US2016648A - Stabilizer for gasoline - Google Patents
Stabilizer for gasoline Download PDFInfo
- Publication number
- US2016648A US2016648A US563226A US56322631A US2016648A US 2016648 A US2016648 A US 2016648A US 563226 A US563226 A US 563226A US 56322631 A US56322631 A US 56322631A US 2016648 A US2016648 A US 2016648A
- Authority
- US
- United States
- Prior art keywords
- gasoline
- leuco
- stabilizer
- compounds
- anthraquinone
- 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
- 239000003381 stabilizer Substances 0.000 title description 10
- 150000004056 anthraquinones Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- -1 oxy anthraquinones Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 description 2
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- BUEWYDIBDQYWNO-UHFFFAOYSA-N 7,12-dihydroxynaphtho[2,3-f]quinoline-5,6-dione Chemical compound Oc1c2C(=O)C(=O)c3ncccc3-c2c(O)c2ccccc12 BUEWYDIBDQYWNO-UHFFFAOYSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1857—Aldehydes; Ketones
Definitions
- the present invention relates to stabilizers for gasoline.
- the demand for motor fuels of high anti-knock value has led gasoline manufacturers to crack oil into gasolines while employing comparatively high temperatures which has the effect of increasing the anti-knock value of the product.
- the formation of gum producing substances is also increased, it being noted that such substances are originally present in the gasoline not as gums, but as substances which produce gum in the gasoline upon standing or when used in an internal combustion engine.
- leuco-chinizarian which is 1.4 dihydroxy anthraquinone, to .be highly effective when used in quantities from two ounces to. one pound per tank car of ordinary cracked gasoline (ten'thousand gallons).
- anthrol which is leuco anthraquinone (an example of the class which may be termed non-oxy anthraquinones), leuco purpurin, leuco alizarine blue w. r. and other leuco polyoxy anthraquinones.
- the stabilizers in the gasoline it is desirable that this be done as soon as possible after the gasoline leaves the still, since otherwise the gum forming constituents will have undergone some activity toward gum formation before the stabilizer is added.
- the stabilizer it may be added directly to the gasoline, or, if desired, may be first dissolved in 5 a small quantity of benzol and the solution then added to the gasoline.
- a further advantage of the use of the leuco anthraquinone compounds for the stated purpose is that such compounds are only faintly colored whereby it is possible to use, along with the gas- 15 oline stabilizers mentioned, an anthraquinone color, such for example as is described in the reissue patent to Isermann et al. No. 16,937.
- This combination of the stabilizer and coloring compound is of particular advantage in that the sta- 2O bilizer prevents the gum from forming and thus spoiling the appearance of the dyed gasoline while the coloring material serves to mask the slight color possessed by the cracked gasoline of the character described.
- leuco anthraqui'nones mean those compounds which are related to the corresponding anthraquinones by having a hydrogen atom added to at least one of the ketonic oxygens of the anthraquinones.
- a small quantity of a stabilizer soluble therein consisting of a leuco anthraquinone compound having added hydroxyl radicals at positions other than the 9,10 or quinone carbons.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
Patented Oct. 8, 1935 STABILIZER FOR GASOLINE John Wesley Orelup, Summit, N. J.
No Drawing. Application September 16, 1931, Serial No. 563,226
2 Claims.
The present invention relates to stabilizers for gasoline. The demand for motor fuels of high anti-knock value has led gasoline manufacturers to crack oil into gasolines while employing comparatively high temperatures which has the effect of increasing the anti-knock value of the product. At the same time the formation of gum producing substances is also increased, it being noted that such substances are originally present in the gasoline not as gums, but as substances which produce gum in the gasoline upon standing or when used in an internal combustion engine.
The use of various substances in the nature of negative catalysts has previously been proposed, but to the best of my knowledge these are of limited effectiveness, and moreover, can be used only on gasolines which have been refined in a certain way as, for example, many negative catalysts proposed are quite ineffective upon gasolines refined by a so-called doctor solution (sodium plumbite).
