• 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:
    The invention relates to amino acids, in particular the preparation of methionine, which is used in organic synthesis. To increase the methionine yield, the hydrolysis of 5- (B-methyl-mercapto-ethyl) -hydantoin is carried out by heating under pressure in the presence of sodium or potassium hydroxide, or potassium bicarbonate, taken at a certain molar ratio equal to
    公开号:SU1311619A3
    申请号:SU843792608
    申请日:1984-09-26
    公开日:1987-05-15
    发明作者:Больце Рудольф；Гайгер Фридхельм；Шпиндлер Манфред；Таннер Херберт
    申请人:Дегусса Аг (Фирма)；
    IPC主号:
    专利说明:

    Methionine production
     The purpose of the invention is to increase the yield of the target product.
    Example 1. A solution of 60 g of 5- - (B-methylmercaptoethyl) -hydantoin (0.34 mol) and 0.34 mol of sodium hydroxide in 220 ml of water is mixed with 23 ml (0.34 mol) of a concentrated ammonia solution and in a stirred mixer A 500 ml high-grade steel autoclave is heated for 4 hours at 165 ° C. After the reaction has passed under its own pressure, the mixture of products is cooled down, 320 ml, and heated in an autoclave for 4 hours, the pressure is released and relieved. The yield of methion is 165 ° C. The yield of methionine Compound from sodium methionite solution is 92.5%. It is 92.6%. If the reaction is carried out when the reaction is carried out under such equal conditions, but instead of ammonia conditions, however, 0.35 mol of bicarbonate is added without the addition of ammonia.
    Since the gaseous compounds formed during the reaction remain in the autoclave, methionine is obtained in a yield of 75.8%.
    (1.7 mol) of a concentrated ammonia solution and heated in an autoclave for 4 hours at 160 s. The yield of methionine is 76.0%, along with a yield of 18.1% of dimeric methionine (N-methionylmethionine).
    If the reaction is carried out under other equal conditions but without the addition of ammonia, methionine is formed in 64.5% yield along with a yield of 21.0% dimeric methionine (N-methionylmethionine).
    Example 2. A solution of 0.34 mol 25 and 0.31 mol of a solution of sodium hydroxide- 5- (y-methyl mercaptoethide) -hydantoin ri, in 200 ml of water is mixed with 115 ml and 0.34 mol of potassium hydroxide in 180 ml of water is mixed with 5 mol of concentrated ammonia solution and heated in an aktoklave with a capacity of 1000 tm for 4 hours at 160 ° C. After the end of the reaction under pressure, methionine with a 95.6% yield is taken from potassium methioninate.
    If the reaction is carried out under the same conditions, but without the addition of ammonia, methionine is formed in 71.1% yield.
    Example 3. A solution of 0.34 mol of 5- (B-methylmercaptoethyl) -hydantoin and 0.34 mol of potassium bicarbonate in 200 MP of water is mixed with 70 ml (1 mol of concentrated ammonia solution) and heated in an autoclave for 3 hours at 170 ° WITH. After the usual treatment, methionine is obtained with a yield of 93.4%.
    If the reaction is carried out under the same conditions but without the addition of ammonia, methionine is formed in 74.3% yield.
    Example 4. A solution of 0.34 mol of 5- (B-methylmercaptoztil) -hydantoin and
    40
    Example 7. A solution of 174.2 kg (1-kmol) 5- (B-methylmerpatoethyl) -hydantoin, prepared in the usual way, is hourly supplied to the head of the pressure-resistant column hourly.
    5 to 260 kg of water, and also 80 kg of 50% (1 kmol) of sodium hydroxide solution. At the same time, 34.1 kg / h (2 kmol) of gaseous ammonia are blown into the bottom of the column and the reaction temperature is set at 160 ° C. Ammonia, carbon dioxide and water vapor are removed from the head of the column through the valve to maintain the head. The yield of pressure lower than 0. 51 mol of sodium hydroxide in 220 ml of th from the bottom of the column of the hydrolysis plant is mixed with 1 mol of ammonia and heated in an autoclave for 4 hours at 160 ° C. The methionine yield is 97.4%.
    that and cool it. The methionine yield is 97.0%.
