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    • 54. 发明授权
      US4339611A Process for selective formation of C.sub.4 compounds and organic sulfide-containing catalyst system used therein 失效
    • Process for selective formation of C.sub.4 compounds and organic sulfide-containing catalyst system used therein
    • 用于选择性形成C4化合物和其中使用的含有机硫化物的催化剂体系的方法
    • US4339611A
    • 1982-07-13
    • US215556
    • 1980-12-11
    • Wayne R. Pretzer , Thaddeus P. Kobylinski , John E. Bozik
    • Wayne R. Pretzer , Thaddeus P. Kobylinski , John E. Bozik
    • B01J27/043 , B01J31/20 , C07C29/32 , C07C45/49 , C07C27/22 , C07C45/50
    • B01J31/2234 , B01J27/043 , B01J31/0218 , B01J31/0231 , B01J31/20 , B01J31/26 , C07C29/32 , C07C45/49 , B01J2231/34 , B01J2231/641 , B01J2531/845 , Y02P20/52
    • C.sub.4 compounds including n-butanol and n-butanal are produced by reacting methanol, hydrogen, and carbon monoxide, in the presence of a cobalt catalyst selected from the group consisting of (a) a cobalt carbonyl, (b) a hydrido cobalt carbonyl and (c) a cobalt-containing material convertible to a cobalt carbonyl or a hydrido cobalt carbonyl, an iodine promotor and an organic sulfide having the formula:R.sub.1 --S--R.sub.2wherein R.sub.1 and R.sub.2 can be the same or different members selected from the group consisting of saturated or unsaturated, straight or branched chain alkyl radicals having from one to 24 carbon atoms, cycloalkyl radicals having from three to 40 carbon atoms, aryl radicals having from six to 20 carbon atoms, aralkyl and alkaryl radicals having from six to 40 carbon atoms and halogen substituted derivatives thereof. A high degree of selectivity towards the formation of butanol and butanal is provided by using the cobalt entity and the organic sulfide in a molar ratio in the range of about 2:1 to about 1:10, based on elemental cobalt and sulfur. The reaction is conducted at elevated temperature and pressure conditions for a time sufficient to convert methanol to n-butanol and n-butanal.
    • 包括正丁醇和正丁醛的C 4化合物通过甲醇，氢气和一氧化碳在钴催化剂存在下制备，所述钴催化剂选自（a）羰基钴，（b）羰基钴和 （c）可转化为羰基钴或羰基钴的钴的物质，碘促进剂和有机硫化物，其具有下式：R1-S-R2，其中R1和R2可以是相同或不同的选自基团 由具有1至24个碳原子的饱和或不饱和的直链或支链烷基，具有3至40个碳原子的环烷基，具有6至20个碳原子的芳基，具有6至40个碳原子的芳烷基和烷芳基 原子和卤素取代的衍生物。 通过使用基于元素钴和硫的摩尔比在约2:1至约1:10范围内的钴实体和有机硫化物来提供对形成丁醇和丁醛的高度选择性。 反应在升高的温度和压力条件下进行足以将甲醇转化为正丁醇和正丁醛的时间。
    • 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
    • 58. 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
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