CN101171210B - 烃的合成 - Google Patents

烃的合成 Download PDF

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CN101171210B
CN101171210B CN2006800150695A CN200680015069A CN101171210B CN 101171210 B CN101171210 B CN 101171210B CN 2006800150695 A CN2006800150695 A CN 2006800150695A CN 200680015069 A CN200680015069 A CN 200680015069A CN 101171210 B CN101171210 B CN 101171210B
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I·M·洛科维克
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Abstract

从较小的烃合成烃的方法，包括烃卤化、同时低聚和卤化氢中和以及产品回收的步骤，用金属-氧催化反应物来促进碳-碳偶联。用空气或氧处理以释放卤素并再生该催化反应物。

Description

烃的合成
发明领域
本发明通常涉及烃的低聚，且更具体地涉及使用催化反应物(cataloreactants)制造烃的方法。 
发明背景 
科学家们已经长期探寻将甲烷和其它烷烃转化为更高级的烃(包括轻质烯烃和汽油范围内的物质)的方法。有效的方法能够以多种方式创造价值，包括：促进将位置遥远的海滨天然气转化为更易运输的液体燃料和原料，和允许为了终端产品而使用廉价的原料(甲烷和其它低级烷烃)，该终端产品通常由高级烷烃包括乙烯和丙烯制造。 
美国专利No.6,486,368、6,472,572、6,465,699、6,465,696和6,462,243公开了将烷烃转化为烯烃、醚和醇的方法。许多公开的方法包括：烷烃的卤化，使该卤化的产物通过金属氧化物以生成产品和金属卤化物，回收该产品，并用氧或空气再生该金属卤化物以得到用于再循环到该过程中的金属氧化物和卤素。没有描述的是烷烃的低聚：起始烃的大量偶联以得到更高碳数的产物。 
一些研究者已经研究了使用卤化来从甲烷生产高级烃。代表性的专利包括4,513,092(Chu)、4,769,504(Noceti和Taylor)、5,087,786(Nubel)、和6,452,058(Schweitzer)。如Taylor的专利所述：“由低级烷烃特别是由甲烷制造富含芳烃的汽油沸程的烃。该方法在两个阶段进行。在第一阶段，烷烃与氧和氯化氢在氧氢氯化催化剂(例如具有小比例的氯化钾和稀土氯化物的氯化铜)上反应。这产生含有水和氯化烷烃的中间气体混合物。该氯化烷烃与氢型或金属促进型的晶态硅酸铝催化剂接触以产生具有高比例的芳烃和小百分比的轻质烃(C2-C4)的汽油范围的烃，并再次生成HCl。该轻质烃可再循环以进一步在该氧氢氯化催化剂上处理。”所有这些从C1原料制造更高级烷 烃的技术都受困于以下缺点：烃流必须与含水的氢卤酸流分开，且该氢卤酸流必须被再循环。 
美国专利4,795,843(Tomotsu等人)公开了使用多晶型二氧化硅或硅沸石催化剂将卤甲烷低聚成产品的方法，该产品包括乙苯、甲苯和二甲苯。该方法不包括卤化氢的反应性中和，但显示出受困于缓慢的动力学。 
在用于卤化烃的方法中，Chang和Perkins注意到在美国专利4,654,449中在沸石存在下痕量的低聚产物。该低聚产物的含量低，且通常是卤化的。 
