TWI686377B - Apparatus and method for manufacturing dimethylhexane-1,6-dicarbamate - Google Patents

Apparatus and method for manufacturing dimethylhexane-1,6-dicarbamate Download PDF

Info

Publication number
TWI686377B
TWI686377B TW107135353A TW107135353A TWI686377B TW I686377 B TWI686377 B TW I686377B TW 107135353 A TW107135353 A TW 107135353A TW 107135353 A TW107135353 A TW 107135353A TW I686377 B TWI686377 B TW I686377B
Authority
TW
Taiwan
Prior art keywords
column
dicarbamate
item
liquid product
patent application
Prior art date
Application number
TW107135353A
Other languages
Chinese (zh)
Other versions
TW202014404A (en
Inventor
王聖潔
許家銘
陳佑廷
汪上曉
Original Assignee
國立清華大學
長春人造樹脂廠股份有限公司
長春石油化學股份有限公司
大連化學工業股份有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 國立清華大學, 長春人造樹脂廠股份有限公司, 長春石油化學股份有限公司, 大連化學工業股份有限公司 filed Critical 國立清華大學
Priority to TW107135353A priority Critical patent/TWI686377B/en
Application granted granted Critical
Publication of TWI686377B publication Critical patent/TWI686377B/en
Publication of TW202014404A publication Critical patent/TW202014404A/en

Links

Images

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

An apparatus and a method for manufacturing dimethylhexane-1,6-dicarbamate (HDC) are provided. The apparatus includes a reactor, a supply device of 1,6-hexanediamine (HDA), a supply device of dimethyl carbonate (DMC) and a first distillation column. The supply device of HDA is connected to the reactor. The supply device of DMC is connected to the reactor. The first distillation column is connected to a product outlet of the reactor. The first distillation column includes an upper column, a lower column and a compressor. The compressor is connected between a gas outlet of the lower column and a gas inlet of the upper column. The apparatus and the method for manufacturing HDC can effectively reduce the energy consumption and the production cost in the production of HDC.

Description

六亞甲基-1,6-二氨基甲酸甲酯的製造裝置及製造方法Manufacturing device and manufacturing method of hexamethylene-1,6-dicarbamic acid methyl ester

本發明是有關於一種化合物的製造裝置及製造方法，且特別是有關於一種六亞甲基-1,6-二氨基甲酸甲酯(dimethylhexane-1,6-dicarbamate，HDC)的製造裝置及製造方法。The invention relates to a compound manufacturing device and manufacturing method, and in particular to a manufacturing device and manufacturing of hexamethylene-1,6-dicarbamate (HDC) method.

六亞甲基-1,6-二異氰酸酯(hexamethylene-1,6-diisocyanate，HDI)這類脂肪族異氰酸酯是聚氨酯(PU)工業的重要原料，利用HDI生產的PU具有保色、保光、抗粉化、耐曬、耐油、耐磨等特點，此為芳香族異氰酸酯生產的PU所不及。Hexamethylene-1,6-diisocyanate (hexadiethylene-1,6-diisocyanate, HDI) such as aliphatic isocyanate is an important raw material for the polyurethane (PU) industry, PU produced by HDI has color retention, gloss retention, resistance Powdering, light resistance, oil resistance, wear resistance, etc., this is unmatched by PU produced by aromatic isocyanate.

HDI傳統上是由1,6-己二胺(1,6-hexanediamine，HDA)經光氣化合成，但此法有光氣極端毒性和副產物鹽酸嚴重腐蝕的缺點。因此，HDI的有效且環保的合成方法受到高度的注意。最近，以HDA為原料使用兩個步驟合成HDI的非光氣方法引起很多關注，第一步是HDC的合成，第二步是HDC進行熱裂解生成HDI。在這種方法中，HDC是一種中間體，其合成在整個HDI生產過程扮演重要腳色。HDI is traditionally synthesized from 1,6-hexanediamine (HDA) via phosgenation, but this method has the disadvantages of extreme toxicity of phosgene and severe corrosion of by-product hydrochloric acid. Therefore, the effective and environmentally friendly synthesis method of HDI has received high attention. Recently, a non-phosgene method using two steps to synthesize HDI using HDA as a raw material has attracted much attention. The first step is the synthesis of HDC, and the second step is the thermal cracking of HDC to generate HDI. In this method, HDC is an intermediate, and its synthesis plays an important role in the entire HDI production process.

然而，在生產HDC時的能耗與生產成本高。因此，如何有效地降低在生產HDC時的能耗與生產成本為目前持續努力的目標。However, the energy consumption and production cost when producing HDC are high. Therefore, how to effectively reduce the energy consumption and production cost in the production of HDC is the goal of continuous efforts at present.

本發明提供一種HDC的製造裝置與製造方法，其可大幅度降低在生產HDC時的能耗與生產成本。The invention provides an HDC manufacturing device and manufacturing method, which can greatly reduce the energy consumption and production cost when producing HDC.

本發明提出一種HDC的製造裝置，包括反應器、HDA供應裝置、碳酸二甲酯(dimethyl carbonate，DMC)供應裝置與第一蒸餾塔。HDA供應裝置連接至反應器。DMC供應裝置連接至反應器。第一蒸餾塔連接至反應器的出料口。第一蒸餾塔包括上段塔、下段塔與壓縮機。壓縮機連接在下段塔的氣體出口與上段塔的氣體入口之間。The invention provides an HDC manufacturing device, including a reactor, an HDA supply device, a dimethyl carbonate (DMC) supply device, and a first distillation tower. The HDA supply device is connected to the reactor. The DMC supply device is connected to the reactor. The first distillation column is connected to the discharge port of the reactor. The first distillation column includes an upper column, a lower column and a compressor. The compressor is connected between the gas outlet of the lower tower and the gas inlet of the upper tower.

依照本發明的一實施例所述，在上述HDC的製造裝置中，在反應器中可具有觸媒。According to an embodiment of the present invention, in the above HDC manufacturing apparatus, a catalyst may be provided in the reactor.

依照本發明的一實施例所述，在上述HDC的製造裝置中，上段塔的液體出口可連接至下段塔的液體入口。According to an embodiment of the present invention, in the above HDC manufacturing apparatus, the liquid outlet of the upper column can be connected to the liquid inlet of the lower column.

依照本發明的一實施例所述，在上述HDC的製造裝置中，上段塔的塔頂氣體產物溫度高於下段塔的塔底液體產物溫度。According to an embodiment of the present invention, in the above HDC manufacturing apparatus, the temperature of the gas product at the top of the upper column is higher than the temperature of the liquid product at the bottom of the lower column.

依照本發明的一實施例所述，在上述HDC的製造裝置中，上段塔的塔頂氣體產物溫度可比下段塔的塔底液體產物溫度高5°C以上。According to an embodiment of the present invention, in the above HDC manufacturing apparatus, the temperature of the gas product at the top of the upper column may be higher than the temperature of the liquid product at the bottom of the lower column by more than 5°C.

依照本發明的一實施例所述，在上述HDC的製造裝置中，上段塔中的壓力大於下段塔中的壓力。According to an embodiment of the present invention, in the above HDC manufacturing apparatus, the pressure in the upper column is greater than the pressure in the lower column.

依照本發明的一實施例所述，在上述HDC的製造裝置中，更包括第一再沸器。第一再沸器連接至下段塔的塔底。可將上段塔的塔頂氣體產物作為第一再沸器的熱源。According to an embodiment of the invention, the HDC manufacturing device further includes a first reboiler. The first reboiler is connected to the bottom of the lower column. The top gas product of the upper column can be used as the heat source of the first reboiler.

依照本發明的一實施例所述，在上述HDC的製造裝置中，更包括第二再沸器。第二再沸器連接至下段塔的塔底。According to an embodiment of the present invention, the HDC manufacturing apparatus further includes a second reboiler. The second reboiler is connected to the bottom of the lower column.

依照本發明的一實施例所述，在上述HDC的製造裝置中，更包括第二蒸餾塔。第二蒸餾塔連接至下段塔的塔底。According to an embodiment of the present invention, the HDC manufacturing device further includes a second distillation column. The second distillation column is connected to the bottom of the lower column.

依照本發明的一實施例所述，在上述HDC的製造裝置中，更包括萃取蒸餾塔。萃取蒸餾塔連接至上段塔的塔頂。According to an embodiment of the present invention, the HDC manufacturing apparatus further includes an extractive distillation column. The extractive distillation column is connected to the top of the upper column.

依照本發明的一實施例所述，在上述HDC的製造裝置中，更包括萃取劑回收塔。萃取劑回收塔連接至萃取蒸餾塔的塔底。According to an embodiment of the present invention, the HDC manufacturing device further includes an extractant recovery tower. The extractant recovery tower is connected to the bottom of the extractive distillation tower.

依照本發明的一實施例所述，在上述HDC的製造裝置中，可將第二蒸餾塔的塔底液體產物作為連接至萃取蒸餾塔的塔底的再沸器、連接至萃取劑回收塔的塔底的再沸器與連接在上段塔與萃取蒸餾塔之間的熱交換器中的至少一者的熱源。According to an embodiment of the present invention, in the above HDC manufacturing apparatus, the liquid product at the bottom of the second distillation column can be used as a reboiler connected to the bottom of the extractive distillation column and connected to the extractant recovery column. The reboiler at the bottom of the column and the heat source of at least one of the heat exchangers connected between the upper column and the extractive distillation column.

