CN1212316C - Continuous production device for preparing pinanyl hydroperoxide by autoxidation of pinane - Google Patents
Continuous production device for preparing pinanyl hydroperoxide by autoxidation of pinane Download PDFInfo
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Abstract
Description
一、技术领域1. Technical field
本发明涉及蒎烷基氢过氧化物的生产装置。The present invention relates to the production device of pinanyl hydroperoxide.
二、背景技术2. Background technology
蒎烷基氢过氧化物是制造芳樟醇(香料)和维生素E等的中间体，可由蒎烷自氧化而得，其反应方程式如下：Pinanyl hydroperoxide is an intermediate in the manufacture of linalool (fragrance) and vitamin E, etc., and can be obtained by the autoxidation of pinane. The reaction equation is as follows:
蒎烷 蒎烷基氢过氧化物Pinane Pinane Hydroperoxide
目前由蒎烷自氧化制备蒎烷基氢过氧化物的典型工艺如附图1所示。A typical process for preparing pinanyl hydroperoxide by pinane autoxidation is shown in Figure 1 at present.
将一定量的蒎烷和催化剂加入间歇釜，在搅拌下连续通入氧气或空气。反应过程中定时取样分析蒎烷的自氧化程度，达到规定要求后即可出料。该工艺采用的核心设备为搅拌釜式反应器，其特点是间歇操作，工艺条件不易控制，产品质量不稳定，设备的生产能力较小。Add a certain amount of pinane and catalyst into the batch tank, and continuously feed oxygen or air under stirring. During the reaction process, samples are regularly taken to analyze the degree of autoxidation of pinane, and the material can be discharged after reaching the specified requirements. The core equipment used in this process is a stirred tank reactor, which is characterized by intermittent operation, difficult control of process conditions, unstable product quality, and small equipment production capacity.
三、发明内容3. Contents of the invention
本发明的目的是针对目前蒎烷自氧化反应间歇式生产蒎烷基氢过氧化物方法的缺点，提供一种由蒎烷自氧化制备蒎烷基氢过氧化物的连续生产方法及其装置。The object of the present invention is to provide a continuous production method and a device thereof for preparing pinanyl hydroperoxide by pinane autoxidation in order to address the disadvantages of the current batch-type production method of pinane autoxidation.
本发明的技术方案如下：Technical scheme of the present invention is as follows:
一种蒎烷自氧化制备蒎烷基氢过氧化物的连续生产方法，它是将蒎烷和催化剂组成的蒎烷溶液预热后从顶部加入到氧化塔中，同时通入经预热的氧气或空气、或者两者的混合气，使通入的气体与蒎烷溶液充分的接触，使之反应，部分反应成蒎烷基氢过氧化物，得到生成的蒎烷基氢过氧化物和蒎烷组成的生成物溶液，再取部分生成物溶液经加热或冷却后与预热后的蒎烷一同从氧化塔顶部加入到氧化塔中，使之进一步反应，如此循环，通过控制加入氧化塔的液体和通入气体的温度，以及控制加入蒎烷和循环加入的生成物溶液的流量和气体流量，调节氧化塔内的温度和压力，直到生成物溶液的蒎烷基氢过氧化物的含量达到要求后，不断放出产品蒎烷基氢过氧化物，同时不断将蒎烷和生成物溶液加入到氧化塔中，形成连续生产。A continuous production method for preparing pinane-based hydroperoxides by autoxidation of pinane, which is to preheat the pinane solution composed of pinane and a catalyst, and then add it to the oxidation tower from the top, and simultaneously feed the preheated oxygen Or air, or the mixed gas of both, make the gas that feeds in fully contact with pinane solution, make it react, partly react into pinanyl hydroperoxide, obtain the pinanyl hydroperoxide and pinane hydroperoxide that generates The product solution composed of alkane, and then part of the product solution is heated or cooled and added to the oxidation tower from the top of the oxidation tower together with the preheated pinane to make it react further, so that the cycle is controlled by controlling the amount of the oxidation tower The temperature of liquid and feed gas, and control the flow rate and the gas flow rate of the product solution that adds pinane and circulation add, regulate the temperature and pressure in the oxidation tower, until the content of the pinanel hydroperoxide of product solution reaches After the request, the product pinane alkyl hydroperoxide is continuously released, and the pinane and product solution are continuously added to the oxidation tower at the same time to form continuous production.
上述的生产方法中，氧化塔内的温度控制在70～100℃。In the above production method, the temperature in the oxidation tower is controlled at 70-100°C.
