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    Process for the catalytic dealkoxylation of 1,1,3-trialkoxy-2-methyl-butane
    2.
    发明授权
    Process for the catalytic dealkoxylation of 1,1,3-trialkoxy-2-methyl-butane 失效
    1,1,3-三烷氧基-2-甲基 - 丁烷的催化脱烷基化方法

    公开(公告)号：US5990360A

    公开(公告)日：1999-11-23

    申请号：US76772

    申请日：1998-05-12

    申请人： Bruno Burdet ,  Paul Nosberger ,  August Ruttimann

    发明人： Bruno Burdet ,  Paul Nosberger ,  August Ruttimann

    IPC分类号： B01J21/06 ,  C07B61/00 ,  C07C41/28 ,  C07C41/54 ,  C07C45/42 ,  C07C45/51 ,  C07C45/63 ,  C07C47/24 ,  C07C69/63

    CPC分类号： C07C41/54 ,  C07C41/28 ,  C07C45/515 ,  C07C67/11

    摘要： A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CHO [I], wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH-C (CH.sub.3).dbd.CH-OR.sup.1 [II], wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CH (OR.sup.1)(OR.sup.2) [III] to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus manufactured .gamma.-halotiglic aldehyde for the production of .gamma.-acetoxy-tiglic aldehyde or of a Wittig aldehyde halide Hal-Ph.sub.3 P.sup.+ CH.sub.2 -CH.dbd.C(CH.sub.3)-CHO [VII], wherein Hal signifies chlorine or bromine and Ph a process for the catalytic dealkoxylation of the 1,1,3-trialkoxy-2-methyl-butane CH.sub.3 -CH(ORl)-CH(CH.sub.3)-CH(OR.sup.1).sub.2 [VI] to the corresponding 1-alkoxy-2-methyl-1,3-butadiene II in the gas phase using an aluminium silicate of medium specific surface as the catalyst. The products I, .gamma.-acetoxy-tiglic aldehyde and VII are known, important intermediates for the production of various apocarotenoids and diapocarotenoids as well as of Vitamin A.

    摘要翻译： 用于制备γ-卤代醛HalH2C-CH = C（CH3）-CHO [I]的新方法，其中Hal表示氯或溴，包括1-烷氧基-2-甲基-1,3-丁二烯H 2 C的卤代烷氧基化 = CH-C（CH 3）= CH-OR 1 [II]，其中R 1表示C 1-4 - 烷基，使用特定的卤化剂在C 1-4链烷醇（R 2 OH）中并水解由此得到的γ-卤代二烷基 缩醛HalH2C-CH = C（CH3）-CH（OR1）（OR2）[III]到所需的γ-氯 - 或γ-溴代醛I.本方法中使用的卤化剂选自碱金属次氯酸盐， 碱金属次溴酸盐，碱土金属次氯酸盐，碱土金属次溴酸盐，叔丁基次氯酸盐，N-溴乙酰胺，1,3-二氯-5,5-二甲基乙内酰脲和1,3-二溴-5,5-二甲基乙内酰脲。 本发明的其它方面是使用如此制备的γ-卤代醛用于制备γ-乙酰氧基 - 四氢呋喃或维蒂希醛卤化物Hal-Ph 3 P + CH 2 -CH = C（CH 3）-CHO [VII] 其中Hal表示氯或溴，Ph表示1,1,3-三烷氧基-2-甲基 - 丁烷CH 3 -CH（OR 1）-CH（CH 3）-CH（OR 1）2 [VI]的催化脱烷基化方法， 使用中等比表面积的硅酸铝作为催化剂，在气相中与相应的1-烷氧基-2-甲基-1,3-丁二烯II反应。 产物I，γ-乙酰氧基 - lic醛和Ⅶ是已知的，用于生产各种类胡萝卜素和二糖皮质素以及维生素A的重要中间体。

