CN1064972C - 燃料或润滑油添加剂、其制备方法以及含有这些添加剂的燃料或润滑油组合物 - Google Patents

燃料或润滑油添加剂、其制备方法以及含有这些添加剂的燃料或润滑油组合物 Download PDF

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CN1064972C
CN1064972C CN951930362A CN95193036A CN1064972C CN 1064972 C CN1064972 C CN 1064972C CN 951930362 A CN951930362 A CN 951930362A CN 95193036 A CN95193036 A CN 95193036A CN 1064972 C CN1064972 C CN 1064972C
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fuel
hydrogen
different
lubricating oil
additive
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CN1147821A (zh
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K·奥本兰德
J·莫尔
H-J·默勒
D·波塞尔特
W·冈瑟
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BASF SE
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Abstract

描述了以由含3-24个碳原子的一种或多种1-链烯和由0-50%(重)乙烯制得的乙烯式不饱和聚-1-链烯为基础的燃料或润滑油添加剂，它们的制备方法以及含有这些添加剂的燃料或润滑油组合物。

Description

燃料或润滑油添加剂、其制备方法以及含有 这些添加剂的燃料或润滑油组合物
本发明涉及以有极性端基的长链烃基为基础的燃料和润滑油添加剂；用于制备这些添加剂的无卤素的一步法，其中极性反应物在长链烯烃的双链处进行自由基加成反应；以及含有这些添加剂的燃料和润滑油组合物。
汽油发动机的汽化器和进气体系以及汽油和柴油发动机中计量燃料的注射体系被各种杂质的污染越来越严重，这些杂质由空气中的尘埃颗粒、来自燃烧室未燃烧的烃类残留物以及进入汽化器的曲轴箱排出气产生。
在空转过程中和在较低负荷范围内，这些残留物改变了空气／燃料比，以致混保物变得更富油，使燃烧变得更不完全，反过来使废气中未燃烧的或部分燃烧的烃类的比例变得更大以及汽油消耗增加。
为了避免这些缺点，使用燃料添加剂来使阀门和曲轴箱或注射体系保持清洁是已知的(例如参见，M．Rossenbeck in Katalysatoren，Tenside，Mineraloladditive，ed．J．Falbe and U．Hasserodt，page 223，G．ThiemeVerlag，Stuttgart 1978)。
视作用方式以及这些清净添加剂作用的优选位置而定，今天在两代添加剂之间有差别。
第一代添加剂仅能防止在进气体系中生成沉积物，但不能除去已存在的沉积物，而现在的第二代添加剂可达到这两个目的(保持清洁和清洗作用)，特别是由于它们有极好的热稳定性，在相当高的温度段，如在进气阀中可做到这一点。
这些添加剂作为清净剂的分子结构原理一般来说可认为是极性结构与主要是高分子量非极性或亲油性基团键合。
第二代添加剂常常以有非极性部分的聚异丁烯为基础制得。在这里，聚异丁胺型添加剂是特别值得注意的。
这样的添加剂主要用两种多步合成法由聚异丁烯制得。
第一种方法包括起始聚合结构氯化，随后用胺或优选氨进行起始聚合结构的亲核取代。该法的缺点除为两步合成外，还有就是使用氯，从而产生含氯或含氯化物的产物，今天这些产物不再是希望的。
在第二种方法中，聚异丁胺用甲酰化随后还原胺化的方法由聚异丁烯制得，也就是说也是两步法，它也需要适当的次级结构(infrastructure)。
所以，简单的一步无氯合成清净剂和分散剂或两种性能相结合的化保物的方法具有技术上和经济上的意义，而且这些方法可在标准的设备中实现。
