CN107001535B - 共聚物及其用于降低燃料中的链烷烃晶体结晶的用途 - Google Patents
共聚物及其用于降低燃料中的链烷烃晶体结晶的用途 Download PDFInfo
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- CN107001535B CN107001535B CN201580064323.XA CN201580064323A CN107001535B CN 107001535 B CN107001535 B CN 107001535B CN 201580064323 A CN201580064323 A CN 201580064323A CN 107001535 B CN107001535 B CN 107001535B
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Abstract
本发明涉及一种共聚物,其可通过将以下单体共聚:(A)至少一种不饱和二羧酸或其衍生物,(B)至少一种包含6至20个碳原子的α‑烯烃,(C)至少一种丙烯酸或甲基丙烯酸的C3‑至C20‑烷基酯或这种烷基酯的混合物,和(D)任选地,一种或多种不同于单体(A)、(B)和(C)的其他可共聚单体,随后转化至少一种二烷基胺(E)而获得,所述至少一种二烷基胺(E)的两个烷基基团独立地为具有17至30个碳原子的烷基基团。本发明还涉及一种合成共聚物的方法及其用途,尤其是用于降低燃料中链烷烃晶体结晶的用途。
Description
本发明涉及一种共聚物,其可通过将以下单体共聚并随后与至少一种二烷基胺(E)反应而获得:
(A)至少一种不饱和二羧酸或其衍生物,
(B)至少一种具有至少6至最高达且包括20个碳原子的α-烯烃,
(C)至少一种丙烯酸或甲基丙烯酸的C3-至C20-烷基酯或这种烷基酯的混合物,和
(D)任选地一种或多种除单体(A)、(B)和(C)以外的其他可共聚单体,
其中所述至少一种二烷基胺(E)中的两个烷基基团独立地为具有至少17至最高达30个碳原子的烷基基团。
本发明还涉及一种制备所述共聚物的方法。
本发明还涉及所述共聚物用于改变燃料中链烷烃晶体结晶的用途。
由矿物油得到的化石来源的中间馏分燃料,特别是瓦斯油、柴油或轻质加热用燃料油,根据原油的来源具有不同的链烷烃含量。在低温下,固态链烷烃在浊点(“CP”)下沉淀。在进一步冷却过程中,片状的正链烷烃晶体形成一类“纸牌结构的房子”且中间馏分燃料停止流动,即使其主要部分仍为液体。在浊点和倾点(“PP”)的温度范围内沉淀的正链烷烃显著削弱该中间馏分燃料的流动性;链烷烃阻塞过滤器并对燃烧单元造成不规则或完全中断的燃料供应。在轻质加热用燃料油情况下发生类似的中断。
久为人知的是合适的添加剂可以改变中间馏分燃料中正链烷烃的晶体生长。具有良好效果的添加剂防止中间馏分燃料在比最早结晶出链烷烃晶体的温度低数摄氏度的温度下已经固化。相反,形成细的、易结晶的、分开的链烷烃晶体,这些晶体甚至在温度进一步降低时通过机动车辆和加热系统中的过滤器,或者至少形成可透至中间馏分的液体部分的滤饼,从而确保无中断地操作。流动改进剂的有效性按照欧洲标准EN116通常通过测量冷滤点(“CFPP”)而间接表示。使用的这类冷流改进剂或中间馏分流动改进剂(“MDFI”)长久以来包括例如乙烯-羧酸乙烯酯共聚物如乙烯-乙酸乙烯酯共聚物(“EVA”)。
在生物燃料(例如所谓的“生物柴油”)以及中间馏分燃料和生物燃料油的混合物的情况下,类似地表现出冷流特性的问题。在这里,原则上可以使用与纯中间馏分燃料相同的添加剂来改善冷流特性。
这些添加剂在中间馏分燃料中使用时的一个缺点是,以此方式改变的链烷烃晶体,由于它们与液体部分相比密度更高,在中间馏分燃料的储存过程中在燃料容器(例如储罐)底部具有沉积越来越多的倾向。这导致在容器上部形成均质低链烷烃相,而在底部形成富含链烷烃的双相层。由于在车辆燃料箱和矿物油经销商的储存或供应罐中该燃料通常在容器底部上方不是非常远的地方排出,因此存在高浓度的固态链烷烃将导致过滤器和计量装置堵塞的风险。由于链烷烃的沉淀量随温度降低而增加,因此储存温度越低于该链烷烃的沉淀温度,则该风险越大。特别地,生物柴油馏分也提高了中间馏分燃料的这种不希望的链烷烃沉积倾向。链烷烃分散剂或蜡抗沉降添加剂(“WASA”)的额外使用可以减少所述问题。
WO 95/07944公开了由单烯键式不饱和C4-C6二羧酸或其酸酐、丙烯的低聚物或具有4至10个碳原子的支链1-烯烃的低聚物以及单烯键式不饱和化合物来制备共聚物,然后将它们与胺组分反应。产物被用作燃料中的清洁剂。
EP 1526167A2和EP 1857529A1公开了在马来酸酐与具有10至20个碳原子的α-烯烃的共聚物的混合物中使用EVA共聚物,使其与具有C8-至C16-烷基基团的伯胺或仲胺反应。通过酰胺或酰亚胺键引入胺。α-烯烃的基团和胺的烷基基团的长度必须满足特定的比例以适于作为燃料油的冷流改进剂。
所解决的问题是提供减少中间馏分燃料的这种不希望的链烷烃沉积倾向的产品。
根据本发明,所述问题通过在开始提及的共聚物而解决,所述共聚物由组分(A)、(B)、(C)和任选地(D)和(E)形成。