美国专利4,373,109(Olah)公开了转化混杂取代的甲烷包括卤甲烷的方法，该方法通过使这些甲烷与双功能的酸基催化剂在升高的温度(200-450℃，优选250-375℃)下接触以主要产生低级烯烃，优选乙烯和丙烯。该优选的催化剂衍生自周期表第IV、V、VI、VIII族过渡金属(例如钽、铌、锆、钨、钛和铬)的卤化物、氧卤化物、氧化物、硫化物或氧硫化物，它们沉积在酸性氧化物或硫化物(例如氧化铝、二氧化硅、二氧化锆或二氧化硅-氧化铝)上。既没有公开基于固体氧化物的卤素回收也没有公开醇或醚的生成。相关的参考文献是“Ylide chemistry.1.Bifunctional acid-base-catalyzedconversion of heterosubstituted methanes into ethylene andderived hydrocarbons. The onium-ylide mechanism of the C1→C2conversion”，George A.Olah等人，(J.Am.Chem.Soc.106，2143(1984))。 
美国专利3,894,107(Butter等人)公开了使用沸石催化剂缩合卤化烃方法的改进。显然没有对于任何基于固体氧化物的卤化氢中和的讨论。 
Kochi已经观察到当过渡金属溴化物与低分子量的格氏试剂在THP或二乙醚中反应时的烷基卤化物的还原偶联(Bulletin of theChemical Society of Japan v.44 1971页3063-73)。然而，液相化学通常受困于这些缺点：需要溶剂、存在腐蚀且比气相化学反应速 率低。此外，这个方法需要消耗能量以生产充满活性的和还原性的格氏试剂所需的金属镁。这与我们这里所描述的脱氢卤化偶联和卤化氢中和不是相同类型的方法。 
发明概述 
本发明针对将甲烷和其它烃转化为较高级烃的有效方法的需要。在一个实施方案中，碳数为Cn(其中n≥2)的烃是这样制备的：使碳数为Cm(其中m＜n)的烃与卤化试剂反应，由此生成卤化烃；使该卤化烃与金属-氧催化反应物接触，由此生成碳数为Cn(其中n≥2)的产物烃；回收该产物烃；并再生该催化反应物。通常，得到烃的混合物，但小心地选择反应物烃、卤化试剂、金属-氧催化反应物和反应条件允许生成烃产物的定制的方法。甲烷(即，天然气)以及其它轻质烃例如C2-C6烃被设想为优选的原料。更通常地，本发明预期使用碳数高达C10的原料。实验室观察迄今集中于甲烷低聚和甲基溴偶联，和C2-C10物种(包括烷烃、烯烃、支化的烃和芳族化合物)的检测。 
发明详述 
本发明开发了金属-氧化合物促进烃低聚的发明，该金属-氧化合物例如：混合的金属氧化物、掺杂的沸石(即，碱土金属掺杂的沸石)、金属氧化物浸渍的沸石等。根据本发明的一个方面，碳数为Cn (其中n≥2)的烃由下面步骤生成：(i)使碳数为Cm(其中m＜n)的反应物烃与卤化试剂反应生成卤化烃；(ii)使该卤化烃与金属-氧催化反应物接触，生成碳数为Cn(其中n≥2)的产物烃；(iii)回收该产物烃；和(iv)再生该催化反应物。 
更通常地，该方法需要卤化、低聚、产物回收和催化反应物再生的步骤。可在卤化的产物与金属-氧催化反应物反应之前或之后将其与未反应的(未卤化的)烃分开。中和在该合成过程中所生成的任何氢卤酸伴随着有利地实现碳-碳偶联和/或催化反应物再生。优选地，该方法是集成为一体的并发生在例如美国专利6,525,230(Grosso)所述的区域反应器(zone reactor)中，将该专利的全文引入本文供 参考。因此，甲烷或其它烃的卤化发生在该反应器的一个区域内，然后是缩合步骤，该步骤中释放的氢卤酸被催化该卤化烃缩合的同一双功能材料吸收。烃的低聚(定义为碳-碳偶联)发生在该反应器的这个区域内，并生成碳数通常为C2-C20的产物烃，该产物烃可包括烷烃、烯烃、炔烃和/或芳烃。用空气或氧处理释放卤素，用于后续的卤化步骤，且再生所述的催化反应物物质用于后续的缩合或置换。有利地，因为再生和回收原位发生，避免了再循环/回收腐蚀性的含水氢卤酸的需要。 
