申请人:Honshu Chemical Industry Co., Ltd.
公开号:EP2851359A1
公开(公告)日:2015-03-25
To achieve the object of providing a new method of manufacturing 4,4"-dihydroxy-m-terphenyl, the present invention provides a method of manufacturing 4,4"-dihydroxy-m-terphenyl expressed by General Formula (4) below, characterized in that such method uses a 2-cyclohexene-1-one expressed by General Formula (1) below or 3-hydroxycyclohexane-1-one expressed by General Formula (2) below, and phenol expressed by General Formula (3) below as materials and implements Step (A), Step (B), and Step (C) below, in this order, or Step (D) and Step (C) below, in this order:
(In the formulas, each R2 independently represents an alkyl group, alkoxy group, aromatic hydrocarbon group, or halogen atom, while m independently indicates 0 or an integer of 1 to 4, where R2 substitution does not occur in the third position when m is 1 or greater, and when m is 2 or greater, R2's may be identical or different, and R2 substitution does not occur in two positions of the same carbon atom. In addition, R2 and m in General Formula (1) may be identical to or different from R2 and m in General Formula (2), respectively.)
(In the formula, each R1 independently represents an alkyl group, alkoxy group, aromatic hydrocarbon group, halogen atom, or hydroxyl group, while n indicates 0 or an integer of 1 to 4, where R1's may be identical or different when n is 2 or greater.)
Step (A): Step to obtain a 1,1,3-trisphenol by causing the 2-cyclohexene-1-one or 3-hydroxycyclohexane-1-one and phenol to react with each other in the presence of a catalyst.
Step (B): Step to obtain a bis(4-hydroxyphenyl)cyclohexene by causing the 1,1,3-trisphenol to undergo breakdown reaction.
Step (C): Step to obtain a 4,4"-dihydroxy-m-terphenyl by dehydrogenating the bis(4-hydroxyphenyl)cyclohexene.
Step (D): Step to obtain a bis(4-hydroxyphenyl)cyclohexene by causing the 2-cyclohexene-1-one or 3-hydroxycyclohexane-1-one and phenol to react with each other in the presence of a catalyst.
(In the formula, each R1 and n is independently the same as the corresponding items in General Formula (3), respectively, while R2 and m are the same as the corresponding items in General Formula (1) or General Formula (2), respectively.)
为了实现提供一种制造 4,4"-二羟基间三联苯的新方法的目的,本发明提供了一种制造由下式(4)表示的 4,4"-二羟基间三联苯的方法、其特征在于,该方法使用以下通式(1)表示的2-环己烯-1-酮或以下通式(2)表示的3-羟基环己烷-1-酮和以下通式(3)表示的苯酚作为材料,并依次实施步骤(A)、步骤(B)和步骤(C),或依次实施步骤(D)和步骤(C):
(在公式中,每个 R2 独立地代表烷基、烷氧基、芳香族烃基或卤素原子,而 m 独立地表示 0 或 1 至 4 的整数,其中当 m 为 1 或更大时,R2 取代不会发生在第三个位置,而当 m 为 2 或更大时,R2 可以相同或不同,R2 取代不会发生在同一碳原子的两个位置。此外,通式(1)中的 R2 和 m 可分别与通式(2)中的 R2 和 m 相同或不同)。
(式中,每个 R1 独立地代表烷基、烷氧基、芳香烃基、卤素原子或羟基,而 n 表示 0 或 1 至 4 的整数,其中当 n 为 2 或更大时,R1 的可能相同或不同)。
步骤 (A):使 2-环己烯-1-酮或 3-羟基环己烯-1-酮和苯酚在催化剂存在下相互反应,从而获得 1,1,3-三苯酚的步骤。
步骤 (B):使 1,1,3-三苯酚发生分解反应,得到双(4-羟基苯基)环己烯的步骤。
步骤(C):通过双(4-羟基苯基)环己烯的脱氢反应,得到 4,4"-二羟基间三联苯。
步骤(D):在催化剂存在下,使 2-环己烯-1-酮或 3-羟基环己烯-1-酮与苯酚相互反应,得到双(4-羟基苯基)环己烯的步骤。
(式中,各 R1 和 n 分别独立地与通式(3)中的相应项目相同,而 R2 和 m 分别与通式(1)或通式(2)中的相应项目相同)。