单体(A)包含至少一种,优选一种至三种,更优选一种或两种且最优选确切地一种不饱和的二羧酸或其衍生物。
衍生物应理解为表示:
-所述酸酐,其为单体或聚合形式,
-单烷基酯或二烷基酯,优选单-C1-C4-烷基酯或二-C1-C4-烷基酯,更优选单甲基酯或二甲基酯或相应地单乙基酯或二乙基酯,
-混合酯,优选具有不同的C1-C4-烷基组分的混合酯,更优选混合的甲基乙基酯,以及
-单酰胺和二酰胺,以及酰亚胺,其可通过不饱和二羧酸与伯胺或仲胺,优选C1-C30-烷基胺或二-C1-C30-烷基胺反应而获得。
所述衍生物优选为单体形式的酸酐或二-C1-C4-烷基酯,更优选单体形式的酸酐。
在另一优选的实施方案中,所述衍生物为二酰胺或单酰胺,优选单酰胺,其可通过不饱和二羧酸与二烷基胺(E)——其中烷基基团独立地具有至少17至最高达30个碳原子——反应而获得。
在本文件的上下文中,C1-C4-烷基应理解为表示甲基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基和叔丁基,优选甲基和乙基,更优选甲基。
所述不饱和二羧酸包括其中两个羧基与烯键式不饱和双键共轭的那些二羧酸或其衍生物。
其实例为马来酸、富马酸、2-甲基马来酸、2,3-二甲基马来酸、2-甲基富马酸、2,3-二甲基富马酸、亚甲基丙二酸和四氢邻苯二甲酸,优选马来酸和富马酸且更优选马来酸,以及其衍生物。
单体(A)特别为马来酸酐。
单体(B)包含至少一种,优选一种至四种,更优选一种至三种,甚至更优选一种或两种,且特别确切地为一种具有至少6个至最高达且包括20个碳原子的α-烯烃。所述α-烯烃(B)优选具有至少8个,更优选至少10个碳原子。所述α-烯烃(B)优选具有最高达且包括18个,更优选最高达且包括16个且最优选最高达且包括14个碳原子。
如果单体(B)为不同烯烃的混合物,则碳原子数的测定应基于混合物中存在的烯烃中碳原子数的统计平均值。因此,50摩尔%的C22烯烃和50摩尔%的C16烯烃的混合物具有19个碳原子的统计平均值。
然而,在一个优选的实施方案中,基本上混合物中存在的所有α-烯烃具有优选至少90摩尔%,更优选至少95摩尔%且最优选至少98摩尔%上述规定量的碳原子。
所述α-烯烃可优选为直链或支链的、优选直链的1-烯烃。
其实例为1-己烯、1-庚烯、1-辛烯、1-壬烯、1-癸烯、1-十一碳烯、1-十二碳烯、1-十三碳烯、1-十四碳烯、1-十五碳烯、1-十六碳烯、1-十七碳烯、1-十八碳烯、1-十九碳烯和1-二十碳烯,其中优选1-癸烯、1-十二碳烯、1-十四碳烯和1-十六碳烯,且特别优选1-十二碳烯。
单体(C)为至少一种,优选一种至四种,更优选一种至三种,甚至更优选一种或两种,且特别确切地为一种丙烯酸或甲基丙烯酸(优选丙烯酸)的C4-至C20-烷基酯,或这种烷基酯的混合物。所述烷基在每种情况下可为直链或支链的。
对于组分(C)而言,合适的丙烯酸或甲基丙烯酸(优选丙烯酸)的C3-至C20-烷基酯优选为丙烯酸和甲基丙烯酸与C3-至C18-链烷醇,优选C4-至C18-链烷醇,更优选C8-至C16-链烷醇,甚至更优选C10-至C14-链烷醇且特别为C12-链烷醇的酯,例如与以下醇的酯:正丙醇、异丙醇、正丁醇、仲丁醇、异丁醇、叔丁醇、正戊醇、叔戊醇、正己醇、正庚醇、正辛醇、2-乙基己醇、正壬醇、异壬醇、正癸醇、2-丙基庚醇、正十一烷醇、异十一烷醇、正十二烷醇、正十三烷醇、异十三烷醇、3,3,5,5,7-五甲基辛醇、正十四烷醇、正十五烷醇、正十六烷醇、正十七烷醇、异十七烷醇、3,3,5,5,7,7,9-七甲基癸醇、正十八烷醇和正二十烷醇。还可以想到的是C17-链烷醇的混合物,如WO 2009/124979所述。
在一个实施方案中,所述链烷醇是根据iso指数,具有1.2至3.0,特别是1.7至2.5的平均支化度的支链C13-链烷醇或C17-链烷醇或其混合物。
这类链烷醇或其混合物可通过C4烃料流的低聚反应,特别是工业级C4料流的均相或非均相催化的低聚反应获得,所述工业级C4料流由10重量%至90重量%的丁烷、10重量%至90重量%直链丁烯(丁烯-1,顺式-丁烯-2和反式-丁烯-2)和1重量%至5重量%的异丁烯组成,例如由萃余液II组成。通常用于此目的的非均相催化剂包含镍。低聚反应通常在30至280℃和10至300巴的压力下进行。这类低聚反应记载于例如WO 99/25668(5)中。低聚产物随后进行加氢甲酰基化和氢化,并由此得到所述的链烷醇或链烷醇混合物。
组分(C)优选为(甲基)丙烯酸正癸酯、(甲基)丙烯酸2-丙基庚酯、(甲基)丙烯酸正十一烷基酯、(甲基)丙烯酸正十二烷基酯、(甲基)丙烯酸正十三烷基酯、(甲基)丙烯酸异十三烷基酯或(甲基)丙烯酸正十四烷基酯,更优选(甲基)丙烯酸正十二烷基酯或(甲基)丙烯酸正十四烷基酯或其混合物,且最优选各自的丙烯酸酯。
任选地其他单体(D)——其不同于单体(A)、(B)和(C)——优选选自脂环族的(甲基)丙烯酸酯(D1)、聚亚烷基二醇单烷基醚的(甲基)丙烯酸酯(D2)、链烷酸乙烯酯(D3)、烯丙基化合物(D4)、乙烯基醚(D5)、N-乙烯基内酰胺(D6)、N-乙烯基咪唑(D7)、烯键式不饱和的芳族化合物(D8)、二氧化硫(D9)和烯键式不饱和腈(D10)。
