US3920415A

US3920415A - Odor inhibition for paraffin hydrocarbons

Info

Publication number: US3920415A
Application number: US433836A
Authority: US
Inventors: Robert E Reusser; Lawrence O Meyer
Original assignee: Phillips Petroleum Co
Current assignee: Phillips Petroleum Co
Priority date: 1974-01-15
Filing date: 1974-01-15
Publication date: 1975-11-18
Anticipated expiration: 1992-11-18

Abstract

Odor formation is inhibited in paraffin hydrocarbons of boiling point range of about 100* to about 700* F by the addition of a small amount of 2,4,6-tris-(dimethyl aminomethyl)phenol.

Description

United States Patent [191 Reusser 'et al. v

11] 3,920,415 [451 Nov. 18, 1975 ODOR INHIBITION FOR PARAFFIN HYDROCARBONS [75] Inventors: Robert E. Reusser; Lawrence 0.

Meyer, both of Bartlesville, Okla.

[73] Assignee: Phillips Petroleum Company,

Bartlesville, Okla.

22 Filed: Jan. 15, 1974 21 Appl. No.: 433,836

[52] US. Cl 44/75; 252/403 [51] Int. Cl. Cl0L 1/22 [58] Field of Search 252/403; 44/75 [56] References Cited UNITED STATES PATENTS 7/1956 Fareri 44/75 Primary Examiner-Delbert E. Gantz Assistant Examinerl. Vaughn [57] ABSTRACT 4 Claims, No Drawings onon INmnrrioNroR PARAFFIN I HYDROYCARBONS I BACKGROUNDOF THE INVENTION This invention relates to paraffin hydrocarbons. In one of its aspects, this invention relates to odor formation in paraffin hydrocarbons. In another of its aspects this invention relates to inhibition of odor formation in paraffin hydrocarbons. In one of its concepts this inl vention relates to the inhibition of an odor formation in ally, an amount in the range of between about 0.005

I and 0.50 weight percent is used. A more preferable amount is in the range of about 0.01 to, about 0.20 weight percent based on the weight of the branched ali phatic hydrocarbons being odor-stabilized. Larger amounts can be used, if desired, but we have not found the use of larger amounts necessary. In fact increased amounts could contribute to the slight fish-like odorparaffin hydrocarbons by the addition of an antioxidant common practice to add an agent effective for inhibiting odor formation to commercial mixtures of these hydrocarbons. We have discovered that 2,4,6-tris- (dimethyl aminomethyl)phenol added in small amounts to paraffin hydrocarbons will inhibit oxidation and consequently the formation of odor bodies.

It is therefore an object of this invention to provide a paraffin hydrocarbon composition stabilized against oxidation that forms odor bodies. It is also an object of this invention to provide a method for stabilizing paraffin hydrocarbons against oxidation that forms odor bodies.

Other aspects, concepts and objects of this invention present when 0.08 weight percent 2,4,6-tris-(dimethyl aminomethyl)phenol is present in Soltrol* 50. *A registered trademark of Phillips Petroleum Company Since the odor-stabilizing 2,4,6-tris-(dimethyl aminomethyl)phenol are soluble in branched aliphatic hydrocarbons in amounts in the range stated above, special means for introducing the 2,4,6-tris-(dimethyl aminomethyl)phenol into the hydrocarbons are unnecessary.

are apparent from the study of the disclosure and the appended claims. 1

SUMMARY OF THE INVENTION According to the invention, oxidation and odor formation in paraffin hydrocarbons are inhibited by the addition of 2,4,6,-tris-(dimethyl aminomethyl)phenol.

In one of the embodiments of this invention an odor inhibited composition of matter comprising at least one paraffin hydrocarbon and 2,4,6-tris-(dimethyl aminomethyl)phenol is provided.

Materials that can be inhibited against odor formation by the process of this invention are paraffin hydrocarbons, or branched aliphatic hydrocarbons, having a boiling point range of from about 100 to about 700 F.

Although individual hydrocarbons boiling within this range can be inhibited by the process of this invention,

the process of this invention will usually be applied to mixtures of hydrocarbons boiling within the given range. Branched aliphatic hydrocarbons having a boiling point within the range of about 240 to about 345 F such as the hydrocarbon mixtures Soltrol* 50 and S01- trol* 100, marketed by Phillips Petroleum Company have been found to be particularly well adapted to this method of odor inhibition.

The 2,4,6-tris-(dimethyl aminomethyl)phenol that has been found suitable as an odor inhibiting agent for branched aliphatic hydrocarbons is available commercially under the name DMP-30 from Rohm and Haas Chemical Co.

