CN1329491C - 含膦酸酯官能团的离子液体及其制备方法和用途 - Google Patents
含膦酸酯官能团的离子液体及其制备方法和用途 Download PDFInfo
- Publication number
- CN1329491C CN1329491C CNB2003101177513A CN200310117751A CN1329491C CN 1329491 C CN1329491 C CN 1329491C CN B2003101177513 A CNB2003101177513 A CN B2003101177513A CN 200310117751 A CN200310117751 A CN 200310117751A CN 1329491 C CN1329491 C CN 1329491C
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- Prior art keywords
- ionic liquid
- steel
- functional group
- hexyl
- represent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 25
- -1 imidazole cations Chemical class 0.000 claims abstract description 21
- 229910000831 Steel Inorganic materials 0.000 claims abstract description 20
- 239000010959 steel Substances 0.000 claims abstract description 20
- 239000000314 lubricant Substances 0.000 claims abstract description 10
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000000967 suction filtration Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 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 7
- 239000004411 aluminium Substances 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 2
- 125000001918 phosphonic acid ester group Chemical group 0.000 claims 3
- 238000012360 testing method Methods 0.000 abstract description 5
- 238000004458 analytical method Methods 0.000 abstract description 4
- 238000005461 lubrication Methods 0.000 abstract description 2
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000010702 perfluoropolyether Substances 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 230000009477 glass transition Effects 0.000 abstract 1
- 238000002329 infrared spectrum Methods 0.000 abstract 1
- 238000004611 spectroscopical analysis Methods 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 33
- 239000007788 liquid Substances 0.000 description 31
- 150000003839 salts Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 150000002460 imidazoles Chemical class 0.000 description 7
- 150000003008 phosphonic acid esters Chemical group 0.000 description 7
- 238000010025 steaming Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- DAPXOJOQSNBLKY-UHFFFAOYSA-N 2-hexyl-1h-imidazole Chemical class CCCCCCC1=NC=CN1 DAPXOJOQSNBLKY-UHFFFAOYSA-N 0.000 description 4
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 3
- 229910020808 NaBF Inorganic materials 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- SLLDUURXGMDOCY-UHFFFAOYSA-N 2-butyl-1h-imidazole Chemical compound CCCCC1=NC=CN1 SLLDUURXGMDOCY-UHFFFAOYSA-N 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 229910001423 beryllium ion Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/077—Ionic Liquids
Abstract
Description
Ionic liquid | Kinetic viscosity/mm2·s-1(40℃) | Density/Kg·m-3 | TG/℃ | ΔCp/J/g-1·K-1 |
[DPEBIM][BF4] | 160.2 | 1214.1 | -84.9 | 0.753 |
[DPEHIM][BF4] | 194.4 | 1150.7 | -83.3 | 0.650 |
[DPEOIM][BF4] | 388.8 | 1121.4 | -89.1 | 1.211 |
[DPEBIM][PF6] | 826.3 | 1353.0 | -55.7 | 0.483 |
[DPEHIM][PF6] | 644.5 | 1277.8 | -68.8 | 0.680 |
[DPEOIM][PF6] | 505.9 | 1221.2 | -73.2 | 0.485 |
[DPPBIM][BF4] | 540.1 | 1208.9 | -67.2 | 0.623 |
[DPPHIM][BF4] | 571.9 | 1172.6 | -78.1 | 0.892 |
[DPPOIM][BF4] | 447.3 | 1142.4 | -68.1 | 0.433 |
[DPPBIM][PF6] | 700.7 | 1307.0 | -71.7 | 0.521 |
[DPPHIM][PF6] | 759.7 | 1265.0 | -67.3 | 0.612 |