上述的生产方法中，催化剂是自由基反应引发剂，如偶氮苯甲酸。In the above-mentioned production method, the catalyst is a radical reaction initiator, such as azobenzoic acid.
上述的生产方法中催化剂的加入是一次性的，当反应已经开始后，不再需要加入催化剂，只需将蒎烷和生成物溶液不断加到氧化塔中。The adding of catalyst in the above-mentioned production method is one-off, after reaction has started, no longer needs to add catalyst, only needs to constantly add pinane and product solution in the oxidation tower.
上述的生产方法中，是取生成物溶液流出量的50～80％经加热或冷却后与预热后的蒎烷一同加入到氧化塔中。In the above-mentioned production method, 50-80% of the outflow of the product solution is heated or cooled and added to the oxidation tower together with the preheated pinane.
上述的蒎烷自氧化制备蒎烷基氢过氧化物的连续生产方法的生产装置，它包括混合罐、加料泵、液体预热器、气体预热器、氧化塔、塔顶冷凝器、塔底换热贮罐、循环泵及流量计、压力传感器、温度传感器，蒎烷和催化剂原料贮罐分别经管道和阀门连接混合罐，混合罐与加料泵连接，加料泵通过阀门和流量计与液体预热器相连，液体预热器的出口与氧化塔的顶部相通，空气或氧气输送管经流量计与气体预热器相连，气体预热器的出口与氧化塔的底部相通，氧化塔的顶部有管道与塔顶冷凝器相连，塔顶冷凝器有管道将冷凝液回流至氧化塔顶部，氧化塔的底部有产品出口阀门，并有管道与塔底换热贮罐相通，塔底换热贮罐有换热装置，可以通入加热介质或冷却介质进行加热或冷却，塔底换热贮罐底部有管道经循环泵和流量计与氧化塔顶部相连，塔底换热贮罐有产品出口，氧化塔内设置有温度传感器和压力传感器。The above-mentioned production device for the continuous production method of pinane autoxidation to prepare pinanyl hydroperoxides, which includes a mixing tank, a feed pump, a liquid preheater, a gas preheater, an oxidation tower, a tower top condenser, a tower bottom Heat exchange storage tank, circulation pump and flowmeter, pressure sensor, temperature sensor, pinane and catalyst raw material storage tank are connected to mixing tank through pipes and valves respectively, mixing tank is connected to feeding pump, and feeding pump is connected to liquid pre-processing through valve and flow meter. The outlet of the liquid preheater is connected to the top of the oxidation tower, the air or oxygen delivery pipe is connected to the gas preheater through a flow meter, the outlet of the gas preheater is connected to the bottom of the oxidation tower, and the top of the oxidation tower has The pipeline is connected to the condenser at the top of the tower. The condenser at the top of the tower has a pipeline to return the condensate to the top of the oxidation tower. There is a heat exchange device, which can be heated or cooled by heating medium or cooling medium. There is a pipeline at the bottom of the heat exchange storage tank at the bottom of the tower, which is connected to the top of the oxidation tower through a circulation pump and a flow meter. The heat exchange storage tank at the bottom of the tower has a product outlet. A temperature sensor and a pressure sensor are arranged in the tower.
上述的生产装置中，氧化塔是一个圆筒形塔体，其内部结构是板式分馏塔的结构，塔板可以是筛板、泡罩塔板、浮阀塔板、舌型塔板、斜孔筛板或导向浮阀塔板等。塔板的数量可以是4～60块，以10～40块为最佳，在氧化塔的下部有气体导入管和阀门。氧化塔的顶部设有排气口，并有管道与塔顶冷凝器相连，塔顶冷凝器有放空管。氧化塔采用分馏塔的结构是保证氧气和蒎烷充分地接触、反应。氧化塔可以在塔身的不同高度设有气体导入管和阀门，可以在塔身的不同高度控制进气量，以保证氧化塔内整体反应良好。氧化塔内的不同高度可以设有温度传感器，底部和顶部设有压力传感器。In the above-mentioned production device, the oxidation tower is a cylindrical tower body, and its internal structure is the structure of a plate fractionation tower. The trays can be sieve trays, bubble-cap trays, valve trays, tongue trays, inclined hole Sieve tray or guided valve tray, etc. The number of trays can be 4 to 60, preferably 10 to 40, and there are gas inlet pipes and valves at the lower part of the oxidation tower. The top of the oxidation tower is provided with an exhaust port, and a pipe is connected to the top condenser, and the top condenser has a vent pipe. The oxidation tower adopts the structure of a fractionating tower to ensure that oxygen and pinane fully contact and react. The oxidation tower can be equipped with gas inlet pipes and valves at different heights of the tower body, and the air intake can be controlled at different heights of the tower body to ensure a good overall reaction in the oxidation tower. Temperature sensors can be installed at different heights in the oxidation tower, and pressure sensors can be installed at the bottom and top.