It has been found that even a trace of 2,4,6-tris- (dimethyl aminomethyl)phenol is sufficient to stabilize a branched aliphatic hydrocarbon composition. Usu- The cause of odor formation in branched aliphatic hydrocarbons has been determined to be the formation of oxidation products which develop upon storage of the hydrocarbons. The Example below is offered to show the effectiveness of 2,4,6-tris-(dimethyl aminomethyl)phenol in preventing oxidation and, therefore, odor formation in a mixture of branched aliphatic hydrocarbons.

EXAMPLE I Tests were made wherein a sample (A) of Soltrol* 50 (boiling range of 240-300 F) with 0.08 weight percent 2,4,6-tris-(dimethyl aminomethyl)phenol and a sample (B) of Soltrol* 50 alone were placed in separate bombs in an ASTM apparatus for testing oxidation stability of gasoline (ASTM Designation: D525-55). Oxygen was introduced into the bombs until a pressure of psig was attained and then the bombs were placed in hot water baths at 210 F. The pressure reached 120 psig at 210 F. The percent oxygen used in the 3-day period of the tests was calculated from the pressure drop on the bomb at various time intervals.

TABLE I No. of Days of Oxygen Consumed The control (Soltrol* 50 alone)(B) had a strong oxidized hydrocarbon odor (ketone-like odor) while (A) the Soltrol* 50 with 0.08 weight percent 2,4,6-tris- (dimethyl aminomethyl)phenol was water clear, but

had a slight fishlike odor. *A registered trademark of Phillips Petroleum Company EXAMPLE II A 0.05 grams of 2,4,6-tris-(dimethyl aminomethyl)- phenol was added to 100 grams of Soltrol* 50 which had been percolated over 16-30 mesh attapulgite clay (sold by the Milwhite Co., Inc., Houston, Texas) (100 m1 over g attapulgite clay) to remove odor from Soltrol* 50. A part of this mixture was set aside as the inhibited sample for the test report below. Similarly Soltrol* 50 which had been percolated over attapulgite clay was set aside as the control sample. Both the control and the inhibited samples were left outdoors ex- 3 posed to sunlight at atmospheric temperature from December 22 to June 1 in Oklahoma with the temperature varying from about F. to about 100F. The samples were stored in bottles with caps loosely attached for breathing. The samples were inspected periodically for color and odor. The results are reported in Table 11 be- 4 boiling point in the range of about 240F to about 345F and a stabilizing amount of 2,4,6-tris-(dimethyl aminomethy1)phenol.

2. A composition of matter of claim 1 wherein 2,4,6- tris-(dimethyl aminomethyl)phenol is present in an amount in the range of about 0.005 to about 0.50

low. weight percent based on the weight of the branched ali- *A registered trademark of Phillips Petroleum Company h i h d b present Table II No. of Days 0 8 21 83 161 Control clear clear clear water water clear clear Color Inhibited Sample clear sl. sl. water water yellow yellow clear clear Control very very very fair bad good good good Odor lnhibited Sample fishfishfishfishgood like like like like fair It can be seen from the table above that the inhibited sample after developing a slight yellow color during the early part of the test period retained water clearness as did the control as test period progressed. It can also be seen from the table above that the control sample after registering a very good odor for the first 21 days of the test later deteriorated to give a bad odor after 161 days of testing. The inhibited sample while having a fishlike odor had deteriorated after 161 days only to the point of being described as having a good to fair odor.

1 claim:

1. A composition of matter consisting essentially of a mixture of branched paraffin hydrocarbons having a carbons present.

Claims

1. A COMPOSITION OF MATTER CONSISTING ESSENTIALLY OF A MIXTURE OF BRANCHED PARAFFIN HYDROCARBONS HAVING A BOILING POINT IN THE RANGE OF ABOUT 240*F TO ABOUT 345*F AND A STABILIZING AMOUNT OF 2,4,6-TRIS-(DIMETHYL AMINOMETHYL)PHENOL.

2. A composition of matter of claim 1 wherein 2,4,6-tris-(dimethyl aminomethyl)phenol is present in an amount in the range of about 0.005 to about 0.50 weight percent based on the weight of the branched aliphatic hydrocarbons present.

3. A method for inhibiting odor formation in a mixture consisting essentially of branched paraffin hydrocarbons of boiling point range of about 240*F to about 345*F, said method comprising the addition of a stabilizing amount of 2,4,6-tris-(dimethyl aminomethyl)phenol.

4. A method of claim 3 wherein 2,4,6-tris-(dimethyl aminomethyl)phenol is present in an amount in the range of about 0.005 to about 0.50 weight percent based on the weight of the branched aliphatic hydrocarbons present.