CN1033036C - 琥珀酐衍生物的制备方法 - Google Patents

琥珀酐衍生物的制备方法 Download PDF

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CN1033036C
CN1033036C CN89105497A CN89105497A CN1033036C CN 1033036 C CN1033036 C CN 1033036C CN 89105497 A CN89105497 A CN 89105497A CN 89105497 A CN89105497 A CN 89105497A CN 1033036 C CN1033036 C CN 1033036C
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威廉姆·达恩伯格
亨德里克·迪杰门
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Abstract

制备基本上不含氯的聚烯烃取代的琥珀酐的方法，其中，琥珀基对聚烯烃链的平均摩尔比大于1.3/1，该方法包括将聚烯烃与过量-摩尔的马来酸酐一起加热，聚烯烃含有至少70%的具有α-烯键结构的端基和/或与该α-烯键结构相平衡的结构的端基。

Description

琥珀酐衍生物的制备方法
本发明涉及琥珀酐衍生物的制备，更具体地说，本发明涉及可转化成对调入润滑油具有良好性能的添加剂的聚烯烃取代的琥珀酐的制备，以及上述转化和使用。
聚烯烃-琥珀酸衍生物是已得到充分确认的润滑油用的分散添加剂，这种类型的分散剂由于没有金属成分，因此常称之为无灰分散剂。这些衍生物是通过聚烯烃与马来酸酐反应，然后与某种多醇或多胺反应来制取的。第一步聚烯烃与马来酸酐反应常常是在氯的存在下进行的，这可以缩短反应时间，并更有效地利用聚烯烃。氯既可以直接引入，一也可以在与马来酸酐反应之前通过将聚烯烃氯化来实现。这些“氯”路线的一个后果是，最终产物中不可避免有残留氯。残留氯的量不大，一般在1000～5000ppm(百万分之几)范围内，从实用和商业观点看，这样的量如今还是完全可以接受的。但是，环境保护增大压力，要求润滑油添加剂基本上不含氯，而采用由氯路线制得的聚烯烃-琥珀酸衍生物却不易满足这个指标。
与“氯”路线不同的另一条路线是所谓的“热”路线，在该路线中，使聚烯烃和马来酸酐一起加热，反应也可以在有催化剂存在的情况下进行。这种方法避免了氯残余物[除非氯残留物以杂质形式存在于反应剂和催化剂(如果使用)中]，但是会使反应不合适地变慢，聚烯烃转化率较低，还会导致生成非所要求量的焦油状副产物(通常称之为“Polymala”)。热路线的另一个缺陷是，难以制得其中琥珀基成分的摩尔比明显过大的聚烯烃-琥珀酸衍生物。
如今发现，琥珀基对聚烯烃的比例超过1.3/1，适宜的是至少为1.5/1时，可以生成润滑油用无灰分散剂，这种分散剂对分散发动机操作时所产生的烟灰，具有较高的效率，而且还可以改善油的粘度指数。但是，“热”方法容易产生比例低于1.3/1的产物。因此，需要有一种使产物所含琥珀基和聚烯烃二成分的比例超过1.3的“热”方法。
现在已经发现，聚烯烃中的端基结构影响所得产物的琥珀基对聚烯烃的比例。作为说明，聚异丁烯的端基一般主要有以下几种：
Figure C8910549700051
     (顺/反异构现象反式IIIA)
Figure C8910549700052
按照本发明，意外地发现，“热”方法可以制得以前用该法达不到的琥珀基含量的产物，其条件是聚烯烃反应剂含有高比例的α-烯键端基(例如以上的结构I)或含有与该含α-烯键基相平衡的端基(例如以上的结构II)。由于这个发现，从而开辟了制得基本上不含残留氯的和琥珀基与聚烯烃的比例又合乎需要的高的聚烯烃琥珀酸衍生物的可能性。此外，由于选择这种聚烯烃反应剂还可达到高的转化率，因此得到仅含少量剩余的未转化聚烯烃的产物。
