公开(公告)号：US20090287023A1

公开(公告)日：2009-11-19

申请号：US12097974

申请日：2006-12-25

申请人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

发明人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

IPC分类号： C07C209/24

CPC分类号： C07C209/62 ,  C07C209/08 ,  C07C211/21 ,  C07C211/28

摘要： Disclosed is a method for producing a primary amine compound represented by the formula (2) below, which is characterized in that a halogen compound represented by the formula (1) below, ammonia and formaldehyde are reacted with each other, and then the thus-obtained reaction product is [1] brought into contact with an aqueous solution of an acid or [2] reacted with a hydroxylamine under acidic conditions. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product. (1) (In the formula, R1 and R2 independently represent a hydrogen atom, a C1-C5 alkyl group which may be substituted by a halogen atom or the like, a C1-C5 alkoxy group which may be substituted by a halogen atom, a cyano group, a C2-C11 alkenyl group or a phenyl group or the like; R3 represents a hydrogen atom, a linear or branched C1-C5 alkyl group or a cyano group; and X represents a halogen atom.) (2) (In the formula, R1, R2 and R3 are as defined above.)

摘要翻译： 公开了下述式（2）表示的伯胺化合物的制造方法，其特征在于，将下式（1）表示的卤素化合物与氨和甲醛反应， 得到的反应产物[1]在酸性条件下与酸的水溶液或[2]与羟胺反应。 通过这种方法，可以通过使用低成本氨同时抑制作为副产物的仲胺的生产，商业上有利地生产伯胺化合物。 （1）（式中，R 1和R 2各自独立地表示氢原子，可被卤素原子等取代的C1〜C5烷基，可被卤素原子取代的C1〜C5烷氧基， 氰基，C 2 -C 11烯基或苯基等; R 3表示氢原子，直链或支链C 1 -C 5烷基或氰基; X表示卤素原子）（2）（ 在式中，R 1，R 2和R 3如上所定义。）

公开(公告)号：US07652170B2

公开(公告)日：2010-01-26

申请号：US12097974

申请日：2006-12-25

申请人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

发明人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

IPC分类号： C07C209/08

CPC分类号： C07C209/62 ,  C07C209/08 ,  C07C211/21 ,  C07C211/28

摘要： Disclosed is a method for producing a primary amine compound represented by the formula (2) below, which is characterized in that a halogen compound represented by the formula (1) below, ammonia and formaldehyde are reacted with each other, and then the thus-obtained reaction product is [1] brought into contact with an aqueous solution of an acid or [2] reacted with a hydroxylamine under acidic conditions. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product. (1) (In the formula, R1 and R2 independently represent a hydrogen atom, a C1-C5 alkyl group which may be substituted by a halogen atom or the like, a C1-C5 alkoxy group which may be substituted by a halogen atom, a cyano group, a C2-C11 alkenyl group or a phenyl group or the like; R3 represents a hydrogen atom, a linear or branched C1-C5 alkyl group or a cyano group; and X represents a halogen atom.) (2) (In the formula, R1, R2 and R3 are as defined above.)

摘要翻译： 公开了下述式（2）表示的伯胺化合物的制造方法，其特征在于，将下式（1）表示的卤素化合物与氨和甲醛反应， 得到的反应产物[1]在酸性条件下与酸的水溶液或[2]与羟胺反应。 通过这种方法，可以通过使用低成本氨同时抑制作为副产物的仲胺的生产，商业上有利地生产伯胺化合物。 （1）（式中，R 1和R 2各自独立地表示氢原子，可被卤素原子等取代的C1〜C5烷基，可被卤素原子取代的C1〜C5烷氧基， 氰基，C 2 -C 11烯基或苯基等; R 3表示氢原子，直链或支链C 1 -C 5烷基或氰基; X表示卤素原子）（2）（ 在式中，R 1，R 2和R 3如上所定义。）

