CN113528176B - 一种生物质液体燃料的制备方法 - Google Patents
一种生物质液体燃料的制备方法 Download PDFInfo
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- CN113528176B CN113528176B CN202110514662.0A CN202110514662A CN113528176B CN 113528176 B CN113528176 B CN 113528176B CN 202110514662 A CN202110514662 A CN 202110514662A CN 113528176 B CN113528176 B CN 113528176B
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- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
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- 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
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
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- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明公开了一种生物质液体燃料的制备方法,将双酚A溶于正丁醇中反应后加入醛,蒸出正丁醇溶剂后煅烧、研磨、过筛得到聚合物加入酸反应后得固体酸催化剂,将氢氧化铝加入磷酸溶解后加去离子水反应后过滤、烘干得前驱体煅烧得磷酸铝分子筛加入硝酸镍溶液中浸渍,然后干燥、煅烧即得镍负载的磷酸铝催化剂用于烷基化反应产物进行加氢脱氧反应获得高产率的柴油或航空煤油烷烃。本发明将双酚A衍生的酸性树脂作为固体酸用于木质纤维素基甲基呋喃与羰基化合物之间的烷烃化反应,并在这些反应中表现了很好的活性和稳定性,通过这些反应可获得一系列碳数为13~16的含氧有机化合物,这些化合物可通过加氢脱氧获得符合柴油和航空煤油结构要求的支链烷烃。
Description
技术领域
本发明涉及生物质能源技术领域,尤其涉及一种生物质液体燃料的制备方法。
背景技术
能源是人类社会赖以生存和发展的重要物质基础。进入21世纪航空运输业发展迅速,在经济发展和国家安全方面占有重要地位。因此,高品质航空燃油的安全及稳定供应至关重要。目前航空燃油主要来源于煤、石油等不可再生的化石能源,同时,石化基航空燃料的燃烧会排放大量的温室气体二氧化碳导致气候变暖等环境问题,不能满足人类长期、可持续的发展要求。这些因素制约着航空工业的发展。因此,寻求新型、清洁、可再生的新能源已成为能源领域的研究重点。生物质作为一种可再生的有机碳源成为目前的热点研究。
双酚A是重要的有机化工原料,由苯酚和丙酮反应所得,主要用于生产聚碳酸酯、环氧树脂、聚砜树脂、聚苯醚树脂等多种高分子材料。也可用在增塑剂、阻燃剂、抗氧剂、热稳定剂、橡胶防老剂、农药、涂料等精细化工产品,具有广阔的发展前景。
发明内容
本发明的目的就在于为了解决上述问题而提供一种生物质液体燃料的制备方法。
本发明通过以下技术方案来实现上述目的:
本发明包括以下步骤:
S1:将双酚A溶于10mL的正丁醇中,在带有冷凝管、温度计的圆底烧瓶中反应,待双酚A溶解完全,溶液呈透明色,后加入醛,并控制醛和双酚A的质量比为l.0:1.6;混合均匀后反应6h,待反应完毕,用旋转蒸发器蒸出正丁醇溶剂,然后煅烧,研磨、过筛、得到聚合物。
S2:称取聚合物加入酸,搅拌,室温反应1~12h后用冰水淬灭,过滤,用去离子水洗涤至pH为中性,烘干,即得固体酸催化剂,
S3:将氢氧化铝置于反应釜中加入磁子搅拌,在95℃下滴加入85%的磷酸,完全溶解后,加去离子水,反应12小时后过滤,在120℃烘干2小时得前驱体;将获得的前驱体在马弗炉内煅烧4小时,得磷酸铝分子筛;
