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1. 发明授权

US4227008A Process for preparing aromatic urethanes 失效
标题翻译：制备芳香族聚氨酯的方法
公开(公告)号：US4227008A
公开(公告)日：1980-10-07
申请号：US927779
申请日：1978-07-25
申请人： Katsuharu Miyata , Makoto Aiga , Seiji Hasegawa
发明人： Katsuharu Miyata , Makoto Aiga , Seiji Hasegawa
IPC分类号： C07C271/06 , C07C125/04
CPC分类号： C07C271/06
摘要： Aromatic urethanes can be produced by interacting an aromatic primary amino compound having a nitro group, a nitroso group or a carbamate group, an organic compound having at least one hydroxyl group, and carbon monoxide in the presence of a catalytic system composed of a platinum group metal and/or a compound thereof serving as catalyst and a Lewis acid and/or a compound thereof as promoter under high temperature and high pressure conditions. For instance, the interaction of 2-amino-4-nitrotoluene, ethanol and carbon monoxide in the presence of palladium chloride and a ferrous chloride-pyridine complex under high temperature and high pressure conditions can yield 2,4-diethylcarbamatetoluene.
摘要翻译：芳族聚氨酯可以通过在具有硝基，亚硝基或氨基甲酸酯基团的芳族伯氨基化合物，具有至少一个羟基的有机化合物和一氧化碳的相互作用下，在由铂族组成的催化体系金属和/或其化合物作为催化剂，路易斯酸和/或其化合物作为助催化剂在高温高压条件下进行。例如，在氯化钯和氯化亚铁 - 吡啶络合物的存在下，在高温和高压条件下，2-氨基-4-硝基甲苯，乙醇和一氧化碳的相互作用可以产生2,4-二乙基氨基甲酸甲酯。

2. 发明授权

US4178455A Process for preparing aromatic urethanes 失效
标题翻译：制备芳香族聚氨酯的方法
公开(公告)号：US4178455A
公开(公告)日：1979-12-11
申请号：US925543
申请日：1978-07-17
申请人： Yutaka Hirai , Katsuharu Miyata , Makoto Aiga , Seiji Hasegawa
发明人： Yutaka Hirai , Katsuharu Miyata , Makoto Aiga , Seiji Hasegawa
IPC分类号： C07C271/06 , C07C125/04
CPC分类号： C07C271/06
摘要： In a process for preparing an aromatic urethane which comprises reacting an aromatic nitro compound, an organic compound containing at least one hydroxyl group, and carbon monoxide at elevated temperature and pressure in the presence of a catalytic system composed of a catalyst consisting of a platinum metal, a platinum metal compound, and/or a platinum metal compound-containing compound and a promoter consisting of a Lewis acid and/or a Lewis acid-containing compound, an organic primary amino compound, a urea compound, a biuret compound, an allophanate compound, or a mixture thereof is added to the reaction system whereby the reaction rate is increased and the yield of the desired product is enhanced. For example, 2,4-diethylcarbamatetoluene can be prepared in quantitatively high yield by reacting 2,4-dinitrotoluene, ethanol, carbon monoxide, and a small amount of aminonitrotoluene at elevated temperature and pressure in the presence of palladium chloride and ferrous chloride-pyridine complex.
摘要翻译：在制备芳族氨基甲酸酯的方法中，包括使芳族硝基化合物，含有至少一个羟基的有机化合物和一氧化碳在升高的温度和压力下，在由铂金属，铂金属化合物和/或含铂金属化合物的化合物和由路易斯酸和/或路易斯酸化合物，有机伯氨基化合物，脲化合物，缩二脲化合物，脲基甲酸酯组成的促进剂化合物或其混合物加入到反应体系中，由此提高反应速率并提高所需产物的产率。例如，2,4-二乙基氨基甲酸甲酯可以通过在升高的温度和压力下，在氯化钯和氯化亚铁 - 吡啶存在下，使2,4-二硝基甲苯，乙醇，一氧化碳和少量的氨基硝基甲苯反应，以定量高的产率制备复杂。

