• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Benzoyl cyanide is made by reacting benzoyl chloride with an alkali cyanide in the presence of a carboxylic acid nitrile and a copper (I) salt at a temperature of about 50 DEG to 160 DEG C.
    公开号:SU843734A3
    申请号:SU772491919
    申请日:1977-06-02
    公开日:1981-06-30
    发明作者:Кленк Херберт；Люсслинг Теодор；Майерхофер Альфред；Офферманнс Хериберт；Вагнер Ханс
    申请人:Дегусса Аг (Фирма)；
    IPC主号:
    专利说明:

    (54) METHOD FOR OBTAINING BENZOYL CYANIDE
    This invention relates to organic chemistry; namely, a method for producing benzoyl cyanide. Benzoyl cyanide is of interest as an intermediate product for the production of various herbicides. A method of producing benzoyl cyanide by reacting benzoyl chloride with anhydrous hydrogen cyanide in α-pyridine medium at room temperature is known. The yield of the target product reaches 80%. The disadvantage of this method is the formation of by-products; especially dimers of benzoyl cyanide, benoyloxyphenyl small odinitrile. As a result, not only the yield of benzoyl cyanide is not completely unsatisfactory, but also its purity. The benzoyl cyanide is separated from its dimer only with considerable difficulties and not completely. The closest in technical essence to the present invention is a method for producing benzoyl cyanide by reacting benzoyl chloride with excess monovalent copper cyanide | The reaction is carried out at temperatures up to 80 ° C in acetonitrile or benzonitrile, or in ether with lithium chloride or lithium iodide. The yield of the target product reaches 65% 2. The main disadvantage of this method is the low yield of the target product. The purpose of the invention is to increase the yield of the target product. This goal is achieved by the fact that benzoyl cyanide is obtained by reacting benzoyl chloride with metal cyanide in the presence of an additive metal salt I g. Periodic system and carboxylic acid nitriles when heated followed by separation of the target product, the distinguishing feature of which is that alkali metal cyanide is used as metal cyanide, and monovalent copper salt is used as an additive, and the process is carried out at 50-160 ° С . It is preferable to take 1.05-1.5 equivalents of alkali metal cyanide 0.1-0.5 mol of carboxylic acid nitrile, 0.05-0.5 equivalents of monovalent copper per mole of benzoyl chloride.
    The process is preferably carried out at 90-130s, in an organic inert solvent.
    The benzoyl cyanide obtained by the method with a yield of more than 90% has a content of the main product of more than 98%.
    The method is carried out as follows.
    The proposed process temperature is 50-1bOOs. The pressure can be chosen quite arbitrarily; however, in order for the instrumentation of the process to be simple, one should slightly deviate from the normal pressure. In some cases, due to the presence of volatile substances, it is advisable to work at an elevated pressure corresponding to temperature.
    In some cases, an inert solvent may be added for dilution. Aromatic hydrocarbons such as benzene, toluene or xylenes, or aliphatic hydrocarbons such as can be used as the solvent. ligroin with a boiling range of from 90 to 140 s, or such halogen-substituted, in particular, chlorinated, aromatic or aliphatic hydrocarbons, such as chlorobenzene, dichlorobenzenes or tetrachloroethane.
    According to the invention, the exchange reaction is carried out with alkali metal cyanides. It is advisable to take stoichiometric amounts of cyanide. It is preferable to use, for example, 1.05-3.0 equivalents of cyanide, in particular 1.06-1.5 equivalents of cyanide per mole of benzoyl chloride.
    The exchange reaction is carried out in the presence of a carboxylic acid nitrile. Nitriles are used which, under the conditions of the exchange reaction, are liquid and do not change. Particularly suitable are nitriles of saturated aliphatic monocarboxylic acids with 2-6 carbon atoms, for example acetonitrile or isobutyric acid nitrile.
    In addition, the exchange reaction is carried out in the presence of copper (I) salts. Copper cyanide (1), copper (I) chloride are used.
    Nitriles and copper salts (|) are taken in amounts depending on the conditions of the exchange reaction, such as temperature and pressure, as well as the type and amount of solvent used to dilute.