GB-A-1383423公开了一种制备可用作汽化器清净剂的烷基多胺的方法。在这里，至少有15个碳原子的α-烯烃与多胺在自由基引发剂存在下反应。所用的α-烯烃特别优选聚异丁烯。
EP-B-0342792公开了一种制备有硫醚官能基的聚丁烯，在该法中有机硫醇与每一分子有一个碳碳双键和数均分子量为200-1000的聚丁烯在能生成自由基的条件下反应。
本发明的一个目的是提供适合作燃料或润滑油添加剂的化合物，而且这些化合物可用技术上不复杂的一步无氯合成法制得。
我们已发现，这一目的可用这样的燃料或润滑油添加剂实现，这些添加剂通过乙烯属不饱和的聚-1-链烯(由一种或多种有3-24(优选3-10，特别优选3-6)个碳原子的1-链烯烃和由0-50％(重)乙烯制得)与a)通式I的化合物和／或b)通式II的化合物的反应制得，
Figure 9519303600051
Figure 9519303600052
式中，X为O或NR7；R1为CN、COOH、C(O)OR9、C(O)O(O)CR6、CONR6R7、C(O)R9、C(S)R9、CHO、CH(NR6R7)R6、SCR6R7R8、NR7R9或OR6；R2和R3为相同的或不同的，都为R1、氢或不同的有机基团；R4和R5为相同的或不同的，都为氢、OR9、NR7R8或未取代的或取代的(环)烷基或芳基；R6、R7和R8为相同的或不同的，都为氢或有机基团；R9为与氢不同的有机基团；以及R1-R9中至少两个基团可为环的一部分。
此外，本发明还涉及一种制备这些燃料或润滑油添加剂的方法，其中由3-24(优选3-10，特别优选3-6)个碳原子的1-链烯烃和由0-50％(重)乙烯得到的聚-1-链烯在自由基引发剂存在下，在能生成自由基的条件下与a)通式I的化合物和／或b)通式II的化合物反应，以及涉及它们在燃料或润滑油组合物中的应用，特别是用于内燃发动机。
在本发明的一优选实施方案中，使用的乙烯属不饱和聚-1-链烯是由3-24个碳原子的一种或多种1-链烯和由0-50％(重)乙烯制得的数均分子量为100-15000的聚烯烃或低聚烯烃。其中特别优选的是数均分子量为150-5000特别优选250-1000的聚异丁烯，它们由异丁烯和0-30％(重)正丁烯得到，例如可按DE-A-2702604制得。
在另一优选的实施方案中，有末端双键含量为至少95％优选至少98％的聚-1-链烯被使用，例如可在金属茂催化剂存在下通过单体结构块(monomer building blocks)的聚合或低制得。
本发明使用的，由3-24个碳原子的一种或多种1-链烯烃和由0-50％乙烯制得的聚-1-链烯(优选聚-1-正构链烯)例如可在通式III的金属茂催化剂存在下和在有机铝化合物优选铝氧烷作为助催化剂存在下，1-链烯特别是1-正构链烯聚合来制得
CpmMXnYr    III式中，Cp为未取代的环戊二烯基单元和／或单C1-C4烷基环戊二烯基单元，M为锆或铪原子，配体X为氢化物和／或卤素离子和／或甲基，相对于铝氧烷助催化剂，使用的催化剂其M／Al原子比为1∶250至1∶1000，以及使用的温度为5-110℃，压力30-100bar。
催化剂III为茂锆和茂铪，包括四价锆和铪的络合物，其中金属原子M以类夹心的方式键联在两个未取代的和／或C1-C4单烷基取代的环戊二烯基CP之间，中心原子M的剩余价被氢化物和／或卤素离子和／或甲基饱和。特别适用于新方法的茂锆和茂铪催化剂是环戊二烯基未取代的茂锆和茂铪。氟、氯、溴和／或碘离子可作为卤素离子键联到金属原子上。
适合的催化剂的例子是CP2ZrF2、CP2ZrCl2、CP2ZrCl2、CP2ZrI2、CP2ZrCl、CP2Zr(CH3)Cl、CP2Zr(CH3)2、CP2HfF2、CP2HfCl2、CP2HfBr2、CP2HfI2、CP2HfHCl、CP2Hf(CH3)Cl、CP2Hf(CH3)2。
优选的是，只一种催化剂用于低聚，但使用不同催化剂的混合物也是可能的。优选的配体X为氯化物、氢化物和甲基，锆特别优选作为催化剂III的中心原子M。环戊二烯基未取代的式CP2ZrCl2的氯化茂锆特别优选用作催化剂。