    Process for the manufacture of a gamma-halotiglic aldehyde
    3.
    发明授权
    Process for the manufacture of a gamma-halotiglic aldehyde 失效
    制备γ-卤代醛的方法

    公开(公告)号：US5786518A

    公开(公告)日：1998-07-28

    申请号：US904523

    申请日：1997-08-01

    申请人： Bruno Burdet ,  Paul Nosberger ,  August Ruttimann

    发明人： Bruno Burdet ,  Paul Nosberger ,  August Ruttimann

    IPC分类号： B01J21/06 ,  C07B61/00 ,  C07C41/28 ,  C07C41/54 ,  C07C45/42 ,  C07C45/51 ,  C07C45/63 ,  C07C47/24 ,  C07C69/63 ,  C07C45/00

    CPC分类号： C07C41/54 ,  C07C41/28 ,  C07C45/515 ,  C07C67/11

    摘要： A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CHO �I!, wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH--C(CH.sub.3).dbd.CH--OR.sup.1 �II!, wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CH(OR.sup.1)(OR.sup.2) �III! to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus-manufactured .gamma.-halotiglic aldehyde for the production of .gamma.-acetoxy-tiglic aldehyde or of a Wittig aldehyde halide Hal-Ph.sub.3 P.sup.+ CH.sub.2 --CH.dbd.C(CH.sub.3)--CHO �VII!, wherein Hal signifies chlorine or bromine and Ph signifies phenyl, as well as a process for the catalytic dealkoxylation of the 1,1,3-trialkoxy-2-methyl-butane CH.sub.3 --CH(OR.sup.1)--CH(CH.sub.3)--CH(OR.sup.1).sub.2 �VI! to the corresponding 1-alkoxy-2-methyl-1,3-butadiene II in the gas phase using an aluminium silicate of medium specific surface as the catalyst. The products I, .gamma.-acetoxy-tiglic aldehyde and VII are known, important intermediates for the production of various apocarotenoids and diapocarotenoids as well as of Vitamin A.

    摘要翻译： 用于制备γ-卤代醛HalH2C-CH = C（CH3）-CHO [I]的新方法，其中Hal表示氯或溴，包括1-烷氧基-2-甲基-1,3-丁二烯H 2 C的卤代烷氧基化 = CH-C（CH 3）= CH-OR 1 [II]，其中R 1表示C 1-4 - 烷基，使用特定的卤化剂在C 1-4链烷醇（R 2 OH）中并水解由此得到的γ-卤代二烷基 缩醛HalH2C-CH = C（CH3）-CH（OR1）（OR2）[III]到所需的γ-氯 - 或γ-溴代醛I.本方法中使用的卤化剂选自碱金属次氯酸盐， 碱金属次溴酸盐，碱土金属次氯酸盐，碱土金属次溴酸盐，叔丁基次氯酸盐，N-溴乙酰胺，1,3-二氯-5,5-二甲基乙内酰脲和1,3-二溴-5,5-二甲基乙内酰脲。 本发明的其它方面是使用如此制备的γ-卤代醛用于制备γ-乙酰氧基 - 四氢呋喃或维蒂希醛卤化物Hal-Ph 3 P + CH 2 -CH = C（CH 3）-CHO [VII ]，其中Hal表示氯或溴，Ph表示苯基，以及1,1,3-三烷氧基-2-甲基 - 丁烷CH3-CH（OR1）-CH（CH3）-CH（CH）的催化脱烷基化方法 （OR1）2 [VI]与相应的1-烷氧基-2-甲基-1,3-丁二烯II在气相中使用中等比表面积的硅酸铝作为催化剂。 产物I，γ-乙酰氧基 - lic醛和Ⅶ是已知的，用于生产各种类胡萝卜素和二糖皮质素以及维生素A的重要中间体。

    Alpha-tocopherol intermediates
    6.
    发明授权
    Alpha-tocopherol intermediates 失效
    α-生育酚中间体

