CN106167506A - A kind of oil-soluble molybdenum amine complex and preparation method thereof - Google Patents
A kind of oil-soluble molybdenum amine complex and preparation method thereof Download PDFInfo
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- CN106167506A CN106167506A CN201610577959.0A CN201610577959A CN106167506A CN 106167506 A CN106167506 A CN 106167506A CN 201610577959 A CN201610577959 A CN 201610577959A CN 106167506 A CN106167506 A CN 106167506A
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- CN
- China
- Prior art keywords
- oil
- amine complex
- reaction
- fatty acid
- molybdenum amine
- Prior art date
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- 239000011733 molybdenum Substances 0.000 title claims abstract description 81
- 229910052750 molybdenum Inorganic materials 0.000 title claims abstract description 81
- -1 molybdenum amine Chemical class 0.000 title claims abstract description 76
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 238000010668 complexation reaction Methods 0.000 title abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims abstract description 38
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 21
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000011938 amidation process Methods 0.000 claims abstract description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 11
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 229930195729 fatty acid Natural products 0.000 claims abstract description 11
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 11
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 8
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 83
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 229910021529 ammonia Inorganic materials 0.000 claims description 37
- 239000000243 solution Substances 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000000725 suspension Substances 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical group O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 239000000284 extract Substances 0.000 claims description 12
- 235000021003 saturated fats Nutrition 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 11
- 239000011259 mixed solution Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 6
- 208000035126 Facies Diseases 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 1
- 235000019197 fats Nutrition 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 abstract description 13
- 230000007797 corrosion Effects 0.000 abstract description 7
- 238000005260 corrosion Methods 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000977 initiatory effect Effects 0.000 abstract description 2
- 238000005461 lubrication Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- 235000003441 saturated fatty acids Nutrition 0.000 abstract description 2
- 150000004671 saturated fatty acids Chemical class 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000004809 thin layer chromatography Methods 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 14
- 239000003921 oil Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000002199 base oil Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000010183 spectrum analysis Methods 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 5
- 239000005639 Lauric acid Substances 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- 235000021360 Myristic acid Nutrition 0.000 description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000001603 reducing effect Effects 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 3
- OOCSVLHOTKHEFZ-UHFFFAOYSA-N icosanamide Chemical compound CCCCCCCCCCCCCCCCCCCC(N)=O OOCSVLHOTKHEFZ-UHFFFAOYSA-N 0.000 description 3
- QEALYLRSRQDCRA-UHFFFAOYSA-N myristamide Chemical compound CCCCCCCCCCCCCC(N)=O QEALYLRSRQDCRA-UHFFFAOYSA-N 0.000 description 3
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- YKEWOAWDFKUUPT-UHFFFAOYSA-N 1-chlorohentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCl YKEWOAWDFKUUPT-UHFFFAOYSA-N 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 2
- 235000010894 Artemisia argyi Nutrition 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 244000030166 artemisia Species 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- CKDDRHZIAZRDBW-UHFFFAOYSA-N henicosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCC(O)=O CKDDRHZIAZRDBW-UHFFFAOYSA-N 0.000 description 2
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 244000125380 Terminalia tomentosa Species 0.000 description 1
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000003026 anti-oxygenic effect Effects 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
-
- 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
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
-
- 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
- C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/70—Soluble oils
-
- 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
- C10N2040/25—Internal-combustion engines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
The invention discloses a kind of oil-soluble molybdenum amine complex, also disclose the preparation method of this oil-soluble molybdenum amine complex.The method uses chain saturated fatty acids to be initiation material, 1 chloro satisfied fatty acid is obtained with thionyl chloride generation acyl chloride reaction, then unsaturated fatty acid amide is obtained with diethanolamine generation amidation process, last and molybdenum trioxide solution complexation obtains oil-soluble molybdenum amine complex, the molybdenum amine complex of preparation has good oil-soluble, solve existing product oil-soluble, corrosion resistance, the difficult problems captured such as antiwear and antifriction difference, significantly reduce the addition of high-sulfur phosphorus component simultaneously, huge impetus is had at the organic-molybdenum series lubrication product ground at present to domestic, thus promote the production domesticization of high-end lubricating oil, efficiently utilizing and high added value of Mo resource.
Description
Technical field
The invention belongs to lube oil additive technical field, be specifically related to a kind of oil-soluble molybdenum amine complex and preparation side thereof
Method.
Background technology
Along with fast development and the increasingly stringent of environmental conservation of auto industry, lube oil additive enterprise is faced with sternly
High challenge.Save primary energy, raising fuel economy, reduction discharge and raising engineering equipment operational efficiency to have become increasingly
Important.Organic-molybdenum is a kind of lube oil additive with excellent antiwear and friction reduction property and energy-saving effect, abroad to organic-molybdenum
Research and development are attached great importance to.The U.S. and Japan have been developed that organic-molybdenum is ground by multiple organic-molybdenum, domestic several units
Send out.
By the current automobile pollution of China and gasoline consumption figure statistics, lubricating oil adds organic-molybdenum and can save combustion every year
Oil 2,750,000 tons, is worth about 24,000,000,000 yuan；8,800,000 tons of CO2 emissions of annual minimizing；The annual electric power reducing about 80,000,000,000 yuan disappears
Consumption (is accounted for 35% calculating of total power consumption) by national industrial electricity in 2010 and motor power consumption.By the market of current organic-molybdenum,
Calculation of price, the market demand of whole world organic-molybdenum is up to 20000 tons/year, is worth about 4,000,000,000 yuan, and indirect economic effect reaches every year
To more than 100,000,000,000 yuan.Lubricating oil in world market the most extensively adds organic-molybdenum, and China is only added with in senior lubricant
Machine molybdenum, and it is mostly the phosphorous organic-molybdenum product facing market.Molybdenum amine complex is as a kind of new oil-soluble organic-molybdenum
Compound, market prospect is considerable.
