One-Step Conversion of Cellobiose to C6-Alcohols Using a Ruthenium

Cellobiose to C 6-Alcohols Using a Ruthenium

Nanocluster Catalyst

Ning Yan,?Chen Zhao,?Chen Luo,?Paul J.Dyson,?Haichao Liu,*,?and Yuan Kou*,?

PKU Green Chemistry Center,Beijing National Laboratory for Molecular Sciences,College of Chemistry and Molecular Engineering,Peking Uni V ersity,Beijing 100871,China,and The Institut des Sciences et Inge ′nierie

Chimiques,Ecole Polytechnique,Fe ′de ′rale de Lausanne,EPFL-BCH,CH-1015Lausanne,Switzerland

Received April 10,2006;E-mail:yuankou@https://www.wendangku.net/doc/4b17624506.html,

The one-step conversion of cellulose to C 6-alcohols via green

and energy efficient approaches has,as far as we are aware,not been reported.Such a process presents a considerable challenge,the two key problems being (1)finding a suitable solvent that dissolves the cellulose,and (2)the development of advanced catalytic chemistry for selective cleavage of the C -O -C bonds (glycosidic bonds)connecting glucose residues.The dissolution of cellulose has been recently realized by using ionic liquids as green solvents;1there is still no efficient method,such as selective hydrogenation,for the precise C -O -C cleavage under mild conditions,however.Cellobiose is a glucose dimer connected by a glycosidic bond and represents the simplest model molecule for cellulose.We disclose in this communication that the one-step conversion of cellobiose to C 6-alcohols can be realized by selectively breaking the C -O -C bonds via selective hydrogenation using a water-soluble ruthenium nanocluster catalyst under 40bar H 2pressure.

Sorbitol and glycerin,dideoxyhexitol,and trideoxyhexitol are under consideration as a new generation green energy platform,instead of syngas,to produce bio-fuels,2,3chemicals,and hydro-gen.4,5Sorbitol is generally obtained via a two-step process,that is,hydrolysis of cellulose in acidic water and then by further hydrogenation.The process,especially hydrolysis under acidic conditions,is not energy efficient and also not as green as desired.6,7Direct conversion of cellulose requires the cleavage of two C -O -C bonds,one being the 1,4- -glucoside bond connecting two adjacent glucose monomers and the other being contained in the glucose ring.It can be seen from Figure 1that the cleavage of the 1,4- -glycosidic bond may result in two different products:dehydrate-sorbitol when breaking the C 1-O bond (position a ),and dehydroxy-glucose following cleavage of the other (position b ).

To facilitate the discovery of a suitable catalyst,cellobiose was chosen as a model substrate,and four transition metals,Ru,Rh,Pd,and Pt,were examined.Metal nanoparticles were prepared by reduction of the appropriate metal salts in the presence of poly(N -vinyl-2-pyrrolidone)(PVP)in refluxing ethanol -water solution.8-11A typical micrograph of the ruthenium nanoparticles is shown in Figure 2.A narrow unimodal size distribution with a diameter of 2.4(0.4nm is observed.Rh,Pd,and Pt nanoparticles were found to have similar diameters of about 3nm under related conditions.11The hydrogenation reactions were carried out in a Parr autoclave at 120°C and 4MPa H 2,and the products were analyzed by gas chromatography (GC),high-performance liquid chromatography (HPLC),and electrospray ionization mass spectroscopy (ESI-MS).Among them (Table 1,entries 1-4),Pd nanoparticles showed no activity,due perhaps to their instability under the reaction conditions (120°C,40bar H 2).Pd black deposits were observed together with

a colorless solution at the end of the reaction.Pt and Rh both exhibited good activities in the reaction,but the selectivities were poor.Ru was the only metal that exhibited high stability under the conditions (a temperature of 120°C and a hydrogen pressure of 40bar)and gave high activity and selectivity;that is,the cellobiose was quantitatively converted to C 6-alcohols.

It is interesting to note that our previous work has proved that Rh,Pd,and Pt nanoparticles prepared by the same method are all excellent catalysts for the hydrogenation of alkenes and arenes,12with the Ru nanoparticles being completely inactive.