依照本發明的一實施例所述，在上述HDC的製造裝置中，可將萃取劑回收塔的塔底液體產物作為連接在上段塔與萃取蒸餾塔之間的熱交換器的熱源。According to an embodiment of the present invention, in the above HDC manufacturing apparatus, the bottom liquid product of the extractant recovery column can be used as the heat source of the heat exchanger connected between the upper column and the extractive distillation column.

本發明提出一種HDC的製造方法，包括以下步驟。在反應器中，使HDA與DMC在存在觸媒的環境下進行反應，而產生反應後之產物。使反應後之產物進入第一蒸餾塔中，而產生第一塔頂氣體產物與第一塔底液體產物。第一蒸餾塔包括上段塔、下段塔與壓縮機。由上段塔產生第一塔頂氣體產物。由下段塔產生第一塔底液體產物。壓縮機連接在下段塔的氣體出口與上段塔的氣體入口之間。The invention provides a method for manufacturing HDC, including the following steps. In the reactor, HDA and DMC are reacted in the presence of a catalyst to produce a product after the reaction. The product after the reaction enters the first distillation column to produce the first gas product at the top of the column and the liquid product at the bottom of the first column. The first distillation column includes an upper column, a lower column and a compressor. The first overhead gas product is produced from the upper column. The first bottom liquid product is produced from the lower column. The compressor is connected between the gas outlet of the lower tower and the gas inlet of the upper tower.

依照本發明的一實施例所述，在上述HDC的製造方法中，上段塔的液體出口可連接至下段塔的液體入口。According to an embodiment of the present invention, in the above HDC manufacturing method, the liquid outlet of the upper column can be connected to the liquid inlet of the lower column.

依照本發明的一實施例所述，在上述HDC的製造方法中，上段塔的塔頂氣體產物溫度高於下段塔的塔底液體產物溫度。According to an embodiment of the present invention, in the above HDC manufacturing method, the temperature of the gas product at the top of the upper column is higher than the temperature of the liquid product at the bottom of the lower column.

依照本發明的一實施例所述，在上述HDC的製造方法中，上段塔的塔頂氣體產物溫度可比下段塔的塔底液體產物溫度高5°C以上。According to an embodiment of the present invention, in the above HDC manufacturing method, the temperature of the gas product at the top of the upper column may be higher than the temperature of the liquid product at the bottom of the lower column by more than 5°C.

依照本發明的一實施例所述，在上述HDC的製造方法中，上段塔中的壓力大於下段塔中的壓力。According to an embodiment of the present invention, in the above HDC manufacturing method, the pressure in the upper column is greater than the pressure in the lower column.

依照本發明的一實施例所述，在上述HDC的製造方法中，在HDA與DMC的反應中，可使用過量的DMC作為反應物。According to an embodiment of the present invention, in the above HDC manufacturing method, in the reaction of HDA and DMC, excess DMC may be used as a reactant.

依照本發明的一實施例所述，在上述HDC的製造方法中，在HDA與DMC的反應中，DMC與HDA的進料莫耳比值例如是3至9。According to an embodiment of the present invention, in the above HDC manufacturing method, in the reaction of HDA and DMC, the feed molar ratio of DMC to HDA is, for example, 3 to 9.

依照本發明的一實施例所述，在上述HDC的製造方法中，反應後之產物可包括HDC、甲醇(methanol，MeOH)與DMC。第一塔頂氣體產物可包括MeOH與DMC。第一塔底液體產物可包括HDC與DMC。According to an embodiment of the present invention, in the above HDC manufacturing method, the products after the reaction may include HDC, methanol (MeOH), and DMC. The first overhead gas product may include MeOH and DMC. The first bottom liquid product may include HDC and DMC.

依照本發明的一實施例所述，在上述HDC的製造方法中，可將上段塔的第一塔頂氣體產物作為連接至下段塔的塔底的再沸器的熱源。According to an embodiment of the present invention, in the above HDC manufacturing method, the first overhead gas product of the upper column can be used as the heat source of the reboiler connected to the bottom of the lower column.

依照本發明的一實施例所述，在上述HDC的製造方法中，更可包括使第一塔底液體產物進入第二蒸餾塔中，而產生第二塔頂液體產物與第二塔底液體產物。According to an embodiment of the present invention, in the above-mentioned HDC manufacturing method, it may further include allowing the first bottom liquid product to enter the second distillation column to produce a second top liquid product and a second bottom liquid product .

依照本發明的一實施例所述，在上述HDC的製造方法中，第二塔頂液體產物可包括DMC。第二塔底液體產物可包括HDC。According to an embodiment of the invention, in the above HDC manufacturing method, the second overhead liquid product may include DMC. The second bottom liquid product may include HDC.

依照本發明的一實施例所述，在上述HDC的製造方法中，更可包括使第一塔頂氣體產物經冷凝後所得的第一塔頂液體產物與萃取劑進入萃取蒸餾塔中，而產生第三塔頂液體產物與第三塔底液體產物。According to an embodiment of the present invention, in the above HDC manufacturing method, it may further include that the first overhead liquid product and the extractant obtained after the condensation of the first overhead gas product are condensed into an extractive distillation column to produce The liquid product at the top of the third column and the liquid product at the bottom of the third column.

依照本發明的一實施例所述，在上述HDC的製造方法中，第三塔頂液體產物可包括MeOH。第三塔底液體產物可包括DMC與萃取劑。According to an embodiment of the invention, in the above HDC manufacturing method, the third overhead liquid product may include MeOH. The third bottom liquid product may include DMC and extractant.

依照本發明的一實施例所述，在上述HDC的製造方法中，更可包括使第三塔底液體產物進入萃取劑回收塔中，而產生第四塔頂液體產物與第四塔底液體產物。According to an embodiment of the present invention, in the above-mentioned HDC manufacturing method, it may further include allowing the third bottom liquid product to enter the extractant recovery column to produce a fourth top liquid product and a fourth bottom liquid product .

依照本發明的一實施例所述，在上述HDC的製造方法中，第四塔頂液體產物可包括DMC。第四塔底液體產物可包括萃取劑。According to an embodiment of the present invention, in the above HDC manufacturing method, the fourth overhead liquid product may include DMC. The fourth bottom liquid product may include an extractant.

依照本發明的一實施例所述，在上述HDC的製造方法中，可將第二蒸餾塔的第二塔底液體產物作為連接至萃取蒸餾塔的塔底的再沸器、連接至萃取劑回收塔的塔底的再沸器與連接在上段塔與萃取蒸餾塔之間的熱交換器中的至少一者的熱源。According to an embodiment of the present invention, in the above-mentioned HDC manufacturing method, the second bottom liquid product of the second distillation column can be used as a reboiler connected to the bottom of the extractive distillation column and connected to the extractant recovery The reboiler at the bottom of the column and the heat source of at least one of the heat exchangers connected between the upper column and the extractive distillation column.

依照本發明的一實施例所述，在上述HDC的製造方法中，可將萃取劑回收塔的第四塔底液體產物作為連接在上段塔與萃取蒸餾塔之間的熱交換器的熱源。According to an embodiment of the present invention, in the above HDC manufacturing method, the fourth bottom liquid product of the extractant recovery column can be used as the heat source of the heat exchanger connected between the upper column and the extractive distillation column.

基於上述，在上述HDC的製造裝置與製造方法中，由於下段塔操作在低壓，所以可有效地降低下段塔的塔底再沸器能耗(reboiler duty)。另外，由於DMC-MeOH共沸物的DMC組成會隨壓力的增加而減少，因此上段塔的壓力因壓縮機的加入而增加，將趨使更多的DMC可往下段塔的塔底收集，如此可明顯降低下段塔的塔底與上段塔的塔頂間之溫差，大幅減少壓縮機的設備費與操作成本，且上段塔的塔頂氣體產物在高溫高壓下，可成為下段塔的塔底再沸器的熱源。另一方面，由於上段塔的塔頂氣體產物的DMC組成更接近DMC-MeOH共沸物的DMC組成，此將減少萃取蒸餾系統分離DMC與MeOH混合物時所需的設備費與操作成本，因此本發明所提的架構可大幅度降低在生產HDC的整個製程的能耗與生產成本。Based on the above, in the above-mentioned HDC manufacturing apparatus and manufacturing method, since the lower column is operated at a low pressure, the bottom reboiler energy consumption (reboiler duty) of the lower column can be effectively reduced. In addition, since the DMC composition of the DMC-MeOH azeotrope will decrease with increasing pressure, the pressure of the upper column will increase due to the addition of the compressor, which will tend to collect more DMC to the bottom of the lower column. It can significantly reduce the temperature difference between the bottom of the lower tower and the top of the upper tower, greatly reducing the equipment cost and operating cost of the compressor, and the gas product at the top of the upper tower can become the bottom of the lower tower under high temperature and high pressure. The heat source of the boiler. On the other hand, since the DMC composition of the top gas product of the upper column is closer to the DMC composition of the DMC-MeOH azeotrope, this will reduce the equipment cost and operating cost required for the extractive distillation system to separate the DMC and MeOH mixture. The architecture proposed by the invention can greatly reduce the energy consumption and production cost of the entire process of producing HDC.

