CN106632456B - 甘露醇脂肪酸磷酸酯及其制备方法和用酯制备环保微量润滑油 - Google Patents
甘露醇脂肪酸磷酸酯及其制备方法和用酯制备环保微量润滑油 Download PDFInfo
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- CN106632456B CN106632456B CN201611184909.2A CN201611184909A CN106632456B CN 106632456 B CN106632456 B CN 106632456B CN 201611184909 A CN201611184909 A CN 201611184909A CN 106632456 B CN106632456 B CN 106632456B
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- acid
- lubricating oil
- environmentally friendly
- micro lubricating
- fatty acid
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- 239000010687 lubricating oil Substances 0.000 title claims abstract description 36
- 229920005862 polyol Polymers 0.000 title claims abstract description 29
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 28
- 239000000194 fatty acid Substances 0.000 title claims abstract description 28
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 28
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 28
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 26
- 239000010452 phosphate Substances 0.000 title claims abstract description 26
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 26
- 235000009508 confectionery Nutrition 0.000 title claims abstract description 22
- 150000003077 polyols Chemical class 0.000 title claims abstract description 22
- 150000002148 esters Chemical class 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 32
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims abstract description 31
- 229930195725 Mannitol Natural products 0.000 claims abstract description 31
- 239000000594 mannitol Substances 0.000 claims abstract description 31
- 235000010355 mannitol Nutrition 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 22
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 16
- 230000007613 environmental effect Effects 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- -1 Polyol ester Chemical class 0.000 claims description 11
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 9
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 claims description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 claims description 6
- DIOYAVUHUXAUPX-KHPPLWFESA-N Oleoyl sarcosine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CC(O)=O DIOYAVUHUXAUPX-KHPPLWFESA-N 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- GSAHAZJWNMHSNI-UHFFFAOYSA-N 2,2-bis(dodecanoyloxymethyl)butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC GSAHAZJWNMHSNI-UHFFFAOYSA-N 0.000 claims description 4