[DPPOIM][PF6] | 690.9 | 1227.7 | -96.1 | 0.410 |
Load | Friction coefficient | Wear volume/×10-4mm3 | ||||||
/N | DPPOIM][BF4] | DPPHIM][BF4] | X-1P | PFPE | DPPOIM][PF6] | DPPHIM][PF6] | X-1P | PFPE |
100 | 0.062 | 0.066 | 0.091 | 0.135 | 0.06 | 0.11 | 0.14 | 0.12 |
200 | 0.062 | 0.063 | 0.089 | 0.121 | 0.12 | 0.14 | 0.16 | 0.84 |
300 | 0.063 | 0.069 | 0.090 | 0.115 | 0.25 | 0.14 | 1.84 | 2.56 |
400 | 0.065 | 0.075 | - | 0.112 | 0.38 | 0.34 | - | 5.12 |
600 | 0.070 | 0.077 | - | - | 0.56 | 0.78 | - | - |
Load | Friction coefficient | Wear volume/×10-4mm3 | ||||||
/N | DPPOIM][PF6] | DPPHIM][PF6] | LP | X-1P | DPPOIM][PF6] | DPPHIM][PF6] | LP | X-1P |
20 | 0.089 | 0.088 | 0.135 | 0.156 | 0.08 | 0.12 | 1.22 | 4.48 |
40 | 0.084 | 0.078 | 0.117 | 0.127 | 0.19 | 0.22 | 1.92 | 4.00 |
60 | 0.075 | 0.075 | 0.110 | 0.126 | 0.24 | 0.50 | 2.76 | 8.40 |
80 | 0.074 | 0.073 | 0.103 | 0.131 | 0.26 | 0.56 | 3.44 | 15.84 |
100 | 0.070 | 0.070 | 0.100 | 0.129 | 0.62 | 2.92 | 3.60 | 17.04 |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CNB2003101177513A CN1329491C (zh) | 2003-12-30 | 2003-12-30 | 含膦酸酯官能团的离子液体及其制备方法和用途 |
Applications Claiming Priority (1)
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CNB2003101177513A CN1329491C (zh) | 2003-12-30 | 2003-12-30 | 含膦酸酯官能团的离子液体及其制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
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CN1635063A CN1635063A (zh) | 2005-07-06 |
CN1329491C true CN1329491C (zh) | 2007-08-01 |
Family
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CNB2003101177513A Expired - Fee Related CN1329491C (zh) | 2003-12-30 | 2003-12-30 | 含膦酸酯官能团的离子液体及其制备方法和用途 |
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Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103374034B (zh) * | 2012-04-24 | 2016-01-06 | 宁波大学 | 一种有机膦功能化的吡啶类离子液体及其制备方法 |
CN103374035B (zh) * | 2012-04-24 | 2016-01-06 | 宁波大学 | 一种微波合成有机膦功能化咪唑类离子液体的方法 |
CN102776053B (zh) * | 2012-08-03 | 2013-12-18 | 山东源根石油化工有限公司 | 复合极压抗磨剂及含有该复合极压抗磨剂的全合成抗磨液压油 |
CN105254667B (zh) * | 2015-11-17 | 2017-06-23 | 中国科学院兰州化学物理研究所 | 功能化油溶性离子液体及其制备方法和应用 |
JP7012660B2 (ja) | 2016-04-01 | 2022-02-14 | ノームズ テクノロジーズ インコーポレイテッド | リン含有修飾イオン性液体 |
CN105887102A (zh) * | 2016-04-25 | 2016-08-24 | 中国科学院兰州化学物理研究所 | 磷酸酯功能化的季铵盐缓蚀剂及其制备方法 |
EP4106070A1 (en) | 2017-07-17 | 2022-12-21 | Nohms Technologies, Inc. | Phosphorus-containing electrolytes |
CN111644163B (zh) * | 2020-06-22 | 2023-04-07 | 宁波大学 | 一种用于富集磷酸化多肽的三足离子液体材料及其制备方法及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5550276A (en) * | 1990-01-18 | 1996-08-27 | Ciba-Geigy Corporation | Phosphonic acid derivatives and thionophosphonic acid derivatives |
CN1190427A (zh) * | 1995-05-18 | 1998-08-12 | 卡斯特罗尔有限公司 | 润滑组合物 |
CN1405140A (zh) * | 2002-11-07 | 2003-03-26 | 华东师范大学 | 离子液体[Hmim] +BF4-中酯化的方法 |
-
2003
- 2003-12-30 CN CNB2003101177513A patent/CN1329491C/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5550276A (en) * | 1990-01-18 | 1996-08-27 | Ciba-Geigy Corporation | Phosphonic acid derivatives and thionophosphonic acid derivatives |
CN1190427A (zh) * | 1995-05-18 | 1998-08-12 | 卡斯特罗尔有限公司 | 润滑组合物 |
CN1405140A (zh) * | 2002-11-07 | 2003-03-26 | 华东师范大学 | 离子液体[Hmim] +BF4-中酯化的方法 |
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CN1635063A (zh) | 2005-07-06 |
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