US2160138A

US2160138A - Higher alkyl hydroxyamines

Info

Publication number: US2160138A
Application number: US178559A
Authority: US
Inventors: Peter J Gaylor
Original assignee: Standard Oil Development Co
Current assignee: Standard Oil Development Co
Priority date: 1937-12-07
Filing date: 1937-12-07
Publication date: 1939-05-30
Anticipated expiration: 1956-05-30

Description

Patented May 30, 1939 HIGHER ALKYL HYDROXY- AMINES Peter J. Gaylor, Staten Island, N. Y., assignor to Standard Oil Development Company, a corporation of Delaware No Drawing. Application December '7, 1937, Serial No. 178,559

Claims.

This invention relates to oil blending agents and relates especially to the preparation of improved oil soluble aliphatic hydroxy amines, which materials are excellent as addition agents to lubricants and other oils in order to improve their stability and other properties. The application is a continuation in part of my application No. 746,981, filed October 5, 1934, entitled Oil blending agent.

The invention particularly relates to the process of preparing primary hydroxy amines of high molecular weight which contain the hydroxy and amino group, preferably on adjacent carbon atoms, as exemplified by the following formula:

I on NHz in which R and B may represent any organic radical as, for example, alkyl, aryl, aralkyl, or one of these radicals may represent hydrogen.

The invention is also concerned with the economic preparation of aliphatic hydroxy amino compounds from particular types of feed material, as, for example, from high molecular weight unsaturated aliphatic petroleum compounds from cracked petroleum wax or from paraffin wax, crude scale wax, slack Wax, petrolatum wax, or from solvent extracts of cracked petroleum fractions or similar raw materials. These classes of 30 feed materials give high yields of superior quality products. Especially desirable primary hydroxy amine compounds are those in which thehydroxy and amino group are attached to adjacent carbon atoms, which carbon atoms are at 35 or near the end of the aliphatic chain.

The blending agents of the present application are secured by dehydrogenating or cracking substantially aliphatic materials, preferably aliphatic petroleum materials having from 5 to 30 carbon atoms in the molecule. In this application, the term dehydrogenation will be com strued to include cracking as well as any other methods of producing unsaturation. The preferred initial materials are those olefines hav- 5 ing from '7 to 15 carbon atoms in. the molecule,

preferably cracked paraffin wax oleiines boiling in the range from about 200 to 700 F.

These petroleum ahphatic feed materials may be rendered unsaturated by any suitable method. 50 It is, however, preferred to subject the materials to cracking conditions at temperatures from about 700 to 1100 F. In the case of wax, liquid phase cracking at about 750 F. to 850 F. and atmospheric pressure is preferred. These mate- 5 rials, however, may also be rendered unsaturated by cracking at higher temperatures in the vapor phase, with or without use of elevated pressure (10460 atmospheres) The cracked product in purified by solvent e the crude state, or

xtraction, treating, or other means, is then converted to the corresponding halohydrin by reacting hypochlorous acid, urea with reagents such as halide, or similar reselect a particular treatment. may be separated by The cracked unsaturated suitable boiling range for materials solvent extracting with suitable'solvents as, for example, sulphur dioxide,

phenols, dichlorethyl the like.

ether, alcohol, furfural, and

The preferred process of the present invention is to utilize relatively The preferred process long chain alpha olefines. of preparing these materials which give oil soluble stable products is to crack petroleum Wax peratures in the in the liquid phase at temrange of from 700 to 800 F.,

and preferably at pressures from 0 to pounds gauge. This process yields an unsaturated product rich in long chain alpha olefines.

This entire cracked distillate rich in alpha olefines, or a segregated fraction thereof the range from about 200 to 700 F., with a suitable reagent boiling in is treated to form a halohydrin.

Preferred reagents are hypochlorous acid and urea chloride.

It may be preferable to segregate a particular boiling range of the cracked distillate prior to forming hydrin is then converted to the by any suitable method as, for fluxing with aqueous ammonia a temperature from about 120 the halohydrin. The halohydroxy amine example, by reor by heating at F. to 400 F., with under 3 to 50 or more atmospheres pressure anhydrous ammonia.

This reaction product may be purified and/or concentrated by any of the art as, for example,

of the well-known methods by extraction. with alcohol, distillation, etc.

The invention may be more clearly understood by reference to the following example, which is presented for not to be construed the purpose of illustration and is as limiting the invention in any manner whatsoever.

Example A petroleum paraffin wax containing paraffin hydrocarbons having from 10 to carbon atoms per molecule, averaging about 24 carbon atoms,

Was cracked in the li quid phase at a temperature of about 750 F. under a pressure of about pounds. The cracked distillate was then distilled and the fraction boiling in the range from about 500 F. to 1,000 F. was segregated. This material had an unsaturated content of about 50 to This cracked wax fraction was then treated with urea chloride at approximately room temperature with vigorous stirring. The chlorinated product was then treated with anhydrous ammonia at about F. under pressure. The hydroxy amines were recovered from the reaction mixture through their hydrochlorides and a yield of 10% based on the cracked wax was obtained. These amines showed, upon analysis, 1.69% nitrogen and 0.34% chlorine. 0.2% of these amines in a hydrogenated S. A. E. 50 oil considerably reduced the oxygen absorption rate at about 400 F. It is possible to obtain a chlorine-free product, if desired.

The above invention is not to be limited by any theory or mode of operation but only by the fol lowing claims in which it is desired to claim all novelty in so far as the prior art permits.

I claim:

1. A hydrocarbon oil soluble mixture of higher primary aliphatic hydroxy amines in which the hydroxy group and the amino group of each molecule have been added to the double bond carbon atoms of olefines in a distillate boiling in. the range of 200 to 700" F. prepared by cracking higher boiling paraffinic hydrocarbons of a petroleum source.

2. A product according to claim 1, in which said distillate is rich in alpha olefines having '7 to 15 carbon atoms per molecule and said parafiinic hydrocarbons are in a petroleum Wax.

3. Process for preparing a hydrocarbon oil soluble mixture of primary aliphatic hydroxy amines, which comprises cracking petroleum wax at a temperature in the range of 700 to 1100 F., distilling the resulting cracked products to form a distillate boiling in the range from about 200 to 700 F., converting olefines in said distillate into halohydrins, and reacting said halohydrins with ammonia to form the mixture of aliphatic hydroxy amines.

4. Product secured by the process of claim 3.

5. Process for preparing a hydrocarbon oil soluble mixture of primary aliphatic hydroxy amines, which comprises cracking petroleum wax in the liquid phase at a temperature in the range of about 700 to about 800 R, distilling the resulting cracked products to form a distillate containing alpha olefines having '7 to 15 carbon atoms per molecule, treating said distillate with urea chloride to convert the olefine components of said distillate into chlorhydrins, and reacting the mixed chlorhydrins with ammonia to form the mixture of primary aliphatic hydroxy amines.

PETER J. GAYLOR.