因此本发明提供了一种制备基本上不含氯和琥珀基对聚烯烃链的平均摩尔比大于1.3/1的聚烯烃取代的琥珀酐的方法，该方法包括将聚烯烃与至少过量一摩尔的马来酸酐(即马来酸酐与聚烯烃的摩尔比至少为2∶1)一起加热，其特征在于，聚烯烃中具有α-烯键结构的端基和/或与该α-烯键结构相平衡的结构(它的互变异构体)的端基至少占70％。
这种聚烯烃宜从一种或多种含2～6个碳原子的烯烃单体制得，优选的是聚异丁烯。聚烯烃的端基正如所指出那样，应保证有至少70％的具有α-烯键结构和/或与它相平衡的互变异构体结构。在聚异丁烯的情况下，α-烯键结构是指上面I所示的结构，已经发现，结构II是与它相平衡的结构。另外，还发现，当聚烯烃中含端基α-双键的那些基团占端基主要的单一成分时，琥珀基对聚烯烃的比例通常可达到最高；因此，本发明的一个推荐实施方案中是，使这种聚烯烃同马来酸酐一起加热。优选的情况是，聚烯烃里的端基α-双键基至少要占端基的40％，最好超过50％，而除了含α-烯键或与它相平衡的端基之外的端基，具体说聚异丁烯(结构IV)占所有总的端基的量宜低于25％。聚烯烃的分子量(按数均分子量测定)适宜在600～5000的范围内，以750～2500为佳，又以850～2100为更佳。聚异丁烯产品满足这些条件，故适用于本发明方法，它的市售牌号是“Ultravis”。
马来酸酐与聚烯烃热反应的详细操作条件在先有技术中已经完全确定，其实例见英国专利1483729号。所用的反应温度一般高于150℃，以在180～250℃的范围内为佳，又以195～230℃为更佳。该反应原则上可在常压下进行，但由于马来酸酐的沸点约为200℃(不同出处引用值为198℃和202℃)，优选的反应温度是在该沸点的左右或略高于沸点。该反应常适宜于在高压釜中进行，此时，压力将是超计大气压，例如至少为2巴，而且可高达30巴。
如上所述，马来酸酐的用量，按聚烯烃计算，至少为摩尔过量。其过量的实际程度当然取决于最终产物所要求的琥珀基对聚烯烃的比例。实际上，马来酸酐摩尔过量一般最好大于1.5，又以至少是2为佳(即马来酸酐与聚烯烃的摩尔比至少为3∶1)。利用这样的反应条件，加上选用含必要端基的聚烯烃，已发现可制得聚烯烃取代的琥珀酐，其中琥珀基对聚烯烃链的平均摩尔比大于1.5/1，以至少达1.7/1为佳，与此同时，聚烯烃的转化率可达85～90％。
加入催化剂可提高反应速度(由此缩短了反应时间)和/或减少副产物生成，不过，使用催化剂与否不是最重要的，有时如果要求最终产物完全不含金属成分或杂质，加入催化剂甚至会是有害的。需要的话，本发明的方法可以在诸如石油溶剂这样的溶剂存在下进行，此见英国专利1483729号。
用本发明方法制得的聚烯烃取代的琥珀酐(本身或其盐的形式)已直接用来作润滑剂和燃料组成物的添加剂，例如按美国专利3346354号或欧洲专利0207560号所述的方法作燃料添加剂，按美国专利3288714号所述的方法作润滑剂组成物的分散剂/清净剂。但是，这些酐主要是用来通过与多醇或胺反应为制备聚烯烃琥珀酯或琥珀酰亚胺作中间体。这些产物用作润滑剂添加剂具有优异的性能。
为了生成这类酯，取代的琥珀酐宜与多醇反应，例如二元醇，如乙二醇、1，2-二羟基丙烷、1，3-二羟基丙烷、二羟基丁烷以及二羟基戊烷，三元醇，如丙三醇、三羟基丁烷以及三羟基戊烷，和高级醇，如丁糖醇、戊五醇以及己糖醇。优选的聚烯烃琥珀酸酯是用含三个或更多个羟基的多元醇制得的，诸如丙三醇，季戊四醇，甘露糖醇，以及三羟甲基丙烷。
为了制取琥珀酰亚胺衍生物，取代的酐宜与含至少一个＝NH(仲氨基)的胺反应，这种胺可以是线性或支化的亚烷基多胺，环脂基多胺，或杂环多胺。
适用于制备本发明琥珀酰亚胺反应产物的支化多胺包括式I的那些胺
Figure C8910549700091
其中R是C2-4的亚胺基，X为0～7，Y为1～7，Z为0～7，X＋Y＋Z为1～8。
环脂基多胺宜从五元或六元环体系选择，诸如环戊烷或环己烷环。氨基可以直接与环相连接，也可以是环被氨烷基取代。一种适用的环多胺是1，4-二氨基环己烷。适用的杂环多胺是被一个或多个氨基、式II的氨烷基所取代的四氢吡啶和二氢吡啶、哌啶、氮杂环丁烷、吡咯、哌嗪。式II为
