US2025192A - Stabilization of mineral hydrocarbon products - Google Patents
Stabilization of mineral hydrocarbon products Download PDFInfo
- Publication number
- US2025192A US2025192A US652775A US65277533A US2025192A US 2025192 A US2025192 A US 2025192A US 652775 A US652775 A US 652775A US 65277533 A US65277533 A US 65277533A US 2025192 A US2025192 A US 2025192A
- Authority
- US
- United States
- Prior art keywords
- gum
- formation
- dihydroxy
- gasoline
- stabilization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000002430 hydrocarbons Chemical class 0.000 title description 11
- 229930195733 hydrocarbon Natural products 0.000 title description 10
- 239000004215 Carbon black (E152) Substances 0.000 title description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 title description 4
- 239000011707 mineral Substances 0.000 title description 4
- 230000006641 stabilisation Effects 0.000 title description 4
- 238000011105 stabilization Methods 0.000 title description 4
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000000446 fuel Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 7
- 238000003860 storage Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 101100491995 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-1 gene Proteins 0.000 description 1
- 101100216944 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-2 gene Proteins 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- -1 dihydroxy naphthalene compound Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
- C10L1/1837—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom hydroxy attached to a condensed aromatic ring system
Definitions
- This invention relates to improvement in means for the stabilization of mineral hydrocarbon products. More particularly it relates to the utilization of organic compounds as addition products for substances of the class named.
- the tendency of liquid hydrocarbons to discolor and to form gum, sludge and resinous substances is at present the bte noire of all persons connected with their production, distribution and use.
- Gasolines, for example, as produced by the modern cracking processes are extremely complicated mixtures comprising many constituents.
- the character of these constituents and the relative proportions of each depend upon the source of the crude petroleum and the particular cracking process employed. Ordinarily substantialpercentages of unsaturated aliphatic and aro- 2 matic hydrocarbons are present. In certain instances these percentages are intentionally increased by the addition of unsaturated compounds to gasolines. Such additions may also be made to gasolines not containing unsaturated hydrocarbons. Regardless of how produced, gasolines containing these unsaturated compounds form, in the presence of air, a series of products some of which are resinous or gummy.
- Example 1 Cracked gasoline treated with 0.02% 1:5-dihydroxy-naphthalene gave 16 mg. gum per 25 cc. in the accelerated oxygen gum test run for five and one-half hours. The gum formed in the same gasoline, but not stabilized, under the same conditions was 120 mg. per 25 cc.
- the concentration of the stabilizing agent may vary between the limits of 0.001 to 1%. It will be apparent, however, that this range is not given as limiting since lesser or greater amounts may be usedin specific instances within the scope of the invention. In most instances no marked advantage is gained by using more than the maximum amount set out above. In any event the range given appears to be suflicient for the grades of gasoline and oils of similar characteristics now on the market.
- the invention is not limited to the specific stabilizing compound set out in the above example.
- the dihydroxy naphthalenes have been found suitable for use in accordance with this invention. Some of these compounds which we have fond to be particularly satisfactory are the following:
- a motor fuel comprising cracked hydrocarbon spirits normally tending to form gum and having a dihydroxy naphthalene incorporated therein in an amount suflicient to inhibit the formation of gum.
- a motor fuel comprising cracked gasoline normally tending to form gum and having a dihydroxy naphthalene incorporated therein in an amount suificient to inhibit the formation of 4.
- a motor fuel comprising cracked gasoline normally-tending to form gum and having 1:5'-dihydroxy naphthalene incorporated therein in an amount suflicient to inhibit the formation of gum.
- the method of inhibiting the formation of 25 gum by an unsaturated gasoline normally tending to form gum which comprises adding to the mineral oil a dihydroxy naphthalene in an amount from 0.001 to 1% to inhibit the formation of gum.
- the method ofinhibiting the formation of gum by motor benzol normally tending to form gum which comprises adding to the motor fuel a dihydroxy naphthalene in an amount sufficient to inhibit the formation of gum.
- the method of inhibiting the formation of gum by a cracked gasoline normally tending to form gum which comprises adding to the gasoline. 1:5-dihydroxy naphthalene in an amount sufficient to inhibit the formation of gum.
- a cracked gasoline normally tending to develop gummy substances upon storage and containing a dihydroxy naphthalene compound in quantity sufliclent to retard such gum formation.
