TWI642660B - Manufacturing methods and manufacturing apparatuses of propylene carbonate and dimethyl carbonate - Google Patents
Manufacturing methods and manufacturing apparatuses of propylene carbonate and dimethyl carbonate Download PDFInfo
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Abstract
本發明提供碳酸丙烯酯與碳酸二甲酯的製造方法與製造裝置。碳酸丙烯酯的製造方法包括下列步驟。使尿素與過量的丙二醇分別進入蒸餾系統的第一部分，以使尿素與丙二醇在第一部分中進行反應與分離而形成包括氨氣的第一產物與包括丙二醇及碳酸丙烯酯的第二產物。使第二產物進入蒸餾系統的第二部分，以使第二產物分離而形成包括丙二醇的第三產物與包括碳酸丙烯酯的第四產物。第一部分與第二部分為互相連接的兩個蒸餾塔。The invention provides a method and a device for producing propylene carbonate and dimethyl carbonate. The method for producing propylene carbonate includes the following steps. Urea and excess propylene glycol are respectively entered into the first part of the distillation system, so that urea and propylene glycol are reacted and separated in the first part to form a first product including ammonia and a second product including propylene glycol and propylene carbonate. The second product is passed into the second part of the distillation system to separate the second product to form a third product including propylene glycol and a fourth product including propylene carbonate. The first part and the second part are two distillation columns connected to each other.
Description
本發明是有關於一種碳酸丙烯酯與碳酸二甲酯的製造方法與製造裝置，且特別是有關於一種以尿素間接醇解法製造碳酸丙烯酯與碳酸二甲酯的方法與裝置。The present invention relates to a method and device for manufacturing propylene carbonate and dimethyl carbonate, and more particularly, to a method and device for manufacturing propylene carbonate and dimethyl carbonate by urea indirect alcoholysis.
碳酸二甲酯（dimethyl carbonate；DMC）是一種低毒性、低污染、對環境友好的基礎化工原料。碳酸二甲酯可進行羰基化、甲基化、甲酯化以及酯交換等反應，而生成許多重要的化工產品。另一方面，以碳酸二甲酯為原料可以開發與製備多種高附加價值的精密化學品，而在醫藥、農業、染料、潤滑油添加劑、食品增香劑與電子化學品等領域獲得廣泛的應用。如此一來，如何以低製造成本以及高轉化率的方法及裝置製造碳酸二甲酯成為本領域重要的課題之一。Dimethyl carbonate (DMC) is a basic chemical raw material with low toxicity, low pollution and environmental friendliness. Dimethyl carbonate can be subjected to carbonylation, methylation, methylation, and transesterification to generate many important chemical products. On the other hand, dimethyl carbonate can be used as a raw material to develop and prepare a variety of high-value-added precision chemicals, and has been widely used in medicine, agriculture, dyes, lubricant additives, food flavoring agents, and electronic chemicals. . In this way, how to manufacture dimethyl carbonate with a method and a device with low manufacturing cost and high conversion rate has become one of the important topics in the field.
本發明提供一種碳酸丙烯酯的製造方法與一種碳酸丙烯酯的製造裝置，具有較高的產物轉化率與較低的製造成本。The invention provides a method for manufacturing propylene carbonate and a device for manufacturing propylene carbonate, which have higher product conversion rate and lower manufacturing cost.
本發明提供一種碳酸二甲酯的製造方法與一種碳酸二甲酯的製造裝置，具有較高的產物轉化率與較低的製造成本。The invention provides a method for manufacturing dimethyl carbonate and a device for manufacturing dimethyl carbonate, which have higher product conversion rate and lower manufacturing cost.
本發明的碳酸丙烯酯的製造方法包括下列步驟。使尿素與過量丙二醇分別進入蒸餾系統的第一部分，以使尿素與丙二醇在第一部分中進行反應與分離而形成包括氨氣的第一產物與包括丙二醇及碳酸丙烯酯的第二產物。使第二產物進入蒸餾系統的第二部分，以使第二產物分離而形成包括丙二醇的第三產物與包括碳酸丙烯酯的第四產物。第一部分與第二部分為互相連接的兩個蒸餾塔。The method for producing propylene carbonate of the present invention includes the following steps. Urea and excess propylene glycol are respectively entered into the first part of the distillation system, so that urea and propylene glycol are reacted and separated in the first part to form a first product including ammonia and a second product including propylene glycol and propylene carbonate. The second product is passed into the second part of the distillation system to separate the second product to form a third product including propylene glycol and a fourth product including propylene carbonate. The first part and the second part are two distillation columns connected to each other.
在本發明的一實施例中，上述的第一部分為第一反應蒸餾塔且第二部分為第一蒸餾塔。第一產物以及第二產物分別為反應蒸餾塔的塔頂產物與塔底產物。第三產物與第四產物分別為第一蒸餾塔的塔頂產物與塔底產物。In an embodiment of the present invention, the first part is a first reactive distillation column and the second part is a first distillation column. The first product and the second product are the top product and the bottom product of the reactive distillation column, respectively. The third product and the fourth product are the top product and the bottom product of the first distillation column, respectively.
在本發明的一實施例中，上述的碳酸丙烯酯的製造方法更包括使第一反應蒸餾塔的塔底液體與第一蒸餾塔的塔頂氣體在第一熱交換裝置中進行熱交換後，分別回流至第一反應蒸餾塔的塔底與第一蒸餾塔的塔頂。In an embodiment of the present invention, the method for manufacturing propylene carbonate further includes heat-exchanging the bottom liquid of the first reactive distillation column and the top gas of the first distillation column in a first heat exchange device. Reflux to the bottom of the first reactive distillation column and the top of the first distillation column, respectively.
在本發明的一實施例中，上述的第一蒸餾塔可包括上段塔、下段塔以及氣體壓縮裝置，以使下段塔的塔頂氣體進入氣體壓縮裝置以產生壓縮產物，且使壓縮產物進入上段塔而產生上段塔的塔頂產物。上段塔的塔頂產物即為第一蒸餾塔的塔頂產物。In an embodiment of the present invention, the first distillation column may include an upper stage column, a lower stage column, and a gas compression device, so that the top gas of the lower stage column enters the gas compression device to generate a compression product, and the compression product enters the upper stage. The tower produces the top product of the upper tower. The top product of the upper column is the top product of the first distillation column.
