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    • 1. 发明申请
    • METHOD FOR PRODUCING OPTICALLY ACTIVE NAPHTHALENE COMPOUND
    • 用于生产光学活性萘基化合物的方法
    • US20150152082A1
    • 2015-06-04
    • US14240466
    • 2012-08-24
    • Koji MatsuyamaMasanori HatsudaMasahiko YoshinagaMitsuhiro YadaKoichi Tanimoto
    • Koji MatsuyamaMasanori HatsudaMasahiko YoshinagaMitsuhiro YadaKoichi Tanimoto
    • C07D401/04C07C255/03C07C25/06
    • C07D401/04C07B53/00C07C25/06C07C255/03
    • The present invention provides an industrially advantageous method for producing an optically active naphthalene compound useful as a therapeutic agent for dermatitis or the like. Specifically, the present invention provides a method for producing an optically active naphthalene compound [I], which comprises: a step of reacting a compound [a-1] and a compound [b-1] with each other in the presence of a base and a catalyst that is composed of a Pd compound and a tertiary phosphine ligand (step a); a step of asymmetrically hydrogenating a compound [c-1] in the presence of a hydrogen donor and a complex that is prepared from a ruthenium compound and a chiral ligand, or alternatively in the presence of an optically active oxazaborolidine compound (a CBS catalyst) and a boron hydride compound (step b); and a step of treating a compound [d-1] with a reducing agent (step c). (In the above formulae, Ra and Rb represent the same or different lower alkyl groups; and X1 represents a halogen atom.)
    • 本发明提供了用于制造用作皮炎等的治疗剂的光学活性萘化合物的工业上有利的方法。 具体而言,本发明提供了一种光学活性萘化合物[I]的制造方法,其特征在于,在碱的存在下,使化合物[a-1]和化合物[b-1] 和由Pd化合物和叔膦配体组成的催化剂(步骤a); 在氢供体和由钌化合物和手性配体制备的络合物的存在下,或者在光学活性的恶唑硼烷化合物(CBS催化剂)存在下,不对称地氢化化合物[c-1] 和硼氢化合物(步骤b); 和用还原剂处理化合物[d-1](步骤c)的步骤。 (上式中,Ra和Rb表示相同或不同的低级烷基,X1表示卤素原子。)
    • 8. 发明授权
    • Liquid enrichment and/or separation by absorption processes
    • 通过吸收过程进行液体富集和/或分离
    • US2974178A
    • 1961-03-07
    • US61577956
    • 1956-10-15
    • ROHM & HAAS
    • HWA JESSE C HMCBURNEY CHARLES HMEITZNER ERICH F
    • B01D15/04B01D15/08B01J20/22C02F1/28C07B61/00C07C7/12C07C17/38C07C45/79C07C67/48C07C201/16C08F36/20C10G25/02
    • C10G25/02B01D15/08B01D15/265B01J20/22C07C7/12C07C17/38C07C17/389C07C29/76C07C29/82C07C45/79C07C45/84C07C67/56C07C201/16C07C253/34C07C2601/14C08F36/20C07C205/06C07C19/045C07C9/21C07C13/18C07C19/041C07C25/06C07C15/04C07C255/08C07C49/08C07C33/03C07C69/24C07C69/50
    • In a method of concentrating or separating a component of a homogenous liquid mixture of at least two substantially non-ionogenic compounds, at least one of which is organic, the mixture is contacted with a resin absorbent having a large surface area per unit weight, the resin absorbent being (a) a crosslinked addition polymer other than an ionexchange resin, (b) insoluble in the liquid mixture and (c) having a preferential absorptive capacity for the component to be concentrated. Absorption may be tested for by agitating the resin with a mixture for a given time and analysing the mixture before and after absorption. The separatory capacity of a resin is defined as where m is the weight of the resin in grams, V is the volume of liquid mixture added in ml., and c0 and c are the volume fractions of the preferentially absorbed component in the liquid phase before and after absorption respectively. Separatory capacities of various specified resins are given for each of the following in admixture with iso-octane: 4-vinylcyclohexene, cyclohexanol, toluene, ethyl acetate, methyl ethyl ketone, styrene, chlorobenzene, ethylene dichloride, chloroform, dioxane, pyridine, naphthalene, nitrobenzene and pyrrole; for each of ethylene dichloride, styrene, and chlorobenzene in admixture with toluene; and for the first named component of each of the following mixtures: ethylene dichloride-ethyl acetate, styrene-4-vinylcyclohexene, chlorobenzene-allyl alcohol, benzene-acrylonitrile, allyl alcohol-water, chloroform-acetone. The treatment of hydrocarbon mixtures such as paraffin/naphthene, olefin/paraffin and solvent mixtures containing alcohols, ketones, hydrocarbons and esters; and also mixtures of capryl alcohol with methyl hexyl ketone and n-butanol with water is referred to. The absorption process can be carried out batchwise or continuously. In the former the liquid mixture is passed through a column packed with resin particles, or the resin particles may pass countercurrent to the liquid. When a two-component mixture A and B, of which A is preferentially absorbed, is passed over the resin, B issues first from the resin until the limit of the absorption capacity for A is reached, after which the original mixture A and B will issue. Enriched A is separated from the resin e.g. by heat, steam distillation, extraction or desorption with another solvent. In the continuous treatment the use of a desorbent C allows complete separation of A and B, and the resin supported in a column is fed alternately with liquid mixture and with desorbent. The desorbent consists of one or