CN102120804B - 聚合物的改进方法 - Google Patents

聚合物的改进方法 Download PDF

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CN102120804B
CN102120804B CN201010611614.5A CN201010611614A CN102120804B CN 102120804 B CN102120804 B CN 102120804B CN 201010611614 A CN201010611614 A CN 201010611614A CN 102120804 B CN102120804 B CN 102120804B
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CN102120804A (zh
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C·J·布斯
C·沃特森
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Infineum International Ltd
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Abstract

本发明涉及聚合物的改进方法，其中三元共聚物为包含式I结构单元、式II结构单元和式IIIa或式IIIb结构单元以及任选式VII结构单元的高聚物。所述聚合物改进来自石油源、尤其是来自植物或动物源的燃料油的低温性能。

Description

聚合物的改进方法
技术领域
本发明涉及对改进燃料油的低温性能有效的聚合物和含所述聚合物的燃料油组合物。
背景技术
燃料油无论得自石油还是植物源，都含有在低温下倾向于作为大片状晶体或蜡球晶沉淀的组分，例如正烷烃或正链烷酸甲酯，这样使得形成导致燃料丧失其流动能力的凝胶结构。燃料仍流动的最低温度称作倾点。
当燃料的温度下降并达到倾点时，在通过管和泵输送燃料中出现困难。另外，形成的蜡晶在倾点以上的温度下倾向于堵塞燃料管、筛网和过滤器。这些问题为本领域熟知的，已推荐多种添加剂用于抑制燃料油的倾点，其中许多为商业用途。类似地，已推荐其他添加剂且为商业用途，用于降低形成的蜡晶的大小并改变其形状。由于它们可能很少堵塞过滤器，更小尺寸的晶体是理想的。来自柴油燃料的蜡，其主要为烷烃蜡，和在植物衍生的燃料中的正链烷酸甲酯结晶成片晶。某些添加剂抑制这种情况并导致蜡采取针状晶体惯态，所得针比片晶更可能通过过滤器，或在过滤器上形成多孔晶体层。其他添加剂也可具有将蜡晶保留在燃料悬浮液中的效果，这样降低沉降，因此还有助于防止堵塞。
本发明基于对改进燃料油的低温性能有效的某类三元共聚物和更高元共聚物的发现。发现该聚合物可用于任何类型的燃料中，但当用于衍生自植物或动物源的燃料油如包含脂肪酸烷基酯的燃料油和这些油与石油衍生的燃料油的混合物中时特别有效。这些油通常称作生物柴油或生物燃料，通常为脂肪酸甲酯(FAME)。
发明内容
根据第一个方面，本发明提供一种包含式I结构单元、式II结构单元和式IIIa或式IIIb结构单元以及任选式VII结构单元的聚合物：
其中R1和R2相同或不同，且各自表示C8-C22烷基、优选C12-C16烷基；