对于至少一种单体(D)而言,在本文中可以任选地使用优选一种至四种,更优选一种至三种,甚至更优选一种或两种,且特别确切地为一种单体(D)。
脂环族的(甲基)丙烯酸酯(D1)的实例为具有至少一种,优选一种或两种且更优选一种脂环族环体系且具有5至20个碳原子的醇的(甲基)丙烯酸酯。优选的单体为(甲基)丙烯酸环戊酯、(甲基)丙烯酸环己酯和(甲基)丙烯酸降冰片酯,特别优选各自的丙烯酸酯。
聚亚烷基二醇单烷基醚的(甲基)丙烯酸酯(D2)优选为摩尔质量为134至1178的聚-1,2-丙二醇的单-C1-C4-烷基醚的(甲基)丙烯酸酯或摩尔质量为106至898的聚乙二醇的单-C1-C4-烷基醚的(甲基)丙烯酸酯,以及乙二醇单-C1-C4-烷基醚的(甲基)丙烯酸酯或丙二醇单-C1-C4-烷基醚的(甲基)丙烯酸酯。特别优选乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单正丁基醚、1,2-丙二醇单甲基醚、1,2-丙二醇单乙基醚、二乙二醇单甲基醚、二乙二醇单乙基醚和二乙二醇单正丁基醚。
在链烷酸乙烯酯(D3)中,优选乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、戊酸乙烯酯、己酸乙烯酯、2-乙基己酸乙烯酯、辛酸乙烯酯、新癸酸的乙烯酯(“Veova”)、癸酸乙烯酯、十二烷酸乙烯酯、十三烷酸乙烯酯、异十三烷酸乙烯酯、十四烷酸乙烯酯、十五烷酸乙烯酯、十六烷酸乙烯酯和十八烷酸乙烯酯,特别优选乙酸乙烯酯、丙酸乙烯酯、己酸乙烯酯、2-乙基己酸乙烯酯,以及新癸酸的乙烯酯(“Veova”),非常特别优选乙酸乙烯酯。
在烯丙基化合物(D4)中,优选烯丙基醇、烯丙基醇C1-C4-烷基醚和(D3)所列的那些羧酸的链烷酸烯丙基酯。
在乙烯基醚(D5)中,优选环己基乙烯基醚、异丙基乙烯基醚、异丁基乙烯基醚、叔丁基乙烯基醚、正丁基乙烯基醚、辛基乙烯基醚、癸基乙烯基醚、十二烷基乙烯基醚、十四烷基乙烯基醚、十六烷基乙烯基醚和十八烷基乙烯基醚。
N-乙烯基内酰胺(D6)优选为N-乙烯基己内酰胺和N-乙烯基吡略烷酮。
在N-乙烯基咪唑(D7)中,优选N-乙烯基咪唑。
在烯键式不饱和芳族化合物(D8)中,优选苯乙烯和1-甲基苯乙烯,特别优选苯乙烯。
在烯键式不饱和腈(D10)中,优选丙烯腈和甲基丙烯腈,特别优选丙烯腈。
在任选使用的单体(D)中,优选(D1)、(D3)、(D5)和/或(D8),特别优选(D1)、(D3)和/或(D5),非常特别优选(D1)和/或(D3)。
优选选择单体(A)、(B)、(C)和任选地(D)的化学计量,以使共聚形式的单体的摩尔结合比(A)∶(B)∶(C)∶(D)为1∶0.5至2.0∶0.5至2.0∶0至0.1。
优选地,摩尔结合比(A)∶(B)∶(C)∶(D)为1∶0.6至1.5∶0.6至1.5∶0至0.05。
更优选地,摩尔结合比(A)∶(B)∶(C)∶(D)为1∶0.7至1.0∶0.7至1.0∶0。
本发明的共聚物可在第一步中通过聚合单体(A)、(B)、(C)和任选的(D)的混合物来获得。
所述共聚物可通过常规的共聚方法获得,例如溶剂聚合、乳液聚合、沉淀聚合或本体聚合,优选溶剂聚合或本体聚合;它们优选通过所述共聚方法获得。
在第一制备阶段,单体组分可以以其本身(neat)的形式聚合、以乳液或优选以溶液的形式进行聚合。对于各单体组分,在本文中可使用单一的单体种类或几种该单体种类的混合物。聚合反应通常在标准压力和保护性气体(例如氮气)下进行,不过也可例如在高压釜中在最高达25巴的升高的压力下进行。聚合温度通常为50至250℃,特别为90至210℃,尤其是120至180℃,通常为140至160℃。合适的聚合反应器原则上为所有常见的连续或间歇式装置,例如搅拌罐、搅拌级联罐、管式反应器或环管反应器。
通常,聚合由通过自由基机制分解的引发剂引发;适用于此目的的合适的引发剂为空气或有机过氧化物和/或氢过氧化物的氧,以及有机偶氮化合物。有用的有机过氧化物或氢过氧化物的实例包括二异丙苯过氧化氢、异丙苯过氧化氢、甲基异丁基酮过氧化物、二叔丁基过氧化物和过氧化异壬酸叔丁酯。合适的有机偶氮化合物的实例为偶氮二异丁腈(“AIBN”)。此外,在聚合中还可使用合适的链转移剂,例如硫醇、醛或酮。
如果在聚合中还使用溶剂或乳液介质,则常用的高沸点惰性液体适用于此目的,例如脂族烃,如庚烷、D70、白油、灯油;芳族烃,如乙苯、二乙苯、甲苯、二甲苯或相应的工业烃混合物,例如 或溶剂油,以及1,2-环己基二羧酸二烷基酯、优选1,2-环己基二羧酸二异壬基酯。
在第二反应阶段中,将由此可获得的共聚物(优选由此获得的共聚物)与二烷基胺(E)反应。该反应通常不需要任何催化剂;作为替换,该反应可在50至160℃,优选60至140且更优选70至120℃的温度下进行。该反应优选可在惰性溶剂,优选上述用于聚合的溶剂中进行。
所述二烷基胺(E)为至少一种,优选一种或两种且更优选确切地一种二烷基胺(E),其中所述烷基基团各自独立地为具有至少17至最高达30,优选17至26,更优选17至24且最优选17至22个碳原子的烷基基团。
两个烷基基团可相同或不同,优选相同。