S4:称取分子筛加入硝酸镍溶液中,浸渍12h,然后在120℃干燥12小时,在500℃煅烧4小时,使用前在500℃氢气氛围下还原2h,即得镍负载的磷酸铝催化剂用于烷基化反应产物进行加氢脱氧反应获得高产率的柴油或航空煤油烷烃。
本发明的有益效果在于:
本发明是一种生物质液体燃料的制备方法,与现有技术相比,本发明将双酚A衍生的酸性树脂作为固体酸用于木质纤维素基甲基呋喃与羰基化合物之间的烷烃化反应,并在这些反应中表现了很好的活性和稳定性,通过这些反应可获得一系列碳数为13~16的含氧有机化合物,这些化合物可通过加氢脱氧获得符合柴油和航空煤油结构要求的支链烷烃。
附图说明
图1是甲基呋喃与不同底物的反应线路图;
图2为本发明中5,5'-(呋喃-2,2-二基)双(2-甲基呋喃)的1HNMR图;
图3为甲基呋喃与2-戊酮反应产物的1HNMR图;
图4为甲基呋喃与环戊酮反应产物的1HNMR图;
图5为甲基呋喃与2-丁酮反应产物的1HNMR谱图;
图6为甲基呋喃与环己酮反应产物的1HNMR谱图;
图7为甲基呋喃与丙酮反应产物的1HNMR图。
具体实施方式
下面结合附图对本发明作进一步说明:
首先,将双酚A溶于10mL的正丁醇中,在带有冷凝管、温度计的圆底烧瓶中反应,待双酚A溶解完全,溶液呈透明色,后加入一定量醛,并控制醛和双酚A的用量比为l.0:1.6(质量比)。所用醛为多聚甲醛、甲醛、乙醛、丁醛、糠醛中的一种或两种以上,优选多聚甲醛。混合均匀后反应6h,待反应完毕,用旋转蒸发器蒸出正丁醇溶剂,然后煅烧,研磨、过筛、得到聚合物。聚合反应酸可为无机酸和有机酸。无机酸为氯磺酸、磷钨酸、硫酸、硝酸、磷酸中的一种或两种以上;有机酸为三氟乙酸、甲磺酸、对甲苯磺酸中的一种或两种以上。在聚合反应中,酸与双酚A的用量比为0.01~0.15:1,反应温度为20~100℃,反应时间为0.5~24小时;缩合反应所得聚合物在100~400℃温度下煅烧2小时,称取一定量的聚合物加入氯磺酸,搅拌,室温反应1~12h后用冰水淬灭,过滤,用去离子水洗涤至pH为中性,烘干,即得固体酸催化剂,所用氯磺酸浓度为0.1~4mol/L。此外,聚合物与酸比为1.0g:1.0~10.0mL酸溶液。酸化条件为20~120℃下酸化1~12小时。
本专利合成的固体酸催化剂可用于木质纤维素基甲基呋喃和羰基化合物之间烷烃化反应。木质纤维素基羰基化合物为糠醛、5-羟甲基糠醛、丙酮、2-丁酮、环戊酮、2-戊酮、环己酮中的一种或两种以上的混合物。
将反应底物先后加入圆底烧瓶中,控制甲基呋喃与羰基化合物的摩尔比为2:1。烷基化反应温度为20~100℃,催化剂用量与呋喃化合物比为0.01~0.5:1,反应时间为0.5~12小时,优选2~3小时。烷基化反应产物为碳数在13~16之间的含氧化合物,这些含氧化合物经加氢脱氧制成柴油或航空煤油烷烃。
将氢氧化铝置于反应釜中加入磁子搅拌,在95℃下滴加入一定量的磷酸(85%),完全溶解后,加一定量的去离子水,反应12小时后过滤,在120℃烘干2小时得前驱体;将获得的前驱体在马弗炉内煅烧4小时,得磷酸铝分子筛。称取一定量的分子筛加入一定浓度的硝酸镍溶液中,浸渍12h,然后在120℃干燥12小时,在500℃煅烧4小时,使用前在500℃氢气氛围下还原2h,即得镍负载的磷酸铝催化剂。用于烷基化反应产物进行加氢脱氧反应。
加氢脱氧反应在间歇式釜式反应器中进行,釜式反应器中的反应条件为:反应温度150~300℃,反应时间为6~24h,氢气压力为0.5至10.0MPa,加氢脱氧反应体系中反应原料的质量浓度优选5~15%。
如图1-7所示:
实施例1~83
1、固体酸催化剂的制备及烷基化反应
1)在以下实施例中,将3.0g双酚A溶于10mL的醇溶剂中,然后加入1.80g醛,然后向该混合物中加入0.30g对甲苯磺酸进行聚合反应。在设定温度和设定时间下反应。反应完毕旋蒸出溶剂、120℃干燥4h、在设定温度下煅烧4h,研磨后称取1.0g聚合物,加入1.0mL氯磺酸反应4h。酸化所得酸性树脂经抽滤、洗涤至中性、80℃干燥之后即为所得催化剂。
