US3905782A - Odor inhibition for paraffin hydrocarbons - Google Patents
Odor inhibition for paraffin hydrocarbons Download PDFInfo
- Publication number
- US3905782A US3905782A US359790A US35979073A US3905782A US 3905782 A US3905782 A US 3905782A US 359790 A US359790 A US 359790A US 35979073 A US35979073 A US 35979073A US 3905782 A US3905782 A US 3905782A
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- United States
- Prior art keywords
- paraffin
- bis
- odor
- ether
- range
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
Definitions
- This invention relates to paraffin hydrocarbons.
- this invention relates to odor'fqrma tion in paraffin hydrocarbon compositions.
- this invention relates to inhibition of odor formation in paraffin hydrocarbon compositions.
- this invention relates to the inhibition of an odor formation in paraffin hy drocarbon com positions by the addition of bis( alkylhydi'o xybenzyl) ether to the paraffin hydrocarbon composition.
- Odorless mineral spirits which are generally marketed for use as paint thinner, insecticide carrier oil, charcoal lighter fluid, industrial cleaning compounds, and solvents are generally composed of a mixture of paraffin hydrocarbons boiling within the range of from about 70F to about 700F. Under shelf storage conditions which include temperatures of up to 125F. or even higher, uninhibited odorless mineral spirits do not tend to remain odorless. It is, therefore, common practice to add an agent effective for inhibiting odor formation to commercial mixtures of these hydrocarbons. We have discovered that certain bis( alkylhydroxybenzyl) ethers added in small amounts to paraffin hydrocarbons will inhibit the formation of odor bodies.
- lt is therefore an object of this invention to provide a paraffin hydrocarbon composition stabilized against odor formation. It is also an object of this invention to provide a method for stabilizing paraffin hydrocarbon compositions against odor formation.
- odor formation in paraffin hydrocarbon compositions is inhibited by the addition of at least one bis(alkylhydroxybenzyl) ether.
- an odor inhibited composition of matter comprising at least one paraffin hydrocarbon and at least one bis(alkylhy droxybenzyl) ether is provided.
- paraffin hydrocarbon compositions having normal boiling points within the range of from about 70F. to about 700F. 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. Paraffin hydrocarbons boiling within the range of from about 240 to about 345F. such as the hydrocarbon mixtures Soltrol* 50 and Soltrol* 100, marketed by Phillips Petroleum Company, have been found to be particularly well adapted to this method of odor inhibition.
- the cause of odor formation in paraffin hydrocarbons has been determined to be the formation of oxidation products which develop upon storage of the hydrocarbons probably because of oxidation of the small amount of unsaturated hydrocarbon impurities which are associated with their production and not completely separable from the paraffin hydrocarbons.
- the example below is offered to show the effectiveness of a bis(alkylhydroxybenzyl) ether in preventing oxidation and, therefore, odor formation in a mixture of paraffin hydrocarbons.
- An odor stabilized composition of matter consisting essentially of a major proportion of at least one paraffin hydrocarbon having a normal boiling point within the range of from about 70F to about 700F, a minor proportion of oxidizable, unsaturated hydrocarbon impurities and an oxidation stabilizing amount of bis(3,5- di-tcrt-butyl-4-hydroxybenzyl) ether.
- a method for inhibiting odor formation in paraffin hydrocarbon compositions consisting essentially of a major proportion of at least one paraffin hydrocarbon having a normal boiling point within the range of from about F to about 700F. and a minor portion of oxidizable, unsaturated hydrocarbon impurities, said method comprising stabilizing the composition with an oxidation inhibiting amount of bis(3,5-di-tert-butyl-4- hydroxybenzyl) ether.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Odor formation is inhibited in paraffin hydrocarbon compositions with normal boiling points within the range of from about 70*F. to about 700*F. by the addition of a small amount of a bis(alkylhydroxybenzyl) ether.
Description
United States Patent [191 Reusser ODOR INHIBITION FOR PARAFFIN HYDROCARBONS [75] Inventor: Robert E. Reusser, Bartiesville,
Okla.
[73] Assignee: Phillips Petroleum Company,
Bartlesville, Okla.
[22] Filed: May 14, 1973 [2!] Appl. No.: 359,790
[52] US. Cl. 44/78; 252/52; 252/404 [5]] Int. Cl Clol 1/18 [58] Field of Search 44/78; 252/52, 404
[56] References Cited UNITED STATES PATENTS [451 Sept. 16, 1975 9/l960 Filbey 44/78 X 2/1968 Longoria 252/404 X Primary Examiner-Delbert E. Gantz Assistant Eraminer-l. Vaughn [57] ABSTRACT 4 Claims, N0 Drawings ODOR INHIBITION FOR PARAFFIN.
