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US3183188A - Petroleum lubricants stabilized with bactericides - Google Patents

Petroleum lubricants stabilized with bactericides Download PDF

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Publication number
US3183188A
US3183188A US96670A US9667061A US3183188A US 3183188 A US3183188 A US 3183188A US 96670 A US96670 A US 96670A US 9667061 A US9667061 A US 9667061A US 3183188 A US3183188 A US 3183188A
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United States
Prior art keywords
petroleum
nitrohexahydropyrimidine
hydrocarbon
bactericides
bis
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US96670A
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Edward B Hodge
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Commercial Solvents Corp
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Commercial Solvents Corp
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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/04—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • 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
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    • 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
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    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

  • United States Patent ice My invention relates to a stabilized petroleum lubricant and more particularly to a process for the production of stabilized petroleum lubricants containing as the active stabilizing agent nitrohexahydropyrimidines havingthe structural formula:
  • Il -N where R is lower alkyl and where R is selected from the group consisting of lower alkyl and lower hydroxyalkyl.
  • nitrohexahydropyrimidines having the above structural formula are included 1,3-bis(1-hydroxymethylpropyl)--methyl 5 nitrohexahydropyrimidine, 1,3-bis(2-hydroxyethyl) 5 methyl-S-nitrohexahydropyrimidine, 1,3,5-trimethyl 5 nitrohexahydropyrimidine, 5-ethyl-l,3-dimethyl-5-nitrohexahydropyrimidine, S-ethyl- 1,3-bis(2-ethylhexy )-5-nitrohexahydropyrimidine, 1,3-dicyclohexyl 5 ethyl-5-nitrohexahydropyrimidine, S-ethyl-l,3-bis(hydroxy-t-butyl) 5 nitrohexahydropyrimi dine, and S-ethyl-l,3-bis(2-hydroxypentyl)-5-nitrohexa hydropyrimidine.
  • I have found that in some instances
  • each unit was inoculated with 5. mls. of a heterogeneous bacterial culture which had grown: for-several years in a water-cutting oil emulsion. Aeration and mixing were obtained by using an air lift to. continually. circulate the mixture. The tcst was continued for-a period-of six'weeks and .during the six-week period, 5 mls.'0f bacterial. culture were added at periodic weekly'intervals.
  • EXAMPLE IV The following is a core oil which is adequatelyiprotected by 1,000 ppm. of 1,3,S-trimethyl-Smitrohexa- EXAMPLE v The following is a cutting oil which isadequat'elyprotected by 1,000 p.-p.m. of l,3'-bis(l-hydroxymethylpropyl)-5.-methyl-5-nitrohexahydropyrimidine.
  • A' -liquid petroleum composition consisting essentially of a. liquid" petroleum lubricant'hydrocarbon and a suflicient amount of l,3-bis(l-hydroxymethylpropyl) 5 methyl-S-nitrohexahydropyrimidine to stabilize said hydrocarbon against metabolizing bacteria.
  • Aliquid petroleumcomposition consisting essentially of a liquid petroleum lubricant hydrocarbon and a suflicientamount of l,3,5-trimethyl-S-nitroliexahydropyrimidine (to stabilize said hydrocarbon against metabo- 35
  • a liquid petroleum composition consisting essen- I tislly of aliquid petroleum lubricant hydrocnrbon and s sufficient amount of S-ethyl-1,3-dirnethyl-5-nitrohexahydropyrimidine to metabolizing bacteria.
  • a liquid ,petroleumcomposition consisting essentially of .a liquid petroleum lubricant-hydrocarbon and a sufficient. amount of S-ethyl-1,3-bis(hydroxy-t-butyl)-' S-nitrbhexahydropyrimidine to stabilize said hydrocarbon against metabolizing bacteria. p ,5.
  • An aqueous petroleum emulsion consisting essentially'of an aqueous p'etroleumlubricant hydrocarbon emulsion and a suliicient amount of a nitrohexahydropyrimidine to stabilize said hydrocarbon against metabolizinz bacteria, said nitrohexahydropyrimidinehaving the d petroleum composition consisting essen- 6
  • composition of claim said nitrohexahydropyrimidine having the structural formula: :11
  • R-is lower alkylv andtvherein R is selected from the. group consisting of lower hydroxyalkyl and lower r 11.
  • the composition of claim Sywhereinthe composippm. to 2% by weight of tion contains from about 100 the nitrohexahydropyrir'nidine.

