CN115895752A - 一种抗磨添加剂、其制备方法及在油品中的应用 - Google Patents
一种抗磨添加剂、其制备方法及在油品中的应用 Download PDFInfo
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- CN115895752A CN115895752A CN202111155603.5A CN202111155603A CN115895752A CN 115895752 A CN115895752 A CN 115895752A CN 202111155603 A CN202111155603 A CN 202111155603A CN 115895752 A CN115895752 A CN 115895752A
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- acid
- epoxy
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- anhydride
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- RGDDVTHQUAQTIE-UHFFFAOYSA-N 2-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC=C1O RGDDVTHQUAQTIE-UHFFFAOYSA-N 0.000 description 1
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- UVTIZRNEWKAOEM-UHFFFAOYSA-N 2-tert-butylperoxy-2-methylbutane Chemical compound CCC(C)(C)OOC(C)(C)C UVTIZRNEWKAOEM-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000006061 abrasive grain Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 1
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- VZSXFJPZOCRDPW-UHFFFAOYSA-N carbanide;trioxorhenium Chemical compound [CH3-].O=[Re](=O)=O VZSXFJPZOCRDPW-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
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- 239000003245 coal Substances 0.000 description 1
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- 150000004696 coordination complex Chemical class 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- AZXVZUBIFYQWJK-KWRJMZDGSA-N ethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC AZXVZUBIFYQWJK-KWRJMZDGSA-N 0.000 description 1
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- XJNUECKWDBNFJV-UHFFFAOYSA-N hexadecyl 2-ethylhexanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(CC)CCCC XJNUECKWDBNFJV-UHFFFAOYSA-N 0.000 description 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
- 239000002006 petroleum coke Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003658 tungsten compounds Chemical class 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
