US1074967A - Process of producing beta-methyl-gamma-oxybutyldimethylamin. - Google Patents

Description

GEORG MERLING, OF

LOGINE, GERMANY,

ELBEBFELD,

PROCESS OF PRODUCING AND HUGO KoHLnn, ASSIGNORS 'ro FARBENFABRIKEN VORM. Eamon. BAYER & 00.,

OF ELZBERFELD, GERMANY, A CORPORATION OF GERMANY.

STATES PATEN OFFICE.

OF LEVERKUSEN, NEAR C0- BETA-METHYL-GAMMA-OXYBUTYLDIMETHYLAMIN.

No Drawing.

Specification of Letters Patent. Application filed October 16,

- Patented Oct. 7, 1913.

1912. Serial No. 726,066.

To all whom it may concern:

Be it known that we, Goons Mrmmno and HUGO KoHLER, doctors of philosophy, chemists, citizens of the German Empire, residing, respectively, at Elberfeld and Leverkusen, near Cologne, Germany, have invented new and useful Improvements in Processes of Producing Beta-Methyl Gamma- Oxybutyldimethylamin, of which the following is a specification.

In our applications Serial Nos. 724,635 and 730,017 we have described the production of the new base beta-acetyl-trimethylenetetramethyldiamin, which can be produced by the two-fold introduction of the radical -CI-I,-N(CH,), into acetone, 6. g., by treatment of acetone with a dimethylamino methane com ound such as dimethylaminooxymethane which can be produce by the action of dimethylamin on formaldehyde), either with or without a condensing agent. We have found that this new base the beta-acetyl-trimethylenetetramethyldiamin 4 CH CO CH CHa--N.(CHa)2 cH,-n. cn.

can be easily decomposed by heating it with a dilute acid into dimethylamin and betaacetylallyldimethylamin. This process proceeds according to the following equation:

oH.-co-ou Betwacetyl-trlmethylenetetramethyldiamin.

The latter base can be easily reduced by means of the known reducing agents or electrolytically to the beta-methyl-gamma-oxybutyl-dimethylamin:

om-cnwn-cm-nroma.

This product is identical with the oxy Ease obtainable by the reduction of the keto ase:

oia-co-oH-cm-mcno.

prepared from methylene methyl ethylketone and dimethylamin.

In order to illustrate the new process more fully the following example is given, the parts being by weight :-1 part of acetyltrimethylenetetramethyldiamin under a pressure of"16.5 mm.) 15 boiled. during 1 hour with 4 to 6 parts of sulfuric acid (20 per cent.). Sodium amalam is now gradually added to this solution which has to be cooled and stirred until a test portion no longer reduces potassium permanganate. Durmg the process of reduction' he solution has to be always acid by addition of sulfuric acid. The liquid is so arated then ren or milk of lime and the oxy base is with steam. The base is separated caustic potash.

(boiling point kept from the mercury and is ered alkaline with caustic soda lye distilled cH.N.(cH-). Beta-acetyl-allyldlmethylamln.

finally distilled. Its boiling point 67-69 C. (17 mm).

We claim I 1. Process for producing beta-methylgamma-oxybutyl-dimethylamin, which process consists in first converting beta-acetyltrimethylenetetramethyldiamin int acetyl-allyldimethylamin by treatin a dilute acid and then reducing t e acetylallyldimethylamin thus produced, substantially as described.

2. Process for roducing beta-methylgamma-oxybutyl-dimethylamin, which process consists in first converting beta-acetyltrimethylenetetramethyldiamin into betaacetylallyldimethylamm by treating it with dilute sulfuric acid and then reducing by means. of sodium amalgam the beta-acetylallyl-dimethylamin thus produced, substantially as described;

' 3. The sub-process which comprises converting beta-aoetyl-trimethylenetetramethyldiamin into beta-acetyl-allyl dimethylamm 1 by treating it with a dilute acid.

whereof we have hereunto In testimony the presence of two subset our hands in scribing witnesses.

GEORG MERLING. 1.5. HUGO KOHLER. [L.s.]

Witnesses:

ALBERT UFER,

HERMANN Bnn'rmms.