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

Description

United States Patent ice My invention relates to a stabilized petroleum lubricant and more particularly to a process for the production of stabilized petroleum lubricants containing as the active stabilizing agent nitrohexahydropyrimidines havingthe structural formula:
Il -N where R is lower alkyl and where R is selected from the group consisting of lower alkyl and lower hydroxyalkyl.
It is well known that organisms from the groups consisting of Corynebacterium, Achromobacter, Pseudomohas, Nocardia and Mycobacterium metabolize petroleum hydrocarbons and fatty acids and thereby produce undesirable oxidation products.
The petroleum industry has long been interested in the stabilization of various petroleum products such as. cutting oils, hydraulic fluids, etc., against breakdown by bacteria which metabolize the hydrocarbons with the concurrent formation of deleterious metabolites.
Many compounds havebeen used as stabilization agents in lubricants, but very few have been found to be commercially successful due to the fact that the compounds are unstable,or are not active against a wide variety of microorganisms.
Among the nitrohexahydropyrimidines having the above structural formula are included 1,3-bis(1-hydroxymethylpropyl)--methyl 5 nitrohexahydropyrimidine, 1,3-bis(2-hydroxyethyl) 5 methyl-S-nitrohexahydropyrimidine, 1,3,5-trimethyl 5 nitrohexahydropyrimidine, 5-ethyl-l,3-dimethyl-5-nitrohexahydropyrimidine, S-ethyl- 1,3-bis(2-ethylhexy )-5-nitrohexahydropyrimidine, 1,3-dicyclohexyl 5 ethyl-5-nitrohexahydropyrimidine, S-ethyl-l,3-bis(hydroxy-t-butyl) 5 nitrohexahydropyrimi dine, and S-ethyl-l,3-bis(2-hydroxypentyl)-5-nitrohexa hydropyrimidine. I have found that in some instances I can obtain total inhibition of bacterial growth in petroleum lubricants at concentrations as low as 100 ppm.
I prefer to include at least 1,000 ppm. in most petroleum' formulations. However, I can'employ amounts up to about 2% by weight of the active nitroamines when the latter is soluble to this extent in the particular petroleum hydrocarbon composition. 1 I'have found that my active ingredients are effective bacteriostatic agents in petroleum containing lubricants such as cutting oils, penetrating oils, grinding lubricants, iron tinning lubricants, core oils, hydraulic fluids, etc.
- The following examples set out lubricating composi- Patented May- 'I I 1965 ting oil concentrate usediwas a-proprietary cutting oilcontions in which my active ingredients act as effective bacteriostatic agents. be limited to the compositions, portions, or lubricants set out below; but rather I intend for all equivalents and variations obvious to those skilled in the art to be included withinthe scope of this specification and the attached It is not intended that my invention taining no bacterial inhibitors. soldi-byjTexaco Incorporated under the name of Soluble Oil Texaco-C. To each of one-gallon containers wasadded lv liter of water-cutting oil emulsion. Desired amounts -.ofmy'nitroa mines were added to the cutting-oil emulsion inthetfirstcontainer.
- No inhibitor was added. to the othercontainer which-was used as a control. At the beginningof' the experiment,
- each unit was inoculated with 5. mls. of a heterogeneous bacterial culture which had grown: for-several years in a water-cutting oil emulsion. Aeration and mixing were obtained by using an air lift to. continually. circulate the mixture. The tcst was continued for-a period-of six'weeks and .during the six-week period, 5 mls.'0f bacterial. culture were added at periodic weekly'intervals.
The following. table sets: out the results of'the above tests and the numberof days ofbacteri al inhibition'when the described concentration or the. desired nitrohexahy- 'dropyrimidines were incorporated into the cutting-oil emulsionj Table I Concentration Number Nitrohexahydropyrimidine in 25: of Days Water-Cutting Eflective Oil Emulsion 1,3-bis(l-hydroxymethylpropyl)-5- methyl-fi-nitrohexahydropyrimidinc- 1, 000 '14 .'';-e th yl-l .3-hi (hydroxy-t-butyl)-5- dropyrimidiue 1,000 42 fyethyl-l.3-1iis(hydroxy-t-hutyl)5- nitrohexahydropyrimidine Y 1,000 42 Control '0 EXAMPLE II The following is a water emulsifiable cutting oil which EXAMPLE III The following is a'stabilized steam cylinder oil which is adequately protected by 1,000 p.p'.m. of '5-ethyl'-1-,3- dimethyl-5-nitrohexahydropyrimidine.
I Percent S.A.E. lubricating oil '90 Oleic acid 10 EXAMPLE IV The following is a core oil which is adequatelyiprotected by 1,000 ppm. of 1,3,S-trimethyl-Smitrohexa- EXAMPLE v The following is a cutting oil which isadequat'elyprotected by 1,000 p.-p.m. of l,3'-bis(l-hydroxymethylpropyl)-5.-methyl-5-nitrohexahydropyrimidine.
Urea 0.4
: slow structural tiormula:
Now bailing described' my, invention; what 1 claim is: 1. A' -liquid petroleum composition consisting essentially of a. liquid" petroleum lubricant'hydrocarbon and a suflicient amount of l,3-bis(l-hydroxymethylpropyl) 5 methyl-S-nitrohexahydropyrimidine to stabilize said hydrocarbon against metabolizing bacteria. I v
2. Aliquid petroleumcomposition consisting essentially of a liquid petroleum lubricant hydrocarbon and a suflicientamount of l,3,5-trimethyl-S-nitroliexahydropyrimidine (to stabilize said hydrocarbon against metabo- 35 A liquid petroleum composition consisting essen- I tislly of aliquid petroleum lubricant hydrocnrbon and s sufficient amount of S-ethyl-1,3-dirnethyl-5-nitrohexahydropyrimidine to metabolizing bacteria. a
stabilize; said hydrocarbon against '4. A liquid ,petroleumcomposition consisting essentially of .a liquid petroleum lubricant-hydrocarbon and a sufficient. amount of S-ethyl-1,3-bis(hydroxy-t-butyl)-' S-nitrbhexahydropyrimidine to stabilize said hydrocarbon against metabolizing bacteria. p ,5. An aqueous petroleum emulsion consisting essentially'of an aqueous p'etroleumlubricant hydrocarbon emulsion and a suliicient amount of a nitrohexahydropyrimidine to stabilize said hydrocarbon against metabolizinz bacteria, said nitrohexahydropyrimidinehaving the d petroleum composition consisting essen- 6| tially -oie liquid petroleum lubricant hydrocarbon and a sufiicient amount of a nitrohexnhydropyrimidine to stabilize said hydrocarbon against metabolizing bacteria,
15 7. The composition of claim said nitrohexahydropyrimidine having the structural formula: :11
f? 10 i NO wherein R-is lower alkylv andtvherein R is selected from the. group consisting of lower hydroxyalkyl and lower r 11. The composition of claim Sywhereinthe composippm. to 2% by weight of tion contains from about 100 the nitrohexahydropyrir'nidine. v
I References Cited by the UNITED STATES PATENTS 12/45 Senkus 260-251 11/57 Pennino 1671-43 11/59 -H0d36 252-515 macros: PATENTS 1 5/39 Australia;
160,367 1155 Australia. 421,189 3/41 Italy.
DANIEL E. WYMAN, mm Eramineri wuus oRssnwALo, Examiner.
of claim 6 itvher'ein the composi of claim- 6 wherein thecornposi- 10. The composition ofelainr o-whenein'the composip.p.m. to 2% by weight of