HYrDROCARBONS BACKGROUND OF THE INVENTION I This inventionwelates to paraffin hydrocarbons. Inv one of its aspects, this invention relates to odor'fqrma tion in paraffin hydrocarbon compositions. in another of its aspects this invention, relates to inhibition of odor formation in paraffin hydrocarbon compositions. in one of its concepts this invention relates to the inhibition of an odor formation in paraffin hy drocarbon com positions by the addition of bis( alkylhydi'o xybenzyl) ether to the paraffin hydrocarbon composition.
Odorless mineral spirits" which are generally marketed for use as paint thinner, insecticide carrier oil, charcoal lighter fluid, industrial cleaning compounds, and solvents are generally composed of a mixture of paraffin hydrocarbons boiling within the range of from about 70F to about 700F. Under shelf storage conditions which include temperatures of up to 125F. or even higher, uninhibited odorless mineral spirits do not tend to remain odorless. It is, therefore, common practice to add an agent effective for inhibiting odor formation to commercial mixtures of these hydrocarbons. We have discovered that certain bis( alkylhydroxybenzyl) ethers added in small amounts to paraffin hydrocarbons will inhibit the formation of odor bodies.
lt is therefore an object of this invention to provide a paraffin hydrocarbon composition stabilized against odor formation. It is also an object of this invention to provide a method for stabilizing paraffin hydrocarbon compositions against odor formation.
Other aspects, concepts and objects of this invention are apparent from the study of the disclosure and the appended claims.
SUMMARY OF THE INVENTION According to the invention, odor formation in paraffin hydrocarbon compositions is inhibited by the addition of at least one bis(alkylhydroxybenzyl) ether.
In one of the embodiments of this invention an odor inhibited composition of matter comprising at least one paraffin hydrocarbon and at least one bis(alkylhy droxybenzyl) ether is provided.
Materials that can be inhibited against odor formation by the process of this invention are paraffin hydrocarbon compositions having normal boiling points within the range of from about 70F. to about 700F. 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. Paraffin hydrocarbons boiling within the range of from about 240 to about 345F. such as the hydrocarbon mixtures Soltrol* 50 and Soltrol* 100, marketed by Phillips Petroleum Company, have been found to be particularly well adapted to this method of odor inhibition.
*A registered trademark of Phillips Petroleum Company The bis(alkylhydroxybenzyl) ethers that have been found suitable as odor inhibiting agents for paraffin hydrocarbon compositions are those having the structural formula:
'lthas been found that even a trace. of the odor-.
stabilizing bis(alkylhydroxybenzyl) ether compounds described above sufficient to stabilize a paraffin hydrocarbon composition. Usuallypan amount in the! range of between about 0.005 and=0.50 weight percent is used. A more preferable amount is in the range of about 0101 to about 0.20 weight percent based on the weight of the paraffin hydrocarbon composition being odor stabilized. Larger amounts can be Used, if desired, but we'have not found the of-larger antounts neces- Since the odor-stabilizing bis(alkylhydroxybenzyl) ethers are soluble in paraffin hydrocarbons in amounts in the range stated above, special means for introducing the bis(alkylhydroxybenzyl) ether into the hydrocarbons are unnecessary.
The cause of odor formation in paraffin hydrocarbons has been determined to be the formation of oxidation products which develop upon storage of the hydrocarbons probably because of oxidation of the small amount of unsaturated hydrocarbon impurities which are associated with their production and not completely separable from the paraffin hydrocarbons. The example below is offered to show the effectiveness of a bis(alkylhydroxybenzyl) ether in preventing oxidation and, therefore, odor formation in a mixture of paraffin hydrocarbons.
EXAMPLE pressure drop on the bomb at various time intervals. "A registered trademark of Phillips Petroleum Company for branchedchain paraffin hydrocarbons.
TABLE of Oxygen Consumed No. of Days A B The control (Soltrol* 50 alone) (B) had a strong oxidized hydrocarbon odor (ketone-like odor) while (A) the Soltrol* 50 with 0.05 weight percent bis(3,5-ditert-butyl-4-hydroxybenzyl) ether was water clear and odorless.
A registered trademark of Phillips Petroleum Company Reasonable variation and modification are possible within the scope of the foregoing disclosure and the appended claims the essence of which is that the addition of bis(alkylhydroxybenzyl) ether to paraffin hydrocarbons with normal boiling points within the range of from about 701. to about 700F. will prevent the formation of odor bodies in the composition.
