TW202225130A - Method and device for manufacturing compounds from isobutyric acid and acetic anhydride - Google Patents
Method and device for manufacturing compounds from isobutyric acid and acetic anhydride Download PDFInfo
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本揭露關於一種利用異丁酸及乙酸酐製備化合物之方法及裝置。The present disclosure relates to a method and apparatus for preparing compounds using isobutyric acid and acetic anhydride.
2,2,4,4-四甲基-1,3-環丁烷二醇(2,2,4,4 - teramethyl -1,3- cyclobutanediol, CBDO)是具對稱結構的多功能中間體,廣泛應用於共聚聚酯的合成領域,例如用於合成可替代聚碳酸酯(PC)的高性能聚酯。傳統聚酯的玻璃轉移溫度較低,在中高溫領域的應用受到一定限制。加入2,2,4,4-四甲基-1,3-環丁烷二醇可顯著提高聚酯的玻璃轉移溫度、耐候性及透明度。使用2,2,4,4-四甲基-1,3-環丁烷二醇合成的聚酯具有與雙酚A類似的優良物理特性,例如抗衝擊強度高、尺寸穩定性優異、玻璃轉移溫度高。2,2,4,4-Tetramethyl-1,3-cyclobutanediol (2,2,4,4-teramethyl-1,3-cyclobutanediol, CBDO) is a multifunctional intermediate with symmetrical structure, It is widely used in the synthesis of copolyesters, such as high-performance polyesters that can replace polycarbonate (PC). The glass transition temperature of traditional polyester is low, and its application in medium and high temperature fields is limited. Adding 2,2,4,4-tetramethyl-1,3-cyclobutanediol can significantly improve the glass transition temperature, weather resistance and transparency of polyester. Polyester synthesized using 2,2,4,4-tetramethyl-1,3-cyclobutanediol has excellent physical properties similar to bisphenol A, such as high impact strength, excellent dimensional stability, glass transition High temperature.
不斷改善和控制化學反應製程(例如:環境友善製程、降低能耗及廢棄物排放、提高產率及純度)是化學工業中持續努力的目標。基於上述,業界需要一種新穎的2,2,4,4-四甲基-1,3-環丁烷二醇的製程,以提昇所得產物的產率以及降低副產物的產生。Continuous improvement and control of chemical reaction processes (eg, environmentally friendly processes, reduced energy consumption and waste emissions, increased yield and purity) is an ongoing goal in the chemical industry. Based on the above, the industry needs a novel process for the preparation of 2,2,4,4-tetramethyl-1,3-cyclobutanediol, so as to improve the yield of the obtained product and reduce the generation of by-products.
根據本揭露實施例,本揭露提供一種利用異丁酸及乙酸酐製備化合物之方法。該利用異丁酸及乙酸酐製備化合物之方法包含以下步驟。將異丁酸及乙酸酐進行反應,得到一第一混合物,其中該第一混合物包含異丁酸酐及醋酸。對第一混合物進行一第一純化製程,得到異丁酸酐以及醋酸;對異丁酸酐進行一裂解製程,得到一第二混合物,其中第二混合物包含二甲基烯酮 、異丁酸與異丁酸酐;對該第二混合物進行一氣液分離製程,得到二甲基烯酮氣體及一液體,其中該液體包含異丁酸與異丁酸酐;以及收集該液體,並使該液體內的異丁酸與乙酸酐反應。根據本揭露實施例,該利用異丁酸及乙酸酐製備化合物之方法可更包含以下步驟之至少一者。在進行該第一純化製程後,收集該醋酸。利用一噴射抽吸製程以在5℃至25℃以及常壓(例如約750 Torr至770 Torr)下收集該二甲基烯酮氣體。對二甲基烯酮進行二聚反應,得到2,2,4,4-四甲基-1,3-環丁烷二酮。將2,2,4,4-四甲基-1,3-環丁烷二酮與一溶劑混合得到一溶液,其中該溶液的固含量為5wt%至20 wt%。將該溶液與氫氣進行氫化反應,得到一第三混合物,其中該第三混合物包含2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、以及溶劑。對第三混合物進行一第二純化製程,得到2,2,4,4-四甲基-1,3-環丁烷二醇。According to an embodiment of the present disclosure, the present disclosure provides a method for preparing a compound using isobutyric acid and acetic anhydride. The method for preparing compounds using isobutyric acid and acetic anhydride includes the following steps. The isobutyric acid and acetic anhydride are reacted to obtain a first mixture, wherein the first mixture comprises isobutyric anhydride and acetic acid. A first purification process is performed on the first mixture to obtain isobutyric anhydride and acetic acid; a cracking process is performed on the isobutyric anhydride to obtain a second mixture, wherein the second mixture comprises dimethylketene, isobutyric acid and isobutyl acid anhydride; perform a gas-liquid separation process on the second mixture to obtain dimethyl ketene gas and a liquid, wherein the liquid contains isobutyric acid and isobutyric anhydride; and collect the liquid, and make the isobutyric acid in the liquid Reacts with acetic anhydride. According to an embodiment of the present disclosure, the method for preparing a compound using isobutyric acid and acetic anhydride may further include at least one of the following steps. After the first purification process, the acetic acid is collected. A jet suction process is used to collect the dimethylketene gas at 5°C to 25°C and atmospheric pressure (eg, about 750 Torr to 770 Torr). Dimerization of dimethylketene yields 2,2,4,4-tetramethyl-1,3-cyclobutanedione. The 2,2,4,4-tetramethyl-1,3-cyclobutanedione is mixed with a solvent to obtain a solution, wherein the solid content of the solution is 5 wt % to 20 wt %. The solution is hydrogenated with hydrogen to obtain a third mixture, wherein the third mixture comprises 2,2,4,4-tetramethyl-1,3-cyclobutanediol, hydrogen, and a solvent. A second purification process is performed on the third mixture to obtain 2,2,4,4-tetramethyl-1,3-cyclobutanediol.