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Abstract
Description
技术领域
本发明涉及油品添加剂领域,具体地,涉及一种改善油品润滑性能的添加剂以及含有该添加剂的油品组合物。
背景技术
为了满足环保要求,低硫或者超低硫化柴油已经成为世界各国追寻的目标。随着加氢精炼工艺技术的不断提高,生产低硫柴油的同时也会将其他具有润滑性的组分一起脱除,比如含氧含氮化合物及多环芳烃化合物。柴油润滑性能变差,在柴油发动机工作时会导致磨损,难以保证发动机正常运行。为了改善柴油的润滑性能,在低硫柴油中加入具有润滑性能的抗磨剂是目前最简单有效且经济的方法。
CN109576063A公开了一种低硫柴油抗磨剂及制备方法,是将马来酸酐的酯化产物、具有非共轭双键的植物油脂肪酸、催化剂按比例混合,在180~220℃、搅拌条件下反应一定时间,反应结束后降温,回收催化剂,经减压蒸馏后得到抗磨剂产品。该工艺制备的抗磨剂产品虽然表现良好的抗磨性能,但是原料来源比较受限,因此导致抗磨剂产品的生产成本大大增加,而不利于工业化生产。另一方面,所制备的抗磨剂产品氧化安定性差,难以保持稳定的抗磨效果,不利于抗磨剂产品的储存,且对产品的储存要求较高。
CN103540369B公开了一种低硫柴油抗磨剂组合物,按质量分数计,由以下成分组成:甘油硬脂酸酯30-50份、异鲸蜡醇棕榈酸酯10-20份、鲸蜡醇乙基己酸酯10-20份、羊毛脂醇聚醚-2510-20份。虽然提供的抗磨剂产品能够改善低硫柴油的润滑性能,但是原料来源受限,导致抗磨剂产品的制备成本高昂。
CN101768480B公开了一种柴油抗磨剂,是由原料(A)至少一种酰胺类组分,(B)至少一种胺类油性剂组分,(C)至少一种酯类油性剂组分,(D)至少一种防锈剂,(E)至少一种破乳剂,(F)至少一种有机溶剂组成,虽然所述的抗磨剂产品能够改善低硫柴油的润滑性能,但是该抗磨剂产品中含有胺、酰胺类化合物等含氮组分物质,加入柴油中会导致氮氧化物的生成,不符合绿色化学的理念。
CN109929624B公开了一种脂肪酸类柴油抗磨剂及配方,具体是由80重量份脂肪酸类柴油抗磨剂与20重量份的有机氮钼富勒烯润滑剂组成。然而,一方面该抗磨剂产品改善低硫柴油的润滑性的效果一般,另一方面由于该添加剂的组成物之一是有机氮钼富勒烯,极大的提高了抗磨剂产品的制备成本,工业化前景较小。
EP1404726A2公开了一种聚合物型抗磨剂,可用于改善低硫柴油的润滑性能,该添加剂是由数均分子量为300~1000的聚异丁烯基琥珀酸酐类衍生物或由数均分子量为2000~20000的聚异丁烯基琥珀酸酐类衍生物构成。但是聚合反应条件较为苛刻,对生产设备的要求较高。此外,聚合反应不易控制,若聚合物分子量过高则难以与柴油互溶,难以表现良好的抗磨性能。
发明内容
本发明提供一种具有改善油品润滑性能的抗磨剂产品,该抗磨剂产品能够在燃料油品、润滑油品中表现良好的抗磨性能,并且具有良好的稳定性。
本发明也提供该抗磨剂的制备方法。
本发明还提供含有该抗磨剂的油品组合物。同时,本发明提供了该抗磨剂产品在油品中的应用方法。
为了实现上述目的,本发明提供的一种用于改善油品润滑性能的抗磨添加剂,所述添加剂为具有结构式1所示的化合物:
其中,R1、R2为单键或C1~C20的烃基,R3、R4各自独立为氢或C1~C10的烃基,X、Y基团各自独立为氢或C1~C50的烃基、含氧官能团或含氮官能团。
其中,所述烃基可以是饱和烃基或不饱和烃基,例如正构烷烃、异构烷烃、环烷烃、芳烃、正构烯烃、异构烯烃、环烯烃等。
优选地,R1、R2为单键或C1~C10的烷烃或烯烃,R3、R4为氢或C1~C5的烷烃或烯烃;X基团、Y基团为氢或C4~30的烷烃、烯烃、含氧官能团或含氮官能团。
进一步优选地,R1、R2为单键或C1~C4的烷烃或烯烃,R3、R4为氢或C1~C2的烷烃或烯烃;X基团、Y基团为氢或C4~C20的正烷烃、烯烃、含氧官能团、含氮官能团。
最优选地,R1、R2为单键,R3、R4为氢或C1~C2的正构烷烃。
当R1、R2为单键,R3、R4为氢时,所述抗磨剂为结构式2所示的化合物结构:
结构式2中,进一步优选X基团为氢,Y基团为C4~C20的正构烷烃、正构烯烃、异构烷烃、异构烯烃、含氧官能团、含氮官能团。
