CN114574264B - 复合极压抗磨剂及其制备方法与应用 - Google Patents
复合极压抗磨剂及其制备方法与应用 Download PDFInfo
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- 239000010687 lubricating oil Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 31
- 239000010452 phosphate Substances 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 23
- -1 phosphate ester Chemical class 0.000 claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 230000002378 acidificating effect Effects 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 claims description 16
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 16
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 16
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- 230000007797 corrosion Effects 0.000 abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
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- 230000000694 effects Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- QBCOASQOMILNBN-UHFFFAOYSA-N didodecoxy(oxo)phosphanium Chemical compound CCCCCCCCCCCCO[P+](=O)OCCCCCCCCCCCC QBCOASQOMILNBN-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
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- C07C211/09—Diamines
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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Abstract
Description
技术领域
本发明属于润滑油添加剂领域,涉及一种复合极压抗磨添加剂。具体是涉及一种包含酸性磷酸酯胺铵盐、亚磷酸二烷基酯铵盐和2,5-二巯基噻二唑铵盐中的1-3种组分的极压抗磨添加剂及其制备方法与应用。
背景技术
2,5-二巯基-1,3,4-噻二唑是一类具有稳定结构的杂环化合物,同一个环中包含一个硫原子和两个氮原子,杂环结构紧密,与生物质分子结构相似,杂原子易与金属离子形成配合物,这些特点使其在广泛的领域中具有应用前景,但较差的油溶性限制了其在润滑油中的应用。2,5-二巯基-1,3,4-噻二唑同时包含两个活性的-SH基团,可与卤原子、醛类、胺类、有机金属化合物等进行取代反应、胺化反应亦可进行分子间共聚反应,通过上述反应可提高其衍生物的油溶性。最近,噻二唑类衍生物的抗磨、极压作用得到了进一步认识,作为新型高性能极压抗磨剂开始崭露头角。这类极压抗磨剂不仅无灰,而且还具有抗氧、金属钝化等多方面性能,克服了传统极压添加剂导致油品抗氧化性能降低、铜片腐蚀严重的局限性。作为环境友好、性能优异、具有多功能的极压抗磨剂,噻二唑类衍生物在润滑油中的应用将越来越广泛。
含磷添加剂作为极压抗磨添加剂由来已久,并获得了广泛的工业应用,是目前应用最广、抗磨效果最好的添加剂之一。中性磷酸酯活性较弱,不易在摩擦表面形成化学保护膜,酸性磷酸酯的性能较好,但是酸性较强,在重负荷下易产生化学腐蚀磨损,使其性能变差。为了提高磷酸酯类抗磨剂的抗腐蚀性,将酸性磷酸酯做成胺盐,调节添加剂的化学活性和极性,即保持了良好的极压抗磨性,又可减少腐蚀。专利US 2371853、US 3197405和US5756429详细报道了不同类型磷酸酯胺盐的制备方法、使用范围和性能评价等。与酸性磷酸酯相比,亚磷酸二烷基酯具有更高的反应活性,在低载荷下表现出更优异的减磨性能,但亚磷酸酯中磷元素活性高磷保持能力差,使用过程中会发生氧化作用,产生酸性物质和油泥,易发生摩擦系数突增现象,影响油品性能。因此,将酸性磷酸酯、亚磷酸二烷基酯和2,5-二巯基-1,3,4-噻二唑进行适当复配,通过一步胺化反应合成一种复合极压抗磨添加剂,通过有机胺的引入一方面调节酸性磷酸酯和亚磷酸二烷基酯的化学活性和极性,降低腐蚀;另一方面提高2,5-二巯基-1,3,4-噻二唑的油溶性。