- HJVAFZMYQQSPHF-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;boric acid Chemical compound OB(O)O.OCCN(CCO)CCO HJVAFZMYQQSPHF-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 4
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 4
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- 229940049964 oleate Drugs 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 4
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 claims description 4
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- HRXOXDAKKRLSMI-UHFFFAOYSA-N boric acid;2-(2-hydroxyethylamino)ethanol Chemical compound OB(O)O.OCCNCCO HRXOXDAKKRLSMI-UHFFFAOYSA-N 0.000 claims description 3
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims description 3
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 3
- 229940093471 ethyl oleate Drugs 0.000 claims description 3
- 229940067592 ethyl palmitate Drugs 0.000 claims description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 3
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N lauric acid triglyceride Natural products CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims description 3
- 229940073769 methyl oleate Drugs 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 3
- VPUPTBGJLAVERZ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol hexadecanoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCC(O)=O VPUPTBGJLAVERZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims description 2
- 108010077895 Sarcosine Proteins 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 229940043230 sarcosine Drugs 0.000 claims description 2
- 125000005480 straight-chain fatty acid group Chemical group 0.000 claims description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 2
- 229960001947 tripalmitin Drugs 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- HFWHTGSLDKKCMD-UHFFFAOYSA-N 2,2-bis(octanoyloxymethyl)butyl octanoate Chemical compound CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC HFWHTGSLDKKCMD-UHFFFAOYSA-N 0.000 claims 1
- BVUBQTCRHMSAOI-UHFFFAOYSA-N C(CCCCCCCC=C/CCCCCCCC)(=O)O.C(CCCCCCCC=C/CCCCCCCC)(=O)O.C(CCCCCCCC=C/CCCCCCCC)(=O)O.CCC Chemical compound C(CCCCCCCC=C/CCCCCCCC)(=O)O.C(CCCCCCCC=C/CCCCCCCC)(=O)O.C(CCCCCCCC=C/CCCCCCCC)(=O)O.CCC BVUBQTCRHMSAOI-UHFFFAOYSA-N 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims 1
- 229940070765 laurate Drugs 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 229960002969 oleic acid Drugs 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 238000005461 lubrication Methods 0.000 abstract description 14
