US3150094A - Lubricating oils containing boron monothiophosphate - Google Patents
Lubricating oils containing boron monothiophosphate Download PDFInfo
- Publication number
- US3150094A US3150094A US833406A US83340659A US3150094A US 3150094 A US3150094 A US 3150094A US 833406 A US833406 A US 833406A US 83340659 A US83340659 A US 83340659A US 3150094 A US3150094 A US 3150094A
- Authority
- US
- United States
- Prior art keywords
- monothiophosphate
- boron
- test
- trans
- cis
- 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
- IEMVHDOKTSVJCO-UHFFFAOYSA-K P(=S)([O-])([O-])[O-].[B+3] Chemical compound P(=S)([O-])([O-])[O-].[B+3] IEMVHDOKTSVJCO-UHFFFAOYSA-K 0.000 title description 8
- 239000010687 lubricating oil Substances 0.000 title description 7
- -1 2,2-dimethylbutyl Chemical group 0.000 description 65
- 238000012360 testing method Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 231100000167 toxic agent Toxicity 0.000 description 4
- 239000003440 toxic substance Substances 0.000 description 4
- 239000002199 base oil Substances 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241000239223 Arachnida Species 0.000 description 2
- 241000398201 Bryobia praetiosa Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- NFMSEGPNBWIRTB-UHFFFAOYSA-N decoxy-decylsulfanyl-hydroxy-sulfanylidene-lambda5-phosphane Chemical compound CCCCCCCCCCOP(O)(=S)SCCCCCCCCCC NFMSEGPNBWIRTB-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004338 2,2,3-trimethylbutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004337 3-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- 125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical group CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- GDFCWFBWQUEQIJ-UHFFFAOYSA-N [B].[P] Chemical compound [B].[P] GDFCWFBWQUEQIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- GRADOOOISCPIDG-UHFFFAOYSA-N buta-1,3-diyne Chemical group [C]#CC#C GRADOOOISCPIDG-UHFFFAOYSA-N 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MEVGGUFWHARNOB-UHFFFAOYSA-N didecoxy-hydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCCOP(O)(=S)OCCCCCCCCCC MEVGGUFWHARNOB-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
-
- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
Definitions
- This invention relates to a new composition of matter, to a process for the preparation of the new composition of matter, and to a novel use of said new composition of matter.
- the invention relates to the reaction 'of a dithiophosphate of the formula:
- ⁇ IIELSH R20 with boric acid, i.e., B(OH) to form a boron monothiophosphate of the formula:
- R and R are hydrocarbon radicals from the group consisting of aliphatic radicals of from about 1 to about 30 carbon atoms, cyclo aliphatic radicals of from about 4 to about 30 carbon atoms, and aromatic radicals of from about 6 to about 14 carbon atoms.
- the aromatic radicals can be mono nuclear or poly nuclear and can contain hydrocarbon substituents.
- R and R can be the same or can constitute different hydrocarbon radicals.
- aliphatic radicals are: methyl; ethyl; propyl; n-butyl; isobutyl; n-pentyl; isopentyl; neopentyl; n-hexyl; Z-methylpentyl; 3-methylpentyl; 2,2-dimethylbutyl; 2,3-dimethylbutyl; n-heptyl; Z-methylhexyl; 3-methylhexyl; 3-ethylpentyl; 2,2-dimethylpentyl; 2,3-dimethylpentyl; 2,4-dimethylpentyl; 3,3-dimethylpentyl; 2,2,3-trimethylbutyl; n-octyl; Z-methylheptyl; 3-methylheptyl; 2,2- dimethylhexyl; 2,3-dimethylhexyl; 2,5-dimethylhexyl; 3,4- dimethylhexyl; 2,2,3
- cyclo aliphatic radicals are: cyclupropyl; cyclobutyl; methylcyclopropyl; cyclopentyl; cyclohexyl; methylcyclopentyl; methylcyclohexyl; ethylcyclopentyl; 1,1-dimethylcyclopenty1; cis and trans 1,2-dimethylcyclopentyl; cis and trans 1,3-dimethylcyclopentyl; cyclooctyl; ethylcyclohexyl; cis and trans 1,3-dimethylcyclohexyl; pmenthyl; cyclobutenyl; cyclopentenyl; cyclohexenyl; cyclooctenyl; 3-p-menthenyl; cyclopentadienyl; di-limonenyl; a-terpinenyl; ,B-phellandrenyl; cyclooc
- an object of the present invention to provide a new composition of matter. It is a further object of this invention to provide a process for the manufacture of the new composition of matter. It is another object of this invention to provide an improved motor fuel. It is another object of this invention to provide an improved lubricating oil. It is a further object of this invention to provide a new pesticide. It is a further object of this invention to provide a motor fuel having inhibited surface ignition properties. It is a further object of this invention to provide a lubricating oil having inhibited silver, copper, and lead corrosion properties. It is a still further object of this invention to provide a lubricating oil having inhibited oxidation properties.
