US2293237A - Hydrocarbon product - Google Patents

Hydrocarbon product Download PDF

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Publication number
US2293237A
US2293237A US311523A US31152339A US2293237A US 2293237 A US2293237 A US 2293237A US 311523 A US311523 A US 311523A US 31152339 A US31152339 A US 31152339A US 2293237 A US2293237 A US 2293237A
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US
United States
Prior art keywords
lubricating oil
oil
hydrocarbon product
thiazine
naphtho
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
Application number
US311523A
Inventor
Jeffrey H Bartlett
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Standard Oil Development Co
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Standard Oil Development Co
Priority date (The priority date 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 date listed.)
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Publication date
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to US311523A priority Critical patent/US2293237A/en
Application granted granted Critical
Publication of US2293237A publication Critical patent/US2293237A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/08—Groups 4 or 14

Definitions

  • Patent Aug. 1 1942 BYDBOOARBON PRODUCT deifrey H. ett, Craniord, N. 1., i .L
  • the present invention relates to an improvement in lubricants and ar oils, as well as other hydrocarbon materials, es in respect to resistance to decomposition at elevated temperatures under on conditions such as are encountered in internal combustion es.
  • the invention will be fully unde w from the description which follows.
  • tions ranging from about 0.01% to about 1%, but the quantity generally perierred is about 0.1%.
  • the addition agents of this invention do not have any detrimental eflects on the physical character of the lubricating oil or the mineral oil to which they are added, such as viscosity, gravity and flash point.
  • the present materials may be used as the sole blending agents, or they may be added, in the case of a lubricant, with other ingredients which serve other purposes. They are useful agents to be added to leaded oils, that is to say. lubricants containing lead oleate, lead naphthenate, lead sulionate or other heavy metal soaps. They also may be added along with oiliness agents, pour depressants, lubricating oil dyes, or agents to give fluorescence. They may be used in conjunction with any other antioxidants or with thickeners, sludg or sediment dispersers and the like.
  • the value of the antioxidants of the present invention when used in lubricating oil blends has been determined by a standard oxygen absorption test. This test isused for the most part in judging the omdation susceptibility of a lubricating oil at engine operation temperatures. A known amount of omgen is bubbled through 10 cc. oi the lubricating oil maintained at 200 C.
  • the oxygen is continuously recycled. At the endof successive 15 minute periods, the amount or oxygen absorbed by the oil is measured.
  • the results, usually termed the oxidation rate of the oil, are given as the number of cubic centimeters of oxygen absorbed by 10 cc. oi an oil of the new class of antioxidants in accordance with the present invention.
  • Example 1 ior its ondation rate as above, and the rates for three successive 15 minute intervals were found to be 15, 2d and 31, respectively.
  • An improved lubricant comprising a mineral lubricating oil and a small quantity of a compound of the formula:
  • An'improved lubricant comprising a mineral lubricating oil and a small quantity of 2-methylperi-naphtho-m-thiazine.
  • An improved lubricant comprising a mineral lubricating oiland about 0.1% of 2-methyl-perinaphtho-m-thiazine.
  • An improved lubricant for use at elevated temperatures comprising a lubricating oil and about 0.01% to about 1.0% of a compound of the formula:
  • R, R and R" are selected from the class consisting of hydrogen and halogen atoms and amino, mercapto, hydroxyl and organic groups.
  • An improved lubricant comprising a mineral lubricating oil and a small quantity of Z-(m-hydroxyphenyl) -peri-naphtho-m-thiazine.
  • An improved lubricant comprising a mineral lubricating oil and about 0.2% of Z-(m-hydroxyphenyl) -peri-naphtho-m-thiazine.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Description

