CN107793316A - A kind of method of microreactor synthesis methyl nitrite - Google Patents

A kind of method of microreactor synthesis methyl nitrite Download PDF

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CN107793316A
CN107793316A CN201711271225.0A CN201711271225A CN107793316A CN 107793316 A CN107793316 A CN 107793316A CN 201711271225 A CN201711271225 A CN 201711271225A CN 107793316 A CN107793316 A CN 107793316A
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methyl nitrite
microreactor
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CN107793316B (en
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尧超群
陈光文
阎立军
焦凤军
刘宏博
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Advanced Energy Technological Innovation Inc Karamay
Dalian Institute of Chemical Physics of CAS
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Dalian Institute of Chemical Physics of CAS
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/04Preparation of esters of nitrous acid
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    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0093Microreactors, e.g. miniaturised or microfabricated reactors

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Abstract

本发明公开了一种微反应器合成亚硝酸甲酯的方法,其主要特点是:(a)NO和O2首先在列管式反应器中预反应,生成含氮氧化合物的混合气体(b)混合气体和甲醇在微通道式反应器(单通道或多通道)内进行硝化反应,生成亚硝酸甲酯。微反应通道的水力直径位于100~3000微米范围,微反应器内气相空速为2000~50000h‑1,气相中N2含量40~70%,NO和O2体积比4~7,甲醇和进料NO摩尔比1~2,反应完产物亚硝酸甲酯基于O2的收率大于70%。该反应工艺物料停留时间短,副反应得到有效抑制,减少了HNO3等的生成,设备不易腐蚀。同时,利用微通道反应器高效传质传热的特点,工艺具有较好的操作性和安全性。The invention discloses a method for synthesizing methyl nitrite with a microreactor, the main features of which are: (a) NO and O2 are first pre-reacted in a tubular reactor to generate a mixed gas containing nitrogen oxides (b ) mixed gas and methanol in a micro-channel reactor (single channel or multi-channel) for nitration reaction to generate methyl nitrite. The hydraulic diameter of the micro-reaction channel is in the range of 100-3000 microns, the gas phase space velocity in the micro-reactor is 2000-50000h -1 , the N2 content in the gas phase is 40-70%, the volume ratio of NO and O2 is 4-7, methanol and feed The molar ratio of NO is 1-2, and the yield of methyl nitrite based on O2 after the reaction is greater than 70%. The reaction process has a short material residence time, effectively suppresses side reactions, reduces the generation of HNO3 , etc., and the equipment is not easy to corrode. At the same time, using the characteristics of high-efficiency mass and heat transfer in microchannel reactors, the process has better operability and safety.

Description

一种微反应器合成亚硝酸甲酯的方法A kind of method that microreactor synthesizes methyl nitrite

技术领域technical field

本发明涉及一种亚硝酸甲酯的合成方法,具体为利用微型反应器连续合成亚硝酸甲酯。The invention relates to a method for synthesizing methyl nitrite, in particular to using a micro-reactor to continuously synthesize methyl nitrite.

背景技术Background technique

乙二醇作为一种重要的有机化工原料,主要用于生产聚酯纤维、塑料和橡胶等,也广泛应用于溶剂、润滑剂、增塑剂和防冻剂等方面。我国乙二醇供应存在较大缺口,进口依存度高达70%,且主要来源于中东和北美。鉴于聚酯工业的强劲需求,预计未来我国乙二醇的需求量将进一步增加。As an important organic chemical raw material, ethylene glycol is mainly used in the production of polyester fibers, plastics and rubber, and is also widely used in solvents, lubricants, plasticizers and antifreeze. There is a large gap in the supply of ethylene glycol in my country, and the dependence on imports is as high as 70%, mainly from the Middle East and North America. In view of the strong demand of the polyester industry, it is expected that the demand for ethylene glycol in my country will further increase in the future.

乙二醇工艺路线主要分为石油路线和煤基路线。近年来,煤基路线发展迅速,且经济性也逐渐提高。例如,新疆生产的煤制乙二醇的生产成本在2500-3000元/吨,无论从绝对利润率还是与其他供给国家的相对成本比较,都有一定的竞争力。Ethylene glycol process routes are mainly divided into petroleum routes and coal-based routes. In recent years, the coal-based route has developed rapidly, and its economy has gradually improved. For example, the production cost of coal-to-ethylene glycol produced in Xinjiang is 2,500-3,000 yuan/ton, which is quite competitive in terms of absolute profit margin and relative cost compared with other supplying countries.