- EXAMPLE I Boron Di-n-Decyl Monothiophosphate The new composition was prepared by placing 785 g. of di-n-decyl dithiophosphate in a flask fitted with a stirrer, a thermometer, and a nitrogen purge tube. The next step included the addition of 39.6 g. of powdered boric acid to the flask which contained the dithiophosphate. The mixture of the di-n-decyl dithiophosphate and boric acid was heated to a temperature between 210 and 250 F. for one hour while utilizing nitrogen to purge the atmosphere within the flask. The reaction product resembled a pale yellow oil. Results of an analysis of the boron di-n-decyl monothiophosphate are as follows:
- the new boron monothiophosphates are, for the most ,part, oily liquids somewhat soluble in many organic solvents. They are particularly soluble in hydrocarbons.
- the boron monothiophosphates when combined with a carrier, such as a spray or such as a dust composition, exert a definite toxicity against arachnids such as, for example, Tetranychus bimaculatus (two-spotted spider mite), Paratetranychus pilosus (European red mite), Bryobia praetiosa (clover mite) as well as certain small homopterous insects such as, for example, aphids.
- This pesticide gives excellent control of such organisms for extended periods of time.
- the new toxicant may be used as a spray or as a dust compound. It may be employed in combination with an inert material carrier such as a finely divided solid, or a solvent liquid.
- the toxicant may be present in the inert carrier material in relatively high concentrations to provide a concentrate adapted for further dilution. It may also be present in the inert carrier material in dilute form to provide compositions suitable for application without further modification.
- EXAMPLE A A standard agricultural screening method was used to test the arachnids. The test included both the nympth and adult stage. A contact spray method was used within a Feet-Grady chamber. The chamber was operated at 5 p.s.i.g. One hundred organisms were placed on the bean plants. A concentration of 0.025% toxicant in acetone was sprayed on the bean plant. A count was made after 24 hours.
- a standard agricultural screening method was used to test the aphididae family. The test included both the nympth and adult stage.
- a contact spray method was used within a Peet-Grady chamber. The chamber was operated at 5 p.s.i.g. One hundred organisms were placed on cotton plants. A concentration of 0.1% toxicant in acetone was sprayed on the cotton plant. A count was made after 24 hours.
- a standard CFR L-head engine test utilizes an engine with a compression ratio of 7.0 to 1, a water temperature of 148 F. (:3 R), an oil temperature of 160 F. (i3 F.), and an air intake temperature of 110 F. (:5 F.).
- the test cycle is as follows:
- a di-alkyl monothiophosphate was prepared by the reaction of P 5 with a mixture of 70 mole percent isopropyl alcohol and 30 mole percent oxodecyl alcohol and subsequent reaction with boric acid as set forth in Example II.
- This material was tested in a standard Timken testing machine. Such test is well known to those skilled in the art as being useful in obtaining valuable information with respect to the potential commercial value of extreme pressure lubricants. The Timken machine and test are fully described in the Journal of the Institute of Petro leum, 32, pages 209-210 and 220-222 (1946).
- Timken load value resulting from the addition of a very small amount of boron monothiophosphate to a conventional petroleum lubricating oil.
- Base oil 700 1. 000 Base oil 1% additive 55.1 71. 2
- R and R are each the hydrocarbyl residue of an alcohol of a mixture of alcohols consisting of about 70 mole percent isopropyl alcohol and about mole percent decyl alcohol.
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Description
United States Patent 3,150,094 LUBRICATING OILS (IONTAINING BORON MONOTHIOPHOSPHATE Edwin L. De Young, Chicago, Ill., and Albert R. Sabol, Munster, Ind., assignors to Standard Oil Company, Chicago, 111., a corporation of Indiana No Drawing. Filed Aug. 13, 1959, Ser. No. 833,406 1 Claim. (Cl. 252-46.7)
This invention relates to a new composition of matter, to a process for the preparation of the new composition of matter, and to a novel use of said new composition of matter.
