US2372588A - Compounded mineral oil - Google Patents
Compounded mineral oil Download PDFInfo
- Publication number
- US2372588A US2372588A US341308A US34130840A US2372588A US 2372588 A US2372588 A US 2372588A US 341308 A US341308 A US 341308A US 34130840 A US34130840 A US 34130840A US 2372588 A US2372588 A US 2372588A
- Authority
- US
- United States
- Prior art keywords
- metal
- compounds
- oils
- pyridine
- radicals
- 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
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- 239000002480 mineral oil Substances 0.000 title description 11
- 235000010446 mineral oil Nutrition 0.000 title description 8
- 150000003254 radicals Chemical class 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 229910052751 metal Inorganic materials 0.000 description 29
- 239000002184 metal Substances 0.000 description 29
- -1 hydrocarbon Chemical class 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000002253 acid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 150000003222 pyridines Chemical class 0.000 description 11
- 239000010802 sludge Substances 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 230000000979 retarding effect Effects 0.000 description 6
- 150000003568 thioethers Chemical class 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 230000009972 noncorrosive effect Effects 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 241000238631 Hexapoda Species 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical class CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- AWIZFKXFPHTRHN-UHFFFAOYSA-N naphtho[2,3-f]quinoline Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 AWIZFKXFPHTRHN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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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
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
-
- 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
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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- 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
- C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
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- 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
- C10N2010/02—Groups 1 or 11
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- 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
- C10N2010/04—Groups 2 or 12
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- 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
- C10N2010/06—Groups 3 or 13
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- 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
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- 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
- C10N2010/10—Groups 5 or 15
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- 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
- C10N2010/12—Groups 6 or 16
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- 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
- C10N2010/14—Group 7
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- 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
- C10N2010/16—Groups 8, 9, or 10
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
Definitions
- This invention relates to compounded minamides.
- a metal and an acid derivaeral oils and more particularly deals with relative of a pyridine or its homolgues or analogues tively high-boiling oils, such as lubricating oils, are combined, while in the amide the metal subelectrical oils, insect spray oils containing oilstitutes one or several hydrogen atoms in an soluble compounds of derivatives of pyridine, its amino radical of an amino pyridine or its homohomologues and analogues. Oils to which this logues or analogues.
- Analogues on the other sticking tendencies of Diesel enginesor aviation 15 hand, are those compounds which contain difengines may be retarded or prevented by the ferent numbers of nitrogen in the nucleus, or addition of such salts to oils with which they whose nuclei contain different numbers of conare lubricated. Moreover, lubricating 0115 may densed aromatic rings, or the same number difbe improved with regard to sludge-forming tendferently arranged.
- chlorpyridine is a encies, viscosity index, pour point, oillness, etc., homologue of pyridine, while qulnoline or pyrimiby the addition of such salts. dine are analogues of pyridine.
- the metal amides of our invention are in genmineral oils having their properties improved in eral good sludge suppressors, many of them actcne r several respects y ing thereto metal ing as anti-oxidants while others function priderivatives of heterocyclic aromatic compounds marily as sludge dispersers. If they contain hycontaining nitrogen in the aromatic nucleus. It drocarbon radicals of relatively high molecular is another purpose to provide anti-ringsticking weights, they may be effective as pour point delubricants.
- Another purpose is to prevent or repressors, viscosity index improvers, anti-corrosion tard sludging of lubricants,electricaloils,etc.,duragents, etc. ing their use. Still another purpose is to provide The salts are useful as sludge dispersers, antia new class of fungicidal and insecticidal spray ringsticking compounds, oxidation retarders, oils. A futher purpose is to provide a class of anti-lacquering agents, pour point depressor-s, oil-soluble addition compounds for mineral oils viscosity index improvers, etc.
- the compounds of our invention may be divided acids of very high molecular weights, may result into two general classes, namely, salts and in oils which, when fresh and unused, are noncorrosive 01 may even be anti-corrosive toward the same bearing metals.