    If continuous saponification is carried out under other equal conditions.
    Under the same conditions, but without the addition of ammonia, methionine is formed in 84.8% yield.
    Example 5. To the crude 5- (B-methylmercaptoethyl) -hydantoin, which contains 0.34 mol of hydantoin and is prepared in the usual way by reacting 3-methylmercaptopropionaldehyde with ammonium bicarbonate and hydrocyanic acid, 0.34 mol of NaOH and 0 are added 34 mol of concentrated ammonia solution. The mixture is filled with water to a volume of about
    ammonium, methionine yield of 71.6%.
    Example 6. A solution of 0.34 mol of 5- (B-methylmercaptoethyl) -hydantoin
    (1.7 mol) of a concentrated ammonia solution and heated in an autoclave for 4 hours at 160 s. The yield of methionine is 76.0%, along with the yield of 18.1% of dimeric methionine (N-methionylmethionine).
    If the reaction is carried out under other conditions being equal, but without the addition of ammonia, methionine is formed in 64.5% yield along with 21.0% of dimeric methionine (N-methionylmethionine).
    and 0.31 mol of sodium hydroxide solution, in 200 ml of water is mixed with 115 ml
    40
    Example 7. A solution of 174.2 kg (1-kmol) 5- (B-methylmerpatoethyl) -hydantoin, prepared in the usual way, is hourly supplied to the head of the pressure-resistant column hourly.
    5 to 260 kg of water, and also 80 kg of 50% (1 kmol) of sodium hydroxide solution. At the same time, 34.1 kg / h (2 kmol) of gaseous ammonia are blown into the bottom of the column and the reaction temperature is set at 160 ° C. Ammonia, carbon dioxide and water vapor are removed from the head of the column through the valve to maintain the head. Reduce the pressure output of the shet and cool it. The methionine yield is 97.0%.
    If continuous saponification is carried out under other equal conditions.
    3131) 6194
    but without the addition of ammonia, methionine is produced with a yield and pressure in an aqueous alkaline medium with a yield of 81.2%, characterized in that, with
    As can be seen from the above examples, with the aim of increasing the yield of the target, the proposed method allows for an increase, the hydrolysis is carried out into the yield of the desired product. sodium or potassium hydroxide
    or potassium bicarbonate, taken in the formula of the invention, with a relative ratio of 0.9-1: 1-1.5,
    to hydantoin, and in the presence of additional methionine by introducing ammonia into the amount of hydrolysis of 5- (B-methyl mercaptoethyl) —On from 1 to 15 mol per 1 mol of hydanhydantoin at elevated temperatures.
    权利要求:
    Claims (1)
    [1]
    Claim
    A method of producing methionine by hydrolysis of 5- (β-methylmercaptoethyl) hydantoin at elevated temperatures of 1311619 4 re and pressure in an aqueous alkaline medium, characterized in that, in order to increase the yield of the target product, hydrolysis is carried out in the presence of sodium or potassium hydroxide or potassium bicarbonate taken in a molar ratio of 0.9-1: 1-1.5 to hydantoin, and in the presence of additionally introduced ammonia in an amount of from 1 to 15 mol per 1 mol of hydantoin.