- a cracked gasoline normally tending to de- 4 velop gummy substances upon storage and containing 1:2-dihydroxy-naphthalene in quantity suflicient ,to retard such gum formation.
- a cracked gasoline normally tending to develop gummy substances upon storage and con-- taining 1:4-dihydroxy-naphthalene in quantity sufficient to retard such gum formation.
Description
Patented Dec. 24, 1935 STABILIZATION F MINERAL HYDRO- CARBON PRODUCTS Frederick Baxter Downing, Oarneys Point, N. J.,
and Herbert Warren Walker, Wilmington, Del., assignors to E. I. du Pont de Nemours & Com- P y, ware Wilmington, DeL. a corporation of Dela- No Drawing. Continuation of application Serial No. 484,703, September 26, 1930. This application January 20 1933, Serial No. 652,775
13 Claims.
This invention relates to improvement in means for the stabilization of mineral hydrocarbon products. More particularly it relates to the utilization of organic compounds as addition products for substances of the class named. The tendency of liquid hydrocarbons to discolor and to form gum, sludge and resinous substances is at present the bte noire of all persons connected with their production, distribution and use.
Gasolines, for example, as produced by the modern cracking processes are extremely complicated mixtures comprising many constituents. The character of these constituents and the relative proportions of each depend upon the source of the crude petroleum and the particular cracking process employed. Ordinarily substantialpercentages of unsaturated aliphatic and aro- 2 matic hydrocarbons are present. In certain instances these percentages are intentionally increased by the addition of unsaturated compounds to gasolines. Such additions may also be made to gasolines not containing unsaturated hydrocarbons. Regardless of how produced, gasolines containing these unsaturated compounds form, in the presence of air, a series of products some of which are resinous or gummy. These gums or resins form sticky substances 30 which deposit on the walls and bottom of the container in which the gasolines are stored and in some instances discolor the gasoline. Certain portions of the gums formed may be soluble in the gasoline but they are also objectionable be- 35 cause of the consequent introduction of nonvolatile components into the gasoline. Exposure to sunlight causes discoloration which in some instances is accompanied by appreciable gum- Slmilar problems or disadvantages are encountered with motor benzol which is the name applied to a material similar to gasoline in physical properties but which consists largely of aromatic or unsaturated hydrocarbon compounds.
these disadvantages or to treat the. crude prod- In the past it has been necessary to tolerate use of hydrocarbon motor fuels'which are free from gum and to prevent gum formation in more highly cracked gasolines which would otherwise develop excessive amounts of gum and thereby be rendered unfit for ordinary use. 5 Still further objects are to make it possible to use as an internal combustion fuel liquid hydrocarbons such as gasoline that contain larger amounts of unsaturated compounds than commercially used at present, to produce a. product of this sort at lower cost and to produce one which in certain instances possesses improved anti-knock properties. Other objects will appear hereinafter.
These objects may be accomplished according to the present invention wherein a member or members of the group comprising dihydroxynaphthalenes are added in small quantities to mineral hydrocarbons. The invention will be more readily understood from a consideration of the example which follows in which the parts are given by weight.
One of the tests used for evaluating. the effectiveness of this class of compounds as stabilizers or gum inhibitors is the accelerated oxygen test. In this test twenty-five (25) cc. of motor. fuel, cracked gasoline, motor benzol, or the like, treated with 0.001 to 1% of the stabilizing agent are heated at 100 C. in an atmosphere of oxygen for 3 to 6 hours. The gum formed is measured by evaporating the hydrocarbon after the oxygen testfrom a porcelain. dish in the steam oven. The extent of gum formation during the accelerated oxygen test is a measure of the stability and gumming tendency of the fuel during the long time storage.
Example 1 Cracked gasoline treated with 0.02% 1:5-dihydroxy-naphthalene gave 16 mg. gum per 25 cc. in the accelerated oxygen gum test run for five and one-half hours. The gum formed in the same gasoline, but not stabilized, under the same conditions was 120 mg. per 25 cc. I
It is not desired to limit the invention to the concentration of the stabilizing agent given in the above example. Use may be made of higher or lower concentrations of any member of the group of compounds disclosed above and as a .result thereof greater or less inhibition of gum formation and prevention of discoloration secured depending upon the specific agent used, the solubility of the agent, the. concentration of the agent, the nature of the material treated and the conditions under which the treatment and subsequent storage take place. The preferred actual concentration of the stabilizing agent may vary between the limits of 0.001 to 1%. It will be apparent, however, that this range is not given as limiting since lesser or greater amounts may be usedin specific instances within the scope of the invention. In most instances no marked advantage is gained by using more than the maximum amount set out above. In any event the range given appears to be suflicient for the grades of gasoline and oils of similar characteristics now on the market.