To delineate to what extent that a two-step process,that is,hydrolysis followed by further hydrogenation,may occur,the influence of pH on the reaction was examined.Irrespective of the pH,no product with a carbon number less than six was detected by ESI-MS,and only trace amounts (<0.2wt %)of small molecular weight alcohols,such as ethanol,were detected by GC,demonstrat-ing the high specificity of the Ru nanoparticles in hydrogenation/hydrogenolysis of C -O -C bonds.Increasing the pH from 2to 7then to 10resulted in an acceptable decrease in cellobiose conversion,but caused a dramatic change in product distribution (entries 4-6in Table 1).Sorbitol was obtained quantitatively under acidic conditions (pH )2),indicating the occurrence of a two-step process.At pH 7,3- -D -glucopyranosyl-D -glucitol (denoted

?Peking University.?

Ecole Polytechnique.

Figure 1.Cellulose structure and the potential monomers formed following cleavage of the C -O -C bonds at position a or b .

Figure 2.TEM micrographs and particle histograms of polymer-stabilized ruthenium nanoparticles isolated from water (200particles counted for the sample,scale bar )20nm).

Published on Web 06/20/2006

8714

9

J.AM.CHEM.SOC.2006,128,8714-8715

10.1021/ja062468t CCC:$33.50?2006American Chemical Society

as A in the Table),the corresponding sugar alcohol of cellobiose, is the main product(64.8%in a conversion of87.8%)and the selectivity to sorbitol decreases to26.4%.A small amount of glucose was also observed.ESI-MS and tandem MS analysis evidenced the appearance of dideoxyhexitol(7.2%).This very important“new”product was further observed in basic conditions. Under basic conditions(pH)10),the selectivity to A and sorbitol slightly decreased to79.7%,while that for the other C6-alcohols (mainly dideoxyhexitol)increased from7.2to17.1%,demonstrating the precise cleavage of the C1-O in the glycosidic bond in cellobiose.On the basis of these findings,the reaction pathways depicted in Schemes1and2are proposed.

Scheme1shows the reaction pathways in acidic media.The mechanism involves H+-promoted hydrolysis of glycosidic bonds, followed by catalytic hydrogenation of glucose to sorbitol.While in neutral and basic media(see Scheme2),the situation is quite different.The product A is simply arising from a classic hydrogena-tion of the cellobiose.The presence of a new compound with a formula of C6H14O4,which is a saturated tetraols(containing4OH groups)as demonstrated by MS analysis(see Supporting Informa-tion S2-S6and corresponding analysis),and the absence of any compound with a formula of C6H14O5or C6H12O5are indicative of the removal of the oxygen atom in the C1-O-C5bonds in combination with the cleavage of the C1-O bond involved in the glycosidic bonds.Had the C4′-O bond been broken,the principle products would have been4-dehydroxy glucose(C6H12O5)or 2-dehydroxy sorbitol(C6H14O5).Thus,dideoxyhexitol and sorbitol are the final products;that is,the experimentally observed sorbitol observed at different pH originates from different reaction pathways, as explained by the schemes.

Dispersed Ru nanoparticles,for example,supported on a surface, would reasonably expect to have a similar catalytic performance. Surprisingly,unlike that of the water-soluble Ru nanoparticles, active carbon-supported ruthenium catalyst(entry7)shows no such catalytic activity under the same reaction conditions.

In conclusion,selective cleavage of C-O bonds leading to a novel catalytic hydrogenation reaction has been realized with a Ru nanocluster catalyst.A new approach,the one-step conversion of cellobiose to C6-alcohols,can for the first time be achieved via precise cleavage of the glycosidic bonds.Preliminary investigations demonstrate that cellulose can also be converted to C6-alcohols using the Ru nanocluster catalyst in[bmim]Cl ionic liquid,and while a conversion of15%was observed,further experiments are in progress to improve the conversion.Nevertheless,the concept established in this work opens up a new opportunity for the transformation of cellulose to valuable chemicals,such as bio-fuels. Acknowledgment.This work was financially supported by the National Science Foundation of China(Project Nos.20533010, 20473002.).

Supporting Information Available:Synthesis of the ruthenium nanoparticles,and the procedures and experiment data for cellobiose hydrogenation reactions.This material is available free of charge via the Internet at https://www.wendangku.net/doc/4b17624506.html,.

