• 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:
    (2,2-Dimethyl-1,2-dihydroquinoline-4-yl)-methylsulfonic acid and the ammonium, alkali metal, alkali earth metal and zinc salts thereof are disclosed. The new compound and its salts are superior antioxidants useful to stabilize animal feedstuffs containing biologically active substances which are sensitive to oxidation.
    公开号:SU888818A3
    申请号:SU802884428
    申请日:1980-02-20
    公开日:1981-12-07
    发明作者:Амбруш Деже；Саболочи Тамаш；Хуташ Иштван
    申请人:Хинсин Дьедьсер Еш Ведьесети(Фирма)；
    IPC主号:
    专利说明:

    oxides, carbonates of mono- and divalent cations; and ammori salts, alkali metal and alkaline earth metal salts, such as sodium, potassium, magnesium, calcium, and other metal salts, such as iron and zinc salts. The following method was used to isolate the salts: the reaction mixture was poured onto ice and, after extraction with acetone, concentrated. For the purpose of subsequent purification, the salts are recrystallized. Free sulphonic acid is separated from its salt using a cation-exchange resin. The starting product: 2,2,4-trimethyl-1, -dihydroquinoline is obtained by reacting 1 mole of aniline and 2 moles of acetone in the presence of an iodine-containing catalyst. When comparing the effects of the described compounds and known antioxidants, for example, 2,6-di-tert-butyl-4-methyl-phenol, methylene bis- (2,2,4-trimethyl-1,2-dihydroquinoline), ethoxyquin, It has been shown that the described compounds have a higher antioxidant activity than the known antioxidants. The studies performed do not reveal a residual effect on the home of the food-fed poultry, but also the following: Chemical shift: 6.66-7.5:
    Multiple Singlet
    N N Na O
    6.07 4.25 6.99 29.17
    5.91 4.23 7.00 Calculated 16.4 Found 16
    Example 2. 23.3 g (O, 2 mol) of chlorosulfonic acid are dissolved in 40 ml of carbon tetrachloride and 17.3 g (0.1 mol) of 2,2,4-trimethyl- is added to the resulting solution at 0 ° C. 1, 2-dihydroquinoline. The mixture was kept at 40 ° C for 4 hours, and then treated as described in Example 1. The quality of the product obtained (28.8 g) corresponds to the product of Example 1. The yield is 87.5%.
    Example. 3. Obtained after the sulfonation carried out under the conditions of Example 2, the mixture is poured onto ice and the acidic solution is neutralized with 5N sodium hydroxide solution. The volume of the solution is adjusted to 650 ml by addition of a 35% aqueous solution.
    5.9
    4.1
    1.33
    S 9,72
    9.53
    pa calcium acetate. The suspension thus formed is mixed with 500 ml of acetone. The phases are separated. The acetone phase is further treated under the conditions described in Example 1. Calcium salt (2,2-dimethyl-1, 2-dihydroquinolin-4-yl) methylsulfonic acid is obtained in a yield of 29.9 g (86.6%). Mpd 72-75 ° С. Potassium content: Calculated,% 11.3 Found,% 11.1 Water content: Calculated,% 15.6
    0Found% 15.3
    Example 4. A solution of 6.5 g of sodium salt (2,2-dimethyl 5 1 2-dihydroquinolin-4-yl) -methylsulbilized with the described sulfo-acid sulphate is introduced on a column with 120 g of cation-exchange artificial resin 50x10 in the H-form. The compounds described do not accumulate in the animals and are rapidly excreted. Due to the fact that the described compounds have a stabilizing effect on the feed, the animals gain weight. Example 1. To 20 ml of carbon tetrachloride with stirring the institute, add 32 ml of concentrated sulfuric acid. The solution is cooled before and 17.3 g (0.1 mol) of 2,2,4-trimethyl-1,2-dihydroquinoline is introduced into it, and the reaction mixture is maintained for 4 hours. The two phases thus obtained are separated. The lower phase is extracted with 40 ml of carbon tetrachloride, the organic layer is poured onto ice and 2x100 ml of 5N is added to the mixture successively. and 150 ml 10 n. sodium hydroxide solution and make up to 650 ml. The alkaline solution is extracted with acetone. The acetone phase is concentrated in vacuo and the resulting dark oil is poured onto ethyl acetate. The suspension obtained is stirred for 1 hour, dried, washed with a mixture of ethyl acetate and methanol and dried in the dark. 21.5 g (76%) of sodium salt of (2,2-dimethyl-1, 2-dihydroquinolin-4-yl) methyl sulphonic acid are obtained. T pl 66-68 C.