其中R3表示-OCOR6，-COOR15，-COOH或C1-C22烷基、优选C1-C12烷基，且R6表示C1-C22烷基、优选C1-C12烷基；其中R4为氢、-COOH或-CH2COOR16；其中R15和R16相同或不同，且各自表示C8-C22烷基、优选C12-C16烷基；其中R5为氢或甲基；其中X表示式IV、式V或式VI的基团：
其中R7表示氢或C1-C8烷基，R8表示C1-C8烷基，m为1-10的整数，且n为1-30、优选5-20的整数；其中R9为C1-C8烷基连接基，R10、R11和R12相同或不同且各自表示氢或C1-C8烷基，p为1-10的整数，且q为0或1-10的整数；且其中Y表示式IV的基团，其中R7表示氢或C1-C8烷基，R8表示C1-C8烷基，m为1-10的整数，且n为1-30、优选5-20的整数；
其中R13表示C8-C22烷基、优选C12-C16烷基；且其中R14为氢或甲基。
具体实施方式
烷基R1和R2可为线性或支化的，但优选线性的。优选R1和R2相同且各自表示线性C12-C14烷基。在优选的实施方案中，R1和R2各自为线性C12烷基。
优选R3表示-OCOR6。
烷基R6可为线性的，或如果为C3或更大，则可为支化的。优选R6表示C1-C8烷基，在优选的实施方案中，R6为甲基。
当存在时，烷基R15和R16可为线性或支化的，但优选为线性的。当存在时，优选R15和R16相同且各自表示线性C12-C14烷基。在优选的实施方案中，当R15和R16存在时，它们各自为线性C12烷基。
优选R4为氢。
在优选的实施方案中，R3表示-OCOR6，其中R6为甲基，且R4为氢。在另一实施方案中，R3表示-OCOR6，其中R6为2-乙基己基，且R4为氢。
在优选的实施方案中，X表示式IV的基团。优选R7为氢，R8为甲基，m为1-6的整数，例如1、2或3，且n为6-18的整数，例如9、10、11、12、13、14、15或16。
在另一优选实施方案中，X表示式V的基团。优选R9为C2烷基连接基，R10和R11均为甲基，且q为0。
优选Y表示式IV的基团，其中R7为氢，R8为甲基，m为1-6的整数，例如1、2或3，且n为6-18的整数，例如9、10、11、12、13、14、15或16。
当存在式VII结构单元时，烷基R13可为线性或支化的，但优选为线性的。优选R13表示线性C12-C16烷基，例如线性C12烷基或线性C14烷基。
聚合物可包含其他结构单元，但优选聚合物仅包含式I、II、IIIa和/或IIIb的结构单元，或聚合物仅包含式I、II、IIIa和/或IIIb和VII的结构单元。
在优选的实施方案中，聚合物包含式I、II和IIIa的结构单元，其中X表示式IV的基团。
在更优选的实施方案中，聚合物由式I、II和IIIa的结构单元组成，其中X表示式IV的基团。
在另一优选实施方案中，聚合物包含式I、II和IIIb的结构单元。
在更优选的实施方案中，聚合物由式I、II和IIIb的结构单元组成。
在另一优选实施方案中，聚合物包含式I、II和IIIa的结构单元，其中X表示式V的基团。
在更优选的实施方案中，聚合物由式I、II和IIIa的结构单元组成，其中X表示式V的基团。
在另一优选实施方案中，聚合物包含式I、II、IIIb和VII的结构单元。
在更优选的实施方案中，聚合物由式I、II、IIIb和VII的结构单元组成。
存在于聚合物中的各结构单元的比例可变化。优选聚合物将包含5-80摩尔％、更优选20-60摩尔％的式I单元。
优选聚合物将包含5-70摩尔％、更优选10-50摩尔％的式II单元。
当IIIa单元存在时，优选聚合物将包含5-60摩尔％、更优选10-50摩尔％的式IIIa单元。
当式IIIb单元存在时，优选聚合物将包含5-70摩尔％、更优选10-60摩尔％的式IIIb单元。