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JA062468T

Selectivity(%)

entry catalyst pH conv.(%)sorbitol glucose A d

other polyols

(mainly

dideoxyhexitol)

1a Pd210001000

2a Rh2100 6.966.90

3a Pt210018.542.60

4a Ru2100100000

5a Ru7.087.826.4 1.664.87.2c

6a Ru10.075.624.0 3.255.717.1c

7b Ru/C7.0100<10>990

a Reaction conditions:metal(1.67×10-3mol/L);PVP:metal)10

(mole ratio),temperature(120°C),hydrogen pressure(40bar),reaction

time(12h),cellobiose(7.31mmol),using H2O(30g)as solvent.b Reaction

condition:the same as(a)except0.1g of1%Ru/C was used as catalyst.

c Due to the lack of standards,the data are obtaine

d by subtracting the

selectivity of glucose,sorbitol,and A from100.The reliability of the data

is ensured by the fact that no significant amount of other products(see

Supporting Information for details)was detected in either the gas or liquid

phases by IR and GC,and no other compounds in the liquid phase were

found by ESI-MS except the ones listed in the table.d3- -D-Glucopyra-

nosyl-D-glucitol.

Scheme1.Proposed Reaction Mechanism under Acidic

Conditions

J.AM.CHEM.SOC.9VOL.128,NO.27,20068715

翻译研究中的概念混淆(翻译策略、方法与技巧)).

翻译研究中的概念混淆 ——以“翻译策略”、“翻译方法”和“翻译技巧”为例 熊兵华中师范大学 《中国翻译》2014（3）82-88 摘要：本文对学界在“翻译策略”、“翻译方法”和“翻译技巧”这三个基本概念上所存在的普遍的混淆进行了剖析，提出应对这三个概念进行明确区分。在此基础上论文对这三个概念的定义、特性、相互关系及其各自的分类体系进行了系统阐述。 关键词：翻译策略；翻译方法；翻译技巧；混淆；定义；分类 1．话题缘起 在翻译研究中，有一个问题一直以来都未引起学界足够的重视，并因此在一定程度上妨碍了翻译研究的进一步发展，这个问题即为翻译研究中的概念混淆，其中又尤以“翻译策略”、“翻译方法”和“翻译技巧”这三个概念的混淆为甚。一方面，学界对翻译“策略”、“方法”和“技巧”的讨论虽多如牛毛，但把它们作为一个方法论系统的关键要素进行综合研究，深入考察其各自的内涵、相互关系及分类体系的系统性研究还相当少见。另一方面，学界在对这三个术语的认识和使用上普遍存在着定义不明、分类不当、概念混淆不清的问题。例如，在一些翻译教材中中，“归化”与“异化”一方面被作为“翻译方法”加以讨论(如龚芬，2011：79—81)，另一方面又被视为“翻译策略”进行阐述(同上：93—106)。一些翻译论文把本应属于翻译技巧层面的增补型翻译(类似于增译)、浓缩型翻译(类似于减译)划归为“翻译策略”的类别(如李克兴，2004：66—67)。在一些翻译方向的硕士研究生论文中，把翻译“策略”、“方法”、“技巧”混为一谈的更是比比皆是。甚至翻译专业的老师对此问题也存在一些模糊的、甚至是错误的看法(如把归化等同于意译，把异化等同于直译)。 国外学界对此也存在一些模糊或混淆(或未予严格区分。比如Shuttleworth & Cowie (2004：44，59)一方面把domestication／foreignization称作是“strategy”，另一方面却又把free／literal translation也视为“strategy”(同上：63，96 )。Vinay & Darbelnet (1958／2000：84—93) 把翻译方法(method)分为两类：直接翻译(direct translation)和间接翻译(oblique translation)，前者包括三种处理方式(procedures)，即借译，拟译，直译，后者包括四种处理方式，即词类转换，视点转换，等值翻译，顺应翻译。可在论述中却经常把其划分出来的“方法”(methods)和“处理方式”(procedures)混为一谈。另外，他们把“借译、拟译、直译、等值翻译、顺应翻译”和“词类转换、视角转换”划归为一类(同属procedures)也欠妥当，因为前者应属“翻译方法”的范畴，而后者则应属“翻译技巧”的范畴。实际上，这里Vinay ＆Darbelnet的分类涉及到三个层面：翻译策略、翻译方法和翻译技巧。其划分出来的两大“翻译方法”(直接翻译和间接翻译)其实应为“翻译策略”(所以Munday说，“The two general translation strategies identified by Vinay ＆Darbelnet are direct translation and oblique translation”，见Munday，2008：56)，而在其划分出来的七类“处理方式”中，前三类和最后两类属于“翻译方法”，第四、第五类则属于“翻译技巧”。总之，Vinay ＆Darbelnet在其分类中把翻译“策略、方法、技巧”混淆在一起，这也导致后来很长时间学界在这几个概念上的混淆(Molina ＆Albir，2002：506 0 关于国外译学界在译学术语，特别是在“翻译策略、翻译方法、翻译技巧”三个术语上所存在的概念混淆、使用混乱的问题，Chesterman(2005)和Molina & Albir(2002)曾专门撰文予以讨论。如Chesterman指出，学界用于描述文本操作过程的术语除翻译“策略”外，其他还有“技巧、方法、转换、转化、变易”等等(2005：17)。他认为这种众多术语相互混用