高级烃的合成从烃原料开始：一种或多种反应物烃，每种独立地具有碳数Cm(其中m＜n，Cn是目标烃的碳数)。反应物烃的非限制性实例包括甲烷、乙烷、丙烷等，优选天然气(主要是甲烷，但通常包括少量的C2和更高级的物种)。通常，起始烃的碳数为1-10。也可使用烃的混合物。 
使所述的反应物烃与卤化试剂反应。非限制性的实例包括卤素分子(例如溴、氯等)、烷基卤化物(例如，二甲基溴、溴仿、四溴化碳)和缩合的卤化物，例如金属溴化物，它可以固体、液体、负载的或非负载的物质存在。 
优选卤素分子，最优选溴(Br2)。溴在室温下是液态，比氯和氟的反应性低，并易于操作。溴也有良好的活性。 
溴至溴化物的还原电势为1.07V对NHE，而氧至水为1.23V。宽范围的金属溴化物经过用氧处理可释放溴。同时，烷的溴化和后续的烷基溴化物的偶联和HBr的中和仅轻微放热，但自发地足以直至完成。仅水和偶联的烃是液态产物。以氯为介质时却并非如此，因为HCl是产物流的主要组分。产生的氯化氢需要分离、干燥和再循环，这是昂贵的。简言之，以金属溴化物为媒介的烷烃部分氧化的热化学非常适于有效的和廉价的工厂操作。 
反应物烃的卤化可以多种方式进行，部分取决于所希望的产物，部分取决于原料。在一个实施方案中，以卤素分子来烷基卤烃，该反应使用热、光、或其它电磁辐射来驱动，优选用热。使所有的步骤- 卤化、低聚和再生(下述)-发生在大概相同的温度下是有一些益处的。对于甲醇到烯烃(MTO)和甲醇到汽油(MTG)过程，使用375-450℃的温度，该范围是重要的，即使不是关键的。对于本文所述的碳-碳偶联过程，理想的温度范围是450-550℃，所有的步骤发生在大概同一温度下。 
然而，个别反应步骤可在高于或低于该范围的温度下进行。事实上，在较低的反应温度下汽油收率更佳，和在下面的某些实施例中，甲基溴与碱土金属掺杂的沸石的反应在225-350℃和1-5巴(14.5-72.5psi)下进行。然而，对于整个集成过程，工程上赞成三个反应在相似的温度下进行。 
对于后续的碳-碳步骤，卤化优选发生在0.1-200大气压下。低压有利于较小的碳-碳偶联(即，平均分子量较小的产物)，而高压有利于较高的偶联。尽管可以可选地使用更高的压力，用于轻质烯烃的过程很可能在60-200psia下进行，其与甲醇到烯烃(MTO)过程运行在相同的压力下。对于汽油范围内的分子的生产来说，预期使用如在甲醇到汽油(MTG)过程中所用的约350psia的压力。特别的是，不可能在低于大气压下(更保守地说，低2psia)或高于100个大气压下运行。 
当卤素分子用作卤化剂时，在基于体积/体积，烷烃∶卤素的比例为1∶10-约100∶1下烷烃被理想地卤化。烷烃∶卤素的比例小于1∶10(即更多的卤素)时，会生成多卤化烃，通常导致经后续与金属-氧催化反应物接触发生完全氧化(即，CO2)。当烷烃∶卤素的比例高于100∶1时，卤化烃的转化率会太低，大约1％或更低，和在这样的转化率水平上，难以想象会有经济的过程。(30-60％的转化率是更可能的下限)。 
改变卤素与烷烃或其它烃原料的比例会对产物分布有显著影响。例如，人们可以选择控制卤化程度以在低级烯烃或燃料的生产中减少芳烃的生成。第二个实例是使高度卤化的甲烷最小化以减少炔的生成。 
本发明的关键特征是使用金属-氧催化反应物，它促进碳-碳偶联，即烃的低聚。这里使用的术语“金属-氧催化反应物”是指催化反应物物质既含有金属又含有氧。然而，不拘泥于理论，据信该物质经由卤化氢(例如，HBr)消去和将亚烷基插入到阳离子活化的C-H和也许是C-C键中来催化碳-碳偶联。该催化反应物也充作卤素释放和隐蔽剂，并提供得到可调的偶联产物分布的可能性，包括如果希望的话产生含氧化合物的能力，而同时捕集和回收卤素，仅排出水作为副产物。用空气和氧处理再生该催化反应物。
