CN106977449B - 一种3,5-二甲基-2-乙基吡啶的催化合成方法 - Google Patents
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- QLUUXTUCKOZMEL-UHFFFAOYSA-N 2-ethyl-3,5-dimethylpyridine Chemical compound CCC1=NC=C(C)C=C1C QLUUXTUCKOZMEL-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000007036 catalytic synthesis reaction Methods 0.000 title claims abstract description 12
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims abstract description 50
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 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 38
- 239000002808 molecular sieve Substances 0.000 claims abstract description 37
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 21
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- RDOWRVTXAPIIKV-UHFFFAOYSA-N 2-ethyl-3,4-dimethylpyridine Chemical compound CCC1=NC=CC(C)=C1C RDOWRVTXAPIIKV-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229910017119 AlPO Inorganic materials 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000007790 solid phase Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
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- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N 2,3,5-trimethylpyridine Chemical compound CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
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- 239000002245 particle Substances 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- -1 2,3,5-trimethylpyridine 3,5-dimethyl-2-ethylpyridine Chemical compound 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 description 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
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- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
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- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
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- 229960000381 omeprazole Drugs 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
本发明公开了一种3,5‑二甲基‑2‑乙基吡啶的催化合成方法，该方法为：在固定床反应器中，使用AEL拓扑型分子筛作为催化剂，以丙醛和氨气为原料，在气固相条件下催化合成3,5‑二甲基‑2‑乙基吡啶。AEL型分子筛包括AlPO4‑11和引入金属杂原子的ZnAPO‑11、MgAPO‑11、CoAPO‑11分子筛，反应温度为250～400℃，压力为0.1～1MPa，丙醛和氨气的进料摩尔比为1:0.5～4，体积空速为400～1400h‑1。本合成工艺反应原料廉价易得，反应条件温和，操作简单，3,5‑二甲基‑2‑乙基吡啶的收率和选择性高。