当式VII单元存在时，优选聚合物将包含10-50摩尔％、更优选15-40摩尔％的式VII单元。
通过GPC相对聚苯乙烯校准标样测定，聚合物的数均分子量(Mn)优选为500-50,000，更优选500-35,000，最优选1,000-20,000；例如5,000-15,000。
聚合物可通过已知方法制备。合适的方法为使用合适单体和自由基引发剂的溶液相聚合。任何合适的溶剂可用于聚合。已经发现环己烷、甲基乙基酮(MEK)、甲苯和乙醇都有效。已经发现过氧新戊酸叔丁酯为合适的自由基引发剂，但是替代物对于本领域熟练技术人员是已知的。
给聚合物提供式I结构单元的合适单体的非限定性实例包括富马酸二烷基酯，例如富马酸二-十二烷基酯和富马酸二-十四烷基酯。给聚合物提供式II结构单元的合适单体的非限定性实例包括乙烯基酯，例如乙酸乙烯酯、2-乙基己酸乙烯酯和新癸酸乙烯酯；衣康酸烷基酯和衣康酸二烷基酯；马来酸；和1-链烯。给聚合物提供式IIIa结构单元的合适单体的非限定性实例包括聚(亚烷基二醇烷基醚)丙烯酸酯或聚(亚烷基二醇烷基醚)甲基丙烯酸酯，例如聚(乙二醇甲基醚)丙烯酸酯和聚(乙二醇甲基醚)甲基丙烯酸酯；丙烯酸二烷基氨基烷基酯或甲基丙烯酸二烷基氨基烷基酯，例如丙烯酸二甲基氨基乙酯和甲基丙烯酸二甲基氨基乙酯。给聚合物提供式IIIb结构单元的合适单体的非限定性实例包括二-聚(亚烷基二醇烷基醚)富马酸酯，例如二-聚(乙二醇甲基醚)富马酸酯。给聚合物提供式VII结构单元的合适单体的非限定性实例包括丙烯酸烷基酯和甲基丙烯酸烷基酯，例如丙烯酸十二烷基酯和甲基丙烯酸十四烷基酯。
根据第二个方面，本发明提供一种包含主要量燃料油和次要量根据第一方面的聚合物的燃料油组合物。
根据第三个方面，本发明提供根据第一方面的聚合物在改进燃料油的低温性能中的用途。
燃料油
燃料油可例如为石油基燃料油，尤其是中间馏分燃料油。这种馏分燃料油通常在110-500℃，例如150-400℃的范围内沸腾。
本发明适用于所有类型的中间馏分燃料油，包括宽沸点馏分，即具有90-20％，如根据ASTM D-86测定50℃或更大的沸点温度差的那些。
燃料油可包含常压馏分或真空馏分、裂解气油或任何比例的直程和热和/或催化裂解的馏分的混合物。最常用的石油馏分燃料为煤油、喷气燃料、柴油燃料、燃用油和重质燃料油。燃用油可为直馏常压馏分，或还可含有真空气油或裂解气油或二者。燃料还可包含主要量或次要量得自费-托方法的组分。也称作FT燃料的费-托燃料包括描述为天然气合成油燃料、煤和/或生物质转变燃料的那些。为了制备这种燃料，首先产生合成气(CO+H2)，然后通过费-托方法将其转化成一般烷烃和烯烃。然后可将一般烷烃通过方法如催化裂解/重整或异构化、加氢裂解和加氢异构化改性以得到多种烃如异烷烃、环烷烃和芳族化合物。所得FT燃料本身可以使用或可与其他燃料组分和如在本说明书中提到的那些燃料类型组合使用。
本发明特别适用于含由得自动物或植物材料的油制备的脂肪酸烷基酯的燃料油，通常称作生物燃料或生物柴油。生物燃料被认为燃烧时很少损害环境且由可再生源得到。已报告在燃烧时，其比相等量石油馏分燃料如柴油燃料形成更少的二氧化碳，且形成非常少的二氧化硫。
得自动物或植物材料的油的实例为菜子油、芫荽油、豆油、棉子油、葵花油、蓖麻油、橄榄油、花生油(peanut oil)、玉米油(maize oil)、杏仁油、棕榈仁油、椰子油、芥子油、麻风树油、牛脂和鱼油。其他实例包括得自玉米(corn)、黄麻、芝麻、牛油树坚果、花生(ground nut)和亚麻子油的油，并可通过本领域已知的方法由其得到。菜子油为用甘油部分酯化的脂肪酸的混合物，其可大量得到且可以简单方法通过压榨而由菜籽得到。循环油如厨房废油也是合适的。