烷基化反应在圆底烧瓶中进行。向50mL的圆底烧瓶中加入0.05g催化剂、1.64g2-甲基呋喃和0.96g糠醛在设定的恒温油浴下搅拌反应2小时。通过高效液相色谱(HPLC)对反应产物进行定量分析。
不同条件下制得的固体酸催化甲基呋喃与糠醛烷基化反应的影响,反应结果如表1。
表1.不同反应条件下制得的固体酸催化剂对烷基化反应的影响
从表1中可以看出:双酚A与多聚甲醛、甲醛、乙醛、丁醛、糠醛等在不同溶剂(正丁醇、丙醇、异丙醇、异丁醇、戊醇、己醇),氯磺酸、磷钨酸、硫酸、硝酸、磷酸、三氟乙酸、甲磺酸、对甲苯磺酸等酸催化的聚合反应的产物制得的固体酸催化剂。所得的催化剂用于催化甲基呋喃与糠醛的反应均有一定的催化活性,5,5'-(呋喃-2,2-二基)双(2-甲基呋喃)的产率从28.2%到98.3%。
2)在以下实施例中,将3.0g双酚A溶于10mL的正丁醇中,然后加入1.80g多聚甲醛,然后向该混合物中加入0.30g对甲苯磺酸进行聚合反应。在设定的90℃温下反应6h。反应完毕旋蒸出溶剂、120℃干燥4h、在180℃下煅烧4h,研磨后用一定量氯磺酸溶液进行磺化处理。考查磺酸化剂用量、种类、温度和时间等条件下制得的催化剂的烷基化活性。
烷烃化反应在配有冷凝回流装置的圆底烧瓶中进行。向50mL的圆底烧瓶中加入0.05g催化剂、1.64g 2-甲基呋喃和0.96g糠醛在设定的恒温油浴下搅拌反应2.0小时。通过高效液相色谱(HPLC)对反应产物进行定量分析。反应结果见表2。
表2.不同酸化处理下对所合成催化剂活性的影响
从表2中可以看出,氯磺酸和硫酸均对双酚A与多聚甲醛反应合成的聚合物有一定的磺化能力。制得的固体酸对甲基呋喃和糠醛的烷基化均有一定的反应活性。5,5'-(呋喃-2,2-二基)双(2-甲基呋喃)的产率从63.3%到98.4%。
3)在以下实施例中,将3.0g双酚A溶于10mL的正丁醇中,然后加入1.80g多聚甲醛,然后向该混合物中加入0.30g对甲苯磺酸进行聚合反应。在90℃温下反应6h。反应完毕旋蒸出溶剂、120℃干燥4h、在180℃下煅烧4h,研磨后称取1.0g聚合物加入1.0mL的氯磺酸,在25℃反应6h。在此条件下制备的固体酸用于烷基化反应的条件优化。
烷烃化反应在配有冷凝回流装置的圆底烧瓶中进行。向50mL的圆底烧瓶中加入0.05g催化剂、1.64g 2-甲基呋喃和0.96g糠醛在设定的恒温油浴下搅拌反应2.0小时。通过高效液相色谱(HPLC)对反应产物进行定量分析。反应结果见表3。
表3.催化剂用量、反应温度、反应时间对催化活性的影响
注:实施例中反应物2-甲基呋喃和糠醛摩尔比为2:1,催化剂用量0.05g,催化剂选择180℃煅烧的催化剂,反应时间2小时。
从实施例57-83可以看出,在无溶剂下反应,2-甲基呋喃和糠醛摩尔比为2:1,反应物用量2-甲基呋喃1.64g,糠醛0.96g,催化剂用量0.05g条件下,2-甲基呋喃的转化率和5,5'-(呋喃-2,2-二基)双(2-甲基呋喃)的产率达最佳。
在优化的条件下,用所得固体酸催化甲基呋喃与丙酮、2-丁酮、2-戊酮、环戊酮、环己酮、5-羟甲基糠醛的烷基化反应。反应结果如图1所示。
从图1可以看出,2-甲基呋喃与糠醛、5-羟甲基糠醛、丙酮、丁酮、2-戊酮、环戊酮和环己酮的烷烃化反应中,反应活性顺序为:糠醛>5-羟甲基糠醛>环己酮>2-戊酮>丙酮>2-丁酮>环戊酮。5,5'-(呋喃-2-基亚甲基)双(2-甲基呋喃)的产率为98.5%、(5-(双(5-甲基呋喃-2-基)甲基)呋喃-2-基)甲醇的产率为92.8%、5,5'-(丙烷-2,2-二基)双(2-甲基呋喃)的产率为55.1%、5,5'-(环己烷-1,1-二基)双(2-甲基呋喃)的产率80.5%、5,5'-(环戊烷-1,1-二基)双(2-甲基呋喃)的产率79.3%、5,5'-(戊烷-2,2-二基)双(2-甲基呋喃)的产率为67.5%、5,5'-(丁烷-2,2-二基)双(2-甲基呋喃)的产率为60.5%。
2、加氢脱氧中负载型金属催化剂的制备
实施例97~127
将3.0g氢氧化铝置于反应釜中加入磁子搅拌,后加入4.7g磷酸(85%)在95℃下反应12小时,过滤,在120℃干燥4h,在设定温度(400~900℃)的马弗炉中煅烧4h,得氯酸铝载体。
