​每周分子Molecule of the Week

Molecule of the Week: 2,5-Furandicarboxylicacid

每周分子：2,5-呋喃二甲酸

1876年，德国化学家Wilhelm Rudolf Fittig从非环状的、糖衍生的半乳糖二酸（粘酸）合成了2, 5-呋喃二甲酸（后来被称为脱水粘酸）。2, 5-呋喃二甲酸，或FDCA一直到过去的几年里才引起人们较多的关注，因为它被发现是生产聚酯的潜在的可再生单体。

化学/生化公司杜邦、Corbin和Synvina（一家BASF和Avantium的合资公司）已经从5-（羟甲基）糠醛和5-（甲氧甲基）糠醛开发了FDCA的有效合成方法，这两种糠醛都可以从天然果糖中获得。这种生物基FDCA和生物基1, 2-乙二醇一起可用于制造可再生的聚乙烯呋喃酯（PEF），PEF与广泛使用的聚乙烯对苯二甲酸酯（PET）具有相似的特性。

PEF实际上提供了比PET更好的气体屏障，使它成为制造碳酸饮料塑料瓶的优秀候选材料。但PEF与PET的不同意味着汽水瓶和其他塑料包装材料必须重新设计。除了放大FDCA的生产，用PEF大规模地替换PET还有一段很长的路要走。

作为一个开始，Synvina正在比利时的安特卫普建造一个50000吨/年的FDCA工厂；杜邦公司在美国伊利诺伊州的迪凯特一个60吨/年的试点工厂的即将建造完成，用于生产一种也可以用来制备PEF的FDCA衍生物——2,5-呋喃二甲酸单甲酯。

【关于每周分子 】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社（CAS）提供的SciFinder中的CAS REGISTRY获取每周分子的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至[e-mail]推荐您感兴趣的分子。

In 1876, German chemist Wilhelm Rudolf Fittig synthesized 2,5-furandicarboxylic acid (then called dehydromucic acid) from acyclic, sugar-derived galactaric (mucic) acid. 2,5-Furandicarboxylic acid, or FDCA, did not draw much interest until the past several years, when it was recognized as a potential sustainable monomer for polyester manufacturing.

Chemical/biochemical companies DuPont, Corbion, and Synvina (a BASF–Avantium joint venture) have developed efficient syntheses of FDCA from 5-(hydroxymethyl) furfural and 5-(methoxymethyl) furfural, both of which can be made from natural fructose. Along with biobased ethylene glycol, this biobased FDCA can be used to make sustainable poly (ethylene furanoate) (PEF), a polyester that has properties similar to those of the widely used poly (ethylene terephthalate) (PET).

PEF actually provides better gas barrier than PET, making it an excellent candidate for making plastic bottles for carbonated beverages. But PEF’s differences from PET mean that soda bottles and other plastic packaging materials would have to be redesigned. That, in addition to scaling up the manufacture of FDCA, dictates that large-scale replacement of PET with PEF is a long way off.

As a start, Synvina is building a 50,000 t/year FDCA plant in Antwerp, Belgium; and DuPont is nearing the completion of a 60 t/year pilot plant at Decatur, IL, to make 2,5-furandicarboxylic monomethyl ester, an FDCA derivative that can also be used to make PEF.

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at [e-mail].

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