    公开(公告)号：US4663470A

    公开(公告)日：1987-05-05

    申请号：US919729

    申请日：1986-10-16

    申请人： August Ruttimann

    发明人： August Ruttimann

    IPC分类号： C07C45/00 ,  C07C46/00 ,  C07C46/10 ,  C07C50/06 ,  C07C67/00 ,  C07D303/32 ,  C07D311/72

    CPC分类号： C07D303/32 ,  C07C46/00 ,  C07C50/06

    摘要： A novel process for the manufacture of quinone derivatives which are suitable as intermediates for the manufacture of (2RS,4'R,8'R)-tocopherol is described. In this process a quinone of the formula ##STR1## is reacted with a phytyl derivative of the formula ##STR2## If desired, the thus-obtained compound of the formula ##STR3## is subsequently converted into the compound of the formula ##STR4## and, if desired, this compound is converted into the compound of the formula ##STR5## The compound of formula V is known and can be converted into (2RS,4'R,8'R)-tocopherol in a known manner.

    摘要翻译： 描述了适合作为制备（2RS，4'R，8'R） - 生育酚的中间体的醌衍生物的新方法。 在该方法中，将式I的醌与下式的植酰基衍生物反应。如果需要，由此得到的式III的化合物随后转化为式 如果需要，将该化合物转化为下式的化合物。式V化合物是已知的并且可以以已知的方式转化为（2RS，4'R，8'R） - 生育酚 方式。

    Manufacture of retinoids
    7.
    发明申请
    Manufacture of retinoids 失效

    公开(公告)号：US20050014976A1

    公开(公告)日：2005-01-20

    申请号：US10494079

    申请日：2002-10-24

    申请人： Alexander Radspieler ,  August Ruttimann

    发明人： Alexander Radspieler ,  August Ruttimann

    IPC分类号： C07C45/69 ,  C07C47/225 ,  C07C47/38 ,  C07C403/08 ,  C07C403/10 ,  C07C403/14

    CPC分类号： C07C403/14 ,  C07B2200/09 ,  C07C403/04 ,  C07C403/08 ,  C07C403/10 ,  C07C403/12 ,  C07C403/22 ,  C07C2601/16

    摘要： A process for the manufacture of retinal (I) comprises reacting a 5-(2,6,6-trimethyl-cyclohex-1-enyl)-1,4-pentadiene derivative (IIa) or a 5-(2,6,6-trimethyl-cyclohex-2-enyl)-1,4-pentadiene derivative (IIb) or a 5-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-1-pentene derivative (IIc) or a 5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-1-en-4-yne derivative (IId) or a 5-(2,6,6-trimethyl-cyclohex-2-enyl)-penta-1-en-4-yne derivative (IIe) with a 1,3-butadiene derivative H2C═C(CH3)CCH═CHOR4 (III) in the presence of a Lewis or Brönsted acid and subjecting the compound obtained in each case [(IVa), (IVb), (IVc), (IVd) or (IVe), respectively] to basic or acidic conditions to eliminate therefrom the moiety R2H and thus produce, according to the immediate precursor, retinal itself or a particular derivative thereof [(I′), (I′), (Va) or (Vb), respectively] and, where in two cases such derivative is produced featuring a triple bond [derivative (Va) or (Vb)], hydrogenating this to produce retinal (I) or the derivative (I′), respectively, and each case where a derivative (I′) or (I′) has been produced, isomerizing this under basic or acidic conditions or in the presence of a metal catalyst to the desired retinal (I). The so-produced retinal is usually in the form of an isomeric mixture, normally as (9 E/Z, 13 E/Z)-retinal, and this can be isomerized according to a further inventive aspect to (all-E)-retinal by the acid-catalysed formation of an adduct of (all-E)-retinal with hydroquinone in crystalline form. The so obtained (all-E)-retinal-hydroquinone adduct can then if desired be converted to vitamin A alcohol in the predominantly (all-E)-isomeric form by a method known per se. The novel starting materials (IIa), (IIb), (IIc), (IVI) and (IIe) represent a still further inventive aspect. Retinal is a valuable intermediate in the synthesis of further vitamin A compounds (retinoids). The retinoids, particularly vitamin A alcohol (retinol), are known to be valuable substances which promote the well-being of humans, inter alia in respect of vision, the immune system and growth, and for this reason are often used as components of multivitamin preparations and as additives for certain food- and feedstuffs.