Molybdenum amine complex can be used for explosive motor (containing petrol engine, Diesel engine) oil, steam engine oil, profit
Consistent lubricant and metal fluid etc., have good wear-resistant, antifriction, antioxidation and resist metal corrosion performance (particularly copper corrosion).Molybdenum
Amine complex, without P, without S or containing low S, meets environmental requirement；With S and sulfur phosphorus compound, there is synergism, add with other
Add agent and there is good compounding effect；There is more preferable antioxygenic property, it is possible to reduce greasy filth and the generation of carbon distribution, extend and use
Parts and the service life of lubricating oil.
In the world, Chinese mugwort Dicon A/S of Japan and Vanderbilt company of the U.S. have the first water inlet of synthesis molybdenum amine complex
Flat, wherein, the molybdenum amine complex that Chinese mugwort Dicon A/S produces is S-700, containing molybdenum 4.4%；Vanderbilt company of the U.S. produces
Molybdenum amine complex is MV-855, containing molybdenum 7.3%～8.5%.
Summary of the invention
The technical problem to be solved is for above-mentioned the deficiencies in the prior art, it is provided that a kind of oil-soluble molybdenum amine
Complex.This oil-soluble molybdenum amine complex has good oil-soluble, corrosion resistance, the wear-resistant function of anti-attrition and extreme pressure property.
For solving above-mentioned technical problem, the technical solution used in the present invention is: a kind of oil-soluble molybdenum amine complex, its feature
Being, structural formula is as follows:
Wherein R is C10～C20Straight chain saturated alkyl.
It addition, present invention also offers a kind of method preparing above-mentioned oil-soluble molybdenum amine complex, it is characterised in that include
Following steps:
Step one, adding reaction dissolvent dehydrated alcohol and catalyst in satisfied fatty acid, then dropping distillation is except water
Thionyl chloride, carries out acyl chloride reaction under ice bath, treats that the complete final vacuum of saturated fat acid reaction is evaporated off the thionyl chloride of excess
And dehydrated alcohol, obtain saturated fat acyl chlorides；Described catalyst is caprolactam；
Step 2, diethanolamine is dissolved in the mixed solution of ammonia and dichloromethane, then drops to institute in step one
State in saturated fat acyl chlorides, add catalyst, under ice bath, carry out amidation process；After saturated fat acyl chloride reaction is complete
Product washed and extracts, by the dried purification of organic facies of extraction, obtaining unsaturated fatty acid amide；Described catalyst is
Tetrabutyl iodate amine or tert-butyl hydroperoxide；
Step 3, unsaturated fatty acid amide described in step 2 is dissolved in organic solvent, is subsequently adding MoO3Solution,
Under nitrogen protection, temperature is back flow reaction under conditions of 100 DEG C～110 DEG C, distills after unsaturated fatty acid amide reaction completely
Remove moisture, obtain oil-soluble molybdenum amine complex.
Above-mentioned method, it is characterised in that satisfied fatty acid described in step one is C11～C21Straight chain saturated fat
Acid, satisfied fatty acid is 1:1.5～1:2 with the mol ratio of the thionyl chloride that distillation removes water.
Above-mentioned method, it is characterised in that the quality of catalyst described in step one is satisfied fatty acid and thionyl chloride
The 2%～3% of gross mass.
Above-mentioned method, it is characterised in that described in step one, the speed of dropping is 1/s～2/s.
Above-mentioned method, it is characterised in that the temperature of acyl chloride reaction described in step one is-5 DEG C～0 DEG C.
Above-mentioned method, it is characterised in that in step 2 the mol ratio of saturated fat acyl chloride and diethanolamine be 1:1.2～
The volume ratio of 1:2, ammonia and dichloromethane is 1:8～1:10, after diethanolamine is dissolved in the mixed solution of ammonia and dichloromethane
The pH value of solution is 9～10.
Above-mentioned method, it is characterised in that the temperature of amidation process described in step 2 is-5 DEG C～0 DEG C, amidatioon
The pH value using ammonia regulation reactant liquor in course of reaction is 8～9.
Above-mentioned method, it is characterised in that the quality of catalyst described in step 2 is saturated fat acyl chlorides and diethanol
The 2%～3% of amine gross mass.
Above-mentioned method, it is characterised in that MoO described in step 33The preparation method of solution is: by MoO3And deionization
Water mix homogeneously obtains suspension, under conditions of temperature is 40 DEG C～50 DEG C, drips ammonia to suspended in described suspension
The pH value of liquid is 7～9, obtains MoO3Solution.
The present invention compared with prior art has the advantage that
1, the oil-soluble molybdenum amine complex of the present invention has good oil-soluble, corrosion resistance, the wear-resistant function of anti-attrition and pole
Pressure performance.
2, the present invention uses chain saturated fatty acids to be initiation material, obtains 1-chlorine with thionyl chloride generation acyl chloride reaction
For satisfied fatty acid, then obtain unsaturated fatty acid amide with diethanolamine generation amidation process, the most molten with molybdenum trioxide
Liquid complexation obtains oil-soluble molybdenum amine complex, and the molybdenum amine complex of preparation has good oil-soluble, solves existing product oil soluble
Property, the difficult problem captured such as corrosion resistance, antiwear and antifriction difference, significantly reduce the addition of high-sulfur phosphorus component, to state simultaneously
Interior have huge impetus at the organic-molybdenum series lubrication product ground at present, thus promotes the production domesticization of high-end lubricating oil, molybdenum
Efficiently utilizing and high added value of resource.