根據本揭露實施例,本揭露提供一種異丁酸及乙酸酐製備化合物之裝置。該異丁酸及乙酸酐製備化合物之裝置包含一進料單元;一第一反應單元,其中該進料單元與該第一反應單元連接,以將異丁酸及乙酸酐由進料單元導入該第一反應單元,其中該異丁酸在該第一反應單元與乙酸酐反應得到一第一混合物,其中該第一混合物包含異丁酸酐及醋酸;一第一純化單元,其中該第一反應單元與該第一純化單元連接,以將該第一混合物導入該第一純化單元,其中該第一混合物在該第一純化單元中進行一第一純化製程,得到異丁酸酐以及醋酸;一裂解單元,其中該第一純化單元與該裂解單元連接,以將異丁酸酐導入該裂解單元,其中異丁酸酐在該裂解單元進行一裂解製程,得到一第二混合物,其中第二混合物包含二甲基烯酮 、異丁酸與異丁酸酐;以及,一氣液分離單元,其中該裂解單元與該氣液分離單元連接,以將第二混合物導入該氣液分離單元,其中該第二混合物在氣液分離單元分離成一二甲基烯酮氣體及一液體,其中液體包含異丁酸與異丁酸酐,其中該進料單元與該氣液分離單元連接,以將該液體導入該進料單元。根據本揭露實施例,該利用異丁酸及乙酸酐製備化合物之方法可更包含以下單元之至少一者。一醋酸收集單元,其中該醋酸收集單元與該第一純化單元連接,用以收集由第一純化單元所獲得之醋酸。一第二反應單元,其中該氣液分離單元與該第二反應單元連接,以將該二甲基烯酮氣體導入該第二反應單元,其中該二甲基烯酮氣體在該第二反應單元中反應形成2,2,4,4-四甲基-1,3-環丁烷二酮。一抽吸單元,其中該第二反應單元藉由該抽吸單元與該氣液分離單元連接,其中該抽吸單元對該二甲基烯酮氣體進行一噴射抽吸製程,以使第二反應單元在5℃至25℃以及常壓(例如750 Torr至770 Torr)下接收該二甲基烯酮氣體。一溶劑供給單元,其中該溶劑供給單元與該抽吸單元連接,以供應該抽吸單元一溶劑進行該噴射抽吸製程。一固液分離單元,其中該第二反應單元與該固液分離單元連接,以將第二反應單元中之溶劑及2,2,4,4-四甲基-1,3-環丁烷二酮導入該固液分離單元,使2,2,4,4-四甲基-1,3-環丁烷二酮以固體形式與溶劑分離。一氫化單元,其中該固液分離單元與該氫化單元連接以將2,2,4,4-四甲基-1,3-環丁烷二酮導入氫化單元,其中該溶劑供給單元與該氫化單元連接以將溶劑導入氫化單元,其中該2,2,4,4-四甲基-1,3-環丁烷二酮在溶劑存在下與一氫氣進行反應,得到一第三混合物,其中該第三混合物包含2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、以及溶劑。一第二純化單元,其中該氫化單元與該第二純化單元連接以將第三混合物導入第二純化單元,其中該第三混合物在第二純化單元進行一純化製程,得到2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、及溶劑。一收集單元, 其中該收集單元與該第二純化單元連接,用以收集2,2,4,4-四甲基-1,3-環丁烷二醇。According to an embodiment of the present disclosure, the present disclosure provides an apparatus for preparing compounds from isobutyric acid and acetic anhydride. The device for preparing compounds from isobutyric acid and acetic anhydride comprises a feeding unit; a first reaction unit, wherein the feeding unit is connected with the first reaction unit, so as to introduce isobutyric acid and acetic anhydride from the feeding unit into the first reaction unit a first reaction unit, wherein the isobutyric acid reacts with acetic anhydride in the first reaction unit to obtain a first mixture, wherein the first mixture comprises isobutyric anhydride and acetic acid; a first purification unit, wherein the first reaction unit Connected with the first purification unit to introduce the first mixture into the first purification unit, wherein the first mixture is subjected to a first purification process in the first purification unit to obtain isobutyric anhydride and acetic acid; a cracking unit , wherein the first purification unit is connected to the cleavage unit to introduce isobutyric anhydride into the cleavage unit, wherein the isobutyric anhydride undergoes a cleavage process in the cleavage unit to obtain a second mixture, wherein the second mixture comprises dimethyl Enone, isobutyric acid and isobutyric anhydride; and, a gas-liquid separation unit, wherein the cracking unit is connected with the gas-liquid separation unit to introduce the second mixture into the gas-liquid separation unit, wherein the second mixture is in the gas-liquid separation unit The separation unit is separated into a dimethylketene gas and a liquid, wherein the liquid contains isobutyric acid and isobutyric anhydride, wherein the feed unit is connected with the gas-liquid separation unit to introduce the liquid into the feed unit. According to an embodiment of the present disclosure, the method for preparing a compound using isobutyric acid and acetic anhydride may further comprise at least one of the following units. An acetic acid collection unit, wherein the acetic acid collection unit is connected with the first purification unit for collecting the acetic acid obtained by the first purification unit. A second reaction unit, wherein the gas-liquid separation unit is connected to the second reaction unit to introduce the dimethyl ketene gas into the second reaction unit, wherein the dimethyl ketene gas is in the second reaction unit During the reaction, 2,2,4,4-tetramethyl-1,3-cyclobutanedione is formed. a suction unit, wherein the second reaction unit is connected with the gas-liquid separation unit through the suction unit, wherein the suction unit performs a jet suction process on the dimethylketene gas to make the second reaction The unit receives the dimethylketene gas at 5°C to 25°C and atmospheric pressure (eg, 750 Torr to 770 Torr). A solvent supply unit, wherein the solvent supply unit is connected with the suction unit to supply a solvent to the suction unit to perform the jet suction process. A solid-liquid separation unit, wherein the second reaction unit is connected with the solid-liquid separation unit to separate the solvent and 2,2,4,4-tetramethyl-1,3-cyclobutane in the second reaction unit The ketone is introduced into the solid-liquid separation unit, and 2,2,4,4-tetramethyl-1,3-cyclobutanedione is separated from the solvent as a solid. A hydrogenation unit, wherein the solid-liquid separation unit is connected to the hydrogenation unit to introduce 2,2,4,4-tetramethyl-1,3-cyclobutanedione into a hydrogenation unit, wherein the solvent supply unit is connected to the hydrogenation unit units are connected to introduce a solvent into the hydrogenation unit, wherein the 2,2,4,4-tetramethyl-1,3-cyclobutanedione is reacted with a hydrogen gas in the presence of a solvent to give a third mixture wherein the The third mixture contains 2,2,4,4-tetramethyl-1,3-cyclobutanediol, hydrogen, and solvent. A second purification unit, wherein the hydrogenation unit is connected to the second purification unit to introduce the third mixture into the second purification unit, wherein the third mixture is subjected to a purification process in the second purification unit to obtain 2,2,4, 4-Tetramethyl-1,3-cyclobutanediol, hydrogen, and solvent. A collection unit, wherein the collection unit is connected with the second purification unit for collecting 2,2,4,4-tetramethyl-1,3-cyclobutanediol.