Briefly described, the invention relates to the reaction 'of a dithiophosphate of the formula:
\IIELSH R20 with boric acid, i.e., B(OH) to form a boron monothiophosphate of the formula:
R and R are hydrocarbon radicals from the group consisting of aliphatic radicals of from about 1 to about 30 carbon atoms, cyclo aliphatic radicals of from about 4 to about 30 carbon atoms, and aromatic radicals of from about 6 to about 14 carbon atoms. The aromatic radicals can be mono nuclear or poly nuclear and can contain hydrocarbon substituents. R and R can be the same or can constitute different hydrocarbon radicals.
Examples of such aliphatic radicals are: methyl; ethyl; propyl; n-butyl; isobutyl; n-pentyl; isopentyl; neopentyl; n-hexyl; Z-methylpentyl; 3-methylpentyl; 2,2-dimethylbutyl; 2,3-dimethylbutyl; n-heptyl; Z-methylhexyl; 3-methylhexyl; 3-ethylpentyl; 2,2-dimethylpentyl; 2,3-dimethylpentyl; 2,4-dimethylpentyl; 3,3-dimethylpentyl; 2,2,3-trimethylbutyl; n-octyl; Z-methylheptyl; 3-methylheptyl; 2,2- dimethylhexyl; 2,3-dimethylhexyl; 2,5-dimethylhexyl; 3,4- dimethylhexyl; 2,2,3-trimethylpentyl; 2,2,4-trimethylpentyl; 2,3,3-trimethylpentyl; 2,3,4-trimethylpentyl; n-nonyl; n-decyl; n-undecyl; n-hexadecyl; n-octadecyl; n-eicosyl; n-triacontyi; ethenyl; propenyl; l-butenyl; Z-butenyl; cis and trans methylpropenyl; l-pentenyl; Z-pentenyl; cis and trans Z-methyl-Z-butenyl; l-hexenyl; 3-hexenyl (trans-); 3 methyl l-pentenyl; Z-methyl-Z-pentenyl; 3-methyl-2- pentenyl; cis and trans 2,3-dirnethyl-2-butenyl; 3,3-dimethyl-l-butenyl; 2,4,4-trimethyl-l-pentenyl; 2,3,4-trimethyl- 2-pentenyl; 2,4,4-trimethy1-2-pentenyl; cis and trans 3,4,4- trimethyl-Z-pentenyl; l-hexadecenyl; l-hexacosenyl; l-triacontenyl; allyl; 1,3-butadienyl; 1,3-pentadienyl; cis and trans isoprenyl; 1,5-hexadienyl; cis and trans 2,4-hexadienyl; cis and trans Z-methyl-l; 3-pentadienyl; 4-methyl- 1,3-pentadienyl; 1,3,5-hexatrienyl; ethynyl; propynyl; 1- butynyl; Z-butynyl; butenynyl; 1,5-hexadien-3-ynyl; 1,5,7- octatrien-S-ynyl; butadiynyl; 1,5-hexadiynyl; 2,4-hexadiynyl.
Examples of such cyclo aliphatic radicals are: cyclupropyl; cyclobutyl; methylcyclopropyl; cyclopentyl; cyclohexyl; methylcyclopentyl; methylcyclohexyl; ethylcyclopentyl; 1,1-dimethylcyclopenty1; cis and trans 1,2-dimethylcyclopentyl; cis and trans 1,3-dimethylcyclopentyl; cyclooctyl; ethylcyclohexyl; cis and trans 1,3-dimethylcyclohexyl; pmenthyl; cyclobutenyl; cyclopentenyl; cyclohexenyl; cyclooctenyl; 3-p-menthenyl; cyclopentadienyl; di-limonenyl; a-terpinenyl; ,B-phellandrenyl; cyclooctatetraenyl; p-caro- 3,150,094 Patented Sept. 22, 1964 ice tenyl; thujanyl; caranyl; pinanyl; camphanyl; cis and trans decahydronaphthyl; a-thujenyl; A -carenyl; t-pinenyl; bornylenyl; camphenyl; tricyclenyl; adamantanyl; dicyclopentadienyl.