為讓本發明的上述特徵和優點能更明顯易懂，下文特舉實施例，並配合所附圖式作詳細說明如下。In order to make the above-mentioned features and advantages of the present invention more obvious and understandable, the embodiments are specifically described below in conjunction with the accompanying drawings for detailed description as follows.

圖1為本發明一實施例的HDC的製造裝置的示意圖。FIG. 1 is a schematic diagram of an HDC manufacturing apparatus according to an embodiment of the invention.

請參照圖1，HDC的製造裝置100包括反應器102、HDA供應裝置104、DMC供應裝置106與蒸餾塔108。HDC的製造裝置100適用於使HDA與DMC在存在觸媒的環境下進行反應，以製造HDC。Referring to FIG. 1, the HDC manufacturing device 100 includes a reactor 102, an HDA supply device 104, a DMC supply device 106 and a distillation column 108. The HDC manufacturing apparatus 100 is suitable for reacting HDA and DMC in the presence of a catalyst to manufacture HDC.

反應器102包括連續式反應器或批次反應器。在本實施例中，反應器102的數量是以一個為例來進行說明，但本發明並不以此為限，於此技術領域具有通常知識者可依照製程設計來調整反應器102的數量。舉例來說，在其他實施例中，反應器102的數量亦可為兩個以上。此外，在反應器102中可具有觸媒。觸媒可提高反應物的反應轉化率且可加速反應。觸媒例如是乙酸錳(Mn(OAc) 2)或苯酚鈉(C 6H 5ONa)。 The reactor 102 includes a continuous reactor or a batch reactor. In this embodiment, the number of reactors 102 is described as an example, but the invention is not limited thereto. Those skilled in the art can adjust the number of reactors 102 according to the process design. For example, in other embodiments, the number of the reactor 102 may be more than two. In addition, there may be a catalyst in the reactor 102. The catalyst can improve the reaction conversion rate of the reactants and can accelerate the reaction. The catalyst is, for example, manganese acetate (Mn(OAc) 2 ) or sodium phenolate (C 6 H 5 ONa).

HDA供應裝置104連接至反應器102，可用以提供HDA至反應器102中。DMC供應裝置106連接至反應器102，可用以提供DMC至反應器102中。在一實施例中，在HDA供應裝置104與反應器102之間以及DMC供應裝置106與反應器102之間可設置儲存槽(未示出)，藉此可將HDA與DMC在儲存槽中進行預混，再將儲存槽中的HDA與DMC的混合物供應至反應器102中，但本發明並不以此為限。在另一實施例中，HDA供應裝置104的輸送管路與DMC供應裝置106的輸送管路可先會合後，再連接至反應器102，藉此可將HDA與DMC在輸送管路中進行預混，再將HDA與DMC的混合物供應至反應器102中。在另一實施例中，HDA供應裝置104與DMC供應裝置106亦可分別將HDA與DMC供應至反應器102中。The HDA supply device 104 is connected to the reactor 102 and can be used to provide HDA into the reactor 102. The DMC supply device 106 is connected to the reactor 102 and can be used to provide DMC into the reactor 102. In one embodiment, a storage tank (not shown) may be provided between the HDA supply device 104 and the reactor 102 and between the DMC supply device 106 and the reactor 102, whereby HDA and DMC may be performed in the storage tank Premix, and then supply the mixture of HDA and DMC in the storage tank to the reactor 102, but the invention is not limited to this. In another embodiment, the delivery pipeline of the HDA supply device 104 and the delivery pipeline of the DMC supply device 106 may be first merged and then connected to the reactor 102, whereby the HDA and DMC may be pre-treated in the delivery pipeline Mix, and then supply the mixture of HDA and DMC to the reactor 102. In another embodiment, the HDA supply device 104 and the DMC supply device 106 can also supply HDA and DMC to the reactor 102, respectively.

基於上述，在反應器102中，可發生的反應如下。 HDA + DMC → HMC + MeOH HMC + DMC → HDC + MeOH 上述反應的總反應式如下。 HDA + 2DMC → HDC + 2MeOH 其中，HMC為六亞甲基-1,6-單氨基甲酸甲酯(dimethylhexane-1,6-monocarbamate)。HDC為本反應系統的主產物。Based on the above, the reactions that can occur in the reactor 102 are as follows. HDA + DMC → HMC + MeOH HMC + DMC → HDC + MeOH The overall reaction formula of the above reaction is as follows. HDA + 2DMC → HDC + 2MeOH where HMC is hexamethylene-1,6-monocarbamate (dimethylhexane-1,6-monocarbamate). HDC is the main product of the reaction system.

蒸餾塔108連接至反應器102的出料口102a。蒸餾塔108包括上段塔110、下段塔112與壓縮機114，且更可包括洩壓閥115。在本實施例中，是以上段塔110連接至反應器102的出料口102a為例，但本發明並不以此為限。壓縮機114連接在下段塔112的氣體出口112a與上段塔110的氣體入口110a之間。此外，上段塔110的液體出口110b可連接至下段塔112的液體入口112b。洩壓閥115可連接在上段塔110的液體出口110b與下段塔112的液體入口112b之間。舉例來說，上段塔110的氣體入口110a與液體出口110b可位在上段塔110的塔底，且下段塔112的氣體出口112a與液體入口112b可位在下段塔112的塔頂，但本發明並不以此為限。The distillation column 108 is connected to the discharge port 102a of the reactor 102. The distillation column 108 includes an upper column 110, a lower column 112, and a compressor 114, and may further include a pressure relief valve 115. In this embodiment, the example in which the upper column 110 is connected to the discharge port 102a of the reactor 102 is taken as an example, but the present invention is not limited thereto. The compressor 114 is connected between the gas outlet 112a of the lower column 112 and the gas inlet 110a of the upper column 110. In addition, the liquid outlet 110b of the upper column 110 may be connected to the liquid inlet 112b of the lower column 112. The pressure relief valve 115 may be connected between the liquid outlet 110b of the upper column 110 and the liquid inlet 112b of the lower column 112. For example, the gas inlet 110a and the liquid outlet 110b of the upper tower 110 may be located at the bottom of the upper tower 110, and the gas outlet 112a and the liquid inlet 112b of the lower tower 112 may be located at the top of the lower tower 112, but the present invention Not limited to this.

藉由壓縮機114的運轉，上段塔110中的壓力大於下段塔112中的壓力。由於下段塔112操作在低壓，因此可有效地降低下段塔112的塔底的再沸器能耗，進而大幅度降低在生產HDC時的能耗與生產成本。By the operation of the compressor 114, the pressure in the upper column 110 is greater than the pressure in the lower column 112. Since the lower column 112 operates at a low pressure, the energy consumption of the reboiler at the bottom of the lower column 112 can be effectively reduced, thereby greatly reducing the energy consumption and production cost when producing HDC.

此外，由於壓縮機114可提高上段塔110中的壓力，因此趨使DMC更有利從下段塔112的塔底收集，此將使上段塔110的塔頂的DMC組成較接近DMC-MeOH共沸物的DMC組成，因而降低萃取蒸餾系統的能耗與成本。此外，在降低上段塔110中的DMC的含量時，需同時考慮到上段塔110的塔頂氣體產物中的MeOH與DMC的含量。舉例來說，若上段塔110的塔頂氣體產物中的MeOH與DMC的含量比值接近共沸組成，則會使得下段塔112的塔底的再沸器能耗大幅提升，因此可對上段塔110的塔頂氣體產物中的MeOH與DMC的含量比進行最適化。In addition, since the compressor 114 can increase the pressure in the upper column 110, DMC tends to be more favorable to collect from the bottom of the lower column 112, which will make the DMC composition at the top of the upper column 110 closer to the DMC-MeOH azeotrope The DMC composition reduces the energy consumption and cost of the extractive distillation system. In addition, when reducing the content of DMC in the upper column 110, the contents of MeOH and DMC in the gas product at the top of the upper column 110 must be considered simultaneously. For example, if the ratio of the content of MeOH and DMC in the top gas product of the upper column 110 is close to the azeotropic composition, the energy consumption of the reboiler at the bottom of the lower column 112 will be greatly increased, so the upper column 110 The content ratio of MeOH to DMC in the overhead gas product is optimized.

另外，在上段塔110中的壓力提高的情況下，可提高上段塔110的塔頂氣體產物溫度，而有利於產物的後續利用(如，可將上段塔110的塔頂氣體產物作為再沸器116的熱源)，進而降低在生產HDC時的能耗與生產成本。上段塔110的塔頂氣體產物溫度高於下段塔112的塔底液體產物溫度。舉例來說，上段塔110的塔頂氣體產物溫度可比下段塔112的塔底液體產物溫度高5°C以上。在一實施例中，上段塔110的塔頂氣體產物溫度可比下段塔112的塔底液體產物溫度高10°C以上。In addition, when the pressure in the upper column 110 is increased, the temperature of the top gas product of the upper column 110 can be increased, which is beneficial to the subsequent utilization of the product (for example, the top gas product of the upper column 110 can be used as a reboiler 116 heat source), which in turn reduces energy consumption and production costs when producing HDC. The temperature of the gas product at the top of the upper column 110 is higher than the temperature of the liquid product at the bottom of the lower column 112. For example, the temperature of the gas product at the top of the upper column 110 may be higher than the temperature of the liquid product at the bottom of the lower column 112 by more than 5°C. In one embodiment, the temperature of the gas product at the top of the upper column 110 may be higher than the temperature of the liquid product at the bottom of the lower column 112 by more than 10°C.

