WO2021017649A1 - Method for purifying 4-cyanopyridine by means of melting and crystallizing - Google Patents
Method for purifying 4-cyanopyridine by means of melting and crystallizing Download PDFInfo
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- WO2021017649A1 WO2021017649A1 PCT/CN2020/095081 CN2020095081W WO2021017649A1 WO 2021017649 A1 WO2021017649 A1 WO 2021017649A1 CN 2020095081 W CN2020095081 W CN 2020095081W WO 2021017649 A1 WO2021017649 A1 WO 2021017649A1
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- 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
- C07D213/60—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 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
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- the invention relates to the technical field of 4-cyanopyridine production, in particular to a method for purifying 4-cyanopyridine by melt crystallization.
- 4-cyanopyridine also called isonicotinonitrile, is a main by-product of 3-methylpyridine in the process of ammoxidation to produce 3-cyanopyridine.
- 4-cyanopyridine is an important intermediate of medicines, pesticides and dyes.
- the anti-tuberculosis drug isoniazid is produced using 4-cyanopyridine as a raw material. In order to obtain high-purity 4-cyanopyridine, purification is required.
- the present invention provides a method for purifying 4-cyanopyridine by melt crystallization.
- a method for purifying 4-cyanopyridine by melting crystallization includes the following steps:
- Cooling control the temperature of the reactor, and reduce the temperature of the molten 4-cyanopyridine to 71.5-73.5°C according to a certain cooling rate;
- the purity of the 4-cyanopyridine crystals is 96.5-98.5 %.
- the cooling rate is 0.5-1°C/15min.
- the crystallization time is 1 to 1.5 hours.
- step (4) the purity of the finished 4-cyanopyridine is >99.0%.
- the method for purifying 4-cyanopyridine by melting crystallization of the present invention has a simple production process and low requirements on reaction equipment.
- the peritectic phenomenon can be prevented by controlling the cooling rate during cooling and crystallization.
- Figure 1 is a gas chromatogram of the 4-cyanopyridine product obtained in Example 1;
- Figure 2 is a gas chromatogram of the 4-cyanopyridine product obtained in Comparative Example 1;
- Figure 3 is a gas chromatogram of the 4-cyanopyridine product obtained in Example 2.
- Figure 4 is a gas chromatogram of the finished 4-cyanopyridine obtained in Comparative Example 2.
- a method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
- Cooling Control the temperature of the reactor to reduce the temperature of the melted 4-cyanopyridine to 72.5°C at a cooling rate of 0.5°C/15min;
- Example 1 Using the method in Example 1 to purify 4-cyanopyridine, the primary yield of 4-cyanopyridine obtained was 37.8% and the purity of the finished product was 99.06%.
- the gas chromatogram of the finished product is shown in FIG. 1.
- a method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
- Cooling Control the temperature of the reactor, and reduce the temperature of the melted 4-cyanopyridine to 71.0°C according to the cooling rate of 0.5°C/15min;
- a method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
- Cooling control the temperature of the reactor, and reduce the temperature of the molten 4-cyanopyridine to 72.8°C according to the cooling rate of 0.8°C/15min;
- Example 2 Using the method in Example 2 to purify 4-cyanopyridine, the primary yield of 4-cyanopyridine obtained was 38.5% and the purity of the finished product was 99.42%.
- the gas chromatogram of the finished product is shown in FIG. 3.
- a method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
- Cooling down control the temperature of the reactor and reduce the solution temperature to 71.5°C at a speed of 1.5°C/15min;
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Abstract
Disclosed is a method for purifying 4-cyanopyridine by means of melting and crystallizing, comprising the following steps: (1) Melting 4-cyanopyridine: adding crystals of 4-cyanopyridine into a reactor under normal pressure and melting the crystals of 4-cyanopyridine at a reactor temperature controlled to be 80-90°C; (2) Temperature reduction: reducing the temperature of molten 4-cyanopyridine to 71.5-73.5°C at a certain temperature reduction rate by performing temperature control on the reactor; (3) Crystallization: enabling crystallization at a maintained temperature of 71.5-73.5°C; and (4) Separation and extraction: discharging the base solution from the resulting crystals, increasing the reactor temperature to 80-90°C again, and melting the resulting crystals to obtain a finished 4-cyanopyridine product. The method for purifying 4-cyanopyridine by means of melting and crystallizing according to the present invention has a simple process, and can increase the overall productivity and purity of the finished product, without any resulting by-products and contaminants, by means of controlling the rate of temperature reduction during temperature-reduction crystallization to avoid a peritectic phenomenon.