金属-氧催化反应物的非限制性实例包括沸石、掺杂的沸石、金属氧化物、混合的金属氧化物、金属氧化物浸渍的沸石和类似的材料，以及这些材料的混合物。掺杂剂的非限制性实例包括碱土金属例如钙和镁，和它们的氧化物和/或氢氧化物。 
可从各种来源得到沸石，包括Zeolyst International(Valley Forge，PA)。具体的实例包括掺杂的ZSM-5和掺杂的丝光沸石(其中，例如，钙和/或镁为掺杂剂)。 
在一优选的实施方案中，沸石的Si∶Al的比例为约80∶1至280∶1。 
改变沸石的性质或沸石/金属氧化物复合物的沸石的组分也预期改变产物分布。特别认为孔尺寸和酸度是重要的。酸度可用于控制链长度和官能度，和孔尺寸可控制链长度和官能度。特定孔尺寸的沸石可选择性地生产苯、甲苯、对二甲苯、邻二甲苯、间二甲苯、混合的二甲苯、乙苯、苯乙烯、直链烷基苯或其它芳族产物。孔尺寸的用途不限于芳族产物。 
在本发明的一个实施方案中，金属氧化物/沸石复合物的制备如下：混合沸石和金属硝酸盐(例如，碱土金属氧化物，例如硝酸钙)或它们的水合物种，然后煅烧该混合物以释放氮氧化物并保留该金属氧化物浸渍的沸石。 
低聚后，通常在200-900℃下用空气或氧处理来再生该金属-氧催化反应物。这将金属卤化物物种转化为金属-氧物种。 
许多变量，包括原料组成、反应器的进料位置、温度、压力、金属氧化物组成和反应器停留时间都可改变产物分布。由甲烷生产烷烃、烯烃和芳烃已经被检测和证实。也期望能生产特殊支化的烷烃和烯烃(包括单甲基支化的醇)、醇、二醇、醚、卤化烃、芳烃(包括苯、苯乙烯、乙苯、甲苯、二甲苯和直链烷基苯)和适于作为燃料(例如汽油、柴油和喷气燃料)的烃。 
控制原料组成能控制产物分布。首先，在卤化中产生的卤化氢可用产生烃产物的同一金属-氧化合物中和/或在另一反应器中用单独的金属-氧化合物中和(以生成水或醇)。改变卤化氢的中和位置可改变产物分布，包括官能度、链长度和支化度。例如，中和和产物生成同时发生可预期促进醇的生成，该醇可以或可以不经历进一步反应例如偶联或脱水。其次，向原料中加入水会改变产物分布。特别地，加入水可有利于醇产物。加入水也可控制支化的程度和类型和链长度。第三，加入氢可改变产物分布。氢可以以其它官能度为代价增加特别用于生产燃料的烷烃。氢也可以减少结焦并有助于控制链长度和支化度。 
还必须清楚的是，碳-碳低聚也可通过多种途径进行。甚至单独的烃原料可产生多于一种的产物。另一方面，在本发明的一个实施方案中，使用受控制的卤化以主要生产优于其它异构体的一种异构体(例如，选择性地生成1-丁烯或2-丁烯)。混合的原料，例如未处理的天然气，可增加多卤化烃(例如，乙基卤、二卤乙烷、甲基卤、二卤甲烷、丙基卤、二卤丙烷，等)的低聚。事实上，在本发明的一个实施方案中，有目的地导入烷基卤以产生所希望的支化产物。一个实例将是甲基卤(来自甲烷)与乙基卤或更高级的烷基卤的低聚以选择性地生成甲基、乙基、丙基、异丙基、或叔丁基(或其它)分支。另一个实例可以是由乙基卤、甲基卤和二卤甲烷合成苯乙烯。 
在本发明的一个实施方案中，卤化烃与金属-氧催化反应物的反应发生在流化床中。也可选择使用固定床地。不同的烷基卤可在不同的位置导入反应器。一个实例是在一个位置将甲基卤化物导入反应器中以产生苯，向该位置加入乙基卤则产生苯乙烯或乙苯。另一个实例是在一个位置将甲基卤化物导入反应器中以产生苯，向该位置加入烷基卤则产生直链烷基苯。 
通过任何适宜的方法完成产物分离。非限制性的实例包括蒸馏、 吸附和萃取。用蒸汽、二氧化碳或其它手段汽提可从固体中回收产物。 
下面是本发明的非限制性实施例： 
实施例1 