HDC的製造裝置100更可選擇性地包括再沸器116、再沸器118、回流槽(reflux drum)120、冷凝器122、蒸餾塔124、再沸器126、回流槽128、冷凝器130、萃取蒸餾塔132、熱交換器134、再沸器136、再沸器138、回流槽140、冷凝器142、萃取劑回收塔144、再沸器146、再沸器148、回流槽150、冷凝器152、熱交換器154與冷凝器156中的至少一者。The HDC manufacturing apparatus 100 can optionally include a reboiler 116, a reboiler 118, a reflux drum 120, a condenser 122, a distillation column 124, a reboiler 126, a reflux tank 128, a condenser 130, Extractive distillation column 132, heat exchanger 134, reboiler 136, reboiler 138, reflux tank 140, condenser 142, extractant recovery tower 144, reboiler 146, reboiler 148, reflux tank 150, condenser 152. At least one of the heat exchanger 154 and the condenser 156.

再沸器116連接至下段塔112的塔底，以提供熱量給下段塔112。由於上段塔110的塔頂氣體產物溫度高於下段塔112的塔底液體產物溫度，因此可將上段塔110的塔頂氣體產物作為再沸器116的熱源，且藉由進行上述熱整合可更進一步地降低能耗與生產成本。詳細來說，上段塔110的塔頂氣體產物可將潛熱釋放給下段塔110的再沸器116，而降低塔頂氣體產物的溫度或者使塔頂氣體產物成為塔頂液體產物。The reboiler 116 is connected to the bottom of the lower column 112 to provide heat to the lower column 112. Since the temperature of the top gas product of the upper column 110 is higher than the temperature of the bottom liquid product of the lower column 112, the top gas product of the upper column 110 can be used as the heat source of the reboiler 116, and by performing the above heat integration Further reduce energy consumption and production costs. In detail, the overhead gas product of the upper column 110 can release latent heat to the reboiler 116 of the lower column 110, thereby reducing the temperature of the overhead gas product or making the overhead gas product an overhead liquid product.

再沸器118連接至下段塔112的塔底，可作為下段塔112的輔助熱源(auxiliary heat source)。在再沸器116可提供足夠的熱量給下段塔112的情況下，亦可省略再沸器118。The reboiler 118 is connected to the bottom of the lower column 112 and can serve as an auxiliary heat source for the lower column 112. In the case where the reboiler 116 can provide sufficient heat to the lower column 112, the reboiler 118 can also be omitted.

回流槽120連接至上段塔110的塔頂，可用以儲存上段塔110的塔頂氣體產物經再沸器116進行熱交換或再經冷凝器122冷凝後的塔頂液體產物，且回流槽120中的部分塔頂液體產物可回流至上段塔110中。The reflux tank 120 is connected to the top of the upper tower 110, and can be used to store the top gas product of the upper tower 110 through the reboiler 116 for heat exchange or condensed by the condenser 122, and the top liquid product in the reflux tank 120 A part of the liquid product at the top of the column can be refluxed into the upper column 110.

冷凝器122連接在再沸器116與回流槽120之間。在再沸器116中進行熱交換後的塔頂氣體產物或塔頂液體產物可經冷凝器122冷凝後再進入回流槽120中。在另一實施例中，在再沸器116中進行熱交換後的上段塔110的塔頂氣體產物已成為達預定溫度的塔頂液體產物的情況下，亦可省略冷凝器122。The condenser 122 is connected between the reboiler 116 and the reflux tank 120. The top gas product or top liquid product after heat exchange in the reboiler 116 can be condensed by the condenser 122 and then enter the reflux tank 120. In another embodiment, the condenser 122 may be omitted when the top gas product of the upper column 110 after heat exchange in the reboiler 116 has become the top liquid product at a predetermined temperature.

蒸餾塔124連接至下段塔112的塔底。再沸器126連接至蒸餾塔124的塔底，以提供熱量給蒸餾塔124。回流槽128連接至蒸餾塔124的塔頂，可用以儲存蒸餾塔124的塔頂液體產物，且回流槽128中的部分塔頂液體產物可回流至蒸餾塔124中。冷凝器130連接在蒸餾塔124的塔頂與回流槽128之間。蒸餾塔124的塔頂氣體產物可經冷凝器130冷凝後再進入回流槽128中。The distillation column 124 is connected to the bottom of the lower column 112. The reboiler 126 is connected to the bottom of the distillation column 124 to provide heat to the distillation column 124. The reflux tank 128 is connected to the top of the distillation column 124, and can be used to store the overhead liquid product of the distillation column 124, and a part of the overhead liquid product in the reflux tank 128 can be refluxed into the distillation column 124. The condenser 130 is connected between the top of the distillation column 124 and the reflux tank 128. The gas product at the top of the distillation column 124 can be condensed by the condenser 130 and then enter the reflux tank 128.

萃取蒸餾塔132連接至上段塔110的塔頂。在本實施例中，回流槽120可連接在上段塔110的塔頂與萃取蒸餾塔132之間。熱交換器134連接在回流槽120與萃取蒸餾塔132之間，以對來自回流槽120的進料進行加熱，藉此可降低萃取蒸餾塔132的塔底的再沸器能耗。在萃取蒸餾塔132中所添加的萃取劑例如是苯胺(aniline)或酚(phenol)。萃取劑可用於萃取蒸餾塔132中的DMC。再沸器136連接至萃取蒸餾塔132的塔底，以提供熱量給萃取蒸餾塔132。再沸器138連接至萃取蒸餾塔132的塔底，可作為萃取蒸餾塔132的輔助熱源。此外，在再沸器136可提供足夠的熱量給萃取蒸餾塔132的情況下，亦可省略再沸器138。回流槽140連接至萃取蒸餾塔132的塔頂，可用以儲存萃取蒸餾塔132的塔頂液體產物，且回流槽140中的部分塔頂液體產物可回流至萃取蒸餾塔132中。冷凝器142連接在萃取蒸餾塔132的塔頂與回流槽140之間。萃取蒸餾塔132的塔頂氣體產物可經冷凝器142冷凝後再進入回流槽140中。The extractive distillation column 132 is connected to the top of the upper column 110. In this embodiment, the reflux tank 120 may be connected between the top of the upper column 110 and the extractive distillation column 132. The heat exchanger 134 is connected between the reflux tank 120 and the extractive distillation column 132 to heat the feed from the reflux tank 120, thereby reducing the energy consumption of the reboiler at the bottom of the extractive distillation column 132. The extractant added in the extractive distillation column 132 is, for example, aniline or phenol. The extractant can be used to extract DMC in the distillation column 132. The reboiler 136 is connected to the bottom of the extractive distillation column 132 to provide heat to the extractive distillation column 132. The reboiler 138 is connected to the bottom of the extractive distillation column 132 and can be used as an auxiliary heat source for the extractive distillation column 132. In addition, in the case where the reboiler 136 can provide sufficient heat to the extractive distillation column 132, the reboiler 138 can also be omitted. The reflux tank 140 is connected to the top of the extractive distillation column 132, and can be used to store the overhead liquid product of the extractive distillation column 132, and part of the overhead liquid product in the reflux tank 140 can be refluxed into the extractive distillation column 132. The condenser 142 is connected between the top of the extractive distillation column 132 and the reflux tank 140. The gas product at the top of the extractive distillation column 132 can be condensed by the condenser 142 before entering the reflux tank 140.

萃取劑回收塔144連接至萃取蒸餾塔132的塔底。再沸器146連接至萃取劑回收塔144的塔底，以提供熱量給萃取劑回收塔144。再沸器148連接至萃取劑回收塔144的塔底，可作為萃取劑回收塔144的輔助熱源。在再沸器146可提供足夠的熱量給萃取劑回收塔144的情況下，亦可省略再沸器148。回流槽150連接至萃取劑回收塔144的塔頂，可用以儲存萃取劑回收塔144的塔頂液體產物，且回流槽150中的部分塔頂液體產物可回流至萃取劑回收塔144中。冷凝器152連接在萃取劑回收塔144的塔頂與回流槽150之間。萃取劑回收塔144的塔頂氣體產物可經冷凝器152冷凝後再進入回流槽150中。萃取劑回收塔144的塔底液體產物中的萃取劑可回流至萃取蒸餾塔132中。The extractant recovery column 144 is connected to the bottom of the extractive distillation column 132. The reboiler 146 is connected to the bottom of the extractant recovery column 144 to provide heat to the extractant recovery column 144. The reboiler 148 is connected to the bottom of the extractant recovery tower 144 and can be used as an auxiliary heat source for the extractant recovery tower 144. In the case where the reboiler 146 can provide sufficient heat to the extractant recovery column 144, the reboiler 148 can also be omitted. The reflux tank 150 is connected to the top of the extractant recovery column 144, and can be used to store the top liquid product of the extractant recovery column 144, and a part of the top liquid product in the reflux tank 150 can be refluxed into the extractant recovery column 144. The condenser 152 is connected between the top of the extractant recovery column 144 and the reflux tank 150. The gas product at the top of the extractant recovery column 144 can be condensed by the condenser 152 before entering the reflux tank 150. The extractant in the liquid product at the bottom of the extractant recovery column 144 can be refluxed into the extractive distillation column 132.