根據本揭露實施例,本揭露提供一種利用異丁酸及乙酸酐製備化合物之方法。該利用異丁酸及乙酸酐製備化合物之方法係以上述裝置進行,包含以下步驟。將異丁酸及乙酸酐在該第一反應單元中反應,得到一第一混合物,其中該第一混合物包含異丁酸酐及醋酸。將第一混合物導入該第一純化單元以對該第一混合物進行一第一純化製程,得到異丁酸酐以及醋酸。將異丁酸酐導入一裂解單元以對異丁酸酐進行一裂解製程,得到一第二混合物,其中第二混合物包含二甲基烯酮 、異丁酸與異丁酸酐。將第二混合物導入一氣液分離單元以對該第二混合物進行一氣液分離製程,得到二甲基烯酮氣體及一液體,其中該液體包含異丁酸與異丁酸酐。將該液體導入該進料單元。根據本揭露實施例,該利用異丁酸及乙酸酐製備化合物之方法可更包含以下步驟之至少一者。將異丁酸及乙酸酐由該進料單元導入至該第一反應單元內。將所得之醋酸導入一醋酸收集單元。將包含異丁酸與異丁酸酐之液體由該進料單元導入該第一反應單元以使該液體中的異丁酸與乙酸酐反應。將該二甲基烯酮氣體導入一第二反應單元。將二甲基烯酮氣體在該第二反應單元中進行二聚反應形成2,2,4,4-四甲基-1,3-環丁烷二酮。利用一抽吸單元對二甲基烯酮進行一噴射抽吸製程,以將二甲基烯酮氣體由該氣液分離單元導入該第二反應單元。利用一溶劑供給單元供應該抽吸單元一溶劑,以進行該噴射抽吸製程。將2,2,4,4-四甲基-1,3-環丁烷二酮以及該溶劑在一氫化單元內混合,得到一溶液,其中該溶液的固含量為5wt%至20 wt%。將該溶液與氫氣在該氫化單元內進行氫化反應,得到一第三混合物,其中該第三混合物包含2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、以及溶劑。將第三混合物導入一第二純化單元以對該第三混合物進行一第二純化製程,得到2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、及溶劑。利用該溶劑供給單元回收由該第二純化製程所分離的溶劑。將由該第二純化製程所分離的氫氣導入該氫化單元。將第二純化製程所分離的2,2,4,4-四甲基-1,3-環丁烷二醇導入一收集單元。According to an embodiment of the present disclosure, the present disclosure provides a method for preparing a compound using isobutyric acid and acetic anhydride. The method for preparing compounds using isobutyric acid and acetic anhydride is carried out with the above-mentioned apparatus, and includes the following steps. Isobutyric acid and acetic anhydride are reacted in the first reaction unit to obtain a first mixture, wherein the first mixture comprises isobutyric anhydride and acetic acid. The first mixture is introduced into the first purification unit to perform a first purification process on the first mixture to obtain isobutyric anhydride and acetic acid. The isobutyric anhydride is introduced into a cracking unit to perform a cracking process on the isobutyric anhydride to obtain a second mixture, wherein the second mixture comprises dimethylketene, isobutyric acid and isobutyric anhydride. The second mixture is introduced into a gas-liquid separation unit to perform a gas-liquid separation process on the second mixture to obtain dimethylketene gas and a liquid, wherein the liquid contains isobutyric acid and isobutyric anhydride. The liquid is introduced into the feed unit. According to an embodiment of the present disclosure, the method for preparing a compound using isobutyric acid and acetic anhydride may further include at least one of the following steps. Isobutyric acid and acetic anhydride were introduced from the feed unit into the first reaction unit. The resulting acetic acid is introduced into an acetic acid collection unit. A liquid comprising isobutyric acid and isobutyric anhydride is introduced from the feed unit to the first reaction unit to react the isobutyric acid and acetic anhydride in the liquid. The dimethylketene gas is introduced into a second reaction unit. Dimethylketene gas is dimerized in this second reaction unit to form 2,2,4,4-tetramethyl-1,3-cyclobutanedione. A jet suction process is performed on dimethylketene by a suction unit, so that the dimethylketene gas is introduced into the second reaction unit from the gas-liquid separation unit. A solvent supply unit is used to supply the suction unit with a solvent to perform the jet suction process. The 2,2,4,4-tetramethyl-1,3-cyclobutanedione and the solvent are mixed in a hydrogenation unit to obtain a solution, wherein the solid content of the solution is 5wt% to 20wt%. The solution is hydrogenated with hydrogen in the hydrogenation unit to obtain a third mixture, wherein the third mixture comprises 2,2,4,4-tetramethyl-1,3-cyclobutanediol, hydrogen, and solvent. The third mixture is introduced into a second purification unit to perform a second purification process on the third mixture to obtain 2,2,4,4-tetramethyl-1,3-cyclobutanediol, hydrogen, and a solvent . The solvent separated by the second purification process is recovered by the solvent supply unit. The hydrogen separated by the second purification process is introduced into the hydrogenation unit. The 2,2,4,4-tetramethyl-1,3-cyclobutanediol separated in the second purification process is introduced into a collection unit.
以下針對本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置作詳細說明。應了解的是,以下之敘述提供許多不同的實施例或例子,用以實施本發明之不同樣態。以下所述特定的元件及排列方式僅為簡單描述本發明。當然,這些僅用以舉例而非本發明之限定。此外,在不同實施例中可能使用重複的標號或標示。這些重複僅為了簡單清楚地敘述本發明,不代表所討論之不同實施例及/或結構之間具有任何關連性。The method and apparatus for preparing compounds using isobutyric acid and acetic anhydride according to the present disclosure will be described in detail below. It should be appreciated that the following description provides many different embodiments or examples for implementing different aspects of the invention. The specific elements and arrangements described below are merely illustrative of the invention. Of course, these are only used as examples rather than limitations of the present invention. Furthermore, repeated reference numbers or designations may be used in different embodiments. These repetitions are for simplicity and clarity of description of the present invention and do not represent any association between the different embodiments and/or structures discussed.
必需了解的是,為特別描述或圖示之元件可以此技術人士所熟知之各種形式存在。說明書與請求項中所使用的序數例如”第一”、”第二”、”第三”等之用詞,以修飾請求項之元件,其本身並不意含及代表該請求元件有任何之前的序數,也不代表某一請求元件與另一請求元件的順序、或是製造方法上的順序,該些序數的使用僅用來使具有某命名的一請求元件得以和另一具有相同命名的請求元件能作出清楚區分。It must be understood that the elements specifically described or illustrated may exist in various forms well known to those skilled in the art. The ordinal numbers such as "first", "second", "third", etc. used in the description and the claimed items are used to modify the elements of the claimed items, and they do not imply and represent that the claimed elements have any preceding elements. The ordinal numbers do not represent the order of a request element and another request element, or the order of the manufacturing method. The use of these ordinal numbers is only used to make a request element with a certain name and another request with the same name. Components can be clearly distinguished.
本揭露提供一種利用異丁酸及乙酸酐製備化合物之方法及裝置。根據本揭露實施例,利用異丁酸及乙酸酐製備之化合物可為醋酸、二甲基烯酮、2,2,4,4-四甲基-1,3-環丁烷二酮、及或2,2,4,4-四甲基-1,3-環丁烷二醇。本揭露所述利用異丁酸及乙酸酐製備化合物之方法可為一連續式製程,且該利用異丁酸及乙酸酐製備化合物之裝置可應用於該利用異丁酸及乙酸酐製備化合物之方法。The present disclosure provides a method and apparatus for preparing compounds using isobutyric acid and acetic anhydride. According to an embodiment of the present disclosure, the compound prepared using isobutyric acid and acetic anhydride may be acetic acid, dimethylketene, 2,2,4,4-tetramethyl-1,3-cyclobutanedione, and or 2,2,4,4-Tetramethyl-1,3-cyclobutanediol. The method for preparing compounds using isobutyric acid and acetic anhydride in the present disclosure can be a continuous process, and the device for preparing compounds using isobutyric acid and acetic anhydride can be applied to the method for preparing compounds using isobutyric acid and acetic anhydride .
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置除了可包含異丁酸酐的製備及裂解,並可進一步包含二甲基烯酮氣體的二聚反應、以及2,2,4,4-四甲基-1,3-環丁烷二酮的氫化反應。根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置可將異丁酸酐經裂解後所得副產物(例如異丁酸)以及未反應的起始物(例如異丁酸酐)再利用。According to an embodiment of the present disclosure, the method and apparatus for preparing a compound using isobutyric acid and acetic anhydride described in the present disclosure may further include the preparation and cracking of isobutyric anhydride, and may further include dimerization of dimethylketene gas, and Hydrogenation of 2,2,4,4-tetramethyl-1,3-cyclobutanedione. According to the embodiments of the present disclosure, the method and device for preparing compounds using isobutyric acid and acetic anhydride described in the present disclosure can be used to obtain by-products (such as isobutyric acid) and unreacted starting materials (such as isobutyric anhydride) obtained after the cleavage of isobutyric anhydride. butyric anhydride) for reuse.