- salts and in oils which, when fresh and unused, are noncorrosive 01 may even be anti-corrosive toward the same bearing metals.
- these originally non-corrosive oils also become corro- SlVe.
- the metal may be bound to the pyridine or its homologues or analogues, through a metal-active amino or acid radical or both. If an amino radical provides the only bond for the metal, then this radical must in its free state possess at least one replaceable hydrogen atom. Thus primary and secondary amino radicals may be suitable. Suitable acid radicals are, for instance, OH, --SH, COOH, CSOH, -SO2OH. These metal-active radicals may be attached directly to the aromatic nuclei or may be linked thereto through a bridge of one or several carbon atoms, which bridge may contain ether, thioether, imino ether, etc., linkages.
- the non-metallic portion contains two or more metal-active radicals, i. e., amino or acid radicals or both.
- metal-active radicals i. e., amino or acid radicals or both.
- a, combination of an amino and an acid radical, or of an OH or SH and a carboxyl radical are particularly desirable, especially if the metal-active radicals happen to be separated from each other by a, bridge of 3 to 4 carbon atoms.
- This bridge may, if desired, contain ether, thioether or imino ether links.
- the metal-active radicals may be attached to the same or to different aromatic nuclei, at least one of which contains a nuclear nitrogen, and which are in close proximity to each other.
- the position of the metal-active radical relative to the nuclear nitrogen atom may also be of some importance. In general, more stable metal compounds are obtained if this radical is separated from the ring nitrogen by two or three carbon atoms.
- the metal compounds In order to exert their beneficial effect, the metal compounds must be soluble in hydrocarbon oils in eflfective quantities, and this may in most 4 instances require the presence of oil-solubilizing groups, such as one or several alkyl, naphthenyl, aryl or arallwl, etc., radicals.
- oil-solubilizing groups such as one or several alkyl, naphthenyl, aryl or arallwl, etc., radicals.
- Such radicals may be introduced into the aromatic nucleus, for example, by reacting suitable chlorinated hydrocarbons, such as chlorinated kerosene, gas oils, lubricating oils, extracts or raflinates thereof, wax, or of pure hydrocarbons, such as butanes, pentanes, hexanes, octanes, dodecanes, cetanes, etc., or corresponding alcohols or oleflnes, with the pyridine compounds, its homologues or analogues, in the presence of a suitable condensing catalyst such as a Friedel-Crafts catalyst, sulfuric acid, phosphoric acid, P205, etc.
- suitable chlorinated hydrocarbons such as chlorinated kerosene, gas oils, lubricating oils, extracts or raflinates thereof, wax, or of pure hydrocarbons, such as butanes, pentanes, hexanes, octanes, dodecanes, cetanes,
- the products of this reaction comprise derivatives of pyridine, or its analogues, wherein at least one hydrogen of the nucleus has been replaced by the hydrocarbon radical.
- the solubilizing radicals may themselves, if desired, contain substitution radicals, such as halogen, hydroxy, ether, hydrosulflde, thioether, amino, imino, etc., radicals. Moreover, they may be connected to the pyridine or homologous nucleus through an ether, thioether or imino ether linkage.
- the pyridine or analogous nucleus may, in addition to the acid 'or amino radical, contain other substitution radicals, such as halogen, nitro, nitroso, nitrile groups.
- the active radical or radicals which links the metal to the pyridine compound or its analogue may be introduced by various known reactions.
- SOaH radicals may be introduced by simple sulfonation. Sulfonated compounds so produced may in turn be treated with alkalis at high temperatures to convert them to the corresponding hydroxy compounds.
- Amino derivatives may be obtained by treating chlorinated pyridine or analogue with ammonia.
- thiopyridines may be produced by treating chlorinated pyridines with KSH.
- Pyridine carboxylic acids may be made by oxidation of alkyl pyridines with KMnO4, etc.
- mixtures of different analogues such as mixtures of quinoline and isoquinoline, or pyridine and quinoline, or alkylated pyridines, quinolines, isoquinolines, etc.
