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CN102227489A - 通过氧解反应用天然油原料制备喷气式发动机燃料的方法 - Google Patents

通过氧解反应用天然油原料制备喷气式发动机燃料的方法 Download PDF

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CN102227489A
CN102227489A CN2009801472878A CN200980147287A CN102227489A CN 102227489 A CN102227489 A CN 102227489A CN 2009801472878 A CN2009801472878 A CN 2009801472878A CN 200980147287 A CN200980147287 A CN 200980147287A CN 102227489 A CN102227489 A CN 102227489A
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jet fuel
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fuel composition
oxygen
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CN102227489B (zh
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梅尔·卢肯斯
史蒂文·科亨
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Elevance Renewable Sciences Inc
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Abstract

本发明提供了一种用含有天然油的原料制备喷气式发动机燃料组合物的方法。该方法包括使原料与氧在足以形成氧解产物的条件下反应。该方法进一步包括在足以形成喷气式发动机燃料组合物的条件下使所述氧解产物氢化。

Description

通过氧解反应用天然油原料制备喷气式发动机燃料的方法
技术领域
本申请涉及一种通过天然原料的氧解反应(oxygen-cleaved reactions)来制备喷气式发动机燃料的方法。
背景技术
臭氧解(Ozonolysis)是本领域广为人知的化学反应。臭氧解是烯烃与臭氧的反应，其中不饱和的碳碳双键断裂并由与氧相连的双键代替，如下列方程式I所表示：
Figure BPA00001374478400011
其中R1、R2、R3和R4是有机基团或氢。
氧化裂解也是本领域广为人知的化学过程。涉及烯烃化合物的氧化裂解反应条件的实例在美国专利5596111和5939572中有所描述，它们都通过引用结合于此。在氧化裂解反应中，通过烯烃化合物与氧在过氧化物、溶剂以及无机氧化物催化剂存在下反应来制备羧酸，如下列方程式所示：
其中R1、R2、R3和R4是有机基团或氢。
近年来，对那些通常衍生自原油的材料的环境友好制备技术的需求增加。例如，研究人员已经研究了使用天然原料(例如植物油和种子油)制造生物燃料、蜡、塑料等的可行性。
感兴趣的天然原料包括，例如：天然油(例如植物油、鱼油、动物油脂)以及天然油的衍生物，例如脂肪酸和脂肪酸烷基(例如甲基)酯。通过许多不同的反应，可以将这些原料转化为工业有用的化学品(例如蜡、塑料、化妆品、生物燃料等)。
近年来，对基于石油的运输燃料的需求有所增长。人们担心世界的石油产量可能无法满足需求。此外，对基于石油的运输燃料的增长性需求导致更多温室气体的产生。具体地，在美国航空业对产生的温室气体的贡献超过10％。由于对燃料的增长性需求以及温室气体的产量增加，需要探索制备环境友好、替代性燃料源的方法。具体地，需要探索用天然原料制备环境友好喷气式发动机燃料的方法。
发明概述
本发明公开了通过氧解反应(例如臭氧解或氧化裂解)用天然油制备喷气式发动机燃料的方法。
根据本发明，包含天然油的原料与氧在足以形成氧解产物的条件下反应。该方法进一步包括在足以形成喷气式发动机燃料组合物的条件下使氧解产物氢化。