煤基乙二醇路线主要通过CO气相催化偶联法制草酸甲酯然后加氢合成乙二醇。其中偶联反应生成的NO与产品分离后,与氧气和甲醇反应再次生成亚硝酸甲酯并返回偶联过程循环使用,即亚硝酸甲酯再生反应:The coal-based ethylene glycol route mainly produces methyl oxalate through CO gas-phase catalytic coupling method and then hydrogenates it to ethylene glycol. After the NO generated by the coupling reaction is separated from the product, it reacts with oxygen and methanol to generate methyl nitrite again and returns to the coupling process for recycling, that is, the methyl nitrite regeneration reaction:

4NO+O2+4CH3OH→4CH3ONO+2H2O (1)4NO+O 2 +4CH 3 OH→4CH 3 ONO+2H 2 O (1)

此反应为气液两相硝化反应,反应速度快和放热量大。目前工业上多使用填料鼓泡床进行反应,气液接触面积低(200~2000m-1),传质能力较低。因而反应器设备体积往往较大以增加反应时间,反应器的运行效率较低。另外,塔式反应器中物料停留时间长(Li等Ind.Eng.Chem.Res,2013,52:2814-2823),易生成较大量的硝酸(2%~4%甚至更高,CN201310416056),对设备产生严重的腐蚀。This reaction is a gas-liquid two-phase nitration reaction with fast reaction speed and large heat release. At present, packing bubbling bed is mostly used in industry for reaction, the gas-liquid contact area is low (200-2000m -1 ), and the mass transfer capacity is low. Therefore, the volume of the reactor equipment is often large to increase the reaction time, and the operating efficiency of the reactor is low. In addition, the material residence time in the tower reactor is long (Li et al. Ind.Eng.Chem.Res, 2013, 52:2814-2823), and it is easy to generate a large amount of nitric acid (2%~4% or even higher, CN201310416056), Severe corrosion of equipment.

发明内容Contents of the invention

本发明目的在于提供一种微反应器合成亚硝酸甲酯的方法。The object of the invention is to provide a method for synthesizing methyl nitrite in a microreactor.

为实现上述目的,本发明采用的技术方案如下:To achieve the above object, the technical scheme adopted in the present invention is as follows:

一种微反应器合成亚硝酸甲酯的方法包含预反应和微反应两个步骤,预反应步骤生成含氮氧化合物的混合气体,微反应步骤合成亚硝酸甲酯。A method for synthesizing methyl nitrite with a microreactor comprises two steps of pre-reaction and micro-reaction, the pre-reaction step generates a mixed gas containing nitrogen oxide compounds, and the micro-reaction step synthesizes methyl nitrite.

所述预反应步骤采用管式反应器,使包含NO、O2、N2的混合气体在该管式反应器中反应生成含N2、N2O3和NO2的混合气,反应在常温下进行,气体停留时间在1~15min;或,反应在80~120℃反应,停留时间1~2秒;管式反应器入口气体中NO与O2摩尔比为4~7,优选4~5,N2体积含量为40~70%,优选50-55%。The pre-reaction step uses a tubular reactor to react the mixed gas containing NO, O 2 and N 2 in the tubular reactor to generate a mixed gas containing N 2 , N 2 O 3 and NO 2 , and the reaction is carried out at room temperature The gas residence time is 1 to 15 minutes; or, the reaction is carried out at 80 to 120 ° C, and the residence time is 1 to 2 seconds; the molar ratio of NO to O2 in the inlet gas of the tubular reactor is 4 to 7, preferably 4 to 5 , N 2 volume content is 40-70%, preferably 50-55%.