- a suitable source for the production of such mixtures are cracked hydrocarbon oils, such as cracked naphthas, kerosenes, gas oils, etc.
- R represents a hydrocarbon radical which may contain substitution groups
- n and m are integers, the sum of which is not greater than the number of replaceable hydrogens in the pyridine or analogous nuclei
- X is an acidic or amino radical.
- N N R De pending upon the particular type of im- R provement which is to be achieved by the metal A compounds of our invention, different metals may H H 0 be combined with the amino or acid radicals of N N our compounds.
- alkali metals i. e., lithium, sodium, potassium
- alkali earth metals 1. e., 5 H Mg, Ca, Sr, Ba
- earth metals i. e., Al, Ti
- heavy N N metals 1. e., Cu, Ag, Zn, Cd, Hg, Sn, Pb, As, Sb, Bi, Cr, Mo, w, Mn, Fe, Ni, Co, etc.
- lubricating oils we usually prefer the compounds of the poly- O 0 valent light metals, i. e., Mg, Ca, Sr, Ba, Al.
- Com- H H pounds'of metal which are toxic to the lower forms of life, e. g., of Pb, Ag, As, Sb, Tl, etc., and
- salts of relatively strongly basic amines such as quaternary ammonium bases, i. e., tetramethyl, tetramethyl ethyl, dimethyl diethyl, trimethyl benzyl, dlmethyl ethyl benzyl, methyl triisopropyl, triisopropyl benzyl ammonium bases; or piperidine, guanidine. etc.
- quaternary ammonium bases i. e., tetramethyl, tetramethyl ethyl, dimethyl diethyl, trimethyl benzyl, dlmethyl ethyl benzyl, methyl triisopropyl, triisopropyl benzyl ammonium bases; or piperidine, guanidine.
- Very useful are salts of these strong basic amino compounds with sulfonic acids of pyridine, its analogues and homologues.
- composition of claim 1 wherein the amount of the metal derivative is from .1%-10%.-
- a sludge retarding mineral oil composition containing dissolved a small amount of an oilsoluble metal salt of a monocarboxylic acid of a heterocyclic aromatic compound, the aromatic six-membered nucleus of which consists of carbon and nitrogen, at least one nitrogen being trivalent, saidaromatic compound having at least one replaceable nuclear hydrogen substituted by an oil-solubilizing radical.
- composition of claim 3 wherein said solubilizing radical is an aliphatic radical of at least 10 carbon atoms.
- a sludge retarding mineral oil composition containing dissolved a small amount of an oilsoluble metal salt of a monocarboxylic acid of pyridine.
- soluble metal salt of a monocarboxylic acid of an aromatic compound comprising not less than one heterocyclic aromatic six-membered nucleus which consists of carbon and nitrogen, at least one nitrogen being trivalent, said compound containing at least two metal-active radicals separated from each other by a bridge of 3 to 4 carbon atoms.
- a sludge retarding mineral oil composition containing dissolved a small amount of an oilsoluble salt of a monocarboxylic acid of a, heterocyclic aromatic compound, the aromatic sixmembered nucleus of which consists of carbon and nitrogen, at least one nitrogen being trivalent, said metal being linked to the aromatic compound through an active radical, which in its free state contains metal-replaceable hydrogen, said active radical and nuclear nitrogen the formula wherein R is an oil-solubilizing radical, Me is a -metal equivalent of hydrogen and 1
- An improved mineral oil composition containingdissolved an oxidation-inhibiting amount of an oil-soluble metal carboxylate having the formula Rn (300L112
Description
reeeeiea 2?, recs 2 352.5553
aa'zasss comrormnnn MINERAL on.