一方面，所述方法包括含天然油的原料(例如豆油)与臭氧在足以形成臭氧解产物的条件下反应。该方法进一步包括在足以形成喷气式发动机燃料组合物的条件下使臭氧解产物氢化。
另一方面，所述方法包括含天然油的原料(例如豆油)与氧在足以形成氧化裂解产物的条件下反应。该方法进一步包括在足以形成喷气式发动机燃料组合物的条件下使氧化裂解产物氢化。
附图说明
图1是用天然油与臭氧反应制备喷气式发动机燃料组合物的过程的示意图。
图2是用天然油与氧气反应制备喷气式发动机燃料组合物的过程的示意图。
发明详述
本发明涉及用天然油原料制备喷气式发动机燃料的方法。
在本文中使用时，单数形式“一”、“一个”和“该”包括复数对象，除非上下文中明确规定。例如，提到“取代基”时既包括一个取代基也包括两个或更多个取代基等。
在本文中使用时，术语“例如”、“比如”、“诸如”或“包括”指的是引入例子进一步详细地说明主题。除非特别说明，提供的这些例子仅用于帮助理解本发明公开内容描述的申请，并不想限定为任何形式。
在本文中使用时，术语“天然油”、“天然原料”或“天然油原料”指的是衍生自植物源或动物源的油。术语“天然油”包括天然油的衍生物，除非特别指出。天然油的例子包括，但不限于：植物油、藻油、动物油脂、松浆油、这些油的衍生物以及这些油的任意组合等。植物油的代表性例子包括低芥酸菜籽油、菜籽油、椰子油、玉米油、棉籽油、橄榄油、棕榈油、花生油、红花油、芝麻油、豆油、葵花油、亚麻籽油、棕榈仁油、桐油、麻风树油、蓖麻油。动物油脂的代表性例子包括猪脂、牛脂、鸡脂、黄油和鱼油。松浆油是木纸浆产品的副产物。
在本文中使用时，术语“天然油的衍生物”指的是使用化学领域一种已知方法或多种已知方法的组合从天然油中衍生的化合物或化合物的混合物。这些方法包括皂化、支化、氢化(部分或全部)、异构化、氧化和环氧。天然油的衍生物可以是衍生自天然油甘油酯的脂肪酸甲酯(FAME)。天然油衍生物的代表性例子包括树胶、磷脂、皂脚、酸化皂脚、油泥蒸馏物、天然油的脂肪酸和脂肪酸烷基(例如甲基)酯。例如，天然油衍生物可以是衍生自天然油甘油酯的脂肪酸甲酯(FAME)。在一些优选的实施方式中，原料包括低芥酸菜籽油或豆油，例如精炼的、脱色的和脱臭的豆油(即RBD豆油)。豆油是甘油的不饱和多元醇酯，其通常包含约95重量％或更多(例如99重量％或更多)的脂肪酸甘油三酯。豆油的多元醇酯中主要的脂肪酸包括饱和脂肪酸，例如棕榈酸(十六烷酸)和硬脂酸(十八烷酸)；以及不饱和脂肪酸，例如油酸(9-十八烯酸)、亚油酸(9，12-十八碳二烯酸)和亚麻酸(9，12，15-十八碳三烯酸)。
在本文中使用时，术语“产量”可以指用氧解反应和氢化反应制备的喷气式发动机燃料的总重量。还可以定义为产率％的形式，其中用制备的喷气式发动机燃料的总重量除以天然油原料的总重量。还可以指分离步骤和/或异构化反应后喷气式发动机燃料的总重量。
在本文中使用时，术语“氧解产物”既可以指“臭氧解产物”又可以指“氧化裂解产物”。
在本文中使用时，术语“氧”可以指臭氧(O3)、氧气(O2)或元素氧(O)。
在本文中使用时，术语“臭氧解产物”指的是烯烃与臭氧在足以使不饱和碳碳双键裂解且用与氧相连的双键代替的条件下的反应产物。
在本文中使用时，术语“氧化裂解产物”指的是烯烃与氧气在足以使不饱和碳碳双键裂解且用与氧相连的双键或羧基代替的条件下的反应产物。
在本文中使用时，术语“异构化反应”、“异构体”或“异构化”指的是直链烃类化合物(例如正链烷或正烯烃)向支化的烃类化合物(例如异链烷烃或异烯烃)的反应和转化。例如，正戊烷可以异构化为正戊烷、2-甲基丁烷和2，2-二甲基丙烷的混合物。正链烷或正烯烃的异构化可用于改善燃料组合物的总体性能。
在本文中使用时，术语“产量”可以指用氧解反应和氢化反应制备的喷气式发动机燃料的总重量。还可以指分离步骤和/或异构化反应后喷气式发动机燃料的总重量。还可以定义为产率％的形式，其中用制备的喷气式发动机燃料的总重量除以天然油原料和低分子量烯烃的总重量。