在本發明的一實施例中，上述的第一反應蒸餾塔的塔底液體與上述的上段塔的塔頂氣體可在第一熱交換裝置中進行熱交換後，分別回流至第一反應蒸餾塔的塔底與第一蒸餾塔的上段塔的塔頂。In an embodiment of the present invention, the bottom liquid of the first reactive distillation column and the top gas of the upper column may be heat-exchanged in the first heat exchange device and then refluxed to the first reactive distillation column, respectively. The bottom of the column and the top of the upper column of the first distillation column.
在本發明的一實施例中，上述的上段塔的塔頂中的部分氣體與上述的下段塔的塔底液體在第二熱交換裝置中進行熱交換後，分別回流至上段塔的塔頂與下段塔的塔底。In an embodiment of the present invention, a part of the gas in the top of the upper tower and the bottom liquid in the lower tower are heat-exchanged in the second heat exchange device, and then return to the top of the upper tower and the tower respectively. The bottom of the lower tower.
本發明的碳酸二甲酯的製造方法包括下列步驟。使過量甲醇以及上述的第四產物進入第二反應蒸餾塔，以使甲醇與第四產物中的碳酸丙烯酯在第二反應蒸餾塔中進行反應與分離，而在第二反應蒸餾塔的頂部形成包括甲醇與碳酸二甲酯的第五產物。使第五產物以及萃取劑進入第二蒸餾塔，以在第二蒸餾塔的頂部與底部分別形成包括甲醇的第六產物與包括碳酸二甲酯的第七產物。The method for producing dimethyl carbonate of the present invention includes the following steps. Excess methanol and the fourth product mentioned above are passed into the second reactive distillation column, so that methanol and propylene carbonate in the fourth product are reacted and separated in the second reactive distillation column, and formed on the top of the second reactive distillation column A fifth product including methanol and dimethyl carbonate. The fifth product and the extractant are passed into a second distillation column to form a sixth product including methanol and a seventh product including dimethyl carbonate at the top and bottom of the second distillation column, respectively.
在本發明的一實施例中，上述的第七產物更包括萃取劑，且碳酸二甲酯的製造方法更包括使第七產物進入第三蒸餾塔，以使第七產物中的碳酸二甲酯與萃取劑在第三蒸餾塔中分離而形成包括碳酸二甲酯的第八產物與包括萃取劑的第九產物。In an embodiment of the present invention, the seventh product further includes an extractant, and the method for manufacturing dimethyl carbonate further includes passing the seventh product into a third distillation column to make the dimethyl carbonate in the seventh product It is separated from the extractant in a third distillation column to form an eighth product including dimethyl carbonate and a ninth product including an extractant.
本發明的碳酸丙烯酯的製造裝置包括蒸餾系統。蒸餾系統具有第一部分與第二部分。第一部分與第二部分為互相連接的兩個蒸餾塔。尿素與過量丙二醇在第一部分中進行反應與分離而形成包括氨氣的第一產物以及包括丙二醇與碳酸丙烯酯的第二產物。第二產物中的丙二醇與碳酸丙烯酯進入第二部分而分離以形成包括丙二醇的第三產物以及包括碳酸丙烯酯的第四產物。The apparatus for producing propylene carbonate of the present invention includes a distillation system. The distillation system has a first part and a second part. The first part and the second part are two distillation columns connected to each other. Urea and excess propylene glycol are reacted and separated in the first part to form a first product including ammonia and a second product including propylene glycol and propylene carbonate. Propylene glycol and propylene carbonate in the second product enter the second part and are separated to form a third product including propylene glycol and a fourth product including propylene carbonate.
在本發明的一實施例中，上述的第一部分為第一反應蒸餾塔且第二部分為第一蒸餾塔。第一產物以及第二產物分別為反應蒸餾塔的塔頂產物與塔底產物。第三產物與第四產物分別為第一蒸餾塔的塔頂產物與塔底產物。In an embodiment of the present invention, the first part is a first reactive distillation column and the second part is a first distillation column. The first product and the second product are the top product and the bottom product of the reactive distillation column, respectively. The third product and the fourth product are the top product and the bottom product of the first distillation column, respectively.
在本發明的一實施例中，上述的碳酸丙烯酯的製造裝置更包括第一熱交換裝置。第一熱交換裝置連接於第一反應蒸餾塔與第一蒸餾塔之間，以使第一反應蒸餾塔的塔底液體與第一蒸餾塔的塔頂氣體在第一熱交換裝置中進行熱交換後，分別回流至第一反應蒸餾塔的塔底與第一蒸餾塔的塔頂。In an embodiment of the present invention, the above-mentioned propylene carbonate manufacturing apparatus further includes a first heat exchange apparatus. The first heat exchange device is connected between the first reactive distillation column and the first distillation column, so that the bottom liquid of the first reactive distillation column and the top gas of the first distillation column perform heat exchange in the first heat exchange device. After that, it was refluxed to the bottom of the first reactive distillation column and the top of the first distillation column, respectively.
在本發明的一實施例中，上述的第一蒸餾塔可包括上段塔、下段塔以及氣體壓縮裝置。氣體壓縮裝置連接於上段塔與下段塔之間，以使下段塔的塔頂氣體進入氣體壓縮裝置以產生壓縮產物，且使壓縮產物進入上段塔的塔底而產生上段塔的塔頂產物。上段塔的塔頂產物即為第一蒸餾塔的塔頂產物。In an embodiment of the present invention, the first distillation column may include an upper column, a lower column, and a gas compression device. The gas compression device is connected between the upper stage tower and the lower stage tower, so that the top gas of the lower stage tower enters the gas compression unit to generate a compression product, and the compressed product enters the bottom of the upper stage tower to generate the top stage product of the upper stage tower. The top product of the upper column is the top product of the first distillation column.
在本發明的一實施例中，上述的第一反應蒸餾塔的塔底液體與上述的上段塔的塔頂氣體可在第一熱交換裝置中進行熱交換後，分別回流至第一反應蒸餾塔的塔底與第一蒸餾塔的上段塔的塔頂。In an embodiment of the present invention, the bottom liquid of the first reactive distillation column and the top gas of the upper column may be heat-exchanged in the first heat exchange device and then refluxed to the first reactive distillation column, respectively. The bottom of the column and the top of the upper column of the first distillation column.
在本發明的一實施例中，上述的碳酸丙烯酯的製造裝置更可包括第二熱交換裝置。上段塔的塔頂中的部分氣體與下段塔的塔底液體在第二熱交換裝置中進行熱交換後，分別回流至上段塔的塔頂與下段塔的塔底。In an embodiment of the present invention, the above-mentioned propylene carbonate manufacturing apparatus may further include a second heat exchange apparatus. Part of the gas in the top of the upper tower and the liquid in the bottom of the lower tower undergo heat exchange in the second heat exchange device, and then return to the top of the upper tower and the bottom of the lower tower, respectively.