Description
本发明涉及4-氰基吡啶生产技术领域，具体涉及一种熔融结晶提纯4-氰基吡啶的方法。The invention relates to the technical field of 4-cyanopyridine production, in particular to a method for purifying 4-cyanopyridine by melt crystallization.
4-氰基吡啶也称作异烟腈，是一种3-甲基吡啶在氨氧化法生产3-氰基吡啶过程中出现的主要副产物。4-氰基吡啶是重要的医药、农药及染料的中间体，如抗结核病药物异烟肼就是以4-氰基吡啶为原料进行生产的。为了获取高纯度的4-氰基吡啶，需要进行提纯精制。4-cyanopyridine, also called isonicotinonitrile, is a main by-product of 3-methylpyridine in the process of ammoxidation to produce 3-cyanopyridine. 4-cyanopyridine is an important intermediate of medicines, pesticides and dyes. For example, the anti-tuberculosis drug isoniazid is produced using 4-cyanopyridine as a raw material. In order to obtain high-purity 4-cyanopyridine, purification is required.
目前工业分离多采用减压精馏的方法，从3-氰基吡啶和4-氰基吡啶混合体系中分离出4-氰基吡啶以提高经济效益。工业生产中4-氰基吡啶的分离效果差强人意，且操作运行成本高。基于经济成本考虑，生产企业通常将含4-氰基吡啶的3/4-氰基吡啶同系混合物当废弃物处理，或者直接作为化工废料焚烧处理，导致氰基吡啶同系混合物的回收利用率低下，造成极大的浪费和环境污染。At present, industrial separation mostly adopts the method of vacuum distillation to separate 4-cyanopyridine from the mixed system of 3-cyanopyridine and 4-cyanopyridine to improve economic benefits. The separation effect of 4-cyanopyridine in industrial production is not satisfactory, and the operation cost is high. Based on economic cost considerations, manufacturers usually treat 3/4-cyanopyridine homologous mixtures containing 4-cyanopyridine as waste, or directly incinerate them as chemical wastes, resulting in low recycling rates of cyanopyridine homologous mixtures. Cause great waste and environmental pollution.
发明内容Summary of the invention
针对上述存在的问题，本发明提供了一种熔融结晶提纯4-氰基吡啶的方法。In view of the above-mentioned problems, the present invention provides a method for purifying 4-cyanopyridine by melt crystallization.
为实现以上目的，本发明通过以下技术方案予以实现：To achieve the above objectives, the present invention is achieved through the following technical solutions:
一种熔融结晶提纯4-氰基吡啶的方法，包括以下步骤：A method for purifying 4-cyanopyridine by melting crystallization includes the following steps:
(1)4-氰基吡啶的熔融：在常压下，将4-氰基吡啶晶体加入反应器，控制反应器温度为80～90℃，将4-氰基吡啶晶体熔融；(1) The melting of 4-cyanopyridine: under normal pressure, 4-cyanopyridine crystals are added to the reactor, the temperature of the reactor is controlled to 80-90°C, and the 4-cyanopyridine crystals are melted;
(2)降温：控制反应器温度，按照一定的降温速度，将熔融后的4-氰基吡啶温度降至71.5～73.5℃；(2) Cooling: control the temperature of the reactor, and reduce the temperature of the molten 4-cyanopyridine to 71.5-73.5°C according to a certain cooling rate;
(3)结晶：将温度维持在71.5～73.5℃条件下，进行结晶；(3) Crystallization: maintain the temperature at 71.5～73.5℃ to perform crystallization;
(4)分离提取：将未形成晶体的底液放出，重新提升反应器温度至80～90℃，熔融晶体得4-氰基吡啶成品。(4) Separating and extracting: the bottom liquid without crystals is discharged, the temperature of the reactor is raised again to 80-90 DEG C, and the crystals are melted to obtain the finished product of 4-cyanopyridine.
优选地，步骤(1)中，所述4-氰基吡啶晶体的纯度为96.5～98.5％。Preferably, in step (1), the purity of the 4-cyanopyridine crystals is 96.5-98.5 %.
优选地，步骤(2)中，所述降温速率为0.5～1℃/15min。Preferably, in step (2), the cooling rate is 0.5-1°C/15min.
优选地，步骤(3)中，结晶时长为1～1.5h。Preferably, in step (3), the crystallization time is 1 to 1.5 hours.