公开(公告)号：US07741511B2

公开(公告)日：2010-06-22

申请号：US11837399

申请日：2007-08-10

申请人： Hiroshi Souda ,  Kazunori Iwakura

发明人： Hiroshi Souda ,  Kazunori Iwakura

IPC分类号： C07C69/24

CPC分类号： C07C67/08 ,  B01J31/0212 ,  C07F7/003 ,  C07C69/747

摘要： There is provided a process for preparing a carboxylic acid ester of formula (3): R2COOR1  (3) wherein R1 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, and R2 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted, a heteroaryl which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, which process is characterized by the steps of reacting a monohydroxy compound of formula (1): R1OH  (1) wherein R1 is as defined above, with a zirconium compound of formula (6): Zr(OR8)4  (6) wherein R8 is an alkyl group or an aryl group which may be substituted and is not the same as R1, to prepare a zirconium catalyst, and reacting a carboxylic acid of formula (2): R2COOH  (2) wherein R2 is as defined above, with the monohydroxy compound of formula (1) in the presence of the zirconium catalyst.

摘要翻译： 提供了制备式（3）的羧酸酯的方法：R2COOR1（3）其中R1是可被取代的烷基，可被取代的烯基，可被取代的炔基，芳烷基 可以被取代的基团，或可以被取代的杂芳基烷基，R 2可以被取代的烷基，可以被取代的链烯基，可被取代的炔基，可被取代的芳基， 可以被取代的杂芳基，可被取代的芳烷基或可被取代的杂芳烷基，该方法的特征在于以下步骤：使式（1）的单羟基化合物：R1OH（1）其中R1为 与式（6）的锆化合物：Zr（OR8）4（6）其中R8是可以被取代且与R1不同的烷基或芳基，制备锆催化剂，以及 反应一个碳 式（2）的二甲酸：其中R 2如上所定义的R 2 COOH（2）与式（1）的单羟基化合物在锆催化剂存在下反应。

公开(公告)号：US20110184184A1

公开(公告)日：2011-07-28

申请号：US12672209

申请日：2008-08-08

申请人： Hiroshi Souda

发明人： Hiroshi Souda

IPC分类号： C07D213/61

CPC分类号： C07D213/61

摘要： A method for purifying an α-unsaturated amine compound represented by Formula (1), the method comprising a step of extracting with water the compound of Formula (1) from a crude product of the α-unsaturated amine compound represented by Formula (1), and a step of extracting with a pyridine solvent the α-unsaturated amine compound of Formula (1) from the aqueous solution containing the compound of Formula (1) obtained in the previous step to obtain a pyridine solvent solution of the compound of Formula (1): wherein R1 represents a hydrogen atom, a C1-4 alkyl group, a halo C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, a C7-9 aralkyl group, or an optionally substituted phenyl group, R2 represents a hydrogen atom, a C1-4 alkyl group, or a C7-9 aralkyl group, and R3 represents a hydrogen atom, a C1-5 alkyl group, a halo C1-4 alkyl group, a hydroxy C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, C2-4 alkenyl group, or a C7-9 aralkyl group.

摘要翻译： 一种纯化由式（1）表示的α-不饱和胺化合物的方法，所述方法包括从式（1）表示的α-不饱和胺化合物的粗产物中用水萃取式（1）的化合物的步骤， 以及从上述步骤中得到的含有式（1）的化合物的水溶液中用吡啶溶剂萃取式（1）的α-不饱和胺化合物的步骤，得到式（1）的化合物的吡啶溶剂溶液 1）：其中R 1表示氢原子，C 1-4烷基，卤代C 1-4烷基，C 1-4烷氧基-C 1-4烷基，C 7-9芳烷基或任选取代的苯基 R 2表示氢原子，C 1-4烷基或C 7-9芳烷基，R 3表示氢原子，C 1-5烷基，卤代C 1-4烷基，羟基C 1-4烷基 基团，C 1-4烷氧基-C 1-4烷基，C 2-4链烯基或C 7-9芳烷基。

公开(公告)号：US07399873B2

公开(公告)日：2008-07-15

申请号：US11837404

申请日：2007-08-10

申请人： Hiroshi Souda ,  Kazunori Iwakura

发明人： Hiroshi Souda ,  Kazunori Iwakura

IPC分类号： C07F7/00

CPC分类号： C07C67/08 ,  B01J31/0212 ,  C07F7/003 ,  C07C69/747

摘要： There is provided a process for preparing a carboxylic acid ester of formula (3): R2COOR1   (3) wherein R1 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, and R2 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted, a heteroaryl which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, which process is characterized by the steps of reacting a monohydroxy compound of formula (1): R1OH   (1) wherein R1 is as defined above, with a zirconium compound of formula (6): Zr(OR8)4   (6) wherein R8 is an alkyl group or an aryl group which may be substituted and is not the same as R1, to prepare a zirconium catalyst, and reacting a carboxylic acid of formula (2): R2COOH   (2) wherein R2 is as defined above, with the monohydroxy compound of formula (1) in the presence of the zirconium catalyst.