Robert G. Larsen, Berkeley, and Ernest W. Zublin, San Francisco, Ealift, assignors to Shell Development Company, San Francisco, Calif a corporation of Delaware No Drawing. Application June 19, 1940,
Serial No. 341,308
13 Claims. (Cl. 25239) This invention relates to compounded minamides. In the salt a metal and an acid derivaeral oils, and more particularly deals with relative of a pyridine or its homolgues or analogues tively high-boiling oils, such as lubricating oils, are combined, while in the amide the metal subelectrical oils, insect spray oils containing oilstitutes one or several hydrogen atoms in an soluble compounds of derivatives of pyridine, its amino radical of an amino pyridine or its homohomologues and analogues. Oils to which this logues or analogues.
invention is particularly applicable, though not For the purpose of this invention, we define necessarily limited, are those which, during their homologues of pyridine, quinoline, etc., as those useful lives, are not, or not completely, vaporized derivatives in which one or several replaceable or burned. hydrogen atoms of the aromatic nucleus are sub- It is known that the addition of certain salts stituted with radi cals, such as hydrocarbon, hyof carboxylic acids, sulfonic acids, etc.,to mindrcxy, carboxy, ether, hydrosulfide, sulfide, eral lubricating oils has beneficial effects in amino, imino, halogen, nitro, nitroso, nltrile, sulmany respects. Thus, it is known that the ringionic, etc., radicals. Analogues, on the other sticking tendencies of Diesel enginesor aviation 15 hand, are those compounds which contain difengines may be retarded or prevented by the ferent numbers of nitrogen in the nucleus, or addition of such salts to oils with which they whose nuclei contain different numbers of conare lubricated. Moreover, lubricating 0115 may densed aromatic rings, or the same number difbe improved with regard to sludge-forming tendferently arranged. Thus, chlorpyridine is a encies, viscosity index, pour point, oillness, etc., homologue of pyridine, while qulnoline or pyrimiby the addition of such salts. dine are analogues of pyridine.
It is a purpose of this invention to produce The metal amides of our invention are in genmineral oils having their properties improved in eral good sludge suppressors, many of them actcne r several respects y ing thereto metal ing as anti-oxidants while others function priderivatives of heterocyclic aromatic compounds marily as sludge dispersers. If they contain hycontaining nitrogen in the aromatic nucleus. It drocarbon radicals of relatively high molecular is another purpose to provide anti-ringsticking weights, they may be effective as pour point delubricants. Another purpose is to prevent or repressors, viscosity index improvers, anti-corrosion tard sludging of lubricants,electricaloils,etc.,duragents, etc. ing their use. Still another purpose is to provide The salts are useful as sludge dispersers, antia new class of fungicidal and insecticidal spray ringsticking compounds, oxidation retarders, oils. A futher purpose is to provide a class of anti-lacquering agents, pour point depressor-s, oil-soluble addition compounds for mineral oils viscosity index improvers, etc. All these propwhich are more effective in many respects, and erties will, of course, vary with the configurain some ways have entirely new properties as tion of the organic radicals, the types of substicompared withsimilar compounds heretofore tution radicals and the metal employed, one or suggested. more effects being predominant, while one or more We have discovered that a new class of metal of those enumerated above may be completely compounds wherein a metal is linked through a absent. metal-active radical containing metal and re- Most useful in lubricating oils are in general placeable hydrogen to an aromatic heterocyclic salts, the organic portions of which contain at nucleus consisting of nitrogen and carbon, at least one relatively long carbon chain having least one nuclear nitrogen being trivalent, have 10 or more carbon atoms. These salts are e!- especially useful properties when blended with fective detergents for anti-ringsticking propermineral lubricating O in relatively small q a ties. If their molecular weights are relatively I titles. One of the most outstanding properties high, e. g., above about 800, they also improve of these compounds is their ability to dissolve the V, I.