金属氧化物/沸石复合物MZl的制备如下：制备ZSM-5型沸石(Zeolyst CBV 8014，Si/Al比＝80∶1，10g，170mmoles SiO2)和无水CaNO3(9g，＝34mmoles Ca)的固体混合物，并加入水来初始润湿。在CaNO3溶解并搅拌后，干燥该淤浆并随后在空气中分别在115℃下煅烧(过夜)和500℃下煅烧(过夜)。 
实施例2 
以5毫升/分钟的速率将15psia下的甲烷鼓泡通过1℃下的溴。得到的溴和甲烷流(1∶10摩尔比)通过450℃下的小直径的溴化反应器(1000h-1)并将CH4-xBrx(x＝0，1，2，3)的混合物通入含有5g金属氧化物/沸石复合物MZl(400℃)的反应器中。第二个反应器的出口料流不含溴化产物。基于在溴化反应器中消耗的甲烷，检测到10％的乙烯、31％的丙烯、3％的丙烷和21％的丁烷/丁烯，总共65％。也检测到痕量的C6物种。反应5小时后，在该过程中出口料流没有改变上述的分布，停止甲烷流并用5毫升/分钟的氦冲洗反应器10分钟。He冲洗后，O2流(2毫升/分钟)开始在525℃下进入第二个反应器以将部分用过的复合物中的金属溴化物再生为金属氧化物。开始仅观察到水和CO2为产物，但突然地，该流体的内容物改变为Br2和未反应的O2。1小时后，停止该O2冲洗，并再次用氦清洗该反应器。在再生过程中使用苛性碱阱来检测CO3 2-并发现了1.0mmol，代表了24％的转化的碳。发现其余的碳成为沸点更高的挥发性芳烃(大多数为甲苯、二甲苯和均三甲苯)。上述甲基溴的第二轮缩合在400℃下开始，并且发现产物分布与第一轮相同。三轮以上的缩合/中和/再生输出相同的高级烃。 
实施例3 
按照实施例1制备掺杂的丝光沸石(Zeolyst CBV 21A，同时掺有Ca和Mg)(5g)，并用作烃合成中的催化反应物，该烃合成与以上实 施例2中所述基本上相似。产物输出为30％乙烯、5％乙烷、10％丙烯、3％丙烷、5％丁烷/丁烯。多轮运转和催化反应物的再生确立了可再现性。 
实施例4-15 
按照实施例1中所述的程序用钙掺杂来自Zeolyst Corp.的ZSM-5型沸石(Zeolyst CBV 28014，Si∶Al比为280∶1)至Ca∶Si比为4∶1。将1.427g粗略磨碎的掺杂钙的沸石装入玻璃反应管(长6英寸，内径4毫米)，并使甲基溴料流(4.5mmol)流进该管。在甲基溴转化后，固体用O2(2标况毫升/分钟，1巴)在520℃下处理3小时来再生，并回收放出的Br2。每轮使用相同的固体和相同量的甲基溴在压力、温度和流量范围内实施该甲基溴偶联反应。产物和任何未反应的甲基溴离开该反应管的另一端并用一个或多个GC、GC/MS和NMR分析。由于明白无误的同位素比例和破裂模式，GC/MS特别用作对溴代烃含量(它一般为零)的诊断。 
表1概述了烃产物的分布(也称作“选择性”(sel)，以百分比表示)、CH3Br的转化百分比和反应参数T、P和τ(空时)，其中τ根据下面公式计算：τ＝反应器体积/引入的流量。芳族产物分布以下划线表示。 
表1实施例4-15：CH3Br在掺杂钙的ZSM-5上偶联：反应参数和产物 
Figure 000008
[0048] 由表1可见，掺杂碱土金属的沸石促进了溴化的烷烃(CH3Br)转化为多种不同的烃，包括直链和支化的烷烃、烯烃和芳族化合物。水也作为HBr中和的副产物而产生。产物的GC分析显示，甲基溴的转化率高(在低温下转化率较低，和高温下转化率较高)，且pH值测量显示，在反应中生成的HBr被完全中和。 
通常，对于给定的运转来说，产生的C5和更高级的烃的百分比超过70％，且产生的C6和更高级的烃的百分比超过50％。检测到的芳族化合物包括甲苯(C7)、二甲苯和乙苯(C8)、均三甲苯和甲乙苯(C9)和更高级的烃(例如，C10)。在某些运转中，检测到少量的苯。 