Examples of such aromatic radicals are: phenyl; tolyl; o-xylyl; m-xylyl; p-xylyl; ethylphenyl; n-propylphenyl; rpropylphenyl; 1,2,3-trimethylpheny1; 1,2,4-trimethylphenyl; mesitylyl; p-cymyl; 1,3-diethylphenyl; 1,4-diethylphenyl; 1,2,3,4-tetramethylphenyl; 1,2,3,S-tetrarnethylphenyl; 1,2,4,5-tetramethylphenyl; hexamethylphenyl; n-dodecylphenyl; styryl; allylphenyl; l-phenyl=1,3-butadienyl; phenylethynyl; biphenyl; o-terphenyl; m-terphenyl; p-terphenyl; p-quaterphenyl; 1,3,5-triphenyl-phenyl; diphenylmethyl; 1,1-diphenylethyl; bibenzyl; stilbenyl; (trans-) triphenylmethyl; tetraphenylmethyl; tetraphenylethenyl; indenyl; naphthyl; 1,2,3,4-tetrahydronaphthyl; l-rnethylnaphthalene, Z-methylnaphthalene, fluorenyl; acenaphthanyl; acenaphthylenyl; anthracenyl; phenanthrenyl; fluoranthenyl; 15,16 dihydro 17H cyclopenta-(a)phenanthryl; naphthacyl; rubryl; benz(a)anthracyl; chrysenyl; triphenylyl; pyrenyl; cholanthryl; 3-methylcholanthryl; pentacyl; d1- benz(a,c)anthryl; dibenz(a,h)anthryl; picenyl; perylenyl; benzo(a)pyreny1; pyranthrenyl.
It is, therefore, an object of the present invention to provide a new composition of matter. It is a further object of this invention to provide a process for the manufacture of the new composition of matter. It is another object of this invention to provide an improved motor fuel. It is another object of this invention to provide an improved lubricating oil. It is a further object of this invention to provide a new pesticide. It is a further object of this invention to provide a motor fuel having inhibited surface ignition properties. It is a further object of this invention to provide a lubricating oil having inhibited silver, copper, and lead corrosion properties. It is a still further object of this invention to provide a lubricating oil having inhibited oxidation properties.
The following examples illustrate methods of preparing the new composition of matter but are not to be construed as limiting the invention:
EXAMPLE I Boron Di-n-Decyl Monothiophosphate The new composition was prepared by placing 785 g. of di-n-decyl dithiophosphate in a flask fitted with a stirrer, a thermometer, and a nitrogen purge tube. The next step included the addition of 39.6 g. of powdered boric acid to the flask which contained the dithiophosphate. The mixture of the di-n-decyl dithiophosphate and boric acid was heated to a temperature between 210 and 250 F. for one hour while utilizing nitrogen to purge the atmosphere within the flask. The reaction product resembled a pale yellow oil. Results of an analysis of the boron di-n-decyl monothiophosphate are as follows:
Molecular wt.:
Boron Di-Alkyl Monothiophosphate This composition was prepared by reacting P 8 with 70 mole percent isopropyl alcohol and 30 mole percent Percent B:
Calc. 1.42 Found .96 Percent P:
Calc. 12.0 Found 11.45 Percent S:
Calc. Found 15.96
The new boron monothiophosphates are, for the most ,part, oily liquids somewhat soluble in many organic solvents. They are particularly soluble in hydrocarbons. The boron monothiophosphates, when combined with a carrier, such as a spray or such as a dust composition, exert a definite toxicity against arachnids such as, for example, Tetranychus bimaculatus (two-spotted spider mite), Paratetranychus pilosus (European red mite), Bryobia praetiosa (clover mite) as well as certain small homopterous insects such as, for example, aphids. This pesticide gives excellent control of such organisms for extended periods of time.
The new toxicant may be used as a spray or as a dust compound. It may be employed in combination with an inert material carrier such as a finely divided solid, or a solvent liquid. The toxicant may be present in the inert carrier material in relatively high concentrations to provide a concentrate adapted for further dilution. It may also be present in the inert carrier material in dilute form to provide compositions suitable for application without further modification.
The following example illustrates the activity of the boron monothiophosphate as a pesticide:
EXAMPLE A A standard agricultural screening method was used to test the arachnids. The test included both the nympth and adult stage. A contact spray method was used within a Feet-Grady chamber. The chamber was operated at 5 p.s.i.g. One hundred organisms were placed on the bean plants. A concentration of 0.025% toxicant in acetone was sprayed on the bean plant. A count was made after 24 hours.
A standard agricultural screening method was used to test the aphididae family. The test included both the nympth and adult stage. A contact spray method was used within a Peet-Grady chamber. The chamber was operated at 5 p.s.i.g. One hundred organisms were placed on cotton plants. A concentration of 0.1% toxicant in acetone was sprayed on the cotton plant. A count was made after 24 hours.