结构式2中,当Y基团为正构烷烃或异构烷烃时,具体可以包括但不限于正丁基、异丁基、正戊基、异戊基、正己基、异己基、正庚基、异庚基、正辛基、异辛基、正壬基、异壬基、正癸基、异癸基、正十二烷基、异十二烷基、正十四烷基、异构十四烷基、正十六烷基、异构十六烷基、正十八烷基、异构十八烷基、正构二十烷基、异构二十烷基等;当Y基团为正构烯基或异构烯基时,包括但不限于正丁烯基、异丁烯基、正戊烯基、异戊烯基、正烯己基、异己烯基、正庚烯基、异庚烯基、正辛烯基、异辛烯基、正壬烯基、异壬烯基、正癸烯基、异癸烯基、正十二烯基、异十二烯基、正十四烯基、异构十四烯基、正十六烯基、异构十六烯基、正十八烯基、异构十八烷烯、正构二十烯基、异构二十烷烯等;当Y基团为环烷烃时,包括但不限于环戊烷、环己烷、甲基环烷基、甲基环己烷等;当Y基团为环烯烃时,包括但不限于环戊烯、环己烯、甲基环戊烯、甲基环己烯等;当Y基团为含氧官能团时,包括但不限于羟基(-OH)、羧基(-COOH)、酯基(-COOR)、醚基(R-O-R)以及羟基(-OH),具体结构可以包括但不限于:-C8H16OH、-C8H16COOH、-C8H16COOCH=CH2、-C2H4OC7H14CH3、-C17H34COOCH3、-C17H34COOH、-C17H32COOH、-C17H32COOCH3等。
当Y基团为含氮官能团时,包括但不限于氨基(-HNx)、酰胺基(-NOH)等。包括但不限于:-C8H16NH2、-C2H4NHOC8H16、-(C2H4)2NOC8H16等。
具体地,所述结构式1的化合物可以包括但不限于以下化合物:环氧琥珀酸单正丁酯、环氧琥珀酸单异丁酯、环氧琥珀酸单正戊酯、环氧琥珀酸单异戊酯、环氧琥珀酸单正辛酯、环氧琥珀酸单异辛酯、环氧琥珀酸单正壬酯、环氧琥珀酸单异壬酯、环氧琥珀酸单月桂酯、环氧琥珀酸单十八醇酯、环氧琥珀酸单油醇酯等;环氧琥珀酸单环戊醇酯、环氧琥珀酸单环己醇酯、环氧琥珀酸单聚聚乙二醇单甲醚基酯、环氧琥珀酸单聚乙二醇酯、环氧琥珀酸聚丙二醇酯、环氧琥珀酸聚丙二醇单丁醚酯、环氧琥珀酸单蓖麻油酸基酯、环氧琥珀酸单蓖麻油酸甲酯基酯、12-羟基硬脂酸基环氧琥珀酸单酯、12-羟基硬脂酸甲酯基环氧琥珀酸单酯等。
本发明提供两种所述抗磨剂的制备方法,第一种制备方法包括以下步骤:
(1)由不饱和二元酸或酸酐与含羟基的化合物进行半酯化反应,获得反应中间体;
(2)再将反应中间体与过氧化物在催化剂存在下进行环氧化反应,得到产品。
其中,步骤(1)中,半酯化反应温度为20~200℃,优选50~150℃,最优选75~120℃;反应时间为0.5~20小时,优选1~10小时,最优选1~4小时;其不饱和二元酸或酸酐与含羟基的化合物的摩尔比为1:0.1~5,优选1:0.5~3,最优选1:1~2。
步骤(2)中,反应中间体与过氧化物的摩尔比为1:0.1~10,优选1:0.5~5,最优选1:1~3;反应时间为0.5~20小时,优选1~10小时;反应温度为0~180℃,进一步优选20~150℃,最优选30~100℃。
第二种制备方法包括以下步骤:
(1)由不饱和二元酸或酸酐与过氧化物在催化剂存在下进行环氧化反应,获得反应中间体;
(2)再将反应中间体与含羟基的化合物进行半酯化反应,得到产品。
其中,步骤(1)中,环氧化反应的温度为0℃~180℃,优选20℃~150℃,最优选30℃~100℃。环氧化反应时间为0.5h~30h,优选1h~20h,最优选6h~10h。所述不饱和二元酸或酸酐与过氧化物的摩尔比为1:0.1~10,优选1:0.5~5,最优选1:1~3。
步骤(2)中,所述的半酯化反应温度为20~200℃,优选50~150℃,最优选75~120℃;其反应时间为0.5h~20h,优选1h~10h,最优选1h~4h;环氧化物中间体与含羟基的化合物的摩尔比为1:0.1~5,优选1:0.5~3,最优选1:1~2。
根据本发明的两种制备方法,所述的不饱和二元酸或酸酐包括但不限于:顺丁烯二酸、反丁烯二酸、顺丁烯二酸酐(马来酸酐)、反丁烯二酸酐(富马酸酐)、2,3-二甲基马来酸、2,3-二甲基马来酸酐、2-甲基马来酸、2-甲基马来酸酐、戊烯二酸、戊烯二酸酐、3-甲基戊烯二酸、癸烯二酸、癸烯二酸酐、己二烯二酸、十二碳烯二酸、十八碳烯二酸、二十碳烯二酸等。
根据本发明的两种制备方法,所述羟基化合物可以选自C1~C50,优选C4~C30,进一步优选C4~C20的脂肪醇、羟基脂肪酸、羟基脂肪酸酯、羟基脂肪胺、羟基酰胺、醚醇、酚类化合物。其中,所述脂肪醇包括但不限于正丁醇、异丁醇、正戊醇、异戊醇、正辛醇、异辛醇、正壬醇、异壬醇、月桂醇、十四醇、十八醇、油醇、二十醇、戊烯醇、己烯醇、聚乙二醇、聚丙二醇、环己醇、环戊醇、环己烯醇、环戊烯醇等;所述羟基脂肪酸包括但不限于蓖麻油酸、12-羟基硬脂酸等;所述的羟基脂肪酸酯包括但不限于12-羟基硬脂酸甲酯、蓖麻油酸甲酯、蓖麻油酸乙酯、蓖麻油酸丁酯,以及含有蓖麻油酸甲酯成分的生物柴油等;所述羟基脂肪胺包括但不限于N-甲基二辛醇胺、辛醇胺;所述羟基酰胺优选辛烷基羟基乙酰胺;所述醚醇包括但不限于聚乙二醇单甲醚、聚丙二醇单丁醚等;所述酚类化合物包括但不限于戊基酚、庚基酚、辛基酚、壬基酚、癸基酚、十二烷基酚、十五烷基苯酚、烷基酚聚氧乙烯醚等。