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置,可利用一噴射抽吸製程收集所得之二甲基烯酮氣體。由於噴射抽吸製程的壓力差來自於溶劑的流速,因此可在5℃至25℃以及常壓(例如750 Torr至770 Torr)下收集二甲基烯酮氣體,改善二甲基烯酮氣體的收集效率。習知技術係以低溫低壓液相吸收製程來收集液態二甲基烯酮,因此需要利用低壓(例如小於80 Torr)來降低二甲基烯酮的沸點,並在低溫(例如小於-10℃)的環境下收集二甲基烯酮。因此,與習知低溫低壓液相吸收製程相比,本揭露採用噴射抽吸製程來收集二甲基烯酮氣體,除了可大幅降低能耗外,亦可降低二甲基烯酮的逸失(即提高二甲基烯酮的收率)。According to an embodiment of the present disclosure, the method and apparatus for preparing a compound using isobutyric acid and acetic anhydride described in the present disclosure can utilize a jet suction process to collect the obtained dimethylketene gas. Since the pressure difference of the jet suction process comes from the flow rate of the solvent, the dimethylketene gas can be collected at 5°C to 25°C and normal pressure (eg, 750 Torr to 770 Torr) to improve the dimethylketene gas. collection efficiency. The conventional technology is to collect liquid dimethyl ketene with a low temperature and low pressure liquid phase absorption process, so it is necessary to use low pressure (for example, less than 80 Torr) to reduce the boiling point of dimethyl ketene, and at low temperature (for example, less than -10 ℃) The dimethylketene was collected in the environment. Therefore, compared with the conventional low temperature and low pressure liquid phase absorption process, the present disclosure adopts the jet suction process to collect the dimethylketene gas, which not only greatly reduces energy consumption, but also reduces the loss of dimethylketene (ie increase the yield of dimethylketene).
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置,係在相對低溫(例如低於75℃)下對二甲基烯酮進行二聚反應形成2,2,4,4-四甲基-1,3-環丁烷二酮。如此一來,可降低副產物(例如寡聚物)生成,提高2,2,4,4-四甲基-1,3-環丁烷二酮的選擇率。根據本揭露實施例,藉由二聚反應形成2,2,4,4-四甲基-1,3-環丁烷二酮的選擇率可高達96%以上。According to an embodiment of the present disclosure, the method and apparatus for preparing a compound using isobutyric acid and acetic anhydride described in the present disclosure is to dimerize dimethylketene at a relatively low temperature (eg, below 75° C.) to form 2,2 ,4,4-tetramethyl-1,3-cyclobutanedione. In this way, the generation of by-products (eg, oligomers) can be reduced, and the selectivity of 2,2,4,4-tetramethyl-1,3-cyclobutanedione can be improved. According to the embodiment of the present disclosure, the selectivity of forming 2,2,4,4-tetramethyl-1,3-cyclobutanedione by dimerization can be as high as 96% or more.
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置,係在相對低溫(例如低於80℃)下對2,2,4,4-四甲基-1,3-環丁烷二酮進行氫化反應。如此一來,可大幅降低副產物(例如環酮副產物、開環酮類副產物、或2,2,4-三甲基-1,3-戊二醇)的生成。根據本揭露實施例,藉由氫化反應形成2,2,4,4-四甲基-1,3-環丁烷二醇的選擇率可高達96%以上。According to an embodiment of the present disclosure, the method and apparatus for preparing a compound using isobutyric acid and acetic anhydride described in the present disclosure is a relatively low temperature (eg, lower than 80° C.) for 2,2,4,4-tetramethyl-1 , 3-cyclobutanedione was hydrogenated. In this way, the generation of by-products (eg, by-products of cyclic ketones, by-products of ring-opened ketones, or 2,2,4-trimethyl-1,3-pentanediol) can be greatly reduced. According to an embodiment of the present disclosure, the selectivity of forming 2,2,4,4-tetramethyl-1,3-cyclobutanediol by hydrogenation can be as high as 96% or more.
第1圖為本揭露一實施例所述利用異丁酸及乙酸酐製備化合物之方法10之步驟流程圖。FIG. 1 is a flow chart showing the steps of a
本揭露所述利用異丁酸及乙酸酐製備化合物之方法10包含以下步驟。首先,將異丁酸及乙酸酐進行反應(例如酯化反應),得到一第一混合物 (步驟12) ,其中該第一混合物包含異丁酸酐及醋酸。根據本揭露實施例,在進行反應前,可將異丁酸及乙酸酐充份混合。接著,將步驟12所得第一混合物進行一第一純化製程,得到異丁酸酐以及醋酸(步驟14)。根據本揭露實施例,該第一純化製程可包含一蒸餾製程。根據本揭露實施例,該第一純化製程可包含一攪拌製程及一蒸餾製程。在對該第一混合物進行蒸餾製程前,對該第一混合物進行攪拌製程。根據本揭露實施例,在進行該第一純化製程後,收集該醋酸。接著,對步驟14所得異丁酸酐進行一裂解製程,得到一第二混合物,其中第二混合物包含二甲基烯酮 、異丁酸與異丁酸酐(步驟16)。在該裂解製程中,異丁酸酐可先在280℃至350℃下進行預熱,接著加熱異丁酸酐到400℃至500℃之間以熱裂解異丁酸酐。根據本揭露實施例,該裂解製程的壓力可介於60 Torr至120 Torr之間,製程的時間可介於0.01秒至1秒之間,且異丁酸酐的轉化率可大於或等於45%,例如介於45%至70%之間。根據本揭露實施例,可搭配載氣(例如氬氣或氮氣)與異丁酸酐的氣體混合後再進行該裂解製程。接著,對步驟16所得第二混合物進行一氣液分離製程,得到二甲基烯酮氣體及一液體,其中該液體包含異丁酸與異丁酸酐(步驟18)。The
根據本揭露實施例,在進行氣液分離製程後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法10可更包含:收集該液體,並使該液體內的異丁酸與乙酸酐反應(步驟20)。According to an embodiment of the present disclosure, after the gas-liquid separation process is performed, the