具有17至最高达30个碳原子的烷基基团可为直链或支链的,优选直链的,特别优选正十七烷基、正十八烷基、正十九烷基、正二十烷基、正二十一烷基、正二十二烷基、二十四烷基、二十六烷基和三十烷基,且特别优选正十八烷基、正十九烷基和正二十烷基。
优选的二烷基胺(E)为二-正十八烷基胺、二-正十九烷基胺和二-正二十烷基胺。基于共聚物中二羧酸(A)的引入单元计的二烷基胺(E)的摩尔比优选为至少1.2∶1,更优选1.3至2.0∶1,甚至更优选1.5至2.0∶1且特别为2.0∶1。
在优选的实施方案中,二烷基胺理论上以这样的方式使用,将一当量的二烷基胺(E)与共聚物中二羧酸(A)的引入单元反应而形成酰胺基团并且另一当量的二烷基胺(E)中和形成的游离羧基。
在另一实施方案中,如果单体(A)已经以不饱和二羧酸与二烷基胺(E)的二酰胺或单酰胺,优选单酰胺的形式使用,则可省略第二反应阶段。
在这种情况下,由(A)、(B)和(C),以及任选地(D)所形成的共聚物不再需要进行酰胺化,因为单体(A)已经在聚合反应中作为相应的酰胺使用。在这种情况下,存在于由此获得的共聚物中的游离羧基仍可以用二烷基胺(E)中和至20至100摩尔%的程度。
本发明的共聚物在与组分(E)反应后,优选具有2000至20000,更优选2200至8000且最优选2500至6000g/mol的重均分子量(Mw)(在每种情况下通过凝胶渗透色谱测定)。多分散性优选最高达3,更优选2至3。
本发明的共聚物可优选地在燃料中以其功能作为链烷烃分散剂(“WASA”)使用。本发明的共聚物只有在与常见的流动改进剂一起使用时通常才能特别好的发挥其作为石蜡分散剂的作用。
在本发明的上下文中,流动改进剂应理解为表示改善中间馏分燃料的冷特性的所有添加剂。除了现在的冷流改进剂(“MDFI”)以外,还存在成核剂(参见,Ullmann’sEncyclopedia of Industrial Chemistry,第五版,卷A16,第719页及以后)。
当存在冷流改进剂时,除了本发明的共聚物之外,本发明的中间馏分燃料包含的这些冷流改进剂的量通常为1至2000重量ppm,优选5至1000重量ppm,特别为10至750重量ppm且尤其为50至500重量ppm,例如150至400重量ppm。这类冷流改进剂例如记载于WO2007/147753,具体在13页第1行至第16页32行,其通过引用的方式纳入本说明书中。
优选的流动改进剂为如WO 99/29748所述的乙烯-乙酸乙烯酯共聚物或如WO2004/035715所述的梳型聚合物,并与用作链烷烃分散剂的本发明共聚物一起形成用于中间馏分燃料、特别是用于具有一定比例生物柴油的那些有效和通用的冷稳定体系。
更优选地,流动改进剂为乙烯与至少一种另外的烯键式不饱和单体的共聚物,所述烯键式不饱和单体优选选自羧酸烯基酯、(甲基)丙烯酸酯、马来酸二烷基酯、富马酸二烷基酯和烯烃。
最优选地,所述流动改进剂为乙烯和至少一种羧酸烯基酯与至少另一烯键式不饱和单体的三聚物或四聚物,所述烯键式不饱和单体优选选自(甲基)丙烯酸酯、马来酸二烷基酯、富马酸二烷基酯和烯烃。
合适的烯烃为例如具有3至10个碳原子并具有1至3个,优选具有1或2个,特别是具有一个碳碳双键的那些。在后一种情况下,所述碳碳双键可位于末端(α-烯烃)或中间。然而,优选α-烯烃,特别优选具有3至6个碳原子的α-烯烃,例如丙烯、1-丁烯、1-戊烯和1-己烯。
合适的(甲基)丙烯酸酯为例如(甲基)丙烯酸与C1-至C10-链烷醇的酯,特别是与以下醇的酯:甲醇、乙醇、丙醇、异丙醇、正丁醇、仲丁醇、异丁醇、叔丁醇、戊醇、己醇、庚醇、辛醇、2-乙基己醇、壬醇和癸醇。
合适的羧酸烯基酯为例如具有2至20个碳原子的羧酸的乙烯酯和丙烯酯,其中烃基可为直链或支链的。其中,优选乙烯酯。在具有支链烃基的羧酸中,优选其中支链位于羧基的α位的那些,α碳原子更优选为叔碳,这表示该羧酸为所谓的新羧酸。然而,羧酸的烃基优选为直链。
合适的羧酸烯基酯的实例为乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、2-乙基己酸乙烯酯、新戊酸乙烯酯、己酸乙烯酯、新壬酸乙烯酯、新癸酸乙烯酯和相应的丙烯酯,优选乙烯酯。特别优选的羧酸烯基酯为乙酸乙烯酯;由此得到的典型共聚物是大规模使用和用于柴油的乙烯-乙酸乙烯酯共聚物(“EVA”)。
更优选地,烯键式不饱和单体选自羧酸烯基酯。
马来酸二烷基酯和富马酸二烷基酯的实例为马来酸或富马酸的甲酯、乙酯、正丙酯、异丙酯、正丁酯、仲丁酯、异丁酯、正戊酯、正己酯、2-乙基己酯和2-丙基庚基酯,它们是混合的或优选相同(即在烷基相同的情况下)的酯。
还合适的为包含共聚形式的两个或多个不同的羧酸烯基酯的共聚物,它们的烯基官能团和/或羧酸基团是不同的。与羧酸烯基酯的共聚物一样,同样合适的为包含共聚形式的至少一种烯烃和/或至少一种(甲基)丙烯酸酯的共聚物。
在共聚物中,共聚的烯键式不饱和单体的量优选为1至50摩尔%,特别为10至50摩尔%且尤其为5至20摩尔%,基于全部共聚物计。
共聚物的数均分子量Mn优选为1000至20 000,更优选1000至10 000且特别为1000至6000。
通过使用本发明的共聚物还可以改善许多其他燃料特性。在此仅作为示例性提及的是作为浊点抑制剂(CPD)或作为增效剂与流动改进剂一起用于进一步改善CFPP的其他效果。