重复法Repetition

翻译技巧1 Repetition 重复法：在译文中适当地重复原文中出现过的词语，以使意思表达得更加清楚；或者进一步加强语气，突出强调某些内容，收到更好的修辞效果。 1.为了明确 1.1重复名词 例1：We have to analyse and solve problems. 我们要分析问题，解决问题。 例2：He became an oil baron—all by himself. 他成为一个石油大王——一个白手起家的石油大王。 1.2重复动词 The blow hurt not only his hands but his shoulder too. 这一下不仅震痛了他的手，也震痛了他的肩膀。 1.3重复代词 重复代词所代替的名词 例1：Peter opened his eyes.They were filled with tears. 彼得睁开了眼睛，眼里充满了泪水。 例2：I hope that the discussion will not be too long,for it will only waste time. 我希望讨论不要太长，太长了只会浪费时间。 重复作代词主语的名词 英语中用物主代词its,his,their等等以代替句中作主语的名词时，翻译中往往可以不用代词而重复其作主语的名词，以达到明确具体的目的。 例1：Happy families are all alike,every unhappy family is unhappy in its own way. 幸福的家庭总是相似的，不幸的家庭各有各的不幸。 例2：Big powers have their strategies while small countries also have their own lines. 强国有大强国的策略，小国也有小国的路线。 重复强势关系代词或关系副词 例1：Whoever violates the law should be punished. 谁犯了法，谁就应该受惩罚。 1.4内容上的重复 为了使译文明确具体，除了以上的重复方法外，还有一种情况：英语原文没有重复，汉译时采用一种在内容上而不是形式上的重复的手段。 例1：He wanted to send them more aid,more weapons and a few more men. 他想给他们增加援助，增添些武器，增派些人员。 2.为了强调 2.1为了强调，英语句子中往往重复关键性的词，以使读者留下深刻的印象，英译汉时往往可以采取同样的重复手段。 例1：He wandered about in the chill rain,thinking and thinking,brooding and brooding. 他在凄雨中荡来荡去，想了又想，盘算了又盘算。 英语对仗句的前后两部分中往往有词的重复，译成汉语时对仗句一般可以保持同样的重复。 对仗重复 An eye for an eye,a tooth for a tooth以眼还眼，以牙还牙 Out of sight,out of mind.眼不见，心不念。 2.2英语原文中有词的重复，译成汉语有时可以用同义词重复。

四种翻译方法,十种翻译技巧

四种翻译方法 1.直译和意译 所谓直译，就是在译文语言条件许可时，在译文中既保持原文的内容，又保持原文的形式——特别指保持原文的比喻、形象和民族、地方色彩等。 每一个民族语言都有它自己的词汇、句法结构和表达方法。当原文的思想内容与译文的表达形式有矛盾不宜采用直译法处理时，就应采用意译法。意译要求译文能正确表达原文的内容，但可以不拘泥与原文的形式。（张培基） 应当指出，在再能确切的表达原作思想内容和不违背译文语言规范的条件下，直译有其可取之处，一方面有助于保存原著的格调，另一方面可以进新鲜的表达方法。 Literal translation refers to an adequate representation of the original. When the original coincides or almost tallies with the Chinese language in the sequence of vocabulary, in grammatical structure and rhetorical device, literal translation must be used. Free translation is also called liberal translation, which does not adhere strictly to the form or word order of the original.（郭著章） 直译法是指在不违背英语文化的前提下，在英译文中完全保留汉语词语的指称意义，求得内容和形式相符的方法。