尽管不拘泥于理论，该碳-碳偶联看来以两个阶段进行，这类似于从甲醇偶联生成烃所观察到的。首先是快速阶段，看来生成烯烃、偶联，然后裂化。然后看来是较缓慢的第二阶段，在较长地暴露于催化剂和较高的温度下之后产生芳族产物和链烷烃。 
已经观察到，新鲜制备的固体催化反应物不给出“稳态的”产物分布，该“稳态的”产物分布在一轮(许多其它轮的重复之处)的偶联/溴捕捉、然后是固体再氧化和溴释放之后得到。即，首轮的产物分布不同于使用再循环的固体催化反应物的分布。 
实施例16-18 
为了示范较轻的烃能再循环到该偶联反应器中，首先以丙烯(4.5mmol)，然后以CH3Br和丙烯的混合物(3∶1 v/v或3.3mmol∶1.1mmol)用作玻璃反应管(其配置如实施例4-15所述)内的原料。其产物分布与单独使用CH3Br(4.5mmol)所得到的分布相比较。结果列于表2。芳族产物分布以下划线表示。 
表2实施例16-18：丙烯(实施例16)、3∶1的CH3Br∶丙烯(实施例17)和单独的CH3Br(实施例18)在掺杂钙的ZSM-5上的反应产物 
[0056] 表2显示，可将次希望的(从生产汽油的观点来说)轻质烯烃再循环到进料流中以结合成较重的产物。丙烯进料与MeBr和MeBr/丙烯1∶1(基于C∶C)进料的产物分布相似，该事实说明轻质烯烃再循环会改进汽油产品的总收率。 
已经参照不同的实施例和优选的实施方案描述了本发明，但并不限于它们。可不背离本发明的范围而做出其它的改动和替代。例如，本文所述的低聚方法也打算包括：使用卤化氢(例如，HBr)或卤素分子来卤化烯烃原料、使用卤化氢和卤素分子来卤化炔烃(炔类)、使用卤化氢和卤素分子来卤化醇或醚、和使用卤素分子和控制该卤化的催化剂来烷基卤烃。特别地，该催化剂可控制卤化程度(每分子的卤素数目)和卤化位置(例如，对长链烷烃来说，终端卤化还是中间卤化)之一或二者均可。也可做其它改动。本发明仅由所附的权利要求和它们的等价物所限定。 

Claims (19)

1.制造多种烃的方法，包括：
使甲基溴与掺杂碱土金属的沸石在足以产生多种烃的温度和压力下接触；和
使生成的至少一些C1-C3烃与掺杂碱金属的所述沸石接触以生成一种或多种C4或更高级的烃。
2.权利要求1的方法，其中所述的碱土金属选自钙、镁和它们的混合物。
3.权利要求1的方法，其中所述的沸石的Si∶Al的比例为80∶1至280∶1。
4.权利要求1的方法，其中所述的沸石的Si∶Al的比例为80∶1。
5.权利要求1的方法，其中所述的沸石的Si∶Al的比例为280∶1。
6.权利要求1的方法，其中所述的掺杂碱土金属的沸石的碱土金属∶硅的比例为4∶1。
7.权利要求1的方法，其中所述的多种烃包括至少一种芳烃。
8.权利要求7的方法，其中所述的至少一种芳烃包括至少一种选自苯、甲苯、二甲苯、乙苯、均三甲苯和甲乙苯的芳烃。
9.权利要求1的方法，其中所述的多种烃包括至少一种支化的烷烃。
10.权利要求1的方法，其中所述的多种烃包括至少一种烯烃。
11.权利要求1的方法，其中所述的多种烃包括至少一种烷烃、至少一种烯烃和至少一种芳烃。
12.权利要求1的方法，其中所述的多种烃包括汽油等级的烃混合物。
13.权利要求1的方法，其中所述的甲基溴由甲烷的溴化而生成。
14.权利要求13的方法，其中用Br2来溴化甲烷。
15.权利要求1的方法，其中所述多种烃包含至少50％的C6或更高级的烃。
16.权利要求1的方法，其中所述多种烃包含至少70％的C5或更高级的烃。
17.权利要求1的方法，其中所述多种烃包含至少50％C6或更高级的烃和至少70％的C5或更高级的烃。
18.权利要求17的方法，其中所述的温度为225-350℃，和所述的压力为1-5巴。
19.权利要求17的方法，其中所述掺杂的沸石是以4∶1的Ca∶Si的比例掺杂钙的ZSM-5型沸石。
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