- 239000000314 lubricant Substances 0.000 abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000460 chlorine Substances 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005864 Sulphur Substances 0.000 abstract description 2
- 239000007866 anti-wear additive Substances 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000002131 composite material Substances 0.000 abstract description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 4
- JCAYXDKNUSEQRT-UHFFFAOYSA-N 2-aminoethoxyboronic acid Chemical compound NCCOB(O)O JCAYXDKNUSEQRT-UHFFFAOYSA-N 0.000 description 3
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002173 cutting fluid Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- MLINROWIZAPJDA-UHFFFAOYSA-N P(=O)(O)(O)O.C(CCCCCCCCCCCCC)(=O)O Chemical compound P(=O)(O)(O)O.C(CCCCCCCCCCCCC)(=O)O MLINROWIZAPJDA-UHFFFAOYSA-N 0.000 description 2
- CWNAUYSVLRNOQM-UHFFFAOYSA-N dodecanoic acid;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCCCC(O)=O CWNAUYSVLRNOQM-UHFFFAOYSA-N 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 2
- YVPOTNAPPSUMJX-UHFFFAOYSA-N octadecanoic acid;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCCCCCCCCCC(O)=O YVPOTNAPPSUMJX-UHFFFAOYSA-N 0.000 description 2
- VHHMNNRGNQWMKU-KTKRTIGZSA-N phosphono (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OP(O)(O)=O VHHMNNRGNQWMKU-KTKRTIGZSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- MSYJMGQEHMRJNS-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCC)(=O)O.CCC Chemical compound C(CCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCC)(=O)O.CCC MSYJMGQEHMRJNS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- BJXXCOMGRRCAGN-CLFAGFIQSA-N [2,2-bis(hydroxymethyl)-3-[(z)-octadec-9-enoyl]oxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCC\C=C/CCCCCCCC BJXXCOMGRRCAGN-CLFAGFIQSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000002190 fatty acyls Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- 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
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- C—CHEMISTRY; METALLURGY
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Abstract
本发明提供的一种甘露醇脂肪酸磷酸酯,其特征在于:由包括以下组分的物质制备而成:甘露醇、脂肪酸、磷酸;其中,所述甘露醇与脂肪酸的摩尔比为1:3‑6;所述磷酸有效成分占甘露醇与脂肪酸总重量的百分比为2‑3%。采用本发明方法制备的甘露醇脂肪酸磷酸酯,基于其具有优异的润滑性、极压抗磨性,可全部或部分取代传统的含氯、硫、磷的极压抗磨剂,使用于微量润滑油中,少量的微量润滑油就能满足金属加工的润滑冷却、极压抗磨要求,配合微量润滑装置使用,可节省润滑剂的使用量95%以上,节能减排、环境保护效果显著。
Description
技术领域
本发明属于润滑技术领域,涉及一种甘露醇脂肪酸磷酸酯及其制备方法和用酯制备环保微量润滑油。