可用已知的方法以简单的方式合成这些催化剂，例如Brauer编辑的Handbuch der Praparativen Anorganischen Chemie，Volume 2，3rdedition，pages 1395 to 1397，Enke，Stuttgart 1978。
使用的助催化剂是有机铝化合物，优选铝氧烷。铝氧烷在有机铝化合物部分水解中形成，例如通式AlR3、AlR2Y和AlR2Y3的有机铝化合物，其中R例如为C1-C10烷基，优选C1-C5烷基；C3-C10环烷氧基，C7-C12芳烷基或烷芳基和／或苯基或萘基以及Y可为氢；卤素，优选氯或溴；或C1-C10烷氧基，优选甲氧基或乙氧基。可用各种方法进行这样的有机铝化合物的部分水解，例如DE-A-3240383或EP-A-0268214的方法。生成的含氧的铝氧烷通常是不相同的化合物，而为通式IV的低聚物混合物
Figure 9519303600071
式中，通常n为6-20，R有上述含义。如果有不同R基团的有机铝化合物或其混合物被水解，那么就生成有不同R基团的铝氧烷，也可用作助催化剂。但是优选的是，铝氧烷用作助催化剂。优选的铝氧烷是甲基铝氧烷。因为由于其制备方法，优选用于作助催化剂的铝氧烷不是相同的化合物，铝氧烷溶液的克分子浓度基于其铝含量。
对于聚合来说，催化剂相对助催化剂其M／Al原子比通常为1∶250至1∶1000，优选1∶300至1∶600，特别优选1；400至1∶500。
1-链烯的聚合优选在液相进行，最好使用少量溶剂，优选脂族烃或芳族烃，如苯、甲苯、二甲苯、乙苯、异丙苯、萘、四氢萘、己烷、庚烷、辛烷、异辛烷、壬烷、癸烷、十二烷、环己烷、十氢萘、石油醚或石脑油。特别优选使用的溶剂是甲苯和二甲苯。在这一方法中，溶剂／1-链烯体积比通常为1∶20至1∶500，优选1∶30至1∶200，特别优选1∶40至1∶100，1-链烯的体积在每种情况下基于使用压力下的体积。在使用条件下，1-链烯是液体。聚合通常在50-110℃(优选60-90℃)、30-100bar(优选30-50bar)下进行。对于这一方法，金属茂／1-链烯比通常并不重要，但优选金属茂／1-链烯摩尔比为1∶50至1∶250000，优选1∶70至1∶200000，特别优选1∶90至1∶190000。
聚合可间歇进行如在搅拌高压釜中，或者连续进行如在管式反应器中。通过产物蒸馏分离出催化剂后或用水解随后过滤沉淀的固体分离出催化剂后，反应混合物优选用蒸馏方法处理，如果需要在减压下进行。
在该法中优选用作原料的丙烯可由各种来源得到，如由裂解气体得到，例如由蒸汽裂解装置得到的裂解气体。例如在丙烷脱氢生成的丙烯也可使用。可使用纯丙烯，但也可使用丙烯与在反应条件下为惰性的其他烃类的混合物。
该聚合方法选择性制得有末端双键的聚-1-链烯，特别是高生产率选择性制得丙烯聚合物。
本发明使用的聚-1-链烯，特别是乙烯与1-正构链烯的共聚物也可用其他已知的方法制备，例如在EP-A-0441548中公开的方法。在这里，金属茂催化剂与铝氧烷组合使用。这里使用的金属茂也是式III的环戊二烯基-过渡金属化合物，优选的过渡金属是Ti、Zr和Hf。
如果需要的话在蒸馏以后，可用这一方法制备的聚-1-链烯在新方法中随后可按本身可知的方式进一步反应。
对于新添加的制备来说，聚-1-链烯通常在0-200℃下，在自由基引发剂存在下与通式I和／或II的化合物反应。
上述这些化合物至少在分子骨架中一处，至少有一个氢原子可很容易通过生成自由基中间体而被取出，以致这些化合物的加成反应发生在聚-1-链烯的一个或多个乙烯属双键处。根据本发明，优选的式I和／或II化合物是这些化合物，其中至少一个取代基R4和R5和／或取代基R6和R7中至少一个不是氢。自由基引发剂、自由基的生成以及自由基与乙烯属不饱和化合物的加成反应本身是已知的。这样的自由基加成反应例如在以下公开的出版物中描述：H．-H．Vogel，Synthesis 1970，page 99 etsgq．；Friedmann，Lester，Tetrahedron Letters 1961，238et seq．；Nikishin，Vinogrador，Fedorova，J．C．S．Chem．Commun．1973，693；M．Regitz，B．Giesein Houbenweyl，Methoden der Organischen Chemie，4th edition，Vol．E19a(1989)。