本發明的碳酸二甲酯的製造裝置包括上述的蒸餾系統、第二反應蒸餾塔以及第二蒸餾塔。甲醇以及上述的第四產物中的碳酸丙烯酯在第二反應蒸餾塔中進行反應與分離，而在第二反應蒸餾塔的頂部形成包括甲醇與碳酸二甲酯的第五產物。第五產物與萃取劑在第二蒸餾塔中分離而形成包括甲醇的第六產物以及包括碳酸二甲酯的第七產物。The dimethyl carbonate production apparatus of the present invention includes the above-mentioned distillation system, a second reactive distillation column, and a second distillation column. The methanol and propylene carbonate in the fourth product described above are reacted and separated in a second reactive distillation column, and a fifth product including methanol and dimethyl carbonate is formed on the top of the second reactive distillation column. The fifth product is separated from the extractant in a second distillation column to form a sixth product including methanol and a seventh product including dimethyl carbonate.
在本發明的一實施例中，上述的第七產物更包括所述萃取劑，且碳酸二甲酯的製造裝置更包括第三蒸餾塔。第七產物中的碳酸二甲酯與萃取劑在第三蒸餾塔中分離而形成包括碳酸二甲酯的第八產物與包括所述萃取劑的第九產物。In an embodiment of the present invention, the seventh product further includes the extractant, and the dimethyl carbonate manufacturing apparatus further includes a third distillation column. The dimethyl carbonate in the seventh product is separated from the extractant in the third distillation column to form an eighth product including the dimethyl carbonate and a ninth product including the extractant.
基於上述，尿素與過量丙二醇分別進入碳酸丙烯酯的製造裝置的蒸餾系統，以進行反應而產生碳酸丙烯酯。除此之外，丙二醇與作為產物的碳酸丙烯酯更可在蒸餾系統中分離。因此，可提高作為產物的碳酸丙烯酯的純度，且可提高碳酸丙烯酯的轉化率。如此一來，以較高純度的碳酸丙烯酯作為反應物來製造碳酸二甲酯的方法及裝置亦可具有較高的產物轉化率。Based on the above, urea and excess propylene glycol respectively enter a distillation system of a propylene carbonate production device to perform a reaction to produce propylene carbonate. In addition, propylene glycol can be separated from propylene carbonate as a product in a distillation system. Therefore, the purity of propylene carbonate as a product can be improved, and the conversion rate of propylene carbonate can be improved. In this way, the method and device for producing dimethyl carbonate by using propylene carbonate of higher purity as a reactant can also have a higher product conversion rate.
在一些實施例中，碳酸丙烯酯的蒸餾系統可包括兩個相互連接的第一反應蒸餾塔與第一蒸餾塔。此外，可藉由設置連接於第一反應蒸餾塔與第一蒸餾塔之間的第一熱交換裝置，而可利用第一蒸餾塔的塔頂的熱能來加熱第一反應蒸餾塔的塔底，故可降第一反應蒸餾塔所需的能耗。In some embodiments, the propylene carbonate distillation system may include two first reactive distillation columns and a first distillation column that are interconnected. In addition, by setting a first heat exchange device connected between the first reactive distillation column and the first distillation column, the thermal energy at the top of the first distillation column can be used to heat the bottom of the first reactive distillation column. Therefore, the energy consumption required for the first reactive distillation column can be reduced.
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 features and advantages of the present invention more comprehensible, embodiments are hereinafter described in detail with reference to the accompanying drawings.
圖1A是依照本發明第一實施例的一種碳酸丙烯酯與碳酸二甲酯的製造方法的流程圖。圖1B是依照本發明第一實施例的一種碳酸丙烯酯與碳酸二甲酯的製造裝置的示意圖。FIG. 1A is a flowchart of a method for manufacturing propylene carbonate and dimethyl carbonate according to a first embodiment of the present invention. FIG. 1B is a schematic diagram of an apparatus for manufacturing propylene carbonate and dimethyl carbonate according to the first embodiment of the present invention.
碳酸二甲酯的製造方法包括先製造碳酸丙烯酯，且接著以此碳酸丙烯酯製造碳酸二甲酯。換言之，碳酸二甲酯的製造方法包括碳酸丙烯酯的製造方法。相似地，碳酸二甲酯的製造裝置包括碳酸丙烯酯的製造裝置。A method for producing dimethyl carbonate includes first producing propylene carbonate, and then producing dimethyl carbonate from the propylene carbonate. In other words, the method for producing dimethyl carbonate includes a method for producing propylene carbonate. Similarly, the production apparatus of dimethyl carbonate includes a production apparatus of propylene carbonate.
本實施例的碳酸丙烯酯的製造方法是藉由如圖1B所示的碳酸丙烯酯的製造裝置10進行下列步驟S100至步驟S104。In the method for producing propylene carbonate of this embodiment, the following steps S100 to S104 are performed by the propylene carbonate production apparatus 10 shown in FIG. 1B.
請參照圖1A與圖1B，進行步驟S100，使二氧化碳與氨氣在反應系統100中進行反應以產生尿素。除此之外，二氧化碳與氨氣的反應產物更可包括水。產物的水可由出口101排出。Referring to FIG. 1A and FIG. 1B, step S100 is performed to make carbon dioxide and ammonia react in the reaction system 100 to generate urea. In addition, the reaction product of carbon dioxide and ammonia gas may further include water. The product water can be discharged from the outlet 101.