作为脂肪酸烷基酯，可考虑例如如下商业混合物：具有12-22个碳原子的脂肪酸，例如月桂酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、油酸、反油酸、岩芹酸、蓖麻酸、桐酸、亚油酸、亚麻酸、花生酸、顺式9-二十碳烯酸、二十二烷酸或芥酸的乙基酯、丙基酯、丁基酯以及尤其是甲基酯，其碘值为50-150，尤其是90-125。具有特别有利性能的混合物为主要包含，即包含至少50重量％具有16-22个碳原子和1、2或3个双键的脂肪酸甲基酯的那些。优选的脂肪酸烷基酯为油酸、亚油酸、亚麻酸和芥酸的甲基酯。
所述种类的商业混合物例如通过动物和植物脂肪及油的裂解和酯化，由它们与低级(约C1-C6)脂族醇的酯交换得到。对于脂肪酸烷基酯的制备，有利的是由含低水平的饱和酸(小于20％)且碘值小于130的脂肪和油开始制备。如下酯或油的混合物是合适的，例如菜籽、葵花、芫荽、蓖麻、大豆、花生、棉籽、牛脂等。基于某些具有大于80重量％的具有18个碳原子的不饱和脂肪酸的菜子油品种的脂肪酸烷基酯特别合适。
尽管以上油都可用作生物燃料，但优选植物油衍生物，其中特别优选的生物燃料为菜子油、棉子油、豆油、葵花油、橄榄油或棕榈油的烷基酯衍生物，尤其优选菜子油甲基酯。
本发明适用于纯生物燃料。因此，在一个实施方案中，燃料油包含基本100重量％得自植物或动物源的油，优选基本100重量％脂肪酸烷基酯，最优选脂肪酸甲基酯。
生物燃料通常与石油衍生的油组合使用。本发明还适用于任何比例的生物燃料和石油衍生燃料的混合物。这种燃料通常称作Bx燃料，其中x表示生物燃料-石油混合物中生物燃料的重量百分数。实例包括其中x为2或以上，优选5或以上，例如达10、25、50或95的燃料。优选这种Bx燃料中生物燃料组分包含脂肪酸烷基酯，最优选脂肪酸甲基酯。
燃料油，无论是石油还是植物或动物衍生的，优选具有低硫含量。通常，燃料油的硫含量将小于500ppm(重量份/百万重量份)。优选，燃料油的硫含量将小于100ppm，例如小于50ppm。具有甚至更低硫含量，例如小于20ppm或小于10ppm的燃料油也合适。
存在于燃料油中的聚合物的量可根据燃料油的类型和燃料油所需的低温性能变化。适当地，聚合物将以基于燃料油重量计为10-5,000重量ppm，优选10-1,000重量ppm，更优选50-500重量ppm的量存在于燃料油中。
如本领域已知，燃料添加剂通常以包含一种或多种燃料添加剂在合适的载体流体或溶剂中的添加剂浓缩物的形式提供。根据第四个方面，本发明提供一种包含根据第一个方面的聚合物和与其相容的溶剂或载体的添加剂浓缩物。合适的溶剂和载体流体的实例为本领域已知的，包括烃溶剂如石脑油、煤油、柴油和取暖用油，芳族烃如在“SOLVESSO”商品名下出售的那些，醇，醚和其他含氧化合物和链烷烃如己烷、戊烷和异链烷烃。载体流体或溶剂根据它与聚合物和燃料油的相容性选择。
本发明聚合物可直接或以添加剂浓缩物的形式提供给燃料油。
发现本发明聚合物也可作为流动改进剂或倾点下降剂用于润滑油中。
其他添加剂