此外，由於蒸餾塔124的塔底液體產物溫度可高於萃取蒸餾塔132的塔底液體產物溫度、萃取劑回收塔144的塔底液體產物溫度與萃取蒸餾塔132的進料溫度，因此可將蒸餾塔124的塔底液體產物作為連接至萃取蒸餾塔132的塔底的再沸器136、連接至萃取劑回收塔144的塔底的再沸器146與連接在上段塔110與萃取蒸餾塔132之間的熱交換器134中的至少一者的熱源，且藉由進行上述熱整合可更進一步地降低能耗與生產成本。In addition, since the temperature of the bottom liquid product of the distillation column 124 can be higher than the temperature of the bottom liquid product of the extractive distillation column 132, the temperature of the bottom liquid product of the extractant recovery column 144 and the feed temperature of the extractive distillation column 132, it can be The bottom liquid product of the distillation column 124 serves as a reboiler 136 connected to the bottom of the extractive distillation column 132, a reboiler 146 connected to the bottom of the extractant recovery column 144, and is connected to the upper column 110 and the extractive distillation column 132 The heat source of at least one of the heat exchangers 134 in between, and by performing the above heat integration, energy consumption and production costs can be further reduced.

熱交換器154連接在回流槽120與萃取蒸餾塔132之間，以對來自回流槽120的進料進行加熱，藉此可降低萃取蒸餾塔132的塔底的再沸器能耗。由於萃取劑回收塔144的塔底液體產物溫度可高於萃取蒸餾塔132的進料溫度，因此可將萃取劑回收塔144的塔底液體產物作為連接在上段塔110與萃取蒸餾塔132之間的熱交換器154的熱源，且藉由進行上述熱整合可更進一步地降低能耗與生產成本。The heat exchanger 154 is connected between the reflux tank 120 and the extractive distillation column 132 to heat the feed from the reflux tank 120, thereby reducing the energy consumption of the reboiler at the bottom of the extractive distillation column 132. Since the temperature of the bottom liquid product of the extractant recovery column 144 can be higher than the feed temperature of the extractive distillation column 132, the bottom liquid product of the extractant recovery column 144 can be connected between the upper column 110 and the extractive distillation column 132 The heat source of the heat exchanger 154, and by performing the above heat integration can further reduce energy consumption and production costs.

冷凝器156連接在萃取劑回收塔144的塔底與萃取蒸餾塔132之間。在熱交換器154中進行熱交換後的萃取劑回收塔144的塔底液體產物可經冷凝器156冷凝後再進入萃取蒸餾塔132中。The condenser 156 is connected between the bottom of the extractant recovery column 144 and the extractive distillation column 132. The liquid product at the bottom of the extractant recovery column 144 after heat exchange in the heat exchanger 154 can be condensed by the condenser 156 and then enter the extractive distillation column 132.

圖2為本發明一實施例的HDC的製造流程圖。以下，藉由圖2來說明本發明一實施例的HDC的製造方法。圖2的製造方法所使用的裝置是以圖1的HDC的製造裝置100為例，但本發明並不以此為限。此外，關於圖1的HDC的製造裝置100中的各構件的詳細內容可參考上述實施例，不再重複說明。FIG. 2 is a manufacturing flowchart of an HDC according to an embodiment of the invention. Hereinafter, a method of manufacturing an HDC according to an embodiment of the present invention will be described with reference to FIG. 2. The device used in the manufacturing method of FIG. 2 is an example of the HDC manufacturing device 100 of FIG. 1, but the invention is not limited thereto. In addition, for details of each component in the HDC manufacturing apparatus 100 of FIG. 1, reference may be made to the above-mentioned embodiment, and the description will not be repeated.

請參照圖2，進行步驟S100，在反應器102中，使HDA與DMC在存在觸媒的環境下進行反應，而產生反應後之產物。反應後之產物可包括HDC、MeOH與DMC，且更可包括微量的HDA、微量的高沸點中間產物(HMC)與微量的高沸點不純物。舉例來說，可藉由HDA供應裝置104與DMC供應裝置106分別提供HDA與DMC至反應器102中，以進行反應。在HDA與DMC的反應中，可使用過量的DMC作為反應物。在HDA與DMC的反應中，DMC與HDA的進料莫耳比值例如是3至9。在一實施例中，在HDA與DMC的反應中，DMC與HDA的進料莫耳比值例如是4至8。觸媒例如是乙酸錳(Mn(OAc) 2)或苯酚鈉(C 6H 5ONa)。 Referring to FIG. 2, step S100 is performed. In the reactor 102, HDA and DMC are reacted in the presence of a catalyst to produce a product after the reaction. The products after the reaction may include HDC, MeOH, and DMC, and may further include trace amounts of HDA, trace amounts of high-boiling intermediate products (HMC), and trace amounts of high-boiling impurities. For example, the HDA supply device 104 and the DMC supply device 106 can provide HDA and DMC to the reactor 102 to perform the reaction. In the reaction of HDA and DMC, excess DMC can be used as a reactant. In the reaction of HDA and DMC, the feed molar ratio of DMC to HDA is, for example, 3 to 9. In one embodiment, in the reaction of HDA and DMC, the feed molar ratio of DMC to HDA is, for example, 4 to 8. The catalyst is, for example, manganese acetate (Mn(OAc) 2 ) or sodium phenolate (C 6 H 5 ONa).

進行步驟S102，使反應後之產物進入蒸餾塔108中，而產生第一塔頂氣體產物與第一塔底液體產物。第一塔頂氣體產物可包括MeOH與DMC。第一塔底液體產物可包括HDC與DMC，且更可包括微量的HDA、微量的MeOH、微量的高沸點中間產物(HMC)與微量的高沸點不純物。Step S102 is carried out, so that the products after the reaction enter the distillation column 108 to produce the first gas product at the top of the column and the liquid product at the bottom of the first column. The first overhead gas product may include MeOH and DMC. The first bottom liquid product may include HDC and DMC, and may further include trace amounts of HDA, trace amounts of MeOH, trace amounts of high-boiling intermediate products (HMC) and trace amounts of high-boiling impurities.

蒸餾塔108包括上段塔110、下段塔112與壓縮機114，且更可包括洩壓閥115。由上段塔110產生第一塔頂氣體產物。由下段塔112產生第一塔底液體產物。壓縮機114連接在下段塔112的氣體出口112a與上段塔110的氣體入口110a之間。上段塔110的液體出口110b可連接至下段塔112的液體入口112b。洩壓閥115可連接在上段塔110的液體出口110b與下段塔112的液體入口112b之間。舉例來說，上段塔110的氣體入口110a與液體出口110b可位在上段塔110的塔底，且下段塔112的氣體出口112a與液體入口112b可位在下段塔112的塔頂，但本發明並不以此為限。The distillation column 108 includes an upper column 110, a lower column 112, and a compressor 114, and may further include a pressure relief valve 115. The first overhead gas product is produced from the upper column 110. The first bottom liquid product is produced from the lower column 112. The compressor 114 is connected between the gas outlet 112a of the lower column 112 and the gas inlet 110a of the upper column 110. The liquid outlet 110b of the upper column 110 may be connected to the liquid inlet 112b of the lower column 112. The pressure relief valve 115 may be connected between the liquid outlet 110b of the upper column 110 and the liquid inlet 112b of the lower column 112. For example, the gas inlet 110a and the liquid outlet 110b of the upper tower 110 may be located at the bottom of the upper tower 110, and the gas outlet 112a and the liquid inlet 112b of the lower tower 112 may be located at the top of the lower tower 112, but the present invention Not limited to this.

藉由壓縮機114的運轉，上段塔110中的壓力大於下段塔112中的壓力。上段塔110的塔頂氣體產物溫度高於下段塔112的塔底液體產物溫度，因此可將上段塔110的第一塔頂氣體產物作為連接至下段塔112的塔底的再沸器116的熱源，且藉由進行上述熱整合可更進一步地降低能耗與生產成本。舉例來說，上段塔110的塔頂氣體產物溫度可比下段塔112的塔底液體產物溫度高5°C以上。在一實施例中，上段塔110的塔頂氣體產物溫度可比下段塔112的塔底液體產物溫度高10°C以上。By the operation of the compressor 114, the pressure in the upper column 110 is greater than the pressure in the lower column 112. The temperature of the top gas product of the upper column 110 is higher than the temperature of the bottom liquid product of the lower column 112, so the first top gas product of the upper column 110 can be used as the heat source of the reboiler 116 connected to the bottom of the lower column 112 And, by performing the above heat integration, energy consumption and production costs can be further reduced. For example, the temperature of the gas product at the top of the upper column 110 may be higher than the temperature of the liquid product at the bottom of the lower column 112 by more than 5°C. In one embodiment, the temperature of the gas product at the top of the upper column 110 may be higher than the temperature of the liquid product at the bottom of the lower column 112 by more than 10°C.

