US2305675A

US2305675A - Treatment of gasoline

Info

Publication number: US2305675A
Application number: US321574A
Authority: US
Inventors: Joseph A Chenicek
Original assignee: Universal Oil Products Co
Current assignee: Universal Oil Products Co
Priority date: 1940-02-29
Filing date: 1940-02-29
Publication date: 1942-12-22
Anticipated expiration: 1959-12-22

Description

l tie 'ec. 1311.1, 1133 .loseph d. ilheniceh, capo, ML, assimmor to tiniwersal Uill Products lilomp in chicago, Hit, a

corporation or Delae No Drawing.

AMDMIMWHOM Web a a a serial No. 3215M (cl. ii-ii) 23 Dias.

This invention relates to a method for improving the stability of hydrocarbon distillates insofar as color and gum formation are concerned.

More particularly the process concerns improved methods of preventing deterioration of cracked gasolines which may be stored over relatively long periods of time in contact with air.

The use of inhibitors to prevent the depreciation of olefin-containing hydrocarbon distillates such as cracked gasoline has been practiced. Such compounds as alkyl-substituted phenols, aminophenols, fractions of wood tar distillates, etc., have been added to cracked gasoline in relatively minor quantities, of the order of il.0il1-0.l0% to inhibit the formation of objectionable oxidation products and prevent loss of color and antiknock properties of said gasolines during storage periods. The use of inhibitors has replaced or supplemented such forms of refining as acid-treating, clay-treating and the like. The

result has been a material saving in refining costs as well as theconservation of substantial amounts of gasoline which were formerly lost in the refining steps.

The present invention ofiers a means of improving the inhibiting properties of gasoline gum inhibitors and of eiiecting material savings in the quantities of such materials which may be required adequately to preserve the valuable properties ofgasoline.

In one specific embodiment the present invention is a method for treating olefin-containing hydrocarbon distillate and particularly cracked gasoline to preserve the valuable properties thereor which comprises adding to said distillate a gasoline gum inhibitor together with a relatively or quantity of an aryl-substituted-alkylene diamine.

The preferred compounds have the general wherein R is an aryl group, R may be an alkyl cup or a hydrogen atom, R" may be an aryl group or a hydrogen atom, a: may in zero or an integer and m is an integer. Representative compounds are diphenyl ethylene diamine and diorthotolyl ethylene diamlne.

The compounds are used in combination with kno gasoline gum inhibitors such as N-substituted alkyl aminophenols, alkyi phenols, substituted phenol ethers, fractions oi wood tar distillate such as those boiling in the range of Mil-280 0., and others. The compounds of this invention may be added to the gasoline separately or simultaneously with the gum inhibitor, or may be mixed with the'gum inhibitor and the mixture added to the gasoline.

The quantity of aryl-substituted-alkylene diamine used in the gasoline is of the order of 0.000l-0.01%. The exact quantity required is a function of the gum inhibitor with which it is used and of the gasoline as well as the desired stability of the gasoline treated. The compounds of this invention are not of themselves gum inhibitors and the efiect observed is not therefore such as might be expected by the mixing of two gasoline gum inhibitors.

When the present types of compounds are added alone to cracked gasoline in amounts up to approximately 0.1%, little or no increase in the oxygen bomb induction period is to be 'observed and storage tests indicate that no protection is obtained for the gasoline under storage conditions. However, when a gum inhibitor is also added, the induction period with a given quantity of the gum inhibitor is markedly increased and with the more efiective compounds of this invention, frequently more than half of the guminhibltor can be replaced by considerably less than an equal weight per cent of the compounds without suffering a loss in inhibitor potency. This will be brought out more fully in the examples to be given later.

The compounds of this invention are not necessarily exactly equivalent in their effects and it should be understood that they cannot necessarily be used to replace one another in the composite inhibitor with equal efiects either on a weight or chemically equivalent basis.

The following example is given to illustrate the usefulness and practicability of the process, but should not be construed as limiting it to the exact conditions or compounds given therein.

A Pennsylvania cracked gasoline containing 0.01% of N-butyl aminophenol inhibitor had an induction period of 330 minutes by the oxygen bomb test. When 0.01% oi diphenyl ethylene diamine was added thereto, the induction period was increased to 425 minutes. When 0.01% of diorthotolyl ethylene dlamine was added to the inhibited gasoline, the induction period was increased to 385 minutes.

I claim as my invention:

1. A method of treating olefin-containing hydrocarbon distillate to prevent depreciation thereof which comprises adding to said distillate Fl Ii wherein R is an aryl group and a: is an integer.