and finely disperse sludge, which thereby is mm It is known that the addition of various oildered harmless due to its being prevented from soluble metal compounds, such as salts of fatty settling or accumulating on surfaces in need of acids, naphthenic acids, aromatic fatty acids, lubrication. In this property our compounds are alkyl benzoic acids, petroleum sulfonic acids, etc.,
far more eflicient than the corresponding comrender lubricating oils corrosive. Thus the p ds a e on c ccyc rings. Moreover. the presence in lubricating oils of salts which combasic reacti nuclear nitrogen effects a conbine certain metals with certain of the acids siderable reduction in the harmful effect of corcauses'corrosiveness of the freshly blendedoil. rosive free acids which are often formed by which corrosiveness is aggravated as the oil is oxidation during the useful life of many of the used in internal combustion engines. Salts of oils. other metals, particularly when combined with The compounds of our invention may be divided acids of very high molecular weights, may result into two general classes, namely, salts and in oils which, when fresh and unused, are noncorrosive 01 may even be anti-corrosive toward the same bearing metals. However, upon use as crank case oils in internal combustion engines, these originally non-corrosive oils also become corro- SlVe.
The reason for the corrosiveness of the oils containing these salts is not clear, especially when the salts are substantially neutral or basic. Moreover, the rapid increase in the corrosiveness upon use of the oil is difficult to explain.
Whatever the reason for the observed corrosiveness may be, we have discovered that the salts of our acids are considerably less corrosive than the salts of the corresponding acids based on carbocyclic compounds, and if they are corrosive, the corrosiveness of the former is much more completely and more lastingly inhibited than that of the latter by the addition of oxidation inhibitors. I
As previously stated, the metal may be bound to the pyridine or its homologues or analogues, through a metal-active amino or acid radical or both. If an amino radical provides the only bond for the metal, then this radical must in its free state possess at least one replaceable hydrogen atom. Thus primary and secondary amino radicals may be suitable. Suitable acid radicals are, for instance, OH, --SH, COOH, CSOH, -SO2OH. These metal-active radicals may be attached directly to the aromatic nuclei or may be linked thereto through a bridge of one or several carbon atoms, which bridge may contain ether, thioether, imino ether, etc., linkages.
Particularly valuable metal compounds are obtained if the non-metallic portion contains two or more metal-active radicals, i. e., amino or acid radicals or both. Thus a, combination of an amino and an acid radical, or of an OH or SH and a carboxyl radical are particularly desirable, especially if the metal-active radicals happen to be separated from each other by a, bridge of 3 to 4 carbon atoms. This bridge may, if desired, contain ether, thioether or imino ether links. The metal-active radicals may be attached to the same or to different aromatic nuclei, at least one of which contains a nuclear nitrogen, and which are in close proximity to each other.
The position of the metal-active radical relative to the nuclear nitrogen atom may also be of some importance. In general, more stable metal compounds are obtained if this radical is separated from the ring nitrogen by two or three carbon atoms.
In order to exert their beneficial effect, the metal compounds must be soluble in hydrocarbon oils in eflfective quantities, and this may in most 4 instances require the presence of oil-solubilizing groups, such as one or several alkyl, naphthenyl, aryl or arallwl, etc., radicals. Such radicals may be introduced into the aromatic nucleus, for example, by reacting suitable chlorinated hydrocarbons, such as chlorinated kerosene, gas oils, lubricating oils, extracts or raflinates thereof, wax, or of pure hydrocarbons, such as butanes, pentanes, hexanes, octanes, dodecanes, cetanes, etc., or corresponding alcohols or oleflnes, with the pyridine compounds, its homologues or analogues, in the presence of a suitable condensing catalyst such as a Friedel-Crafts catalyst, sulfuric acid, phosphoric acid, P205, etc. The products of this reaction comprise derivatives of pyridine, or its analogues, wherein at least one hydrogen of the nucleus has been replaced by the hydrocarbon radical. The solubilizing radicals may themselves, if desired, contain substitution radicals, such as halogen, hydroxy, ether, hydrosulflde, thioether, amino, imino, etc., radicals. Moreover, they may be connected to the pyridine or homologous nucleus through an ether, thioether or imino ether linkage.