本发明的共聚物可加入至全部为化石来源的中间馏分燃料(即,由矿物油获得那些),或者与包含基于矿物油的部分一样加入至包含部分生物柴油的燃料,以改善其特性。在两种情况下,无论燃料的来源或组成如何,在中间馏分燃料中都观察到了冷流特性显著的改善,即,CP值和/或CFPP值降低。沉淀出的链烷烃晶体有效地保持悬浮状态,因此不会存在过滤器和管线被沉淀的链烷烃堵塞。本发明的共聚物具有良好的活性谱,因此实现了沉淀的链烷烃晶体在各种不同的中间馏分燃料中的非常好的分散。
本发明还提供包含本发明的共聚物的燃料,特别是具有生物柴油成分的那些。
通常,燃料或燃料添加剂浓缩物还包含以其通常用量的其他添加剂:流动改进剂(如上所述)、其他链烷烃分散剂、导电性改进剂、防腐添加剂、润滑添加剂、抗氧化剂、金属钝化剂、消泡剂、破乳剂、清洁剂、十六烷值改进剂、溶剂或稀释剂、染料或香料或其混合物。上述其他添加剂是本领域技术人员所熟悉的,因此在此不再赘述。
在本发明的上下文中,燃料油应理解为表示化石、植物或动物来源的中间馏分燃料,生物燃料油(“生物柴油”)以及这种中间馏分燃料和生物燃料油的混合物。
中间馏分燃料(下文还简称为“中间馏分”)特别应理解为表示通过在第一工艺步骤下蒸馏原油并在120至450℃的范围内沸腾得到的燃料。这种中间馏分燃料特别用作柴油燃料、加热用燃料油或煤油,特别优选柴油燃料和加热用燃料油。优选使用低硫的中间馏分,即,包含小于350ppm的硫,特别小于200ppm的硫,尤其小于50ppm的硫的那些。在特殊情况下,它们包含小于10ppm的硫;这些中间馏分也被称作“无硫的”。它们通常为已在氢化条件下精炼并因此仅包含少量的多芳族和极性化合物的原油馏分。它们优选为90%的蒸馏点低于370℃,特别低于360℃且在特殊情况下低于330℃的那些中间馏分。
低硫和无硫中间馏分也可由在大气压力下无法蒸馏的相对重质的矿物油馏分获得。由重质原油馏分制备中间馏分的常规转化方法包括:加氢裂化、热裂解、催化裂化、焦化处理和/或减粘裂化。根据所述方法,这些中间馏分以低硫或无硫的形式获得,或将其在氢化条件下进行精炼。
所述中间馏分优选具有低于28重量%,特别低于20重量%的芳族化合物含量。正链烷烃的含量为5重量%至50重量%,优选10至35重量%。
在本发明的上下文中,中间馏分燃料在这里还应理解为表示可由化石源(例如矿物油或天然气)间接获得的那些燃料,或者由生物质通过气化并随后氢化制备的那些燃料。由化石源间接获得的中间馏分燃料的典型实例为通过Fischer-Tropsch合成获得的GTL(“天然气合成油(gas-to-liquid)”)柴油燃料。中间馏分由生物质例如通过BTL(“生物质制油(biomass-to-liquid)”)方法制备,并且其可单独用作燃料或与其他中间馏分以混合物的形式用作燃料。所述中间馏分也包括能够通过脂肪和脂肪油的氢化获得的烃。它们主要包括正链烷烃。
加热用燃料油和柴油燃料的质量例如,在DIN 51603和EN 590(还参见Ullmann’sEncyclopedia of Industrial Chemistry,第五版,卷A12,第617页及之后)中更详细地阐述。
除了其在上述化石、植物或动物来源的中间馏分燃料(其主要为烃混合物)中使用以外,本发明的共聚物还可在生物燃料油和上述中间馏分与生物燃料油的混合物中使用,以改善冷流特性。这类混合物市售可得且通常包含少量的生物燃料油,其含量通常为1重量%至30重量%,特别是3重量%至10重量%,基于化石、植物或动物来源的中间馏分和生物燃料油的总量计。
生物燃料油通常基于脂肪酸酯,优选主要基于衍生自植物油和/或动物油和/或脂肪的脂肪酸的烷基酯。烷基酯优选理解为表示低级烷基酯,特别是C1-至C4-烷基酯,其可通过将植物油和/或动物油和/或脂肪中存在的甘油酯(特别是甘油三酯)借助于低级醇(例如乙醇或尤其是甲醇)进行酯交换而获得(“FAME”)。基于植物油和/或动物油或脂肪并被用作生物燃料油或其组分的常见低级烷基酯为例如HVO(氢化植物油)、葵花油甲酯、棕榈油甲酯(“PME”)、大豆油甲酯(“SME”)和特别是菜籽油甲酯(“RME”)。
本发明的共聚物使燃料,特别是包含生物燃料油的燃料中的链烷烃晶体的结晶减少。
另外,上述提及的其他添加剂是本领域技术人员所熟知的,因此在此不再赘述。
下述实施例旨在阐明本发明而不限制本发明。
实施例
制备实施例1至16:
步骤1:
首先,将表A所述量的150和烯烃装入2升的试验搅拌器系统中。将初始进料充入N2并加热至150℃。在达到温度的同时,通过可加热的进料器在3小时内将表A中所述量的在80℃下呈熔融形式的马来酸酐(MA)连续加入到反应混合物中。
平行地,将表A中所述量的叔丁基过氧化物作为引发剂在3小时内计量加入反应中,将表A中所述量的合适的丙烯酸酯在分开的进料中也在3小时内加入反应中。在马来酸酐和引发剂的进料结束后,在150℃下再搅拌反应混合物1小时。
步骤2:
将表A中所述量的胺1加入步骤1的反应混合物中。将混合物在160℃下搅拌4小时。随后,再一次性加入表A中全部所述量的胺2并将混合物再搅拌15分钟。随后,将反应物冷却并终止。如果需要,随后将共聚物用150稀释至50%的含量。
所得共聚物的重均分子量(Mw)和多分散性(PD)通过GPC测定并记录在表B中。
