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    • 1. 发明授权
      US4076758A Synthesis of vicinal glycols 失效
    • Synthesis of vicinal glycols
    • 邻二醇的合成
    • US4076758A
    • 1978-02-28
    • US749127
    • 1976-12-09
    • Dennis C. Owsley , Jordan J. Bloomfield
    • Dennis C. Owsley , Jordan J. Bloomfield
    • C07C29/00 , C07B31/00 , C07B37/04 , C07B51/00 , C07C27/00 , C07C29/128 , C07C29/32 , C07C31/20 , C07C33/26 , C07C67/00 , C07F7/18 , C07C31/14
    • C07F7/1896 , C07C29/128 , C07C29/32 , C07F7/1892 , Y02P20/55
    • Relatively low molecular weight primary alcohols are coupled to form relatively higher molecular weight vicinal glycols in which a trialkylsilyl protecting group is employed on the hydroxyl position of said low molecular weight primary alcohol during said coupling reaction.BACKGROUND OF THE INVENTIONThis invention relates to the production of vicinal glycols from starting molecules having fewer carbon atoms such as, for example, the preparation of ethylene glycol and glycerol from methanol. More particularly, this invention is concerned with the coupling of relatively low molecular weight or short chain primary alcohols to form relatively higher molecular weight or vicinal glycols by employing a trialkylsilyl protecting group on the hydroxyl position of said low molecular weight primary alcohol.In view of the fuel and mineral shortages facing the world, particularly petroleum feedstocks, there is a scarcity of vital building blocks such as ethylene and propylene used to synthesize many modern chemical entities. Consequently, alternate carbon sources for the chemical industry's basic organic chemicals must be developed for future needs from either coal or single carbon molecules such as carbon monoxide, carbon dioxide or methanol.Two major products produced from petroleum-derived feedstocks such as ethylene and propylene are, respectively, ethylene glycol and glycerol. Ethylene glycol is widely used for antifreeze and in numerous nonantifreeze outlets, including cellophane, polyester fibers and films, and polyglycols. Glycerol finds wide use in cosmetics, dentifrices, drugs and pharmaceuticals, alkyd resins, cellophane and in tobacco as a humectant and in the manufacture of plasticizers for cellulose cigarette filters.In the production of ethylene glycol, ethylene oxide is usually first prepared by direct oxidation of ethylene or by the chlorohydrin synthesis and the ethylene oxide is then reacted with water to make ethylene glycol.Although glycerol is a natural by-product of soap manufacture, a significant quantity of synthetic glycerin also is prepared from propylene. One such process involves the chlorination of propylene to allyl chloride, conversion into epichlorohydrin, and thence into glycerin. Another process involves oxidation of propylene to acrolein, conversion into allyl alcohol, then reaction with hydrogen peroxide to yield glycerin. In a third process, propylene oxide is catalytically converted into allyl alcohol, which is treated with peracetic acid to yield glycidol. Glycidol then combines with water to make glycerin.An improved method of producing vicinal glycols such as, for example, ethylene glycol and glycerol, from shorter chain molecules such as, for example, methanol, instead of employing petroleum-derived feedstocks such as ethylene and propylene, would provide significant advantages over prior methods of production.BRIEF DESCRIPTION OF THE INVENTIONIn accordance with the present invention, vicinal glycols are produced from starting molecules having fewer carbon atoms. In particular, relatively low molecular weight or short chain primary alcohols are coupled to form relatively higher molecular weight vicinal glycols by employing a trialkylsilyl protecting group on the hydroxyl position of said low molecular weight primary alcohol.As used herein, the term "trialkylsilyl" means a group containing a silicon atom bonded to three alkyl radicals, any of which can be the same as, or different than, any other.The process of this invention involves the oxidative or dehydrogenative coupling of the shorter chain primary alcohol without over-oxidation to undesirable by-products, for example, aldehydes. The initial dehydrogenation of the shorter chain primary alcohol is thus made to take place on the carbon rather than the hydroxyl group by using the trialkylsilyl blocking group on the hydroxyl. Alcoholysis of the coupled reaction product then readily yields the desired vicinal glycol.The coupling reaction of this invention is briefly illustrated by the preparation of ethylene glycol and glycerol from methanol. In order to produce ethylene glycol, two trialkylsilyl blocked methanol molecules are reacted to form 1,2-bis(trialkylsiloxy)ethane which, upon methanolysis, yields ethylene glycol. In order to produce glycerol, three trialkylsilyl blocked methanol molecules are reacted to form 1,2,3-tris(trialkylsiloxy)propane which, upon methanolysis, yields glycerol.The above process has definite advantages over the direct coupling of methanol to ethylene glycol and glycerol. This process has a higher selectivity for ethylene glycol and glycerol and less by-product is produced. That the direct coupling of methanol undesirably leads to a substantial amount of formaldehyde is seen from the work of Schwetlich et al, Angew. Chem. 72, 779 (1960); and Ladygin and Saraeva, Kinetics and Catalysis 6, 189-95 (1965) and 7, 832-39 (1966).
    • 将相对低分子量的伯醇偶联以形成相对较高分子量的邻位二醇，其中在所述偶联反应期间在所述低分子量伯醇的羟基位置上使用三烷基甲硅烷基保护基。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 5. 发明授权
      US4189611A Ortho-nitrophenylethylene glycols 失效
    • Ortho-nitrophenylethylene glycols
    • 正硝基苯乙二醇
    • US4189611A
    • 1980-02-19
    • US913905
    • 1978-06-08
    • Donnie J. Sam
    • Donnie J. Sam
    • C07C205/19 , C07D517/16 , C08G2/30 , C07C31/14 , G03C1/68
    • C07D517/16 , C07C205/19 , C08G2/30
    • Substituted dioxolanes are provided having the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or a phenyl group substituted with up to 5 substituents of lower alkyl or nitro, with the proviso that at least one of R.sup.1 and R.sup.2 is a phenyl group having an orthonitro substituent; and R.sup.3 and R.sup.4 are each H or lower alkyl. These dioxolanes, as well as appropriate dioxanes, are used to intercalate a polyoxymethylene polymer to make such a polymer having thermally stable but photochemically sensitive and degradable random linkages ##STR2## in the chain where n is 0 or 1, R.sup.3 and R.sup.4 are H or lower alkyl and at least one of R.sup.1 and R.sup.2 is a phenyl group with an orthonitro substituent. By exposing a film of the polymer to light through a transparency followed by heating or a heated treatment with base, a relief image of the copy on the transparency is obtained.
    • 提供了具有下式的取代的二氧戊环：其中R 1和R 2是H或被多至5个低级烷基或硝基的取代基取代的苯基，条件是R 1和R 2中的至少一个是具有甲基硝基的苯基 取代基; 并且R 3和R 4各自为H或低级烷基。 这些二氧戊环以及适当的二恶烷用于插入聚甲醛聚合物以制备这样的聚合物，其在n为0或1的链中具有热稳定但光化学敏感和可降解的无规键连接，其中R 3和R 4为H或 低级烷基，R 1和R 2中的至少一个为具有邻硝基取代基的苯基。 通过使聚合物的膜通过透明体曝光，然后加热或用碱进行加热处理，获得透明物上的拷贝的浮雕图像。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Global Dossier Espacenet 法律信息 同族专利 专利引用
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