在新型聚-1-链烯与式I和／或II的化合物的反应中，反应条件随所用的原料以及产生自由基的方法变化。但是，反应温度通常为0-200℃。
反应可在无溶剂或有惰性溶剂如脂族或芳族烃的情况下进行。
聚-1-链烯与式I和／或II化合物的摩尔比通常为1∶1至1∶30。但是，聚-1-链烯的乙烯属双键的完全转化是不必要的。在某些情况下，不完全转化甚至是有好处的。
新添加剂的制备例如可用这样的方法进行，在这一方法中，首先将式I和／或II化合物的约三分之二(可能在适合的溶剂中)放在最好有搅拌器、内部温度计、回流冷器和滴液漏斗的多颈烧瓶中，然后在搅拌下，将聚-1-链烯、引发剂和剩余的式I和／或II化合物(可能使用惰性溶剂)的混合物缓慢滴加入。加完后，如果需要，在选择的温度下，将反应混合物再进行搅拌，使反应完全。反应进程可用IR光谱监测，观测约890cm-1处的末端双键的特征吸收带。在除去溶剂和过量的式I和／或II化合物后，通常得到粘稠的无色至淡黄色的反应产物残留物。
在燃料组合物中，特别是内燃发动机的燃料组合物中，新型添加剂的用量优选为10-5000ppm，特别优选100-2000ppm。
在润滑油组合物中，按组合物的总重计，新添加剂的用量优选为0．5-10％(重)，特别优选为1-3％(重)。
由于新添加剂制备方法不同，在新燃料或润滑油中使用的添加剂不含卤素，使它们特别适合用于燃料或润滑油。
由于新添加剂的结构，它们可作为清净剂和分散剂。这就意味着，作为清净剂，它们使阀门和汽化室或注射体系保持清洁。作为分散剂，当它们通过燃烧室进入发动机的润滑油循环后，它们还可改善发动机油中淤渣的分散。
如果主要想利用新添加剂的分散性能，它们也可与传统的清净剂组合作为另外的添加剂。
可在与新添加剂物质作为分散剂的混合物的清净剂组分的产物原则上是任何适合这一用途的已知产物，如在以下文献中描述的：J．Falbe，U．Hasserodt，Katalysatoren，Tenside und Mineraloladditive，G．Thieme Verlag，Stuttgart 1978，page 221 et seg_或K．Owen，Gasoline andDiesel Fuel Additives，John Wiley & Sons，1989，page 23 et seg．．
含氮的清净剂，如含有胺基或酰胺基的化合物是优选使用的。EP-A-0244616的聚异丁胺、EP-A-0188786的亚乙基二胺四乙酰胺和／或亚乙基二胺四乙酰亚胺或EP-A-0244725的聚醚胺是特别适合的，参考在这些专利中的说明。由于它们的制备方法不同，所公开的产物同样有不含氯和氯化物的优点。
如果主要想利用新化合物的清净作用，这些物质还可与载体油组合。这样的载体油是已知的。特别适合的载体油为聚乙二醇基载体油，相应的醚和／或酯，例如在US-A-5004478或DE-A-3838918公开的。有末端烃基的聚亚烷基单醇(US-A-4877416)或DE-A-4142241中公开的载体油也可使用。
加铅的，特别是无铅的普通汽油和优质汽油适合作汽油发动机燃料。这些汽油除烃类以外还含有其他组分，例如醇类如甲醇、乙醇或叔丁醇，以及醚类如甲基叔丁基醚。除了新添加剂外，燃料通常还含有其他添加剂，如缓蚀剂、稳定剂、抗氧剂和／或其他清净剂。
缓蚀剂通常是有机羧酸的铵盐，当原料有适当的结构时，它们有助于形成薄膜。用来降低PH值的胺常常也含在缓蚀剂中。杂环芳烃通常用来防止非铁金属腐蚀。
实施例
1新型添加剂的制备
实施例1
在装有搅拌器、内部温度计、回流冷凝器和滴液漏斗的多颈烧瓶中，首先装入290g吗啉，并加热到回流温度(约130℃)。然后缓慢滴加入引发剂二叔相基过氧化物(5．3g)、500g聚异丁烯(数均分子量1000)和145．8g吗啉的混合物。滴加完后，在130℃下继续搅拌，总计12h，在此期间每次少量地加入共5．3g二叔丁基过氧化物。然后反应混合物与过量的试剂分开。
实施例2-7
步骤同实施例1，不同的是通式I或II不同的化合物和引发剂的用量不同，如表1所示。此外，在每一情况下，将混合物加热到表1所示的温度，在反应和随后的搅拌过程中，都保持这一温度。
表1
实施例 烯烃(mol) 化合物Ⅰ或Ⅱ(mol) 引发剂(mol) 温度℃〕