公开(公告)号：US06458964B2

公开(公告)日：2002-10-01

申请号：US09779848

申请日：2001-02-09

申请人： Kazunori Iwakura ,  Hiroshi Souda

发明人： Kazunori Iwakura ,  Hiroshi Souda

IPC分类号： C07D23302

CPC分类号： C07D233/32

摘要： There is disclosed a process for producing an optically active hemiester of formula (1): wherein R1, R2 and R5 represent the same meanings as described below, which comprises reacting a cyclic acid anhydride of formula (2): wherein R1 and R2 are different and independently represent a hydrogen atom, a halogen atom, an alkyl group optionally substituted with an alkoxy group or a halogen atom, and the like, with a hydroxy compound of formula (3): R3OH   (3) wherein R3 represents an alkyl group optionally substituted with an alkoxy group, a phenoxy group, a dialkylamino group or a halogen atom and the like, in the presence of an asymmetric catalyst.

摘要翻译： 公开了一种制备式（1）的光学活性半酯的方法：其中R1，R2和R5表示与下述相同的含义，其包括使式（2）的环状酸酐反应：其中R1和R2不同 独立地表示氢原子，卤素原子，任选被烷氧基或卤素原子取代的烷基等与式（3）的羟基化合物反应：其中R 3表示任选被烷氧基取代的烷基， 苯氧基，二烷基氨基或卤素原子等，在不对称催化剂存在下进行。

公开(公告)号：US08779222B2

公开(公告)日：2014-07-15

申请号：US13389168

申请日：2010-08-27

申请人： Hiroshi Souda ,  Koji Hagiya

发明人： Hiroshi Souda ,  Koji Hagiya

IPC分类号： C07C17/25 ,  C07C17/358

CPC分类号： C07C17/25 ,  C07C17/358 ,  C07C21/04

摘要： A production method of 1,1,3-trichloro-1-propene comprising the following steps A and B; Step A: 1,1,1,3-tetrachloropropane is dehydrochlorinated at a temperature between 30° C. and 50° C. in the presence of at least one base selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, and a phase transfer catalyst, Step B: 3,3,3-trichloro-1-propene obtained in the step A is isomerized into 1,1,3-trichloro-1-propene in the presence of a metal catalyst.

摘要翻译： 包含以下步骤A和B的1,1,3-三氯-1-丙烯的制备方法; 步骤A：在选自碱金属氢氧化物和碱土金属氢氧化物中的至少一种碱的存在下，将1,1,1,3-四氯丙烷在30℃至50℃的温度下脱氯化氢， 和相转移催化剂，步骤B：在步骤A中获得的3,3,3-三氯-1-丙烯在金属催化剂的存在下异构化成1,1,3-三氯-1-丙烯。

公开(公告)号：US20120142981A1

公开(公告)日：2012-06-07

申请号：US13389168

申请日：2010-08-27

申请人： Hiroshi Souda ,  Koji Hagiya

发明人： Hiroshi Souda ,  Koji Hagiya

IPC分类号： C07C17/25

CPC分类号： C07C17/25 ,  C07C17/358 ,  C07C21/04

摘要： A production method of 1,1,3-trichloro-1-propene comprising the following steps A and B;Step A: 1,1,1,3-tetrachloropropane is dehydrochlorinated at a temperature between 30° C. and 50° C. in the presence of at least one base selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, and a phase transfer catalyst,Step B: 3,3,3-trichloro-1-propene obtained in the step A is isomerized into 1,1,3-trichloro-1-propene in the presence of a metal catalyst.