外文翻译--第三方物流企业的作业成本法

外文翻译--第三方物流企业的作业成本法 本科毕业论文（设计） 外文翻译 外文出处 International Advances in Economic Research, 2001,7 1 : 133-146. 外文作者 Carles Gríful-Miquela 原文： Activity-Based Costing Methodology for Third-Party Logistics Companies This paper will analyze the main costs that third-party logistics companies are facing and develops an activity-based costing methodology useful for this kind of company. It will examine the most important activities carried out by third-party distributors in both warehousing and transporting activities. However, the focus is mainly on the activity of distributing the product to the final receiver when this final receiver is not the customer of the third-party logistics company. Introduction In the last decade, development of third-party logistics companies has been very important. There are several reasons for such development, the most important being the trend to concentrate in the core business

翻译方法和技巧之分译法、合译法

翻译方法和技巧之分译法、合译法翻译方法和技巧之分译法、合译法 Division & Combination * 翻译英语句子时，有时我们可把原文的句子结构整个保存下来或只稍加改变即可，但在不少情况下则必须将原来的句子结构作较大的改变。 * 分译法和合译法是改变原文句子结构的两种重要方法。 * 所谓分译法是指把原文的一个简单句译成两个或两个以上的句子。 * 所谓合译法是指把原文两个或两个以上的简单句或一个复合句在译文中用一个单句来表达。 * 一、分译法 * (一)把原文中的一个单词译成句子，使原文的一个句子分译成两个或两个以上的句子。 * 1.副词 They, *not surprisingly, did not respond at all. 他们根本不回答，这是不足为怪的。 * 2.形容词 * Chairman Mao might have spoken with understandable pride of his policy of “self-reliance”. * 毛主席在谈到他的“自力更生”政策时，也许有些自豪感，这是可以理解的。 * That region was the most identifiable trouble place. 那个地区是个麻烦的地方，这是大家很容易看到的。 * 3.名词

* A movie of me leaving that place would look like a shell leaving a rifle. * 我离开那个地方的速度之快，要是拍成电影的话，会像出膛的子弹一样。 * He shook his head and his eyes were wide, then narrowed in indignation. 他摇了摇头，双目瞪地圆圆的。 * (二)把原文中的一个短语译成句子，使原文的一个句子分译成两个或两个以上的句子。 * 1.分词短语 * She sat with her hands cupping her chin, staring at a corner of the little kitchen. * 她坐在那儿双手托着下巴，眼睛凝视着小厨房的一角。 * Sunrays filtered in wherever they could, driving out darkness and choking . the shadows 阳光射到它所能透过的所有地方，赶走了黑暗，驱散了幽影。 * 2.名词短语 * I wrote four books in the first three years, a record never touched before. * 我头三年写了四本书，打破了以往的记录。 * Energy can neither be created nor destroyed, a universal accepted law. * 能量既不能被消除也不能被创造，这是一条普遍公认的规律。 * 3.前置词短语

成本会计-英文术语

成本会计-英文术语

成本会计中英文术语 非正常毁损Abnormal spoilage 生产成本法Absorption costing 账户分析法Account analysis method 会计回报率Accounting rate of return 权责发生制下会计回报率Accrual accounting rate of return 作业Activity 作业基础的预算管理Activity-based budgeting 作业成本法 Activity-based costing 作业管理 Activity-based management 实际成本Actual cost 实际成本法Actual costing 调整分配率途径Adjusted allocation-rate approach 允许的成本Allowable cost 鉴定成本Appraisal costs 拟构成本Artificial costs 注意力导向Attention directing 自治Autonomy 平均成本Average cost 平均等候时间Average waiting time 反冲成本法Backflush costing

平衡记分卡Balanced scorecard 批次级成本 Batch-level costs 观念系统Belief systems 标杆管理Benchmarking 账面价值Book value 瓶颈Bottleneck 边界系统Boundary systems 盈亏平衡点Breakeven point 预算Budget 预算成本Budgeted cost 预算松弛Budgetary slack 预算间接成本分配率Budgeted indirect-cost rate 捆绑产品Bundled product 业务功能成本Business function costs 副产品Byproducts 资本预算Capital budgeting 储囤成本Carrying costs 现金预算Cash budget 因果图 Cause-and-effect diagram 财务管理认证Certified in financial management 注册管理会计师Certified management accountant 财务总监Chief financial officer 决定系数Coefficient

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经济与管理专业外文翻译--运用作业成本法和经济增加值的具体应用

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作业成本法英文翻译.

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