第2圖為本揭露某些實施例所述利用異丁酸及乙酸酐製備化合物之方法50之步驟流程圖。根據本揭露實施例,在進行氣液分離製程後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法50可更包含:利用一噴射抽吸製程在5℃至25℃以及750 Torr至770 Torr下收集該二甲基烯酮氣體(步驟22)。本揭露採用噴射抽吸製程來收集二甲基烯酮氣體,除了可大幅降低能耗(即可在常壓下收集二甲基烯酮,無需降溫至-10℃以下)外,亦可降低二甲基烯酮的逸失(即提高二甲基烯酮的收率)。根據本揭露實施例,該噴射抽吸製程的壓力差來自於溶劑的流速,而所使用的溶劑可為酯類溶劑,例如異丁酸異丁酯、丙酸乙酯、或乙酸辛酯。根據本揭露實施例,在進行噴射抽吸製程中,該溶劑可溶解(吸收)二甲基烯酮,形成含二甲基烯酮的酯類溶液。根據本揭露實施例,該含二甲基烯酮的酯類溶液的二甲基烯酮濃度可為10wt%至40wt%,以該二甲基烯酮及溶劑的總重為基準。根據本揭露實施例,在收集該二甲基烯酮氣體(或形成含二甲基烯酮的酯類溶液)後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法50可更包含:對二甲基烯酮進行二聚反應,得到2,2,4,4-四甲基-1,3-環丁烷二酮(2,2,4,4-Tetramethyl-1,3-cyclobutanedione,TMCD)(步驟24)。根據本揭露實施例,該二聚反應的溫度可控制在為20℃至75℃。若反應溫度過低,則反應過慢,需要增加反應時間。若反應溫度過高,則在二聚反應中會產生副產物(例如聚酯或聚酮的寡聚物),降低2,2,4,4-四甲基-1,3-環丁烷二酮產率及純度。舉例來說,將二甲基烯酮在75℃下進行二聚反應,所得的聚酯或聚酮寡聚物的量將會增加約1.42倍(與二甲基烯酮在70℃下進行二聚反應所得的聚酯或聚酮寡聚物的量相比)。根據本揭露實施例,該二聚反應的時間可介於2小時至24小時之間。FIG. 2 is a flow chart of the steps of a
此外,根據本揭露實施例,該二聚反應可在惰性氣體(如氮氣或氬氣)環境下進行。根據本揭露實施例,二甲基烯酮可在一觸媒存在下進行二聚反應。本揭露對於所使用的觸媒並無限制,可為習知對二甲基烯酮進行二聚反應所使用的觸媒。根據本揭露實施例,若使用酯類溶劑(例如異丁酸異丁酯),由於酯類溶劑對2,2,4,4-四甲基-1,3-環丁二酮的溶解度較低,二聚反應後所形成的2,2,4,4-四甲基-1,3-環丁二酮會傾向析出。因此,待二聚反應結束後,可利用一製程(例如再結晶製程及/或過濾製程)收集2,2,4,4-四甲基-1,3-環丁二酮固體,並以溶劑進行清洗,得到高純度的2,2,4,4-四甲基-1,3-環丁二酮(純度可大於99wt%)。Furthermore, according to an embodiment of the present disclosure, the dimerization reaction can be performed in an environment of inert gas (eg, nitrogen or argon). According to an embodiment of the present disclosure, the dimerization reaction of dimethylketene can be carried out in the presence of a catalyst. The present disclosure does not limit the catalyst used, and it can be a conventional catalyst used for dimerization of dimethylketene. According to the embodiment of the present disclosure, if an ester solvent (eg, isobutyl isobutyrate) is used, the solubility of the ester solvent to 2,2,4,4-tetramethyl-1,3-cyclobutanedione is relatively low. , the 2,2,4,4-tetramethyl-1,3-cyclobutanedione formed after the dimerization reaction tends to precipitate out. Therefore, after the dimerization reaction is completed, a process (such as a recrystallization process and/or a filtration process) can be used to collect the solid 2,2,4,4-tetramethyl-1,3-cyclobutanedione, and use a solvent Washing is performed to obtain high-purity 2,2,4,4-tetramethyl-1,3-cyclobutanedione (purity can be greater than 99wt%).
根據本揭露實施例,在對二甲基烯酮進行二聚反應後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法50可更包含:將步驟24所得之2,2,4,4-四甲基-1,3-環丁烷二酮與一溶劑混合得到一溶液(步驟26),以及將步驟26所得之該溶液與氫氣進行氫化反應,得到一第三混合物,其中該第三混合物包含2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、以及溶劑(步驟28)。根據本揭露實施例,該溶液的固含量可為5wt%至20 wt%。根據本揭露實施例,該包含2,2,4,4-四甲基-1,3-環丁烷二酮的溶液可在一觸媒存在下與氫氣進行氫化反應,以形成2,2,4,4-四甲基-1,3-環丁烷二醇(2,2,4,4-Tetramethyl-1,3-cyclobutanediol、CBDO )。本揭露對於所使用的觸媒並無限制,可為習知用於氫化2,2,4,4-四甲基-1,3-環丁烷二酮所使用的觸媒。根據本揭露實施例,氫化反應的氫氣壓力可介於10bar至120bar之間,例如介於30bar至70bar之間。根據本揭露實施例,該氫化反應的溫度可為50℃至80℃、以及氫化反應的壓力可為1MPa至10MPa。表1顯示分別在60℃以及135℃下(其他反應條件相同)對2,2,4,4-四甲基-1,3-環丁烷二酮進行氫化反應所得各產物的選擇率。According to an embodiment of the present disclosure, after the dimerization reaction of dimethyl ketene, the
表1
由表1可得知,氫化速率雖然隨著溫度上升而增加,然而若氫化製程的溫度過高,則會增加副產物(環酮類產物、開環酮類產物、或2,2,4-三甲基-1,3-戊二醇(2,2,4-Trimethyl-1,3-pentanediol,TMPD)的比例。It can be seen from Table 1 that although the hydrogenation rate increases as the temperature rises, if the temperature of the hydrogenation process is too high, by-products (cyclic ketone products, ring-opening ketone products, or 2,2,4- The ratio of trimethyl-1,3-pentanediol (2,2,4-Trimethyl-1,3-pentanediol, TMPD).
根據本揭露實施例,在對2,2,4,4-四甲基-1,3-環丁烷二酮進行氫化反應後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法50可更包含:對第三混合物進行一第二純化製程,得到2,2,4,4-四甲基-1,3-環丁烷二醇(步驟30)。根據本揭露實施例,該第二純化製程可包含一相分離製程,以回收氫氣並得到一包含2,2,4,4-四甲基-1,3-環丁烷二醇以及溶劑的溶液。根據本揭露實施例,該第二純化製程可更包含一蒸餾製程,以回收溶劑及移除副產物(環酮副產物、開環酮類副產物),得到2,2,4,4-四甲基-1,3-環丁烷二醇。According to an embodiment of the present disclosure, after the hydrogenation reaction of 2,2,4,4-tetramethyl-1,3-cyclobutanedione, the method for preparing a compound using isobutyric acid and acetic anhydride described in the
根據本揭露實施例,本揭露亦提供一種利用異丁酸及乙酸酐製備化合物之裝置。第3圖係為本揭露實施例所述利用異丁酸及乙酸酐製備化合物之裝置100的示意圖。According to an embodiment of the present disclosure, the present disclosure also provides an apparatus for preparing a compound by using isobutyric acid and acetic anhydride. FIG. 3 is a schematic diagram of the
