CN1293647A - 二聚体的生产 - Google Patents

二聚体的生产 Download PDF

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CN1293647A
CN1293647A CN99804215A CN99804215A CN1293647A CN 1293647 A CN1293647 A CN 1293647A CN 99804215 A CN99804215 A CN 99804215A CN 99804215 A CN99804215 A CN 99804215A CN 1293647 A CN1293647 A CN 1293647A
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赫斯特·德威特
戴维·赫德里·摩根
阿尔塔·兰威尔
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Sasol Technology Pty Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/26—Catalytic processes with hydrides or organic compounds
    • C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
    • C07C2/34—Metal-hydrocarbon complexes
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    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
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    • B01J31/22—Organic complexes
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    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/46—Titanium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48—Zirconium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/49—Hafnium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes

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Abstract

本发明提供一种从含α－烯烃的烯烃原料生产二聚体的方法,该方法通过原料与金属茂/铝氧烷催化剂接触,通过金属茂催化的二聚反应选择性地使原料中的α－烯烃二聚。原料是费托反应衍生的烯烃原料,包括费托反应衍生的烃类混合物,其中含有至多90重%α－烯烃;至少5重%非α－烯烃的烯烃组分,选自直链内烯烃、支链内烯烃、环烯、二烯、三烯和它们的混合物;至少5重%非烯烃的组分,选自链烷烃、氧化的烃类、芳烃和它们的混合物。金属茂催化的二聚反应发生时,二聚的烯烃与原料形成混合物。

Description

二聚体的生产
本发明涉及一种从烯烃原料生产二聚体的方法。更详细地说，涉及一种适于从烯烃原料生产具有通式R’R”C=CH2产物的方法，其中R’与R”是烷基。
根据本发明，提供一种从含α-烯烃的烯烃原料生产二聚体的方法。该方法通过原料与金属茂／铝氧烷催化剂接触，通过金属茂催化的二聚反应选择性地使原料中的α-烯烃二聚。原料是费托反应衍生的烯烃原料，包括费托反应衍生的烃类混合物，其中含有至多90重％α-烯烃；至少5重％非α-烯烃的烯烃组分，选自直链内烯烃、支链内烯烃、环烯、二烯、三烯和它们的混合物；至少5重％非烯烃组分，选自链烷烃、氧化的烃类、芳烃和它们的混合物。金属茂催化的二聚反应发生时，二聚的烯烃与原料形成混合物。
费托反应衍生的烯烃原料是指一种烯烃原料，该原料通过在合适的费托反应催化剂存在下，将包含一氧化碳和氢气的合成气在合适的费托反应条件下反应生成的产物，其中催化剂可以是铁基、钴基或铁／钴基。尤为突出的是，从合成气的费托反应后，所得衍生的烯烃原料无需为了除去不需要的组分，如非α-烯烃组分，而进一步处理、纯化和加工，只要切取合适的费托反应的产物馏分用作原料。
所述原料可以包括50-90重％，例如60-80重％所说的α-烯烃；5-20重％，例如9-16重％所说非α-烯烃的烯烃组分；与5-30重％，例如13-22重％所说非烯烃组分。
实施例中，原料可以包括50重％α-烯烃，20重％非α-烯烃的烯烃组分，和30重％非烯烃组分。金属茂／铝氧烷催化剂可以包含甲基铝氧烷的铝氧烷组分；和具有(Cp)2MY2通式的化合物的金属茂组分，其中Cp代表环戊二烯基，M是选自锆、铪和钛的金属，Y是选自氢自由基、卤素自由基(优选氯自由基)、烷基(优选甲基)和它们的混合物。金属茂组分优选具有所说(Cp)2MY2通式的单个化合物，但也可以选用几个具有所说(Cp)2MY2通式化合物的一种混合物。
更为突出的是，原料中可以包含非α-烯烃的其它烯烃，包括直链内烯烃、支链内烯烃、环烯、二烯、三烯；和非烯烃组分，包括链烷烃、芳烃和少量氧化的烃类。在催化剂中，铝氧烷组分中的铝与金属茂中的金属的原子比Al∶M在1∶1至100∶1之间，优选40∶1至80∶1之间，例如60∶1至70∶1之间。当Al∶M原子比升高，反应的转化率与反应速率都得到提高，二聚反应的选择性却降低了；但是当Al∶M原子比下降，反应的转化率与反应速率都得到减小，二聚反应的选择性却提高了。考虑实用性与经济效益，采用常规实验手段选择最优或可以接受的Al∶M原子比。
优选的是原料以液态与催化剂接触，并且接触时的反应温度与压力可以在很宽的范围内变化，反应时间根据所期望的反应转化程度来决定。因此，合适的反应温度可以在-60-280℃之间，如20-120℃之间，采用的绝对反应压力可以是1大气压或略低，或者高达500大气压或更高。在一个具体的例子中，原料以液态与金属茂／铝氧烷催化剂接触，并在反应温度在-60-280℃之间，反应压力在1-500大气压之间，通常为1大气压或略高的条件下接触；在此例子中，反应温度优选20-120℃，反应在惰性气氛下进行。再次，采用常规实验手段确定最优或可接受的有关温度、压力和时间等反应条件。
根据本发明的方法，催化剂中的铝氧烷组分溶解在有机溶剂(选用合成铝氧烷组分时所用的溶剂最为方便)中，可以与有机液体中的金属茂组分以良好搅拌的悬浊液相混合，其中所说有机液体对金属茂／铝氧烷催化剂呈惰性；或者方便地为用于二聚反应中的原料形式。当用原料去分散金属茂组分时，只要该混合物与铝氧烷溶液实质上混合均匀，二聚反应就真正开始进行。二聚反应可以方便地在惰性气氛，如氩气下，在大气压下进行。
通过下述非限制性的实施例说明本发明：
实施例1
在室温和氩气氛下，将3．07克的30重％甲基铝氧烷催化剂的甲苯溶液与0．24g的(Cp)2ZrCl2(二氯环戊二烯锆)连续搅拌混合15分钟，得到金属茂／铝氧烷催化剂，催化剂的Al∶Zr原子比是66∶1。
在氩气氛下，在300毫升的消焰Schlenk烧瓶反应器中将31．89g的费托反应C7馏分(包含大约74重％的1-庚烯)和44．82g的费托反应C9馏分(包含大约65重％的1-壬烯)与催化剂混合，随后仍在氩气氛下，在大气压与室温的条件下搅拌4小时，最后用10重％的氯化氢的甲醇溶液中止反应。中止反应后的溶液继续搅拌30分钟，然后水洗、浓缩二聚反应产物。用气相色谱分析浓缩后的水洗产物，得到转化率大于85％，二聚和交叉二聚的产物的摩尔比C14∶C16∶C18为1∶2∶1，其中C14代表二个庚烯分子二聚的产物，C18代表二个壬烯分子二聚的产物，C16代表一个庚烯分子与一个壬烯分子交叉二聚的产物。
实施例2
重复实施例1，但使用3．552g的甲基铝氧烷催化剂与0．22g的(Cp)2ZrCl2，以及79．19g的费托反应C8馏分(包含大约40重％的1-辛烯)。气相色谱分析得到C16产物的转化率大于77％。
本发明的优点是，申请人惊奇地发现高效的二聚反应对α-烯烃原料纯度要求并不很高。未经任何实质处理、纯化与加工的费托反应衍生的包含有相当量的非α-烯烃组分的烯烃原料，可通过选择合适的主要含有所需碳数的α-烯烃馏分用于生产目标二聚物。所说的二聚物具有通式R’R”C=CH2，其中R’和R”为烷基，可以相同或不同，该二聚体由R’=CH2和R”=CH2的α-烯烃形成，一般R’与R”分别是C2-C30烷基，优选C5-C10烷基。
由本发明方法得到二聚反应产物可以用作如加氢甲酰化反应制备氧化产物，如醛或醇的起始原料，这些氧化产物可以用于制造洗涤剂和表面活性剂等。
尽管期望本发明适于使用任何费托反应衍生的烯烃原料，但是与低温，通常在约220℃，进行的费托反应衍生的烯烃原料相比，本发明更适用于在高于280℃进行的费托反应衍生的烯烃原料，优选高于300℃，例如在330℃。