在本文中使用时，术语“喷气式发动机燃料”或“航空燃料”可以指煤油型或石脑油型的燃料油分，或军用级喷气式发动机燃料组合物。“煤油型”喷气式发动机燃料(包括Jet A和Jet A-1)的碳数分布介于约8和16之间。Jet A和Jet A-1的闪点通常介于38℃和66℃之间，自燃温度约为210℃，冰点介于约-47℃和-40℃之间，15℃时的密度约为0.8g/cc，能量密度约为42.8-43.2MJ/kg。“石脑油型”或“宽馏分”喷气式发动机燃料(包括Jet B)的碳数分布介于约5和15之间。Jet B的闪点通常介于-23℃和0℃之间，自燃温度约为250℃，冰点约为-65℃，密度约为0.78g/cc，能量密度约为42.8-43.5MJ/kg。“军用级”喷气式发动机燃料指的是喷气式飞机燃料或“JP”编号的体系(JP-1，JP-2，JP-3，JP-4，JP-5，JP-6，JP-7，JP-8等)。为了应对超音速飞行中承受的热量和压力，军用级喷气式发动机燃料可以包含可选或附加的添加剂来获得比Jet A、Jet A-1或Jet B更高的闪点。此外，燃料组合物通常可以指满足所需规格的材料或用于配制燃料组合物但其本身无法满足燃料所有所需规格的混合物组分。
在本文中使用时，术语“碳数分布”可以指存在于组合物中的化合物的范围，其中每一种化合物都由存在的碳原子数确定。例如，喷气式发动机燃料通常包括烃类化合物的分布，其中多数化合物中每一个都具有5-16个碳原子。
在本文中使用时，术语“能量密度”可以指单位质量(MJ/kg)或单位体积(MJ/L)的给定体系中存储能量的大小。例如，喷气式发动机燃料的能量密度通常大于40MJ/kg。
根据本发明，在一个实施方式中，可以通过天然油与臭氧反应产生高产率的喷气式发动机燃料组合物。
如图1所示，天然油12与臭氧14在反应器20中混合。臭氧解用的典型的反应条件在本领域是众所周知的，如美国专利3481954、3868392和4085127中描述的，它们都通过引用结合于此。优选地，天然油是植物油或植物油衍生物，例如豆油。
反应器20中的臭氧解反应产生臭氧解产物22。在一个实施方式中，基于臭氧解产物22的质量，优选使臭氧解产物22异构化来帮助实现期望喷气式发动机燃料的性能(例如闪点、冰点或能量密度)的目标。异构化反应在本领域是众所周知的，如美国专利3150205、4210771、5095169和6214764中描述的，它们都通过引用结合于此。该阶段的异构化反应还可以使C18+化合物裂解，并且有助于制备出含有期望的5-16碳数范围内化合物的喷气式发动机燃料组合物。
在一个实施方式中，将臭氧解产物22送入氢化单元30中。在某些实施方式中，优选在引入氢化单元30之前，从臭氧解产物22中分离副产物。
在氢化单元，氢气24与臭氧解产物22在氢化单元30中反应。在氢化过程中，来自臭氧解产物22的醛被氢气24还原。此外，天然油的酯、酸和醇被还原为烃。产生的氢化产物32包括分布优选集中在约C9烃的烃类。氢化产物32还可以包含来自氢化反应和臭氧解反应的副产物，包括水和重烃链(C18+)。氢化步骤的工艺条件在本领域是众所周知的，如PCT/EP2007/009668中讨论的。
氢化产物32可以充当喷气式发动机燃料组合物。或者，可以将氢化产物32送入分离单元40来从期望的喷气式发动机燃料组合物42中除去任何一种副产物44(即水、C18+)。在一个实施方式中，可以将氢化产物32分成目标喷气式发动机燃料组合物级分42、轻尾级分(未示)和重尾副产物级分(如该实施方式所示的44)。氢化产物32可以包含来自臭氧解反应的副产物，如果氢化步骤之前没有进行分离步骤，可以在这一阶段分离所述副产物。在一个实施方式中，使用蒸馏来分离各级分。或者，通过将氢化产物32冷却至约38-66℃或-47-40℃，或-65℃，可以使重尾副产物级分从目标喷气式发动机燃料组合物级分中分离，然后通过本领域已知的技术(例如过滤或离心)除去固体级分。
在另一个实施方式中，基于氢化产物32或喷气式发动机燃料组合物42的质量，可能需要进一步处理，以实现期望的喷气式发动机燃料性能(例如闪点、冰点或能量密度)的目标。例如，可能需要使氢化产物32或喷气式发动机燃料组合物42中的正链烷烃异构化，并产生正链烷烃化合物和异链烷烃化合物的混合物。异构化反应在本领域是众所周知的，例如美国专利3150205、4210771、5095169和6214764中所描述的，它们都通过引用结合于此。
在一个实施方式中，天然油的臭氧解可以产生含至少20wt％C9化合物的喷气式发动机燃料。更优选，臭氧解可以产生含至少30、40或50wt％C9化合物的喷气式发动机燃料。在这些实施方式中，不同的性能参数用于特定类型的喷气式发动机燃料。