如第3圖所示,該利用異丁酸及乙酸酐製備化合物之裝置100可包含一進料單元110、一第一反應單元115、一第一純化單元120、一裂解單元125、以及一氣液分離單元130。該進料單元110與該第一反應單元115連接,以將異丁酸及乙酸酐由進料單元110導入該第一反應單元115。在第一反應單元115中,該異丁酸在該第一反應單元與乙酸酐反應得到一第一混合物,其中該第一混合物包含異丁酸酐及醋酸。根據本揭露實施例,該第一反應單元115可例如為一連續式攪拌反應器。該第一反應單元115與該第一純化單元120連接,以將該第一混合物導入該第一純化單元120。該第一混合物可在該第一純化單元中進行一第一純化製程,得到異丁酸酐以及醋酸。根據本揭露實施例,該第一純化單元120可包含一蒸餾塔。該第一純化單元120與該裂解單元125連接,以將異丁酸酐導入該裂解單元125。異丁酸酐在該裂解單元進行一裂解製程得到一第二混合物,其中第二混合物包含二甲基烯酮 、異丁酸與異丁酸酐。根據本揭露實施例,該裂解單元125可包含一蒸發器以及一裂解反應器(未圖示)。由純化單元120供應的異丁酸酐經過蒸發器預熱後導入該裂解反應器進行高溫裂解反應。該裂解單元125與該氣液分離單元130連接,以將第二混合物導入該氣液分離單元130,其中該第二混合物在氣液分離單元130分離成一二甲基烯酮氣體及一液體,其中液體包含異丁酸與異丁酸酐,其中該進料單元110與該氣液分離單元130連接,以將該液體導入該進料單元110。根據本揭露實施例,該進料單元110可進一步將該液體導入該第一反應單元115以與乙酸酐反應。根據本揭露實施例,該利用異丁酸及乙酸酐製備化合物之裝置100可更包含一醋酸收集單元135,其中該醋酸收集單元135與該第一純化單元120連接,用以收集由第一純化單元120所分離的醋酸。As shown in FIG. 3, the
第4圖係為本揭露實施例所述利用異丁酸及乙酸酐製備化合物之裝置200的示意圖。根據本揭露實施例,本揭露實施例所述利用異丁酸及乙酸酐製備化合物之裝置除了該進料單元110、該第一反應單元115、該第一純化單元120、該裂解單元125、以及該氣液分離單元130外,可更包含一第二反應單元140、一抽吸單元145、一溶劑供給單元150、一固液分離單元155、一氫化單元160、一第二純化單元165、以及一收集單元170之至少一者。FIG. 4 is a schematic diagram of an
根據本揭露實施例,如第4圖所示,為使二甲基烯酮進行二聚反應形成2,2,4,4-四甲基-1,3-環丁烷二酮,該氣液分離單元130可與該第二反應單元140連接,以將該二甲基烯酮氣體導入該第二反應單元140。該二甲基烯酮氣體在該第二反應單元140中進行二聚反應形成2,2,4,4-四甲基-1,3-環丁烷二酮。According to an embodiment of the present disclosure, as shown in FIG. 4 , in order to dimerize dimethylketene to form 2,2,4,4-tetramethyl-1,3-cyclobutanedione, the gas-liquid The
根據本揭露實施例,為使第二反應單元140能在5℃至25℃及常壓(例如750 Torr至770 Torr)下充分接收由該氣液分離單元130所得之二甲基烯酮氣體,本揭露所述利用異丁酸及乙酸酐製備化合物之裝置200可更包含一抽吸單元145。該第二反應單元140藉由該抽吸單元與該氣液分離單元130連接,其中該抽吸單元145可對該二甲基烯酮氣體進行一噴射抽吸製程,使由氣液分離單元130所分離出的二甲基烯酮氣體可被第二反應單元140接收。According to the embodiment of the present disclosure, in order to enable the
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之裝置200可更包含一溶劑供給單元150,其中該溶劑供給單元150與該抽吸單元145連接,以供應該抽吸單元145一溶劑進行該噴射抽吸製程。在進行噴射抽吸製程中,該溶劑可溶解(吸收)二甲基烯酮,形成含二甲基烯酮的酯類溶液。根據本揭露實施例,由第二反應單元140所收集的二甲基烯酮氣體亦可進一步溶解於該溶劑中,形成含二甲基烯酮的酯類溶液。According to an embodiment of the present disclosure, the
根據本揭露實施例,可藉由該第二反應單元140對二甲基烯酮進行二聚反應,得到2,2,4,4-四甲基-1,3-環丁烷二酮(2,2,4,4-Tetramethyl-1,3-cyclobutanedione,TMCD)。根據本揭露實施例,在該第二反應單元140中,該二聚反應的溫度可控制在20℃至75℃之間,以降低副產物(例如寡聚物)生成及提高2,2,4,4-四甲基-1,3-環丁烷二酮的選擇率。根據本揭露實施例,惰性氣體(如氮氣或氬氣)可被導入第二反應單元140中,使得二聚反應係在惰性氣體環境下進行。根據本揭露實施例,該第二反應單元140可包含一反應器(例如連續式攪拌反應器)以及一組結晶器(未圖示)。由該氣液分離單元130供應的二甲基烯酮經由攪拌反應器進行二聚反應,所得之2,2,4,4-四甲基-1,3-環丁二酮(TMCD)再經由結晶器形成2,2,4,4-四甲基-1,3-環丁二酮固體。According to an embodiment of the present disclosure, the
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之裝置200可更包含一固液分離單元155,其中該第二反應單元140與該固液分離單元155連接,以將由該第二反應單元140所得之產物(包含溶劑及2,2,4,4-四甲基-1,3-環丁烷二酮固體)導入該固液分離單元155。藉由該固液分離單元155,可使2,2,4,4-四甲基-1,3-環丁烷二酮以固體形式與溶劑分離。根據本揭露實施例,該固液分離單元155可與該溶劑供給單元150連接,以利用溶劑供給單元150回收該溶劑。根據本揭露實施例,該溶劑供給單元150可將回收該溶劑純化,並進行再利用。According to an embodiment of the present disclosure, the
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之裝置200可更包含一氫化單元160,其中該固液分離單元155與該氫化單元160連接,以將2,2,4,4-四甲基-1,3-環丁烷二酮導入該氫化單元160中。根據本揭露實施例,該溶劑供給單元150可與該氫化單元連接,以將溶劑導入氫化單元160。2,2,4,4-四甲基-1,3-環丁烷二酮可在氫化單元160進行氫化反應,得到一第三混合物,其中該第三混合物包含2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、以及溶劑。根據本揭露實施例,該氫化單元160可包含一攪拌器、一氣體供應器、以及一反應器。該攪拌器可將2,2,4,4-四甲基-1,3-環丁烷二酮與與溶劑混合形成一溶液,並將該溶液導入該反應器。該氣體供應器可提供氣體(例如氫氣、或氫氣及載氣)至該反應器中,使得2,2,4,4-四甲基-1,3-環丁烷二酮在氫氣存在下在反應器內進行氫化反應。According to an embodiment of the present disclosure, the
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之裝置200可更包含一第二純化單元165,其中該氫化單元160與該第二純化單元165連接,以將第三混合物導入第二純化單元165。該第三混合物可在第二純化單元進行一純化製程,以將2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、及溶劑分離。根據本揭露實施例,該第二純化單元165可與該溶劑供給單元150連接,以利用溶劑供給單元150回收該溶劑。根據本揭露實施例,第二純化單元165可將未反應的氫氣導入該氫化單元160中。根據本揭露實施例,該第二純化單元165可包含一分離器及一蒸餾塔(未圖示)。該分離器可將氣體(例如包含氫氣、以及載氣)及液體(例如包含2,2,4,4-四甲基-1,3-環丁烷二醇、溶劑、及副產物)分離,並將氣體導入氫化單元160,以及將液體導入該蒸餾塔。該蒸餾塔可將2,2,4,4-四甲基-1,3-環丁烷二醇、及溶劑由液體中分離,並將溶劑導入溶劑供給單元150。根據本揭露實施例,該溶劑供給單元可包含一純化部件及一儲存部件(未圖示)。該純化部件可將由該固液分離單元155及第二純化單元所回收的液體加以純化,以將該溶劑導入該抽吸單元145及該氫化單元160,進行再利用。According to an embodiment of the present disclosure, the
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之裝置200可更包含一收集單元170, 其中該收集單元170與該第二純化單元165連接,用以收集2,2,4,4-四甲基-1,3-環丁烷二醇。According to an embodiment of the present disclosure, the