進行步驟S102，使尿素與過量丙二醇分別進入蒸餾系統102的第一部分102a。蒸餾系統102包括第一部分102a與第二部分102b。在一些實施例中，蒸餾系統102的第一部分102a與第二部分102b分別為第一反應蒸餾塔104與第一蒸餾塔114。第一反應蒸餾塔104與第一蒸餾塔114互相連接。第一反應蒸餾塔104中（例如是圖1B所示的第一反應蒸餾塔104中的斜線區域）可設置有觸媒。舉例而言，觸媒的材料可包括氯化鋅、氧化鋅、氧化鎂、氧化鉛、氧化鈣等金屬氧化物。尿素與丙二醇在第一部分102a（亦即第一反應蒸餾塔104）中進行反應與分離而形成包括氨氣的第一產物與包括丙二醇及碳酸丙烯酯的第二產物。第一產物可為第一反應蒸餾塔104的塔頂產物，且可自第一反應蒸餾塔104的塔頂流至部分冷凝器（partial condenser）106。氨氣可由部份冷凝器106回流至反應系統100中，以循環利用。微量丙二醇與碳酸丙烯酯經部份冷凝器106冷凝成液體後儲存於回流槽108中，且可回流至第一反應蒸餾塔104。第二產物可為第一反應蒸餾塔104的塔底產物，且可進入再沸器110。第二產物於再沸器110中加熱後，可部分回流至第一反應蒸餾塔104中。Step S102 is performed to allow urea and excess propylene glycol to enter the first portion 102a of the distillation system 102, respectively. The distillation system 102 includes a first portion 102a and a second portion 102b. In some embodiments, the first portion 102a and the second portion 102b of the distillation system 102 are a first reactive distillation column 104 and a first distillation column 114, respectively. The first reactive distillation column 104 and the first distillation column 114 are connected to each other. A catalyst may be provided in the first reactive distillation column 104 (for example, a diagonal line region in the first reactive distillation column 104 shown in FIG. 1B). For example, the catalyst material may include metal oxides such as zinc chloride, zinc oxide, magnesium oxide, lead oxide, and calcium oxide. Urea and propylene glycol are reacted and separated in the first part 102a (ie, the first reactive distillation column 104) to form a first product including ammonia gas and a second product including propylene glycol and propylene carbonate. The first product may be an overhead product of the first reactive distillation column 104 and may flow from the overhead of the first reactive distillation column 104 to a partial condenser 106. The ammonia gas can be returned to the reaction system 100 from a part of the condenser 106 for recycling. A small amount of propylene glycol and propylene carbonate are condensed into a liquid by a partial condenser 106 and stored in a reflux tank 108, and can be refluxed to the first reactive distillation column 104. The second product may be a bottom product of the first reactive distillation column 104 and may enter the reboiler 110. After the second product is heated in the reboiler 110, it may be partially refluxed into the first reactive distillation column 104.
進行步驟S104，使部分的第二產物進入蒸餾系統102的第二部分102b。第二產物在第二部分102b（亦即第一蒸餾塔114）中進行分離而形成包括丙二醇的第三產物與包括碳酸丙烯酯的第四產物。在一些實施例中，第三產物為第一蒸餾塔114的塔頂產物，且可自第一蒸餾塔114的塔頂流至冷凝器116。第三產物在冷凝器116中冷凝後可儲存於回流槽118中。回流槽118中冷凝的第三產物可回流至第一蒸餾塔114，且可回流至第一反應蒸餾塔104中，以循環利用。在一些實施例中，部分來自回流槽118的丙二醇可與反應系統100產生的尿素經由相同的進料口進料至第一反應蒸餾塔104，且另一部分的來自回流槽118的丙二醇可經由另一進料口進料至第一反應蒸餾塔104。第四產物為第一蒸餾塔114的塔底產物，且可進入再沸器120。第四產物於再沸器120中加熱後，一部分的第四產物可回流至第一蒸餾塔114中。此外，另一部分的第四產物中的碳酸丙烯酯可作為本實施例的碳酸丙烯酯的製造方法的產物。Step S104 is performed to allow a portion of the second product to enter the second portion 102 b of the distillation system 102. The second product is separated in a second portion 102b (ie, the first distillation column 114) to form a third product including propylene glycol and a fourth product including propylene carbonate. In some embodiments, the third product is an overhead product of the first distillation column 114 and may flow from the overhead of the first distillation column 114 to the condenser 116. The third product may be stored in the reflux tank 118 after being condensed in the condenser 116. The third product condensed in the reflux tank 118 may be refluxed to the first distillation column 114 and may be refluxed to the first reactive distillation column 104 for recycling. In some embodiments, part of the propylene glycol from the reflux tank 118 may be fed to the first reactive distillation column 104 through the same feed port as urea produced by the reaction system 100, and another part of the propylene glycol from the reflux tank 118 may be passed through another A feed port is fed to the first reactive distillation column 104. The fourth product is a bottom product of the first distillation column 114 and may enter the reboiler 120. After the fourth product is heated in the reboiler 120, a part of the fourth product may be refluxed into the first distillation column 114. In addition, the propylene carbonate in the fourth product of the other part can be used as a product of the method for producing propylene carbonate in this embodiment.
丙二醇與碳酸丙烯酯在低壓力（例如是壓力小於0.12 atm）的環境下容易產生共沸物，而難以將兩者分離。因此，在一些實施例中，可提高第一蒸餾塔114的壓力以避免丙二醇與碳酸丙烯酯在第一蒸餾塔114的塔頂形成共沸物。Propylene glycol and propylene carbonate easily generate azeotrope under low pressure (for example, the pressure is less than 0.12 atm), and it is difficult to separate the two. Therefore, in some embodiments, the pressure of the first distillation column 114 may be increased to prevent propylene glycol and propylene carbonate from forming an azeotrope on the top of the first distillation column 114.
本實施例的碳酸二甲酯的製造方法包括上述的步驟S100至步驟S104，且更包括以步驟S104所得到的第四產物接著進行如下所述的步驟S106至步驟S110。The method for manufacturing dimethyl carbonate of this embodiment includes the above-mentioned steps S100 to S104, and further includes a fourth product obtained in step S104, followed by steps S106 to S110 described below.
