CN117101707A - 一种用于制备碳酸1,2-丁烯酯的催化剂及其应用 - Google Patents
一种用于制备碳酸1,2-丁烯酯的催化剂及其应用 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 37
- IJWQEEONDXVIGH-UHFFFAOYSA-N but-2-enyl hydrogen carbonate Chemical compound CC=CCOC(O)=O IJWQEEONDXVIGH-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000002808 molecular sieve Substances 0.000 claims abstract description 15
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910000449 hafnium oxide Inorganic materials 0.000 claims abstract description 10
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 8
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 3
- -1 2-butenyl ester Chemical class 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001692 polycarbonate urethane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
- B01J29/0308—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/085—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
- B01J29/087—X-type faujasite
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/085—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
- B01J29/088—Y-type faujasite
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J29/405—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7049—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
- B01J29/7053—A-type
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
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Abstract
本发明实施例公开了一种用于制备碳酸1,2‑丁烯酯的催化剂及其应用。一种用于制备碳酸1,2‑丁烯酯的催化剂,在加热条件下,将氧化铪负载在分子筛上,制得所述催化剂。本发明提供的催化剂用于合成碳酸1,2‑丁烯酯,具有催化活性高,反应选择性强的优点,能够显著提高碳酸1,2‑丁烯酯的收率,具有良好的工业应用前景。
Description
技术领域
本发明实施例涉及精细化工技术领域,具体涉及一种用于制备碳酸1,2-丁烯酯的催化剂及其应用。
背景技术
碳酸1,2-丁烯酯(1,2-butylene carbonate,BC)常温下为无色透明液体,是一种低毒物质,热分解会释放有毒的辛辣刺激性烟雾,具有独特的含氧五元杂环结构和理化性质,可广泛应用于生产聚碳酸酯和聚氨酯的原料、锂离子电池电解质溶剂、非质子极性溶剂等领域。其结构如下:
目前碳酸1,2-丁烯酯主要采用二氧化碳与环氧烷烃的环加成合成工艺,属于典型的原子经济性反应,符合绿色化学的发展方向。但现有合成方法存在催化剂的活性和反应选择性不高的问题,导致目标产物收率较低。
发明内容
为此,本发明实施例提供一种用于制备碳酸1,2-丁烯酯的催化剂及其应用。
为了实现上述目的,本发明实施例提供如下技术方案:
根据本发明实施例的第一方面,本发明提供一种用于制备碳酸1,2-丁烯酯的催化剂,在加热条件下,将氧化铪负载在分子筛上,制得所述催化剂。
进一步地,所述分子筛为沸石类分子筛或介孔分子筛。作为示例,沸石类分子筛可以为A型、Y型、X型、ZSM-5型等,介孔分子筛为SAB-15、MCM-41等。
进一步地,所述氧化铪与分子筛的质量比为1:1~1.5。
进一步地,所述加热的温度为500~600℃,时间为8~10h。
根据本发明实施例的第二方面,本发明提供如上所述的催化剂在制备碳酸1,2-丁烯酯中的应用。
根据本发明实施例的第三方面,本发明提供一种制备碳酸1,2-丁烯酯的方法,以环氧丁烷、二氧化碳为原料,在如上任一项所述的催化剂存在的条件下进行反应。
进一步地,所述反应的压力为2~5MPa,温度为195~225℃。
进一步地,所述催化剂与环氧丁烷的质量比为0.04~0.07:1;所述环氧丁烷与二氧化碳的质量比为1:0.6~0.8。
进一步地,所述方法还包括:对反应产物进行纯化,所述纯化具体包括:将反应产物在压力-0.09~-0.10MPa,温度140~170℃下进行蒸馏,所得馏分在-0.09~-0.10MPa,温度160~190℃下进行精馏,得到碳酸1,2-丁烯酯。