根據本揭露實施例,本揭露提供一種利用異丁酸及乙酸酐製備化合物之方法。該利用異丁酸及乙酸酐製備化合物之方法可使用第3圖或第4圖所示之裝置進行。第5圖為本揭露一實施例所述利用異丁酸及乙酸酐製備化合物之方法300之步驟流程圖。該方法300可使用第3圖所示之裝置進行。According to an embodiment of the present disclosure, the present disclosure provides a method for preparing a compound using isobutyric acid and acetic anhydride. The method for preparing the compound using isobutyric acid and acetic anhydride can be carried out using the apparatus shown in FIG. 3 or FIG. 4 . FIG. 5 is a flow chart showing the steps of a
根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法300包含以下步驟。將異丁酸及乙酸酐由該進料單元110導入至該第一反應單元115內(步驟310)。將異丁酸及乙酸酐在該第一反應單元中進行一反應(例如酯化反應),得到一第一混合物,其中該第一混合物包含異丁酸酐及醋酸(步驟320)。根據本揭露實施例,在進行反應前,可將異丁酸及乙酸酐充份混合。接著,將第一混合物導入該第一純化單元120以對該第一混合物進行一第一純化製程,得到異丁酸酐以及醋酸(步驟330)。根據本揭露實施例,該第一純化製程可包含一攪拌製程及一蒸餾製程。在對該第一混合物進行蒸餾製程前,對該第一混合物進行攪拌製程。根據本揭露實施例,在進行該第一純化製程後,可以一醋酸收集單元135收集該醋酸。接著,將異丁酸酐由第一純化單元120導入一裂解單元125以對異丁酸酐進行一裂解製程,得到一第二混合物,其中第二混合物包含二甲基烯酮 、異丁酸與異丁酸酐(步驟340)。在該裂解製程中,異丁酸酐可先在280℃至350℃下進行預熱,接著加熱異丁酸酐到400℃至500℃之間以熱裂解異丁酸酐。根據本揭露實施例,該裂解製程的壓力可介於60 Torr至120 Torr之間,製程的時間可介於0.01秒至1秒之間,且異丁酸酐的轉化率可介於50%至70%之間。根據本揭露實施例,可搭配載氣(例如氬氣或氮氣)與異丁酸酐的氣體混合後再進行該裂解製程。接著,將第二混合物導入一氣液分離單元130以對該第二混合物進行一氣液分離製程,得到二甲基烯酮氣體及一液體,其中該液體包含異丁酸與異丁酸酐(步驟350)。According to an embodiment of the present disclosure, the
根據本揭露實施例,在進行氣液分離製程後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法300可更包含:將該液體導入該進料單元110(步驟360)。根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法300可更包含:將液體由該進料單元110導入該第一反應單元115,以使該液體中的異丁酸與乙酸酐在該第一反應單元115中進行反應。According to an embodiment of the present disclosure, after the gas-liquid separation process is performed, the
第6A圖及第6B圖為本揭露某些實施例所述利用異丁酸及乙酸酐製備化合物之方法400之步驟流程圖。該方法400可使用第4圖所示之裝置進行。FIGS. 6A and 6B are flow diagrams of the steps of a
根據本揭露實施例,在以該氣液分離單元130對該第二混合物進行氣液分離製程後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法400可包含:利用一抽吸單元145對二甲基烯酮氣體進行一噴射抽吸製程,以將二甲基烯酮氣體由該氣液分離單元130導入該第二反應單元140(步驟410)。藉由該噴射抽吸製程,本揭露所述該第二反應單元可在5℃至25℃以及750 Torr至770 Torr(即常壓)的環境下收集該二甲基烯酮氣體。根據本揭露實施例,該噴射抽吸製程的壓力差來自於溶劑的流速,而所使用的溶劑可為酯類溶劑,例如異丁酸異丁酯、丙酸乙酯、或乙酸辛酯。根據本揭露實施例,在進行噴射抽吸製程中,該溶劑可溶解(吸收)二甲基烯酮,形成含二甲基烯酮的酯類溶液。根據本揭露實施例,該含二甲基烯酮的酯類溶液的二甲基烯酮濃度可為10wt%至70wt%,以該二甲基烯酮及溶劑的總重為基準。根據本揭露實施例,一溶劑供給單元150可與該抽吸單元145連接,以供應該抽吸單元145一溶劑進行該噴射抽吸製程。在進行噴射抽吸製程中,該溶劑可溶解(吸收)二甲基烯酮,形成含二甲基烯酮的酯類溶液。根據本揭露實施例,由該第二反應單元140所收集的二甲基烯酮氣體亦可進一步溶解於該溶劑中,形成含二甲基烯酮的酯類溶液。According to an embodiment of the present disclosure, after the gas-
根據本揭露實施例,在將二甲基烯酮導入該第二反應單元140後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法400可包含:將二甲基烯酮氣體在該第二反應單元140中進行二聚反應,形成2,2,4,4-四甲基-1,3-環丁烷二酮(步驟420)。根據本揭露實施例,該第二反應單元140的溫度可控制在20℃至75℃。換言之,該二聚反應係在20℃至75℃下進行。若反應溫度過低,則反應過慢,需要增加反應時間。若反應溫度過高,則在二聚反應中會產生聚酯或聚酮的寡聚物,降低2,2,4,4-四甲基-1,3-環丁烷二酮產率及純度。根據本揭露實施例,該二聚反應的時間可介於2小時至24小時之間。此外,根據本揭露實施例,惰性氣體(如氮氣或氬氣)可被導入該第二反應單元140,使得該二聚反應在惰性氣體環境下進行。根據本揭露實施例,若使用酯類溶劑(例如異丁酸異丁酯),由於酯類溶劑對2,2,4,4-四甲基-1,3-環丁二酮的溶解度較低,二聚反應後所形成的2,2,4,4-四甲基-1,3-環丁二酮會傾向析出。因此,待二聚反應結束後,可利用一製程(例如再結晶製程及/或過濾製程)收集2,2,4,4-四甲基-1,3-環丁二酮固體,並以溶劑進行清洗,得到高純度的2,2,4,4-四甲基-1,3-環丁二酮(純度可大於96wt%)。According to an embodiment of the present disclosure, after introducing dimethyl ketene into the
根據本揭露實施例,在對二甲基烯酮進行二聚反應後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法400可包含:將二聚反應之產物(包含2,2,4,4-四甲基-1,3-環丁烷二酮及溶劑)由第二反應單元140導入一固液分離單元155,進行一固液分離製程(步驟430)。詳細地說,在該固液分離單元155中,該二聚反應之產物(包含2,2,4,4-四甲基-1,3-環丁烷二酮及溶劑)可經由該固液分離製程,使2,2,4,4-四甲基-1,3-環丁烷二酮以固體形式與溶劑分離。根據本揭露實施例,該固液分離單元155可與該溶劑供給單元150連接,因此可將該固液分離單元155分離的液體導入溶劑供給單元150回收,使得該溶劑可經該溶劑供給單元150純化並再利用。According to an embodiment of the present disclosure, after the dimerization of dimethylketene, the
根據本揭露實施例,在進行固液分離製程後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法400可更包含:將2,2,4,4-四甲基-1,3-環丁烷二酮以及溶劑導入一氫化單元160內並進行混合得到一溶液(步驟440)。接著,利用該氫化單元160對所得之溶液進行氫化反應,得到一第三混合物,其中該第三混合物包含2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、以及溶劑 (步驟450)。根據本揭露實施例,該2,2,4,4-四甲基-1,3-環丁烷二酮可由該固液分離單元155導入該氫化單元160內,而該溶劑可由溶劑供給單元150導入該氫化單元160內。根據本揭露實施例,一氣體(例如氫氣、或氫氣及載氣)可導入該氫化單元160內,使得2,2,4,4-四甲基-1,3-環丁烷二酮與氫氣進行氫化反應。該溶液的固含量可為5wt%至20 wt%。此外,根據本揭露實施例,該包含2,2,4,4-四甲基-1,3-環丁烷二酮的溶液可在一觸媒存在下與氫氣進行氫化反應,以形成2,2,4,4-四甲基-1,3-環丁烷二醇。根據本揭露實施例,氫化反應的氫氣壓力可介於10bar至120bar之間,例如介於30bar至70bar之間。根據本揭露實施例,該氫化反應的溫度可為50℃至80℃、以及氫化反應的壓力可為1MPa至10MPa。由於氫化反應係在相對低溫下進行,如此一來可大幅降低副產物(例如環酮副產物、開環酮類副產物、或2,2,4-三甲基-1,3-戊二醇)的生成。According to an embodiment of the present disclosure, after the solid-liquid separation process is performed, the
