CN110317668B - 一种润滑脂及其制备方法 - Google Patents
一种润滑脂及其制备方法 Download PDFInfo
- Publication number
- CN110317668B CN110317668B CN201810264888.8A CN201810264888A CN110317668B CN 110317668 B CN110317668 B CN 110317668B CN 201810264888 A CN201810264888 A CN 201810264888A CN 110317668 B CN110317668 B CN 110317668B
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- Prior art keywords
- phosphorus
- grease
- alkylene
- single bond
- lubricating
- Prior art date
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- 239000004519 grease Substances 0.000 title claims abstract description 93
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 58
- 239000011574 phosphorus Substances 0.000 claims abstract description 57
- 239000002562 thickening agent Substances 0.000 claims abstract description 50
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000002199 base oil Substances 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 14
- -1 phosphorus compound Chemical class 0.000 claims description 21
- 239000003963 antioxidant agent Substances 0.000 claims description 15
- 229910052788 barium Inorganic materials 0.000 claims description 14
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 8
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 8
- 239000012990 dithiocarbamate Substances 0.000 claims description 8
- RXQOLRPPIKGXOW-UHFFFAOYSA-N C[ClH]P(=O)[ClH]C Chemical compound C[ClH]P(=O)[ClH]C RXQOLRPPIKGXOW-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
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- 239000003112 inhibitor Substances 0.000 claims description 6
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- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 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 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
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- 238000000034 method Methods 0.000 claims description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 5
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- VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 claims description 2