用途实施例
在用途实施例中,使用表C中记录的来源和指标细节的柴油燃料(DF)。
作为链烷烃分散剂的功效(WASA)
在以下实施例中(表1至4),在常规流动改进剂(MDFI)的存在下,研究了上述制备的共聚物作为链烷烃分散剂(WASA)的功效。
测定含添加剂的燃料样品根据ISO 3015的浊点(CP)和根据EN 116的CFPP。然后,为测定ΔCP,将在500mL玻璃杯中含添加剂的燃料样品在冷浴中冷却至-16℃并在该温度下储存16小时。对于各样品,根据ISO3015,再次测定在-16℃下分离的20体积%的基础相的CP。对于各自的燃料样品,20体积%的基础相的CP与原CP的偏差(ΔCP)越小,则链烷烃的分散性越好。
ΔCP越小且CFPP越低,则柴油燃料的冷流特性越好。
本发明的共聚物改善了ΔCP或CFPP或这两个参数的冷流特性。
用于短暂沉降(brief sediment)试验的方法类似于Aral Method QSAA FKL 027,其中具有以下改变:
柴油燃料1-4:冷却至-16℃并在该温度下保持16小时。
WASA制剂包含36重量%的特定共聚物。
使用的MDFI是市售的流动改进制制剂:
MDFI 1为乙烯/乙酸乙烯酯共聚物、乙烯/乙酸乙烯酯/丙烯酸丙基庚基酯三元共聚物和聚丙烯酸酯在溶剂油中的混合物
MDFI 2为在溶剂油中的乙烯/乙酸乙烯酯共聚物
MDFI 3为在溶剂油中的乙烯/乙酸乙烯酯/丙烯酸丙基庚基酯三元共聚物
MDFI 4为在溶剂油中的乙烯/乙酸乙烯酯/丙烯酸乙基己基酯三元共聚物
作为浊点抑制剂的功效(CPD)
在表5中,在各种柴油燃料中测定来自实施例1的本发明共聚物作为浊点抑制剂(CPD)的功效。
与不含添加剂的燃料相比,CP降低得越多,则作为浊点抑制剂的功效越好。
本发明的共聚物显著降低CP。
CPD制剂包含36重量%的来自实施例1的于溶剂油中的共聚物。
作为CFPP改进剂(增效剂)的功效
在表6中,在常规MDFI的存在下,测定来自实施例1的本发明的共聚物作为共添加剂(增效剂)用于进一步改善CFPP的功效。
通过本发明的共聚物,使用较低的总剂量可实现目标CFPP,或使用相同的总剂量实现降低的CFPP。
共添加剂包含36重量%的于溶剂油中的共聚物1。
Claims (11)
1.一种共聚物,其可通过将以下单体共聚并随后与至少一种二烷基胺(E)反应而获得:
(A)至少一种不饱和二羧酸或其衍生物,
(B)至少一种具有至少6至最高达且包括20个碳原子的α-烯烃,
(C)至少一种丙烯酸或甲基丙烯酸的C3-至C20-烷基酯或这种烷基酯的混合物,和
(D)任选地一种或多种除单体(A)、(B)和(C)以外的其他可共聚单体,
其中所述至少一种二烷基胺(E)中的两个烷基基团独立地为具有至少17至最高达30个碳原子的烷基基团,共聚形式的单体的摩尔结合比(A):(B):(C):(D)为1:0.5至2.0:0.5至2.0:0至0.1,基于共聚物中二羧酸(A)的引入单元计的二烷基胺(E)的摩尔比为至少1.2:1且最高达2.0:1。
2.根据权利要求1所述的共聚物,其中单体(A)选自马来酸、富马酸、2-甲基马来酸、2,3-二甲基马来酸、2-甲基富马酸、2,3-二甲基富马酸、亚甲基丙二酸和四氢邻苯二甲酸及其衍生物。
3.根据权利要求1或2所述的共聚物,其中单体(B)选自1-己烯、1-庚烯、1-辛烯、1-壬烯、1-癸烯、1-十一碳烯、1-十二碳烯、1-十三碳烯、1-十四碳烯、1-十五碳烯、1-十六碳烯、1-十七碳烯、1-十八碳烯、1-十九碳烯和1-二十碳烯。
4.根据权利要求1或2所述的共聚物,其中单体(C)选自丙烯酸和甲基丙烯酸与以下醇的酯:正丙醇、异丙醇、正丁醇、仲丁醇、异丁醇、叔丁醇、正戊醇、叔戊醇、正己醇、正庚醇、正辛醇、2-乙基己醇、正壬醇、异壬醇、正癸醇、2-丙基庚醇、正十一烷醇、异十一烷醇、正十二烷醇、正十三烷醇、异十三烷醇、3,3,5,5,7-五甲基辛醇、正十四烷醇、正十五烷醇、正十六烷醇、正十七烷醇、异十七烷醇、3,3,5,5,7,7,9-七甲基癸醇、正十八烷醇和正二十烷醇。
5.根据权利要求1或2所述的共聚物,其中任选地单体(D)选自脂环族的(甲基)丙烯酸酯(D1)、聚亚烷基二醇单烷基醚的(甲基)丙烯酸酯(D2)、链烷酸乙烯酯(D3)、烯丙基化合物(D4)、乙烯基醚(D5)、N-乙烯基内酰胺(D6)、N-乙烯基咪唑(D7)、烯键式不饱和芳族化合物(D8)、二氧化硫(D9)和烯键式不饱和腈(D10)。
6.根据权利要求1或2所述的共聚物,其中二烷基胺(E)为二-正十八烷基胺、二-正十九烷基胺和二-正二十烷基胺。
7.根据权利要求1或2所述的共聚物,其重均分子量Mw为2000至20000,通过凝胶渗透色谱测定。
8.一种制备前述权利要求中任一项所述的共聚物的方法,其在连续或间歇操作的装置中,在50至250℃的聚合温度下通过溶剂聚合、乳液聚合、沉淀聚合或本体聚合随后与至少一种二烷基胺(E)反应而进行,其中所述至少一种二烷基胺(E)中的两个烷基基团独立地为具有至少17至最高达30个碳原子的烷基基团。
9.根据权利要求1至7中任一项所述的共聚物用于降低燃料中链烷烃晶体结晶的用途。
10.根据权利要求1至7中任一项所述的共聚物用于改善燃料油的冷流特性和用于改善包含冷流改进添加剂的燃料油的可滤性的用途。