基於上述可知，由於下段塔112操作在低壓，所以可有效地降低下段塔112的塔底再沸器能耗(reboiler duty)。另外，由於DMC-MeOH共沸物的DMC組成會隨壓力的增加而減少，因此上段塔110的壓力因壓縮機114的加入而增加，將趨使更多的DMC可往下段塔112的塔底收集，如此可明顯降低下段塔112的塔底與上段塔110的塔頂間之溫差，大幅減少壓縮機的設備費與操作成本，且上段塔110的塔頂氣體產物在高溫高壓下，可成為下段塔112的塔底再沸器的熱源。另一方面，由於上段塔110的塔頂氣體產物的DMC組成更接近DMC-MeOH共沸物的DMC組成，此將減少萃取蒸餾系統分離DMC與MeOH混合物時所需的設備費與操作成本，因此本發明所提的架構可大幅度降低在生產HDC的整個製程的能耗與生產成本。Based on the above, since the lower column 112 operates at a low pressure, the bottom reboiler duty of the lower column 112 can be effectively reduced. In addition, since the DMC composition of the DMC-MeOH azeotrope decreases with increasing pressure, the pressure of the upper column 110 increases due to the addition of the compressor 114, which will tend to allow more DMC to go to the bottom of the lower column 112 Collecting, this can significantly reduce the temperature difference between the bottom of the lower tower 112 and the top of the upper tower 110, greatly reducing the equipment cost and operating cost of the compressor, and the gas products at the top of the upper tower 110 at high temperature and pressure can become The heat source of the bottom reboiler of the lower column 112. On the other hand, since the DMC composition of the top gas product of the upper column 110 is closer to the DMC composition of the DMC-MeOH azeotrope, this will reduce the equipment cost and operating cost required for the extractive distillation system to separate the DMC and MeOH mixture. The architecture proposed by the present invention can greatly reduce the energy consumption and production cost of the entire manufacturing process of HDC.

此外，可進行步驟S104，使第一塔底液體產物進入蒸餾塔124中，而產生第二塔頂液體產物與第二塔底液體產物。第二塔頂液體產物可包括DMC，且更可包括微量的MeOH。第二塔底液體產物可包括HDC，且更可包括微量的HDA、微量的高沸點中間產物(HMC)與微量的高沸點不純物。In addition, step S104 may be performed to make the first bottom liquid product enter the distillation column 124 to generate a second top liquid product and a second bottom liquid product. The second overhead liquid product may include DMC, and may further include traces of MeOH. The second bottom liquid product may include HDC, and may further include trace amounts of HDA, trace amounts of high-boiling intermediate products (HMC), and trace amounts of high-boiling impurities.

另外，可進行步驟S106，使第一塔頂氣體產物經冷凝後所得的第一塔頂液體產物與萃取劑進入萃取蒸餾塔132中，而產生第三塔頂液體產物與第三塔底液體產物。舉例來說，第一塔頂氣體產物可將潛熱釋放給下段塔110的再沸器116而成為塔頂液體產物後或者經冷凝器122冷凝成塔頂液體產物後進入回流槽120，回流槽120內一部份塔頂液體產物可回流至上段塔110，一部份塔頂液體產物收集在回流槽120中，再使塔頂液體產物與萃取劑進入萃取蒸餾塔中。萃取劑可用於萃取蒸餾塔132中的DMC。在萃取蒸餾塔132中所添加的萃取劑例如是苯胺或酚。第三塔頂液體產物可包括MeOH，且更可包括微量的DMC。第三塔底液體產物可包括DMC與萃取劑，且更可包括微量的MeOH。In addition, step S106 may be performed, so that the first overhead liquid product and the extractant obtained after the condensation of the first overhead gas product enter the extractive distillation column 132 to produce the third overhead liquid product and the third overhead liquid product . For example, the first overhead gas product may release latent heat to the reboiler 116 of the lower column 110 to become the overhead liquid product or condensed into the overhead liquid product by the condenser 122 and enter the reflux tank 120, the reflux tank 120 A part of the liquid product at the top of the column can be refluxed to the upper column 110, a part of the liquid product at the top of the column is collected in the reflux tank 120, and then the liquid product at the top of the column and the extractant enter the extractive distillation column. The extractant can be used to extract DMC in the distillation column 132. The extractant added in the extractive distillation column 132 is, for example, aniline or phenol. The third overhead liquid product may include MeOH, and may even include trace amounts of DMC. The bottom liquid product of the third column may include DMC and extractant, and may further include a small amount of MeOH.

接著，可進行步驟S108，使第三塔底液體產物進入萃取劑回收塔144中，而產生第四塔頂液體產物與第四塔底液體產物。第四塔頂液體產物可包括DMC，且更可包括微量的MeOH。第四塔底液體產物可包括萃取劑，且更可包括微量的DMC。Next, step S108 may be performed to make the third bottom liquid product enter the extractant recovery column 144 to produce a fourth top liquid product and a fourth bottom liquid product. The fourth overhead liquid product may include DMC, and may further include traces of MeOH. The fourth bottom liquid product may include an extractant, and may further include a trace amount of DMC.

另一方面，可將蒸餾塔124的第二塔底液體產物作為連接至萃取蒸餾塔132的塔底的再沸器136、連接至萃取劑回收塔144的塔底的再沸器146與連接在上段塔110與萃取蒸餾塔132之間的熱交換器134中的至少一者的熱源，且藉由進行上述熱整合可更進一步地降低能耗與生產成本。此外，可將萃取劑回收塔144的第四塔底液體產物作為連接在上段塔110與萃取蒸餾塔132之間的熱交換器154的熱源，且藉由進行上述熱整合可更進一步地降低能耗與生產成本。另外，在圖1中所示出的熱整合的路徑(以虛線表示)僅為舉例說明，本發明並不以此為限。所屬技術領域中具有通常知識者可參考上述實施例的教示並根據需求對熱整合的路徑進行調整。On the other hand, the second bottom liquid product of the distillation column 124 can be used as the reboiler 136 connected to the bottom of the extractive distillation column 132, and the reboiler 146 connected to the bottom of the extractant recovery column 144 is connected to The heat source of at least one of the heat exchangers 134 between the upper column 110 and the extractive distillation column 132 can further reduce energy consumption and production costs by performing the above heat integration. In addition, the fourth bottom liquid product of the extractant recovery column 144 can be used as the heat source of the heat exchanger 154 connected between the upper column 110 and the extractive distillation column 132, and the energy can be further reduced by performing the above heat integration Consumption and production costs. In addition, the path of heat integration shown in FIG. 1 (indicated by dotted lines) is only an example, and the present invention is not limited thereto. Those of ordinary skill in the art can refer to the teachings of the above embodiments and adjust the path of thermal integration according to requirements.

基於上述實施例可知，在上述HDC的製造裝置與製造方法中，由於下段塔112是操作在低壓，所以可有效地降低下段塔112的塔底的再沸器能耗，進而大幅度降低在生產HDC時的能耗與生產成本。此外，壓縮機114可提高上段塔110中的壓力，藉此可降低上段塔110中的DMC的含量，並可同時提高下段塔112中的DMC的含量，且可提高上段塔110的塔頂氣體產物溫度，而作為再沸器的熱源，進而降低在生產HDC時的能耗與生產成本。Based on the above embodiment, it can be seen that in the above HDC manufacturing apparatus and manufacturing method, since the lower column 112 is operated at a low pressure, the energy consumption of the reboiler at the bottom of the lower column 112 can be effectively reduced, thereby greatly reducing the production HDC energy consumption and production costs. In addition, the compressor 114 can increase the pressure in the upper column 110, thereby reducing the content of DMC in the upper column 110, and can simultaneously increase the content of DMC in the lower column 112, and can increase the top gas of the upper column 110 The product temperature serves as a heat source for the reboiler, which in turn reduces energy consumption and production costs when producing HDC.

綜上所述，在上述實施例的HDC的製造裝置與製造方法中，由於壓縮機連接在下段塔的氣體出口與上段塔的氣體入口之間，因此可藉由壓縮機的作用來大幅度降低在生產HDC時的能耗與生產成本。In summary, in the HDC manufacturing apparatus and manufacturing method of the above embodiment, since the compressor is connected between the gas outlet of the lower tower and the gas inlet of the upper tower, it can be greatly reduced by the action of the compressor Energy consumption and production costs when producing HDC.

雖然本發明已以實施例揭露如上，然其並非用以限定本發明，任何所屬技術領域中具有通常知識者，在不脫離本發明的精神和範圍內，當可作些許的更動與潤飾，故本發明的保護範圍當視後附的申請專利範圍所界定者為準。Although the present invention has been disclosed as above with examples, it is not intended to limit the present invention. Any person with ordinary knowledge in the technical field can make some changes and modifications without departing from the spirit and scope of the present invention. The scope of protection of the present invention shall be subject to the scope defined in the appended patent application.