    phacid with 3 mol of water of crystallization in 20 ml of water. The column is washed with distilled water and the eluate is concentrated. The precipitated product is filtered off, washed with ethyl acetate and dried at room temperature. Get 4.5 g. (2,2-dimethyl-1,2-dihydroquinOL-4-IL) -methylsulfonic acid. Yield: 88%. TPA 25b-260 ° C.
    Example 5. To a solution of 13.2 sodium salt of (2,2-dimethyl-1,2-dihydroxinolin-4-yl) methyl methylphosphonic acid in 10 ml of methanol was added 2.7 g of zinc chloride. The mixture was stirred at room temperature for 2 hours and diluted with 40 ml of water. The solution is concentrated in vacuo, heating in a water bath.
    9.9 g of zinc salt of (2,2-dimethyl-1,2-dihydroquinolin-4-yl) methyl sulphonic acid are obtained. Yield 87%
    98-100s
    pl
    权利要求:
    Claims (4)
    [1]
    1. The method of producing (2,2-dimethyl-1, 2-dihydroquinoline-4-IL) -methylsulfonic acid or its salts, about tl and the fact that 2,2,4-trimethyl-1, 2-dihydroquinoline is administered in the interaction with the sulfating agent at a temperature of from 20 to 80 ° C, followed by separation of the target product or in free form, or in the form of a salt.
    [2]
    2. The method according to claim 1, wherein the sulfonation is carried out at a temperature of from 35 to 45 ° C.
    [3]
    3. Method according to paragraphs. 1 and 2, which is based on the use of such agents as sulfuric acid, chlorosulfonic acid as a sulphating agent.
    [4]
    4. Method according to paragraphs. 1-3, characterized in that the sulfonation is carried out in an organic solvent, such as carbon tetrachloride.
    Sources of information taken into account in the examination
    1. Weigand-Hilgetag. Methods of experiment in organic chemistry, M., ed. Chemistry, 1968, p. 559.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2562970A|1950-04-14|1951-08-07|Thompson Chester Ray|Preservation of forage crops|
    US3024217A|1959-06-25|1962-03-06|Firestone Tire & Rubber Co|Rubber antioxidant|
    DE1492900A1|1963-08-07|1970-08-27|
    US3347677A|1966-04-01|1967-10-17|Monsanto Co|Activated dihydroquinolines|DK328483D0|1983-07-15|1983-07-15|Magius N W Von|ETHOXYQUINSALTE|
    GB8816269D0|1988-07-08|1988-08-10|Int Assn Of Fish Meal Manufact|Compounds for use as anti-oxidants in fish meal/fish oil|
    US5202338A|1990-10-31|1993-04-13|Vilmos Bar|Dihydroquinoline derivatives, pharmaceutical compositions and methods of use of dihydroquinoline derivatives as modulators of the arachidonic acid cascade|
    AU2003302176A1|2002-12-18|2004-07-09|Ciba Specialty Chemicals Holding Inc.|Antioxidant for fats, oils and food|
    DE10329860A1|2003-07-02|2005-01-20|Atto-Tec Gmbh|Sulfonamide derivatives of polycyclic dyes for analytical applications|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    HU79CI1916A|HU182010B|1979-02-21|1979-02-21|Novel 2,2-dimethyl-1,2-dihydro-quinoline derivatives having anti-oxidant activity|
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