优选地，步骤(4)中，所述4-氰基吡啶成品纯度＞99.0％。Preferably, in step (4), the purity of the finished 4-cyanopyridine is >99.0%.
本发明的有益效果是：The beneficial effects of the present invention are:
(1)本发明熔融结晶提纯4-氰基吡啶的方法，生产工艺简单，对反应的设备要求低，通过控制降温结晶时的降温速率来防止包晶现象。(1) The method for purifying 4-cyanopyridine by melting crystallization of the present invention has a simple production process and low requirements on reaction equipment. The peritectic phenomenon can be prevented by controlling the cooling rate during cooling and crystallization.
(2)本发明制备的高纯度4-氰基吡啶整体产率、纯度高，纯度＞99.0％，无任何副产物污染物，通过多级提取，原料的综合利用率超过90％。(2) The overall yield and purity of the high-purity 4-cyanopyridine prepared by the present invention are high, and the purity is greater than 99.0% without any by-product pollutants. Through multi-stage extraction, the comprehensive utilization rate of raw materials exceeds 90%.
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面 将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。In order to explain the embodiments of the present invention or the technical solutions in the prior art more clearly, the following will briefly introduce the drawings that need to be used in the description of the embodiments or the prior art. Obviously, the drawings in the following description are only These are some embodiments of the present invention. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without creative work.
图1为实施例1中所得4-氰基吡啶成品的气相色谱图；Figure 1 is a gas chromatogram of the 4-cyanopyridine product obtained in Example 1;
图2为对比例1中所得4-氰基吡啶成品的气相色谱图；Figure 2 is a gas chromatogram of the 4-cyanopyridine product obtained in Comparative Example 1;
图3为实施例2中所得4-氰基吡啶成品的气相色谱图；Figure 3 is a gas chromatogram of the 4-cyanopyridine product obtained in Example 2;
图4为对比例2中所得4-氰基吡啶成品的气相色谱图。Figure 4 is a gas chromatogram of the finished 4-cyanopyridine obtained in Comparative Example 2.
为使本发明实施例的目的、技术方案和优点更加清楚，下面将结合本发明实施例，对本发明实施例中的技术方案进行清楚、完整地描述，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作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。In order to make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be described clearly and completely in conjunction with the embodiments of the present invention. Obviously, the described embodiments are part of the present invention. Examples, not all examples. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative work shall fall within the protection scope of the present invention.
实施例1：Example 1:
一种熔融结晶提纯4-氰基吡啶的方法，具体包括以下步骤：A method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
(1)4-氰基吡啶熔融：在常压下，将纯度为96.5％的4-氰基吡啶晶体加入反应器，控制反应器温度为82℃，将晶体熔融；(1) 4-cyanopyridine melting: under normal pressure, add 4-cyanopyridine crystals with a purity of 96.5% into the reactor, control the temperature of the reactor to 82°C, and melt the crystals;
(2)降温：控制反应器温度，使之按照0.5℃/15min的降温速度，将熔融后的4-氰基吡啶温度降至72.5℃；(2) Cooling: Control the temperature of the reactor to reduce the temperature of the melted 4-cyanopyridine to 72.5°C at a cooling rate of 0.5°C/15min;
(3)结晶：将温度维持在72.5℃条件下，进行结晶，时长0.5h；(3) Crystallization: maintain the temperature at 72.5°C for crystallization for 0.5h;
(4)分离提取：将未形成晶体的底液放出，重新提升反应器温度至82℃，熔融晶体得4-氰基吡啶成品。(4) Separating and extracting: discharge the bottom liquid without crystal formation, and raise the temperature of the reactor again to 82° C. to melt the crystals to obtain 4-cyanopyridine product.
采用实施例1中的方法提纯4-氰基吡啶，得到的4-氰基吡啶成品一次收率为37.8％，成品纯度为99.06％，成品的气相色谱图如图1所示。Using the method in Example 1 to purify 4-cyanopyridine, the primary yield of 4-cyanopyridine obtained was 37.8% and the purity of the finished product was 99.06%. The gas chromatogram of the finished product is shown in FIG. 1.