進行步驟S106，使過量甲醇以及部分的第四產物進入第二反應蒸餾塔124。第二反應蒸餾塔124中（例如是圖1B所示的第二反應蒸餾塔124中的斜線區域）可設置有觸媒。舉例而言，觸媒的材料可包括甲醇鈉（odium methoxide）或有機非離子超强鹼（proazaphosphatrane）等。甲醇與第四產物中的碳酸丙烯酯在第二反應蒸餾塔124中進行反應與分離，而在第二反應蒸餾塔124的頂部形成包括甲醇與碳酸二甲酯的第五產物。第五產物可自第二反應蒸餾塔124的頂部流至冷凝器126。第五產物在冷凝器126中冷凝後可儲存於回流槽128中。回流槽128中冷凝的甲醇與碳酸二甲酯可部分回流至第二反應蒸餾塔124。在一些實施例中，第四產物更可包括少量的丙二醇。如此一來，第四產物中的丙二醇可在第二反應蒸餾塔124的底部形成塔底產物，且可進入再沸器130。一部分的第二反應蒸餾塔124的塔底產物於再沸器130中加熱後，可回流至第二反應蒸餾塔124。此外，另一部分的第二反應蒸餾塔124的塔底產物可回流至第一反應蒸餾塔104中，以循環利用。Step S106 is performed to allow excess methanol and a portion of the fourth product to enter the second reactive distillation column 124. A catalyst may be provided in the second reactive distillation column 124 (for example, a diagonal line region in the second reactive distillation column 124 shown in FIG. 1B). For example, the catalyst material may include sodium methoxide or organic non-ionic super strong base (proazaphosphatrane). The methanol and propylene carbonate in the fourth product are reacted and separated in the second reactive distillation column 124, and a fifth product including methanol and dimethyl carbonate is formed on the top of the second reactive distillation column 124. The fifth product may flow from the top of the second reactive distillation column 124 to the condenser 126. The fifth product may be stored in the reflux tank 128 after being condensed in the condenser 126. The condensed methanol and dimethyl carbonate in the reflux tank 128 may be partially refluxed to the second reactive distillation column 124. In some embodiments, the fourth product may further include a small amount of propylene glycol. In this way, the propylene glycol in the fourth product can form a bottom product at the bottom of the second reactive distillation column 124 and can enter the reboiler 130. A part of the bottom product of the second reactive distillation column 124 is heated in the reboiler 130 and then may be refluxed to the second reactive distillation column 124. In addition, another part of the bottom product of the second reactive distillation column 124 may be refluxed into the first reactive distillation column 104 for recycling.
進行步驟S108，使部分的第五產物以及萃取劑進入第二蒸餾塔134。第五產物中的甲醇與碳酸二甲酯可形成共沸物。萃取劑可經應用以改變甲醇與碳酸二甲酯的相對揮發度，亦即可分離第五產物中的甲醇與碳酸二甲酯。舉例而言，萃取劑可包括苯酚、苯胺、乙二醇單***或4-甲基-2-戊酮等。如此一來，第五產物可在第二蒸餾塔134中分離而形成包括甲醇的第六產物以及包括碳酸二甲酯的第七產物。第六產物可為第二蒸餾塔134的塔頂產物，且可自第二蒸餾塔134的頂部流至冷凝器136。第六產物在冷凝器136中冷凝後可儲存於回流槽138。回流槽138中冷凝的甲醇可部分回流至第二蒸餾塔134，且可部分回流至第二反應蒸餾塔124以循環利用。第七產物可為第二蒸餾塔134的塔底產物，且可進入再沸器140。第七產物於再沸器140中加熱後，可部分回流至第二蒸餾塔134中。Step S108 is performed to allow a part of the fifth product and the extractant to enter the second distillation column 134. Methanol and dimethyl carbonate in the fifth product can form an azeotrope. The extractant can be applied to change the relative volatility of methanol and dimethyl carbonate, that is, to separate methanol from dimethyl carbonate in the fifth product. For example, the extractant may include phenol, aniline, ethylene glycol monoethyl ether or 4-methyl-2-pentanone, and the like. As such, the fifth product can be separated in the second distillation column 134 to form a sixth product including methanol and a seventh product including dimethyl carbonate. The sixth product may be an overhead product of the second distillation column 134 and may flow from the top of the second distillation column 134 to the condenser 136. The sixth product can be stored in the reflux tank 138 after being condensed in the condenser 136. The condensed methanol in the reflux tank 138 may be partially refluxed to the second distillation column 134 and may be partially refluxed to the second reactive distillation column 124 for recycling. The seventh product may be a bottom product of the second distillation column 134 and may enter the reboiler 140. After the seventh product is heated in the reboiler 140, it may be partially refluxed into the second distillation column 134.
可進行步驟S110，使第七產物進入第三蒸餾塔144。在一些實施例中，第七產物更可包括萃取劑。第七產物中的碳酸二甲酯與萃取劑可在第三蒸餾塔144中分離而形成包括碳酸二甲指的第八產物與包括萃取劑的第九產物。第八產物可為第三蒸餾塔144的塔頂產物，且可自第三蒸餾塔144的頂部流至冷凝器146。第八產物中的碳酸二甲酯經冷凝後可儲存於回流槽148中。回流槽148中冷凝的碳酸二甲酯可部分回流至第三蒸餾塔144，且另一部分的碳酸二甲酯可作為本實施例的碳酸二甲酯的製造方法的產物。第九產物可為第三蒸餾塔144的塔底產物，且可部分回流至第二蒸餾塔134以循環利用，而另一部份可進入再沸器150且回流至第三蒸餾塔144中。Step S110 may be performed to make the seventh product enter the third distillation column 144. In some embodiments, the seventh product may further include an extractant. The dimethyl carbonate and the extractant in the seventh product can be separated in the third distillation column 144 to form an eighth product including dimethyl carbonate fingers and a ninth product including the extractant. The eighth product may be an overhead product of the third distillation column 144 and may flow from the top of the third distillation column 144 to the condenser 146. The dimethyl carbonate in the eighth product can be stored in the reflux tank 148 after being condensed. The dimethyl carbonate condensed in the reflux tank 148 may be partially refluxed to the third distillation column 144, and another portion of the dimethyl carbonate may be used as a product of the dimethyl carbonate manufacturing method of this embodiment. The ninth product may be a bottom product of the third distillation column 144 and may be partially refluxed to the second distillation column 134 for recycling, while another portion may enter the reboiler 150 and be refluxed into the third distillation column 144.
接下來，將以圖1B來說明本實施例的碳酸丙烯酯的製造裝置10與碳酸二甲酯的製造裝置10a。Next, the propylene carbonate manufacturing apparatus 10 and the dimethyl carbonate manufacturing apparatus 10a of this embodiment are demonstrated using FIG. 1B.