Further, the pyridine or analogous nucleus may, in addition to the acid 'or amino radical, contain other substitution radicals, such as halogen, nitro, nitroso, nitrile groups. 1
The active radical or radicals which links the metal to the pyridine compound or its analogue may be introduced by various known reactions. For example, SOaH radicals may be introduced by simple sulfonation. Sulfonated compounds so produced may in turn be treated with alkalis at high temperatures to convert them to the corresponding hydroxy compounds. Amino derivatives may be obtained by treating chlorinated pyridine or analogue with ammonia. Likewise, thiopyridines may be produced by treating chlorinated pyridines with KSH. Pyridine carboxylic acids may be made by oxidation of alkyl pyridines with KMnO4, etc.
In producing our compounds, we may start out with substantially pure pyridines, quinolines, etc., I
or we may use mixtures of different analogues, such as mixtures of quinoline and isoquinoline, or pyridine and quinoline, or alkylated pyridines, quinolines, isoquinolines, etc. A suitable source for the production of such mixtures are cracked hydrocarbon oils, such as cracked naphthas, kerosenes, gas oils, etc.
In the table below, a, series of formulae of pyridine derivatives and analogues of pyridine are listed which are suitable for producing our oil-soluble salts. In these formulae, R represents a hydrocarbon radical which may contain substitution groups; n and m are integers, the sum of which is not greater than the number of replaceable hydrogens in the pyridine or analogous nuclei; X is an acidic or amino radical.
Pyridines Quinolines and isoquinolines ethers, thioethers, imino ethers, etc., equivalent to those of the pyridines.
Acridines, anthrapyridines, phenanthridines R. I X- Derivatives equivalent to those shown above.
Carboxylic acids N N N N \N coon a. x. R, -x.. Rn Rn 5 V N coon Pyrlduine Pyrlmldine Pyrazin N N x... coon \N N OR a. --x.. R.
. a /N I N Clnnollne Phthslazin R T R I I /N\ coon RF 1? D j on OK 4 4 N /N Qulnazoline Qulnoxaline N C 0 011 N coon Rn X'" NH: W u k NHZ N-N N v N Phenazone Phenazine Rn W /\/N -COOH Below are listed some compounds, the'salts of COOH Rn which are preferred for our purpose: y OH N N N I 0H l coon h R, R R T -coou U l/ n. w
H OH Allwl 3- and 4-hydroxy pyridines N coon N N\ R 40 H B. n I etc.
on OK Suljomc acids N N AlkylB-h droxy Alkyl 3-hydroxy A1kyl 4-hydroxy 4o N Quinn e qulnollne qulnolme t/l I N SH soul so H I N V 3 N SE n. Mixtures of metal derivatives of the above compounds may be used if desired. Furthermore, in
SH addition to our compounds, we may also incor- A l2-thio Alkyli-thio A1k yl8- thio porate in lubricating or other mineral oils con- 1 Home qlmwme qumome ventional anti-oxidants, pour point depressors, corrosion inhibitors, extreme pressure agents, blooming agents, dyes, etc.
N N R De pending upon the particular type of im- R provement which is to be achieved by the metal A compounds of our invention, different metals may H H 0 be combined with the amino or acid radicals of N N our compounds. Thus we may incorporate in the O mineral oils salts of the alkali metals, i. e., lithium, sodium, potassium; alkali earth metals, 1. e., 5 H Mg, Ca, Sr, Ba; earth metals, i. e., Al, Ti; heavy N N metals, 1. e., Cu, Ag, Zn, Cd, Hg, Sn, Pb, As, Sb, Bi, Cr, Mo, w, Mn, Fe, Ni, Co, etc. In lubricating oils we usually prefer the compounds of the poly- O 0 valent light metals, i. e., Mg, Ca, Sr, Ba, Al. Com- H H pounds'of metal which are toxic to the lower forms of life, e. g., of Pb, Ag, As, Sb, Tl, etc., and
particularly Cu, are very valuable in insecticidal and fungicidal oils.
, In many instances, we also may employ salts of relatively strongly basic amines such as quaternary ammonium bases, i. e., tetramethyl, tetramethyl ethyl, dimethyl diethyl, trimethyl benzyl, dlmethyl ethyl benzyl, methyl triisopropyl, triisopropyl benzyl ammonium bases; or piperidine, guanidine. etc. Very useful are salts of these strong basic amino compounds with sulfonic acids of pyridine, its analogues and homologues.
atom being separated from each other by 3 or 3 carbon atoms.
