DE175209C - - Google Patents
Info
- Publication number
- DE175209C DE175209C DENDAT175209D DE175209DA DE175209C DE 175209 C DE175209 C DE 175209C DE NDAT175209 D DENDAT175209 D DE NDAT175209D DE 175209D A DE175209D A DE 175209DA DE 175209 C DE175209 C DE 175209C
- Authority
- DE
- Germany
- Prior art keywords
- iodomethyl
- soi
- iodine
- alkali
- chj
- 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.)
- Active
Links
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 6
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 claims description 4
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 3
- 229940008406 diethyl sulfate Drugs 0.000 claims description 3
- -1 iodoethyl Chemical group 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims 1
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 claims 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 230000002378 acidificating Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000698776 Duma Species 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 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
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVs 175209 -KLASSE 12 o. GRUPPE - JVs 175209 - CLASS 12 or GROUP
Dr.WEINLAND und Dr. KARL SCHMID in TÜBINGEN.Dr.WEINLAND and Dr. KARL SCHMID in TÜBINGEN.
Erhitzt man Kaliumchlorid trocken mit Dimethylsulfat, so entsteht nach Dumas (Ann. Chirn. Phys. 58 (1835, 36) Chlormethyl: According to Dumas, if potassium chloride is heated dry with dimethyl sulfate, it is formed (Ann. Chirn. Phys. 58 (1835, 36) chloromethyl:
SOi(CHJ2 SSOi (CHJ 2 p
KCl =KCl =
SOi(CHJ K+ CH3Cl;SOi (CHJ K + CH 3 Cl;
erhitzt man Kaliumbromid trocken mit Dimethylsulfat, so entsteht zwar Brommethyl,If potassium bromide is heated dry with dimethyl sulfate, bromomethyl is produced,
ίο aber nicht ausschließlich, sondern es treten noch andere Reaktionsprodukte in reichlicher Menge auf.ίο but not exclusively, but kick it other reaction products in copious amounts.
Erhitzt man endlich Kaliumiodid trocken mit Dimethylsulfat, so erhält man kein Jodmethyl, sondern es finden andere Reaktionen statt, wobei sich Joddämpfe in großer Menge entwickeln.If one finally heats potassium iodide dry with dimethyl sulfate, no iodomethyl is obtained, but other reactions take place, with iodine vapors developing in large quantities.
Es entstehen ferner bekanntlich Chlor- und Bromalkyle beim Erhitzen von Kaliumchlorid bezw. Kaliumbromid mit konzentrierter Schwefelsäure und dem betreffenden Alkohol, d. h. beim Erhitzen dieser Salze mit den sauren Estern der Schwefelsäure, z. B. Bromäthyl, nach der Formel:It is also known that chlorine and bromine alkyls are formed when potassium chloride is heated respectively Potassium bromide with concentrated sulfuric acid and the alcohol in question, d. H. when heating these salts with the acidic esters of sulfuric acid, e.g. B. bromoethyl, according to the formula:
SOi(C2HJH+ KBr =SOi (C 2 HJH + KBr =
. C2H5Br.. C 2 H 5 Br.
Versucht man wiederum nach dieser Methode Jodalkyle darzustellen, so gelingt dies auf diese Weise keineswegs. ■If one tries again by this method to prepare iodine-alkyls, it succeeds in this way by no means. ■
Man war somit bis jetzt nicht imstande, Jodalkyle mit Hilfe der neutralen oder sauren Ester der Schwefelsäure darzustellen.So up to now it has not been possible to prepare iodine-alkyls with the help of the neutral or acidic To represent esters of sulfuric acid.
Es wurde nun gefunden, daß bei der Einwirkung von Dimethyl- oder Diäthylsulfat auf Alkali- oder Erdalkalijodide in wässeriger Lösung Jodmethyl und Jodäthyl in glatter Reaktion und ganz rein entstehen. Hierbei tritt eine der beiden Alkylgruppen der Alkylsulfate in Reaktion z. B.It has now been found that when exposed to dimethyl or diethyl sulfate on alkali or alkaline earth iodides in aqueous solution iodomethyl and iodoethyl in smooth Reaction and arise completely pure. One of the two alkyl groups of the alkyl sulfates occurs here in response e.g. B.
SOi(CHJ2 + KJ= SO4(CHJK+ CH3J.SOi (CHJ 2 + KJ = SO 4 (CHJK + CH 3 J.
Das Alkyl der alkylschwefelsauren Salze reagiert nicht mit Alkalijodiden.The alkyl of the alkylsulfuric acid salts does not react with alkali iodides.
In eine Lösung von 166 g Kaliumjodid in 166 g Wasser läßt man unter Erwärmen auf dem Wasserbade 126 g Dimethylsulfat bezw. 154 g Diäthylsulfat eintropfen. Jodmethyl bezw. Jodäthyl destillieren sogleich in quantitativer Ausbeute ab.In a solution of 166 g of potassium iodide in 166 g of water, the mixture is made up with warming the water bath 126 g dimethyl sulfate respectively. Drop in 154 g of diethyl sulfate. Iodomethyl respectively Ethyl iodine distill off immediately in quantitative yield.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE175209C true DE175209C (en) |
Family
ID=439883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT175209D Active DE175209C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE175209C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2688641A (en) * | 1950-10-28 | 1954-09-07 | Ethyl Corp | Manufacture of ethyl chloride |
| US2899471A (en) * | 1958-06-18 | 1959-08-11 | Xmethod f for the manufacture of | |
| US3053910A (en) * | 1960-10-07 | 1962-09-11 | Gen Aniline & Film Corp | Method of manufacturing alkyl iodides |
| JP2012201666A (en) * | 2011-03-28 | 2012-10-22 | Central Glass Co Ltd | Method for producing monofluoromethane |
-
0
- DE DENDAT175209D patent/DE175209C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2688641A (en) * | 1950-10-28 | 1954-09-07 | Ethyl Corp | Manufacture of ethyl chloride |
| US2899471A (en) * | 1958-06-18 | 1959-08-11 | Xmethod f for the manufacture of | |
| US3053910A (en) * | 1960-10-07 | 1962-09-11 | Gen Aniline & Film Corp | Method of manufacturing alkyl iodides |
| JP2012201666A (en) * | 2011-03-28 | 2012-10-22 | Central Glass Co Ltd | Method for producing monofluoromethane |
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