根據本揭露實施例,在進行該氫化反應後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法400可更包含:將第三混合物導入一第二純化單元165以對該第三混合物進行一第二純化製程,得到2,2,4,4-四甲基-1,3-環丁烷二醇、氫氣、及溶劑(步驟460)。根據本揭露實施例,該第二純化製程可包含一相分離製程,以回收氫氣並得到一包含2,2,4,4-四甲基-1,3-環丁烷二醇以及溶劑的溶液。根據本揭露實施例,該第二純化製程可更包含一蒸餾製程,以回收溶劑及移除副產物(環酮副產物、開環酮類副產物),得到2,2,4,4-四甲基-1,3-環丁烷二醇。根據本揭露實施例,在進行該第二純化製程後,可利用該溶劑供給單元150回收由該第二純化製程所分離的溶劑,且可將由該第二純化製程所分離的氫氣由該第二純化單元165導入該第二反應單元160中。According to an embodiment of the present disclosure, after the hydrogenation reaction is performed, the
根據本揭露實施例,在進行該第二純化製程後,本揭露所述利用異丁酸及乙酸酐製備化合物之方法400可更包含:將第二純化製程所分離的2,2,4,4-四甲基-1,3-環丁烷二醇導入一收集單元170(步驟470)。According to an embodiment of the present disclosure, after the second purification process is performed, the
基於上述,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置可將異丁酸酐經裂解後所得副產物(例如異丁酸)以及未反應的起始物(例如異丁酸酐)再利用。此外,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置可利用一噴射抽吸製程收集所得之二甲基烯酮氣體,因此可大幅降低能耗及提高二甲基烯酮的收率。再者,根據本揭露實施例,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置,係在相對低溫(例如低於75℃)下對二甲基烯酮進行二聚反應形成2,2,4,4-四甲基-1,3-環丁烷二酮。如此一來,可降低副產物(例如寡聚物)生成,提高2,2,4,4-四甲基-1,3-環丁烷二酮的選擇率(根據本揭露實施例,選擇率可高達99%以上)。另一方面,本揭露所述利用異丁酸及乙酸酐製備化合物之方法及裝置,係在相對低溫(例如低於80℃)下對2,2,4,4-四甲基-1,3-環丁烷二酮進行氫化反應。如此一來,可大幅降低副產物(例如環酮副產物、開環酮類副產物、或2,2,4-三甲基-1,3-戊二醇)的生成。Based on the above, the method and apparatus for preparing compounds using isobutyric acid and acetic anhydride described in the present disclosure can be used to obtain by-products (such as isobutyric acid) and unreacted starting materials (such as isobutyric anhydride) obtained after isobutyric anhydride is cleaved Reuse. In addition, the method and device for preparing compounds using isobutyric acid and acetic anhydride described in the present disclosure can utilize a jet suction process to collect the obtained dimethylketene gas, thereby greatly reducing energy consumption and improving the dimethylketene production rate. yield. Furthermore, according to an embodiment of the present disclosure, the method and device for preparing a compound using isobutyric acid and acetic anhydride described in the present disclosure are formed by dimerizing dimethyl ketene at a relatively low temperature (eg, below 75° C.). 2,2,4,4-Tetramethyl-1,3-cyclobutanedione. In this way, the generation of by-products (such as oligomers) can be reduced, and the selectivity of 2,2,4,4-tetramethyl-1,3-cyclobutanedione can be improved (according to the embodiment of the present disclosure, the selectivity can be as high as more than 99%). On the other hand, the method and apparatus for preparing compounds using isobutyric acid and acetic anhydride described in the present disclosure is a relatively low temperature (eg lower than 80°C) for 2,2,4,4-tetramethyl-1,3 - Cyclobutanedione undergoes hydrogenation. In this way, the generation of by-products (eg, by-products of cyclic ketones, by-products of ring-opened ketones, or 2,2,4-trimethyl-1,3-pentanediol) can be greatly reduced.
雖然本揭露已以數個實施例揭露如上,然其並非用以限定本揭露,任何本技術領域中具有通常知識者,在不脫離本揭露之精神和範圍內,當可作任意之更動與潤飾,因此本揭露之保護範圍當視後附之申請專利範圍所界定者為準。Although the present disclosure has been disclosed above with several embodiments, it is not intended to limit the present disclosure. Anyone with ordinary knowledge in the technical field may make any changes and modifications without departing from the spirit and scope of the present disclosure. Therefore, the scope of protection of this disclosure should be determined by the scope of the appended patent application.
10、50、300、400:利用異丁酸及乙酸酐製備化合物之方法
12、14、16、18、20、22、24、26、28、30、310、320、330、340、350、360、410、420、430、440、450、460、470:步驟
100、200:利用異丁酸及乙酸酐製備化合物之裝置
110:進料單元
115:第一反應單元
120:第一純化單元
125:裂解單元
130:氣液分離單元
135:醋酸收集單元
140:第二反應單元
145:抽吸單元
150:溶劑供給單元
155:固液分離單元
160:氫化單元
165:第二純化單元
170:收集單元
10, 50, 300, 400: the method of utilizing isobutyric acid and acetic anhydride to prepare
第1圖為本揭露一實施例所述利用異丁酸及乙酸酐製備化合物之方法10之步驟流程圖。
第2圖為本揭露某些實施例所述利用異丁酸及乙酸酐製備化合物之方法50之步驟流程圖。
第3圖係為本揭露一實施例所述利用異丁酸及乙酸酐製備化合物之裝置100的示意圖。
第4圖係為本揭露某些實施例所述利用異丁酸及乙酸酐製備化合物之裝置200的示意圖。
第5圖為本揭露某些實施例所述利用異丁酸及乙酸酐製備化合物之方法300之步驟流程圖。
第6A及6B圖為本揭露某些實施例所述利用異丁酸及乙酸酐製備化合物之方法400之步驟流程圖。
FIG. 1 is a flow chart showing the steps of a
10:利用異丁酸及乙酸酐製備化合物之方法 10: Utilize isobutyric acid and acetic anhydride to prepare the method for compound
12、14、16、18、20:步驟 12, 14, 16, 18, 20: Steps
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