Claims (10)

1．一种从含α-烯烃的烯烃原料生产二聚体的方法。该方法包括将所述原料与金属茂／铝氧烷催化剂接触，通过金属茂催化的二聚反应选择性地使原料中的α-烯烃二聚，该方法的特征在于原料是费托反应衍生的烯烃原料，包括费托反应衍生的烃类混合物，其中含有至多90重％α-烯烃；至少5重％非α-烯烃的烯烃组分，选自直链内烯烃、支链内烯烃、环烯、二烯、三烯及它们的混合物；至少5重％非烯烃组分，选自链烷烃、氧化的烃类、芳烃及它们的混合物，金属茂催化的二聚反应发生时，二聚的烯烃与原料形成混合物。
2．根据权利要求1的方法，其特征在于所述原料包含50-90重％所说的α-烯烃。
3．根据权利要求1或2的方法，其特征在于所述原料包含5-20重％所说非α-烯烃的烯烃。
4．根据权利要求1-3的任一方法，其特征在于所述原料包含5-30重％所说非烯烃组分。
5．前述任一权利要求的方法，其特征在于所述金属茂／铝氧烷催化剂含有甲基铝氧烷的铝氧烷组分；和具有(Cp)2MY2通式的化合物的金属茂组分，其中Cp代表环戊二烯基，M是选自锆、铪和钛的金属，Y是选自氢自由基、卤素自由基、烷基和它们的混合物。
6．根据权利要求5的方法，其特征在于所述金属茂组分包含具有所说(Cp)2MY2通式的单个化合物。
7．根据权利要求5或6的方法，其特征在于所述催化剂的铝氧烷组分中的铝与所述催化剂的金属茂中的金属的原子比Al∶M在1∶1至100∶1之间。
8．前述任一权利要求的方法，其特征在于所述原料以液态与所述金属茂／铝氧烷催化剂接触，接触时反应温度在-60至280℃之间，绝对反应压力在1-500大气压之间。
9．根据权利要求8的方法，其特征在于所述反应温度在20-120℃之间，反应在惰性气氛下进行。
10．根据权利要求1的方法，该方法参照实施例于此进行充分描述。
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