    类似技术:
    公开号 | 公开日 | 专利标题
    CA2193161A1|1997-06-19|A process for the preparation of d,l-methionine or the salt thereof
    Gaudry1948|THE SYNTHESIS OF D, L-α-AMINO-ϵ-HYDROXYCAPROIC ACID AND A NEW SYNTHESIS OF D, L-LYSINE
    US2564649A|1951-08-14|Preparation of lysine
    EP1556343B1|2007-08-29|Process for the production of 3-methylthiopropanal
    US3636098A|1972-01-18|Process for producing methionine
    US2557913A|1951-06-19|Production of methionine
    SU1311619A3|1987-05-15|Method for producing methionine
    US5756803A|1998-05-26|Process for the condensation of an aldehyde with hydrogen cyanide
    US5663409A|1997-09-02|Process for the preparation of 3-| propanal and 2-hydroxy-4-| butanenitrile
    US3833651A|1974-09-03|Process for the preparation of dl-methionine
    SU1598867A3|1990-10-07|Method of producing 30-60% solution of sodium methyoninate
    US3536726A|1970-10-27|Preparation of alpha-amino-carboxylic acids
    US3927085A|1975-12-16|Process for the production of a mercaptocarboxylic acid
    US3668221A|1972-06-06|A process for producing {60 -amino acids
    US4230869A|1980-10-28|Process for preparing 5-|hydantoin
    US2564647A|1951-08-14|Hydantoin manufacture
    US4259525A|1981-03-31|Methionine process
    US3886209A|1975-05-27|Process for preparing alpha, omega-diaminocarboxylic acids
    US2312878A|1943-03-02|Alkali metal salts of beta-sulphopropionitrile and method of preparation
    US2225155A|1940-12-17|Preparation of amino compounds
    US3917683A|1975-11-04|Process for the preparation of DL-methionine
    US3344179A|1967-09-26|Method for synthesizing di-glutamic acid and its alkyl derivatives
    US2731480A|1956-01-17|Process for the production of epsilon-acyl lysines
    Sudo et al.1963|Reactions of alicyclic aminonitrile
    US2444023A|1948-06-29|Preparation of dimethyl urea
    同族专利:
    公开号 | 公开日
    DE3335218A1|1985-04-11|
    EP0143218B1|1988-04-06|
    ES8505649A1|1985-06-01|
    CA1226003A|1987-08-25|
    HUT36786A|1985-10-28|
    JPS6092258A|1985-05-23|
    EP0143218A2|1985-06-05|
    DE3470305D1|1988-05-11|
    EP0143218A3|1986-05-21|
    ES536179A0|1985-06-01|
    US4518801A|1985-05-21|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2557920A|1946-11-07|1951-06-19|Dow Chemical Co|Method for production of amino acids|
    US2557913A|1946-11-07|1951-06-19|Dow Chemical Co|Production of methionine|
    US2527366A|1946-11-07|1950-10-24|Dow Chemical Co|Production of amino acids|
    US3636098A|1966-07-02|1972-01-18|Sumitomo Chemical Co|Process for producing methionine|
    US3668221A|1966-07-28|1972-06-06|Sumitomo Chemical Co|A process for producing {60 -amino acids|
    US4069251A|1969-02-08|1978-01-17|Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler|Continuous process for the manufacture of methionine|
    GB1310510A|1969-06-10|1973-03-21|Zundel J|Preparation of alpha-aminoacids from hydantoins|
    JPS49818B1|1970-08-12|1974-01-10|
    JPS582227B2|1974-02-04|1983-01-14|Sumitomo Chemical Co|
    JPS5715756B2|1974-06-05|1982-04-01|
    US4272631A|1980-02-25|1981-06-09|Diamond Shamrock Corporation|Hydrolysis of 5--hydantoin|
    DE3105008C2|1981-02-12|1991-04-11|Degussa Ag, 6000 Frankfurt, De|US5338859A|1993-02-12|1994-08-16|Hoechst Celanese Corporation|Process for the production of calcium salts of hydantoic acids|
    FR2733231B1|1995-04-24|1997-07-04|Rhone Poulenc Nutrition Animal|PROCESS FOR CONDENSING CYANHYDRIC ACID WITH AN ALDEHYDE|
    DE19547236A1|1995-12-18|1997-07-03|Degussa|Process for the preparation of D, L-methionine or its salt|
    DE102008042932A1|2008-10-17|2010-04-22|Evonik Degussa Gmbh|Production and use of methionylmethionine as a feed additive for fish and crustaceans|
    DE102011081828A1|2011-08-30|2013-02-28|Evonik Degussa Gmbh|Process for the reaction of methylmercaptopropionaldehyde from crude acrolein and crude methylmercaptan|
    EP3495346A1|2017-12-07|2019-06-12|Evonik Degussa GmbH|Method for the production of calcium methioninate|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19833335218|DE3335218A1|1983-09-29|1983-09-29|METHOD FOR THE HYDROLYSIS OF 5--HYDANTOIN|
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