11.燃料油,其包含10至5000重量ppm的至少一种根据权利要求1至7中任一项所述的共聚物和另外任选的选自以下的其他添加剂:冷流改进剂、链烷烃分散剂、导电性改进剂、防腐添加剂、润滑添加剂、抗氧化剂、金属钝化剂、消泡剂、破乳剂、清洁剂、十六烷值改进剂、溶剂或稀释剂、染料或香料。
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EP0606055A2 (de) * | 1993-01-06 | 1994-07-13 | Hoechst Aktiengesellschaft | Terpolymere auf Basis von alpha,beta-ungesättigten Dicarbonsäureanhydriden, alpha,beta-ungesättigten Verbindungen und Polyoxyalkylenethern von niederen, ungesättigten Alkoholen |
DE60016804T2 (de) * | 1999-12-28 | 2005-12-15 | Total France | Zusammensetzung von mehrzweckzusätzen zur kälteverwendbarkeit der mitteldestillate |
EP2535396A1 (en) * | 2010-02-10 | 2012-12-19 | NOF Corporation | Fluidity improver for fats and oils |
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DE4330971A1 (de) | 1993-09-13 | 1995-03-16 | Basf Ag | Copolymerisate sowie deren Reaktionsprodukte mit Aminen als Kraftstoff- und Schmierstoffadditiv |
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DE19754039A1 (de) | 1997-12-05 | 1999-06-24 | Basf Ag | Verfahren zur Herstellung von Ethylencopolymeren in segmentierten Rohrreaktoren und Verwendung der Copolymere als Fließverbesserer |
EP1203054B1 (en) * | 1999-08-12 | 2004-11-03 | Ciba SC Holding AG | Polymer blends with improved impact resistance |
DE10247795A1 (de) | 2002-10-14 | 2004-04-22 | Basf Ag | Verwendung von Hydrocarbylvinyletherhomopolymeren zur Verbesserung der Wirkung von Kaltfliessverbesserern |
DE10349851B4 (de) | 2003-10-25 | 2008-06-19 | Clariant Produkte (Deutschland) Gmbh | Kaltfließverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs |
DE102006022719B4 (de) | 2006-05-16 | 2008-10-02 | Clariant International Limited | Kaltfließverbesserer für pflanzliche oder tierische Brennstofföle |
DE502007002278D1 (de) | 2006-06-22 | 2010-01-21 | Basf Se | Mischung aus polaren öllöslichen stickstoffverbindkraftstoffe |
WO2009124979A1 (de) | 2008-04-10 | 2009-10-15 | Basf Se | C17-alkoholgemisch |
US20130133243A1 (en) * | 2011-06-28 | 2013-05-30 | Basf Se | Quaternized nitrogen compounds and use thereof as additives in fuels and lubricants |
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- 2015-11-11 US US15/531,303 patent/US10557096B2/en active Active