Claims (1)

  1. 5. AN AQUEOUS PETROLEUM EMULSION CONSISTING ESSENTIALLY OF AN AQUEOUS PETROLEUM LUBRICANT HYDROCARBON EMULSION AND A SUFFICIENT AMOUNT OF A NITROHEXAHYDROPYRIMIDINE TO STABILIZE SAID HYDROCARBON AGAINST METABOLIZING BACTERIA, SAID NITROHEXAHYDROPYRIMIDINE HAVING THE STRUCTURAL FORMULA:
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2391847A (en) * 1944-07-29 1945-12-25 Senkus Murray 5-nitrohexahydropyrimidines and process for preparation thereof
US2812332A (en) * 1955-04-01 1957-11-05 Goodrich Co B F Quaternary ammonium xanthates
US2913414A (en) * 1957-08-01 1959-11-17 Commercial Solvents Corp Petroleum lubricants stabilized against hydrocarbon metabolizable microor-ganisms
US3087891A (en) * 1961-04-10 1963-04-30 Commercial Solvents Corp Process for the control of bacteria in water flooding operations

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2391847A (en) * 1944-07-29 1945-12-25 Senkus Murray 5-nitrohexahydropyrimidines and process for preparation thereof
US2812332A (en) * 1955-04-01 1957-11-05 Goodrich Co B F Quaternary ammonium xanthates
US2913414A (en) * 1957-08-01 1959-11-17 Commercial Solvents Corp Petroleum lubricants stabilized against hydrocarbon metabolizable microor-ganisms
US3087891A (en) * 1961-04-10 1963-04-30 Commercial Solvents Corp Process for the control of bacteria in water flooding operations

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