能改变燃料油低温性能的其他添加剂可与本发明聚合物组合。合适的材料为本领域熟练技术人员已知的那些，包括流动改进剂，例如乙烯-不饱和酯共聚物和三元共聚物，例如乙烯-乙酸乙烯酯共聚物、乙烯-2-乙基己酸乙烯酯共聚物和乙烯-新癸酸乙烯酯共聚物、乙烯-乙酸乙烯酯-2-乙基己酸乙烯酯三元共聚物、乙烯-乙酸乙烯酯-新壬酸乙烯酯三元共聚物、乙烯-乙酸乙烯酯-新癸酸乙烯酯三元共聚物；梳状聚合物如富马酸酯-乙酸乙烯酯共聚物；烃聚合物如氢化聚丁二烯共聚物、乙烯/1-链烯共聚物，和类似的聚合物。合适的还有本领域作为抗蜡沉降添加剂(WASA)已知的添加剂。合适的还有缩合物品种如EP 0 857 776 B1所述的烷基苯酚甲醛缩合物，或如EP-A-1 482 024所述的羟基-苯甲酸酯甲醛缩合物。
本发明考虑这种其他添加剂的加入；它们以本领域熟练技术人员已知的处理率(treat rate)施用。在优选实施方案中，本发明聚合物与乙烯-不饱和酯共聚物、抗蜡沉降添加剂、烷基苯酚甲醛缩合物或羟基苯甲酸酯甲醛缩合物中的一种或多种结合或组合使用。在更优选的实施方案中，本发明聚合物与乙烯-不饱和酯共聚物、抗蜡沉降添加剂，和烷基苯酚甲醛缩合物或羟基苯甲酸酯甲醛缩合物之一或二者结合或组合使用。特别优选的乙烯-不饱和酯共聚物为乙烯-乙酸乙烯酯共聚物、乙烯-乙酸乙烯酯-2-乙基己酸乙烯酯三元共聚物、乙烯-乙酸乙烯酯-新壬酸乙烯酯三元共聚物和乙烯-乙酸乙烯酯-新癸酸乙烯酯三元共聚物。特别优选的抗蜡沉降添加剂为通过邻苯二甲酸酐与两摩尔比例的二氢化牛油脂肪胺反应形成的酰胺-胺盐。可将任何其他添加剂单独引入第一方面的燃料油组合物中或与本发明聚合物组合引入第四方面的添加剂浓缩物中。
现在将仅举例描述本发明。
聚合物的制备
以下实施例说明本发明所用聚合物的合成。同一方法用于制备所有其他聚合物。
将富马酸二-十二烷基酯(15.40g，34.01毫摩尔)、乙酸乙烯酯(1.87g，21.72毫摩尔)和数均分子量为454gmol-1的聚(乙二醇甲醚)丙烯酸酯(3.27g，7.20毫摩尔)与环己烷(10ml)一起放在Schlenk管中。将混合物脱气，然后在氮气气氛下搅拌加热至80℃。将过氧新戊酸叔丁酯(0.1ml，在环己烷中50∶50重量％)加入混合物中以引发聚合反应。在接下来的4小时过程中，每小时将额外引发剂加入混合物中。当经过5个小时后，使混合物冷却并得到产物。
下表1详述了使用以下单体制备的聚合物：
表1
注释：PEGOMeA＝Mn为454的PEGOMeA单体；PEGOMeA＝Mn为804的PEGOMeA单体；(--.--)＝以毫摩尔表示的各单体的使用量；cyhex＝环己烷；MEK＝甲基乙基酮；EtA＝乙醇；tol＝甲苯
测试所制聚合物的CFPP(冷滤点)性能。CFPP为评估燃料油样品在降低的温度下流过过滤器的能力的标准工业试验。设计通过详细描述于“Jn.Of the Institute of Petroleum”，第52卷，第510期(1996)，第173-285页中的程序进行的试验以与汽车柴油中的中间馏分的冷流相关。简言之，将待测试的油样品(40cm3)在保持在约-34℃的浴中冷却以得到约1℃/min的线性冷却。定期地(从浊点以上开始，以每1℃)，使用试验装置测试油在指定时间期间流过细网的能力，所述试验装置为其下端连接有倒漏斗的吸移管，所述倒漏斗位于待测试油的表面以下。具有12mm直径确定的面积的350目筛网铺展在漏斗口上。周期性试验通过将真空施加在吸移管上端而引起，由此油通过筛网被向上吸进吸移管中，直至表示20cm3油的标记。在每次成功通过以后，油立即返回CFPP管中。温度每降低一度，重复该试验，直至油在60秒内不能充满吸移管，出现失败时的温度报告为CFPP温度。