用浸渍法制取金属负载的磷酸铝催化剂。称取0.50g六水硝酸镍溶于1.6mL水中,加入2.0g磷酸铝,搅拌、静置12h,120℃干燥4h,然后在500℃煅烧4小时,使用前在500℃氢气氛围下还原2h,获得催化剂Ni/AlPO4。
Co/AlPO4、Ru/AlPO4、Pd/AlPO4、Pt/AlPO4的制备方法同Ni/AlPO4的制备方法相同。
典型反应:将0.50g的烷烃化反应产物(a)、0.20g催化剂和10mL环己烷装入50mL反应釜中,向反应器中充入氢气置换釜中空气3~4后,充入5.0MPa氢气。在220℃反应24h。反应完毕后进气相色谱进行分析计算产率。不同催化剂、不同反应时间、不同反应压力、不同反应温度等参数对加氢脱氧反应结果如下表所示:
表7.不同反应条件对加氢脱氧反应活性的影响
注:镍的担载为5.0%,环己烷为溶剂,每次用量为10mL。
表8.不同金属、不同担载量对加氢脱氧反应的应用
注:环己烷为溶剂,每次用量为10mL。
由实施例97-127中可知,5,5'-(呋喃-2,2-二基)双(2-甲基呋喃)在不同催化剂中进行加氢脱氧反应,C9-C15烷烃的产率可达96.5%。该产物可以作为航空航天燃料直接使用,或者作为提高十六烷值的添加剂,以一定比例加入到现有的航空航天燃料中使用。
以上显示和描述了本发明的基本原理和主要特征及本发明的优点。本行业的技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不脱离本发明精神和范围的前提下,本发明还会有各种变化和改进,这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等效物界定。
Claims (2)
1.一种柴油或航空煤油的制备方法,其特征在于,包括以下步骤:
S1:将双酚A溶于10mL的正丁醇中,在带有冷凝管、温度计的圆底烧瓶中反应,待双酚A溶解完全,溶液呈透明色,后加入多聚甲醛,并控制多聚甲醛和双酚A的质量比为0.6:1;混合均匀后加入对甲苯磺酸在90℃下反应6h,待反应完毕,用旋转蒸发器蒸出正丁醇溶剂,然后在150-200℃下煅烧4h,研磨、过筛、得到聚合物;
S2:称取聚合物加入氯磺酸溶液,搅拌,在25-40℃下反应2-6h后用冰水淬灭,过滤,用去离子水洗涤至pH为中性,烘干,即得固体酸催化剂,所述步骤S2所用氯磺酸溶液浓度为0.1~4mol/L;聚合物与氯磺酸溶液之比为1.0g:1.0~4.0mL;
S3:将氢氧化铝置于反应釜中加入磁子搅拌,在95℃下滴加入85%的磷酸,完全溶解后,加去离子水,反应12小时后过滤,在120℃烘干2小时得前驱体;将获得的前驱体在马弗炉内煅烧4小时,得磷酸铝分子筛;氢氧化铝与磷酸质量比为3:4.7;
S4:称取分子筛加入硝酸镍溶液中,浸渍12h,然后在120℃干燥12小时,在500℃煅烧4小时,使用前在500℃氢气氛围下还原2h,即得镍负载的磷酸铝催化剂;催化剂中镍的负载量为5%或10%;
S5:将木质纤维素基甲基呋喃和羰基化合物在所述固体酸催化剂的存在下进行烷基化反应得到烷基化反应产物;木质纤维素基甲基呋喃和羰基化合物之间烷基化反应具体为:将反应底物先后加入圆底烧瓶中,控制甲基呋喃与羰基化合物的摩尔比为2:1;烷基化反应温度为50~100℃,催化剂用量与甲基呋喃质量比为0.05~0.5:1.64,反应时间为2~12小时,烷基化反应产物为碳数在13~16之间的含氧化合物;
S6:烷基化反应产物在所述镍负载的磷酸铝催化剂存在下进行加氢脱氧反应获得高产率的柴油或航空煤油, 所述加氢脱氧反应在间歇式釜式反应器中进行,釜式反应器中的反应条件为:环己烷作为溶剂,反应温度220~300℃,反应时间为6~24h,氢气压力为5至10.0MPa,加氢脱氧反应体系中反应原料的质量浓度为5~15%。
2.根据权利要求1所述的制备方法,其特征在于:木质纤维素基羰基化合物为糠醛、5-羟甲基糠醛、丙酮、2-丁酮、环戊酮、2-戊酮、环己酮中的一种或两种以上的混合物。
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