所述微反应在单通道微反应器或多通道微反应器中进行,使甲醇与含氮氧化合物的混合气体反应生成亚硝酸甲酯;微反应器内甲醇与原料NO摩尔比为1~2,优选为1.2~1.5;压力范围为0.1~0.5MPa,优选为0.1~0.3MPa。The micro-reaction is carried out in a single-channel micro-reactor or a multi-channel micro-reactor, so that methanol and a mixed gas containing nitrogen oxides react to generate methyl nitrite; the molar ratio of methanol to raw material NO in the micro-reactor is 1-2 , preferably 1.2 to 1.5; the pressure range is 0.1 to 0.5 MPa, preferably 0.1 to 0.3 MPa.

所述微反应器,微反应通道中的单通道和/或多通道的水力直径为100~3000微米,长度10~100厘米,微反应器空速为2000~50000h-1,反应温度为0~50℃。In the micro-reactor, the hydraulic diameter of the single channel and/or multiple channels in the micro-reaction channel is 100-3000 microns, the length is 10-100 cm, the space velocity of the micro-reactor is 2000-50000h -1 , and the reaction temperature is 0-3000 50°C.

微型反应器出口物料经气液分离器分离气相和液相。出口处部分液相物料与新鲜甲醇混合后返回微型反应器反应。气液分离器类型可选带微细格栅(尺寸20~30微米)的微型分离器、重力分离器和旋风分离器,优选旋风分离器。The material at the outlet of the microreactor is separated from the gas phase and the liquid phase by a gas-liquid separator. Part of the liquid phase material at the outlet is mixed with fresh methanol and returned to the microreactor for reaction. The type of gas-liquid separator can be a micro-separator with a fine grid (20-30 microns in size), a gravity separator and a cyclone separator, preferably a cyclone separator.

与现有技术相比,本发明的优点在于:Compared with the prior art, the present invention has the advantages of:

1)气液混合效率高,反应高效,甲醇使用量较现有技术低30%以上。短停留时间使副产物硝酸的生成量大幅降低。1) The gas-liquid mixing efficiency is high, the reaction is efficient, and the amount of methanol used is more than 30% lower than that of the prior art. The short residence time greatly reduces the formation of by-product nitric acid.

2)传热能力强,反应过程在常温下进行,能耗低。2) The heat transfer ability is strong, the reaction process is carried out at normal temperature, and the energy consumption is low.

3)反应安全,N2含量低(40%~70%),减小反应器体积和动力损耗。3) The reaction is safe, the N2 content is low (40%-70%), and the reactor volume and power loss are reduced.

4)并行放大和尺度放大并用,产能放大简单。4) Parallel enlargement and scale enlargement are used together, and the capacity enlargement is simple.

附图说明Description of drawings

图1为亚硝酸甲酯再生反应工艺原理示意图。其中,1-含NO和N2的混合气,2-O2,3-N2,4-含N2O3混合气,5-新鲜甲醇,6-回收甲醇,7-甲醇物料,8-反应后气液混合物,9-产品气,①-管式预反应器,②-微反应器,③-气液分离器。Figure 1 is a schematic diagram of the methyl nitrite regeneration reaction process principle. Among them, 1-mixed gas containing NO and N 2 , 2-O 2 , 3-N 2 , 4-mixed gas containing N 2 O 3 , 5-fresh methanol, 6-recovered methanol, 7-methanol material, 8- Gas-liquid mixture after reaction, 9-product gas, ①-tubular pre-reactor, ②-micro-reactor, ③-gas-liquid separator.

具体实施方式Detailed ways

经偶联反应并分离后的主要含NO和N2的混合气1与O2 2经管式反应器①预反应生成N2O3的混合气4,另有N2 3用于调节混合气组成和吹扫装置,管式反应器①出口气体进入微型反应器②内与甲醇进行酯化反应,生成亚硝酸甲酯,入口气体中NO/O2摩尔比范围含端值为4~7,优选为4~5;N2体积含量含端值为40~70%,优选为50-55%,反应后气液混合物8经③-气液分离器,分离回收得到的甲醇与新鲜甲醇5混合后返回微型反应器②反应。After the coupling reaction and separation, the mixed gas 1 mainly containing NO and N 2 and O 2 2 are pre-reacted in the tubular reactor ① to form a mixed gas 4 of N 2 O 3 , and N 2 3 is used to adjust the composition of the mixed gas And purging device, the outlet gas of the tubular reactor ① enters the micro-reactor ② for esterification reaction with methanol to generate methyl nitrite, and the NO/ O2 molar ratio range in the inlet gas contains an end value of 4 to 7, preferably 4 to 5; the N2 volume content contains an end value of 40 to 70%, preferably 50 to 55%. After the reaction, the gas-liquid mixture 8 passes through ③-gas-liquid separator, and the methanol obtained after separation and recovery is mixed with fresh methanol 5 Return to microreactor ② for reaction.