        H2N-(R-NH)w-R           II其中，W为0～5，R是C2-4的亚烷基。特别推荐的是N-(2-氨基乙基)哌嗪和1，4-二(2-氨基乙基)哌嗪。
适用于制备本发明琥珀酰亚胺反应产物的线性多胺包括亚乙基多胺，而且还包括α-，γ-二氨基丙烷或丁烷、亚丙基多胺、二(三亚甲基)三胺以及亚丁基多胺。特别推荐的是亚乙基多胺，诸如二亚乙基三胺，三亚乙基四胺，四亚乙基五胺以及五亚乙基六胺。这类化合物宜通过一种亚烷基氯化物与氨反应或用亚乙基亚胺与例如氨反应制取。这些反应结果形成亚烷基多胺的混合物，包括诸如哌嗪这样的环状产物。
这种多胺最好具有由-[N(R2)-R1]a-和/或
Figure C8910549700101
组成的结构作高分子链节，由-R1-NR2R3和/或
Figure C8910549700102
组成的结构作分子链的端基，其中R1是亚乙基、亚丙基、三亚甲基或亚丁基，R2和R3是氢或-R1-NH2，a为0～7，b为1～3。
聚烯烃琥珀酸酯或酰亚胺也可按本专业领域熟练技术人员熟知的方法进行后处理(如见英国专利1565627号)，例如，通过与硫或磷衍生物反应，或尤其通过与诸如硼的氧化物或酸这样的硼衍生物反应。
与获得良好性能润滑剂添加剂特别有关的是三亚乙基四胺和四亚乙基五胺，以及含这些产物的工业混合物。取代的琥珀酐与多醇或多胺之间的反应条件，在先有技术中已完全确定，用这种酯或琥珀酰亚胺作润滑油的组分构成了本发明的又一个方面。
本发明的润滑剂组成物包括润滑油和润滑脂，不过，它们多半是润滑油。本发明的润滑油组合物是基于天然和合成润滑油以及它们的混合物。这些润滑剂包括曲柄箱润滑油，用于点燃式和压燃式内燃机，诸如汽车和卡车发动机，船用和火车用柴油机。在自动传动液、传动轴润滑剂，齿轮润滑油、金属加工润滑剂、液压液以及其它润滑油和润滑油脂组成物中加入本发明的聚烯烃-琥珀酸衍生物也可能是有益的。
天然油包括动物油和植物油(如蓖麻油、猪脂油)以及矿物油，例如石油，溶剂处理或酸处理过的石蜡型、环烷型或石蜡-环烷混合型的矿物润滑油。从煤或页岩得到的润滑粘性油也是有用的基剂油。合成润滑油包括烃油和卤代烃油，诸如：聚合的烯烃和共聚烯烃(如聚丁烯、聚丙烯、丙烯-异丁烯共聚物、氯代聚丁烯等)；聚(1-己烯)，聚(1-辛烯)，聚(1-癸烯)等及其混合物；烷基苯(如十二烷基苯、十四烷基苯、二壬基苯、二(2-乙基己基)苯等)；多苯(如联苯、三联苯、烷基多苯等)；烷基联苯醚，烷基联苯硫醚和衍生物、同型物以及它们的同系物。
本发明还进一步通过下面的实施例来加以说明，其中马来酸酐(MALA)和两种不同品级的聚异丁烯(PIB)，即“Hyvis-10”或“Ultravis-10”，进行热偶联。不同品级的PIB，它们的数均分子量均约为950，但是产物的主要区别在于各种端基结构的比例。参照前面标明的结构I-V，这些产物的端基结构用核磁共振波谱分析初步测定如下(数值为摩尔％)。
  样     品      I  II   III  IIIA   IV  IVA   V   其它
“Hyvis”-10     3   0   16   44     21   5    0    11
“Ultravis”-107 4  10    1    2      5   0    3     5
理所当然，不同批号的产品，精确的数值可以会有变化，不过异构体的基本数值将是类似的。
MALA与“Hyvis”PIB之间的反应是在超计大气压的高压釜中进行，详细的反应条件列于后面的表I，其中还列出了制得产物中每个PIB分子链所含的琥珀基数目以及聚马来酸酐副产物的量。
详细的反应条件与产物的产率及其酸值一起在下面加以叙述。参数用来作为计算每个聚烯烃分子链中琥珀基数目的基础(每个聚异丁烯分子链中MALA基团的数目)，前提是所有的酸基都来自琥珀残基。
实施例1