上述的生产装置中，混合罐为金属或非金属材料制成的搅拌罐，其作用是设备开始运转时使蒎烷和催化剂混合均匀。In the above-mentioned production device, the mixing tank is a mixing tank made of metal or non-metallic material, and its effect is to make pinane and catalyst mix homogeneously when the equipment starts running.
上述的生产装置中，加料泵可以是离心泵、轴流泵、齿轮泵、往复泵等液体输送装置，以离心泵为最佳。加料泵的输液能力可根据生产能力的大小来确定。加料泵的出口可以有一支路和阀门与混合罐相连，以便控制蒎烷溶液进入氧化塔的流量。In the above-mentioned production device, the feeding pump can be a liquid conveying device such as a centrifugal pump, an axial flow pump, a gear pump, and a reciprocating pump, and a centrifugal pump is the best. The infusion capacity of the feeding pump can be determined according to the size of the production capacity. The outlet of the feeding pump can have a branch and a valve to be connected with the mixing tank so as to control the flow of the pinane solution into the oxidation tower.
上述的生产装置中，液体预热器可以是套管式、列管式或板式等间壁式换热器。换热器的换热面积可根据热量衡算确定。当换热面积较小时，以套管式换热器为宜，当换热面积较大时，以列管式换热器为宜。加热介质可以是热水或蒸汽，以热水为好。In the above-mentioned production device, the liquid preheater may be a casing-type, shell-and-tube or plate-type heat exchanger with a partition wall. The heat exchange area of the heat exchanger can be determined according to the heat balance calculation. When the heat exchange area is small, the casing heat exchanger is suitable, and when the heat exchange area is large, the shell and tube heat exchanger is appropriate. The heating medium can be hot water or steam, preferably hot water.
上述的生产装置中，气体预热器可以是套管式、列管式、板式或板翅式等间壁式换热器，以板翅式换热器为最佳，换热器的换热面积可根据热量衡算确定。In the above-mentioned production equipment, the gas preheater can be a casing type, a tube type, a plate type or a plate-fin type and other wall-type heat exchangers, and the plate-fin heat exchanger is the best, and the heat exchange area of the heat exchanger is It can be determined according to the heat balance calculation.
上述的生产装置中，塔顶冷凝器为金属或非金属材料制成的管式或板式间壁式换热器，用于回收氧化塔排出气体中的有机物。In the above-mentioned production device, the top condenser is a tube-type or plate-type partition wall heat exchanger made of metal or non-metal material, which is used to recover the organic matter in the exhaust gas of the oxidation tower.
上述的生产装置中，循环泵可以是离心泵、轴流泵、齿轮泵、往复泵等液体输送装置，以离心泵为最佳。循环泵的输液能力可根据液体循环量的大小来确定，循环泵的出口可以经一支管和阀门与塔底换热贮罐相连，以便控制生成物溶液循环加入到氧化塔内的流量。In the above-mentioned production device, the circulating pump can be a liquid conveying device such as a centrifugal pump, an axial flow pump, a gear pump, and a reciprocating pump, and a centrifugal pump is the best. The infusion capacity of the circulating pump can be determined according to the amount of liquid circulation. The outlet of the circulating pump can be connected to the heat exchange storage tank at the bottom of the tower through a pipe and a valve, so as to control the flow of the product solution circulating into the oxidation tower.
采用本发明的蒎烷自氧化制备蒎烷基氢过氧化物的连续生产方法和生产装置，可以方便地将蒎烷基氢过氧化物的生产方法由过去的间歇式改进为连续生产，产品质量提高，质量稳定，设备投资小，产量大，能耗低。Adopt the continuous production method and the production device of pinane autoxidation to prepare pinanyl hydroperoxide of the present invention, can conveniently improve the production method of pinanyl hydroperoxide from past intermittent type to continuous production, product quality Improvement, stable quality, small investment in equipment, large output and low energy consumption.
四、附图说明4. Description of drawings
图1为蒎烷自氧化制备蒎烷基氢过氧化物现有的典型工艺示意图，其中1为釜或反应器；2为冷凝器；A蒎烷；B催化剂；C氧气；D蒸汽；E冷却水；F冷冻盐水。Fig. 1 is the existing typical process schematic diagram of pinane autoxidation to prepare pinanyl hydroperoxide, wherein 1 is still or reactor; 2 is condenser; A pinane; B catalyst; C oxygen; D steam; E cooling water; F chilled brine.