- 2015-11-11 CN CN201580064323.XA patent/CN107001535B/zh active Active
- 2015-11-11 RU RU2017122383A patent/RU2690940C2/ru active
- 2015-11-11 WO PCT/EP2015/076317 patent/WO2016083130A1/de active Application Filing
- 2015-11-11 KR KR1020177017617A patent/KR102460031B1/ko active IP Right Grant
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US4526950A (en) * | 1982-04-20 | 1985-07-02 | The Lubrizol Corporation | Method for preparing interpolymers |
US4731095A (en) * | 1982-06-04 | 1988-03-15 | Institut Francais Du Petrole | Nitrogen containing copolymers useful as additives for lowering the cloud point of hydrocarbon middle distillates and compositions containing them |
US4511369A (en) * | 1982-11-09 | 1985-04-16 | Institut Francais Du Petrole | Copolymers with nitrogen groups, useful as additives for decreasing the cloud point of hydrocarbon middle distillates and compositions containing them |
FR2592888A1 (fr) * | 1986-01-10 | 1987-07-17 | Inst Francais Du Petrole | Compositions d'additifs destinees notamment a ameliorer les proprietes de filtrabilite a froid des distillats moyens de petrole |
EP0606055A2 (de) * | 1993-01-06 | 1994-07-13 | Hoechst Aktiengesellschaft | Terpolymere auf Basis von alpha,beta-ungesättigten Dicarbonsäureanhydriden, alpha,beta-ungesättigten Verbindungen und Polyoxyalkylenethern von niederen, ungesättigten Alkoholen |
DE60016804T2 (de) * | 1999-12-28 | 2005-12-15 | Total France | Zusammensetzung von mehrzweckzusätzen zur kälteverwendbarkeit der mitteldestillate |
EP2535396A1 (en) * | 2010-02-10 | 2012-12-19 | NOF Corporation | Fluidity improver for fats and oils |
Also Published As
Publication number | Publication date |
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CA2969027C (en) | 2023-02-28 |
WO2016083130A1 (de) | 2016-06-02 |
RU2017122383A3 (zh) | 2018-12-28 |
EP3224285B1 (de) | 2020-07-08 |
US20170355916A1 (en) | 2017-12-14 |
RU2690940C2 (ru) | 2019-06-07 |
CN107001535A (zh) | 2017-08-01 |
RU2017122383A (ru) | 2018-12-28 |
US10557096B2 (en) | 2020-02-11 |
KR20170091123A (ko) | 2017-08-08 |
CA2969027A1 (en) | 2016-06-02 |
KR102460031B1 (ko) | 2022-10-27 |
EP3224285A1 (de) | 2017-10-04 |
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