对比例1：Comparative example 1:
一种熔融结晶提纯4-氰基吡啶的方法，具体包括以下步骤：A method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
(1)4-氰基吡啶熔融：在常压下，将纯度为96.8％的4-氰基吡啶晶体加入反应器，控制反应器温度为85℃，将晶体熔融；(1) 4-cyanopyridine melting: under normal pressure, add 4-cyanopyridine crystals with a purity of 96.8% into the reactor, control the temperature of the reactor to 85°C, and melt the crystals;
(2)降温：控制反应器温度，按照0.5℃/15min的降温速度，将熔融后的4-氰基吡啶温度降至71.0℃；(2) Cooling: Control the temperature of the reactor, and reduce the temperature of the melted 4-cyanopyridine to 71.0°C according to the cooling rate of 0.5°C/15min;
(3)结晶：将温度维持在71.0℃条件下，进行结晶，时长1h；(3) Crystallization: keep the temperature at 71.0℃ and carry out crystallization for 1h;
(4)分离提取：将未形成晶体的底液放出，重新提升反应器温度至85℃，熔融结晶得4-氰基吡啶成品。(4) Separating and extracting: the bottom liquid without crystal formation is discharged, the temperature of the reactor is raised again to 85°C, and the 4-cyanopyridine product is obtained by melting and crystallization.
采用对比例1中的方法提纯4-氰基吡啶，得到的4-氰基吡啶成品一次收率为40.5％，成品纯度为98.43％，成品的气相色谱图如图2所示。Using the method in Comparative Example 1 to purify 4-cyanopyridine, the primary yield of 4-cyanopyridine obtained was 40.5% and the purity of the finished product was 98.43%. The gas chromatogram of the finished product is shown in FIG. 2.
实施例2：Example 2:
一种熔融结晶提纯4-氰基吡啶的方法，具体包括以下步骤：A method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
(1)4-氰基吡啶熔融：在常压下，将纯度为96.5％的4-氰基吡啶晶体加入反应器，控制反应器温度为80℃，将晶体熔融；(1) 4-cyanopyridine melting: under normal pressure, add 4-cyanopyridine crystals with a purity of 96.5% to the reactor, control the temperature of the reactor to 80°C, and melt the crystals;
(2)降温：控制反应器温度，按照0.8℃/15min的降温速度，将熔融后的4-氰基吡啶温度降至72.8℃；(2) Cooling: control the temperature of the reactor, and reduce the temperature of the molten 4-cyanopyridine to 72.8°C according to the cooling rate of 0.8°C/15min;
(3)结晶：将温度维持在72.8℃条件下，进行结晶，时长1h；(3) Crystallization: keep the temperature at 72.8℃ for crystallization for 1h;
(4)分离提取：将未形成晶体的底液放出，重新提升反应器温度至87℃，熔融结晶得4-氰基吡啶成品。(4) Separation and extraction: the bottom liquid without crystal formation is discharged, the temperature of the reactor is raised again to 87°C, and the 4-cyanopyridine product is obtained by melting and crystallization.
采用实施例2中的方法提纯4-氰基吡啶，得到的4-氰基吡啶成品一次收率为38.5％，成品纯度为99.42％，成品的气相色谱图如图3所示。Using the method in Example 2 to purify 4-cyanopyridine, the primary yield of 4-cyanopyridine obtained was 38.5% and the purity of the finished product was 99.42%. The gas chromatogram of the finished product is shown in FIG. 3.
对比例2：Comparative example 2:
一种熔融结晶提纯4-氰基吡啶的方法，具体包括以下步骤：A method for purifying 4-cyanopyridine by melt crystallization specifically includes the following steps:
(1)4-氰基吡啶熔融：在常压下，将纯度为96.8％的4-氰基吡啶晶体加入反应器，控制反应器温度为85℃，将晶体熔融；(1) 4-cyanopyridine melting: under normal pressure, add 4-cyanopyridine crystals with a purity of 96.8% into the reactor, control the temperature of the reactor to 85°C, and melt the crystals;
(2)降温：控制反应器温度，按照1.5℃/15min的速度，将溶液温度降至71.5℃；(2) Cooling down: control the temperature of the reactor and reduce the solution temperature to 71.5°C at a speed of 1.5°C/15min;
(3)结晶将温度维持在71.5℃条件下，进行结晶，时长1h；(3) Crystallization: Maintain the temperature at 71.5°C for crystallization for 1 hour;
(4)分离提取：将未形成晶体的底液放出，重新提升反应器温度至85℃，熔融结晶得4-氰基吡啶成品。(4) Separating and extracting: the bottom liquid without crystal formation is discharged, the temperature of the reactor is raised again to 85°C, and the 4-cyanopyridine product is obtained by melting and crystallization.