Patent Aug. 1 1942 BYDBOOARBON PRODUCT deifrey H. ett, Craniord, N. 1., i .L
Standard Oil Development Company, a corporation oi Delaware No Drawing. sApplieation'December 29, 1939,
e is,
I The present invention relates to an improvement in lubricants and ar oils, as well as other hydrocarbon materials, es in respect to resistance to decomposition at elevated temperatures under on conditions such as are encountered in internal combustion es. The invention will be fully unde w from the description which follows.
It has been found that mineral oil lubricants can be greatly improved in s t to their stability against decomposition, especially under heat and oxidizing conditions, by addition thereto of small amounts of certain substances. In the present case, a new group of substances has discovered which are particularly efiective in re= ducing the oxidation of oils at elevated temperatures This group of substances comprises the peri-naphthothiazines and their derivatives, which may be defined by the formula in which R, R, and R" may be hydrogen, halogen, amino, mercapto, hydroxyl, or an organic group, such as am, aryl, -NH-alkyl, -NH-aryl, -N-alml, -N-aryl, -S-alkyi, -S-aryl, or an organic group containing a heterocyclic ring structure. There may be more than per 15 minute intends ,1; 200 Q one such substituent-group attached to either h following examples illustrate the value or both of the carbon rings.
The following are examples of this class of compounds:
Z-methyl-peri-naphtho-m-thiazine alkow, arony,
as ounce t amend oithe i No. 311,523
tions ranging from about 0.01% to about 1%, but the quantity generally perierred is about 0.1%.
The addition agents of this invention do not have any detrimental eflects on the physical character of the lubricating oil or the mineral oil to which they are added, such as viscosity, gravity and flash point. The present materials may be used as the sole blending agents, or they may be added, in the case of a lubricant, with other ingredients which serve other purposes. They are useful agents to be added to leaded oils, that is to say. lubricants containing lead oleate, lead naphthenate, lead sulionate or other heavy metal soaps. They also may be added along with oiliness agents, pour depressants, lubricating oil dyes, or agents to give fluorescence. They may be used in conjunction with any other antioxidants or with thickeners, sludg or sediment dispersers and the like.
The value of the antioxidants of the present invention when used in lubricating oil blends has been determined by a standard oxygen absorption test. This test isused for the most part in judging the omdation susceptibility of a lubricating oil at engine operation temperatures. A known amount of omgen is bubbled through 10 cc. oi the lubricating oil maintained at 200 C.
The oxygen is continuously recycled. At the endof successive 15 minute periods, the amount or oxygen absorbed by the oil is measured. The results, usually termed the oxidation rate of the oil, are given as the number of cubic centimeters of oxygen absorbed by 10 cc. oi an oil of the new class of antioxidants in accordance with the present invention.
Example 1 ior its ondation rate as above, and the rates for three successive 15 minute intervals were found to be 15, 2d and 31, respectively.
Example 3 oil descrl in pie 1 with approximately 0.2% of 2-(m-hydroxyphenyl) -peri-naphtho-m-thiazine, an orange crystalline compound, which may be prepared according to the method described in Jour. Amer. Chem. Soc., 53:4056 (1931), was tested for its absorption rate in the manner described, and the rates for four successive 15 minute intervals were 14, 14, 18 and 20, respectively.
The present invention is not to be considered as limited by any of the herein described examples, which are given by way of illustration only, but is to be limited solely by the terms of the following claims in which it is desired to claim all novelty inherent in the invention.
I claim:
1. An improved lubricant comprising a mineral lubricating oil and a small quantity of a compound of the formula:
. R in which R, R and R" are selected from the class consisting of hydrogen and halogen atoms and amino, mercapto, hydroxyl and organic groups.
2. An'improved lubricant comprising a mineral lubricating oil and a small quantity of 2-methylperi-naphtho-m-thiazine.
3. An improved lubricant comprising a mineral lubricating oiland about 0.1% of 2-methyl-perinaphtho-m-thiazine.
4. An improved lubricant for use at elevated temperatures comprising a lubricating oil and about 0.01% to about 1.0% of a compound of the formula:
CR M in which R, R and R" are selected from the class consisting of hydrogen and halogen atoms and amino, mercapto, hydroxyl and organic groups.
5. An improved lubricant comprising a mineral lubricating oil and a small quantity of Z-(m-hydroxyphenyl) -peri-naphtho-m-thiazine.
6. An improved lubricant comprising a mineral lubricating oil and about 0.2% of Z-(m-hydroxyphenyl) -peri-naphtho-m-thiazine.
JEFFREY H. BARTLE'IT.
US311523A 1939-12-29 1939-12-29 Hydrocarbon product Expired - Lifetime US2293237A (en)

Priority Applications (1)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2450400A (en) * 1944-01-26 1948-09-28 Gen Aniline & Film Corp Process for producing dye intermediates
US2620303A (en) * 1949-07-09 1952-12-02 California Research Corp Mercaptothiazines as sulfur-corrosion inhibiting agents

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2450400A (en) * 1944-01-26 1948-09-28 Gen Aniline & Film Corp Process for producing dye intermediates
US2620303A (en) * 1949-07-09 1952-12-02 California Research Corp Mercaptothiazines as sulfur-corrosion inhibiting agents

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