    The use of cyanide in the form of an alkali metal cyanide is envisaged. If cyanide is used in the form of a salt, copper (I), then it is possible to save in whole or in part an equivalent amount of alkali metal cyanide. It is advisable to enter no more than 0.5
    equivalent of cyanide in the form of copper salts.
    Example 1. In a vessel for carrying out an exchange reaction, equipped with a reflux condenser, 140.5 g (1.0 mol) of benzoyl chloride are mixed with 54 g (1.1 mol) of sodium cyanide, 9 g (0.1 mol) of copper cyanide (1 ), 25 ml of xylene and 7.5 ml (0.14 mol) of acetonitrile. The mixture is heated with stirring to 130 s and kept at this temperature for 3 hours, and then cooled to 15 s. The salts thus obtained, preferably sodium chloride, are filtered off and washed with 25 ml of xylene. The filtrate is subjected to fractional distillation under reduced pressure. Obtain 119.5 g (91%) of benzoyl cyanide with m. Kip. IZ-IT C at a pressure of 32.7 mm Hg.
    Example 2. Analogously to Example 1, but along with 140.5 g (1.0 mol of benzoyl chloride), 59 g (1.2 mol of sodium cyanide, 30 g (0.3 mol) of copper (I) chloride, 25 ml of xylene and 15 ml (0.3 mol) of acetonitrile. 118 g (91%) of benzoyl cyanide are obtained with a bale of 114-117 C at a pressure of 32.7 mm Hg.
    Example 3. Analogously to Example 1, however, instead of xylene and acetonitrile, 25 ml of ligroin (boiling range 110-140 ° C) and 25 ml (0.3 mol) of isobutyric acid nitrile are used. The exchange reaction is carried out at. Obtain 120 g (92%) of benzoyl cyanide with m. Kip. 113-115s with a pressure of 30.4 mm Hg.
    Example 4. Analogously to Example 1, but using 26.2 ml (0.5 mol) of acetonitrile, the exchange reaction is carried out at 105 s. 119 g (91%) of benzoyl cyanide are obtained with a bp. 115-117 ° C at a pressure of 34 mm Hg.
    Example 5. Analogously to Example 1, but with 140.5 g (1.0 mol) of benzoyl chloride 73, 5 g (1.5 mol) of sodium cyanide and 9 g (0.1 mol) of copper (I) cyanide in the presence of 88 ml xylene and 9 ml of acetonitrile. Get 124 g (96%) of benzoyl cyanide with m. Kip. 115-1170s at 33 mmHg
    Example 6. Analogously to example 2, but using a mixture of 140.5 g (1.0 mol) of benzoyl chloride, 59 g (1.2 mol) of sodium cyanide, 30 g (0.1 mol) of copper (I) chloride, 25 ml xylene and 15 ml of acetonitrile. The mixture is heated in a stainless steel pressure tank equipped with a stirrer and kept at 3 hours. The pressure is adjusted to 2.8 bar. Obtain 115 g (88%) of benzoyl cyanide with m. Kip. 116-1170С at 32.7 mm Hg
    Example 7. The process is carried out analogously to example 4, but without the addition of xylene, and holding the mixture for 8 hours at 82 ° C. Get 118 g
    (90%) benzoylcyanide with t. Kip. 920s at 12.2 mmHg
    The resulting benzoyl cyanide is investigated by argentometric-potentiographic titration, as well as by gas chromatography. In each case, the content in the product was found to be at least 98% by weight of benzoyl cyanide. T. pl. target product 33-34 C.
    Example c. The process is carried out in the same manner as in the case of Example 2, but with the difference that 43 g (0.3 mol) of monovalent copper bromide is used instead of chloride. The yield of benzoyl cyanide is 117 tons, which corresponds to 89% based on the starting benzoyl chloride. T. Kip. benzoyl cyanide is equal to 114-11 bos with a pressure of 30.4 mm Hg. st,
    EXAMPLE 9 The process is carried out as in Example 1, but with the difference that instead of monovalent copper cyanide and sodium cyanide, 71.0 g (0.3 mol) of tetracyanocuprate (|) sodium are used. . The reaction is carried out at 130 ° C. The yield of benzoyl cyanide is 120 g, which corresponds to 92% based on the starting benzoyl chloride. T. Kip. benzoyl cyanide obtained is equal to 115-11b ° C at a pressure of 30.4 mm Hg. Art.