采用对比例2中的方法提纯4-氰基吡啶，得到的4-氰基吡啶成品一次收率为35.1％，成品纯度为97.66％，成品的气相色谱图如图4所示。Using the method in Comparative Example 2 to purify 4-cyanopyridine, the primary yield of 4-cyanopyridine obtained was 35.1%, and the purity of the finished product was 97.66%. The gas chromatogram of the finished product is shown in FIG. 4.
以上实施例仅用以说明本发明的技术方案，而非对其限制；尽管参照前述实施例对本发明进行了详细的说明，本领域的普通技术人员应当理解：其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换；而这些修改或者替换，并不使相应技术方案的本质脱离本发明各实施例技术方案的精神和范围。The above embodiments are only used to illustrate the technical solutions of the present invention, but not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that: The recorded technical solutions are modified, or some of the technical features are equivalently replaced; these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (5)
- 一种熔融结晶提纯4-氰基吡啶的方法，其特征在于，包括以下步骤：A method for purifying 4-cyanopyridine by melt crystallization, characterized in that it comprises the following steps:(1)4-氰基吡啶的熔融：在常压下，将4-氰基吡啶晶体加入反应器，控制反应器温度为80～90℃，将4-氰基吡啶晶体熔融；(1) The melting of 4-cyanopyridine: under normal pressure, 4-cyanopyridine crystals are added to the reactor, the temperature of the reactor is controlled to 80-90°C, and the 4-cyanopyridine crystals are melted;(2)降温：控制反应器温度，按照一定的降温速度，将熔融后的4-氰基吡啶温度降至71.5～73.5℃；(2) Cooling: control the temperature of the reactor, and reduce the temperature of the molten 4-cyanopyridine to 71.5～73.5℃ according to a certain cooling rate;(3)结晶：将温度维持在71.5～73.5℃条件下，进行结晶；(3) Crystallization: maintain the temperature at 71.5～73.5℃ for crystallization;(4)分离提取：将未形成晶体的底液放出，重新提升反应器温度至80～90℃，熔融晶体得4-氰基吡啶成品。(4) Separating and extracting: the bottom liquid without crystals is discharged, the temperature of the reactor is raised again to 80-90 DEG C, and the crystals are melted to obtain the finished product of 4-cyanopyridine.
- 根据权利要求1所述的熔融结晶提纯4-氰基吡啶的方法，其特征在于，步骤(1)中，所述4-氰基吡啶晶体的纯度为96.5～98.5％。The method for purifying 4-cyanopyridine by melting crystallization according to claim 1, characterized in that, in step (1), the purity of the 4-cyanopyridine crystals is 96.5% to 98.5%.
- 根据权利要求1所述的熔融结晶提纯4-氰基吡啶的方法，其特征在于，步骤(2)中，所述降温速率为0.5～1℃/15min。The method for purifying 4-cyanopyridine by melt crystallization according to claim 1, characterized in that, in step (2), the cooling rate is 0.5-1°C/15min.
- 根据权利要求1所述的熔融结晶提纯4-氰基吡啶的方法，其特征在于，步骤(3)中，结晶时长为1～1.5h。The method for purifying 4-cyanopyridine by melting crystallization according to claim 1, wherein in step (3), the crystallization time is 1 to 1.5 hours.
- 根据权利要求1所述的熔融结晶提纯4-氰基吡啶的方法，其特征在于，步骤(4)中，所述4-氰基吡啶成品纯度＞99.0％。The method for purifying 4-cyanopyridine by melting crystallization according to claim 1, characterized in that, in step (4), the purity of the finished product of 4-cyanopyridine is >99.0%.
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| CN110655489A (en) * | 2019-11-11 | 2020-01-07 | 安徽瑞邦生物科技有限公司 | Method for purifying 4-cyanopyridine by volatilization and recrystallization |
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| CN106478498A (en) * | 2016-09-23 | 2017-03-08 | 哈尔滨理工大学 | Using chemical recrystallization and physical separation combine purification 4 cyanopyridines method |
| CN110272382A (en) * | 2019-08-01 | 2019-09-24 | 安徽瑞邦生物科技有限公司 | A kind of method of fusion-crystallization purification 4- cyanopyridine |
| CN110790702A (en) * | 2019-11-11 | 2020-02-14 | 安徽瑞邦生物科技有限公司 | Method for purifying 4-cyanopyridine by combining chemical recrystallization and physical separation |
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