- IXTGXVWLIBNABC-UHFFFAOYSA-N dichloromethylphosphonic acid Chemical compound OP(O)(=O)C(Cl)Cl IXTGXVWLIBNABC-UHFFFAOYSA-N 0.000 claims description 2
- WDOKISJWRVNYNS-UHFFFAOYSA-N dicyclohexylphosphanium;chloride Chemical compound Cl.C1CCCCC1PC1CCCCC1 WDOKISJWRVNYNS-UHFFFAOYSA-N 0.000 claims description 2
- XSOTVEGLPNWBPO-UHFFFAOYSA-N diphenylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 XSOTVEGLPNWBPO-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
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- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 claims 2
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical compound FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 claims 2
- VIZQREHVDDPWOK-UHFFFAOYSA-N IP(I)(I)=O Chemical compound IP(I)(I)=O VIZQREHVDDPWOK-UHFFFAOYSA-N 0.000 claims 1
- PTLIZOFGXLGHSY-UHFFFAOYSA-N dibutylphosphane Chemical compound CCCCPCCCC PTLIZOFGXLGHSY-UHFFFAOYSA-N 0.000 claims 1
- UHUMDOUHVGSPDJ-UHFFFAOYSA-N diethylphosphane;hydrochloride Chemical compound [Cl-].CC[PH2+]CC UHUMDOUHVGSPDJ-UHFFFAOYSA-N 0.000 claims 1
- YXXQTQYRRHHWFL-UHFFFAOYSA-N diiodophosphanyl(diiodo)phosphane Chemical compound IP(I)P(I)I YXXQTQYRRHHWFL-UHFFFAOYSA-N 0.000 claims 1
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
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Abstract
本发明提出了一种润滑脂及其制备方法。本发明的润滑脂包括润滑基础油、稠化剂和含磷化合物,所述含磷化合物的结构见说明书。本发明的润滑脂具有优异的生物降解性能,环境友好,具有良好的胶体安定性、极佳的机械安定性和优秀的抗氧化作用,能够胜任高温、高速、高负荷、多水等苛刻工况条件。
Description
技术领域
本发明涉及一种润滑脂,特别涉及一种降解性能优异的润滑脂。
背景技术
润滑脂是机械设备正常运转及材料制造加工过程中必要的工作介质,随着工业的高速发展,润滑脂的需求量也越来越大。在润滑脂的储存、运输和使用过程中,也不可避免有泄漏、溢出及不恰当排放等多种污染环境的情况。虽然润滑脂对生物的急性毒性很小,鲜有因接触润滑脂而中毒的相关报道,但是进入环境的润滑脂由于生物降解能力差,严重污染陆地及江河湖泊,同时润滑脂不像润滑油一样比较容易回收处理,因此研究具有生物降解性能的润滑脂就成为解决生态环境问题的突破口。
近年来,废弃及泄漏润滑脂对环境的影响已经引起了人们广泛的关注,为解决这一问题,目前主要利用可生物降解的植物油及酯类合成油制备润滑脂,或使用植物油、酯类油及聚α-烯烃混合油作为基础油制备润滑脂,如CN 1504552A和CN 103265999A报道的可生物降解润滑脂;目前对具有降解性能的以矿物油或聚α-烯烃为主要基础油成分的润滑脂的研究报道尚不多见。
发明内容
本发明提出了一种润滑脂及其制备方法。
具体而言,本发明涉及以下方面的内容。
1.一种润滑脂,包括润滑基础油、稠化剂和含磷化合物,所述含磷化合物的结构为:
式I中的每个A分别独立地选自HO-或R7,至少一个A为其中R1为C2-C30的烃基(优选C5-C25的烃基,更优选C8-C20的烃基),R2为H或C1-C10的烃基(优选H或C1-C8的烷基,更优选H或C1-C6的烷基),R3为单键或C1-C10的亚烃基(优选单键或C1-C8的亚烃基,更优选单键或C1-C4的亚烷基),R4为H或C1-C6的烃基(优选H或C1-C4的烷基,更优选H或C1-C3的烷基),R5为单键或C1-C10的亚烃基(优选单键或C1-C8的亚烷基,更优选单键或C1-C6的亚烷基),R6为单键或C1-C10的亚烃基(优选单键或C1-C8的亚烷基,更优选单键或C1-C6的亚烷基),R7为H或C1-C10的烃基(优选H、C1-C10的烷基、C3-C8的环烷基或C6-C10的芳基,更优选H、C1-C8的烷基、C3-C8的环烷基或C6-C8的芳基)。
在式(I)中,每个A中的R1、R2、R3、R4、R5、R6、R7可以相同,也可以不相同。
所述R1可以选用C2-C30的烷基,也可以选用包含一个或多个不饱和双键的C2-C30烃基,例如可以选用C8-C20的烷基、CH3(CH2)7CH=CH(CH2)7-。
2.一种润滑脂,包括润滑基础油、稠化剂和含磷化合物,所述含磷化合物的制备方法为:将与磷源发生反应的步骤,所述磷源为能够除去羟基氢而与羟基氧成键的磷化合物。其中各基团的定义同前面的叙述。所述磷源优选能够除去羟基氢而与羟基氧形成化学键的磷化合物。所述磷源优选能够除去与R6相连的羟基氢而与其羟基氧形成化学键的磷化合物。
所述磷源优选磷氧卤化合物、磷卤化合物、磷氧化合物、磷酸、亚磷酸、磷酸缩合物和亚磷酸缩合物中的一种或多种,优选磷氧卤化合物、磷卤化合物和磷氧化合物中的一种或多种。
所述磷氧卤化合物可以选用磷氧氟化合物、磷氧氯化合物、磷氧溴化合物和磷氧碘化合物中的一种或多种;所述磷卤化合物可以选用磷氟化合物、磷氯化合物、磷溴化合物和磷碘化合物中的一种或多种;所述磷氧化合物可以选用P2O5、P2O3。
所述磷源可以举出的例子包括二甲基膦酰氯、二乙基膦酰氯、二苯基膦酰氯、二环己基膦酰氯、三氯氧磷、二氯乙基磷酸、二氯甲基磷酸、二甲基氯化膦、二乙基氯化膦、二丁基氯化膦、二苯基氯化膦、二环己基氯化膦、二苯基溴化膦、三氯化膦、三氟化膦、三溴化膦、三碘化膦、五氧化二磷、三氧化二磷、磷酸、亚磷酸和多聚磷酸中的一种或多种。
所述磷源优选磷氧氯化合物。
所述磷源优选其中的D为OH、R7或卤素,每个D可以相同,也可以不相同,至少一个D为OH或卤素。所述卤素为F、Cl、Br或I,优选Cl。所述R7为H或C1-C10的烃基(优选H、C1-C10的烷基、C3-C8的环烷基或C6-C10的芳基,更优选H、C1-C8的烷基、C3-C8的环烷基或C6-C8的芳基)。
在所述与磷源发生的反应中可以加入溶剂,也可以不加入溶剂,优选加入溶剂。所述溶剂优选有机溶剂,更优选有机极性溶剂,例如可以选用四氢呋喃、二氯甲烷、氯仿、丙酮、乙酸乙酯和乙腈中的一种或多种,优选四氢呋喃。所述溶剂的加入量以促进反应顺利进行为宜,并没有特别的限定。
所述反应中可以加入催化剂,也可以不加入催化剂。所述催化剂可以为有机胺,例如可以选用乙胺、二乙胺、三乙胺、正丁胺和吡啶中的一种或多种,优选三乙胺。所述催化剂的加入量优选所述磷源质量的10%~300%。
优选利用溶剂对所述与磷源发生反应的产物进行洗涤、提纯操作,可以进行洗涤的溶剂优选极性有机溶剂,例如可以选用二氯甲烷、氯仿、丙酮、乙酸乙酯和乙腈中的一种或多种,优选二氯甲烷。所述溶剂可通过干燥、蒸发、蒸馏等常规技术手段去除。
优选对所述与磷源发生反应的产物进行洗涤、重结晶操作,以提高反应产物的纯度。所述洗涤操作是对反应产物进行酸洗和/或水洗操作,优选先进行酸洗、后进行水洗操作,所述酸洗操作是用酸液对反应产物进行洗涤操作,所述酸洗操作中的酸液优选盐酸、硫酸或硝酸的水溶液,所述酸液的浓度优选1~12摩尔/升。所述重结晶操作是利用溶剂洗涤反应产物,然后进行重结晶的步骤。所述溶剂优选极性有机溶剂,例如可以选用丙酮、二氯甲烷、三氯甲烷和乙酸乙酯中的一种或多种。
所述R1COOH和/或R1COCl的例子包括月桂酸、肉豆蔻酸、棕榈酸、油酸、硬脂酸、软脂酸、月桂酰氯、肉豆蔻酰氯、棕榈酰氯、油酰氯、硬脂酰氯和软脂酰氯中的一种或多种。
所述酰化反应的反应温度优选-20~30℃,更优选-10~20℃;反应时间优选1~25小时,更优选2~15小时。
在所述酰化反应中可以加入溶剂,也可以不加入溶剂,优选加入溶剂。所述溶剂可以选用极性溶剂,例如可以选用二氯甲烷、氯仿、丙酮、乙酸乙酯、乙腈和水中的一种或多种,优选极性有机溶剂和水的混合物,二者之间的体积比优选为10:1~1:5。
在所述酰化反应中可以加入催化剂,也可以不加入催化剂,优选加入催化剂。所述催化剂可以选用有机碱或无机碱,例如可以选用氢氧化锂、氢氧化钠、氢氧化钾、氢氧化钙、三乙胺、吡啶和4-二甲氨基吡啶中的一种或多种。所述催化剂的加入量优选所述酰化反应中所使用的酰化剂(R1COOH和/或R1COCl)质量的50%~300%,更优选80%~200%。