Results obtained from the pesticide tests folow:
Pesticide Tests It has been proposed to add minor amounts of boron in the form of soluble or dispersable boron compounds to the liquid hydrocarbon fuels used in internal combustion engines. Among the compounds previously proposed for such purposes are the tri-alkyl borates and the tri-alkyl borines, such as tri-amyl borine and tri-isobutyl borate. This invention contemplates the addition of a boron compound which is soluble in a liquid hydrocarbon fuel and which compound contains phosphorus as well as boron.
A standard CFR L-head engine test utilizes an engine with a compression ratio of 7.0 to 1, a water temperature of 148 F. (:3 R), an oil temperature of 160 F. (i3 F.), and an air intake temperature of 110 F. (:5 F.). The test cycle is as follows:
Data obtained in a standard CRF L-head engine test are as follows:
Standard CFR L-Head Engine Test Base fuel,
Base fuel 2% boron Percent monothioreduction phosphate Surface ignition, counts/min. 350 70 These data demonstrate the utility of the boron monothiophosphate as a liquid hydrocarbon fuel additive.
A di-alkyl monothiophosphate was prepared by the reaction of P 5 with a mixture of 70 mole percent isopropyl alcohol and 30 mole percent oxodecyl alcohol and subsequent reaction with boric acid as set forth in Example II. This material was tested in a standard Timken testing machine. Such test is well known to those skilled in the art as being useful in obtaining valuable information with respect to the potential commercial value of extreme pressure lubricants. The Timken machine and test are fully described in the Journal of the Institute of Petro leum, 32, pages 209-210 and 220-222 (1946).
The data obtained for a base oil consisting of SAE-3O petroleum lubricating oil containing 3 weight percent of a barium-containing neutralized phosphorus-sulfide hydrocarbon reaction product detergent from the Timken testing machine are as follows:
These data demonstrate a substantial improvement in Timken load value resulting from the addition of a very small amount of boron monothiophosphate to a conventional petroleum lubricating oil.
The effectiveness of the boron compounds of the pres ent invention in inhibiting corrosion toward copper, silver and/or lead-containing metals and their oxidation inhibiting properties are demonstrated by data obtained by subjecting samples of the above metals to a Sand Stirring Corrosion Test. In this test a metal test specimen was slightly abraded with steel wool, Washed with naphtha, dried and weighed to the nearest mg. The cleaned test coupon was suspended in a steel beaker, cleaned with hot trisodium phosphate solution, rinsed with water, rinsed with acetone, and dried. An oil solution (250 g.) containing 1% di-n-decyl monothiophosphate was placed together with 0.625 g. lead oxide and 50 g. of a 30-35 mesh sand in the beaker. The beaker was then heated to a temperature of 300 F. (:2" F.) while the contents of the beaker were stirred by means of a stirrer which rotated at 750 r.p.m. The contents of the beaker were maintained at this temperature and under this condition for 48 hours after which the metal coupon was removed, rinsed with naphtha, dried, and weighed. Results of the test are as follows:
Sand Stirring Corrosion Test Wt. loss, mg. Material 48 hrs. 72 hrs.
Base oil 700 1. 000 Base oil 1% additive 55.1 71. 2
10% by weight of a boron phosphorus-containing compound having the formula:
wherein R and R are each the hydrocarbyl residue of an alcohol of a mixture of alcohols consisting of about 70 mole percent isopropyl alcohol and about mole percent decyl alcohol.
References Cited in the file of this patent UNITED STATES PATENTS 2,224,695 Prutton Dec. 10, 1940 2,346,156 Farrington et al Apr. 11, 1944 2,721,180 Lawrence et al. Oct. 18, 1955 2,743,235 McDermott Apr. 24, 1956 2,786,009 Pianfetti et a1 Mar. 19, 1957 2,809,163 Cyphers et al. Oct. 8, 1957 2,843,465 Yust et a1. July 15, 1958 2,885,430 Scherer et al. May 5, 1959 2,890,947 Annable et al June 16, 1959 2,920,993 Fairchild Jan. 12, 1960 2,922,812 Gilbert et al. Jan. 26, 1960 3,047,607 Thayer July 31, 1962
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US833406A US3150094A (en) | 1959-08-13 | 1959-08-13 | Lubricating oils containing boron monothiophosphate |
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US833406A US3150094A (en) | 1959-08-13 | 1959-08-13 | Lubricating oils containing boron monothiophosphate |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4755311A (en) * | 1986-08-14 | 1988-07-05 | The Lubrizol Corporation | Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same |
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US2224695A (en) * | 1938-11-25 | 1940-12-10 | Carl F Prutton | Inhibitor |
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