DE1275043B - Verfahren zur Herstellung von 2-Trichlormethyl-alkylenoxyden - Google Patents
Verfahren zur Herstellung von 2-Trichlormethyl-alkylenoxydenInfo
- Publication number
- DE1275043B DE1275043B DED47591A DED0047591A DE1275043B DE 1275043 B DE1275043 B DE 1275043B DE D47591 A DED47591 A DE D47591A DE D0047591 A DED0047591 A DE D0047591A DE 1275043 B DE1275043 B DE 1275043B
- Authority
- DE
- Germany
- Prior art keywords
- trichloromethyl
- methyl
- reaction
- ether
- chloro
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- PIUOYUWMRQKWGT-UHFFFAOYSA-N 2-methyl-2-(trichloromethyl)oxirane Chemical compound ClC(Cl)(Cl)C1(C)CO1 PIUOYUWMRQKWGT-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000004945 emulsification Methods 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 4
- XIHRDJVCKRDXOG-UHFFFAOYSA-N 1,1,1,3-tetrachloro-2-methylpropan-2-ol Chemical compound ClCC(O)(C)C(Cl)(Cl)Cl XIHRDJVCKRDXOG-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl radical Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- SMZHKGXSEAGRTI-UHFFFAOYSA-N 1,1,1-trichloropropan-2-one Chemical compound CC(=O)C(Cl)(Cl)Cl SMZHKGXSEAGRTI-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED47591A DE1275043B (de) | 1965-06-25 | 1965-06-25 | Verfahren zur Herstellung von 2-Trichlormethyl-alkylenoxyden |
| BE682826D BE682826A (enrdf_load_stackoverflow) | 1965-06-25 | 1966-06-20 | |
| CH904866A CH471776A (de) | 1965-06-25 | 1966-06-22 | Verfahren zur Herstellung von 2-Trichlormethyl-alkylenoxyden |
| NL6608831A NL6608831A (enrdf_load_stackoverflow) | 1965-06-25 | 1966-06-24 | |
| FR66828A FR1484488A (fr) | 1965-06-25 | 1966-06-24 | Procédé de préparation d'oxydes de 2-trichlorométhyl-alcoylène |
| LU51394A LU51394A1 (enrdf_load_stackoverflow) | 1965-06-25 | 1966-06-24 | |
| AT602866A AT268221B (de) | 1965-06-25 | 1966-06-24 | Verfahren zur Herstellung von 2-Trichlormethyl-alkylenoxyden |
| GB2879166A GB1144065A (en) | 1965-06-25 | 1966-06-27 | 2-trichloromethyl alkylene oxides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED47591A DE1275043B (de) | 1965-06-25 | 1965-06-25 | Verfahren zur Herstellung von 2-Trichlormethyl-alkylenoxyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1275043B true DE1275043B (de) | 1968-08-14 |
Family
ID=7050522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED47591A Pending DE1275043B (de) | 1965-06-25 | 1965-06-25 | Verfahren zur Herstellung von 2-Trichlormethyl-alkylenoxyden |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT268221B (enrdf_load_stackoverflow) |
| BE (1) | BE682826A (enrdf_load_stackoverflow) |
| CH (1) | CH471776A (enrdf_load_stackoverflow) |
| DE (1) | DE1275043B (enrdf_load_stackoverflow) |
| GB (1) | GB1144065A (enrdf_load_stackoverflow) |
| LU (1) | LU51394A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6608831A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3615520A1 (de) * | 1986-05-07 | 1987-11-12 | Bayer Ag | Verfahren zur herstellung von 2,3-epoxyamiden |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700686A (en) * | 1951-02-15 | 1955-01-25 | Eastman Kodak Co | Hydroxy substituted polyfluorinated compounds |
-
1965
- 1965-06-25 DE DED47591A patent/DE1275043B/de active Pending
-
1966
- 1966-06-20 BE BE682826D patent/BE682826A/xx unknown
- 1966-06-22 CH CH904866A patent/CH471776A/de not_active IP Right Cessation
- 1966-06-24 NL NL6608831A patent/NL6608831A/xx unknown
- 1966-06-24 AT AT602866A patent/AT268221B/de active
- 1966-06-24 LU LU51394A patent/LU51394A1/xx unknown
- 1966-06-27 GB GB2879166A patent/GB1144065A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700686A (en) * | 1951-02-15 | 1955-01-25 | Eastman Kodak Co | Hydroxy substituted polyfluorinated compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| LU51394A1 (enrdf_load_stackoverflow) | 1966-08-24 |
| CH471776A (de) | 1969-04-30 |
| AT268221B (de) | 1969-02-10 |
| NL6608831A (enrdf_load_stackoverflow) | 1966-12-27 |
| BE682826A (enrdf_load_stackoverflow) | 1966-12-20 |
| GB1144065A (en) | 1969-03-05 |
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