1 聚异丁烯(1) 丙二酸二乙酯(10) 0.1 140
2 聚异丁烯(1) 异丁醛(2.5) 0.25 160
3 聚异丁烯(1) 吡咯烷酮(10) 0.1 140
4 聚异丁烯(1) 吗啉(10) 0.2 130
5 聚异丁烯(1) 二甲基甲酰胺(5) 0.5 145
6 聚异丁烯(1) 环戊酮(2.5) 0.25 160
7 聚异丁烯(1) 烯丙胺(2.5) 0.1 75
在发动机试验中测试了制备的衍生物作为阈门清净剂的作用。
2．发动机试验
发动机试验根据CECF／04／A／87在1．21Opel Kadett发动机上进行。所用的燃料：欧洲无铅优质汽油。
表2
以下实施例的添加剂 剂量     进气阀沉积量
    阀     1   2   3   4
    1  800    11(542)   8(441)   8(405)   17(623)
    2  800    10(447)   6(262)
    3  800     2(255)   1(155)   2(150)    1(395)
    4  800     0(255)   1(155)   0(150)    0(395)
    5  800     2(255)   3(155)   2(150)    4(395)
    6  800     0(300)   0(168)   2(175)    2(355)
    7  800    12(300)   2(300)   6(300)    2(355)
*括号中的数值：不加添加剂的沉积量；数值不同是由于所用的欧洲无铅优质汽油的差别

Claims (8)

1．一种可用以下步骤制得的燃料或润滑油添加剂，由含3-24个碳原子的一种或多种1-链烯和0-50％(重)乙烯制得的烯属不饱和聚-1-链烯与a)式I的化合物或b)式II的化合物反应制得，
Figure 9519303600022
式中，X为O或NR7；
R1为CN、COOH、C(O)OR9、C(O)O(O)CR6、CONR6R7、C(O)R9、C(S)R9、CHO、CH(NR6R7)R6、SCR6R7R8或OR6；
R2和R3相同或不同，且都可为R1、氢或为不同的有机基团；
R4和R5相同或不同，每一种可为氢、OR9、NR7R8或未取代的或取代的(环)烷基或芳基；
R6、R7和R8相同或不同，都为氢或有机基团；
R9为不同于氢的有机基团；
且R1-R9中的至少两个可为一个环的一部分。
2．根据权利要求1的燃料或润滑油添加剂，其中所用的聚-1-链烯的数均分子量为150-5000。
3．根据权利要求1或2的燃料或润滑油添加剂，其中取代基R4和R5中至少一个不是氢。
4．根据权利要求1或2的燃料或润滑油添加剂，其中取代基R6和R7中至少一个不是氢。
5．一种制备燃料或润滑油添加剂的方法，其中由含3-24个碳原子的一种或多种1-链烯和0-50％(重)乙烯制得的烯属不饱和聚-1-链烯，在自由基引发剂存在下和在能生成自由基的条件下，与a)式I化合物或b)式II化合物反应， 式中，X为O或NR7；
R1为CN、COOH、C(O)OR9、C(O)O(O)CR6、CONR6、C(O)R9、C(S)R9、CHO、CH(NR6R7)R6、SCR6R7R8、NR7R9或OR6；
R2和R3相同或不同，且都可为R1、氢或不同的有机基团；
R4和R5相同或不同，都为氢、OR9、NR7R8或未取代的或取代的(环)烷基或芳基；
R6、R7和R8相同或不同，为氢或有机基团；
R9为与氢不同的有机基团；
且R1-R9中至少一个可为一个环的一部分。
6．含有权利要求1的至少一种添加剂的燃料或润滑油组合物。
7．根据权利要求6的燃料组合物，其中它含有10-5000ppm这种添加剂。
8．根据权利要求6的润滑油组合物，其中按组合物的总重计，它含有0．5-10％(重)这种添加剂。
CN951930362A 1994-04-12 1995-04-05 燃料或润滑油添加剂、其制备方法以及含有这些添加剂的燃料或润滑油组合物 Expired - Fee Related CN1064972C (zh)

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