Separation of enantiomers of chiral carboxylic acids
    3.
    发明授权
    Separation of enantiomers of chiral carboxylic acids 失效
    手性羧酸的对映异构体的分离

    公开(公告)号:US4337352A

    公开(公告)日:1982-06-29

    申请号:US263812

    申请日:1981-05-15

    申请人: Klaus Naumann

    发明人: Klaus Naumann

    CPC分类号: C07C51/487

    摘要: A process for the separation of enantiomers of a chiral carboxylic acid, comprising reacting an alkali metal salt of the acid with an amount of an optically active amine salt which is equivalent to only one enantiomer, in an aqueous weakly alkaline buffered solution as the reaction medium, the reaction medium having a pH value at which the entire acid is present in the ionized form but at which no amine salt is yet deprotonated. Advantageously the carboxylic acid is of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently is hydrogen, alkyl, with 1-4 C atoms, halogen, optionally substituted phenyl or optionally substituted phenylmercapto,the optically active amine salt is a mineral acid salt of a phenylglycine alkyl ester, .alpha.-methylbenzylamine, phenylethylamine, phenylethanolamine, 1-phenyl-2-dimethyl-amino-1,3-propanediol or abietylamine, the buffered solution contains potassium carbonate, sodium carbonate, sodium bicarbonate or sodium hydrogen phosphate as the buffering agent, and the reaction is effected at about 0.degree. to 100.degree. C., the process including the further steps of separating the precipitated ammonium salt from the alkali metal salt that remains in solution, treating the ammonium salt with a strong acid whereby the free carboxylic acid enantiomer is liberated, and treating the alkali metal salt that remains in solution with a strong acid whereby the free carboxylic enantiomer is liberated.

    摘要翻译: 一种用于分离手性羧酸的对映异构体的方法,包括使酸的碱金属盐与一定量的仅相当于一种对映异构体的光学活性胺盐在作为反应介质的弱弱碱性缓冲溶液中反应 反应介质具有pH值,其中整个酸以离子形式存在,但没有胺盐尚未去质子化。 有利地,羧酸具有下式:其中R 1和R 2各自独立地为氢,具有1-4个C原子的烷基,卤素,任选取代的苯基或任选取代的苯基巯基,光学活性胺盐是 苯基甘氨酸烷基酯,α-甲基苄基胺,苯乙基胺,苯基乙醇胺,1-苯基-2-二甲基 - 氨基-1,3-丙二醇或非胺,缓冲溶液含有碳酸钾,碳酸钠,碳酸氢钠或磷酸氢钠作为缓冲剂 该反应在约0℃至100℃下进行,该方法包括进一步的步骤:将沉淀的铵盐与残留在溶液中的碱金属盐分离,用强酸处理铵盐,由此使游离的 释放羧酸对映异构体,并用强酸处理残留在溶液中的碱金属盐,由此游离羧酸对映体被释放 。

    Separation of stereoisomeric vinylcyclopropanecarboxylic acids
    5.
    发明授权
    Separation of stereoisomeric vinylcyclopropanecarboxylic acids 失效
    立体异构乙烯基环丙烷羧酸的分离

    公开(公告)号:US4236026A

    公开(公告)日:1980-11-25

    申请号:US970099

    申请日:1978-12-15

    申请人: Klaus Naumann

    发明人: Klaus Naumann

    CPC分类号: C07C51/487

    摘要: A process for the separation of the cis- and trans-stereoisomers of a substituted vinylcyclopropanecarboxylic acid of the formula ##STR1## in which R is alkyl with 1 to 4 carbon atoms, halogen, phenyl or phenyl substituted by at least one of alkyl and halogen, andR.sup.1 is hydrogen, alkyl with 1 to 4 carbon atoms or halogen, orR and R.sup.1, together with the adjacent C atom, form a carbocyclic ring,comprising reacting the free vinylcyclopropanecarboxylic acid in a weakly alkaline aqueous solution with an amount of an amine salt corresponding to the proportion of the cis-isomer present thereby to form a salt precipitate enriched in one of the stereoisomers, separating the precipitant from the supernatant, separately reacting the precipitate and supernatant with a strong acid to liberate the isomeric vinylcyclopropanecarboxylic acid, and recrystallizing at least one of the stereoisomers.