more liquids, is completely miscible with A and B, and has a swelling power for the resin of the same order as that of one of the components of the liquid mixture to be separated. Examples describe batch methods for partially separating tolueneiso-octane, dimethyl sebacate-iso-octane, methyl caprate-iso-octane, ethylene dichloride-cyclohexane mixtures using copolymers of divinyl benzene with 2-ethylhexyl acrylate, n-butyl acrylate, n-butyl methacrylate, ethoxyethyl acrylate, and methyl acrylate as absorbents. Examples also describe continuous methods for completely separating toluene from isooctane using n-pentane as desorbent; dimethyl sebacate from methyl stearate and/or methyl caprate using iso-octane as desorbent; ethylene dichloride from cyclohexane and chloroform from acetone using toluene as desorbent in each case; also chlorobenzene from allyl alcohol, benzene from acrylonitrile, and nitrobenzene from iso-octane using as desorbents methanol, methylene dichloride and benzene respectively. Resins used in the examples of continuous methods are n-butyl and methyl acrylates copolymerized with divinylbenzene. Specifications 786,755, 846,890 and 858,865 are referred to.ALSO:In a method of concentrating or separating a component of a homogeneous liquid mixture of at least two substantially non-ionogenic compounds, at least one of which is organic, the mixture is contacted with a resin absorbent having a large surface area per unit weight, the resin absorbent being (a) a cross-linked addition polymer other than an ion-exchange resin, (b) insoluble in the liquid mixture and (c) having a preferential absorptive capacity for the component to be concentrated. Absorption may be tested for by agitating the resin with a mixture for a given time and analysing the mixture before and after absorption. The separatory capacity of a resin is defined as where m is the weight of the resin in grams, V is the volume of liquid mixture added in ml., and Co and C are the Volume fractions of the preferentially absorbed component in the liquid phase before and after absorption respectively. Separatory capacities of various specified resins are given for each of the following in admixture with iso-octane: 4-vinylcyclohexene, cyclohexanol, toluene, ethyl acetate, methylethylketone, styrene, chlorobenzene, ethylene dichloride, chloroform dioxane, pyridine, naphthalene, nitrobenzene, and pyrrole; for each of ethylene dichloride, styrene, and chlorobenzene in admixture with toluene; and for the first named component of each of the following mixtures: ethylene dichloride-ethyl acetate, styrene, 4-vinylcyclohexene, chlorobenzene-allyl alcohol, benzene-acrylonitrile, allyl alcohol-water, chloroform-acetone. The treatment of hydrocarbon mixtures such as paraffin/naphthene, olefin/paraffin and solvent mixtures containing alcohols. Ketones, hydrocarbons and esters; and also mixtures of capryl alcohol with methylhexyl ketone and n-butanol with water is referred to. The absorption process can be carried out batchwise or continuously. In the former the liquid mixture is passed through a column packed with resin particles, or the resin particles may pass countercurrent to the liquid. When a two-component mixture A and B, of which A is preferentially absorbed, is passed over the resin, B issues first from the resin until the limit of the absorption capacity for A is reached, after which the original mixture A and B will issue. Enriched A is separated from the resin e.g. by heat, steam distallition, extraction or desorption with another solvent. In the continuous treatment the use of a desorbent C allows complete separation of A and B and the resin supported in a column is fed alternately with liquid mixture and with desorbent. The desorbent consists of one or more liquids, is completely miscible with A and B, and has a swelling power for the resin of the same order as that of one of the components of the liquid mixture to be separated. Examples describe batch methods for partially separating toluene-iso - octane, dimethyl sebacate-iso-octane, p methyl caprate-iso-octane, ethylene dichloride-cyclohexane mixtures using copolymers of divinyl benzene with 2-ethylhexyl acrylate, n-butyl acrylate, n-butyl methacrylate, ethoxy-ethyl acrylate, and methyl acrylate as absorbents. Examples also describe continuous methods for completely separating toluene from iso-octane using n-pentane as desorbent: dimethyl sebacate from methyl stearate and/or methyl caprate using iso-octane as desorbent; ethylene dichloride from cyclohexane and chloroform from acetone using toluene as desorbent in each case; also chlorobenzene from allyl alcohol, benzene from acrylonitrile, and nitrobenzene from iso-octane using as desorbents methanol, methylene dichloride and benzene respectively. Resins used in the examples of continuous methods are n-butyl and methyl acrylates copolymerized with divinyl-benzene. Specifications 786,755, 846,890 and 858,865 are referred to.