将641份“Ultravis”10(Mn＝950)预热到165℃。加入190份马来酸酐之后，反应温度在15分钟内升到19℃。四小时后温度逐渐升到200～203℃，反应继续进行20小时。将在不同反应阶段取得的样品和最终产物通过在160℃和减压下加热，脱去MALA。
用过滤或水提取的方法除去焦油状的副产物。
纯化的最终产物含91％(重量)的聚异丁烯琥珀酐，酸值为2.77毫克当量H+/克。这相当于每个聚异丁烯分子链中MALA基的平均数目为1.75。
实施例2
将641重量份(pbw)“Uleravis 10”(Mn＝950)和190份马来酸酐(MALA)在60分钟内加热到约198℃(MALA的沸点)。约六小时后，使温度逐渐升高到200～203℃，使反应继续进行18小时。粗产物通过在160℃和减压下加热，脱去未反应的MALA。用过滤或提取的方法除掉焦油状副产物。过滤出的最终产物含有90％(重量)的聚异丁烯琥珀酸酐，酸值为2.77毫摩尔/克。这相当于每个聚异丁烯分子链中MALA基的平均数目为1.7。另外，产物提取的结果是除掉了2.2％(重量)的焦油状副产物，这样纯化后的产物的酸值基本不变。
实施例3
将510重量份的“Ultravis 10”(Mn＝950)和106份马来酸酐在60分钟内加热到约198℃(MALA的沸点)。约六小时后，把反应温度逐渐升到204～206℃，并继续反应18小时。粗产物通过在160℃和减压下加热，脱除未反应的MALA。过滤除去焦油状副产物。纯化的最终产物含有84％(重量)的聚异丁烯琥酸酐，其酸值为2.40毫摩尔/克。这相当于每个聚异丁烯链中MALA基的平均数目为1.6。
实施例4
将234重量份“Ultravis 75”(M＝2000)和34份马来酸酐在60分钟内加热到约198℃(MALA的沸点)。约六小时之后，把温度逐渐升高到204～206℃，继续进行反应18小时。粗产物通过在160℃和减压下加热，脱去未反应的MALA。用过滤和水提取的方法除掉焦油状副产物。纯化的最终产物含有79％(重量)的聚异丁烯琥珀酸酐，酸值为1.23毫摩尔/克。这相当于每个聚异丁烯分子链中MALA基的平均数目为1.7。
实施例5
将“Ultravis 10”和马来酸酐(摩尔比1∶3)置于高压釜中，于230℃反应4.5小时。除去过量的MALA和焦油状副产物之后，得到的偶合产物的活性物质含量为89％(重量)，酸值为2.77毫摩尔/克。这相当于每个PIB含MALA基的数目为1.7。
实施例6
将含氯量为7.2ppm的3154重量份“Ultravis 10”(M＝920)预热到大约75℃。加入1010份马来酸酐(MALA)之后，把反应混合物在55分钟内加热到约198℃(MALA的沸点)。约三小时之后，使反应温度逐渐升高到200～202℃，七小时后升高到204～206℃。总反应时间24小时后，纯化的最终产物(除去过剩的MALA和焦油状副产物后)含有91％(重量)的聚异丁烯琥珀酐，酸值为2.98毫摩尔/克。这相当于每个聚异丁烯分子链中MALA基的数目为1.8。产物含氯量为4.0ppm。
实施例7
实施例5的粗产物经脱除过剩的MALA之后冷却到约160℃，并用“HVI60”油(一种高粘度指数的基油，其粘度在100℃约为4×10-3泊)稀释。在混入20克“Decalite”(主体加料助滤剂)之后，产物在约140℃通过一个预先涂有“Decalite”的压滤器过滤。纯化的烷基琥珀酐再进一步与三亚乙基四胺(TETA)反应，琥珀酐基与TETA的摩尔比为2/1。反应在180℃进行四小时之后，产物通过预涂“Decalite”的压滤器过滤纯化。纯化的二琥珀酰亚胺分散剂的活性物质含量为44％(重量)，含氮量为1.56％(重量)，含氯量为3.6ppm。
对照实施例1
将1000重量份“Hyvis 10”(Mn＝980)和300份马来酸酐在60分钟内加热到温度约198℃(MALA的沸点)，约六小时之后，使温度逐渐升高到200～203℃，继续进行反应18小时。粗产物通过在160℃和减压下加热，脱除未反应的MALA。过滤除去焦油状副产物。纯化的最终产物含有82％(重量)的聚异丁烯琥珀酐，酸值为1.91毫克分子/克。这相当于每个聚异丁烯分子链中MALA基的平均数目为1.3。