    摘要翻译: 分离式为“IMAGE”的取代的乙烯基环丙烷羧酸的顺式和反式立体异构体的方法,其中R是具有1至4个碳原子的烷基,卤素,苯基或被至少一个烷基和卤素取代的苯基 R 1是氢,具有1至4个碳原子的烷基或卤素,或R和R 1与相邻的C原子一起形成碳环,包括使弱碱性水溶液中的游离乙烯基环丙烷羧酸与一定量的 胺盐对应于存在的顺式异构体的比例,从而形成富含一种立体异构体的盐沉淀物,将沉淀剂与上清液分离,分别使沉淀物和上清液与强酸反应以释放异构的乙烯基环丙烷羧酸,以及 使至少一种立体异构体重结晶。

    Separation of stereoisomeric cyclic carboxylic acids
    7.
    发明授权
    Separation of stereoisomeric cyclic carboxylic acids 失效
    立体异构环状羧酸的分离

    公开(公告)号:US4196304A

    公开(公告)日:1980-04-01

    申请号:US883979

    申请日:1978-03-06

    申请人: Klaus Naumann

    发明人: Klaus Naumann

    CPC分类号: C07C51/487

    摘要: A process for the separation of the stereoisomers of a stereoisomer mixture of a cyclic carboxylic acid of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkenyl,R.sup.3 is alkyl, alkenyl or alkynyl having up to 6 carbon atoms and optionally substituted by halogen, or alkoxycarbonyl having up to 5 carbon atoms, or is aralkyl or aryl, orR.sup.1 plus R.sup.2, or R.sup.1 plus R.sup.3, together with the adjacent C atom, form a carbocyclic ring,R.sup.3 and COOH are cis or trans to one another and the COOH group is in the exo or endo position if R.sup.1 and R.sup.3 together form a ring, andn is 0, 1 or 2,which comprises contacting a weakly alkaline, aqueous solution of the stereoisomeric mixture with a non-polar organic solvent, whereby the cis or endo isomeric free acid enters the organic solvent while the trans or exo isomer remains in the aqueous solution as a salt, and separating the aqueous solution from the organic solvent, thereby to separate the isomers. Preferred acids are cyclopropanecarboxylic acid derivatives, the aqueous solution is preferably buffered to a pH of about 7 to 9 and the organic solvent is preferably a hydrocarbon, halogenated hydrocarbon, aromatic hydrocarbon or ether.

    摘要翻译: R 1和R 2各自独立地为氢,卤素,C 1 -C 6烷基或C 2 -C 6 - 烯基的式(I)的环状羧酸的立体异构体混合物的立体异构体的分离方法,R3是烷基 ,具有至多6个碳原子并且任选被卤素取代的链烯基或炔基,或具有至多5个碳原子的烷氧基羰基,或芳基烷基或芳基,或R1 + R2,或R1 + R3与相邻C原子一起形成 碳环,R 3和COOH是顺式或反式的,如果R 1和R 3一起形成环,COOH基团处于外部或内部位置,并且n是0,1或2,其包括使弱碱性水溶液 立体异构体混合物与非极性有机溶剂的溶液,由此顺式或内同异构游离酸进入有机溶剂,同时反式或外型异构体作为盐保留在水溶液中,并将水溶液与有机溶剂分离, 从而分离异构体。 优选的酸是环丙烷羧酸衍生物,水溶液优选缓冲至约7至9的pH,有机溶剂优选为烃,卤代烃,芳族烃或醚。

    Electronic musical instrument
    9.
    发明授权
    Electronic musical instrument 失效
    电子乐器

    公开(公告)号:US4085646A

    公开(公告)日:1978-04-25

    申请号:US690557

    申请日:1976-05-27

    申请人: Klaus Naumann

    发明人: Klaus Naumann

    CPC分类号: G10H5/005

    摘要: An electronic musical instrument providing continuous cybernetic tone finding controlled by functions of the human mouth. The instrument includes a mouthpiece into which air is to be blown from the mouth of a player having a measuring apparatus at least partially mounted therein. The measuring apparatus includes an arrangement for producing a pitch determining signal representing a measure of the mouth cavity of the player and a volume determining signal representing the velocity or pressure of the air blown into the mouthpiece. Tone generating apparatus is provided for generating a tone signal whose frequency varies with the level of a control signal applied thereto with a control signal being applied to the tone generating apparatus in accordance with the pitch determining signal and having a level representing a measure of the mouth cavity of the player. Another control signal in accordance with the volume determining signal serves for controlling the output of the tone generating apparatus with the output being converted to sound.

    摘要翻译: 一种电子乐器,提供由人嘴功能控制的连续的控制论色调。 仪器包括一个吸嘴,空气从具有至少部分地安装在其中的测量装置的演奏者的嘴部吹出。 该测量装置包括用于产生表示播放器的口腔的度量的音调确定信号的装置和表示吹入到接口管中的空气的速度或压力的音量确定信号。 提供音调发生装置,用于产生音调信号,其频率随施加到其上的控制信号的电平而变化,控制信号根据音调确​​定信号被施加到乐音发生装置,并且具有表示口的测量的音量 球员的腔。 根据音量确定信号的另一个控制信号用于控制音调发生装置的输出,并将输出转换成声音。