Below in conjunction with the accompanying drawings and embodiment, technical scheme is described in further detail.
Figure of description
Fig. 1 be the oil-soluble molybdenum amine complex prepared of Example 1 and Example 2 of the present invention with MOLYVAN855 at base oil
In SRV friction coefficient curve.
Detailed description of the invention
Embodiment 1
The oil-soluble molybdenum amine complex of the present embodiment, structural formula is as follows:
Wherein R is pentadecyl.
The preparation method of the oil-soluble molybdenum amine complex of the present embodiment comprises the following steps:
Step one, accurately weigh 25.8g (0.1mol) Palmic acid and add in 250mL there-necked flask, to described there-necked flask
Middle addition 50mL dehydrated alcohol and 2g catalyst caprolactam, then drip 23.8g (0.2mol) distillation and remove the thionyl chloride of water,
Rate of addition is 2/s, carries out acyl chloride reaction under-5 DEG C of ice baths, uses thin layer chromatography (TLC) to follow the tracks of reaction, treats raw material palm fibre
The complete final vacuum of palmitic acid acid reaction is evaporated off thionyl chloride and the dehydrated alcohol of excess, obtains 1-chloro Palmic acid；
Step 2,15.7g (0.15mol) diethanolamine is dissolved in mixed solution (ammonia and two of ammonia and dichloromethane
The volume ratio of chloromethanes is 1:8) in, after dissolving, the pH value of solution is 9, then drops to the Palmic acid of 1-chloro described in step one
In, add 2g catalyst tetrabutyl iodate amine, under-5 DEG C of ice baths, carry out amidation process, course of reaction uses ammonia adjust
The pH value of joint reactant liquor is 8～9, uses thin layer chromatography (TLC) to follow the tracks of reaction to the reaction of 1-chloro Palmic acid completely, reaction is produced
Thing washs with saturated aqueous common salt after washing with saturated sodium bicarbonate again, finally extracts with dichloromethane, the organic facies of extraction is used
Anhydrous magnesium sulfate is purified with silica gel column chromatography after drying, and silica gel column chromatography flowing used is the mixed liquor of dichloromethane and methanol mutually
(volume ratio is CH2Cl2:CH3OH=5:1), the palmitamide that quality purity is more than 98% is obtained；
Step 3, palmitamide described in step 2 is dissolved in toluene, is subsequently adding MoO3Solution, protects at nitrogen
Under, temperature is back flow reaction under conditions of 100 DEG C, uses thin layer chromatography (TLC) to follow the tracks of reaction to palmitamide reaction completely
After moisture is distilled off, obtain the oil-soluble molybdenum amine complex of brown viscous shape；Described MoO3The preparation method of solution is: will
MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 40 DEG C, in described suspension, drip ammonia
PH value to suspension is 9, obtains MoO3Solution.
The nuclear magnetic resonance map of oil-soluble molybdenum amine complex prepared by the present embodiment shows:1H NMR(400MHz,CDCl3)δ
It is CH at 3.792Peak on-O-Mo, is-N-CH at δ 3.392On peak, be-CH at δ 2.342Peak on-C=O, at δ 1.54
For-(CH2)n-CH2-peak, be-(CH at δ 1.262)nPeak, δ 0.88 is-CH3Peak, determine sky by proton nmr spectra
Between stereochemical structure.Mass spectral analysis m/z:471.19 (100.0%), 469.19 (76.8%), 468.19 (67.1%), 465.19
(55.4%), 470.19 (50.1%), 473.19 (38.9%), 476.19 (35.1%), 472.19 (20.8%), 466.19
(12.3%), 474.19 (8.0%), 470.20 (1.5%), 467.20 (1.3%), 472.20 (1.1%).Elementary analysis: survey
Definite value: C 51.20%；H 8.35%；N 2.96；O 17.12；Theoretical value C 51.17%；H 8.37%；N 2.98；O
17.04；Chemical structural formula: C20H39MoNO5, molecular weight 469.49.
Embodiment 2
The oil-soluble molybdenum amine complex of the present embodiment, structural formula is as follows:
Wherein R is nonadecyl.
The preparation method of the oil-soluble molybdenum amine complex of the present embodiment comprises the following steps:
Step one, accurately weigh 31.3g (0.1mol) arachidic acid and add in 250mL there-necked flask, to described there-necked flask
Middle addition 50mL dehydrated alcohol and 2g catalyst caprolactam, then drip 23.8g (0.2mol) distillation and remove the thionyl chloride of water,
Rate of addition is 1/s, carries out acyl chloride reaction under-3 DEG C of ice baths, uses thin layer chromatography (TLC) to follow the tracks of reaction, treats raw material flower
The raw complete final vacuum of acid reaction is evaporated off thionyl chloride and the dehydrated alcohol of excess, obtains 1-chloro arachidic acid；
Step 2,15.7g (0.15mol) diethanolamine is dissolved in mixed solution (ammonia and two of ammonia and dichloromethane
The volume ratio of chloromethanes is 1:10) in, after dissolving, the pH value of solution is 10, then drops to the Semen arachidis hypogaeae of 1-chloro described in step one
In acid, add 2g catalyst tert-butyl hydroperoxide, under-3 DEG C of ice baths, carry out amidation process, course of reaction uses ammonia
The pH value of water regulation reactant liquor is 8～9, uses thin layer chromatography (TLC) to follow the tracks of reaction to the reaction of 1-chloro arachidic acid completely, will be anti-
Wash with saturated aqueous common salt again after answering the washing of product saturated sodium bicarbonate, finally extract with dichloromethane, organic by extract
Purifying with silica gel column chromatography after drying with anhydrous magnesium sulfate, silica gel column chromatography flowing used be mixing of dichloromethane and methanol mutually
(volume ratio is CH to close liquid2Cl2:CH3OH=5:1), the arachidamide that quality purity is more than 98% is obtained；
Step 3, arachidamide described in step 2 is dissolved in toluene, is subsequently adding MoO3Solution, protects at nitrogen
Under, temperature is back flow reaction under conditions of 110 DEG C, uses thin layer chromatography (TLC) to follow the tracks of reaction to arachidamide reaction completely
After moisture is distilled off, obtain the oil-soluble molybdenum amine complex of brown viscous shape；Described MoO3The preparation method of solution is: will
MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 45 DEG C, in described suspension, drip ammonia
PH value to suspension is 7, obtains MoO3Solution.