图2为本发明的蒎烷制备蒎烷基氢过氧化物的连续生产工艺示意图，其中3为混合罐；4、5、7、10、11、16、17、18、19、21、22、24、26、27、30、31、32、33为阀门；6为加料泵；8、12、13、15为流量计；9为液体预热器；14为气体预热器；20为氧化塔；23为塔顶冷凝器；25为回流液贮罐；F冷冻盐水；G空气；H加热介质；I冷却介质；J产品；K取样口；P压力传感器；T温度传感器。Fig. 2 is the continuous production process synoptic diagram that pinane of the present invention prepares pinanyl hydroperoxide, wherein 3 is mixing tank; 4,5,7,10,11,16,17,18,19,21,22, 24, 26, 27, 30, 31, 32, 33 are valves; 6 is feeding pump; 8, 12, 13, 15 are flow meters; 9 is liquid preheater; 14 is gas preheater; 20 is oxidation tower ; 23 is the tower top condenser; 25 is the reflux liquid storage tank; F frozen brine; G air; H heating medium; I cooling medium; J product; K sampling port; P pressure sensor; T temperature sensor.
五、具体实施方式5. Specific implementation
实施例1：由蒎烷自氧化制备蒎烷基氢过氧化物。采用本发明装置，如图2所示，它主要包括混合罐3、加料泵6、液体预热器9、气体预热器14、氧化塔20、塔顶冷凝器23、回流液贮罐25、塔底换热贮罐28、循环泵29及流量计、管路和阀门，如图2所示。氧化塔20的内径为500mm，内装20块筛板。蒎烷进料量为600Kg/h，催化剂(自由基引发剂)偶氮苯甲酸一次性加入1.5Kg，600Kg蒎烷和催化剂经管道加入到混合罐3，被搅拌均匀后经阀门4、加料泵6、阀门7和流量计8进入液体预热器9预热至70℃从氧化塔20塔顶加入，液体预热器9的加热介质H为热水，同时氧气C经阀门10和流量计12进入气体预热器14，通入氧气的量为47.6m3/h(标准状况)，气体预热到70℃由氧化塔20塔底或中部进入氧化塔20，几个进气口的气体进入量根据氧化塔20内分区的温度来调节，塔内实际压力控制在1～1.2Kg/cm2，塔内温度控制在70～100℃。氧化塔20塔顶汽体经冷凝器23冷凝，冷凝液经回流液贮罐25从氧化塔20顶部返回到氧化塔20内，不冷凝气体经阀门24放空，塔顶冷凝器23用冷冻盐水作冷媒，打循环。蒎烷在氧化塔20内与氧气接触，发生自氧化反应，部分生成蒎烷基氢过氧化物，生成物溶液从氧化塔底部流出，经阀门27进入塔底换热贮罐28，生成物溶液经塔底换热贮罐28加热或冷却至70℃再经循环泵29、阀门33和流量计从氧化塔20塔顶泵入塔内，再进行反应。循环泵流量为2828Kg/h，生成物溶液可以经支管和阀门32返回塔底换热贮罐28、以便控制泵入氧化塔20内的流量。循环量控制在生成物溶液流量的50～80％，根据氧化塔底部取样分析蒎烷基氢过氧化物的浓度而定，浓度低循环量增大，浓度高循环量减小，蒎烷基氢过氧化物浓度达到39％(Wt)左右所定的产品浓度，则系统达到连续稳定运行状态，开车至连续稳定运行状态所需时间约为3.6h，此时出料流量为648Kg/h，其中蒎烷基氢过氧化物的浓度约为39.8％(Wt)。Example 1: Preparation of pinanyl hydroperoxide by autoxidation of pinane. Adopt device of the present invention, as shown in Figure 2, it mainly comprises mixing tank 3, feeding pump 6, liquid preheater 9, gas preheater 14, oxidation tower 20, tower top condenser 23, reflux liquid storage tank 25, The heat exchange storage tank 28 at the bottom of the tower, the circulating pump 29, flow meters, pipelines and valves are shown in FIG. 2 . The inner diameter of the oxidation tower 20 is 500 mm, and 20 sieve plates are installed inside. Pinane feed rate is 600Kg/h, catalyst (free radical initiator) azobenzoic acid is added 1.5Kg at one time, 600Kg pinane and catalyst are added to mixing tank 3 through pipeline, after being stirred evenly, pass through valve 4, feeding pump 6. The valve 7 and the flow meter 8 enter the liquid preheater 9 to preheat to 70°C and add it from the top of the oxidation tower 20. The heating medium H of the liquid preheater 9 is hot water, and the oxygen C passes through the valve 10 and the flow meter 12 Entering the gas preheater 14, the amount of oxygen introduced is 47.6m 3 /h (standard condition), the gas is preheated to 70°C and enters the oxidation tower 20 from the bottom or the middle of the oxidation tower 20, and the gas from several gas inlets enters the The amount is adjusted according to the temperature of the partitions in the oxidation tower 20, the actual pressure in the tower is controlled at 1-1.2Kg/cm 2 , and the temperature in the tower is controlled at 70-100°C. The gas at the top of the oxidation tower 20 is condensed by the condenser 23, and the condensed liquid is returned to the oxidation tower 20 from the top of the oxidation