在另一实施方式中，如图2所示，通过天然油与氧气在足以使天然油的烯烃裂解的条件下反应产生高产率的喷气式发动机燃料组合物。氧化裂解反应的典型条件在本领域是已知的，例如美国专利5596111、5864049和5939572中描述的，它们都通过引用结合于此。例如，反应器120中的天然油112与氧气114可以在有机溶剂、无机氧化物催化剂以及过氧化物(例如过氧化氢)的存在下反应。优选地，天然油112是植物油或植物油衍生物，例如豆油。
反应器120中的氧化裂解反应产生氧化裂解产物122。在一个实施方式中，基于氧化裂解产物122的质量，优选使氧化裂解产物122异构化来帮助实现期望喷气式发动机燃料的性能(例如闪点、冰点或能量密度)的目标。异构化反应在本领域是众所周知的，如美国专利3150205、4210771、5095169和6214764中描述的，它们都通过引用结合于此。该阶段的异构化反应还可以使C18+化合物裂解，并且有助于制备出含有期望的5-16碳数范围内化合物的喷气式发动机燃料组合物。
在一个实施方式中，将氧化裂解产物122送入氢化单元130。在某些实施方式中，优选在引入氢化单元130之前，从氧化裂解产物122中分离副产物。
氢气124与氧化裂解产物122在氢化单元130中反应。在氢化过程中，来自氧化裂解产物122的羧酸和醛被氢气124还原。此外，天然油的酯、酸和醇被还原为烃。产生的氢化产物132包括分布优选集中在约C9烃的烃类。氢化产物132还可以包含来自氢化反应和氧化裂解反应的副产物，包括水和重烃链(C18+)。氢化步骤的工艺条件在本领域是众所周知的，如PCT/EP2007/009668中讨论的。
氢化产物132可以充当喷气式发动机燃料组合物。或者，可以将氢化产物132送入分离单元140以从期望的喷气式发动机燃料组合物142中除去任何一种副产物144(即水、C18+)。在一个实施方式中，可以将氢化产物132分成目标喷气式发动机燃料组合物级分142、轻尾级分(未示)、重尾副产物级分(如该实施方式所示的144)。氢化产物132可以包含来自氧化裂解反应的副产物，如果氢化步骤之前没有进行分离步骤，可以在这一阶段分离出所述副产物。在一个实施方式中，使用蒸馏来分离各级分。或者，通过将氢化产物132冷却至约38-66℃或-47-40℃，或-65℃，可以使重尾副产物级分从目标喷气式发动机燃料组合物级分中分离，然后通过本领域已知的技术(例如过滤或离心)除去固体级分。
在另一个实施方式中，基于氢化产物132或喷气式发动机燃料组合物142的质量，可能需要进一步处理，以实现期望的喷气式发动机燃料性能(例如闪点、冰点或能量密度)的目标。例如，可能需要使氢化产物132或喷气式发动机燃料组合物142中的正链烷烃异构化，并产生正链烷烃化合物和异链烷烃化合物的混合物。
如下表所示，某些天然油的氧化裂解可以产生含至少40wt％C9化合物的喷气式发动机燃料组合物。或者，对某些天然油来说，喷气式发动机燃料可能包含多于50wt％的C12化合物。在这些实施方式中，不同的性能参数用于特定类型的喷气式发动机燃料。
在一个实施方式中，天然油转化为包含介于8-16碳数的碳数分布的煤油型喷气式发动机燃料。该煤油型喷气式发动机燃料包括Jet A或Jet A-1。在该实施方式中，优选地，其闪点介于约38和66℃之间。还优选自燃温度为约210℃。还优选冰点介于约-47℃和-40℃之间(对于Jet A-1型燃料来说接近-47℃而对于Jet A型燃料来说接近-40℃)。还优选15℃时的密度为约0.8g/cc。还优选能量密度大于40MJ/kg。更优选能量密度介于42和48MJ/kg之间。甚至更优选煤油型喷气式发动机燃料的能量密度为约42.8-43.2MJ/kg。
通过天然油与臭氧反应来实现期望的喷气式发动机燃料性能以及期望的介于C8和C16的分布，目标为获得煤油型喷气式发动机燃料。
在另一个实施方式中，天然油转化为包含介于5-15碳数的碳数分布的石脑油型喷气式发动机燃料。该石脑油型喷气式发动机燃料包括Jet B。在该实施方式中，优选地，其闪点介于约-23℃和0℃之间。还优选自燃温度为约250℃。还优选冰点为约-65℃。还优选15℃时的密度为约0.78g/cc。还优选能量密度大于40MJ/kg。更优选能量密度介于42和48MJ/kg之间。甚至更优选石脑油型喷气式发动机燃料的能量密度为约42.8-43.5MJ/kg。