本发明实施例具有如下优点:
本发明提供的催化剂用于合成碳酸1,2-丁烯酯,具有催化活性高,反应选择性强的优点,能够显著提高碳酸1,2-丁烯酯的收率,具有良好的工业应用前景。
具体实施方式
以下由特定的具体实施例说明本发明的实施方式,熟悉此技术的人士可由本说明书所揭露的内容轻易地了解本发明的其他优点及功效,显然,所描述的实施例是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
本实施例提供一种催化剂,其制备方法为:
氧化铪与分子筛按照质量比1:1进行配料,然后置于离心混料机中进行充分搅拌,置于坩埚中,于500℃下加热8h,得到催化剂。
实施例2
本实施例提供一种催化剂,其制备方法为:
氧化铪与分子筛按照质量比1:1.2进行配料,然后置于离心混料机中进行充分搅拌,置于坩埚中,在550℃下加热8h,得到催化剂。
实施例3
本实施例提供一种催化剂,其制备方法为:
氧化铪与分子筛按照质量比1:1.5进行配料,然后置于离心混料机中进行充分搅拌,置于坩埚中,在600℃下加热10h,得到催化剂。
对比例1
本对比例提供一种催化剂,其与实施例1的区别在于,用等量的二氧化钛替换氧化铪。
对比例2
本对比例提供一种催化剂,其与实施例1的区别在于,用等量的氧化锌替换氧化铪。
对比例3
本对比例提供一种催化剂,其为氧化铪。
实施例4
本实施例提供一种碳酸1,2-丁烯酯的制备方法:
将15g实施例1的催化剂加入到2000mL高压釜中,通入高纯氮气置换反应釜3次,通入300g环氧丁烷至4MPa,升温至200℃后,缓慢通入195g二氧化碳,反应5h,停止加热,先将高压反应釜内的气体排出后,在-0.10Mpa、150℃下进行蒸馏,将蒸出的馏分通入到精馏塔内进行精馏,精馏塔压力控制在-0.10MPa,温度180℃,侧线采出482.4g碳酸1,2-丁烯酯,纯度为99.94%,收率为99.8%。
实施例5
本实施例提供一种碳酸1,2-丁烯酯的制备方法:
将18g实施例2的催化剂加入到2000mL高压釜中,通入高纯氮气置换反应釜3次,通入300g环氧丁烷至4MPa,升温至200℃后,缓慢通入204g二氧化碳,反应5h,停止加热,先将高压反应釜内的气体排出后,在-0.099Mpa、160℃下进行蒸馏,将蒸出的馏分通入到精馏塔内进行精馏,精馏塔压力控制在-0.099MPa,温度为190℃,侧线采出482.4g碳酸1,2-丁烯酯,纯度为99.93%,收率为99.8%。
实施例6
本实施例提供一种碳酸1,2-丁烯酯的制备方法:
将21g实施例3的催化剂加入到2000mL高压釜中,通入高纯氮气置换反应釜3次,通入300g环氧丁烷至4MPa,升温至100℃后,缓慢通入186g二氧化碳,反应5h,停止加热,先将高压反应釜内的气体排出后,在-0.10Mpa、150℃下进行蒸馏,将蒸出的馏分通入到精馏塔内进行精馏,精馏塔压力控制在-0.099MPa,温度为180℃,侧线采出481.9g碳酸1,2-丁烯酯,纯度为99.93%,收率为99.7%。
对比例4
本对比例提供一种碳酸1,2-丁烯酯的制备方法,其与实施例4的区别仅在于,使用对比例1的催化剂,结果显示:侧线采出478.1g碳酸1,2-丁烯酯,纯度为97.21%,收率为84.0%。
对比例5
本对比例提供一种碳酸1,2-丁烯酯的制备方法,其与实施例4的区别仅在于,使用对比例2的催化剂,结果显示:侧线采出421.5g碳酸1,2-丁烯酯,纯度为97.35%,收率为87.2%。
对比例6
本对比例提供一种碳酸1,2-丁烯酯的制备方法,其与实施例4的区别仅在于,使用对比例3的催化剂,结果显示:侧线采出438.2g碳酸1,2-丁烯酯,纯度为98.85%,收率为90.7%。
虽然,上文中已经用一般性说明及具体实施例对本发明作了详尽的描述,但在本发明基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
Claims (9)
1.一种用于制备碳酸1,2-丁烯酯的催化剂,其特征在于,在加热条件下,将氧化铪负载在分子筛上,制得所述催化剂。
2.根据权利要求1所述的用于制备碳酸1,2-丁烯酯的催化剂,其特征在于,所述分子筛为沸石类分子筛或介孔分子筛。
3.根据权利要求1所述的用于制备碳酸1,2-丁烯酯的催化剂,其特征在于,所述氧化铪与分子筛的质量比为1:1~1.5。
4.根据权利要求1所述的用于制备碳酸1,2-丁烯酯的催化剂,其特征在于,所述加热的温度为500~600℃,时间为8~10h。
5.权利要求1所述的催化剂在制备碳酸1,2-丁烯酯中的应用。
6.一种制备碳酸1,2-丁烯酯的方法,其特征在于,以环氧丁烷、二氧化碳为原料,在如权利要求1~4中任一项所述的催化剂存在的条件下进行反应。
7.根据权利要求6所述的方法,其特征在于,所述反应的压力为2~5MPa,温度为195~225℃。
8.根据权利要求6所述的方法,其特征在于,所述催化剂与环氧丁烷的质量比为0.04~0.07:1;所述环氧丁烷与二氧化碳的质量比为1:0.6~0.8。
9.根据权利要求6所述的方法,其特征在于,所述方法还包括:对反应产物进行纯化,所述纯化具体包括:将反应产物在压力-0.09~-0.10MPa,温度140~170℃下进行蒸馏,所得馏分在-0.09~-0.10MPa,温度160~190℃下进行精馏,得到碳酸1,2-丁烯酯。
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