根据本发明的两种制备方法,所述的过氧化物包括但不限于过氧化氢,过氧酸,烷基过氧化物,所述的过氧化氢是质量分数为0.1%~50%的过氧化氢溶液,优选10%~40%的过氧化氢溶液。所述的烷基过氧化物包括但不限于二甲基过氧化物、二乙基过氧化物、叔丁基甲基过氧化物、二仲丁基过氧化物、二叔丁基过氧化物、叔丁基叔戊基过氧化物、叔丁基过氧化异丙苯、2,5-二甲基-2,5-双(叔丁基过氧基)己烷、2,5-二甲基-2,5-双(叔丁基过氧基)-3-己炔、过氧化二异丙苯、1,4-二(2-叔丁基过氧基异丙基)苯、环己基过氧化氢、过氧化氢异丙苯等。
第一种方法的步骤1或第二种方法的步骤2所述的环氧化反应中,所述的催化剂包括但不限于无机酸催化体系、阳离子交换树脂催化体系、有机酸催化体系、硫酸铝催化体系、间氯过氧化苯甲酸催化体系、过氧化叔丁醇催化体系、酶催化体系、钛硅分子筛类催化剂、杂多化合物催化体系、金属配合物催化体系、甲基三氧化铼催化体系、金属有机配合物催化体系等,优选钨化合物、钛硅分子筛类催化剂和磷化合物催化体系,分别是钨酸或钨酸钠和氨甲基膦酸、磷酸、磷酸二氢钠或磷酸二氢钾、具有MFI拓扑结构的钛硅分子筛等,催化剂的总用量是反应物总质量的0.01%~10.0%,优选0.05%~5%。
根据本发明,过氧化物与催化剂的加入方式可以采取以下三种方式:(1)过氧化物可与催化剂一同滴加至反应中间体溶液中,滴加速度控制在1~20滴/秒,优选1~10滴/秒,最优选1~5滴/秒。(2)先将催化剂加入到反应体系中,再单独将过氧化物滴加至反应中间体溶液中,滴加速度控制在1~20滴/秒,优选1~10滴/秒,最优选1~5滴/秒。(3)将过氧化物与催化剂一同加入到反应体系中,采用“一锅法”进行反应。优选第(2)种反应物加料方式。
本发明两种制备方法的反应体系可以使用溶剂,也可以不使用溶剂,所使用的溶剂可以是极性溶剂也可以是非极性溶剂,溶剂的用量与反应物的质量按质量比计可以是1~300%,优选10%~150%,进一步优选30%~100%。具体可以包括但不限于芳烃类、溶剂油、环氧烷烃、环烷烃、正构烷烃、异构烷烃、石油醚等;所述的溶剂优选芳烃、溶剂油、正戊烷、正己烷、石油醚、二硫化碳、二氧化碳、甲酸甲酯、甲基叔丁基醚、二甲氧基乙烷、二甲基醚、二甲氧基甲烷、乙基甲基醚、二乙基醚和丙酮等一种或多种。
本发明提供的制备工艺可以在常压条件下进行,也可以在加压条件下进行,压力范围可以在0.01Mpa~10Mpa范围内。优选在常压条件下进行反应。
本发明提供一种所述抗磨添加剂在燃料油中的应用方法,其中包括:在燃料油加入所述抗磨剂,以不含添加剂的基础燃料计,所述抗磨剂在燃料油中的添加量为10~5000mg/kg,优选50~1000mg/kg,进一步优选100~500mg/kg。
本发明提供一种所述抗磨性添加剂在润滑油中的应用方法,其中包括,所述抗磨剂在润滑油中的添加量以润滑油基础油质量计,为0.01%~30%,优选0.05~20%,进一步优选0.1%~10%。
本发明还提供一种燃料油组合物,其中包括基础燃料和本发明所述抗磨剂,所述抗磨剂在燃料油中的添加量以基础燃料计,为10~5000mg/kg,优选50~1000mg/kg,进一步优选100~500mg/kg。
本发明还提供一种润滑油组合物,其中包括润滑油基础油和本发明所述抗磨剂,所述抗磨剂在润滑油中的添加量以润滑油基础油质量计,为0.01%~30%,优选0.05~20%,进一步优选0.1%~10%。
所述的基础燃料可包括所有的石油基来源燃料,如中间馏分燃料、柴油燃料、汽油、喷气燃料、煤油、船用油以及其他低硫燃料、高沥青质燃料、液化石油气燃料等;生物可再生燃料,如生物柴油燃料、生物质制油(BTL)燃料等;合成燃料,如天然气合成油(GTL)燃料以及其他合成燃料等;煤基来源燃料,如醇、醚、F-T合成燃料、煤制油(CTL)燃料、衍生自煤和/或石油焦的燃料;其他燃料,如基因工程生物燃料和农作物及其提取物燃料,以及天然气等。优选燃料包括汽油燃料、柴油燃料。
所述的润滑油基础油包括但不限于矿物基础油、合成基础油以及生物基础油。
根据使用需要,本发明提供的添加剂还可以与其它添加剂,如清净分散剂、金属减活剂、防腐剂等同时使用。
本发明提供的抗磨剂,与现有技术相比,有以下几个突出特点:
(1)合成工艺简单,合成步骤短且易操作,反应条件温和,反应过程容易控制;
(2)所述抗磨剂产品在油品中的加剂量少,能够显著改善油品的润滑性能。
(3)产品具有良好的稳定性,不易氧化、变质,能够长期保持良好的抗磨效果。
(4)原料来源广泛,且价格低廉,生产成本较低。
附图说明
图1是空白柴油的磨斑图。
图2是实施例3在空白柴油中加入200mg/kg剂量的磨斑图。
图3是制备例所得抗磨剂产品的红外光谱图。
具体实施方式
以下将通过实施例对本发明进行详细描述。应理解的是本发明能够在不同的实施方式上具有各种的变化,其皆不脱离本发明的范围,且其中的说明在本质上是当作说明之用,而非用以限制本发明。
下面的实施例将对本发明做进一步的说明。
制备例1