The nuclear magnetic resonance map of oil-soluble molybdenum amine complex prepared by the present embodiment shows:1H NMR(400MHz,CDCl3)δ
It is CH at 3.792Peak on-O-Mo, is-N-CH at δ 3.392On peak, be-CH at δ 2.342Peak on-C=O, at δ 1.54
For-(CH2)n-CH2The peak at-place, is-(CH at δ 1.262)nPeak, δ 0.88 is-CH3The peak at place, true by proton nmr spectra
Determine stereoeffect.Mass spectral analysis m/z:527.25 (100.0%), 525.25 (78.2%), 524.25 (68.5%),
521.25 (55.3%), 526.25 (52.1%), 529.25 (36.0%), 523.25 (34.5%), 528.25 (23.7%),
522.26 (14.8%), 530.26 (10.1%), 529.26 (4.2%), 526.26 (3.2%), 527.26 (2.7%),
528.26 (2.6%), 523.26 (2.5%), 531.26 (1.6%), 525.26 (1.6%).Elementary analysis: measured value C
54.90%；H 8.98%；N 2.71；O 15.13.Theoretical value C 54.84%；H 9.01%；N 2.66；O 15.22.Chemistry
Structural formula: C24H47MoNO5, molecular weight 525.59.
Embodiment 3
The oil-soluble molybdenum amine complex of the present embodiment, structural formula is as follows:
Wherein R is tridecyl.
The preparation method of the oil-soluble molybdenum amine complex of the present embodiment comprises the following steps:
Step one, accurately weigh 22.8g (0.1mol) myristic acid and add in 250mL there-necked flask, to described there-necked flask
Middle addition 50mL dehydrated alcohol and 2g catalyst caprolactam, then drip 17.85g (0.15mol) distillation except the protochloride of water
Sulfone, rate of addition is 1/s, carries out acyl chloride reaction under 0 DEG C of ice bath, uses thin layer chromatography (TLC) to follow the tracks of reaction, treats raw material
Myristic acid reacts complete final vacuum and thionyl chloride and the dehydrated alcohol of excess is evaporated off, and obtains 1-chloro myristic acid；
Step 2,12.56g (0.12mol) diethanolamine is dissolved in mixed solution (ammonia and two of ammonia and dichloromethane
The volume ratio of chloromethanes is 1:9) in, after dissolving, the pH value of solution is 9.5, then drops to the Fructus Amomi Rotundus of 1-chloro described in step one
In acid, add 2g catalyst tetrabutyl iodate amine, under 0 DEG C of ice bath, carry out amidation process, course of reaction uses ammonia
The pH value of regulation reactant liquor is 8～9, uses thin layer chromatography (TLC) to follow the tracks of reaction to the reaction of 1-chloro myristic acid completely, will reaction
Product washs with saturated aqueous common salt after washing with saturated sodium bicarbonate again, finally extracts with dichloromethane, by the organic facies of extraction
Purifying with silica gel column chromatography after drying with anhydrous magnesium sulfate, silica gel column chromatography flowing used is the mixing of dichloromethane and methanol mutually
(volume ratio is CH to liquid2Cl2:CH3OH=5:1), the myristic acid amide that quality purity is more than 98% is obtained；
Step 3, myristic acid amide described in step 2 is dissolved in toluene, is subsequently adding MoO3Solution, protects at nitrogen
Under, temperature is back flow reaction under conditions of 105 DEG C, uses thin layer chromatography (TLC) to follow the tracks of reaction to the reaction of myristic acid amide completely
After moisture is distilled off, obtain the oil-soluble molybdenum amine complex of brown viscous shape；Described MoO3The preparation method of solution is: will
MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 50 DEG C, in described suspension, drip ammonia
PH value to suspension is 8, obtains MoO3Solution.
The nuclear magnetic resonance map of oil-soluble molybdenum amine complex prepared by the present embodiment shows:1H NMR(400MHz,CDCl3)δ
It is CH at 3.792Peak on-O-Mo, is-N-CH at δ 3.392On peak, be-CH at δ 2.342Peak on-C=O, at δ 1.54
For-(CH2)n-CH2The peak at-place, is-(CH at δ 1.262)nPeak, δ 0.88 is-CH3The peak at place.True by proton nmr spectra
Determine stereoeffect, mass spectral analysis m/z:527.25 (100.0%), 525.25 (78.2%), 524.25 (68.5%),
521.25 (55.3%), 526.25 (52.1%), 529.25 (36.0%), 523.25 (34.5%), 528.25 (23.7%),
522.26 (14.8%), 530.26 (10.1%), 529.26 (4.2%), 526.26 (3.2%), 527.26 (2.7%),
528.26 (2.6%), 523.26 (2.5%), 531.26 (1.6%), 525.26 (1.6%).Elementary analysis: measured value C
51.27%；H 8.75%；N 2.86；O 17.44.Theoretical value C 51.20%；H 8.35%；N 2.96；O 17.12.Chemistry
Structural formula: C18H35MoNO5, molecular weight 441.43.
