sulphuric acid and the resulting ester solution containing 11.3 per cent water treated as above giving isopropyl chloride; (3) the spent liquor from (2) is treated with further propylene and the resulting sulphuric esters treated as in (2); (4) n-butene is absorbed in 79 per cent sulphuric acid and the above-mentioned cyclic process carried out yielding isobutyl chloride. Amyl chloride may also be prepared by these methods. Specification 566,174 and U.S.A. Specification 2,284,467 are referred to. In the Provisional Specification the process is not limited as regards temperature.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB597634A true GB597634A (en) | 1948-01-30 |
Family
ID=1628724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB675244A Expired GB597634A (en) | 1944-04-12 | Improvements in or relating to the production of alkyl chlorides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB597634A (en) |
-
1944
- 1944-04-12 GB GB675244A patent/GB597634A/en not_active Expired
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