3.按照前述任一方面所述的润滑脂,以润滑脂总重量为基准,所述含磷化合物占润滑脂总质量的0.01%~10%(优选0.1%-5%);所述稠化剂占润滑脂总质量的3%-40%(优选5%-30%);所述润滑基础油构成润滑脂的主要成分。
所述稠化剂为锂基稠化剂、复合锂基稠化剂、钙基稠化剂、无水钙基稠化剂、复合钙基稠化剂、复合锂钙基稠化剂、钠基稠化剂、复合钠基稠化剂、钡基稠化剂、复合钡基稠化剂、复合铝基稠化剂、聚脲稠化剂、膨润土稠化剂、烃基稠化剂、无机稠化剂和有机稠化剂中的一种或多种,优选锂基稠化剂、复合锂基稠化剂、钙基稠化剂、无水钙基稠化剂、复合钙基稠化剂、复合锂钙基稠化剂、钠基稠化剂、复合钠基稠化剂、钡基稠化剂、复合钡基稠化剂和复合铝基稠化剂中的一种或多种。所述稠化剂优选通过脂肪酸和/或羟基脂肪酸与氢氧化物反应而得。所述脂肪酸和/或羟基脂肪酸优选C12-C20脂肪酸和/或羟基脂肪酸,可以是月桂酸、豆蔻酸、棕榈酸、硬脂酸和12-羟基硬脂酸中的一种或多种,优选12-羟基硬脂酸和/或硬脂酸;所述氢氧化物优选选自氢氧化锂、氢氧化钙、氢氧化钠、氢氧化钡和氢氧化铝中的一种或多种。
所述润滑基础油为矿物油、植物油和合成油中的一种或多种,所述矿物油可以是石蜡基基础油、中间基基础油、环烷基基础油中的一种或多种;所述植物油可以是蓖麻油、菜籽油、花生油和豆油中的一种或多种;所述合成油可以是聚α-烯烃油、酯类油、氟油和硅油中的一种或多种;优选100℃运动粘度为5-60mm2/s的润滑基础油,最优选100℃运动粘度为10-30mm2/s的润滑基础油。
4.按照前述任一方面所述的润滑脂,所述润滑脂中还加入抗氧剂、防锈剂和极压抗磨剂中的一种或多种,所述抗氧剂占润滑脂总质量的0.1%-20%(优选0.2%-10%);所述防锈剂占润滑脂总质量的0.01%-15%(优选0.02%-10%);所述极压抗磨剂占润滑脂总质量的0.01%-15%(优选0.1%-10%);所述抗氧剂优选选自酚类和/或胺类抗氧剂;所述防锈剂优选选自磺酸盐和/或石油磺酸盐;所述极压抗磨剂优选选自氨基硫代酯和/或二烷基二硫代氨基甲酸盐。
5.前述任一方面所述的润滑脂的制备方法,包括:将前述任一方面所述的稠化剂、全部或部分的添加剂、全部或部分的润滑基础油在180-230℃恒温炼制,冷却,加入剩余的添加剂、剩余的润滑基础油,研磨成脂。
所述炼制的时间优选为1-25分钟。
所述添加剂包括前述任一方面所述的含磷化合物、抗氧剂、防锈剂和极压抗磨剂中的一种或多种。
优选地,将前述任一方面所述的稠化剂、部分的添加剂、部分的润滑基础油在180-230℃恒温炼制,冷却,加入剩余的添加剂、剩余的润滑基础油,研磨成脂。其中所述的部分的添加剂优选抗氧剂,可以为部分的抗氧剂,也可以为全部的抗氧剂。
技术效果
本发明的润滑脂具有优异的生物降解性能,环境友好,具有良好的胶体安定性、极佳的机械安定性和优秀的抗氧化作用,能够胜任高温、高速、高负荷、多水等苛刻工况条件。
具体实施方式
下面对本发明的具体实施方式进行详细说明,但是需要指出的是,本发明的保护范围并不受这些具体实施方式的限制。
下述实施例中所述实验方法,如无特殊说明,均为常规方法;所述试剂和材料,如无特殊说明,均可从商业途径获得。
实施例1、合成O-二甲基膦酰基-N-十二烷酰基丝氨酸(见结构式I-a)
1)向反应器中依次加入L-丝氨酸(47.6mmol,5g),40mL丙酮,20mL水,氢氧化钠(95.2mmol,10g),降温至0℃,滴加月桂酰氯(式Ⅱ-a所示)(47.6mmol,10.4g)。反应5小时后使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤。
2)将上述白色固体(17.4mmol,5g),溶于50mL四氢呋喃,加入三乙胺(34.8mmol,3.52g),向其中滴入二甲基膦酰氯(式Ⅲ-a所示)(17.4mmol,1.96g),反应12小时后,使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤,丙酮重结晶得到O-二甲基膦酰基-N-十二烷酰基丝氨酸(式I-a所示)。
结构确证结果如下:1H NMR(400MHz,CDCl3)δ11.92(br,1H),8.34(s,1H),4.77-4.51(m,2H),4.32(t,J=6.8Hz,1H),2.07(t,J=6.8Hz,2H),1.60-1.50(m,2H),1.42-1.21(m,22H),0.81(t,J=7.0Hz,3H);.HRMS(FT-ICRMS)calcd for C17H33NO5P(M-H):362.2102,found:362.2105.
