DE301905C - - Google Patents
Info
- Publication number
- DE301905C DE301905C DENDAT301905D DE301905DA DE301905C DE 301905 C DE301905 C DE 301905C DE NDAT301905 D DENDAT301905 D DE NDAT301905D DE 301905D A DE301905D A DE 301905DA DE 301905 C DE301905 C DE 301905C
- Authority
- DE
- Germany
- Prior art keywords
- hydrate
- bromamylene
- acid
- parts
- trimethylethylene
- 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
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-Methyl-2-butene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 5
- CUILPNURFADTPE-UHFFFAOYSA-N Hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- JGJLWPGRMCADHB-UHFFFAOYSA-N Hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IDEOPBXRUBNYBN-UHFFFAOYSA-N 2-methylbutane-2,3-diol Chemical compound CC(O)C(C)(C)O IDEOPBXRUBNYBN-UHFFFAOYSA-N 0.000 description 1
- JMSRBKPMLUGHCR-UHFFFAOYSA-N Bromohydrin Chemical compound BrC[C]1CO1 JMSRBKPMLUGHCR-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N Hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N Mercury(II) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- -1 hypochlorous acid Chemical compound 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C07C29/66—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens by addition of hypohalogenous acids, which may be formed in situ, to carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
Das Bromamylenhydrat, auch Bromhydrin des Trimethyläthylenglycols genannt, ist schon
längere Zeit bekannt. Es wurde bisher durch Einwirkung von unterbromiger Säure auf Trimethyläthylen
gewonnen, wobei die erforderliche unterbromige Säure durch Einwirken von Brom auf Quecksilberpxyd in Gegenwart von
Wasser dargestellt wurde.
.. Bekannterweise ist aber die unterbromige Säure wie auch die unterchlorige Säure nur
in sehr verdünnter wäßriger Lösung beständig, was zu ihrer Verwendung im gedachten Sinne
große Flüssigkeitsmengen bedingt.The bromamylene hydrate, also called bromohydrin of trimethylethylene glycol, has been known for a long time. It was previously obtained by the action of hypobromous acid on trimethylethylene, the required hypobromous acid being produced by the action of bromine on mercury oxide in the presence of water.
.. As is well known, hypobromous acid, like hypochlorous acid, is only stable in very dilute aqueous solution, which requires large amounts of liquid to be used in the intended sense.
Es wurde nun gefunden, daß dieser der technischen Gewinnung des Bromamylenhydrates im Wege stehende Umstand sich dadurch beseitigen läßt, indem man die unterbromige Säure im Entstehungszustand dadurch zur Reaktion bringt, daß man auf ein durch gute Außenkühlung auf mindestens —5° gebrachtes Gemisch von Trimethyläthylen, Eis und der berechneten Menge Borsäure unter starkem Rühren oder Schütteln die gleichfalls berechnete Menge von unterbromigsaurem Natrium einwirken läßt. Die durch die Borsäure in Freiheit gesetzte unterbromige Säure addiert sich sofort an das Trimethyläthylen und es entsteht das Bromamylenhydrat in guter Ausbeute. It has now been found that this is the technical production of bromamylene hydrate in the way of circumstance can be eliminated by removing the sub-bromine Acid reacts in the state of its formation by responding to a good External cooling brought to at least -5 ° mixture of trimethylethylene, ice and the calculated amount of boric acid with vigorous stirring or shaking is the same calculated Allowed amount of sodium hypobromo to act. The hypobromous acid set free by the boric acid is added immediately to the trimethylethylene and there is the bromamylene hydrate in good yield.
85 Teile Kaliumhydrat werden in etwa 200 Teilen Wasser gelöst und nach Zusatz von ungefähr 200 Teilen Eis in diese Lösung85 parts of potassium hydrate are dissolved in about 200 parts of water and after addition of about 200 parts of ice into this solution
unter Rühren in dünnem Strahle 120 Teile Brom zulaufen gelassen. Diese Lösung von unterbromigsaurem Kali gibt man nun, gleichfalls in dünnem Strahle und unter heftigem Rühren oder Schütteln, in ein Gemisch von 50 Teilen Trimethyläthylen, 20 Teilen kristallisierter Borsäure und 750 Teilen Eis, welche Mischung außerdem- durch eine Eiskochsalzmischung von außen gekühlt wird. Nach beendetem Eintragen erhält man eine gelbliche Lösung, in welcher Eisstückchen schwimmen. Die Flüssigkeit muß nach beendetem Eintragen gegen Jodkaliumstärke noch starke Hypobromitreaktion, zeigen. Nachdem noch etwa 1J2 Stunde weitergerührt wurde, wird der Überschuß am Hypobromit durch Natriumsulfit oder Bisulfit zerstört und die nun farblos gewordene Flüssigkeit mit Benzol ausgeschüttelt. Das Bromamylenhydrat geht in die benzolische Lösung über und wird nach dem Trocknen und Abdestillieren des Benzols im Vacuum übergesiedet. Siedepunkt 45° bei 12 mm.120 parts of bromine allowed to run in with stirring in a thin stream. This solution of potassium bromide is then added, also in a thin stream and with vigorous stirring or shaking, to a mixture of 50 parts of trimethylethylene, 20 parts of crystallized boric acid and 750 parts of ice, which mixture is also cooled from the outside by an ice salt mixture. When the entry is complete, a yellowish solution is obtained in which pieces of ice float. The liquid must still show a strong hypobromite reaction against potassium iodine starch after the end of the introduction. After stirring for a further 1 1/2 hours, the excess hypobromite is destroyed by sodium sulfite or bisulfite and the liquid, which has now become colorless, is shaken out with benzene. The bromamylene hydrate changes into the benzene solution and, after drying and distilling off the benzene, is boiled over in a vacuum. Boiling point 45 ° at 12 mm.
Das Bromamylenhydrat soll zur Darstellung von pharmazeutischen Produkten Verwendung finden.The bromamylene hydrate is said to be used for the preparation of pharmaceutical products Find.
Pate ν τ-Ans ρ ruch:Godfather ν τ-Ans ρ ruch:
Verfahren zur Darstellung von Bromamylenhydrat, darin bestehend, daß man aus unterbromigsauren Salzen und Säure, wie Borsäure, erzeugte unterbromige Säure im Entstehungszustand unter guter Kühlung auf Trimethyläthylen einwirken läßt.Process for the preparation of bromamylene hydrate, consisting in that one hypobromous acid generated from hypobromous salts and acid such as boric acid lets act on trimethylethylene in the state of origin with good cooling.
BERLIN. GEDRUCKT IN DER REICHSDRUCKEREI,BERLIN. PRINTED IN THE REICHSDRUCKEREI,
Claims (8)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE301905C true DE301905C (en) |
Family
ID=555743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT301905D Active DE301905C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE301905C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2463850A (en) * | 1946-07-20 | 1949-03-08 | Standard Oil Dev Co | Process for the production of chlorohydrins |
-
0
- DE DENDAT301905D patent/DE301905C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2463850A (en) * | 1946-07-20 | 1949-03-08 | Standard Oil Dev Co | Process for the production of chlorohydrins |
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