3. 发明授权

US4186269A Process for producing an aromatic urethane 失效
标题翻译：芳香族聚氨酯的制造方法
公开(公告)号：US4186269A
公开(公告)日：1980-01-29
申请号：US645712
申请日：1975-12-31
申请人： Yutaka Hirai , Katsuharu Miyate , Makoto Aiga
发明人： Yutaka Hirai , Katsuharu Miyate , Makoto Aiga
IPC分类号： B01J21/18 , B01J23/40 , B01J23/44 , B01J31/02 , B01J31/30 , B01J31/40 , C07C125/06
CPC分类号： B01J31/4038 , B01J23/40 , B01J31/181 , B01J31/2404 , B01J31/30 , B01J31/4046 , B01J31/4053 , C07C269/04 , B01J21/18 , B01J23/44 , B01J2531/821 , B01J2531/822 , B01J2531/824 , Y02P20/584
摘要： An aromatic urethane is obtained at high yield without involving corrosion of a stainless steel reactor by interacting an aromatic nitro compound, an organic compound having at least one hydroxyl group therein and carbon monoxide in the presence of a catalyst composed of (1) palladium, ruthenium, rhodium or compounds thereof, (2) a Lewis acid, and (3) a tertiary amine. For instance, 2,4-dinitrotoluene, ethanol and carbon monoxide placed in a SUS-32 reactor are interacted in the presence of a catalyst composed of (1) 5% palladium on carbon, (2) ferric chloride, and (3) pyridine to obtain 2,4-diethyldicarbamatetoluene without corrosion of the reactor. After completion of the reaction, the catalyst and reaction product are separated from the reaction system; e.g., the insoluble catalyst is first separated and then the reaction solution is cooled down, e.g., to room temperature, to separate the reaction product as crystals, followed by separation of the crystals by filtration. Then, the reaction may be repeated by adding fresh 2,4-dinitrotoluene and ethanol and the separated catalyst to the resultant fitrate under pressurized conditions of a carbon monoxide atmosphere. By repeating the reaction in this manner, 2,4-diethyldicarbamatetoluene with a purity of 98% can be obtained at a yield of 90%.
摘要翻译：通过在由（1）钯，钌组成的催化剂存在下，通过使芳香族硝基化合物，其中具有至少一个羟基的有机化合物与一氧化碳相互作用而使不锈钢反应器的腐蚀得到高收率的芳族聚氨酯，铑或其化合物，（2）路易斯酸，和（3）叔胺。例如，放置在SUS-32反应器中的2,4-二硝基甲苯，乙醇和一氧化碳在由（1）5％钯碳，（2）氯化铁和（3）吡啶组成的催化剂存在下相互作用得到2,4-二乙基氨基甲酸甲酯，没有反应器的腐蚀。反应完成后，将催化剂和反应产物与反应体系分离; 例如，首先分离不溶性催化剂，然后将反应溶液冷却至例如室温，将反应产物分离成晶体，然后通过过滤分离晶体。然后，可以通过在一氧化碳气氛的加压条件下，将新鲜的2,4-二硝基甲苯和乙醇加入到合适的配料中，并分离出催化剂，从而重复反应。通过以这种方式重复反应，可以以90％的收率获得纯度为98％的2,4-二乙基氨基甲酸甲酯。

4. 发明授权

US4922005A Preparation process of hexamethylene 失效
标题翻译：六亚甲基的制备方法
公开(公告)号：US4922005A
公开(公告)日：1990-05-01
申请号：US797457
申请日：1985-11-13
申请人： Masanobu Ajioka , Makoto Aiga , Masafumi Kataita , Akihiro Tamaki
发明人： Masanobu Ajioka , Makoto Aiga , Masafumi Kataita , Akihiro Tamaki
IPC分类号： C07C263/10
CPC分类号： C07C263/10
摘要： Hexamethylene diisocyanate (HDI) is prepared by introducing a hexamethylenediamine (HDA) solution and an equivalent amount or more of hydrogen chloride gas simultaneously into a turbulent zone in the vicinity of an agitating blade in an inert organic solvent held under agitation within a tank-shaped reactor and allowing them to undergo a successive salt-forming reaction so as to obtain a high-concentration slurry of hexamethylenediamine hydrochloride (HDA.multidot.HCl) and then reacting the slurry with phosgene. The phosgenation is effected by charging an HDA.multidot.HCl slurry of a high concentration, such as that obtained by the above process, into a tank-shaped reactor held under a pressure above the atmosphere pressure but below 5 kg/cm.sup.2 G and controlling the amount of phosgene, which is to be blown into the reactor, at a level 1-18 molar times per hour the total amount of HDA.multidot.HCl and HDI in the reaction mixture. In a preferred embodiment of the phosgenation, the phosgenation reaction is effected in a continuous two-step tank-shaped reactor while controlling the degree of conversion in the first step within 70-95%. This is a rationalized preparation process of hexamethylene diisocyanate since it requires a shorter overall phosgenation time.
摘要翻译：六亚甲基二异氰酸酯（HDI）是通过将六亚甲基二胺（HDA）溶液和等当量的氯化氢气体同时引入搅拌叶片附近的湍流区域，在惰性有机溶剂中保持搅拌状态的罐形反应器中并使它们经历连续的成盐反应，以获得六亚甲基二胺盐酸盐（HDAxHCl）的高浓度浆料，然后使该浆料与光气反应。光气化是通过将高浓度的HDAxHCl浆料（例如通过上述方法获得的）输送到保持在高于大气压力但低于5kg / cm2G的压力下的罐形反应器中并控制光气的量来实现的，其将以每小时1-18摩尔倍的速率吹入反应器，反应混合物中的HDAxHCl和HDI的总量。在光气化的优选实施方案中，光气化反应在连续的两步槽形反应器中进行，同时控制第一步中的转化率在70-95％之内。这是六亚甲基二异氰酸酯的合理制备方法，因为它需要更短的整体光气化时间。

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