I have now discovered that various members of the anthraquinone series are highly effective as negative catalysts for the purpose specified, such substances falling in the class of leuco anthraquinones. I have further discovered that among the leuco compounds those having added oxygen containing radicals are particularly effective. For example, I have found leuco-chinizarian, which is 1.4 dihydroxy anthraquinone, to .be highly effective when used in quantities from two ounces to. one pound per tank car of ordinary cracked gasoline (ten'thousand gallons).
Other examplesof compounds which I have found to be effective are anthrol, which is leuco anthraquinone (an example of the class which may be termed non-oxy anthraquinones), leuco purpurin, leuco alizarine blue w. r. and other leuco polyoxy anthraquinones.
In incorporating the stabilizers in the gasoline it is desirable that this be done as soon as possible after the gasoline leaves the still, since otherwise the gum forming constituents will have undergone some activity toward gum formation before the stabilizer is added. In incorporating the stabilizer it may be added directly to the gasoline, or, if desired, may be first dissolved in 5 a small quantity of benzol and the solution then added to the gasoline.
In general I have found that the stabilizing power appears partially connected with the power of these compounds to absorb oxygen under 0011- 10 ditions existing in the gasoline.
A further advantage of the use of the leuco anthraquinone compounds for the stated purpose is that such compounds are only faintly colored whereby it is possible to use, along with the gas- 15 oline stabilizers mentioned, an anthraquinone color, such for example as is described in the reissue patent to Isermann et al. No. 16,937. This combination of the stabilizer and coloring compound is of particular advantage in that the sta- 2O bilizer prevents the gum from forming and thus spoiling the appearance of the dyed gasoline while the coloring material serves to mask the slight color possessed by the cracked gasoline of the character described. I
By leuco anthraqui'nones I mean those compounds which are related to the corresponding anthraquinones by having a hydrogen atom added to at least one of the ketonic oxygens of the anthraquinones.
I claim:
1. In combination with a cracked, high compression motor fuel of the gasoline type, a small quantity of a stabilizer soluble therein consisting of a leuco anthraquinone compound having added hydroxyl radicals at positions other than the 9,10 or quinone carbons.
' 2. In combination with a cracked, high compression motor fuel of the gasoline type, a small quantity of a stabilizer soluble therein consisting 40 of leuco-chinizarian. JOHN WESLEY ORELUP.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US563226A US2016648A (en) | 1931-09-16 | 1931-09-16 | Stabilizer for gasoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US563226A US2016648A (en) | 1931-09-16 | 1931-09-16 | Stabilizer for gasoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2016648A true US2016648A (en) | 1935-10-08 |
Family
ID=24249626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US563226A Expired - Lifetime US2016648A (en) | 1931-09-16 | 1931-09-16 | Stabilizer for gasoline |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2016648A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2614987A (en) * | 1950-12-07 | 1952-10-21 | California Research Corp | Grease compositions |
| US2672448A (en) * | 1952-09-27 | 1954-03-16 | California Research Corp | Transformer oil containing a tertiary alkyl phenol antioxidant and a dihydroxy anthraquinone as a synergist for the antioxidant |
| US2672445A (en) * | 1950-04-29 | 1954-03-16 | California Research Corp | Transformer oils |
| US2672447A (en) * | 1949-08-09 | 1954-03-16 | California Research Corp | Oxidation resistant transformer oils and the like |
| US2747978A (en) * | 1952-07-26 | 1956-05-29 | Ethyl Corp | Stabilized organic compositions |
-
1931
- 1931-09-16 US US563226A patent/US2016648A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2672447A (en) * | 1949-08-09 | 1954-03-16 | California Research Corp | Oxidation resistant transformer oils and the like |
| US2672445A (en) * | 1950-04-29 | 1954-03-16 | California Research Corp | Transformer oils |
| US2614987A (en) * | 1950-12-07 | 1952-10-21 | California Research Corp | Grease compositions |
| US2747978A (en) * | 1952-07-26 | 1956-05-29 | Ethyl Corp | Stabilized organic compositions |
| US2672448A (en) * | 1952-09-27 | 1954-03-16 | California Research Corp | Transformer oil containing a tertiary alkyl phenol antioxidant and a dihydroxy anthraquinone as a synergist for the antioxidant |
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