摘要翻译： 包含以下步骤A和B的1,1,3-三氯-1-丙烯的制备方法; 步骤A：在选自碱金属氢氧化物和碱土金属氢氧化物中的至少一种碱的存在下，将1,1,1,3-四氯丙烷在30℃至50℃的温度下脱氯化氢， 和相转移催化剂，步骤B：在步骤A中获得的3,3,3-三氯-1-丙烯在金属催化剂的存在下异构化成1,1,3-三氯-1-丙烯。

公开(公告)号：US06750370B2

公开(公告)日：2004-06-15

申请号：US10195409

申请日：2002-07-16

申请人： Hiroshi Souda ,  Kazunori Iwakura ,  Fumisato Goto

发明人： Hiroshi Souda ,  Kazunori Iwakura ,  Fumisato Goto

IPC分类号： C07C6104

CPC分类号： C07C51/353 ,  C07C67/333 ,  C07C61/37 ,  C07C61/35 ,  C07C61/40 ,  C07C69/747 ,  C07C69/743

摘要： There is disclosed a process for the racemization of a vinyl-substituted cyclopropanecarboxylic acid or a derivative thereof, which is characterized by reacting an optically active vinyl-substituted cyclopropanecarboxylic acid compound of formula (1): wherein R1, R2, R3 and R4 each independently represent a hydrogen atom, a halogen atom, alkyl which may be substituted having 1-4 carbon atoms, aryl which may be substituted, or alkoxycarbonyl which may be substituted, or R1 and R2 are bonded to form an alkylene group, which may be substituted; and wherein X represents hydroxyl, a halogen atom, alkoxy which may be substituted having 1-20 carbon atoms, or aryloxy which may be substituted, with a nitric compound or a nitrogen oxide.

摘要翻译： 公开了乙烯基取代的环丙烷羧酸或其衍生物外消旋化的方法，其特征在于使式（1）的光学活性乙烯基取代的环丙烷羧酸化合物：其中R 1，R 2， R 3和R 4各自独立地表示氢原子，卤素原子，可被取代有1-4个碳原子的烷基，可被取代的芳基，或可被取代的烷氧基羰基，或R 1和R 2 <2>键合以形成可以被取代的亚烷基; 并且其中X表示羟基，卤素原子，可被取代有1-20个碳原子的烷氧基，或可被取代的芳氧基，与硝酸化合物或氮氧化物反应。

公开(公告)号：US08999080B2

公开(公告)日：2015-04-07

申请号：US12166893

申请日：2008-07-02

申请人： Hiroshi Souda ,  Kouichi Akiyama ,  Hiroshi Horikawa ,  Masahiko Shioda

发明人： Hiroshi Souda ,  Kouichi Akiyama ,  Hiroshi Horikawa ,  Masahiko Shioda

IPC分类号： C22C21/02 ,  C22C21/08 ,  C22C21/16 ,  C22F1/043 ,  C22C21/04 ,  F02F1/24

CPC分类号： C22F1/043 ,  C22C21/02 ,  C22C21/04 ,  F02F1/24

摘要： Disclosed are: a casting aluminum alloy that is excellent in elongation as alternative properties of a high cycle fatigue strength and a thermal fatigue strength and is suitably usable for a casting for which both of the excellent high cycle fatigue strength and the excellent thermal fatigue strength are required, for example, an internal combustion engine cylinder head; a casting made of the aluminum alloy; a manufacturing method of the casting; and further, an internal combustion engine cylinder head composed of the aluminum alloy casting and manufactured by the manufacturing method of the casting. The casting aluminum alloy contains, in terms of mass ratios, 4.0 to 7.0% of Si, 0.5 to 2.0% of Cu, 0.25 to 0.5% of Mg, no more than 0.5% of Fe, no more than 0.5% of Mn, and at least one component selected from the group consisting of Na, Ca and Sr, each mass ratio of which is 0.002 to 0.02%.

摘要翻译： 公开了一种铸造铝合金，其具有优异的伸长率，作为高循环疲劳强度和热疲劳强度的替代性能，并且适合用于优异的高循环疲劳强度和优异的热疲劳强度两者的铸件 需要，例如内燃机气缸盖; 由铝合金铸造的铸件; 铸造的制造方法; 此外，由铸造铝合金构成的内燃机气缸盖，通过铸造的制造方法制造。 铸造铝合金以质量比计含有Si：4.0〜7.0％，Cu：0.5〜2.0％，Mg：0.25〜0.5％，Fe：0.5％以下，Mn：0.5％以下，以及 选自Na，Ca和Sr中的至少一种成分，其质量比为0.002〜0.02％。