    权利要求:
    Claims (6)
    [1]
    1. Method for producing benzoyl cyanide by reacting benzoyl chloride
    with metal cyanide in the presence of extra salt of metal salt Periodic sisteysh and nitrile carboxylic acid when heated, followed by separation of the target product, about t-. characterized by the fact that, in order to increase the yield, alkali metal cyanide is used as a metal cyanide, and monovalent salt is used as an additive, and the process is carried out at SO-ied C.
    0
    [2]
    2. The way nori. 1, characterized in that 1.05-1.5 equivalents of alkali metal cyanide is used per mole of benzoyl chloride.
    [3]
    3. Method according to paragraphs. 1 and 2, about tl and 5 by the fact that 0.1-0.5 mol of carboxylic acid nitrile is taken per mole of benzoyl chloride.
    [4]
    4. Method according to paragraphs. 1-3, on the basis of the fact that per mole
    0 benzoyl chloride takes 0, the equivalent of monovalent copper salt.
    [5]
    5. Method according to paragraphs. 1-4, characterized in that the process is carried out at a temperature of from 90 to
    five .
    [6]
    6. Method according to paragraphs. 1-5, that is, that the TeVi process is carried out in an inert organic solvent medium.
    Sources of information taken into account in the examination
    1.Bull. Soc. Chim. France, 1972, 2402.
    2.Z. Phys. Chem. 1943, 192, 200 (prototype).
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    同族专利:
    公开号 | 公开日
    FR2353524B1|1983-04-15|
    AT347437B|1978-12-27|
    GB1552718A|1979-09-19|
    IL52232D0|1977-08-31|
    ATA392077A|1978-05-15|
    DE2624891C2|1982-11-18|
    DE2624891A1|1977-12-22|
    BE855251A|1977-11-30|
    IT1143576B|1986-10-22|
    DD129903A5|1978-02-15|
    FR2353524A1|1977-12-30|
    JPS52148041A|1977-12-08|
    US4113773A|1978-09-12|
    IL52232A|1980-09-16|
    NL7706155A|1977-12-06|
    CH627155A5|1981-12-31|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE835141C|1948-10-26|1952-03-27|Schering Ag|Process for the preparation of ª ‡ -Ketocarbonsaeurenitrilen|
    DE2528211C3|1975-06-25|1980-03-06|Bayer Ag, 5090 Leverkusen|Process for the production of acyl cyanides|
    DE2614242C3|1976-04-02|1986-11-13|Bayer Ag, 5090 Leverkusen|Process for the production of acyl cyanides|DE2753656C2|1977-12-02|1982-11-25|Degussa Ag, 6000 Frankfurt|Process for the production of benzoyl cyanide|
    DE2753657C2|1977-12-02|1982-11-25|Degussa Ag, 6000 Frankfurt|Process for the production of benzoyl cyanide|
    US4209462A|1978-12-18|1980-06-24|Stauffer Chemical Company|Method for preparing acyl cyanides|
    DE3011305A1|1980-03-24|1981-10-15|Degussa Ag, 6000 Frankfurt|METHOD FOR THE PRODUCTION OF CARBONIC ACID CYANIDES|
    US5352827A|1989-05-19|1994-10-04|Atochem|Synthesis of acyl cyanides in a hydrous reaction medium|
    FR2647110B1|1989-05-19|1991-07-26|Atochem|PROCESS FOR THE SYNTHESIS OF ACYLATE CYANIDES|
    US5352826A|1989-05-19|1994-10-04|Atochem|Synthesis of acyl cyanides in an anhydrous reaction medium|
    FR2647109B1|1989-05-19|1991-07-26|Atochem|PROCESS FOR THE PREPARATION OF ACYLATE CYANIDES IN ANHYDROUS MEDIA|
    DE102005027149A1|2005-06-11|2006-12-14|Lanxess Deutschland Gmbh|Process for the preparation of substituted benzoyl cyanides|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE2624891A|DE2624891C2|1976-06-03|1976-06-03|Process for the production of benzoyl cyanide|
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