背景技术
传统的金属切削加工采用矿物油或植物油或切削液进行大量冲淋式润滑,润滑剂的使用量大,不仅浪费资源,造成加工场所和环境的巨大污染,同时还会严重影响操作工人的身体健康。
为解决这些问题,近期对微量润滑技术的研究取得一定的进展,微量润滑技术解决了以上润滑剂使用量大,污染严重等问题,但对微量润滑剂的研究,但在应用方面还存在一定的问题,主要是润滑和冷却问题不能很好的解决。
此外,微量润滑剂往往需要添加大量的含硫、含氯等对环境有较大压力的添加剂来增加产品的极压抗磨性,延长刀具使用寿命。
另外,由于追求使用的润滑剂使用量微少,所以组成原料往往不能降解,也会加重环境的负担。
发明内容
鉴于以上缺陷,本发明的目的是克服现有技术的不足,提供甘露醇脂肪酸磷酸酯及其制备方法和用酯制备环保微量润滑油。
为实现上述目的,本发明提供的甘露醇脂肪酸磷酸酯,其特征在于,由包括以下组分的物质制备而成:甘露醇、脂肪酸、磷酸;
其中,上述甘露醇与脂肪酸的摩尔比为1:3-6。
上述磷酸有效成分占甘露醇与脂肪酸总重量的百分比为2-3%。
上述的脂肪酸选自碳原子数为10-20的饱和或不饱和脂肪酸中的一种或几种,优选自:正癸酸、月桂酸、棕榈酸、肉豆蔻酸、亚油酸、油酸、硬脂酸中的一种或几种。
此外,本发明还提供了上述甘露醇脂肪酸磷酸酯的制造方法:由甘露醇、脂肪酸、磷酸进行酯化反应制备而成的。
上述甘露醇脂肪酸磷酸酯的制备方法如下:
将甘露醇、脂肪酸、磷酸加入反应釜内,充入保护气(如:氮气、氩气等)转换出反应釜内空气,于180~220℃的反应温度下反应6-8小时;反应后减压排出水分,即为甘露醇脂肪酸磷酸酯。
此外,本发明还提供了一种环保微量润滑油,其特征在于:制造环保微量润滑剂的原料中包含有由上述方法制备的甘露醇脂肪酸磷酸酯,且该甘露醇脂肪酸磷酸酯的用量为原料总质量的10-40%。
本发明提供了一种环保微量润滑油的优选方案,由以下重量百分比含量的组分制造面成:
甘露醇脂肪酸磷酸酯 10-40%;
多元醇酯 60-90%。
另外,本发明还提供了一种环保微量润滑油的优选方案,由以下重量百分比含量的组分制造而成:
上述多元醇酯选自由多元醇与一元脂肪酸进行酯化反应人工合成所得的合成酯中的一种或多种,该多元醇选自碳原子数为10-50的多元醇及其衍生物,该一元脂肪酸选自碳原子数为2-20的一元脂肪酸及其衍生物,优选自:三异辛酸甘油酯、三羟甲基丙烷三异辛酸酯、季戊四醇四异辛酸酯,三月桂酸甘油酯、三羟甲基丙烷三月桂酸酯、季戊四醇四月桂酸酯、三油酸甘油酯、三羟甲基丙烷三油酸酯、季戊四醇四油酸酯、三棕榈酸甘油酯、三羟甲基丙烷三棕榈酸酯、季戊四醇四棕榈酸酯中的一种或多种。该多元醇酯是一种良好的生物可降解润滑剂,其润滑性能良好。
上述单酯选自由一元醇和一元脂肪酸制备的酯中的一种或几种,该一元醇优选为碳原子数不超过25的一元醇及其衍生物,该一元脂肪酸优选为碳原子数不超过25的饱和或不饱和的一元脂肪酸及其衍生物;
上述单酯还可选自由天然油脂衍生的直链脂肪酸和一元低碳醇酯化反应得到的酯中的一种或几种,优选自:油酸甲酯、月桂酸甲酯、月桂酸乙酯、硬脂酸甲酯、硬脂酸乙酯、棕榈酸甲酯、棕榈酸乙酯、油酸乙酯、油酸丁酯中的一种或几种。此类单酯应用于本配方中,可未做良好的生物可降解润滑剂,其不但润滑性能良好,还同时具有较低的运动粘度。
上述异构醇选自碳原子数为10-20的异构醇中的一种或几种混合物。优选选自碳原子数为12-16的异构醇。异构醇的润滑性好,在加工金属表面的扩散性性好,挥发性好。
上述酰基肌氨酸可选自月桂酰肌氨酸、肉豆蔻酰肌氨酸、油酰肌氨酸中的一种或几种的混合物。是良好的可生物降解防锈剂,同时有较好的润滑性能。
上述的醇胺硼酸酯为一乙醇胺硼酸酯、二乙醇胺硼酸酯、三乙醇胺硼酸酯中的一种或几种的混合物,有良好的极压抗磨性和防锈性。
本发明还提供了上述环保微量润滑油的制备方法,其特征在于:将各组分的物质(如:露醇脂肪酸磷酸酯、多元醇酯、单酯、异构醇、脂肪酰肌氨酸、醇胺硼酸酯)置于搅拌器中在40-60℃下搅拌至完全透明,即为一种环保微量润滑油。
发明的作用与效果:
采用本发明方法制备的甘露醇脂肪酸磷酸酯,基于其具有优异的润滑性、极压抗磨性,可全部或部分取代传统的含氯、硫、磷的极压抗磨剂,使用于微量润滑油中,少量的微量润滑油就能满足金属加工的润滑冷却、极压抗磨要求,配合微量润滑装置使用,可节省润滑剂的使用量95%以上,节能减排、环境保护效果显著。
具体实施方式
实施例一
称取甘露醇18217g(100mol)、103356g(600mol)正癸酸、3800g磷酸(有效成分85%)加入反应釜内,充入氮气转换出反应釜内空气,于220℃的反应温度下反应8小时;反应后减压排出水分,即为甘露醇正癸酸磷酸酯。
取上述制备的甘露醇正癸酸磷酸酯4000g,季戊四醇四棕榈酸酯6000kg置于搅拌器中搅拌至完全透明,即为一种环保微量润滑油。
实施例二
称取甘露醇18217g(100mol)、60096g(300mol)月桂酸、3200g磷酸(浓度50%)加入反应釜内,充入氮气转换出反应釜内空气,于180℃的反应温度下反应6小时;反应后减压排出水分,即为甘露醇月桂酸磷酸酯。
取上述甘露醇月桂酸磷酸酯300g、三羟甲基丙烷三月桂酸酯200g、油酸丁酯150g、异构十三醇150g、月桂酰肌氨酸100g、一乙醇胺硼酸酯100g置于搅拌器中在40℃下搅拌至完全透明,即为一种环保微量润滑油。
实施例三
称取甘露醇18217g(100mol)、91348g(400mol)肉豆蔻酸、5500g磷酸(浓度50%)加入反应釜内,充入氮气转换出反应釜内空气,于200℃的反应温度下反应7小时;反应后减压排出水分,即为甘露醇肉豆蔻酸磷酸酯。
取上述甘露醇肉豆蔻酸磷酸酯250g、三月桂酸甘油酯300g、油酸甲酯200g、异构二十醇100g、肉豆蔻酰肌氨酸80g、二乙醇胺硼酸酯70g置于搅拌器中在50±1℃下搅拌至完全透明,即为一种环保微量润滑油。