100:HDC的製造裝置 102:反應器 102a:出料口 104:HDA供應裝置 106:DMC供應裝置 108、124:蒸餾塔 110:上段塔 110a:氣體入口 110b:液體出口 112:下段塔 112a:氣體出口 112b:液體入口 114:壓縮機 115:洩壓閥 116、118、126、136、138、146、148:再沸器 120、128、140、150:回流槽 122、130、142、152、156:冷凝器 132:萃取蒸餾塔 134、154:熱交換器 144:萃取劑回收塔 S100、S102、S104、S106、S108:步驟100: HDC manufacturing device 102: Reactor 102a: Outlet 104: HDA supply device 106: DMC supply device 108, 124: distillation tower 110: Upper tower 110a: gas inlet 110b: Liquid outlet 112: Lower tower 112a: gas outlet 112b: Liquid inlet 114: Compressor 115: Pressure relief valve 116, 118, 126, 136, 138, 146, 148: reboiler 120, 128, 140, 150: reflux tank 122, 130, 142, 152, 156: condenser 132: Extractive distillation tower 134, 154: heat exchanger 144: Extractant recovery tower S100, S102, S104, S106, S108: steps

圖1為本發明一實施例的HDC的製造裝置的示意圖。 圖2為本發明一實施例的HDC的製造流程圖。FIG. 1 is a schematic diagram of an HDC manufacturing apparatus according to an embodiment of the invention. FIG. 2 is a manufacturing flowchart of an HDC according to an embodiment of the invention.

100:HDC的製造裝置 100: HDC manufacturing device

102:反應器 102: Reactor

102a:出料口 102a: Outlet

104:HDA供應裝置 104: HDA supply device

106:DMC供應裝置 106: DMC supply device

108、124:蒸餾塔 108, 124: distillation tower

110:上段塔 110: Upper tower

110a:氣體入口 110a: gas inlet

110b:液體出口 110b: Liquid outlet

112:下段塔 112: Lower tower

112a:氣體出口 112a: gas outlet

112b:液體入口 112b: Liquid inlet

114:壓縮機 114: Compressor

115:洩壓閥 115: Pressure relief valve

116、118、126、136、138、146、148:再沸器 116, 118, 126, 136, 138, 146, 148: reboiler

120、128、140、150:回流槽 120, 128, 140, 150: reflux tank

122、130、142、152、156:冷凝器 122, 130, 142, 152, 156: condenser

132:萃取蒸餾塔 132: Extractive distillation tower

134、154:熱交換器 134, 154: heat exchanger

144:萃取劑回收塔 144: Extractant recovery tower

Claims (30)

一種六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，包括： 反應器； 1,6-己二胺供應裝置，連接至所述反應器； 碳酸二甲酯供應裝置，連接至所述反應器；以及 第一蒸餾塔，連接至所述反應器的出料口，且包括： 上段塔； 下段塔；以及 壓縮機，連接在所述下段塔的氣體出口與所述上段塔的氣體入口之間。A manufacturing device of methyl hexamethylene-1,6-dicarbamate includes: a reactor; a 1,6-hexanediamine supply device connected to the reactor; a dimethyl carbonate supply device connected to The reactor; and a first distillation column connected to the outlet of the reactor, and including: an upper column; a lower column; and a compressor, connected to the gas outlet of the lower column and the upper column Between gas inlets. 如申請專利範圍第1項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，其中在所述反應器中具有觸媒。The manufacturing apparatus for methyl hexamethylene-1,6-dicarbamate as described in item 1 of the patent application scope, wherein a catalyst is provided in the reactor. 如申請專利範圍第1項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，其中所述上段塔的液體出口連接至所述下段塔的液體入口。The manufacturing apparatus of methyl hexamethylene-1,6-dicarbamate as described in item 1 of the patent application scope, wherein the liquid outlet of the upper column is connected to the liquid inlet of the lower column. 如申請專利範圍第1項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，其中所述上段塔的塔頂氣體產物溫度高於所述下段塔的塔底液體產物溫度。The manufacturing device of methyl hexamethylene-1,6-dicarbamate as described in item 1 of the patent application scope, wherein the temperature of the gas product at the top of the upper column is higher than the liquid product at the bottom of the lower column temperature. 如申請專利範圍第1項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，所述上段塔的塔頂氣體產物溫度比所述下段塔的塔底液體產物溫度高5°C以上。According to the manufacturing device of methyl hexamethylene-1,6-dicarbamate described in item 1 of the patent application scope, the temperature of the gas product at the top of the upper column is higher than the temperature of the liquid product at the bottom of the lower column Above 5°C. 如申請專利範圍第1項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，其中所述上段塔中的壓力大於所述下段塔中的壓力。The manufacturing device of methylhexamethylene-1,6-dicarbamate as described in item 1 of the scope of the patent application, wherein the pressure in the upper column is greater than the pressure in the lower column. 如申請專利範圍第1項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，更包括： 第一再沸器，連接至所述下段塔的塔底，其中將所述上段塔的塔頂氣體產物作為所述第一再沸器的熱源。The manufacturing device for methyl hexamethylene-1,6-dicarbamate as described in item 1 of the scope of the patent application further includes: a first reboiler connected to the bottom of the lower column, wherein the The top gas product of the upper column serves as the heat source of the first reboiler. 如申請專利範圍第7項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，更包括： 第二再沸器，連接至所述下段塔的塔底。The manufacturing device for methyl hexamethylene-1,6-dicarbamate as described in item 7 of the scope of the patent application further includes: a second reboiler connected to the bottom of the lower column. 如申請專利範圍第1項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，更包括： 第二蒸餾塔，連接至所述下段塔的塔底。The manufacturing apparatus for methyl hexamethylene-1,6-dicarbamate as described in item 1 of the scope of the patent application further includes: a second distillation column connected to the bottom of the lower column. 如申請專利範圍第9項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，更包括： 萃取蒸餾塔，連接至所述上段塔的塔頂。The manufacturing apparatus for methyl hexamethylene-1,6-dicarbamate as described in item 9 of the scope of the patent application further includes: an extractive distillation column connected to the top of the upper column. 如申請專利範圍第10項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，更包括： 萃取劑回收塔，連接至所述萃取蒸餾塔的塔底。The manufacturing apparatus for methyl hexamethylene-1,6-dicarbamate as described in item 10 of the scope of the patent application further includes: an extractant recovery tower connected to the bottom of the extractive distillation tower. 如申請專利範圍第11項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，其中將所述第二蒸餾塔的塔底液體產物作為連接至所述萃取蒸餾塔的塔底的再沸器、連接至所述萃取劑回收塔的塔底的再沸器與連接在所述上段塔與所述萃取蒸餾塔之間的熱交換器中的至少一者的熱源。The manufacturing apparatus of methyl hexamethylene-1,6-dicarbamate as described in item 11 of the patent application scope, wherein the bottom liquid product of the second distillation column is connected to the extractive distillation column A heat source of at least one of a reboiler at the bottom of the column, a reboiler connected to the bottom of the extractant recovery column, and a heat exchanger connected between the upper column and the extractive distillation column. 如申請專利範圍第11項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造裝置，其中將所述萃取劑回收塔的塔底液體產物作為連接在所述上段塔與所述萃取蒸餾塔之間的熱交換器的熱源。The manufacturing apparatus for methyl hexamethylene-1,6-dicarbamate as described in item 11 of the patent application scope, wherein the bottom liquid product of the extractant recovery column is connected as the upper column and the The heat source of the heat exchanger between the extractive distillation towers. 一種六亞甲基-1,6-二氨基甲酸甲酯的製造方法，包括： 在反應器中，使1,6-己二胺與碳酸二甲酯在存在觸媒的環境下進行反應，而產生反應後之產物；以及 使所述反應後之產物進入第一蒸餾塔中，而產生第一塔頂氣體產物與第一塔底液體產物，其中所述第一蒸餾塔包括： 上段塔，其中由所述上段塔產生所述第一塔頂氣體產物； 下段塔，其中由所述下段塔產生所述第一塔底液體產物；以及 壓縮機，連接在所述下段塔的氣體出口與所述上段塔的氣體入口之間。A method for manufacturing methyl hexamethylene-1,6-dicarbamate includes: in a reactor, reacting 1,6-hexanediamine and dimethyl carbonate in the presence of a catalyst, and Producing a product after the reaction; and causing the product after the reaction to enter the first distillation column to produce the first gas product at the top of the column and the liquid product at the bottom of the first column, wherein the first distillation column includes: an upper column, wherein The first column top gas product is produced from the upper column; the lower column column, wherein the first column bottom liquid product is produced from the lower column; and the compressor, which is connected to the gas outlet of the lower column and the Between the gas inlets of the upper tower. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中所述上段塔的液體出口連接至所述下段塔的液體入口。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 14 of the patent application scope, wherein the liquid outlet of the upper column is connected to the liquid inlet of the lower column. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中所述上段塔的塔頂氣體產物溫度高於所述下段塔的塔底液體產物溫度。The method for producing methyl hexamethylene-1,6-dicarbamate as described in item 14 of the patent application scope, wherein the temperature of the gas product at the top of the upper column is higher than the liquid product at the bottom of the lower column temperature. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，所述上段塔的塔頂氣體產物溫度比所述下段塔的塔底液體產物溫度高5°C以上。According to the method for manufacturing methyl hexamethylene-1,6-dicarbamate described in item 14 of the patent application scope, the temperature of the gas product at the top of the upper column is higher than the temperature of the liquid product at the bottom of the lower column Above 5°C. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中所述上段塔中的壓力大於所述下段塔中的壓力。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 14 of the patent application scope, wherein the pressure in the upper column is greater than the pressure in the lower column. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中在所述1,6-己二胺與所述碳酸二甲酯的反應中，使用過量的所述碳酸二甲酯作為反應物。The method for producing methyl hexamethylene-1,6-dicarbamate as described in item 14 of the patent application scope, wherein in the reaction of the 1,6-hexanediamine with the dimethyl carbonate, An excess of the dimethyl carbonate was used as a reactant. 如申請專利範圍第19項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中在所述1,6-己二胺與所述碳酸二甲酯的反應中，所述碳酸二甲酯與所述1,6-己二胺的進料莫耳比值為3至9。The method for producing methyl hexamethylene-1,6-dicarbamate as described in item 19 of the patent application scope, wherein in the reaction of the 1,6-hexanediamine with the dimethyl carbonate, The feed molar ratio of the dimethyl carbonate to the 1,6-hexanediamine is 3 to 9. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中所述反應後之產物包括六亞甲基-1,6-二氨基甲酸甲酯、甲醇與所述碳酸二甲酯，所述第一塔頂氣體產物包括所述甲醇與所述碳酸二甲酯，且所述第一塔底液體產物包括所述六亞甲基-1,6-二氨基甲酸甲酯與所述碳酸二甲酯。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 14 of the patent application scope, wherein the product after the reaction includes methyl hexamethylene-1,6-dicarbamate , Methanol and the dimethyl carbonate, the first overhead gas product includes the methanol and the dimethyl carbonate, and the first bottom liquid product includes the hexamethylene-1,6 -Methyl dicarbamate and the dimethyl carbonate. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中將所述上段塔的所述第一塔頂氣體產物作為連接至所述下段塔的塔底的再沸器的熱源。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 14 of the scope of patent application, wherein the first overhead gas product of the upper column is connected to the lower column The heat source of the reboiler at the bottom of the tower. 如申請專利範圍第14項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，更包括： 使所述第一塔底液體產物進入第二蒸餾塔中，而產生第二塔頂液體產物與第二塔底液體產物。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 14 of the scope of the patent application further includes: causing the liquid product at the bottom of the first column to enter the second distillation column to produce the first The liquid product at the top of the second column and the liquid product at the bottom of the second column. 如申請專利範圍第23項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中所述第二塔頂液體產物包括所述碳酸二甲酯，且所述第二塔底液體產物包括六亞甲基-1,6-二氨基甲酸甲酯。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 23 of the patent application scope, wherein the second overhead liquid product includes the dimethyl carbonate, and the second The bottom liquid product includes methyl hexamethylene-1,6-dicarbamate. 如申請專利範圍第23項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，更包括： 使所述第一塔頂氣體產物經冷凝後所得的第一塔頂液體產物與萃取劑進入萃取蒸餾塔中，而產生第三塔頂液體產物與第三塔底液體產物。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 23 of the scope of the patent application further includes: a first overhead liquid obtained by condensing the first overhead gas product The product and extractant enter the extractive distillation column to produce a third overhead liquid product and a third overhead liquid product. 如申請專利範圍第25項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中所述第三塔頂液體產物包括甲醇，且所述第三塔底液體產物包括所述碳酸二甲酯與所述萃取劑。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 25 of the patent application scope, wherein the third overhead liquid product includes methanol, and the third bottom liquid product includes The dimethyl carbonate and the extractant. 如申請專利範圍第25項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，更包括： 使所述第三塔底液體產物進入萃取劑回收塔中，而產生第四塔頂液體產物與第四塔底液體產物。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 25 of the scope of the patent application further includes: causing the liquid product at the bottom of the third column to enter the extractant recovery column, and producing the first The liquid product at the top of the fourth column and the liquid product at the bottom of the fourth column. 如申請專利範圍第27項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中所述第四塔頂液體產物包括所述碳酸二甲酯，且所述第四塔底液體產物包括所述萃取劑。The method for manufacturing methyl hexamethylene-1,6-dicarbamate as described in item 27 of the patent application scope, wherein the fourth overhead liquid product includes the dimethyl carbonate, and the fourth The bottom liquid product includes the extractant. 如申請專利範圍第27項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中將所述第二蒸餾塔的所述第二塔底液體產物作為連接至所述萃取蒸餾塔的塔底的再沸器、連接至所述萃取劑回收塔的塔底的再沸器與連接在所述上段塔與所述萃取蒸餾塔之間的熱交換器中的至少一者的熱源。The method for producing methyl hexamethylene-1,6-dicarbamate as described in item 27 of the patent application scope, wherein the second bottom liquid product of the second distillation column is connected to the At least one of a reboiler at the bottom of the extractive distillation column, a reboiler connected to the bottom of the extractant recovery column, and a heat exchanger connected between the upper column and the extractive distillation column Heat source. 如申請專利範圍第27項所述的六亞甲基-1,6-二氨基甲酸甲酯的製造方法，其中將所述萃取劑回收塔的所述第四塔底液體產物作為連接在所述上段塔與所述萃取蒸餾塔之間的熱交換器的熱源。The method for producing methyl hexamethylene-1,6-dicarbamate as described in Item 27 of the patent application scope, wherein the fourth bottom liquid product of the extractant recovery column is connected to the The heat source of the heat exchanger between the upper column and the extractive distillation column.
TW107135353A 2018-10-08 2018-10-08 Apparatus and method for manufacturing dimethylhexane-1,6-dicarbamate TWI686377B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
TW107135353A TWI686377B (en) 2018-10-08 2018-10-08 Apparatus and method for manufacturing dimethylhexane-1,6-dicarbamate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
TW107135353A TWI686377B (en) 2018-10-08 2018-10-08 Apparatus and method for manufacturing dimethylhexane-1,6-dicarbamate