本實施例的碳酸丙烯酯的製造裝置10包括蒸餾系統102，且更可包括反應系統100。二氧化碳與氨氣可在反應系統100中進行反應以產生尿素。丙二醇以及上述反應系統100中所產生的尿素可作為蒸餾系統102的進料。蒸餾系統102包括第一部分102a與第二部分102b。在一些實施例中，第一部分102a與第二部分102b分別為互相連接的第一反應蒸餾塔104與第一蒸餾塔114。尿素與過量丙二醇在第一反應蒸餾塔104中進行反應與分離而形成包括氨氣的第一產物以及包括丙二醇與碳酸丙烯酯的第二產物。第一產物可為第一反應蒸餾塔104的塔頂產物，且第二產物可為第一反應蒸餾塔104的塔底產物。第二產物進入第一蒸餾塔114而分離以形成包括丙二醇的第三產物以及包括碳酸丙烯酯的第四產物。第三產物可為第一蒸餾塔114的塔頂產物，且第四產物可為第一蒸餾塔114的塔底產物。The propylene carbonate manufacturing apparatus 10 of this embodiment includes a distillation system 102 and may further include a reaction system 100. Carbon dioxide and ammonia can be reacted in the reaction system 100 to produce urea. Propylene glycol and urea produced in the reaction system 100 described above can be used as feed to the distillation system 102. The distillation system 102 includes a first portion 102a and a second portion 102b. In some embodiments, the first portion 102a and the second portion 102b are a first reactive distillation column 104 and a first distillation column 114 that are connected to each other, respectively. Urea and excess propylene glycol are reacted and separated in a first reactive distillation column 104 to form a first product including ammonia and a second product including propylene glycol and propylene carbonate. The first product may be a top product of the first reactive distillation column 104, and the second product may be a bottom product of the first reactive distillation column 104. The second product enters the first distillation column 114 and is separated to form a third product including propylene glycol and a fourth product including propylene carbonate. The third product may be a top product of the first distillation column 114, and the fourth product may be a bottom product of the first distillation column 114.
本實施例的碳酸二甲酯的製造裝置10a包括碳酸丙烯酯的製造裝置10，且更包括第二反應蒸餾塔124以及第二蒸餾塔134。甲醇以及上述的第四產物在第二反應蒸餾塔124中進行反應與分離，而在第二反應蒸餾塔124的頂部形成包括甲醇與碳酸二甲酯的第五產物。第五產物在具有萃取劑的第二蒸餾塔134中分離而形成包括甲醇的第六產物以及包括碳酸二甲酯的第七產物。The dimethyl carbonate manufacturing apparatus 10a of this embodiment includes a propylene carbonate manufacturing apparatus 10, and further includes a second reactive distillation column 124 and a second distillation column 134. Methanol and the aforementioned fourth product are reacted and separated in a second reactive distillation column 124, and a fifth product including methanol and dimethyl carbonate is formed on the top of the second reactive distillation column 124. The fifth product is separated in a second distillation column 134 having an extractant to form a sixth product including methanol and a seventh product including dimethyl carbonate.
在一些實施例中，第七產物更可包括萃取劑。此外，碳酸二甲酯的製造裝置10a更可包括第三蒸餾塔144。第七產物中的碳酸二甲酯與萃取劑在第三蒸餾塔144中分離而形成包括碳酸二甲酯的第八產物與包括萃取劑的第九產物。In some embodiments, the seventh product may further include an extractant. In addition, the dimethyl carbonate production apparatus 10 a may further include a third distillation column 144. The dimethyl carbonate in the seventh product is separated from the extractant in the third distillation column 144 to form an eighth product including the dimethyl carbonate and a ninth product including the extractant.
基於上述，尿素與丙二醇分別進入碳酸丙烯酯的製造裝置10的蒸餾系統102，以進行反應而產生碳酸丙烯酯。除此之外，丙二醇與作為產物的碳酸丙烯酯更可在蒸餾系統102中分離。因此，可提高作為產物的碳酸丙烯酯的純度，且可使本實施例的碳酸丙烯酯的製造方法及製造裝置具有較高的產物轉化率。如此一來，以較高純度的碳酸丙烯酯作為反應物製造碳酸二甲酯的方法及裝置亦可具有較高的產物轉化率。Based on the above, urea and propylene glycol enter the distillation system 102 of the propylene carbonate manufacturing apparatus 10, respectively, to perform a reaction to generate propylene carbonate. In addition, propylene glycol and propylene carbonate as products can be further separated in the distillation system 102. Therefore, the purity of the propylene carbonate as a product can be improved, and the method and device for manufacturing the propylene carbonate of this embodiment can have a high product conversion rate. In this way, the method and apparatus for producing dimethyl carbonate by using propylene carbonate of higher purity as a reactant can also have a higher product conversion rate.
接下來，將以圖2至圖4說明本發明第二實施例至第四實施例的碳酸丙烯酯的製造方法及製造裝置。圖2至圖4中與圖1B相同或相似的構件以相同的標號進行說明，且對於其功效或作用在此不再贅述。此外，以簡潔起見，圖2至圖4省略繪示反應系統100。Next, a method for manufacturing propylene carbonate and a device for manufacturing the second to fourth embodiments of the present invention will be described with reference to FIGS. 2 to 4. The components in FIG. 2 to FIG. 4 that are the same as or similar to those in FIG. 1B are described with the same reference numerals, and their effects or functions are not described herein again. In addition, for simplicity, the reaction system 100 is omitted in FIGS. 2 to 4.
圖2A至圖2C是依照本發明第二實施例的碳酸丙烯酯的製造裝置的示意圖。2A to 2C are schematic diagrams of an apparatus for manufacturing propylene carbonate according to a second embodiment of the present invention.
請參照圖1A、圖1B以及圖2A，第二實施例的碳酸丙烯酯的製造方法與第一實施例的碳酸丙烯酯的製造方法相似。兩者的差異在於本實施例的碳酸丙烯酯的製造方法更包括使第一反應蒸餾塔104的塔底液體與第一蒸餾塔114的塔頂氣體在第一熱交換裝置112中進行熱交換後，分別回流至第一反應蒸餾塔104的塔底與第一蒸餾塔114的塔頂。Please refer to FIG. 1A, FIG. 1B and FIG. 2A. The manufacturing method of the propylene carbonate of the second embodiment is similar to the manufacturing method of the propylene carbonate of the first embodiment. The difference between the two lies in that the method for producing propylene carbonate in this embodiment further includes heat-exchanging the bottom liquid of the first reactive distillation column 104 and the top gas of the first distillation column 114 in the first heat exchange device 112. And refluxed to the bottom of the first reactive distillation column 104 and the top of the first distillation column 114, respectively.