Embodiment 4
The oil-soluble molybdenum amine complex of the present embodiment, structural formula is as follows:
Wherein R is undecyl.
The preparation method of the oil-soluble molybdenum amine complex of the present embodiment comprises the following steps:
Step one, accurately weigh 20.0g (0.1mol) lauric acid and add in 250mL there-necked flask, to described there-necked flask
Middle addition 50mL dehydrated alcohol and 2g catalyst caprolactam, then drip 21.42g (0.18mol) distillation except the protochloride of water
Sulfone, rate of addition is 2/s, carries out acyl chloride reaction under-2 DEG C of ice baths, uses thin layer chromatography (TLC) to follow the tracks of reaction, treats former
Material lauric acid reacts complete final vacuum and thionyl chloride and the dehydrated alcohol of excess is evaporated off, and obtains 1-chloro lauric acid；
Step 2,20.93g (0.2mol) diethanolamine is dissolved in mixed solution (ammonia and two of ammonia and dichloromethane
The volume ratio of chloromethanes is 1:10) in, after dissolving, the pH value of solution is 9, then drops to the Laurel of 1-chloro described in step one
In acid, add 2g catalyst tert-butyl hydroperoxide, under-2 DEG C of ice baths, carry out amidation process, course of reaction uses ammonia
The pH value of water regulation reactant liquor is 8～9, uses thin layer chromatography (TLC) to follow the tracks of reaction to the reaction of 1-chloro lauric acid completely, will be anti-
Wash with saturated aqueous common salt again after answering the washing of product saturated sodium bicarbonate, finally extract with dichloromethane, organic by extract
Purifying with silica gel column chromatography after drying with anhydrous magnesium sulfate, silica gel column chromatography flowing used be mixing of dichloromethane and methanol mutually
(volume ratio is CH to close liquid2Cl2:CH3OH=5:1), the lauric amide that quality purity is more than 98% is obtained；
Step 3, lauric amide described in step 2 is dissolved in toluene, is subsequently adding MoO3Solution, protects at nitrogen
Under, temperature is back flow reaction under conditions of 105 DEG C, uses thin layer chromatography (TLC) to follow the tracks of reaction to lauric amide reaction completely
After moisture is distilled off, obtain the oil-soluble molybdenum amine complex of brown viscous shape；Described MoO3The preparation method of solution is: will
MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 40 DEG C, in described suspension, drip ammonia
PH value to suspension is 9, obtains MoO3Solution.
The nuclear magnetic resonance map of oil-soluble molybdenum amine complex prepared by the present embodiment shows:1H NMR(400MHz,CDCl3)δ
It is CH at 3.792Peak on-O-Mo, is-N-CH at δ 3.392On peak, be-CH at δ 2.342Peak on-C=O, at δ 1.54
For-(CH2)n-CH2The peak at-place, is-(CH at δ 1.262)nPeak, δ 0.88 is-CH3The peak at place, true by proton nmr spectra
Determine stereoeffect.Mass spectral analysis m/z:415.13 (100.0%), 412.13 (66.9%), 413.12 (63.7%),
409.13 (56.4%), 414.13 (49.2%), 417.13 (39.0%), 411.13 (36.6%), 416.13 (17.5%),
413.13 (11.7%), 410.13 (10.1%), 418.13 (6.7%).Elementary analysis: measured value C 46.49%；H
7.56%；N 3.39；O 19.35.Theoretical value C 46.43%；H 7.76%；N 3.42；O 19.20.Chemical structural formula:
C16H31MoNO5, molecular weight 413.38.
Embodiment 5
The oil-soluble molybdenum amine complex of the present embodiment, structural formula is as follows:
Wherein R is heptadecyl.
The preparation method of the oil-soluble molybdenum amine complex of the present embodiment comprises the following steps:
Step one, accurately weigh 28.4g (0.1mol) stearic acid and add in 250mL there-necked flask, to described there-necked flask
Middle addition 50mL dehydrated alcohol and 2g catalyst caprolactam, then drip 23.8g (0.2mol) distillation and remove the thionyl chloride of water,
Rate of addition is 1/s, carries out acyl chloride reaction under-5 DEG C of ice baths, uses thin layer chromatography (TLC) to follow the tracks of reaction, treats that raw material is hard
Fat acid reacts complete final vacuum and thionyl chloride and the dehydrated alcohol of excess is evaporated off, and obtains 1-chloro-stearic acid；
Step 2,15.7g (0.15mol) diethanolamine is dissolved in mixed solution (ammonia and two of ammonia and dichloromethane
The volume ratio of chloromethanes is 1:8) in, after dissolving, the pH value of solution is 10, then drops to 1-chloro described in step one stearic
In acid, add 2g catalyst tert-butyl hydroperoxide, under-5 DEG C of ice baths, carry out amidation process, course of reaction uses ammonia
The pH value of water regulation reactant liquor is 8～9, uses thin layer chromatography (TLC) to follow the tracks of reaction to the reaction of 1-chloro-stearic acid completely, will be anti-
Wash with saturated aqueous common salt again after answering the washing of product saturated sodium bicarbonate, finally extract with dichloromethane, organic by extract
Purifying with silica gel column chromatography after drying with anhydrous magnesium sulfate, silica gel column chromatography flowing used be mixing of dichloromethane and methanol mutually
(volume ratio is CH to close liquid2Cl2:CH3OH=5:1), the stearic amide that quality purity is more than 98% is obtained；
Step 3, stearic amide described in step 2 is dissolved in toluene, is subsequently adding MoO3Solution, protects at nitrogen
Under, temperature is back flow reaction under conditions of 110 DEG C, uses thin layer chromatography (TLC) to follow the tracks of reaction to stearic amide reaction completely
After moisture is distilled off, obtain the oil-soluble molybdenum amine complex of brown viscous shape；Described MoO3The preparation method of solution is: will
MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 50 DEG C, in described suspension, drip ammonia
PH value to suspension is 7, obtains MoO3Solution.