经结构鉴定所合成的化合物确为目标化合物O-二甲基膦酰基-N-十二烷酰基丝氨酸(见结构式I-a)。
实施例2、合成O-二甲基膦酰基-N-十七烷酰基丝氨酸(见结构式I-b)
1)向反应器中依次加入L-丝氨酸(47.6mmol,5g),40mL丙酮,20mL水,氢氧化钠(95.2mmol,10g),降温至0℃,滴加硬脂酰氯(式Ⅱ-b所示)(47.6mmol,14.4g)。反应5小时后使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤。
2)将上述白色固体(17.4mmol,6.46g),溶于50mL四氢呋喃,加入三乙胺(34.8mmol,3.52g),向其中滴入二甲基膦酰氯(式Ⅲ-a所示)(17.4mmol,1.96g),反应12小时后,使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤,丙酮重结晶得到O-二甲基膦酰基-N-十七烷酰基丝氨酸(式I-b所示)。
结构确证结果如下:1H NMR(400MHz,CDCl3)δ11.77(br,1H),8.22(s,1H),4.87-4.66(m,2H),4.27(t,J=7.2Hz,1H),2.01(t,J=7.0Hz,2H),1.66-1.52(m,2H),1.42-1.21(m,34H),0.80(t,J=7.0Hz,3H);HRMS(FT-ICRMS)calcd for C23H45NO5P(M-H):446.3041,found:446.3035.
经结构鉴定所合成的化合物确为目标化合物O-二甲基膦酰基-N-十七烷酰基丝氨酸(见结构式I-b)。
实施例3、合成O-二甲基膦酰基-N-油酰基丝氨酸(见结构式I-c)
1)向反应器中依次加入L-丝氨酸(47.6mmol,5g),40mL丙酮,20mL水,氢氧化钠(95.2mmol,10g),降温至0℃,滴加油酰氯(式Ⅱ-c所示)(47.6mmol,13.45g)。反应5小时后使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤。
2)将上述白色固体(17.4mmol,6.43g),溶于50mL四氢呋喃,加入三乙胺(34.8mmol,3.52g),向其中滴入二甲基膦酰氯(式Ⅲ-a所示)(17.4mmol,1.96g),反应12小时后,使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤,丙酮重结晶得到O-二甲基膦酰基-N-十二烷酰基丝氨酸(式I-c所示)。
结构确证结果如下:1H NMR(400MHz,CDCl3)δ12.32(br,1H),8.47(s,1H),5.71-5.40(m,2H),4.80-4.50(m,2H),4.12(t,J=7.0Hz,1H),2.26-2.09(m,4H),2.02(t,J=7.2Hz,2H),1.65-1.47(m,2H),1.42-1.11(m,26H),0.77(t,J=7.2Hz,3H);.HRMS(FT-ICRMS)calcd for C23H43NO5P(M-H):444.2884,found:444.2877.