下表2显示聚合物在生物柴油燃料油中的CFPP性能，所述生物柴油燃料油为75∶25重量的菜子油甲基酯(RME)和豆油甲基酯(SME)的混合物。未处理燃料的CFPP为-11.0℃。在还含有乙烯-乙酸乙烯酯共聚物、抗蜡沉降添加剂和羟基苯甲酸酯甲醛缩合物的添加剂配制剂中测试聚合物，其中抗蜡沉降添加剂为通过邻苯二甲酸酐与两摩尔比例的二氢化牛油脂肪胺反应形成的酰胺-胺盐。各栏给出对于所示本发明聚合物处理率测得的平均CFPP值，所述处理率基于燃料油的重量以重量ppm(wppm)给出。在没有值显示时，这表示没有进行测量。
表2

Claims (22)

1.一种包含式I结构单元、式Ⅱ结构单元和式Ⅲa或式Ⅲb结构单元以及任选式VⅡ结构单元的聚合物：
其中R1和R2相同或不同，且各自表示C8-C22烷基；其中R3表示-OCOR6，
-COOR15，-COOH或C1-C22烷基，且R6表示C1-C22烷基；其中R4为
氢、-COOH或-CH2COOR16；其中R15和R16相同或不同，且各自表示
C8-C22烷基；其中R5为氢或甲基；其中X表示式Ⅳ、式V或式Ⅵ的
基团：
其中R7表示氢或C1-C8烷基，R8表示C1-C8烷基，m为1-10的整数，
且n为1-30的整数；其中R9为C1-C8烷基连接基，R10、R11和R12相同
或不同且各自表示氢或C1-C8烷基，p为1-10的整数，且q为0或1-10
的整数；且其中Y表示式Ⅳ的基团，其中R7表示氢或C1-C8烷基，R8
表示C1-C8烷基，m为1-10的整数，且n为1-30的整数；
其中R13表示C8-C22烷基；且其中R14为氢或甲基。
2.根据权利要求1的聚合物，其中R1和R2相同或不同，且各自表示C12-C16烷基。
3.根据权利要求1的聚合物，其中R3表示C1-C12烷基。
4.根据权利要求1的聚合物，其中R6表示C1-C12烷基。
5.根据权利要求1的聚合物，其中R15和R16相同或不同，且各自表示C12-C16烷基。
6.根据权利要求1的聚合物，其中在对X定义的式Ⅳ的基团中，n为5-20的整数。
7.根据权利要求1的聚合物，其中在对Y定义的式Ⅳ的基团中，n为5-20的整数。
8.根据权利要求1的聚合物，其中，R13表示C12-C16烷基。
9.根据权利要求1的聚合物，其中R1和R2相同，且各自表示线性C12-C14烷基。
10.根据权利要求1的聚合物，其中R3表示-OCOR6。
11.根据权利要求10的聚合物，其中R6为甲基或2-乙基己基，且R4为氢。
12.根据权利要求1-11中任一项的聚合物，其中X表示式Ⅳ的基团。
13.根据权利要求12的聚合物，其中R7为氢，R8为甲基，m为1-6的整数，且n为6-18的整数。
14.根据权利要求1-11中任一项的聚合物，其中X表示式V的基团。
15.根据权利要求14的聚合物，其中R9为C2烷基连接基，R10和R11均为甲基，且q为0。
16.根据前述权利要求1-11中任一项的聚合物，其中Y表示式Ⅳ的基团，其中R7为氢，R8为甲基，m为1-6的整数，且n为6-18的整数。
17.根据前述权利要求1-11中任一项的聚合物，其包含式Ⅶ结构单元。
18.根据权利要求17的聚合物，其中R13表示线性C12-C16烷基。
19.一种包含主要量燃料油和次要量根据前述权利要求1-18中任一项的聚合物的燃料油组合物。
20.根据权利要求19的燃料油组合物，其中所述燃料油包含由得自动物或植物材料的油制备的脂肪酸烷基酯。
21.根据权利要求1-18中任一项的聚合物在改进燃料油的低温性能中的用途。
22.一种包含根据权利要求1-18中任一项的聚合物和与其相容的溶剂或载体的添加剂浓缩物。
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