The nuclear magnetic resonance map of oil-soluble molybdenum amine complex prepared by the present embodiment shows:1H NMR(400MHz,CDCl3)δ
It is CH at 3.792Peak on-O-Mo, is-N-CH at δ 3.392On peak, be-CH at δ 2.342Peak on-C=O, at δ 1.54
For-(CH2)n-CH2The peak at-place, is-(CH at δ 1.262)nPeak, δ 0.88 is-CH3The peak at place, true by proton nmr spectra
Determine stereoeffect.Mass spectral analysis m/z:499.22 (100.0%), 497.22 (77.5%), 496.22 (68.5%),
493.22 (55.7%), 498.22 (51.8%), 501.22 (37.2%), 495.22 (34.8%), 500.22 (22.5%),
494.22 (13.5%), 502.22 (8.7%), 501.23 (2.8%), 499.23 (2.3%), 498.23 (2.2%), 495.23
(2.2%), 500.23 (1.4%), 497.23 (1.3%).Elementary analysis: measured value C 51.20%；H 8.35%；N 2.96；
O 17.12.Theoretical value C 53.11%；H 8.71%；N 2.82；O 16.08.Chemical structural formula: C22H43MoNO5, molecular weight
499.22。
Embodiment 6
The oil-soluble molybdenum amine complex of the present embodiment, structural formula is as follows:
Wherein R is eicosyl.
The preparation method of the oil-soluble molybdenum amine complex of the present embodiment comprises the following steps:
Step one, accurately weigh 32.6g (0.1mol) heneicosanoic acid and add in 250mL there-necked flask, to described three mouthfuls
Flask adds 50mL dehydrated alcohol and 2g catalyst caprolactam, then drips 23.8g (0.2mol) distillation except the chlorination of water
Sulfoxide, rate of addition is 1/s, carries out acyl chloride reaction under-5 DEG C of ice baths, uses thin layer chromatography (TLC) to follow the tracks of reaction, treats
The complete final vacuum of raw material hentriacontane acid reaction is evaporated off thionyl chloride and the dehydrated alcohol of excess, obtains 1-chloro hentriacontane
Acid；
Step 2,15.7g (0.15mol) diethanolamine is dissolved in mixed solution (ammonia and two of ammonia and dichloromethane
The volume ratio of chloromethanes is 1:8) in, after dissolving, the pH value of solution is 10, then drops to 1-chloro described in step one 30
In one alkanoic acid, add 2g catalyst tetrabutyl iodate amine, under-5 DEG C of ice baths, carry out amidation process, course of reaction uses
The pH value of ammonia regulation reactant liquor is 8～9, uses thin layer chromatography (TLC) to follow the tracks of reaction complete to 1-chloro hentriacontane acid reaction
Entirely, wash with saturated aqueous common salt again after product is washed with saturated sodium bicarbonate, finally extract with dichloromethane, will extraction
Organic facies purify with silica gel column chromatography after drying with anhydrous magnesium sulfate, silica gel column chromatography flowing used is dichloromethane and first mutually
(volume ratio is CH to the mixed liquor of alcohol2Cl2:CH3OH=5:1), the myricinic acid amide that quality purity is more than 98% is obtained；
Step 3, myricinic acid amide described in step 2 is dissolved in toluene, is subsequently adding MoO3Solution, at nitrogen
Under protection, temperature is back flow reaction under conditions of 105 DEG C, uses thin layer chromatography (TLC) to follow the tracks of reaction to myricinic acid amide
Moisture is distilled off after reaction completely, obtains the oil-soluble molybdenum amine complex of brown viscous shape；Described MoO3The preparation side of solution
Method is: by MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 45 DEG C, drip in described suspension
Adding ammonia to the pH value of suspension is 7, obtains MoO3Solution.
The nuclear magnetic resonance map of oil-soluble molybdenum amine complex prepared by the present embodiment shows:1H NMR(400MHz,CDCl3)δ
It is CH at 3.792Peak on-O-Mo, is-N-CH at δ 3.392On peak, be-CH at δ 2.342Peak on-C=O, at δ 1.54
For-(CH2)n-CH2The peak at-place, is-(CH at δ 1.262)nPeak, δ 0.88 is-CH3The peak at place, true by proton nmr spectra
Determine stereoeffect.Mass spectral analysis m/z:541.27 (100.0%), 539.27 (78.0%), 538.27 (67.0%),
540.27 (54.2%), 535.27 (53.7%), 543.27 (39.1%), 537.27 (36.0%), 542.27 (26.1%),
536.27 (14.9%), 544.27 (10.1%), 545.28 (1.3%) elementary analysiss: measured value C 55.20%；H 9.35%；
N 2.96；O 14.12.Theoretical value C55.64%；H 9.15%；N 2.60；O 14.82.Chemical structural formula: C25H49MoNO5, point
Son amount 539.62.
Embodiment 7
The oil-soluble molybdenum amine complex of the present embodiment, structural formula is as follows:
Wherein R is decyl.