8. A sludge retarding mineral oil composition 7 containing dissolved a small mum of an oil- The amounts of our compounds to be incorpoheterocyclic aromatic compound, the aromatic six-membered nucleus of which consists of carbon and nitrogen, at least one nitrogen being trivalent.
2. The composition of claim 1 wherein the amount of the metal derivative is from .1%-10%.-
3. A sludge retarding mineral oil composition containing dissolved a small amount of an oilsoluble metal salt of a monocarboxylic acid of a heterocyclic aromatic compound, the aromatic six-membered nucleus of which consists of carbon and nitrogen, at least one nitrogen being trivalent, saidaromatic compound having at least one replaceable nuclear hydrogen substituted by an oil-solubilizing radical.
4. The composition of claim 3 wherein said solubilizing radical is an aliphatic radical of at least 10 carbon atoms.
5. A sludge retarding mineral oil composition containing dissolved a small amount of an oilsoluble metal salt of a monocarboxylic acid of pyridine.
soluble metal salt of a monocarboxylic acid of an aromatic compound comprising not less than one heterocyclic aromatic six-membered nucleus which consists of carbon and nitrogen, at least one nitrogen being trivalent, said compound containing at least two metal-active radicals separated from each other by a bridge of 3 to 4 carbon atoms.
9..'1'he composition of claim 8 wherein said bridge contains a linkage selected from the group consisting oi ethers, thioethers and imino ether linkages.
10. A sludge retarding mineral oil composition containing a small amount of an oil-soluble heterocyclic aromatic metal compound having .6. A sludge retarding mineral oil composition containing dissolved a small amount of an oilsoluble metal salt of a monocarboxylic acid of quinoline.
7. A sludge retarding mineral oil composition containing dissolved a small amount of an oilsoluble salt of a monocarboxylic acid of a, heterocyclic aromatic compound, the aromatic sixmembered nucleus of which consists of carbon and nitrogen, at least one nitrogen being trivalent, said metal being linked to the aromatic compound through an active radical, which in its free state contains metal-replaceable hydrogen, said active radical and nuclear nitrogen the formula wherein R is an oil-solubilizing radical, Me is a -metal equivalent of hydrogen and 1|, is an integerwhich is not greater than the number of replaceable hydrogens ot the aromatic nucleus.
11. An improved mineral oil composition containingdissolved an oxidation-inhibiting amount of an oil-soluble metal carboxylate having the formula Rn (300L112
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US341308A US2372588A (en) | 1940-06-19 | 1940-06-19 | Compounded mineral oil |
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US341308A US2372588A (en) | 1940-06-19 | 1940-06-19 | Compounded mineral oil |
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Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
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US2460710A (en) * | 1947-01-31 | 1949-02-01 | American Cyanamid Co | Fungicidal preparations |
US2544904A (en) * | 1946-10-01 | 1951-03-13 | Hoffmann La Roche | Pyridine compounds and method for their production |
US2573662A (en) * | 1948-03-17 | 1951-10-30 | Nepera Chemical Co Inc | Carboxypyridine sulphonic acid compounds |
US2599587A (en) * | 1947-01-18 | 1952-06-10 | Mount Sinai Hospital Res Found | Process of preparing an antibacterial substance from pyridoxamine |
US2620301A (en) * | 1950-12-09 | 1952-12-02 | Standard Oil Co | Grease compositions |