将49g(0.5mol)马来酸酐(分析纯,北京伊诺凯科技有限公司)和65.5g(0.5mol)异辛醇(分析纯,北京伊诺凯科技有限公司)置于一装有电动搅拌器、温度计、回流冷凝管、滴液漏斗及氮气导入管的反应器中,通入氮气5~10分钟,并在反应过程中保持微弱的氮气流,加热搅拌升温至100℃,马来酸酐与异辛醇的摩尔比约为1:1,反应时间为1.5小时。制备马来酸单异辛酯反应中间体,得到反应中间体约113.6g。
将113.6g反应中间体置于一个带有三口烧瓶的反应器中,加入12g钨酸钠作催化剂,钨酸钠质量约占反应中间体质量的10%,升温至65℃,搅拌并缓慢滴加85g双氧水(质量分数30%,上海阿拉丁生化科技股份有限公司),马来酸单异辛酯与双氧水的物质的量比约为1:3,控制滴加速率为2滴/秒,反应3小时,产品冷却,干燥,过滤,得到产物约196.4g,反应流程如反应式1所示。
(反应式1)
制备例2
将49g(0.5mol)马来酸酐(分析纯,北京伊诺凯科技有限公司)和61.3(0.6mol)正己醇(分析纯,北京伊诺凯科技有限公司)置于一个装有电动搅拌器、温度计、回流冷凝管、滴液漏斗及氮气导入管的反应器中,通入氮气5~10分钟,并在反应过程中保持微弱的氮气流,加热搅拌升温至85℃,马来酸酐与正己醇的摩尔比约为1:1.2,反应时间为1.5小时。制备马来酸单正己醇酯反应中间体,得到反应中间体约109.6g。
将109.6g反应中间体置于一个带有三口烧瓶的反应器中,加入11g钛硅分子筛作催化剂,钛硅分子筛催化剂的质量约占反应中间体质量的10%,升温至65℃,搅拌并缓慢滴加37.5g双氧水(质量分数30%,上海阿拉丁生化科技股份有限公司),马来酸单正己醇酯与双氧水的物质的量比约为1:2,控制滴加速率为2滴/秒,反应6小时,产品冷却,干燥,过滤,得到产物约139.3g,反应流程如反应式2所示。
(反应式2)
制备例3
将49g(0.5mol)马来酸酐(分析纯,北京伊诺凯科技有限公司)置于一个装有搅拌、滴液器、回流冷凝管、温度计及加热装置的三口烧瓶反应器中,加入2.5g钨酸钠(分析纯,北京伊诺凯科技有限公司),通入氮气5~10分钟,并在反应过程中保持微弱的氮气流,升温至70℃至马来酸酐完全熔化成液体,称取51g(1.5mol)30%过氧化氢溶液(北京伊诺凯科技有限公司)滴加至马来酸酐溶液中,控制滴加速度约为2~5滴/s,保持温度为70℃,反应6小时。制得环氧马来酸酐反应中间体,经过滤、静置,得到产物约为96.5g。
将96.5g环氧化马来酸酐置于一个装有搅拌、滴液器、回流冷凝管、温度计及加热装置的三口烧瓶反应器中,称取183g异壬醇(分析纯,北京伊诺凯科技有限公司)加入到反应体系中,升温至150℃,反应2.5h,制备环氧化马来酸单异壬酯。将产物旋转蒸馏处理以提纯环氧化马来酸单异壬酯,得到产物约267.9g,即得所需环氧琥珀酸单异壬酯。
制备例4
将49g(0.5mol)马来酸酐(分析纯,北京伊诺凯科技有限公司)和157.3g(0.5mol)12-羟基硬脂酸甲酯(99%,上海阿拉丁生化科技股份有限公司)置于一个装有电动搅拌器、温度计、回流冷凝管、滴液漏斗及氮气导入管的反应器中,90℃~120℃沸程石油醚用量50g作溶剂,通入氮气5~10分钟,并在反应过程中保持微弱的氮气流,加热搅拌升温至110℃,马来酸酐与12-羟基硬脂酸甲酯的摩尔比约为1:1,反应时间为2.5小时。制备12-羟基硬脂酸甲酯基马来酸单酯反应中间体,蒸出溶剂,得到反应中间体约205.7g。
将205.7g反应中间体置于一个带有三口烧瓶的反应器中,加入10g钨酸钠作催化剂,钨酸钠质量约占反应中间体质量的10%,升温至65℃,搅拌并缓慢滴加85g双氧水(质量分数30%,上海阿拉丁生化科技股份有限公司),12-羟基硬脂酸甲酯基马来酸单酯与双氧水的物质的量比约为1:5,控制滴加速率为2滴/秒,反应8小时,产品冷却,干燥,过滤,得到产物约285.1g。反应式如式3所示。
(反应式3)
实施例1
将制备例1所示制备的抗磨剂产品在空白柴油中加入75mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例2
将制备例1所示制备的抗磨剂产品在空白柴油中加入100mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例3
将制备例1所示制备的抗磨剂产品在空白柴油中加入200mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例4
将制备例2所示制备的抗磨剂产品在空白柴油中加入75mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例5
将制备例2所示制备的抗磨剂产品在空白柴油中加入100mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例6
