CA2070123A1 - Phosphates organiques et leur preparation - Google Patents

Phosphates organiques et leur preparation

Info

Publication number: CA2070123A1
Authority: CA; Canada
Prior art keywords: alkyl; substituted; phenol; resorcinol; reacting
Prior art date: 1991-06-14
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.): Abandoned

Application number

CA 2070123

Other languages

English (en)

Inventor

Charles H. Kolich

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ethyl Corp

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-06-14

Filing date

1992-06-01

Publication date

1992-12-15

1992-06-01 Application filed by Individual filed Critical Individual

1992-12-15 Publication of CA2070123A1 publication Critical patent/CA2070123A1/fr

Status Abandoned legal-status Critical Current

Links

229910019142 PO4 Inorganic materials 0.000 title claims abstract description 34
238000002360 preparation method Methods 0.000 title abstract description 4
235000021317 phosphate Nutrition 0.000 title description 30
150000003013 phosphoric acid derivatives Chemical class 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 60
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 48
-1 aryl phosphate Chemical compound 0.000 claims abstract description 44
239000010452 phosphate Substances 0.000 claims abstract description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 23
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 20
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims abstract description 20
125000003118 aryl group Chemical group 0.000 claims abstract description 14
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims abstract description 13
150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims abstract description 10
229920000388 Polyphosphate Polymers 0.000 claims abstract description 10
239000001205 polyphosphate Substances 0.000 claims abstract description 10
235000011176 polyphosphates Nutrition 0.000 claims abstract description 10
239000013067 intermediate product Substances 0.000 claims abstract description 9
150000002989 phenols Chemical class 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims description 14
239000012433 hydrogen halide Substances 0.000 claims description 11
229910000039 hydrogen halide Inorganic materials 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
239000011968 lewis acid catalyst Substances 0.000 claims description 10
OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical group C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 claims description 3
239000000446 fuel Substances 0.000 abstract description 61
239000000314 lubricant Substances 0.000 abstract description 15
239000003112 inhibitor Substances 0.000 abstract description 7
239000003063 flame retardant Substances 0.000 abstract description 2
239000000463 material Substances 0.000 abstract description 2
239000000306 component Substances 0.000 description 67
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
239000002270 dispersing agent Substances 0.000 description 33
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 30
239000002585 base Substances 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
239000003921 oil Substances 0.000 description 23
229910052698 phosphorus Inorganic materials 0.000 description 23
235000014786 phosphorus Nutrition 0.000 description 23
239000011574 phosphorus Substances 0.000 description 23
239000000654 additive Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 20
239000007788 liquid Substances 0.000 description 20
230000001050 lubricating effect Effects 0.000 description 20
229960001755 resorcinol Drugs 0.000 description 20
239000007789 gas Substances 0.000 description 19
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 16
231100000241 scar Toxicity 0.000 description 16
238000012360 testing method Methods 0.000 description 16
239000012530 fluid Substances 0.000 description 15
239000000047 product Substances 0.000 description 14
229910019213 POCl3 Inorganic materials 0.000 description 13
239000002199 base oil Substances 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
230000000996 additive effect Effects 0.000 description 12
229960005419 nitrogen Drugs 0.000 description 12
229920000768 polyamine Polymers 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
239000000370 acceptor Substances 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
230000002401 inhibitory effect Effects 0.000 description 9
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
239000011593 sulfur Substances 0.000 description 9
229940000425 combination drug Drugs 0.000 description 8
239000002904 solvent Substances 0.000 description 8
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 7
239000004809 Teflon Substances 0.000 description 7
229920006362 Teflon® Polymers 0.000 description 7
239000003963 antioxidant agent Substances 0.000 description 7
235000006708 antioxidants Nutrition 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
230000005484 gravity Effects 0.000 description 7
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000012528 membrane Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000008021 deposition Effects 0.000 description 5
125000001183 hydrocarbyl group Chemical group 0.000 description 5
238000010525 oxidative degradation reaction Methods 0.000 description 5
150000003014 phosphoric acid esters Chemical class 0.000 description 5
230000002028 premature Effects 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000010802 sludge Substances 0.000 description 5
239000002966 varnish Substances 0.000 description 5
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000010687 lubricating oil Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229960002317 succinimide Drugs 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
150000001639 boron compounds Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003518 caustics Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000002283 diesel fuel Substances 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
239000010771 distillate fuel oil Substances 0.000 description 3
229910001629 magnesium chloride Inorganic materials 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000006078 metal deactivator Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000008399 tap water Substances 0.000 description 3
235000020679 tap water Nutrition 0.000 description 3
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 3
WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 3
VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 2
LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 2
HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
241001550224 Apha Species 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
208000032544 Cicatrix Diseases 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000003599 detergent Substances 0.000 description 2
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000295 fuel oil Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
239000010705 motor oil Substances 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
229920001281 polyalkylene Polymers 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000037387 scars Effects 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
238000012546 transfer Methods 0.000 description 2
WVPGXJOLGGFBCR-UHFFFAOYSA-N trioctyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OCCCCCCCC WVPGXJOLGGFBCR-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
LJQDDVJEZIEHNY-YIMUCPRWSA-N (4r)-4-[(5r,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-n,n-dimethylpentan-1-amine Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCCN(C)C)C)[C@@]2(C)CC1 LJQDDVJEZIEHNY-YIMUCPRWSA-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
NSOAQRMLVFRWIT-UHFFFAOYSA-N 1-ethenoxydecane Chemical compound CCCCCCCCCCOC=C NSOAQRMLVFRWIT-UHFFFAOYSA-N 0.000 description 1
TUUWVHDHPUNCTO-UHFFFAOYSA-N 2,2,2-tributoxyethyl dihydrogen phosphate Chemical compound CCCCOC(COP(O)(O)=O)(OCCCC)OCCCC TUUWVHDHPUNCTO-UHFFFAOYSA-N 0.000 description 1
WALBTDFSFTVXII-UHFFFAOYSA-N 2,3,4,5,6-pentamethylphenol Chemical compound CC1=C(C)C(C)=C(O)C(C)=C1C WALBTDFSFTVXII-UHFFFAOYSA-N 0.000 description 1
PXSSNPBEHHJLDH-UHFFFAOYSA-N 2,3,4,5-tetramethylphenol Chemical compound CC1=CC(O)=C(C)C(C)=C1C PXSSNPBEHHJLDH-UHFFFAOYSA-N 0.000 description 1
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
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WCSLPBBQHFXWBW-UHFFFAOYSA-N 2-[[2-[(2-hydroxyphenyl)methylideneamino]cyclohexyl]iminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NC1C(N=CC=2C(=CC=CC=2)O)CCCC1 WCSLPBBQHFXWBW-UHFFFAOYSA-N 0.000 description 1
ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
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ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
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239000002028 Biomass Substances 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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239000004743 Polypropylene Substances 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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JEUFWFJKIXMEEK-UHFFFAOYSA-N carboxy-[2-(dicarboxyamino)ethyl]carbamic acid Chemical compound OC(=O)N(C(O)=O)CCN(C(O)=O)C(O)=O JEUFWFJKIXMEEK-UHFFFAOYSA-N 0.000 description 1
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238000005260 corrosion Methods 0.000 description 1
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MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
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PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
VDTIMXCBOXBHER-UHFFFAOYSA-N hydroxy-bis(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(S)=S VDTIMXCBOXBHER-UHFFFAOYSA-N 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
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238000003754 machining Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
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235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920002863 poly(1,4-phenylene oxide) polymer Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920006380 polyphenylene oxide Polymers 0.000 description 1
PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
238000007670 refining Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000779 smoke Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000002411 thermogravimetry Methods 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003582 thiophosphoric acids Chemical class 0.000 description 1
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
ITRFOBBKTCNNFN-UHFFFAOYSA-N tris(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound SP(S)(S)=S ITRFOBBKTCNNFN-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