Publications (2)

Publication Number Publication Date
TWI686377B true TWI686377B (en) 2020-03-01
TW202014404A TW202014404A (en) 2020-04-16

Family

ID=70767101

Family Applications (1)

Application Number Title Priority Date Filing Date
TW107135353A TWI686377B (en) 2018-10-08 2018-10-08 Apparatus and method for manufacturing dimethylhexane-1,6-dicarbamate

Country Status (1)

Country Link
TW (1) TWI686377B (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102971287A (en) * 2010-06-16 2013-03-13 三井化学株式会社 Carbamate production method, isocyanate production method, carbamate production device and isocyanate production device
CN103936625A (en) * 2014-05-08 2014-07-23 南京工业大学 Method for synthesizing hexamethylene-1, 6-diamino methyl formate
CN107417573A (en) * 2016-05-24 2017-12-01 中国石油化学工业开发股份有限公司 Method for preparing carbamate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102971287A (en) * 2010-06-16 2013-03-13 三井化学株式会社 Carbamate production method, isocyanate production method, carbamate production device and isocyanate production device
CN103936625A (en) * 2014-05-08 2014-07-23 南京工业大学 Method for synthesizing hexamethylene-1, 6-diamino methyl formate
CN107417573A (en) * 2016-05-24 2017-12-01 中国石油化学工业开发股份有限公司 Method for preparing carbamate

Also Published As

Publication number Publication date
TW202014404A (en) 2020-04-16

Similar Documents

Publication Publication Date Title
CN102498093B (en) Method for producing isocyanates
WO2021078239A1 (en) Gas-liquid bubbling bed reactor, reaction system and method for synthesizing carbonate
CN104761429B (en) A kind of method for producing dimethyl carbonate and ethylene glycol
US20030032844A1 (en) Method of manufacturing methanol
CN103130611B (en) Neopentyl glycol condensation hydrogenation production technique and device thereof
CN108101742B (en) Method for reforming methanol process
TWI421125B (en) Reactor reaction speed control method, reaction device and dimethyl ether manufacturing method
KR102533952B1 (en) Apparatus and method of preparing propylene glycol methyl ether acetate
CN110218151B (en) Device and method for preparing propyl propionate through tower kettle flash evaporation type heat pump reaction rectification
JP2016029039A (en) Method and device for circulation processing and purification of propylene
US6486218B2 (en) Method of manufacturing methanol
TWI686377B (en) Apparatus and method for manufacturing dimethylhexane-1,6-dicarbamate
US12017978B2 (en) Method for preparing isopropyl alcohol
CN111004151B (en) Device and method for producing hexamethylene-1, 6-dicarbamate
CN115417768B (en) Energy coupling process for preparing dimethyl carbonate by methanol liquid phase oxidation carbonylation
CN107848960A (en) Method for preparing isocyanates
CN105008327B (en) Urea equipment remodeling method
US20150232402A1 (en) Method for producing dimethyl ether and device suitable therefor
US8129565B2 (en) High-pressure loop in a process for synthesis of urea
US20200277254A1 (en) Multistep process for the preparation of hexamethylene diisocyanate, pentamethylene diisocyanate or toluene diisocyanate
TWI745931B (en) Apparatus and method for manufacturing dimethyl carbonate
CN111574336A (en) Synthetic reaction process of ethylene glycol mono-tert-butyl ether
CN212347756U (en) Methyl phenyl carbonate reaction rectifying tower device
US20240174585A1 (en) Method for preparing isopropyl alcohol
US11820731B2 (en) Systems and methods for producing methanol with recycling of fusel oil