tower 20 through the reflux liquid storage tank 25. Refrigerant, cycle. Pinane is contacted with oxygen in the oxidation tower 20, and autoxidation reaction occurs, and partly generates pinanyl hydroperoxide, and the product solution flows out from the bottom of the oxidation tower, and enters the heat exchange storage tank 28 at the bottom of the tower through a valve 27, and the product solution It is heated or cooled to 70°C through the heat exchange storage tank 28 at the bottom of the tower, and then pumped into the tower from the top of the oxidation tower 20 through the circulating pump 29, valve 33 and flow meter, and then reacted. The flow rate of the circulation pump is 2828Kg/h, and the product solution can return to the heat exchange storage tank 28 at the bottom of the tower through the branch pipe and the valve 32, so as to control the flow rate pumped into the oxidation tower 20. The circulation volume is controlled at 50-80% of the flow rate of the product solution, and it depends on the concentration of pinanyl hydroperoxide sampled and analyzed at the bottom of the oxidation tower. The circulation volume increases when the concentration is low, and decreases when the concentration is high. When the concentration of peroxide reaches the predetermined product concentration of about 39% (Wt), the system reaches a continuous and stable operating state, and the time required for driving to the continuous and stable operating state is about 3.6 hours. At this time, the output flow rate is 648Kg/h, of which pin The concentration of alkyl hydroperoxide was about 39.8% (wt).
实施例2：由蒎烷自氧化制备蒎烷基氢过氧化物。Example 2: Preparation of pinanyl hydroperoxide by autoxidation of pinane.
采用图2所示的本发明装置，流程、步骤和条件同实施例1，但氧化塔20内的塔板改为20块浮阀塔板。进料量蒎烷为800Kg/h，催化剂一次加入量为2.0Kg，氧气通入量为32m3/h(标况)，同时通入空气，空气通入量为150m3/h(标况)，循环泵流量为2828Kg/h，系统达到连续稳定运行状态所需时间为7.8h，出料流量为864Kg/h，其中蒎烷氢过氧化物的浓度约为39.9％(Wt)。Adopt the device of the present invention shown in Fig. 2, flow process, steps and conditions are the same as embodiment 1, but the tray in the oxidation tower 20 is changed into 20 valve trays. The input amount of pinane is 800Kg/h, the amount of catalyst added at one time is 2.0Kg, the oxygen feed rate is 32m 3 /h (standard condition), and the air feed rate is 150m 3 /h (standard condition) at the same time. , the circulation pump flow rate is 2828Kg/h, the time required for the system to reach the continuous stable operation state is 7.8h, and the output flow rate is 864Kg/h, wherein the concentration of pinane hydroperoxide is about 39.9% (Wt).
实施例3：由蒎烷自氧化制备蒎烷基氢过氧化物。Example 3: Preparation of pinanyl hydroperoxide by autoxidation of pinane.
采用图2所示的本发明装置，流程，步骤和条件同实施例2，但氧化塔20内的塔板改为20块导向浮阀塔板。进料量蒎烷为800Kg/h，催化剂一次性加入2Kg，氧气通入量为32m3/h(标况)，空气通入量为150m3/h(标况)，循环泵流量为2828Kg/h，系统达到连续稳定运行状态所需时间为7.6h，出料流量为865Kg/h，其中蒎烷氢过氧化物的浓度约为40.1％(Wt)。Adopt the device of the present invention shown in Fig. 2, flow process, step and condition are the same as
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| CN104151224A (en) * | 2014-08-13 | 2014-11-19 | 广西梧松林化集团有限公司 | Method for synthesizing pinane superoxide by oxidizing pinane |
| CN111054296A (en) * | 2019-12-02 | 2020-04-24 | 河南金鹏化工有限公司 | Continuous production device and process for thiodicarb salinization reaction |
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