Description
技术领域
本发明涉及一种3,5-二甲基-2-乙基吡啶的催化合成方法，属于吡啶类化合物的合成技术。
背景技术
3,5-二甲基-2-乙基吡啶(EDMP)，黄色透明液体，是合成2,3,5-三甲基吡啶等烷基吡啶的重要中间体，2,3,5-三甲基吡啶是重要的溶剂，也是合成奥美拉唑的中间体，国内并未有厂家生产3,5-二甲基-2-乙基吡啶。
国外已有一些合成3,5-二甲基-2-乙基吡啶的制备方法，如：
(1)以烯丙胺为原料，烯丙胺发生自身脱氨、环化、脱氢等过程，生成3,5-二甲基-2-乙基吡啶，该方法的缺点是同时产生4-乙基-3,5-二甲基吡啶及另一种副产物，反应的产率较低为36％，而且反应原料烯丙胺是剧毒化学品，是管制类商品，价格昂贵且难以得到。
(2)乙烯与氢气、一氧化碳和氨气在压力为4～13MPa，温度为150～300℃时，反应生成3,5-二甲基-2-乙基吡啶，催化剂为负载1％铑(Rh)的γ-Al2O3催化剂，反应的时间为4～5h，气体转化率为70～80％，主产品的含量可达到80％，该方法的缺点是反应压力较高，且催化剂比较昂贵。
发明内容
技术问题：本发明的目的是提供一种新的3,5-二甲基-2-乙基吡啶合成方法，以解决现有生产方法中存在的产品收率低、原料昂贵、反应条件苛刻等问题，从而实现提高反应选择性和产物收率，减少废物排放，更易于工业化生产的目的。本发明的目的是这样实现的：以丙醛和氨气为原料，将丙醛汽化后与已预热的氨气混合，在已装入催化剂的固定床反应器中发生气固相催化反应，丙醛和氨气发生缩合反应缩合制备3,5-二甲基-2-乙基吡啶。
技术方案：本发明是一种3,5-二甲基-2-乙基吡啶的催化合成方法，该催化合成方法在固定床反应器中，以丙醛和氨气为原料催化合成3,5-二甲基-2-乙基吡啶，丙醛和氨气的进料摩尔比为1:0.5～4，反应条件为：反应温度250～400℃，反应压力0.1～1MPa，体积空速400～1400h-1，连续反应醛氨缩合制备3,5-二甲基-2-乙基吡啶。
所述催化合成方法的具体制备步骤为：
1)丙醛经汽化后与氨气混合进入反应器，丙醛和氨气的进料摩尔比为1:0.5～4；
2)装入催化剂，在N2气氛中、温度250～300℃进行活化，在250～400℃、0.1～1MPa下进行反应；
3)反应完全后得到的产物经过分离、减压蒸馏得到3,5-二甲基-2-乙基吡啶产品。
所述的催化剂选择AEL型分子筛及引入金属杂原子的分子筛作为催化剂。
所述的分子筛，引入的金属元素为Zn，Mg或Co，分别记为ZnAPO-11、MgAPO-11、CoAPO-11分子筛，Zn，Mg或Co的添加量与分子筛中Al含量的摩尔比例在0.01～0.2之间。
所述的CoAPO-11分子筛是Co添加量与分子筛中Al的含量的摩尔比例在0.03～0.1之间的CoAPO-11分子筛。
所述的反应温度优选350～400℃，反应压力优选0.1～0.3MPa。
有益效果：
(1)反应原料为丙醛和氨气，比较廉价；反应温度和压力不高，条件温和。
(2)将金属原子引入分子筛，增强分子筛酸性，提高分子筛活性，继而提高3,5-二甲基-2-乙基吡啶的收率。
(3)本发明所提供的合成工艺十分简单，便于操作，适用于大规模生产。
具体实施方式
发明所涉及的3,5-二甲基-2-乙基吡啶生产方法中所选用的催化剂为自行制备的AEL拓扑型磷酸铝分子筛(AlPO4-11)及引入金属原子的分子筛，引入分子筛选择的金属元素为Zn，Mg或Co(ZnAPO-11、MgAPO-11、CoAPO-11)，它们的添加量与分子筛中Al含量的摩尔比在0.01～0.2之间。催化剂选用粒径40～120目，表面积在190～210m2/g之间，具有良好的水热稳定性和热稳定性，比较适合该方法固定床反应中的条件。
本发明涉及的3,5-二甲基-2-乙基吡啶合成工艺的步骤具体如下：
(1)丙醛经汽化后与氨气混合进入反应器，丙醛和氨气的进料摩尔比为1:0.5～4；
(2)装入催化剂，在N2气氛中、温度250～300℃进行活化，在250～400℃、0.1～1MPa，体积空速400～1400h-1下进行反应；
(3)反应完全后得到的产物经过分离、减压蒸馏得到3,5-二甲基-2-乙基吡啶产品。
下面结合实施例对本发明做更进一步地解释。发明人经过多次试验，有较多成功实施例，认为实施方式可为如下：反应管为内径12mm、长度50cm的不锈钢管制作，其中催化剂的装填量为4～7g。丙醛用高效液相色谱泵打入，采用精密控温设备进行温度控制，控温精度为±0.2℃，质量流量计采用电磁阀控制， 可以较好地控制气体流量。下述实施例不以任何方式限制本发明，凡采用等同替换或等效变换的方式所获得的技术方案，均处于本发明的保护范围之中。
实施例1
(1)在固定床反应管中加入5g AlPO4-11分子筛，分子筛粒度为40～120目，升高温度，活化催化剂；
(2)通入丙醛和氨气进行反应，丙醛和氨进料的摩尔比为1:4，体积空速800h-1，反应温度为250℃，反应压力为0.1MPa；