CA 2070123 1991-06-14 1992-06-01 Phosphates organiques et leur preparation Abandoned CA2070123A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US71568691A	1991-06-14	1991-06-14
US715,686		1991-06-14

Publications (1)

Publication Number	Publication Date
CA2070123A1 true CA2070123A1 (fr)	1992-12-15

Family

ID=24875084

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2070123 Abandoned CA2070123A1 (fr)	1991-06-14	1992-06-01	Phosphates organiques et leur preparation

Country Status (1)

Country	Link
CA (1)	CA2070123A1 (fr)

1992
- 1992-06-01 CA CA 2070123 patent/CA2070123A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1997-06-02	FZDE	Dead

Publication	Publication Date	Title
EP0521628B1 (fr)	1996-03-20	Phosphates organiques et leur préparation
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US5185090A (en)	1993-02-09	Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing same
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US5534170A (en)	1996-07-09	Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions
US3969237A (en)	1976-07-13	Lubricant compositions containing benzotriazole derivatives as copper passivators
US4490265A (en)	1984-12-25	Lubricating compositions
US5242612A (en)	1993-09-07	Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
CA1038851A (fr)	1978-09-19	Additifs disperseurs/detersifs pour lubrifiants et carburants
US5407592A (en)	1995-04-18	Multifunctional additives
US5314633A (en)	1994-05-24	Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same
US4186102A (en)	1980-01-29	Lubricating oil composition
EP0182940A1 (fr)	1986-06-04	Bases de Mannich comme additifs pour huiles
US5205945A (en)	1993-04-27	Multifunctional additives
US4511516A (en)	1985-04-16	Boron containing heterocyclic compounds
US5348670A (en)	1994-09-20	Phosphorous amine lubricant additives
JPH0832904B2 (ja)	1996-03-29	組成物、コンセントレ−ト、潤滑剤組成物、燃料組成物、および内燃機関の燃料消費量を低減する方法
CA2070123A1 (fr)	1992-12-15	Phosphates organiques et leur preparation
US5073279A (en)	1991-12-17	Sulfur coupled hydrocarbyl derived mercaptobenzothiazole adducts as multifunctional antiwear additives and compositions containing same
CA2070131A1 (fr)	1992-12-15	Phosphates organiques et utilisation comme inhibiteurs de l'usure
US5681798A (en)	1997-10-28	Load-carrying additives based on organo-phosphites and amine phosphates
US5326487A (en)	1994-07-05	Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions
AU623670B2 (en)	1992-05-21	Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
US5387352A (en)	1995-02-07	Phosphorus-containing compositions
US5166439A (en)	1992-11-24	Composition containing a mannich base of a partially sulfurized hindered phenol mixture