The preparation method of the oil-soluble molybdenum amine complex of the present embodiment comprises the following steps:
Step one, accurately weigh 18.6g (0.1mol) hendecanoic acid and add in 250mL there-necked flask, to described three mouthfuls of burnings
Add 50mL dehydrated alcohol and 2g catalyst caprolactam in Ping, then drip 23.8g (0.2mol) distillation except the protochloride of water
Sulfone, rate of addition is 1/s, carries out acyl chloride reaction under-5 DEG C of ice baths, uses thin layer chromatography (TLC) to follow the tracks of reaction, treats former
Material hendecanoic acid reacts complete final vacuum and thionyl chloride and the dehydrated alcohol of excess is evaporated off, and obtains 1-chloro hendecanoic acid；
Step 2,15.7g (0.15mol) diethanolamine is dissolved in mixed solution (ammonia and two of ammonia and dichloromethane
The volume ratio of chloromethanes is 1:8) in, after dissolving, the pH value of solution is 10, then drops to 1-chloro described in step one 11
In alkanoic acid, add 2g catalyst tetrabutyl iodate amine, under-5 DEG C of ice baths, carry out amidation process, course of reaction uses ammonia
The pH value of water regulation reactant liquor is 8～9, uses thin layer chromatography (TLC) to follow the tracks of reaction to the reaction of 1-chloro hendecanoic acid completely, will
Product is washed with saturated aqueous common salt after washing with saturated sodium bicarbonate again, finally extracts with dichloromethane, by having of extraction
Machine anhydrous magnesium sulfate is purified with silica gel column chromatography after drying, and silica gel column chromatography flowing used is dichloromethane and methanol mutually
(volume ratio is CH to mixed liquor2Cl2:CH3OH=5:1), the hendecanoic acid amide that quality purity is more than 98% is obtained；
Step 3, hendecanoic acid amide described in step 2 is dissolved in toluene, is subsequently adding MoO3Solution, protects at nitrogen
Protecting down, temperature is back flow reaction under conditions of 100 DEG C, uses thin layer chromatography (TLC) to follow the tracks of reaction and reacts to hendecanoic acid amide
Moisture is distilled off after Wan Quan, obtains the oil-soluble molybdenum amine complex of brown viscous shape；Described MoO3The preparation method of solution is:
By MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 50 DEG C, in described suspension, drip ammonia
Water is 7 to the pH value of suspension, obtains MoO3Solution.
The nuclear magnetic resonance map of oil-soluble molybdenum amine complex prepared by the present embodiment shows:1H NMR(400MHz,CDCl3)δ
It is CH at 3.792Peak on-O-Mo, is-N-CH at δ 3.392On peak, be-CH at δ 2.342Peak on-C=O, at δ 1.54
For-(CH2)n-CH2The peak at-place, is-(CH at δ 1.262)nPeak, δ 0.88 is-CH3The peak at place, true by proton nmr spectra
Determine stereoeffect.Mass spectral analysis m/z:401.11 (100.0%), 399.11 (75.1%), 398.11 (67.4%),
395.11 (57.3%), 400.11 (48.3%), 403.11 (38.2%), 397.11 (35.7%), 402.11 (16.0%),
396.11 (9.5%), 404.12 (6.5%), 397.12 (1.3%), 403.12 (1.3%), 401.12 (1.1%), 400.12
(1.1%) elementary analysis: measured value C 45.20%；H 7.35%；N 3.96；O 20.12.Theoretical value C 45.11%；H
7.32%；N 3.51；O 20.03.Chemical structural formula: C15H29MoNO5, molecular weight 401.11.
The oil-soluble molybdenum amine complex of the present invention can compound in compositions of additives as a kind of single dose, it is also possible to directly
Adding to lubricating oil, range of application and recommendation add dosage and are:
(1) I. C. engine oil adds dosage: 0.2wt%～0.6wt%；
(2) automatic transmission fluid and accelerator oil adds dosage: 0.2wt%～1wt%.
The oil-soluble of oil-soluble molybdenum amine complex of the present invention and THERMAL STABILITY:
Embodiment 1 to embodiment 7 is prepared oil-soluble molybdenum amine complex be separately added in conventional API/CF-4 15W/40,
Adding dosage is 0.5wt%, places 500h, observes all without precipitation in the range of temperature (-20 DEG C～60 DEG C), and oil product is as clear as crystal.
More than more than 276 DEG C, decomposing phenomenon is just occurring, illustrating that product has outstanding oil-soluble and heat stability.
The anticorrosion of oil-soluble molybdenum amine complex of the present invention and antioxygen property research:
Employing standard GB/T11143 detects, and adding dosage is 0.5wt%, observes product embodiments 1 to embodiment 7 and makes
The anticorrosion of standby oil-soluble molybdenum amine complex and antioxygen property, concrete outcome such as following table:
| Environment | Tap water | Synthetic seawater | Distilled water |
| Copper corrosion | 1b(GB/T5096) | 1b(GB/T5096) | 1b(GB/T5096) |
| Embodiment 1 | Corrosion-free | Corrosion-free | Corrosion-free |
| Embodiment 2 | Corrosion-free | Corrosion-free | Corrosion-free |
| Embodiment 3 | Corrosion-free | Corrosion-free | Corrosion-free |
| Embodiment 4 | Corrosion-free | Corrosion-free | Corrosion-free |
| Embodiment 5 | Corrosion-free | Corrosion-free | Corrosion-free |
| Embodiment 6 | Corrosion-free | Corrosion-free | Corrosion-free |
| Embodiment 7 | Corrosion-free | Corrosion-free | Corrosion-free |
The Wear vesistance research of oil-soluble molybdenum amine complex of the present invention:
The oil-soluble molybdenum amine complex of embodiment 1 and embodiment 2 is dissolved separately in base oil, the product sold with market
Product U.S. Vanderbilt MOLYVAN855 (brown liquid, Mo content 4.91%) Wear vesistance compares.Testing equipment is adopted
With introduce from OPTIMAL company of Germany4 type friction wear testing machines, testpieces is linear contact lay friction pair.Test
Time, by the oil sample injection testing dish of about 300 μ L, test board is fixed, and contacts with upper testpieces cylinder, and cylinder is with main shaft one
Rise and move back and forth, form linear contact lay forms of motion, move back and forth with certain load, stroke and frequency, measure not
With additive coefficient of friction at different temperatures, to evaluate the friction reducing effect of additive in oil product, result is shown in Fig. 1.