实施例四
称取甘露醇18217g(100mol)、140220g(500mol)亚油酸、8000g磷酸(浓度50%)加入反应釜内,充入氮气转换出反应釜内空气,于210℃的反应温度下反应6.5小时;反应后减压排出水分,即为甘露醇亚油酸磷酸酯。
取上述甘露醇亚油酸磷酸酯250g、三羟甲基丙烷三月桂酸酯280g、月桂酸甲酯50g、棕榈酸甲酯90g、异构十六醇140g、油酰肌氨酸90g、一乙醇胺硼酸酯50g、三乙醇胺硼酸酯50g置于搅拌器中在50℃左右下搅拌至完全透明,即为一种环保微量润滑油。
实施例五
称取甘露醇18217g(100mol)、113792g(400mol)硬脂酸、6500g磷酸(浓度50%)加入反应釜内,充入氮气转换出反应釜内空气,于205℃的反应温度下反应7小时;反应后减压排出水分,即为甘露醇硬脂酸磷酸酯。
取上述甘露醇硬脂酸磷酸酯280g、三羟甲基丙烷三棕榈酸酯190g、三羟甲基丙烷三异辛酸酯100g、棕榈酸甲酯100g、棕榈酸乙酯60g、异构十三/四醇170g、月桂酰肌氨酸30g、油酰肌氨酸20g、三乙醇胺硼酸酯50g置于搅拌器中在50℃下搅拌至完全透明,即为一种环保微量润滑油。
实施例六
称取甘露醇18217g(100mol)、141235g(500mol)油酸、8000g磷酸(浓度50%)加入反应釜内,充入氮气转换出反应釜内空气,于200℃的反应温度下反应7小时;反应后减压排出水分,即为甘露醇油酸磷酸酯。
取上述甘露醇油酸磷酸酯280g、三羟甲基丙烷三油酸酯260g、油酸乙酯160g、异构十四/五醇140g、油酰肌氨酸80g、三乙醇胺硼酸酯80g置于搅拌器中在50±1℃下搅拌至完全透明,即为一种环保微量润滑油。
将上述实施例六制备的环保微量润滑油应用于铝合金高速铣削加工,加工中心型号:CMV-510AII;加工工件规格:250*200*25mm。原来用切削液进行循环润滑冷却,现在改为KS-2107微量润滑装置(3喷嘴,所用喷嘴为本公司生产节能喷嘴)和一种环保微量润滑油,结果如下表:
将上述实施例六制备的环保微量润滑剂应用于铝合金零件数控车床加工,车床型号:CJK-0620。原来用乳化液进行循环润滑冷却,现在改为KS-2106微量润滑装置(U型喷嘴,2个出液/气孔)和环保微量润滑油,结果如下表:
项目 | 传统润滑方式 | 微量润滑方式 |
加工一组零件所需时间 | 10分钟 | 10分钟 |
润滑剂消耗 | 10kg/天 | 0.15kg/天 |
工作现场 | 切削液到处流,现场脏乱 | 十分干净 |
Claims (16)
1.一种甘露醇脂肪酸磷酸酯,其特征在于:由包括以下组分的物质制备而成:甘露醇、脂肪酸、磷酸;
其中,所述甘露醇与脂肪酸的摩尔比为1:3-6;
所述磷酸有效成分占甘露醇与脂肪酸总重量的百分比为2-3%;
所述甘露醇脂肪酸磷酸酯的制造方法:由甘露醇、脂肪酸、磷酸进行酯化反应制备而成;
具体工艺步骤如下所示:
将甘露醇、脂肪酸、磷酸加入反应釜内,充入保护气转换出反应釜内空气,于180~220℃的反应温度下反应6-8小时;反应后减压排出水分,即为甘露醇脂肪酸磷酸酯。
2.如权利要求1所述的一种甘露醇脂肪酸磷酸酯,其特征在于:
所述脂肪酸选自碳原子数为10-20的饱和或不饱和脂肪酸中的一种或几种。
3.如权利要求1所述的一种甘露醇脂肪酸磷酸酯,其特征在于:
所述脂肪酸选自正癸酸、月桂酸、棕榈酸、肉豆蔻酸、亚油酸、油酸、硬脂酸中的一种或几种。
4.一种环保微量润滑油,其特征在于:
由包含有如权利要求1-3任一所述的甘露醇脂肪酸磷酸酯的原料制造而成;
其中,所述甘露醇脂肪酸磷酸酯的占原料总质量的10-40%。
5.如权利要求4所述的一种环保微量润滑油,其特征在于,由以下重量百分比含量的组分制造而成:
甘露醇脂肪酸磷酸酯 10-40%;
多元醇酯 60-90%。
6.如权利要求4所述的一种环保微量润滑油,其特征在于,由以下重量百分比含量的组分制造而成:
7.如权利要求5或6所述的一种环保微量润滑油,其特征在于:
所述多元醇酯选自由多元醇与一元脂肪酸进行酯化反应后获得的合成酯中的一种或几种。
8.如权利要求5或6所述的一种环保微量润滑油,其特征在于:
所述多元醇酯选自三异辛酸甘油酯、三羟甲基丙烷三异辛酸酯、季戊四醇四异辛酸酯,三月桂酸甘油酯、三羟甲基丙烷三月桂酸酯、季戊四醇四月桂酸酯、三油酸甘油酯、三羟甲基丙烷三油酸酯、季戊四醇四油酸酯、三棕榈酸甘油酯、三羟甲基丙烷三棕榈酸酯、季戊四醇四棕榈酸酯中的一种或几种。
9.如权利要求6所述的一种环保微量润滑油,其特征在于:
所述单酯选自由一元醇和一元脂肪酸制备而成的酯中的一种或几种。
10.如权利要求6所述的一种环保微量润滑油,其特征在于:所述单酯选自由天然油脂衍生的直链脂肪酸和一元低碳醇酯化反应得到的酯中的一种或几种。
11.如权利要求6所述的一种环保微量润滑油,其特征在于:所述单酯选自油酸甲酯、月桂酸甲酯、月桂酸乙酯、硬脂酸甲酯、硬脂酸乙酯、棕榈酸甲酯、棕榈酸乙酯、油酸乙酯、油酸丁酯中的一种或几种。
12.如权利要求6所述的一种环保微量润滑油,其特征在于:所述异构醇-选自碳原子数为10-20的异构醇中的一种或几种。
13.如权利要求6所述的一种环保微量润滑油,其特征在于:所述异构醇-选自碳原子数为12-16的异构醇中的一种或几种。
14.如权利要求6所述的一种环保微量润滑油,其特征在于:所述酰基肌氨酸选自月桂酰肌氨酸、肉豆蔻酰肌氨酸、油酰肌氨酸中的一种或几种。
15.如权利要求6所述的一种环保微量润滑油,其特征在于:所述醇胺硼酸酯选自一乙醇胺硼酸酯、二乙醇胺硼酸酯、三乙醇胺硼酸酯中的一种或几种。
16.如权利要求4-15任一所述的一种环保微量润滑油的制备方法,其特征在于:将各组分置于搅拌器中在40-60℃下搅拌至完全透明,即为一种环保微量润滑油。
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