mucic acid dibutyl ester | 70910-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mucic acid dibutyl ester
• 英文别名: dibutyl (2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioate
• CAS: 70910-63-3
• 化学式: C₁₄H₂₆O₈
• 分子量: 322.356
• InChiKey: LWCSLVQDDOZYNX-IWDIQUIJSA-N

物化性质

• 沸点：
  504.4±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  mucic acid dibutyl ester 在 Si-propylsulfonic acid 作用下， 以 正丁醇 为溶剂， 220.0 ℃ 、500.01 kPa 条件下， 反应 4.0h， 生成 2,5-呋喃二甲酸
  参考文献：
  名称：

  平台化学品的独特途径：醛酸作为合成呋喃二甲酸酯的稳定中间体

  摘要：

  2,5-呋喃二甲酸（FDCA）作为一种新兴的生物基建筑材料受到了广泛关注，尤其是在可再生聚酯中，具有许多应用。到达FDCA的常用途径是使用不稳定的5-羟甲基糠醛（HMF）作为中间体。在这里，我们介绍了使用C6醛酸作为稳定中间体生产FDCA及其酯的另一种方法。醛糖酸或糖二酸可通过将C6糖或果胶酸从果胶中氧化而获得。随后在丁醇中通过固体酸催化剂使醛酸脱水，生成呋喃羧酸盐。使用二氧化硅负载的酸催化剂，呋喃羧酸盐的收率超过90％，对FDCA及其酯的选择性达到80％。

  DOI：

  10.1039/d0gc02293d
• 作为产物：
  描述：

  meso-galactaric acid 、 正丁醇 在 对甲苯磺酸 作用下， 生成 mucic acid dibutyl ester
  参考文献：
  名称：

  Lactose utilisation to furan carboxylates: a unique source for platform molecules

  摘要：

  通过粘液酸作为中间体，以极佳的效率将乳制品行业的乳糖副流转化为高价值的呋喃羧酸盐，这是生产全氟辛烷磺酸的潜在来源（通过 https://Biorender.com 创建）。

  DOI：

  10.1039/d3gc04317g

文献信息

• Expanding the Scope of Biomass-Derived Chemicals through Tandem Reactions Based on Oxorhenium-Catalyzed Deoxydehydration
  作者：Mika Shiramizu、F. Dean Toste

  DOI：10.1002/anie.201307564

  日期：2013.12.2

  New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual‐purpose catalysts to transform biomass‐derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]‐OH shift/DODH of 2‐ene‐1,4‐diols and 2,4‐diene‐1,6‐diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production

  DODH的新模式：氧化hen化合物充当脱氧脱水（DODH）/酸两用催化剂，将生物质衍生的二醇底物转化为多种商品化学前体。通过2-烯-1,4-二醇和2,4-二烯-1,6-二醇的串联[1,3] -OH移位/ DODH以及DODH /酯化序列突出了这种方法的优势糖酸到不饱和酯的合成，用于生产聚合物和增塑剂。
• Effects of a New Selective Estrogen Receptor Modulator (MDL 103,323) on Cancellous and Cortical Bone in Ovariectomized Ewes: A Biochemical, Histomorphometric, and Densitometric Study
  作者：Pascale Chavassieux、Patrick Garnero、Francois Duboeuf、Philippe Vergnaud、Francoise Brunner-Ferber、Pierre D. Delmas、Pierre J. Meunier

  DOI：10.1359/jbmr.2001.16.1.89

  日期：——

  The aims of this study performed in ewes were: (1) to confirm in this animal model the effects on bone of ovariectomy (OVX) alone or associated with Lentaron (L), a potent peripheral aromatase inhibitor, used to amplify the effects of OVX and (2) to evaluate the effects of a new selective estrogen receptor modulator (SERM; MDL 103,323) on bone remodeling. Thirty‐nine old ewes were divided into five groups: sham (n = 7); OVX (n = 8); OVX + L (n = 8); OVX + L + MDL; 0.1 mg/kg per day (n = 8); and OVX + L + MDL 1 mg/kg per day (n = 8). The animals were treated for 6 months. Biochemical markers of bone turnover (urinary excretion of type 1 collagen C‐telopeptide [CTX], serum osteocalcin [OC], and bone alkaline phosphatase [BAP]) were measured each month. Bone biopsy specimens were taken at the beginning and after death at the end of the experiment. Bone mineral density (BMD) was measured by dual‐energy X‐ray absorptiometry (DXA) on the lumbar spine and femur. OVX induced a significant increase in biochemical markers. This effect was the highest after 3 months for CTX (+156% vs. sham) and after 4 months for OC and BAP (+74% and +53% vs. sham, respectively). L tended to amplify the effect of OVX on OC and BAP. OVX induced significant increases in the porosity, eroded, and osteoid surfaces in cortical bone but no effect was observed in cancellous bone. MDL treatment reduced the bone turnover as assessed by bone markers, which returned to sham levels as well as histomorphometry both in cortical and in cancellous bone. Cancellous osteoid thickness decreased by 27% (p < 0.05), mineralizing perimeter by 81% (p < 0.05), and activation frequency by 84% (p < 0.02) versus OVX + L. Femoral and spinal BMD were increased by MDL and tended to return to the sham values. The effects of OVX on bone turnover were different on cortical and cancellous bone. These effects on cortical bone were reflected by changes in biochemical markers. MDL markedly reduces bone turnover and increases BMD suggesting that this new agent may prevent postmenopausal bone loss.