经结构鉴定所合成的化合物确为目标化合物O-二甲基膦酰基-N-油酰基丝氨酸(见结构式I-c)。
实施例4、合成O-二乙基膦酰基-N-十二烷酰基丝氨酸(见结构式I-d)
1)向反应器中依次加入L-丝氨酸(47.6mmol,5g),40mL丙酮,20mL水,氢氧化钠(95.2mmol,10g),降温至0℃,滴加月桂酰氯(式Ⅱ-a所示)(47.6mmol,10.4g)。反应5小时后使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤。
2)将上述白色固体(17.4mmol,5g),溶于50mL四氢呋喃,加入三乙胺(34.8mmol,3.52g),向其中滴入二乙基膦酰氯(式Ⅲ-b所示)(17.4mmol,2.45g),反应12小时后,使用6摩尔/升盐酸溶液酸化至pH值为2,出现大量白色固体,抽滤,滤饼用水及石油醚洗涤,丙酮重结晶得到O-二乙基膦酰基-N-十二烷酰基丝氨酸(式I-d所示)。
结构确证结果如下:1H NMR(400MHz,CDCl3)δ12.19(br,1H),8.47(s,1H),4.79-4.55(m,2H),4.30(t,J=6.8Hz,1H),2.01(t,J=7.0Hz,2H),1.82-1.69(m,4H),1.60-1.50(m,2H),1.42-1.11(m,22H),0.77(t,J=7.0Hz,3H);.HRMS(FT-ICRMS)calcd for C19H37NO5P(M-H):390.2415,found:390.2419.
经结构鉴定所合成的化合物确为目标化合物O-二乙基膦酰基-N-十二烷酰基丝氨酸(见结构式I-d)。
润滑脂制备实施例1:
原料组份:500SN基础油1032g(100℃粘度为11mm2/s);氢氧化锂10.33g;十二羟基硬脂酸129.42g;2,6-二叔丁基对甲酚15g;石油磺酸钡11g;二烷基二硫代氨基甲酸盐(T323)10g;含磷化合物I-a 10g。
先将688克基础油和129.42克十二羟基硬脂酸加入制脂釜中,混合均匀,温度升至60-90℃时加入氢氧化锂水溶液92.97克(其中含氢氧化锂10.33克、水82.64克)进行皂化反应50-120min;升温至120-180℃进行脱水反应,脱完水后加入2,6-二叔丁基对甲酚15克并继续升温至190-220℃进行高温炼制5-20min;加入344克基础油降温至100-120℃,加入石油磺酸钡11g、二烷基二硫代氨基甲酸盐10g、含磷化合物I-a 10g,搅拌均匀,通过三辊机研磨2-3次成脂。
润滑脂制备实施例2:
原料组份:500SN基础油1031g(100℃粘度为11mm2/s);氢氧化锂11.28g;十二羟基硬脂酸141.18g;含2,6-二叔丁基对甲酚15g;石油磺酸钡11g;二烷基二硫代氨基甲酸盐(T323)10g,含磷化合物I-b 10g。
先将680克基础油和141.18克十二羟基硬脂酸加入制脂釜中,混合均匀,温度升至60-90℃时加入氢氧化锂水溶液101.52克(其中含氢氧化锂11.28克、水90.24克)进行皂化反应50-120min;升温至120-180℃进行脱水反应,脱完水后加入2,6-二叔丁基对甲酚15克并继续升温至190-220℃进行高温炼制5-20min;加入340克基础油降温到100-120℃,加入石油磺酸钡11g、二烷基二硫代氨基甲酸盐10g、含磷化合物I-b 10g,搅拌均匀,通过三辊机研磨2-3次成脂。
润滑脂制备实施例3:
原料组份:PAO10基础油787g(100℃粘度为10mm2/s);氢氧化锂6.37g;十二羟基硬脂酸79.47g;2,6-二叔丁基对甲酚12g;石油磺酸钡7g;二烷基二硫代氨基甲酸盐(T323)8g,含磷化合物I-c 8g。