As can be seen from Figure 1: the oil-soluble molybdenum amine complex of the present invention and U.S.'s Vanderbilt MOLYVAN855 product
Coefficient of friction under same dose is suitable, and temperature influence is less when less than 120 DEG C.
The abrasion resistance research of oil-soluble molybdenum amine complex of the present invention:
The abrasion resistance of the oil-soluble molybdenum amine complex of embodiment 1 and embodiment 2 with MOLYVAN855 is compared.Will
The oil-soluble molybdenum amine complex of embodiment 1 and embodiment 2 and MOLYVAN855 call in base oil respectively with the dosage of 0.5wt%
In, according to GB3142-82, utilize four ball to evaluate the wear scar diameter under 196N and extreme pressure four ball maximum nonseizure load P respectivelyB
Value, result of the test is shown in Table 1.
Table 1 abrasion resistance comparing result
| Project | Mill speckle/mm | PBValue (N) |
| The oil-soluble molybdenum amine complex of base oil+0.5% embodiment 1 | 0.53 | 405.5 |
| The oil-soluble molybdenum amine complex of base oil+0.5% embodiment 1 | 0.50 | 410.2 |
| Base oil+0.5%MOLYVAN855 | 0.52 | 409.7 |
From table 1 it follows that the oil-soluble molybdenum amine complex of Example 1 and Example 2 of the present invention and MOLYVAN855
Maximum in base oil stings load P without clickBWith maximum sintering load PDQuite, illustrate that they have preferable extreme pressure property.
By above-mentioned performance comparison it can be seen that the oil-soluble molybdenum amine complex of the present invention has preferable tribology
Can, the antiwear and reducing friction performance of lubricating oil can be greatly improved as lube oil additive, protecting film can be formed at surface of friction pair, bright
The aobvious using effect reducing lubricating oil product, can expand the load range of oil product, additionally, this series products has preferable extreme pressure
Performance so that lubricating oil can bear certain high pressure load.And during using, do not produce the harm gas such as sulfur phosphorus, beneficially three
Unit urges device and exhaust emissions.
The above, be only presently preferred embodiments of the present invention, and the present invention not does any restriction, every according to invention skill
Any simple modification, change and the equivalent structure change that above example is made by art essence, all still falls within the technology of the present invention
In the protection domain of scheme.
Claims (10)
1. an oil-soluble molybdenum amine complex, it is characterised in that structural formula is as follows:
Wherein R is C10～C20Straight chain saturated alkyl.
2. the method preparing oil-soluble molybdenum amine complex as claimed in claim 1, it is characterised in that comprise the following steps:
Step one, adding reaction dissolvent dehydrated alcohol and catalyst in satisfied fatty acid, then dropping distillation is except the chlorination of water
Sulfoxide, carries out acyl chloride reaction under ice bath, treats that the complete final vacuum of saturated fat acid reaction is evaporated off thionyl chloride and the nothing of excess
Water-ethanol, obtains saturated fat acyl chlorides；Described catalyst is caprolactam；
Step 2, diethanolamine is dissolved in the mixed solution of ammonia and dichloromethane, then drops to described in step one full
With in fat acyl chloride, add catalyst, under ice bath, carry out amidation process；Will be anti-after saturated fat acyl chloride reaction is complete
Answer product to wash and extract, by the dried purification of organic facies of extraction, obtaining unsaturated fatty acid amide；Described catalyst is four fourths
Base iodate amine or tert-butyl hydroperoxide；
Step 3, unsaturated fatty acid amide described in step 2 is dissolved in organic solvent, is subsequently adding MoO3Solution, at nitrogen
Under protection, temperature is back flow reaction under conditions of 100 DEG C～110 DEG C, is distilled off after unsaturated fatty acid amide reaction completely
Moisture, obtains oil-soluble molybdenum amine complex.
Method the most according to claim 2, it is characterised in that satisfied fatty acid described in step one is C11～C21Straight chain
Satisfied fatty acid, satisfied fatty acid is 1:1.5～1:2 with the mol ratio of the thionyl chloride that distillation removes water.
Method the most according to claim 2, it is characterised in that the quality of catalyst described in step one is satisfied fatty acid
With thionyl chloride gross mass 2%～3%.
Method the most according to claim 2, it is characterised in that the speed of dropping described in step one be 1/s～2/
s。
Method the most according to claim 2, it is characterised in that the temperature of acyl chloride reaction described in step one be-5 DEG C～
0℃。
Method the most according to claim 2, it is characterised in that in step 2 saturated fat acyl chloride and diethanolamine mole
Than be the volume ratio of 1:1.2～1:2, ammonia and dichloromethane be 1:8～1:10, diethanolamine is dissolved in ammonia and dichloromethane
After mixed solution, the pH value of solution is 9～10.
Method the most according to claim 2, it is characterised in that the temperature of amidation process described in step 2 be-5 DEG C～
0 DEG C, the pH value using ammonia regulation reactant liquor during amidation process is 8～9.
Method the most according to claim 2, it is characterised in that the quality of catalyst described in step 2 is saturated fat acyl
Chlorine and the 2% of diethanolamine gross mass～3%.
Method the most according to claim 2, it is characterised in that MoO described in step 33The preparation method of solution is: will
MoO3Obtain suspension with deionized water mix homogeneously, under conditions of temperature is 40 DEG C～50 DEG C, drip in described suspension
Adding ammonia to the pH value of suspension is 7～9, obtains MoO3Solution.
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