发明内容
本发明的目的在于提供一种包含酸性磷酸酯铵盐、亚磷酸二烷基酯铵盐和2,5-二巯基噻二唑铵盐中的1-3种组分的复合极压抗磨添加剂及其制备方法与应用。
为达上述目的,本发明提供一种复合极压抗磨添加剂,该复合极压抗磨添加剂包含如下式(1)、式(2)和式(3)所示结构的有效组分中的至少一种:
其中,R1、R2相同或不同,分别表示H原子、直链或支链的C1~C14的烃基;R3、R4相同或不同,分别表示H原子、直链或支链的C4~C18的烃基;R5、R6相同或不同,分别表示直链或支链的C4~C14的烃基。
本发明还提供一种复合极压抗磨添加剂的制备方法,包括以下步骤:
步骤(1)酸性磷酸酯的制备:
将一定量的五氧化二磷和溶剂加入反应器中,氮气保护,搅拌混合均匀,加入一定比例的脂肪醇或芳香醇,升温反应,减压蒸馏除去溶剂,得到酸性磷酸酯。
步骤(2)含酸性磷酸酯、亚磷酸二烷基酯和2,5-二巯基噻二唑混合铵盐的复合极压抗磨添加剂的制备:
将步骤(1)所述的酸性磷酸酯,亚磷酸二烷基酯、2,5-二巯基噻二唑和溶剂加入反应容器中,搅拌混合均匀,升温,然后将一定比例的有机胺滴加到反应器中,继续反应,减压蒸馏除去溶剂,得到复合极压抗磨添加剂。
本发明的步骤(1)中所述溶剂为石油醚、苯、甲苯、环己烷、正庚烷中的一种或两种以上的混合物。
本发明的步骤(1)中所述脂肪醇为甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、戊醇、己醇、庚醇、辛醇、异辛醇、癸醇、月桂醇、十四醇中的一种或两种。
本发明的步骤(1)中所述芳香醇为苯甲醇、甲基苯甲醇、乙基苯甲醇、异丙基苯甲醇、苯乙醇、甲基苯乙醇、异丙基苯乙醇、壬基酚聚氧乙烯醚中的一种或两种。
本发明的步骤(1)中所述脂肪醇或芳香醇与五氧化二磷的摩尔比为2:1~4:1。
本发明的步骤(1)中所述升温反应的温度为60~140℃,反应时间为3~8小时。
本发明的步骤(2)中所述亚磷酸二烷基酯是由以下式(4)表示的亚磷酸二烷基酯,其中R5、R6相同或不同,分别表示直链或支链的C4~C14的烃基。
本发明的步骤(2)中所述溶剂为石油醚、苯、甲苯、环己烷、正庚烷、二甲苯中的一种或两种以上的混合物。
本发明的步骤(2)中所述有机胺是由以下式(5)表示的有机胺,其中R3、R4相同或不同,分别表示H原子、直链或支链的C4~C18的烃基,
本发明的步骤(2)中所述酸性磷酸酯、亚磷酸二烷基酯、2,5-二巯基噻二唑和有机胺的摩尔比为a:b:(0.1~0.3)*(a+b):(1.0~2.6)*(a+b),其中0≤a,0≤b。
本发明的步骤(2)中所述升温温度为80~140℃;所述有机胺在1~2小时内滴加到反应器中;所述反应时间为2~6小时。
本发明首先利用五氧化二磷与醇反应制备酸性磷酸酯,然后按一定比例将酸性磷酸酯、亚磷酸二烷基酯和2,5-二巯基-1,3,4-噻二唑中的1-3种组分进行复配,通过一步胺化反应合成一种复合极压抗磨添加剂。其生产工艺简单易操作,安全环保,后处理工艺简单,生产成本低,生产可根据具体需要制备不同系列的复合极压抗磨添加剂产品,该产品具有优异的极压抗磨和抗腐蚀性能。
本发明的复合极压抗磨添加剂可作为润滑油极压抗磨和抗腐蚀添加剂单独使用,也可以和其它润滑油添加剂复合使用,该复合极压抗磨添加剂在基础油中的添加量为0.2wt%~10wt%。
具体实施方式
以下结合具体实施例对本发明作进一步详细描述。
实施例1
(1)将142g五氧化二磷(1摩尔)和300g正庚烷加入到反应器中,氮气保护,搅拌混合均匀,加入138g的乙醇(3摩尔),升温至60℃,持续反应5小时后,减压蒸馏除去溶剂,得到酸性磷酸酯A。(2)将200g酸性磷酸酯A,194g亚磷酸二丁酯、51.3g 2,5-二巯基噻二唑和400g石油醚加入反应容器中,搅拌混合均匀,升温至80℃,然后将400g的正辛胺2小时内滴加到反应器中,继续反应6小时后,减压蒸馏除去溶剂,得到复合极压抗磨添加剂1。
实施例2
(1)将142g五氧化二磷(1摩尔)和300g环己烷加入到反应器中,氮气保护,搅拌混合均匀,加入222g的丁醇(3摩尔),升温至75℃,持续反应5小时后,减压蒸馏除去溶剂,得到酸性磷酸酯B。(2)将182g酸性磷酸酯B,153g亚磷酸二异辛酯、30g 2,5-二巯基噻二唑和400g石油醚加入反应容器中,搅拌混合均匀,升温至95℃,然后将259g的十二胺2小时内滴加到反应器中,继续反应6小时后,减压蒸馏除去溶剂,得到复合极压抗磨添加剂2。