先将528克基础油和79.47克十二羟基硬脂酸加入制脂釜中,混合均匀,温度升至60-90℃时加入氢氧化锂水溶液57.09克(其中含氢氧化锂6.37克、水50.72克)进行皂化反应50-120min;升温至120-180℃进行脱水反应,脱完水后加入2,6-二叔丁基对甲酚12克并继续升温至190-220℃进行高温炼制5-20min;加入264克基础油降温到100-120℃,加入石油磺酸钡7g、二烷基二硫代氨基甲酸盐8g、含磷化合物I-c 8g,搅拌均匀,通过三辊机研磨2-3次成脂。
润滑脂制备实施例4:
原料组份:PAO4 801g(100℃粘度为3.9mm2/s);氢氧化锂5.67g;十二羟基硬脂酸70.77g;2,6-二叔丁基对甲酚12g;石油磺酸钡7g;二烷基二硫代氨基甲酸盐(T323)8g,含磷化合物I-d 8g。
先将534克基础油和70.77克十二羟基硬脂酸加入制脂釜中,混合均匀,温度升至60-90℃时加入氢氧化锂水溶液50.79克(其中含氢氧化锂5.67克、水45.12克)进行皂化反应50-120min;升温至120-180℃进行脱水反应,脱完水后加入2,6-二叔丁基对甲酚12克并继续升温至190-220℃进行高温炼制5-20min;加入267克基础油降温到100-120℃,加入石油磺酸钡7g、二烷基二硫代氨基甲酸盐8g、含磷化合物I-d 8g,搅拌均匀,通过三辊机研磨2-3次成脂。
润滑脂制备对比例1:
原料组份:500SN基础油1032g(100℃粘度为11mm2/s);氢氧化锂10.33g;十二羟基硬脂酸129.42g;2,6-二叔丁基对甲酚15g;石油磺酸钡11g;二烷基二硫代氨基甲酸盐(T323)10g;对比生物降解剂(D-1)10g。
先将688克基础油和129.42克十二羟基硬脂酸加入制脂釜中,混合均匀,温度升至60-90℃时加入氢氧化锂水溶液92.97克(其中含氢氧化锂10.33克、水82.64克)进行皂化反应50-120min;升温至120-180℃进行脱水反应,脱完水后加入2,6-二叔丁基对甲酚15克并继续升温至190-220℃进行高温炼制5-20min;加入344克基础油降温至100-120℃,加入石油磺酸钡11g、二烷基二硫代氨基甲酸盐10g、对比生物降解剂(D-1)10g,搅拌均匀,通过三辊机研磨2-3次成脂。
分别对上述制备实施例和对比例的润滑脂进行了滴点、锥入度、氧化安定性、钢网分油、铜片腐蚀、极压性能、铜片腐蚀、防腐蚀性能和降解性能的评定试验,试验方法分别为GB/T3498、GB/T269、SH/T0325、SH/T0324、SH/T0202、GB/T7326、GB/T5018、OECD302B,试验结果见表1。
表1
Claims (22)
2.按照权利要求1所述的润滑脂,其特征在于,其中R1为C5-C25的烃基,R2为H或C1-C8的烷基,R3为单键或C1-C8的亚烃基,R4为H或C1-C4的烷基,R5为单键或C1-C8的亚烷基,R6为单键或C1-C8的亚烷基,R7为H、C1-C10的烷基、C3-C8的环烷基或C6-C10的芳基。
3.按照权利要求1所述的润滑脂,其特征在于,其中R1为C8-C20的烃基,R2为H或C1-C6的烷基,R3为单键或C1-C4的亚烷基,R4为H或C1-C3的烷基,R5为单键或C1-C6的亚烷基,R6为单键或C1-C6的亚烷基,R7为H、C1-C8的烷基、C3-C8的环烷基或C6-C8的芳基。
5.按照权利要求4所述的润滑脂,其特征在于,其中R1为C5-C25的烃基,R2为H或C1-C8的烷基,R3为单键或C1-C8的亚烃基,R4为H或C1-C4的烷基,R5为单键或C1-C8的亚烷基,R6为单键或C1-C8的亚烷基。