在一些實施例中，第一反應蒸餾塔104的液態的塔底產物（亦即第二產物）可自第一反應蒸餾塔104的塔底分別流至再沸器110、第一蒸餾塔114以及第一熱交換裝置112。此外，氣態的第一蒸餾塔114的塔頂產物（亦即第三產物）可自第一蒸餾塔114的頂部流至第一熱交換裝置112，且在第一熱交換裝置112中與第一反應蒸餾塔104的液態的塔底產物進行熱交換。第一反應蒸餾塔104的液態的塔底產物經加熱後可回流至第一反應蒸餾塔104中，以提供第一反應蒸餾塔104所需的部分熱能。因此，可降低再沸器110所需的能耗。在其他實施例中，第一蒸餾塔114的塔頂氣體甚至可提供第一反應蒸餾塔104所需的全部熱能，故可省略設置用以加熱第一反應蒸餾塔104的再沸器110。另一方面，第一蒸餾塔114的氣態的塔頂產物可在第一熱交換裝置112中經冷凝後進入回流槽118，故可省略設置用以將第一蒸餾塔114的塔頂產物冷凝的冷凝器。In some embodiments, the liquid bottom product (ie, the second product) of the first reactive distillation column 104 may flow from the bottom of the first reactive distillation column 104 to the reboiler 110, the first distillation column 114, and First heat exchange device 112. In addition, the top product (ie, the third product) of the gaseous first distillation column 114 may flow from the top of the first distillation column 114 to the first heat exchange device 112, and in the first heat exchange device 112, The liquid bottom product of the reactive distillation column 104 is subjected to heat exchange. The liquid bottom product of the first reactive distillation column 104 can be refluxed into the first reactive distillation column 104 after being heated to provide a part of the thermal energy required by the first reactive distillation column 104. Therefore, the energy consumption required for the reboiler 110 can be reduced. In other embodiments, the top gas of the first distillation column 114 can even provide all the thermal energy required by the first reactive distillation column 104, so the reboiler 110 provided to heat the first reactive distillation column 104 can be omitted. On the other hand, the gaseous overhead product of the first distillation column 114 can enter the reflux tank 118 after being condensed in the first heat exchanging device 112, so the installation of the overhead product to condense the overhead product of the first distillation column 114 can be omitted. Condenser.
請參照圖1B與圖2A，本實施例的碳酸丙烯酯的製造裝置20a與第一實施例的碳酸丙烯酯的製造裝置10相似。兩者的差異在於本實施例的碳酸丙烯酯的製造裝置20a更包括第一熱交換裝置112。第一熱交換裝置112連接於第一反應蒸餾塔104與第一蒸餾塔114之間，以使第一反應蒸餾塔104中的液體與第一蒸餾塔114中的氣體在第一熱交換裝置112中進行熱交換後，分別回流至第一反應蒸餾塔104與第一蒸餾塔114。Referring to FIG. 1B and FIG. 2A, the propylene carbonate manufacturing apparatus 20a of this embodiment is similar to the propylene carbonate manufacturing apparatus 10 of the first embodiment. The difference between the two is that the propylene carbonate manufacturing apparatus 20 a of this embodiment further includes a first heat exchange apparatus 112. The first heat exchange device 112 is connected between the first reactive distillation column 104 and the first distillation column 114, so that the liquid in the first reactive distillation column 104 and the gas in the first distillation column 114 are in the first heat exchange device 112. After heat exchange is performed in the medium, the mixture is refluxed to the first reactive distillation column 104 and the first distillation column 114, respectively.
請參照圖2B，在一些實施例中，碳酸丙烯酯的製造裝置20b的第一蒸餾塔114更可包括上段塔114a、下段塔114b以及氣體壓縮裝置114c。氣體壓縮裝置114c連接於上段塔114a與下段塔114b之間，以使下段塔114b中的氣體進入氣體壓縮裝置114c以產生壓縮產物，且使此壓縮產物進入上段塔114a而產生第一蒸餾塔114的塔頂產物。氣體壓縮裝置114c可提高氣體的溫度與壓力，故上段塔114a的溫度與壓力均可高於下段塔114b的溫度與壓力。如此一來，可避免丙二醇與碳酸丙烯酯在上段塔114a形成共沸物，且可使下段塔114b維持在相對低的溫度與壓力，而可降低再沸器120的能耗。Referring to FIG. 2B, in some embodiments, the first distillation column 114 of the propylene carbonate manufacturing device 20b may further include an upper column 114a, a lower column 114b, and a gas compression device 114c. The gas compression device 114c is connected between the upper column 114a and the lower column 114b, so that the gas in the lower column 114b enters the gas compression device 114c to generate a compressed product, and the compressed product is allowed to enter the upper column 114a to generate a first distillation column 114. Top product. The gas compression device 114c can increase the temperature and pressure of the gas, so the temperature and pressure of the upper stage tower 114a can be higher than the temperature and pressure of the lower stage tower 114b. In this way, propylene glycol and propylene carbonate can be prevented from forming an azeotrope in the upper column 114a, and the lower column 114b can be maintained at a relatively low temperature and pressure, thereby reducing the energy consumption of the reboiler 120.
此外，上段塔114a的塔頂氣體與第一反應蒸餾塔104的塔底液體在第一熱交換裝置112中進行熱交換後，分別回流至上段塔114a的塔頂與第一反應蒸餾塔104的塔底。由於上段塔114a具有相對高的溫度與壓力，故第一反應蒸餾塔104可藉由熱交換而從第一蒸餾塔114的上段塔114b得到更多的熱能。因此，可降低再沸器110所需的能耗。In addition, the top gas of the upper column 114a and the bottom liquid of the first reactive distillation column 104 are heat-exchanged in the first heat exchange device 112, and then returned to the top of the upper column 114a and the first reactive distillation column 104 respectively. The bottom of the tower. Because the upper column 114a has a relatively high temperature and pressure, the first reactive distillation column 104 can obtain more thermal energy from the upper column 114b of the first distillation column 114 through heat exchange. Therefore, the energy consumption required for the reboiler 110 can be reduced.
請參照圖2C，在一些實施例中，碳酸丙烯酯的製造裝置20c更可包括第二熱交換裝置113。第一蒸餾塔114的上段塔114a的塔頂中的部分氣體與下段塔114b的塔底液體可在第二熱交換裝置113中進行熱交換後，分別回流至上段塔114a的塔頂與下段塔114b的塔底。如此一來，下段塔114b可藉由熱交換而從上段塔114a得到足夠的熱能，故可省略設置再沸器120。Please refer to FIG. 2C. In some embodiments, the propylene carbonate manufacturing device 20 c may further include a second heat exchange device 113. Part of the gas in the top of the upper column 114a of the first distillation column 114 and the bottom liquid of the lower column 114b can be heat-exchanged in the second heat exchange device 113 and then returned to the top of the upper column 114a and the lower column respectively. 114b's bottom. In this way, the lower stage tower 114b can obtain sufficient thermal energy from the upper stage tower 114a by heat exchange, so the reboiler 120 can be omitted.