5. method of treating craclred gasoline to prevent depreciation thereof which comprises adding thereto a gasoline gum inhibitor and a compound of the following general structure:

R a N'om-(cH: ..-N

n 11 wherein R and R are aryl groups and a: is an integer. G. A method of treating cracked gasoline to prevent depreciation thereof which comprises adding thereto a gasoline gum inhibitor and a compound of the following general structure:

a R a I N-(CHz)=-C(CHz)r-N I i1 n wherein R is an aryl group, R is an alkyl group and a: is an integer.

'l. A method of treating cracked gasoline to prevent depreciation thereof which comprises adding thereto a gasoline gum inhibitor and a compound of the following general structure:

. R a" N ora).-o-' on, i-i n l n wherein R andR" are aryl groups R is an alkyl group and an is an integer.

8.,A method of treating cracked gasoline to prevent depreciation thereof which comprises adding thereto a gasoline gum inhibitor and a minor quantity of a diphenyl ethylene diamine.

9. A method of treating cracked gasoline to prevent depreciation thereof which comprises adding thereto a gasoline gum inhibitor and an amount of an aryl-substituted-alkylene diamine within the limits of approximately 0.0001-0.01% by weight of the gasoline treated.

10. A method of treating cracked gasoline to prevent depreciation thereof which comprises adding to said gasoline a gasoline gum inhibitor in amounts of approximately 0.001-0.1% and an amount of an aryl-substituted-alkylene diamine within the limits of approximately 0.0001-0.01%

by weight of the gasoline treated.

11. A method of treating cracked gasoline to prevent depreciation thereof which comprises adding to saidgasoline a gasoline gum inhibitor consisting of an N-substituted alkyl aminophenol and an aryl-substituted-alkylene diamine.

all

arose-rs it. A method of treating cracked gasoline to prevent depreciation thereof which comprises adding to said gasoline a gasoline gum inhibitor consisting of a wood tar fraction boiling within the limits of approximately 240280 C. and an aryl-substituted-alkylene diamine.

it. An inhibitor for cracked gasoline comprising essentially a mixture of a gasoline gum inhibitor and an aryl-substituted-alkylene diamine.

M. an inhibitor for cracked gasoline comprising essentially a mixture of a gasoline gum inhibitor and an aryl-substituted-allrylene dlamine having the following general structure:

1r N-cmom),-N

wherem. ht and it are aryl groups and :c is an integer.

iii. an inhibitor for cracked gasoline comprising essentially a mixture of gasoline gum inhibitor and an aryl-substit-uted-allrylene diamine having the following general structure:

wherein it is an aryl group, R i an alkyl group and is an integer.

1d. inhibitor for cracked gasoline comprising essentially a mixture of a gasoline gum inhibitor and an aryl-suhstituted-alkylene diamine having the following general structure:

n R n" /N-(CHz):(:J-(CH2)=' 11 11 wherein R and R" are aryl groups, R is an alkyl group and r is an integer.

17. An inhibitor for cracked gasoline which comprises essentially e. mmture of a gasolin gum inhibitor and a diphenyl ethylene diamine.

' 18. An inhibitor for cracked gasoline which comprises essentially a mixture of a wood tar dis- 1 tillate boiling within the limits of approximately Edd-280 C. and an aryl-substituted alkylene di- 19. An. inhibitor for cracked gasoline which comprises essentially a mixture of a gum inhibitor with a diorthotolyi ethylene diamine.

20. An inhibitor for cracked gasoline which comprises essentially a mixture of a wood tar distillate gasoline gum inhibitor boiling within the limits of approximately Will-280 C. with a diphenyl ethylene diamine.

21. A composition of matter useful for inhibiting the oxidation of unstable organic substances such as olefin-containing hydrocarbon distillate which comprises a mixture of an antioxidant with an aryl-substituted alkylene diamine.

22. In the art of stabilizing olefinic distillates against deterioration by the addition of gum inhibltors thereto, the method of increasing the gum inhibiting potency of the inhibitor which comprises incorporating into the oleflnic distillate, in addition to the gum inhibitona relatively small amount of an aryl-substituted alkylene diamine.

23. A stabilizing agent suitable for retarding gum formation in olefinic distillates comprising a phenolic gum inhibitor and an amount of an arylsubstituted alkylene diamine such as to increase the inhibiting potency of the phenolic inhibitor.

JOSEPH A. CHENICEK.