6.按照权利要求4所述的润滑脂,其特征在于,其中R1为C8-C20的烃基,R2为H或C1-C6的烷基,R3为单键或C1-C4的亚烷基,R4为H或C1-C3的烷基,R5为单键或C1-C6的亚烷基,R6为单键或C1-C6的亚烷基。
7.按照权利要求4所述的润滑脂,其特征在于,所述磷源选自磷氧卤化合物、磷卤化合物、磷氧化合物、磷酸、亚磷酸、磷酸缩合物和亚磷酸缩合物中的一种或多种。
8.按照权利要求7所述的润滑脂,其特征在于,所述磷氧卤化合物选自磷氧氟化合物、磷氧氯化合物、磷氧溴化合物和磷氧碘化合物中的一种或多种,所述磷卤化合物选自磷氟化合物、磷氯化合物、磷溴化合物和磷碘化合物中的一种或多种、所述磷氧化合物选自P2O5和/或P2O3。
9.按照权利要求4所述的润滑脂,其特征在于,所述磷源选自二甲基膦酰氯、二乙基膦酰氯、二苯基膦酰氯、二环己基膦酰氯、三氯氧磷、二氯乙基磷酸、二氯甲基磷酸、二甲基氯化膦、二乙基氯化膦、二丁基氯化膦、二苯基氯化膦、二环己基氯化膦、二苯基溴化膦、三氯化膦、三氟化膦、三溴化膦、三碘化膦、五氧化二磷、三氧化二磷、磷酸、亚磷酸和多聚磷酸中的一种或多种。
11.按照权利要求10所述的润滑脂,其特征在于,所述R7为H、C1-C10的烷基、C3-C8的环烷基或C6-C10的芳基。
12.按照权利要求10所述的润滑脂,其特征在于,所述R7为H、C1-C8的烷基、C3-C8的环烷基或C6-C8的芳基。
15.按照权利要求4所述的润滑脂,其特征在于,所述反应中加入催化剂,所述催化剂为有机胺,所述催化剂的加入量为所述磷源质量的10%~300%。
16.按照权利要求1-15之一所述的润滑脂,其特征在于,以润滑脂总重量为基准,所述含磷化合物占润滑脂总质量的0.01%~10%;所述稠化剂占润滑脂总质量的3%-40%;所述润滑基础油构成润滑脂的主要成分。
17.按照权利要求1-15之一所述的润滑脂,其特征在于,以润滑脂总重量为基准,所述含磷化合物占润滑脂总质量的0.1%-5%;所述稠化剂占润滑脂总质量的5%-30%。
18.按照权利要求1-15之一所述的润滑脂,其特征在于,所述稠化剂为锂基稠化剂、复合锂基稠化剂、钙基稠化剂、无水钙基稠化剂、复合钙基稠化剂、复合锂钙基稠化剂、钠基稠化剂、复合钠基稠化剂、钡基稠化剂、复合钡基稠化剂、复合铝基稠化剂、聚脲稠化剂、膨润土稠化剂、烃基稠化剂中的一种或多种。
19.按照权利要求1-15之一所述的润滑脂,其特征在于,所述润滑脂中还加入抗氧剂、防锈剂和极压抗磨剂中的一种或多种,所述抗氧剂占润滑脂总质量的0.1%-20%;所述防锈剂占润滑脂总质量的0.01%-15%;所述极压抗磨剂占润滑脂总质量的0.01%-15%。
20.按照权利要求1-15之一所述的润滑脂,其特征在于,所述润滑脂中还加入抗氧剂、防锈剂和极压抗磨剂中的一种或多种,所述抗氧剂占润滑脂总质量的0.2%-10%;所述防锈剂占润滑脂总质量的0.02%-10%;所述极压抗磨剂占润滑脂总质量的0.1%-10%。
21.按照权利要求1-15之一所述的润滑脂,其特征在于,所述润滑脂中还加入抗氧剂、防锈剂和极压抗磨剂中的一种或多种,所述抗氧剂选自酚类和/或胺类抗氧剂;所述防锈剂选自磺酸盐;所述极压抗磨剂选自氨基硫代酯和/或二烷基二硫代氨基甲酸盐。
22.一种润滑脂的制备方法,包括:将权利要求1-21之一中所述的稠化剂、全部或部分的添加剂、全部或部分的润滑基础油在180-230℃恒温炼制,冷却,加入剩余的添加剂、剩余的润滑基础油,研磨成脂。
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