US2649451A (en) * | 1952-05-24 | 1953-08-18 | Bristol Lab Inc | Copper 7-benzyl-8-quinolinate |
US2676926A (en) * | 1950-07-03 | 1954-04-27 | Standard Oil Dev Co | Stabilizer for petroleum products |
US2754183A (en) * | 1954-10-22 | 1956-07-10 | Universal Oil Prod Co | Guanylamino dihydropyrimidines |
US2823182A (en) * | 1950-10-28 | 1958-02-11 | Standard Oil Co | Grease compositions |
US2933379A (en) * | 1958-01-16 | 1960-04-19 | Standard Oil Co | Stabilized motor fuel |
US2986493A (en) * | 1958-02-10 | 1961-05-30 | Philips Corp | Method of combating soil-dwelling nematodes with phenazines |
US3050382A (en) * | 1957-04-16 | 1962-08-21 | Dow Chemical Co | Method of applying an aminopyridine compound to soil and the product thereof to prevent nitrification in soil |
US3088916A (en) * | 1958-08-11 | 1963-05-07 | Monsanto Chemicals | Bacteriostatic and fungistatic cleansing compositions |
US3149076A (en) * | 1962-03-08 | 1964-09-15 | Gulf Research Development Co | Lubricating oil thickened to a grease consistency with a metal salt of orotic acid |
US3149075A (en) * | 1962-03-08 | 1964-09-15 | Gulf Research Development Co | Lubricating oil thickened to a grease consistency with a mixture of a 1, 3, 5-triazine compound and a metal salt of orotic acid |
US3235496A (en) * | 1963-01-02 | 1966-02-15 | Chevron Res | Oxidation resistant grease compositions |
US3285813A (en) * | 1962-07-13 | 1966-11-15 | Union Oil Co | Complex polynuclear carboxylic acid stabilization of halogenated aromatic hydrocarbon insecticides in petroleum hydrocarbon solvent |
US3307970A (en) * | 1961-11-30 | 1967-03-07 | Merck & Co Inc | Preparations for the production of metal 8-hydroxy quinolinates and process for utilizing same |
US3496184A (en) * | 1969-03-18 | 1970-02-17 | Ciba Geigy Corp | Cyclopropylmethoxy-3-quinoline carboxylic acids and esters |
US3723435A (en) * | 1969-07-16 | 1973-03-27 | Ciba Geigy Corp | Metal complexes of mercapto quinoline n-oxides |
USB292054I5 (en) * | 1971-08-23 | 1975-01-28 | ||
US3895013A (en) * | 1971-10-20 | 1975-07-15 | Pechiney Ugine Kuhlmann | Hydroxyquinoline derivative |
US3961054A (en) * | 1973-01-22 | 1976-06-01 | Ciba-Geigy Corporation | Combatting dandruff with mercapto quinoline N-oxides |
-
1940
- 1940-06-19 US US341308A patent/US2372588A/en not_active Expired - Lifetime
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
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US2544904A (en) * | 1946-10-01 | 1951-03-13 | Hoffmann La Roche | Pyridine compounds and method for their production |
US2599587A (en) * | 1947-01-18 | 1952-06-10 | Mount Sinai Hospital Res Found | Process of preparing an antibacterial substance from pyridoxamine |
US2460710A (en) * | 1947-01-31 | 1949-02-01 | American Cyanamid Co | Fungicidal preparations |
US2573662A (en) * | 1948-03-17 | 1951-10-30 | Nepera Chemical Co Inc | Carboxypyridine sulphonic acid compounds |
US2676926A (en) * | 1950-07-03 | 1954-04-27 | Standard Oil Dev Co | Stabilizer for petroleum products |
US2823182A (en) * | 1950-10-28 | 1958-02-11 | Standard Oil Co | Grease compositions |
US2620301A (en) * | 1950-12-09 | 1952-12-02 | Standard Oil Co | Grease compositions |
US2649451A (en) * | 1952-05-24 | 1953-08-18 | Bristol Lab Inc | Copper 7-benzyl-8-quinolinate |
US2754183A (en) * | 1954-10-22 | 1956-07-10 | Universal Oil Prod Co | Guanylamino dihydropyrimidines |
US3050382A (en) * | 1957-04-16 | 1962-08-21 | Dow Chemical Co | Method of applying an aminopyridine compound to soil and the product thereof to prevent nitrification in soil |
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