实施例3
(1)将71g五氧化二磷(0.5摩尔)和150g甲苯加入到反应器中,氮气保护,搅拌混合均匀,加入260g的异辛醇(2摩尔),升温至80℃,持续反应5小时后,减压蒸馏除去溶剂,得到酸性磷酸酯C。(2)将50g酸性磷酸酯C,17g亚磷酸二月桂酯、3.6g 2,5-二巯基噻二唑和100g石油醚加入反应容器中,搅拌混合均匀,升温至120℃,然后将68g的十八胺2小时内滴加到反应器中,继续反应5小时后,减压蒸馏除去溶剂,得到复合极压抗磨添加剂3。
实施例4
(1)将71g五氧化二磷(0.5摩尔)和500g石油醚加入到反应器中,氮气保护,搅拌混合均匀,加入859g壬基酚聚氧乙烯醚(NP-8,1.5摩尔),升温至80℃,持续反应6小时后,减压蒸馏除去溶剂,得到酸性磷酸酯D。(2)将186g酸性磷酸酯D,4.5g 2,5-二巯基噻二唑和200g二甲苯加入反应容器中,搅拌混合均匀,升温至130℃,然后将25.8g的二丁胺2小时内滴加到反应器中,继续反应6小时后,减压蒸馏除去溶剂,得到复合极压抗磨添加剂4。
实施例5
将109g酸性磷酸酯B、160g酸性磷酸酯C和300g石油醚加入反应容器中,搅拌混合均匀,升温至100℃,然后将133g的十二胺2小时内滴加到反应器中,继续反应4小时后,减压蒸馏除去溶剂,得到复合极压抗磨添加剂5。
实施例6
将194g亚磷酸二丁酯、153g亚磷酸二异辛酯、45g 2,5-二巯基噻二唑和300g甲苯加入反应容器中,搅拌混合均匀,升温至110℃,然后将361g的二辛胺2小时内滴加到反应器中,继续反应5小时后,减压蒸馏除去溶剂,得到复合极压抗磨添加剂6。
将实施例1-6得到的复合极压抗磨添加剂以1.0wt%的添加量调入GL-5齿轮油试验油中,随后对该润滑油在392N载荷下的磨斑直径(WSD)、最大无卡咬负荷(PB值)和铜片腐蚀性能进行了测定,结果见表1。表1的结果表明该产品具有优异的极压抗磨性和抗腐蚀性能。
依据GB/T 3142-1982的方法测定了最大无卡咬负荷(PB值),依据NB/SH/T 0189-2017的方法测定了钢球的磨斑直径(WSD)。依据GB/T 5096的方法进行100℃铜片腐蚀试验。
表1实施例1-6制得的复合极压抗磨添加剂性能评价
Claims (14)
2.一种根据权利要求1所述的复合极压抗磨添加剂的制备方法,其特征在于,包括以下步骤:
步骤(1)酸性磷酸酯的制备:
将五氧化二磷和溶剂加入反应器中,氮气保护,搅拌混合均匀,加入脂肪醇或芳香醇,升温反应,减压蒸馏除去溶剂,得到酸性磷酸酯;
步骤(2)含酸性磷酸酯、亚磷酸二烷基酯和2,5-二巯基噻二唑混合铵盐的复合极压抗磨添加剂的制备:
将步骤(1)的酸性磷酸酯、亚磷酸二烷基酯、2,5-二巯基噻二唑和溶剂加入反应容器中,搅拌混合均匀,升温,然后将有机胺滴加到反应器中,继续反应,减压蒸馏除去溶剂,得到复合极压抗磨添加剂。
3.根据权利要求2所述的制备方法,其特征在于,步骤(1)中所述溶剂为石油醚、苯、甲苯、环己烷和正庚烷中的至少一种。
4.根据权利要求2所述的制备方法,其特征在于,步骤(1)中所述脂肪醇为甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、戊醇、己醇、庚醇、辛醇、异辛醇、癸醇、月桂醇和十四醇中的至少一种。
5.根据权利要求2所述的制备方法,其特征在于,步骤(1)中所述芳香醇为苯甲醇、甲基苯甲醇、乙基苯甲醇、异丙基苯甲醇、苯乙醇、甲基苯乙醇、异丙基苯乙醇和壬基酚聚氧乙烯醚中的至少一种。
6.根据权利要求2所述的制备方法,其特征在于,步骤(1)中所述脂肪醇或芳香醇与五氧化二磷的摩尔比为2:1~4:1。
7.根据权利要求2所述的制备方法,其特征在于,步骤(1)中所述升温反应的温度为60~140℃,反应时间为3~8小时。
9.根据权利要求2所述的制备方法,其特征在于,步骤(2)中所述溶剂为石油醚、苯、甲苯、环己烷、正庚烷和二甲苯中的至少一种。
11.根据权利要求2所述的制备方法,其特征在于,步骤(2)中所述酸性磷酸酯、亚磷酸二烷基酯、2,5-二巯基噻二唑和有机胺的摩尔比为a:b:(0.1~0.3)*(a+b):(1.0~2.6)*(a+b),其中0≤a,0≤b。
12.根据权利要求2所述的制备方法,其特征在于,步骤(2)中所述升温温度为80~140℃;所述有机胺在1~2小时内滴加到反应器中;所述反应时间为2~6小时。
13.一种根据权利要求1所述的复合极压抗磨添加剂在润滑油添加剂中的应用,其特征在于,所述添加剂作为润滑油极压、抗磨、减磨和抗腐蚀添加剂单独使用,或者和其它润滑油添加剂复合使用。
14.根据权利要求13所述的应用,其特征在于,所述复合极压抗磨添加剂在基础油中的添加量为0.2wt%~10wt%。
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