GB692755A - Improvements in the production of beta-chlorethyl-ethylene oxide and butadiene monoxide - Google Patents
Improvements in the production of beta-chlorethyl-ethylene oxide and butadiene monoxideInfo
- Publication number
- GB692755A GB692755A GB16796/51A GB1679651A GB692755A GB 692755 A GB692755 A GB 692755A GB 16796/51 A GB16796/51 A GB 16796/51A GB 1679651 A GB1679651 A GB 1679651A GB 692755 A GB692755 A GB 692755A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dichlorbutanol
- chlorethyl
- butadiene monoxide
- ethylene oxide
- beta
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Beta-chlorethyl-ethylene oxide and butadiene monoxide are produced by reacting 1.2.4-butanetriol, its cyclic ether 3-hydroxy-tetrahydrofurane, or its 4-monoalkylethers with hydrogen chloride and treating the resulting 1.4-dichlorbutanol (2) with caustic alkali. To produce b -chlorethyl-ethylene oxide from the 1.4-dichlorbutanol (2) it is preferable to react it with the calculated amount of aqueous caustic alkali at temperatures from about 0 DEG to 50 DEG C. To obtain butadiene monoxide it is necessary to split off a further molecule of HCl and this is done by using solid powdered alkali hydroxide at a temperature in the range 100-150 DEG C., while excluding water. The reaction proceeds as follows <FORM:0692755/IV (b)/1> The two stages may be carried out in one operation by allowing the 1.4-dichlorbutanol (2) to act at a temperature above 100 DEG C. on solid caustic potash, for example. In the examples: (a) 1,2,4-butanetriol is treated with hydrogen chloride to give 1,4-dichlorbutanol-(2) which is treated with potassium hydroxide to give p-chlorethyl ethylene oxide which on further treatment with potassium hydroxide gives butadiene monoxide; (b) a mixture of 3-hydroxytetrahydrofurane and glacial acetic acid is treated with gaseous hydrogen chloride; the 1,4-dichlorbutanol-(2) formed is reacted with potassium hydroxide to give beta-chlorethylethylene oxide and butadiene monoxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE692755X | 1950-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB692755A true GB692755A (en) | 1953-06-10 |
Family
ID=6603499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16796/51A Expired GB692755A (en) | 1950-07-20 | 1951-07-16 | Improvements in the production of beta-chlorethyl-ethylene oxide and butadiene monoxide |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB692755A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2976223A (en) * | 1957-06-04 | 1961-03-21 | Columbia Southern Chem Corp | Recovery of butadiene monoxide by extractive distillation |
-
1951
- 1951-07-16 GB GB16796/51A patent/GB692755A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2976223A (en) * | 1957-06-04 | 1961-03-21 | Columbia Southern Chem Corp | Recovery of butadiene monoxide by extractive distillation |
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