通过天然油与臭氧反应来实现期望的喷气式发动机燃料性能以及期望的介于C5和C15的分布，目标为获得石脑油型喷气式发动机燃料。
将通过下列非限制性实施例描述本发明。
实施例
各种天然油与氧气在足以使天然油通过氧化裂解反应转化为羧酸和醛的条件下反应。随后氧化裂解产物与氢气在足以使氧化裂解产物转化为烃的条件下反应。如此获得的来自各种天然油的烃的分布如下图所示，并与来自化石燃料的典型喷气式发动机燃料的分布对比。
表
Figure BPA00001374478400091
尽管已经详细描述了本发明的实施方式，但是所描述的发明可能具有修正和变化的形式。尽管根据非限制性实施例对本发明进行描述，但是当然应当理解到本发明不应局限于此，因为本领域普通技术人员特别根据上述教导可以进行各种修正。

Claims (17)

1.一种制备喷气式发动机燃料组合物的方法，其包括：
提供包含天然油的原料；
使所述原料与氧在足以形成氧解产物的条件下反应；并且
在足以形成喷气式发动机燃料组合物的条件下使所述氧解产物氢化，
其中所述喷气式发动机燃料组合物包含碳数分布介于5到16个碳数的烃。
2.如权利要求1所述的方法，其中所述喷气式发动机燃料组合物的能量密度大于约40MJ/kg。
3.如权利要求1所述的方法，其进一步包括在氢化之前使所述氧解产物异构化。
4.如权利要求1所述的方法，其进一步包括使所述喷气式发动机燃料组合物异构化，其中所述喷气式发动机燃料组合物中的正链烷烃化合物被异构化为异链烷烃化合物。
5.如权利要求1所述的方法，其进一步包括从所述喷气式发动机燃料组合物中分离出C18+化合物和水。
6.如权利要求5所述的方法，其中通过至少下列方法中的一种来除去所述C18+化合物：蒸馏、过滤或离心。
7.如权利要求1所述的方法，其中所述喷气式发动机燃料组合物是煤油型喷气式发动机燃料，并且其中的碳数分布介于8和16个碳数之间。
8.如权利要求7所述的方法，其中所述煤油型喷气式发动机燃料为：闪点介于约38℃和66℃之间；自燃温度为约210℃；并且冰点介于约-47℃和-40℃之间。
9.如权利要求1所述的方法，其中所述喷气式发动机燃料组合物是石脑油型喷气式发动机燃料，并且其中的碳数分布介于5和15个碳数之间。
10.如权利要求9所述的方法，其中所述石脑油型喷气式发动机燃料为：闪点介于约-23℃和0℃之间；自燃温度为约250℃；冰点为约-65℃。
11.如权利要求1所述的方法，其中所述喷气式发动机燃料组合物含有大约超过20wt％的C9化合物。
12.如权利要求1所述的方法，其中所述喷气式发动机燃料组合物含有大约超过40wt％的C9化合物。
13.如权利要求1所述的方法，其中所述喷气式发动机燃料组合物含有大约超过50wt％的C12化合物。
14.如权利要求1所述的方法，其中所述原料包含一种或更多种选自由下列物质组成的组中的油：藻油、低芥酸菜籽油、菜籽油、椰子油、玉米油、棉籽油、橄榄油、棕榈油、花生油、红花油、芝麻油、豆油、葵花油、亚麻籽油、棕榈仁油、桐油、麻风树油、蓖麻油以及这些中一种或更多种的天然油衍生物。
15.如权利要求1所述的方法，其中所述原料包含豆油、豆油衍生物或它们的组合。
16.一种制备喷气式发动机燃料组合物的方法，其包括：
提供包含天然油的原料；
使所述原料与臭氧在足以形成臭氧解产物的条件下反应；并且
在足以形成喷气式发动机燃料组合物的条件下使所述臭氧解产物氢化，
其中所述喷气式发动机燃料组合物包含碳数分布介于5到16个碳数的烃。
17.一种制备喷气式发动机燃料组合物的方法，其包括：
提供包含天然油的原料；
使所述原料与氧气在足以形成氧化裂解产物的条件下反应；并且
在足以形成喷气式发动机燃料组合物的条件下使所述氧化裂解产物氢化，
其中所述喷气式发动机燃料组合物包含碳数分布介于5到16个碳数的烃。
CN200980147287.8A 2008-11-26 2009-11-25 通过氧解反应用天然油原料制备喷气式发动机燃料的方法 Expired - Fee Related CN102227489B (zh)

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