The invention is not limited to the specific stabilizing compound set out in the above example. In general, the dihydroxy naphthalenes have been found suitable for use in accordance with this invention. Some of these compounds which we have fond to be particularly satisfactory are the following:
(i) 1.2-dihydroxy-naphthalene (2) 1.4-dihydroxy-naphthslene (3) l.7-dlhydroxy-naphthalene i OH w (4) 2.3-dihydroxy-naphthalene It is to be understood that other isomers and homologue's in the class mentioned abovemay be used. In certain cases, it has been found advantageous to use two or more of the specific compounds covered by this invention. It will be appreciated that the example outlined above and the specific compounds mentioned are given merely for the purpose of illustrating and not for limiting the invention.
Obviously this invention is of great importance in freeing internal combustion engines from the annoyance and improper functioning due to the deposition-of gum in the fuel containers or fuel systems.
As many apparently widely difierent embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that we do not limit ourselves to the specific embodiments thereof except as defined in the appended claims.
This application is a true continuation of our copending application for "Mineral oil stabilization filed September 26, 1930, Serial No. 484,703. 5
1. A motor fuel comprising cracked hydrocarbon spirits normally tending to form gum and having a dihydroxy naphthalene incorporated therein in an amount suflicient to inhibit the formation of gum.
2. Motor benzol normally tending to form gum and having a dihydroxy naphthalene incorporated therein in an amount suflicient to inhibit the formation of gum.
3. A motor fuel comprising cracked gasoline normally tending to form gum and having a dihydroxy naphthalene incorporated therein in an amount suificient to inhibit the formation of 4. A motor fuel comprising cracked gasoline normally-tending to form gum and having 1:5'-dihydroxy naphthalene incorporated therein in an amount suflicient to inhibit the formation of gum.
5. The method of inhibiting the formation of 25 gum by an unsaturated gasoline normally tending to form gum which comprises adding to the mineral oil a dihydroxy naphthalene in an amount from 0.001 to 1% to inhibit the formation of gum. i 30 6. The method ofinhibiting the formation of gum by motor benzol normally tending to form gum which comprises adding to the motor fuel a dihydroxy naphthalene in an amount sufficient to inhibit the formation of gum. I
7. The method of inhibiting the formation of gum by a cracked gasoline normally tending to form gum which comprises adding to the gasoline. 1:5-dihydroxy naphthalene in an amount sufficient to inhibit the formation of gum.
8. A cracked gasoline normally tending to develop gummy substances upon storage and containing a dihydroxy naphthalene compound in quantity sufliclent to retard such gum formation.
9. A cracked gasoline normally tending to de- 4 velop gummy substances upon storage and containing 1:2-dihydroxy-naphthalene in quantity suflicient ,to retard such gum formation.
10. A cracked gasoline normally tending to develop gummy substances upon storage and con-- taining 1:4-dihydroxy-naphthalene in quantity sufficient to retard such gum formation.
11. Motor benzol normally tending to deteriorate and form gum on. storage and containing 1:2-dihydroxy naphthalene in quantity suflicient
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US652775A US2025192A (en) | 1933-01-20 | 1933-01-20 | Stabilization of mineral hydrocarbon products |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US652775A US2025192A (en) | 1933-01-20 | 1933-01-20 | Stabilization of mineral hydrocarbon products |
Publications (1)
Publication Number | Publication Date |
---|---|
US2025192A true US2025192A (en) | 1935-12-24 |
Family
ID=24618105
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US652775A Expired - Lifetime US2025192A (en) | 1933-01-20 | 1933-01-20 | Stabilization of mineral hydrocarbon products |
Country Status (1)
Country | Link |
---|---|
US (1) | US2025192A (en) |
-
1933
- 1933-01-20 US US652775A patent/US2025192A/en not_active Expired - Lifetime
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