I claim:
i. An odor stabilized composition of matter consisting essentially of a major proportion of at least one paraffin hydrocarbon having a normal boiling point within the range of from about 70F to about 700F, a minor proportion of oxidizable, unsaturated hydrocarbon impurities and an oxidation stabilizing amount of bis(3,5- di-tcrt-butyl-4-hydroxybenzyl) ether.
2. A composition of matter of claim I wherein the bis(3,S-di-tert-butyl-4-hydroxybenzyl) ether is present in an amount in the range of about 0.005 to about 0.50 weight percent based on the weight of the paraffin hydrocarbons present.
3. A method for inhibiting odor formation in paraffin hydrocarbon compositions consisting essentially of a major proportion of at least one paraffin hydrocarbon having a normal boiling point within the range of from about F to about 700F. and a minor portion of oxidizable, unsaturated hydrocarbon impurities, said method comprising stabilizing the composition with an oxidation inhibiting amount of bis(3,5-di-tert-butyl-4- hydroxybenzyl) ether.
4. A method of claim 3 wherein the bis(3,5-di-tertbutyl-4-hydroxybenzyl) ether is present in an amount in the range of about 0.005 to about 0.50 weight percent based on the weight of the paraffin hydrocarbons present.
Claims (4)
1. AN ODOR STABILIZED COMPOSITION OF MATTER CONSISTING DROCARBON OF A MAJOR PROPORTION OF AT LEAST ONE PARAFFIN HYDROCARBON HAVING A NORMAL BOILING POINT WITHIN THE RANGE OF FROM ABOUT 70*F TO ABOUT 700*F, A MINOR PROPORTION OF OXIDIZABLE, UNSATURATED HYDROCARBON IMPURITIES AND AN OXIDATION STABILIZING AMOUNT OF BIS(3,5-DI-TERT-BUTYL-4-HYDROXYBENXYL) ETHER.
2. A composition of matter of claim 1 wherein the bis(3,5-di-tert-butyl-4-hydroxybenzyl) ether is present in an amount in the range of about 0.005 to about 0.50 weight percent based on the weight of the paraffin hydrocarbons present.
3. A method for inhibiting odor formation in paraffin hydrocarbon compositions consIsting essentially of a major proportion of at least one paraffin hydrocarbon having a normal boiling point within the range of from about 70*F to about 700*F, and a minor portion of oxidizable, unsaturated hydrocarbon impurities, said method comprising stabilizing the composition with an oxidation inhibiting amount of bis(3,5-di-tert-butyl-4-hydroxybenzyl) ether.
4. A method of claim 3 wherein the bis(3,5-di-tert-butyl-4-hydroxybenzyl) ether is present in an amount in the range of about 0.005 to about 0.50 weight percent based on the weight of the paraffin hydrocarbons present.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US359790A US3905782A (en) | 1973-05-14 | 1973-05-14 | Odor inhibition for paraffin hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US359790A US3905782A (en) | 1973-05-14 | 1973-05-14 | Odor inhibition for paraffin hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3905782A true US3905782A (en) | 1975-09-16 |
Family
ID=23415283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US359790A Expired - Lifetime US3905782A (en) | 1973-05-14 | 1973-05-14 | Odor inhibition for paraffin hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3905782A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997007158A1 (en) * | 1995-08-15 | 1997-02-27 | Hoechst Celanese Corporation | Improved waxes for actuators |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838571A (en) * | 1955-03-21 | 1958-06-10 | Ethyl Corp | 3, 5-dialkyl-4-hydroxybenzyl ethers |
| US2954345A (en) * | 1958-03-31 | 1960-09-27 | Ethyl Corp | Organic materials containing 3, 5-dialkyl-4-hydroxybenzyl ethers as antioxidants |
| US3370093A (en) * | 1962-08-16 | 1968-02-20 | American Potash & Chem Corp | Process for preparing benzyl ethers |
-
1973
- 1973-05-14 US US359790A patent/US3905782A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838571A (en) * | 1955-03-21 | 1958-06-10 | Ethyl Corp | 3, 5-dialkyl-4-hydroxybenzyl ethers |
| US2954345A (en) * | 1958-03-31 | 1960-09-27 | Ethyl Corp | Organic materials containing 3, 5-dialkyl-4-hydroxybenzyl ethers as antioxidants |
| US3370093A (en) * | 1962-08-16 | 1968-02-20 | American Potash & Chem Corp | Process for preparing benzyl ethers |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997007158A1 (en) * | 1995-08-15 | 1997-02-27 | Hoechst Celanese Corporation | Improved waxes for actuators |
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