将制备例2所示制备的抗磨剂产品在空白柴油中加入200mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例7
将制备例3所制备的抗磨剂产品在空白柴油中加入100mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例8
将制备例4所制备的抗磨剂产品在空白柴油中加入200mg/kg,采用高频往复试验机(HFRR)评价加剂柴油的润滑性能。
实施例9
将制备例1所示制备的抗磨剂产品在10W/40润滑油中加入2%(质量分数),润滑油的抗磨减摩性能采用四球摩擦磨损试验机进行评价,试验条件为75℃、40kg、1200rpm。
对比例1
将49g(0.5mol)马来酸酐(分析纯,北京伊诺凯科技有限公司)和143.5g(1.1mol)异辛醇(分析纯,北京伊诺凯科技有限公司)置于一装有电动搅拌器、温度计、回流冷凝管、滴液漏斗及氮气导入管的反应器中,通入氮气5~10分钟,并在反应过程中保持微弱的氮气流,加热搅拌升温至120℃,马来酸酐与异辛醇的摩尔比约为1:2.2,反应时间为4小时。制备马来酸双异辛酯反应中间体,得到反应中间体约190.6g。
将190.6g反应中间体置于一个带有三口烧瓶的反应器中,加入19g钨酸钠作催化剂,钨酸钠质量约占反应中间体质量的10%,升温至65℃,搅拌并缓慢滴加57.3g双氧水(质量分数30%,上海阿拉丁生化科技股份有限公司),马来酸双异辛酯与双氧水的物质的量比约为1:3,控制滴加速率为2滴/秒,反应8小时,产品冷却,干燥,过滤,得到产物约245.7g。
将产品以200mg/kg的加剂量加入到空白柴油中,考察加剂柴油的润滑性能。
对比例2
将49g(0.5mol)马来酸酐(分析纯,北京伊诺凯科技有限公司)和78.5(0.6mol)异辛醇(分析纯,北京伊诺凯科技有限公司)置于一装有电动搅拌器、温度计、回流冷凝管、滴液漏斗及氮气导入管的反应器中,通入氮气5~10分钟,并在反应过程中保持微弱的氮气流,加热搅拌升温至105℃,马来酸酐与异辛醇的摩尔比约为1:1.2,反应时间为2.5小时。制备马来酸单异辛醇酯约126.6g。
将马来酸单异辛醇酯以200mg/kg、100mg/kg和75mg/kg的加剂量加入到空白柴油,考察加剂柴油的润滑性能。
对比例3
表1为空白柴油的基本理化性能,选用的空白柴油,其典型特征在于空白柴油的润滑性能(WS1.4)为640μm,不满足柴油的润滑性能使用需求。
表1柴油的理化性能
表2柴油的润滑性评价结果
油样 | <![CDATA[加剂量/mg·kg<sup>-1</sup>]]> | WS1.4/μm |
空白柴油 | 0 | 640 |
实施例1 | 75 | 422 |
实施例2 | 100 | 337 |
实施例3 | 200 | 172 |
实施例4 | 75 | 395 |
实施例5 | 100 | 224 |
实施例6 | 200 | 218 |
实施例7 | 100 | 354 |
实施例8 | 200 | 204 |
对比例1 | 200 | 644 |
对比例2 | 75 | 552 |
对比例2 | 100 | 375 |
对比例2 | 200 | 237 |
对比例3 | 200 | 424 |
从表2可见,所制备的抗磨剂产品在空白柴油中的加剂量小,能够显著改善低硫柴油的润滑性能。另外,通过对比实施例1~3与对比例2可以发现,环氧化马来酸单异辛酯的抗磨效果优于马来酸单异辛酯,在相同加剂量时,环氧马来酸单异辛酯的抗磨效果优于马来酸单异辛酯,尤其在加剂量75mg/kg时,马来酸单异辛酯的抗磨效果较差,而环氧马来酸单异辛酯仍能保持良好的抗磨效果。这一发现是出人意料的。
通过对比实施例1~3与对比例1可以发现,环氧化的单酯化合物的抗磨效果绝对优于环氧化的双酯化合物,即在相同加剂量的前提下,环氧化的单酯化合物能显著改善柴油的润滑性能,但是环氧化的双酯化合物却没有任何抗磨效果。
另一方面,所制备的抗磨剂产品优于目前市售的抗磨剂产品,在保持相近抗磨效果的前提下,本发明提供的抗磨剂产品在柴油中的加剂量小于市售抗磨剂产品的加剂量。
表3抗磨剂的稳定性考察
油样 | 储存时长 | 润滑性能(WS1.4)/μm |
实施例3 | 1天 | 172 |
实施例3 | 7天 | 197 |
实施例3 | 15天 | 209 |
实施例3 | 30天 | 206 |
对比例1 | 1天 | 644 |
对比例1 | 7天 | 659 |
对比例1 | 15天 | 670 |
对比例1 | 30天 | 660 |
从表3可见,本发明提供的抗磨剂产品在存储条件下,长时间能够保持良好的抗磨性能。
表4润滑油的润滑性评价结果
油样 | 磨斑直径/mm | 摩擦系数 |
市售油 | 0.4 | 0.107 |
实施例9 | 0.36 | 0.103 |
从表4可以看出,在润滑油中加入本发明提供的抗磨剂产品,磨斑直径和摩擦系数均有所降低,可以改善润滑油的减摩性能。