对照实施例2
将“Hyvis 10”与马来酸酐(摩尔比1∶3)置于高压釜中，于215℃反应24小时。把反应不同阶段所取样品以及最终产物脱除掉过剩的MALA，过滤除掉焦油状副产物。反向结果(表I)表明，即使在反应24小时之后，每个PIB中所含MALA基的平均数目不超过1.1。
表1反应时间    压力       酸    值       活性物质     每个PIB中(小时)      (巴)     (毫克分子/克)    (重量％)     琥珀基数目2          3           0.88           48.4         1.004          4           1.18           64.4         1.006          5           1.35           70.6         1.057          6           1.43           73.4         1.0524         15           1.68           83.9         1.10
实施例8
碳黑分散性试验
在本试验中，将3％(重量)的碳黑加入润滑油组成物中，并测定它在60℃的运动粘度(用乌别罗德粘度计)。粘度明显的提高表明工作性能差。看来，这种比较简单的试验的结果同柴油机曲柄箱润滑油中分散性性能的等级很好地一致。英国Rail Publica-tion ER 669：1984对该试验作了说明。
所用的组成物是一种SAE I5 W40中东润滑油，其中按工业整套配方含有一种二烷基二硫代磷酸锌、一种高碱性的烷基水扬酸钙以及VI改进剂。往这种组成物样品中加入1％(重量/重量)的聚烯烃琥珀酰亚胺产品(由“Hyvis”和“Ultravis”制得)。用所得的组成物进行碳黑分散性试验(用3％(重量)的“Cabot Carbon Elftex 460”作碳黑)，测试结果示于表2。
表2
产物                        粘度的提高(％)
由“Hyvis”制得                 198.0
由“Ultvavis”制得              133.9
实施例9
在高压釜中，使“Uitravis 75”(Mn＝2000)与马来酐(MALA)(摩尔比1/3)于235℃反应8小时。除去过剩的MALA之后，按照实施例7中的方法，用“HVI 60油”稀释粗反应产物，然后过滤。纯化的产物含有47％(重量)的聚异丁烯琥珀酐，其酸值为0.68毫摩尔/克。这相当于每个聚异丁烯分子链中MALA基的平均数目为1.5。
接着使纯化的聚异丁烯琥珀酐与四亚乙基五胺(TEPA)反应，琥珀酐基对TEPA的摩尔比为2∶1。180℃下反应四小时后，使产物通过“Decalite”过滤。纯化的二琥珀酰亚胺清净剂的活性物质含量为50％(重量)，氮含量为1.16％(重量)。
对照实施例3
在高压釜中，使“Hyvis 75”(Mn＝1900)与马来酸(摩尔比1∶3)于235℃反应六小时。除去过剩的MALA之后，用“HVI 60油”稀释粗反应产物，然后过滤(按照实施例7中的方法)。纯化的产物含有53％(重量)的聚异丁烯琥珀酐，其酸值为0.58毫摩尔/克。这相当于每个聚异丁烯分子链中MALA基的平均数目为1.1。
接着使纯化的聚异丁烯琥珀酐与四亚乙基五胺(TEPE)进一步反应，琥珀酐基对TEPE的摩尔比为2∶1。180℃下反应四小时后，使产物通过“Decalite”过滤。纯化的二琥珀酰亚胺清净剂的活性物质含量为47％(重量)，氮含量为0.81％(重量)。
实施例10
连续VE发动机试验