实施例1Example 1

在管式反应器①入口NO/O2摩尔比为4,气相N2体积含量40%,预反应温度常温,反应停留时间10min。单通道微反应器②水力直径1000微米,气相空速为13000h-1,甲醇/NO摩尔比为2,微反应器反应温度50℃,系统压力常压条件下,气相出口亚硝酸甲酯体积含量为43%,基于O2的产物收率为84.6%。In the tubular reactor ① the inlet NO/O 2 molar ratio is 4, the gas phase N 2 volume content is 40%, the pre-reaction temperature is normal temperature, and the reaction residence time is 10 min. Single-channel microreactor ②The hydraulic diameter is 1000 microns, the gas phase space velocity is 13000h -1 , the methanol/NO molar ratio is 2, the reaction temperature of the microreactor is 50°C, and the system pressure is normal pressure, the volume content of methyl nitrite at the gas phase outlet was 43%, and the product yield based on O2 was 84.6%.

实施例2Example 2

在管式反应器①入口NO/O2摩尔比为5,气相N2体积含量60%,预反应温度常温,反应停留时间8min。单通道微反应器②水力直径300微米,气相空速为50000h-1,甲醇/NO摩尔比为2,微反应器反应温度30℃,系统压力为0.2MPa条件下,气相出口亚硝酸甲酯体积含量为27.3%,基于O2的产物收率为85.3%.In the tubular reactor ①, the inlet NO/O 2 molar ratio is 5, the gas phase N 2 volume content is 60%, the pre-reaction temperature is normal temperature, and the reaction residence time is 8 min. The volume of methyl nitrite at the outlet of the gas phase is under the conditions of a single-channel microreactor ② with a hydraulic diameter of 300 microns, a gas phase space velocity of 50000 h -1 , a methanol/NO molar ratio of 2, a microreactor reaction temperature of 30 °C, and a system pressure of 0.2 MPa. The content was 27.3%, and the product yield based on O2 was 85.3%.

实施例3Example 3

在管式反应器①入口NO/O2摩尔比为4,气相N2体积含量60%,预反应温100℃,反应停留时间1.2s。并行多通道(并行数目30)微反应器②水力直径1000微米,气相空速为50000h-1,气相N2体积含量60%,NO/O2=4,甲醇/NO摩尔比为2,微反应器反应温度30℃,系统压力为常压条件下,气相出口亚硝酸甲酯体积含量为31.6%,基于氧气的产物收率为80.2%。In the tubular reactor ①, the inlet NO/O 2 molar ratio is 4, the gas phase N 2 volume content is 60%, the pre-reaction temperature is 100°C, and the reaction residence time is 1.2s. Parallel multi-channel (parallel number 30) microreactor ② hydraulic diameter 1000 microns, gas phase space velocity 50000h -1 , gas phase N 2 volume content 60%, NO/O 2 = 4, methanol/NO molar ratio 2, micro reaction Under the conditions of the reactor reaction temperature of 30° C. and the system pressure of normal pressure, the volume content of methyl nitrite at the outlet of the gas phase is 31.6%, and the product yield based on oxygen is 80.2%.

实施例4Example 4

在管式反应器①入口NO/O2摩尔比为4,气相N2体积含量60%,预反应温100℃,反应停留时间1.2s。并行多通道(并行数目30)微反应器②水力直径1000微米,气相空速为50000h-1,气相N2体积含量60%,NO/O2=4,甲醇/NO摩尔比为1.5,微反应器反应温度30℃,系统压力为常压条件下,气相出口亚硝酸甲酯体积含量为33%,基于氧气的产物收率为84.6%。In the tubular reactor ①, the inlet NO/O 2 molar ratio is 4, the gas phase N 2 volume content is 60%, the pre-reaction temperature is 100°C, and the reaction residence time is 1.2s. Parallel multi-channel (parallel number 30) microreactor ② hydraulic diameter 1000 microns, gas phase space velocity 50000h -1 , gas phase N 2 volume content 60%, NO/O 2 =4, methanol/NO molar ratio 1.5, micro reaction Under the conditions of the reactor reaction temperature of 30° C. and the system pressure of normal pressure, the volume content of methyl nitrite at the outlet of the gas phase is 33%, and the product yield based on oxygen is 84.6%.