Claims (17)
2.按照权利要求1所述的添加剂,其中,R1、R2为单键或C1~C10的烷烃或烯烃,R3、R4为氢或C1~C5的烷烃或烯烃;X、Y基团为氢或C4~C30的烷烃、烯烃、含氧官能团或含氮官能团。
3.按照权利要求1所述的添加剂,其中,R1、R2为单键或C1~C4的烷烃或烯烃,R3、R4为氢或C1~C2的烷烃或烯烃;X、Y基团为氢或C4~C20的正烷烃、烯烃、含氧官能团、含氮官能团。
4.按照权利要求1所述的添加剂,其中,所述结构式1的化合物选自以下化合物:环氧琥珀酸单正丁酯、环氧琥珀酸单异丁酯、环氧琥珀酸单正戊酯、环氧琥珀酸单异戊酯、环氧琥珀酸单正辛酯、环氧琥珀酸单异辛酯、环氧琥珀酸单正壬酯、环氧琥珀酸单异壬酯、环氧琥珀酸单月桂酯、环氧琥珀酸单十八醇酯、环氧琥珀酸单油醇酯等;环氧琥珀酸单环戊醇酯、环氧琥珀酸单环己醇酯、环氧琥珀酸单聚乙二醇单甲醚基酯、环氧琥珀酸单聚乙二醇酯、环氧琥珀酸聚丙二醇酯、环氧琥珀酸聚丙二醇单丁醚酯、环氧琥珀酸单蓖麻油酸基酯、环氧琥珀酸单蓖麻油酸甲酯基酯、12-羟基硬脂酸基环氧琥珀酸单酯、12-羟基硬脂酸甲酯基环氧琥珀酸单酯。
5.一种抗磨添加剂的制备方法,其中包括:
(1)由不饱和二元酸或酸酐与含羟基的化合物进行半酯化反应,获得反应中间体;
(2)再将反应中间体与过氧化物在催化剂存在下进行环氧化反应,得到产品。
6.按照权利要求5所述的制备方法,其中,步骤(1)中,半酯化反应温度为20~200℃,优选50~150℃,最优选75~120℃;反应时间为0.5~20小时,优选1~10小时,最优选1~4小时;其不饱和二元酸或酸酐与含羟基的化合物的摩尔比为1:0.1~5,优选1:0.5~3,最优选1:1~2。
7.按照权利要求5所述的制备方法,其中,步骤(2)中,反应中间体与过氧化物的摩尔比为1:0.1~10,优选1:0.5~5,最优选1:1~3;反应时间为0.5~20小时,优选1~10小时;反应温度为0~180℃,进一步优选20~150℃,最优选30~100℃。
8.一种抗磨添加剂的制备方法,其中包括以下步骤:
(1)由不饱和二元酸或酸酐与过氧化物在催化剂存在下进行环氧化反应,获得反应中间体;
(2)再将反应中间体与含羟基的化合物进行半酯化反应,得到产品。
9.按照权利要求6所述的制备方法,其中,其中,步骤(1)中,环氧化反应的温度为0℃~180℃,优选20℃~150℃,最优选30℃~100℃;环氧化反应时间为0.5h~30h,优选1h~20h,最优选6h~10h;所述不饱和二元酸或酸酐与过氧化物的摩尔比为1:0.1~10,优选1:0.5~5,最优选1:1~3。
10.按照权利要求6所述的制备方法,其中,步骤(2)中,所述的半酯化反应温度为20~200℃,优选50~150℃,最优选75~120℃;反应时间为0.5h~20h,优选1h~10h,最优选1h~4h;环氧化物中间体与含羟基的化合物的摩尔比为1:0.1~5,优选1:0.5~3,最优选1:1~2。
11.按照权利要求5或6所述的制备方法,其中,所述的不饱和二元酸或酸酐选自顺丁烯二酸、反丁烯二酸、顺丁烯二酸酐、反丁烯二酸酐、2,3-二甲基马来酸、2,3-二甲基马来酸酐、2-甲基马来酸、2-甲基马来酸酐、戊烯二酸、戊烯二酸酐、3-甲基戊烯二酸、癸烯二酸、癸烯二酸酐、己二烯二酸、十二碳烯二酸、十八碳烯二酸、二十碳烯二酸。
12.按照权利要求5或6所述的制备方法,其中,所述羟基化合物选自C1~C50,优选C4~C30,进一步优选C4~C20的脂肪醇、羟基脂肪酸、羟基脂肪酸酯、羟基脂肪胺、羟基酰胺、醚醇、酚类化合物。
13.按照权利要求5或6所述的制备方法,其中,所述的过氧化物选自过氧化氢、过氧酸、烷基过氧化物。
14.一种抗磨添加剂在燃料油中的应用方法,其中包括:在燃料油中加入权利要求1~4之一所述抗磨添加剂,以基础燃料计,所述抗磨剂在燃料油中的添加量为10~5000mg/kg,优选50~1000mg/kg,进一步优选100~500mg/kg。
15.一种抗磨添加剂在润滑油中的应用方法,其中包括,在润滑油中加入权利要求1~4之一所述抗磨添加剂,以润滑油基础油质量计,所述抗磨剂的添加量为0.01%~30%,优选0.05~20%,进一步优选0.1%~10%。
16.一种燃料油组合物,其中包括基础燃料和权利要求1~4之一所述抗磨添加剂,所述抗磨剂在燃料油中的添加量以基础燃料计,为10~5000mg/kg,优选50~1000mg/kg,进一步优选100~500mg/kg。
17.一种润滑油组合物,其中包括润滑油基础油和权利要求1~4之一所述抗磨添加剂,以润滑油基础油质量计,所述抗磨剂在润滑油中的添加量为0.01%~30%,优选0.05~20%,进一步优选0.1%~10%。
