CN107903285A - 一种中性磷酸酯离子液体及其应用 - Google Patents
一种中性磷酸酯离子液体及其应用 Download PDFInfo
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 44
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 27
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 26
- 239000010452 phosphate Substances 0.000 title claims abstract description 26
- 230000007935 neutral effect Effects 0.000 title claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 22
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- 150000001412 amines Chemical class 0.000 claims abstract description 11
- 229920000570 polyether Polymers 0.000 claims abstract description 10
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 12
- 239000007866 anti-wear additive Substances 0.000 claims description 8
- -1 polyol ester Chemical class 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000005591 trimellitate group Chemical group 0.000 claims description 5
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002191 fatty alcohols Chemical class 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 3
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical group COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
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- 235000011037 adipic acid Nutrition 0.000 claims description 2
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- 125000002347 octyl 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])[H] 0.000 claims description 2
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- 230000004044 response Effects 0.000 claims description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 13
- 238000007254 oxidation reaction Methods 0.000 abstract description 13
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 abstract description 7
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 abstract description 7
- 230000006698 induction Effects 0.000 abstract description 4
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- 238000005299 abrasion Methods 0.000 abstract description 2
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- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003026 anti-oxygenic effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
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- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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Abstract
本发明公开了一种中性磷酸酯离子液体,该离子液体通过以下方法制备得到:将中性磷酸酯与双三氟甲烷磺酰亚胺锂(简称LiTFSI)在70 oC~110 oC反应2~4h。该离子液体可用于聚醚(PAG)、合成酯类油等多种合成基础油中,具有优异的抗磨性能,同时具有一定的减摩性能;此外,该离子液体与胺类抗氧剂一同使用时,在合成酯中表现出优异的协同抗氧化作用,能够明显提高起始氧化温度及延长氧化诱导期,是一种高效的抗氧助剂。
Description
技术领域
本发明涉及一种中性磷酸酯离子液体及其应用。
背景技术
近年来离子液体因其具有许多特殊的性质,如高的热稳定性、超低蒸气压、极低的挥发性、很宽的液相范围、不可燃等而受到广泛关注,离子液体的上述性质与理想的高性能润滑剂相吻合,因此是一类极具发展前途的新型润滑剂,并有望作为高性能润滑剂在信息、航空、航天等领域得到实际应用。同时,离子液体所特有的“可设计性”特点,使得我们可以将一个或多个功能团引入到离子液体的阳离子或阴离子上,新官能团的引入将使离子液体展现出不同的物理化学特性,而这些特性可能直接影响离子液体作为润滑剂的摩擦学性能。
原位合成的离子液体因制备工艺简单,不产生三废,原子利用率高而成为一种绿色环保的制备工艺。专利CN 103160363 B就是利用原位合成方法制备的离子液体,并可直接用作润滑剂,具有优异的抗磨减摩性能。