(3)反应完全后收集产品经分馏得到粗3,5-二甲基-2-乙基吡啶产品，进行三次减压精馏得到黄色油状液体，经色谱、质谱、红外和核磁共振鉴定所得产品为3,5-二甲基-2-乙基吡啶；
(4)根据气相色谱分析结果，计算3,5-二甲基-2-乙基吡啶收率和选择性。
本实施例得到的3,5-二甲基-2-乙基吡啶平均收率为28.8％，选择性为50.6％。
实施例2
实施例2中3,5-二甲基-2-乙基吡啶的合成方法与实施例1基本一致，催化剂仍然是AlPO4-11分子筛，体积空速为800h-1，区别是反应温度提升为350℃，丙醛和氨进料的摩尔比为1:2。本实施例得到反应稳定时，3,5-二甲基-2-乙基吡啶平均收率为53.7％，平均选择性为70.8％。
实施例3
实施例3中3,5-二甲基-2-乙基吡啶的合成方法与实施例1基本一致，催化剂为AlPO4-11分子筛，反应温度为350℃，反应压力为0.2MPa，体积空速为1000h-1，依次考察不同醛氨进料摩尔比(2:1、1:1、1:2、1:3、1:4)条件下3,5-二甲基-2-乙基吡啶的收率和选择性，结果见表1。
表1
由表可以看出当醛氨比为2:1时，氨的加入量较小，3,5-二甲基-2-乙基吡啶的收率和选择性；逐渐增加进料中氨的量时，为了保持空速不变，需要降低进料中丙醛的量，丙醛此时能够和氨充分反应，提高3,5-二甲基-2-乙基吡啶的收率和选择性；当进料醛氨摩尔比为1:2，3,5-二甲基-2-乙基吡啶的收率和选择基本达到最大，平均收率为53.5％，选择性71.8％；醛氨比为1:4时3,5-二甲基-2-乙基吡啶收率和选择性略微有所降低。
实施例4
实施例4中3,5-二甲基-2-乙基吡啶的合成方法与实施例1基本一致，反应压力为0.1MPa，体积空速为1000h-1，区别是催化剂为ZnAPO-11分子筛，Zn引入量与分子筛中Al含量摩尔比为0.03，丙醛和氨气进料摩尔比为1:2，反应温度为350℃，结果见表2。
实施例5
实施例5中3,5-二甲基-2-乙基吡啶的合成方法与实施例1基本一致，反应压力为0.1MPa，体积空速为1000h-1，区别是催化剂为MgAPO-11分子筛，Mg引入量与分子筛中Al含量的摩尔比为0.06，丙醛和氨气进料摩尔比为1:2，反应温度为350℃，结果见表2。
实施例6
实施例6中3,5-二甲基-2-乙基吡啶的合成方法与实施例1基本一致，反应压力为0.1MPa，体积空速为1000h-1，区别是催化剂为CoAPO-11分子筛，Co引入量与分子筛中Al含量的摩尔比为0.04，丙醛和氨气进料摩尔比为1:2，反应温度为350℃，结果见表2。
表2
实施例2、4、5、6对比了不同分子筛作为催化剂时3,5-二甲基-2-乙基吡啶的收率和选择性，由表2相对于AlPO4-11，引入杂原子之后，分子筛的催化活性均有所提高，表现为3,5-二甲基-2-乙基吡啶的选择性收率都有所增加，其中CoAPO-11为催化剂时3,5-二甲基-2-乙基吡啶的收率最高，平均收率达到80.03％，其次分别是ZnAPO-11、MgAPO-11。
通过实施例结果分析，反应过程中采用合适的反应条件及选择金属改性的分子筛作为催化剂可以提高催化剂活性，增加3,5-二甲基-2-乙基吡啶的收率和选择性。
本发明的一种3,5-二甲基-2-乙基吡啶生产方法已经通过具体的实例进行了描述，本领域技术人员可借鉴本发明内容，适当改变原料、工艺条件等环节来实现相应的其它目的，其相关改变都没有脱离本发明的内容，所有类似的替换和改动对于本领域技术人员来说是显而易见的，都被视为包括在本发明的范围之内。
Claims (3)
1.一种3,5-二甲基-2-乙基吡啶的催化合成方法，其特征在于该催化合成方法在固定床反应器中，以丙醛和氨气为原料催化合成3,5-二甲基-2-乙基吡啶，丙醛和氨气的进料摩尔比为1:1～4，反应条件为：反应温度250～400℃，反应压力0.1～1MPa，体积空速400～1400h-1，连续反应醛氨缩合制备3,5-二甲基-2-乙基吡啶；
所述催化合成方法的具体制备步骤为：
1)丙醛经汽化后与氨气混合进入反应器，丙醛和氨气的进料摩尔比为1:1～4；
2)装入催化剂，在N2气氛中、温度250～300℃进行活化，在250～400℃、0.1～1MPa下进行反应；
3)反应完全后得到的产物经过分离、减压蒸馏得到3,5-二甲基-2-乙基吡啶产品；
所述的催化剂选自引入金属杂原子的AEL型分子筛作为催化剂；
所述的分子筛，引入的金属元素为Zn，Mg或Co，分别记为ZnAPO-11、MgAPO-11、CoAPO-11分子筛，Zn，Mg或Co的添加量与分子筛中Al含量的摩尔比例在0.01～0.2之间。
2.根据权利要求1所述的3,5-二甲基-2-乙基吡啶的催化合成方法，其特征在于所述的CoAPO-11分子筛是Co添加量与分子筛中Al的含量的摩尔比例在0.03～0.1之间的CoAPO-11分子筛。
3.根据权利要求1所述的3,5-二甲基-2-乙基吡啶的催化合成方法，其特征在于所述的反应温度优选350～400℃，反应压力优选0.1～0.3MPa。
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