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CN202111155603.5A CN115895752A (zh) | 2021-09-30 | 2021-09-30 | 一种抗磨添加剂、其制备方法及在油品中的应用 |
TW111137220A TW202315932A (zh) | 2021-09-30 | 2022-09-30 | 一種潤滑性改進劑及其在油品中的應用 |
PCT/CN2022/122983 WO2023051747A1 (zh) | 2021-09-30 | 2022-09-30 | 一种润滑性改进剂及其在油品中的应用 |
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JPS53108936A (en) * | 1977-03-04 | 1978-09-22 | Taisho Pharmaceut Co Ltd | Epolysuccinic monoester derivative |
DE2738822A1 (de) * | 1977-08-29 | 1979-03-22 | Taisho Pharma Co Ltd | Epoxysuccinsaeuremonoester |
JPS59108774A (ja) * | 1982-12-13 | 1984-06-23 | Nippon Chemiphar Co Ltd | エポキシコハク酸モノエステルの製造法 |
CN101544621A (zh) * | 2009-02-26 | 2009-09-30 | 山东轻工业学院 | 环氧化马来酸单酯及其合成方法 |
CN102762704A (zh) * | 2010-03-31 | 2012-10-31 | 雪佛龙奥伦耐有限责任公司 | 含有环氧化物抗磨损剂的润滑油组合物 |
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DE10125158A1 (de) | 2001-05-22 | 2002-12-05 | Basf Ag | Nieder-und hochmolekulare Emulgatoren, insbesondere auf Bassis von Polyisobutylen, sowie deren Mischungen |
FR2888248B1 (fr) * | 2005-07-05 | 2010-02-12 | Total France | Composition lubrifiante pour melange hydrocarbone et produits obtenus |
CN101768480B (zh) | 2010-03-16 | 2013-06-05 | 王著 | 一种低酸高效柴油抗磨剂及其制备方法 |
CN103540369B (zh) | 2013-10-28 | 2015-02-11 | 山东泰德新能源有限公司 | 一种低硫柴油润滑剂 |
CN109576063B (zh) | 2017-09-28 | 2022-08-12 | 中国石油化工股份有限公司 | 一种一步法合成低硫柴油抗磨剂的方法 |
CN109929624B (zh) | 2019-04-25 | 2020-02-07 | 上海鑫灵精细化工有限公司 | 一种脂肪酸类柴油抗磨剂的组成物及配制方法 |
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2022
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JPS53108936A (en) * | 1977-03-04 | 1978-09-22 | Taisho Pharmaceut Co Ltd | Epolysuccinic monoester derivative |
DE2738822A1 (de) * | 1977-08-29 | 1979-03-22 | Taisho Pharma Co Ltd | Epoxysuccinsaeuremonoester |
JPS59108774A (ja) * | 1982-12-13 | 1984-06-23 | Nippon Chemiphar Co Ltd | エポキシコハク酸モノエステルの製造法 |
CN101544621A (zh) * | 2009-02-26 | 2009-09-30 | 山东轻工业学院 | 环氧化马来酸单酯及其合成方法 |
CN102762704A (zh) * | 2010-03-31 | 2012-10-31 | 雪佛龙奥伦耐有限责任公司 | 含有环氧化物抗磨损剂的润滑油组合物 |
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