将对照实施例3和实施例9基于“Hyvis 75”和“ULTRAVIS 75”的产物(为溶于矿物油中的浓缩物，规定量为2.5％(重量)的试验产物)各与含有约12％(重量/重量)配合添加剂(additive package)的SAE 10w/60润滑油掺合。配合添加剂系按整套配方配制而成，其由一种高碱性水杨酸盐清净剂、一种粘度改进剂、一种锌基抗磨添加剂和一种聚甲基丙烯酸酯降凝剂组成。然后，按照“连续V E试验法”(7th draft，1988年5月19日；ASTM Monitoring Center，4400 5th Avenue Pittsbu-rgh USA)对所得的油进行了评价。
为了比较，对市购产品“SAP 220”(Shell)和LZ6418(Lubrizol)进行了类似的评价。市购产品与本发明产品的区别在于，市购产品含有少量的残余氯。
VE试验所得的结果示于下表，表中还有衍生各产品的诸反应剂的性质和相对比例。
用以下的常规项目表示发动机试验结果。
RACS＝摇捍复盖淤渣
AES＝平均发动机淤渣
PSV＝活塞裙漆膜
AEV＝平均发动机漆膜
按0～10级度量形成淤渣和漆膜的程度，10级表示形成的淤渣或漆膜为0。
                表3产品               衍生物             发动机试验
           PIB/
           MALA
           摩尔
      PIB  当量  胺    偶合比 RACS AES PSV AEV
      MnSAP 220   950  1.0  TETA    2.0    3.0 7.0 6.3 4.0LZ 6418   约   约   TEPA    约     7.0 8.8 6.7 5.1
      1850 1.7           2组合物实施例3   1900 1.1  TEPA    2.0    4.5 5.2 6.8 5.8实施例9   1900 1.5  TEPA    2.0    9.0 9.1 7.1 5.8

Claims (7)

1.制备基本上不含氯的聚烯烃取代的琥珀酸衍生物的方法，所述琥珀酸衍生物以琥珀酐，琥珀酰亚胺或琥珀酯形式存在，其中，琥珀基对聚烯烃链的平均摩尔比大于1.3/1，该方法包括将聚烯烃与摩尔过量的马来酸酐一起加热，其特征在于：聚烯烃含有至少70％的具有α-烯键结构的端基和/或与该α-烯键结构相平衡的结构的端基，以形成琥珀酐，选择性地接着将制得的酐与含至少一个＝NH基的胺或多醇反应，分别生成聚烯烃取代的琥珀酰亚胺或琥珀酯。
2.根据权利要求1的方法，其中聚烯烃的至少50％的端基含有α-烯键，和不到25％的端基具有不同于α-烯键的结构或与它相平衡的结构。
3.根据权利要求1或2所述的方法，其中聚烯烃是聚异丁烯。
4.根据权利要求1或2的方法，其中聚烯烃的数均分子量在750-2500范围内。
5.根据权利要求1或2的方法，其中所选择的马来酸/聚烯烃的摩尔比和聚烯烃的组成要使制得的产物中琥珀基对聚烯烃链的平均摩尔比高于1.5∶1。
6.根据权利要求5所述的方法，其中摩尔比至少为1.7∶1。
7.根据权利要求1或2所述的方法，其中反应温度在180-250℃范围内。
CN89105497A 1988-08-05 1989-08-02 琥珀酐衍生物的制备方法 Expired - Fee Related CN1033036C (zh)

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AU614168B2 (en) 1991-08-22
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BR8903909A (pt) 1990-03-27
JP2919861B2 (ja) 1999-07-19
EP0355895B1 (en) 1994-12-14
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