    Manufacture of polyene aldehydes
    8.
    发明授权
    Manufacture of polyene aldehydes 失效
    多烯醛的制造

    公开(公告)号：US6153769A

    公开(公告)日：2000-11-28

    申请号：US193935

    申请日：1998-11-17

    申请人： August Ruttimann

    发明人： August Ruttimann

    IPC分类号： B01J31/02 ,  C07B61/00 ,  C07C45/59 ,  C07C45/67 ,  C07C47/21 ,  C07C403/14 ,  C07D317/08 ,  C07D317/12 ,  C07D317/22 ,  C07D317/26

    CPC分类号： C07D317/22 ,  C07C403/14 ,  C07C45/59 ,  C07C45/673 ,  C07D317/12 ,  C07C2101/16

    摘要： A process for the manufacture of polyene aldehydes comprises reacting a polyene O,O-ethylene acetal with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or Bronsted acid, hydrolyzing the resulting condensation product and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel polyene O,O-ethylene acetals as well as the likewise novel condensation products in this process form further aspects of the invention. The final products are primarily carotenoids which find corresponding use, e.g. as colorants and pigments for foodstuffs, animal products etc.

    摘要翻译： 制备多烯醛的方法包括使多烯O，O-乙烯缩醛与1-烷氧基-1,3-二烯在路易斯酸或Br + E，uml + EE nsted酸的存在下反应，水解 得到的缩合产物并在碱性或酸性条件下从在此阶段产生的多烯衍生物中除去醇。 在该方法中新型多烯O，O-乙缩醛以及同样新颖的缩合产物形成本发明的其它方面。 最终产品主要是类胡萝卜素，其可以找到相应的用途，例如 作为食品，动物产品等的着色剂和颜料

    Process for manufacturing polyene aldehydes
    9.
    发明授权
    Process for manufacturing polyene aldehydes 失效
    制造多烯醛的方法

    公开(公告)号：US5929288A

    公开(公告)日：1999-07-27

    申请号：US865288

    申请日：1997-05-29

    申请人： August Ruttimann

    发明人： August Ruttimann

    IPC分类号： C07C45/45 ,  C07B61/00 ,  C07C43/303 ,  C07C45/51 ,  C07C45/67 ,  C07C47/21 ,  C07C47/26 ,  C07C47/277 ,  C07C403/14 ,  C07C45/60

    CPC分类号： C07C403/10 ,  C07C403/14 ,  C07C43/303 ,  C07C45/513 ,  C07C45/515 ,  C07C45/673 ,  C07C47/277 ,  C07C2101/16

    摘要： To manufacture polyene aldehydes and polyene dialdehydes a polyene O,O-dialkyl acetal or polyene di(O,O-dialkyl acetal) is reacted with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or a Bronsted acid. The reaction mixture is then hydrolyzed and the alcohol is cleaved under basic conditions from the polyene derivative produced by the reacting. Those intermediates in this process from which the alcohol is to be cleaved are novel. The final products are primarily carotenoids which can be used as colorants and pigments for foodstuffs, animal products, and the like.

    摘要翻译： 为了制备多烯醛和多烯二醛，多烯O，O-二烷基缩醛或多烯二（O，O-二烷基缩醛）与1-烷氧基-1,3-二烯在路易斯酸或Br + E，uml o + EE nsted酸。 然后将反应混合物水解，并在碱性条件下将醇从通过反应产生的多烯衍生物裂解。 在该方法中这种醇被切割的那些中间体是新的。 最终产品主要是可用作食品，动物产品等的着色剂和颜料的类胡萝卜素。