綜上所述，尿素與過量丙二醇分別進入碳酸丙烯酯的製造裝置的蒸餾系統，以進行反應而產生碳酸丙烯酯。除此之外，丙二醇與作為產物的碳酸丙烯酯更可在蒸餾系統中分離。因此，可提高作為產物的碳酸丙烯酯的純度，且可提高碳酸丙烯酯的轉化率。如此一來，以較高純度的碳酸丙烯酯作為反應物來製造碳酸二甲酯的方法及裝置亦可具有較高的產物轉化率。In summary, urea and excess propylene glycol respectively enter the distillation system of a propylene carbonate manufacturing device to perform a reaction to produce propylene carbonate. In addition, propylene glycol can be separated from propylene carbonate as a product in a distillation system. Therefore, the purity of propylene carbonate as a product can be improved, and the conversion rate of propylene carbonate can be improved. In this way, the method and device for producing dimethyl carbonate by using propylene carbonate of higher purity as a reactant can also have a higher product conversion rate.
在一些實施例中，碳酸丙烯酯的蒸餾系統可包括兩個相互連接的第一反應蒸餾塔與第一蒸餾塔。此外，可藉由設置連接於第一反應蒸餾塔與第一蒸餾塔之間的第一熱交換裝置，而可利用第一蒸餾塔的塔頂的熱能來加熱第一反應蒸餾塔的塔底，故可降第一反應蒸餾塔所需的能耗。In some embodiments, the propylene carbonate distillation system may include two first reactive distillation columns and a first distillation column that are interconnected. In addition, by setting a first heat exchange device connected between the first reactive distillation column and the first distillation column, the thermal energy at the top of the first distillation column can be used to heat the bottom of the first reactive distillation column. Therefore, the energy consumption required for the first reactive distillation column can be reduced.
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 the examples, it is not intended to limit the present invention. Any person with ordinary knowledge in the technical field can make some modifications and retouching without departing from the spirit and scope of the present invention. The protection scope of the present invention shall be determined by the scope of the attached patent application.
10、20a、20b、20c‧‧‧碳酸丙烯酯的製造裝置10, 20a, 20b, 20c ‧‧‧ propylene carbonate production equipment
10a‧‧‧碳酸二甲酯的製造裝置 10a‧‧‧Dimethyl carbonate manufacturing equipment
100‧‧‧反應系統 100‧‧‧ reaction system
101‧‧‧出口 101‧‧‧ exit
102‧‧‧蒸餾系統 102‧‧‧Distillation system
102a‧‧‧第一部分 102a‧‧‧Part I
102b‧‧‧第二部分 102b‧‧‧Part II
104‧‧‧第一反應蒸餾塔 104‧‧‧The first reactive distillation column
104a‧‧‧上段塔 104a‧‧‧Upper Tower
104b‧‧‧下段塔 104b‧‧‧lower tower
104c‧‧‧氣體壓縮裝置 104c‧‧‧Gas compression device
106‧‧‧部分冷凝器 106‧‧‧Partial condenser
108、118、128、138、148‧‧‧回流槽 108, 118, 128, 138, 148‧‧‧ return tank
110、120、130、140、150‧‧‧再沸器 110, 120, 130, 140, 150‧‧‧ reboilers
112‧‧‧第一熱交換裝置 112‧‧‧The first heat exchange device
113‧‧‧第二熱交換裝置 113‧‧‧Second heat exchange device
114‧‧‧第一蒸餾塔 114‧‧‧The first distillation column
116、126、136、146‧‧‧冷凝器 116, 126, 136, 146‧‧‧ condenser
124‧‧‧第二反應蒸餾塔 124‧‧‧Second reactive distillation column
134‧‧‧第二蒸餾塔 134‧‧‧Second distillation column
144‧‧‧第三蒸餾塔 144‧‧‧The third distillation column
S100、S102、S104、S106、S108、S110‧‧‧步驟 S100, S102, S104, S106, S108, S110‧‧‧ steps
圖1A是依照本發明第一實施例的一種碳酸丙烯酯與碳酸二甲酯的製造方法的流程圖。 圖1B是依照本發明第一實施例的一種碳酸丙烯酯與碳酸二甲酯的製造裝置的示意圖。 圖2A至圖2C是依照本發明第二實施例的碳酸丙烯酯的製造裝置的示意圖。FIG. 1A is a flowchart of a method for manufacturing propylene carbonate and dimethyl carbonate according to a first embodiment of the present invention. FIG. 1B is a schematic diagram of an apparatus for manufacturing propylene carbonate and dimethyl carbonate according to the first embodiment of the present invention. 2A to 2C are schematic diagrams of an apparatus for manufacturing propylene carbonate according to a second embodiment of the present invention.
Claims (14)
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| CN1212172A (en) * | 1997-09-24 | 1999-03-31 | 中国石油化工总公司 | Process for separating azeotrope of methanol and dimethyl carbonate |
| CN105517682A (en) * | 2013-09-06 | 2016-04-20 | 株式会社大赛璐 | Method and plant for using recompressed vapor |
| CN105601609A (en) * | 2016-03-09 | 2016-05-25 | 屈强好 | Method for using ionic liquid catalyst for catalyzing urea and propylene glycol to synthesize propylene carbonate |
| CN106478421A (en) * | 2015-08-31 | 2017-03-08 | 亚申科技研发中心（上海）有限公司 | DMC Processes |
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| CN103626656A (en) * | 2012-08-27 | 2014-03-12 | 亚申科技研发中心（上海）有限公司 | Method for separating dimethyl carbonate and methanol through pressure-swing distillation of heat pump, and apparatus thereof |
| CN105985310A (en) * | 2015-02-12 | 2016-10-05 | 屈强好 | Method for producing propylene carbonate from urea and 1,2-propylene glycol |
| CN106146310A (en) * | 2016-08-26 | 2016-11-23 | 中建安装工程有限公司 | A kind of device producing dimethyl carbonate and technique |
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| CN1212172A (en) * | 1997-09-24 | 1999-03-31 | 中国石油化工总公司 | Process for separating azeotrope of methanol and dimethyl carbonate |
| CN105517682A (en) * | 2013-09-06 | 2016-04-20 | 株式会社大赛璐 | Method and plant for using recompressed vapor |
| CN106478421A (en) * | 2015-08-31 | 2017-03-08 | 亚申科技研发中心（上海）有限公司 | DMC Processes |
| CN105601609A (en) * | 2016-03-09 | 2016-05-25 | 屈强好 | Method for using ionic liquid catalyst for catalyzing urea and propylene glycol to synthesize propylene carbonate |
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