发明内容
本发明的目的在于提供一种中性磷酸酯离子液体及其应用。
本发明所述的离子液体可作为抗磨剂用于聚醚(PAG)或合成酯基础油中,具有优异的抗磨性能,并且具有一定的减摩性能。此外,该离子液体与胺类抗氧剂一同使用时,在合成酯基础油中表现出优异的协同抗氧化作用,能够明显提高起始氧化温度及延长氧化诱导期,是一种高效的抗氧助剂。
一种中性磷酸酯离子液体,其特征在于该离子液体通过以下方法制备得到:将中性磷酸酯与双三氟甲烷磺酰亚胺锂(简称LiTFSI)在70 oC~110 oC反应2~4h。
所述中性磷酸酯与双三氟甲烷磺酰亚胺锂的摩尔比为1:1~1:0.01。
所述中性磷酸酯为磷酸三甲酯、磷酸三乙酯、磷酸三丁酯、磷酸三辛酯、磷酸三甲酚酯中的一种。
所述中性磷酸酯离子液体作为抗磨剂或抗氧助剂的应用。
所述中性磷酸酯离子液体在聚醚或合成酯基础油中作为抗磨剂的应用;所述中性磷酸酯离子液体在合成酯基础油中作为抗氧助剂与胺类抗氧剂一同使用。
所述中性磷酸酯离子液体作为抗磨剂使用时的添加量占聚醚或合成酯基础油的0.1~5wt%,作为抗氧助剂的添加量占合成酯基础油的0.1~3wt%。
所述聚醚为环氧乙烷、环氧丙烷或环氧丁烷的均聚物或共聚物,40℃粘度为15~1500 mm2/s。
所述合成酯基础油为双酯、偏苯三酸酯或多元醇酯中的一种、两种或多种组合物。
所述双酯为己二酸、壬二酸或癸二酸与C 6~C18的脂肪醇反应得到。
所述偏苯三酸酯为偏苯三酸酐与C 6~C18的脂肪醇反应得到。
所述多元醇酯为新戊二醇、三羟甲基丙烷或季戊四醇与C 5~C18的脂肪酸反应得到。
所述胺类抗氧剂为辛基/丁基二苯胺(L57)、二辛基二苯胺(L01)、N-苯基-α-萘胺(T531)、烷基化苯基-α-萘胺(L06)中的一种或两种组合。(括号内为抗氧剂商品代号)。
所述胺类抗氧剂的添加量占合成酯基础油的0.5~3wt%。
本发明具有以下优点:
1、本发明所述中性磷酸酯离子液体的制备工艺简单,成本低廉,并具有优异的抗磨性能,与聚醚、合成酯类油等基础油均具有良好的相溶性,因此,该离子液体具备广泛应用的潜力。
2、本发明所述中性磷酸酯离子液体与胺类抗氧剂共同使用时,具有优异的协同抗氧化作用。
具体实施方式
为了更好的理解本发明,通过以下实施例进行说明:
实施例1:将0.1mol的磷酸三甲酯和0.001mol的LiTFSI加入50mL玻璃样品瓶中,70 oC下搅拌反应2h,得到离子液体A。
实施例2:将0.01mol的磷酸三乙酯和0.003mol的LiTFSI加入10mL玻璃样品瓶中,80 oC下搅拌反应4h,得到离子液体B。
实施例3:将0.01mol的磷酸三丁酯和0.005mol的LiTFSI加入10mL玻璃样品瓶中,90 oC下搅拌反应2h,得到离子液体C。
实施例4:将0.01mol的磷酸三辛酯和0.008mol的LiTFSI加入10mL玻璃样品瓶中,100 oC下搅拌反应3h,得到离子液体D。
实施例5:将0.01mol的的磷酸三甲酚酯和0.01mol的LiTFSI加入10mL玻璃样品瓶中,110 oC搅拌反应4h,得到离子液体E。
为了更好的说明该中性磷酸酯离子液体作为抗磨剂的优势,采用德国 Optimol油脂公司生产的 SRV-IV 微振动摩擦磨损试验机评价了所制备离子液体在聚醚或者季戊四醇酯基础油中的抗磨减摩性能,如表1所示。
表1 离子液体添加剂与中性磷酸酯在不同基础油中抗磨减摩性能对比
SRV测试条件:载荷100N,温度100oC,频率25Hz,振幅1mm,时间30min。
为了更好的说明该中性磷酸酯离子液体具有优异的协同抗氧化作用,以所制备离子液体B、C、D、E分别与一种常用胺型抗氧剂配伍使用,采用高压差示扫描量热法(PDSC)来评价样品的抗氧化性能,测试仪器为德国耐驰公司生产的DSC 204 HP热分析仪。通过程序升温法和恒温法分别测定起始氧化温度和氧化诱导期。①程序升温法是以起始氧化温度作为氧化安定性指标,测试条件:样品用量3.0 ± 0.05mg,升温速率10 oC /min,氮气压力3.5MPa,氧气流速100mL/min,测试温度为室温~350oC。②恒温法是以氧化诱导期作为氧化安定性指标,测试条件:样品用量3.0 ± 0.05mg,以升温速率100oC /min升至测试温度保持恒温,氮气压力3.5MPa,氧气流速100mL/min。测试结果如表2、3、4、5所示。
表2 离子液体B与抗氧剂L57在双酯中的协同抗氧化效果
表3 离子液体C与抗氧剂L57在偏苯三酸酯中的协同抗氧化效果
表4 离子液体D与抗氧剂L01在三羟甲基丙烷酯中的协同抗氧化效果
表5 离子液体E与抗氧剂T531、L06在混合酯中的协同抗氧化效果
综上说明,该中性磷酸酯离子液体与胺类抗氧剂共同使用时起始氧化温度和氧化诱导期均得到明显提升,该中性磷酸酯离子液体具有显著的协同抗氧化性能,可作为一种高效的抗氧助剂使用。
Claims (10)
1.一种中性磷酸酯离子液体,其特征在于该离子液体通过以下方法制备得到:将中性磷酸酯与双三氟甲烷磺酰亚胺锂在70 oC~110 oC反应2~4h。
2.如权利要求1所述的离子液体,其特征在于所述中性磷酸酯与双三氟甲烷磺酰亚胺锂的摩尔比为1:1~1:0.01。
3.如权利要求1或2所述的离子液体,其特征在于所述中性磷酸酯为磷酸三甲酯、磷酸三乙酯、磷酸三丁酯、磷酸三辛酯、磷酸三甲酚酯中的一种。
4.如权利要求1或2所述中性磷酸酯离子液体作为抗磨剂或抗氧助剂的应用。
5.如权利要求4所述的应用,其特征在于所述中性磷酸酯离子液体在聚醚或合成酯基础油中作为抗磨剂的应用;所述中性磷酸酯离子液体在合成酯基础油中作为抗氧助剂与胺类抗氧剂一同使用。
6.如权利要求5所述的应用,其特征在于所述中性磷酸酯离子液体作为抗磨剂使用时的添加量占聚醚或合成酯基础油的0.1~5wt%,作为抗氧助剂的添加量占合成酯基础油的0.1~3wt%。
7.如权利要求5或6所述的应用,其特征在于所述聚醚为环氧乙烷、环氧丙烷或环氧丁烷的均聚物或共聚物,40℃粘度为15~1500mm2/s;所述合成酯基础油为双酯、偏苯三酸酯或多元醇酯中的一种、两种或多种组合物。
8.如权利要求7所述的应用,其特征在于所述双酯为己二酸、壬二酸或癸二酸与C6~C18的脂肪醇反应得到;所述偏苯三酸酯为偏苯三酸酐与C6~C18的脂肪醇反应得到;所述多元醇酯为新戊二醇、三羟甲基丙烷或季戊四醇与C5~C18的脂肪酸反应得到。
9.如权利要求5所述的应用,其特征在于所述胺类抗氧剂为辛基/丁基二苯胺、二辛基二苯胺、N-苯基-α-萘胺、烷基化苯基-α-萘胺中的一种或两种组合。
10.如权利要求5所述的应用,其特征在于所述胺类抗氧剂的添加量占合成酯基础油的0.5~3wt%。
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