Claims (4)

1.一种微反应器合成亚硝酸甲酯的方法,其特征在于:所述方法包含预反应和微反应两个步骤,预反应步骤生成含氮氧化合物的混合气体,微反应步骤合成亚硝酸甲酯。1. a method for the synthesis of methyl nitrite by a microreactor, characterized in that: the method comprises two steps of pre-reaction and micro-reaction, the pre-reaction step generates the mixed gas containing nitrogen oxide compound, and the micro-reaction step synthesizes nitrous acid methyl ester. 2.如权利要求1所述微反应器连续合成亚硝酸甲酯的方法,其特征在于:所述预反应步骤采用管式反应器,使包含NO、O2、N2的混合气体在该管式反应器中反应生成含N2、N2O3和NO2的混合气,反应在常温下进行,气体停留时间在1~15min;或,反应在80~120℃反应,停留时间1~2秒;管式反应器入口气体中NO与O2摩尔比为4~7,N2体积含量为40~70%;2. the method for continuously synthesizing methyl nitrite by microreactor as claimed in claim 1, is characterized in that: described pre-reaction step adopts tubular reactor, makes the mixed gas that comprises NO, O 2 , N 2 in this tube A mixed gas containing N 2 , N 2 O 3 and NO 2 is generated in a type reactor. The reaction is carried out at room temperature, and the gas residence time is 1-15 minutes; or, the reaction is performed at 80-120°C, and the residence time is 1-2 minutes. seconds; the molar ratio of NO to O2 in the inlet gas of the tubular reactor is 4-7, and the volume content of N2 is 40-70%; 所述微反应在单通道微反应器或多通道微反应器中进行,使甲醇与含氮氧化合物的混合气体反应生成亚硝酸甲酯;微反应器内甲醇与原料NO摩尔比为1~2,优选为1.2~1.5;压力范围为0.1~0.5MPa,优选为0.1~0.3MPa。The micro-reaction is carried out in a single-channel micro-reactor or a multi-channel micro-reactor, so that methanol and a mixed gas containing nitrogen oxides react to generate methyl nitrite; the molar ratio of methanol to raw material NO in the micro-reactor is 1-2 , preferably 1.2 to 1.5; the pressure range is 0.1 to 0.5 MPa, preferably 0.1 to 0.3 MPa. 3.如权利要求2所述微反应器连续合成亚硝酸甲酯的方法,其特征在于:所述管式反应器入口气体中NO与O2摩尔比为4~5,N2体积含量为50-55%。3. the method for continuously synthesizing methyl nitrite by microreactor as claimed in claim 2 , is characterized in that: NO and O in the inlet gas of described tubular reactor mol ratio is 4~ 5 , and N volume content is 50 -55%. 4.如权利要求2所述连续合成亚硝酸甲酯的方法,其特征在于:所述微反应器,微反应通道中的单通道和/或多通道的水力直径为100~3000微米,长度10~100厘米,微反应器空速为2000~50000h-1,反应温度为0~50℃。4. the method for continuously synthesizing methyl nitrite as claimed in claim 2, is characterized in that: described microreactor, the hydraulic diameter of single channel and/or multichannel in the micro reaction channel is 100~3000 microns, length 10 ~100 cm, the space velocity of the microreactor is 2000~50000h -1 , and the reaction temperature is 0~50°C.
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CN110683955A (en) * 2018-11-30 2020-01-14 中国科学院大连化学物理研究所 Micro-reaction system and method for efficiently preparing methyl nitrite
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CN116444399A (en) * 2023-04-26 2023-07-18 济南大学 Method for synthesizing (2E) -2-cyano-2-hydroxy iminoacetic acid ethyl ester by micro-reaction

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