  本研究在母羊中进行，旨在：(1) 在这一动物模型中确认单独或联合使用强效外周芳香化酶抑制剂Lentaron（L）的卵巢切除术（OVX）对骨骼的影响，以增强OVX的效果；(2) 评估一种新的选择性雌激素受体调节剂（SERM；MDL 103,323）对骨重建的影响。研究共纳入39只老母羊，分为五组：假手术组（n = 7）；OVX组（n = 8）；OVX + L组（n = 8）；OVX + L + MDL 0.1 mg/kg每日至（n = 8）；OVX + L + MDL 1 mg/kg每日至（n = 8）。动物治疗持续了6个月。每月测量骨代谢的生化标记物（尿中1型胶原C末端肽[CTX]、血清骨钙素[OC]和骨碱性磷酸酶[BAP]）。在实验开始时及结束时对死亡后的骨活检标本进行取样。通过双能X射线吸收法（DXA）测量腰椎和股骨的骨矿密度（BMD）。OVX显著提高了生化标记物的水平。这一效应在3个月后CTX达到最高值（+156%对比假手术组），在4个月后OC和BAP分别增加了74%和53%。L倾向于增强OVX对OC和BAP的影响。OVX使皮质骨的孔隙度、侵蚀面和骨样面显著增加，但海绵骨未观察到影响。MDL治疗降低了骨代谢，生化标记物恢复至假手术组水平，组织形态学分析显示皮质和海绵骨均如此。海绵骨骨样厚度减少了27%（p < 0.05），矿化边缘减少了81%（p < 0.05），激活频率减少了84%（p < 0.02），相较于OVX + L组。MDL使股骨和脊柱的BMD增加，并趋向恢复至假手术组水平。OVX对骨代谢的影响在皮质骨和海绵骨上有所不同。这些对皮质骨的影响体现在生化标记物的变化上。MDL显著降低了骨代谢并增加了BMD，提示该新剂可能预防绝经后骨质流失。
• Ionic liquid-mediated deoxydehydration reactions: Green synthetic process for bio-based adipic acid
  作者：Nara Shin、Sohyun Kwon、Sojeong Moon、Chae Hwan Hong、Young Gyu Kim

  DOI：10.1016/j.tet.2017.06.053

  日期：2017.8

  A novel recyclable Re-catalyzed deoxydehydration (DODH) reaction was developed with an ionic liquid (IL) as a reaction medium for an efficient synthesis of adipic acid (1), one of the commercially important dicarboxylic acids, from biomass galactaric acid. The carefully designed solubility of ILs allowed a homogeneous DODH reaction to produce muconate 3 in excellent yields, a key intermediate for 1

  以离子液体（IL）为反应介质，开发了一种新型可循环再催化脱氧（DODH）反应，用于从生物质半乳糖有效合成己二酸（1），这是一种重要的商业二元羧酸。精心设计的IL溶解度允许均相的DODH反应以优异的产率生成粘液3，这是1的关键中间体。IL的使用还使得能够通过简单的倾析将DODH产物3从反应混合物中有效地分离出来。所回收的包含昂贵的Re催化剂的IL层可重复使用多达四次，在收率没有大幅降低的情况下得到3。目标化合物1用3的催化加氢，然后进行酸水解，也能以优异的收率生产三氯甲烷。因此，生物基己二酸的整个过程将变得更具成本效益，生态友好且在工业上可行，可以应用于各种生物质转化。
• [EN] SYNTHESIS AND PURIFICATION OF MUCONIC ACID ESTER FROM ALDARIC ACID ESTERS<br/>[FR] SYNTHÈSE ET PURIFICATION D'ESTER D'ACIDE MUCONIQUE À PARTIR D'ESTERS D'ACIDE ALDARIQUE
  申请人：TEKNOLOGIAN TUTKIMUSKESKUS VTT OY

  公开号：WO2019155128A1

  公开（公告）日：2019-08-15

  According to an example aspect of the present invention, there is provided a method for producing muconic acid ester from aldaric acid ester, and for separating and purifying the produced muconic acid ester by high vacuum distillation in a total heating environment.

  根据本发明的一个实施例，提供了一种从醛糖酸酯生产须二酸酯的方法，并通过在总加热环境下进行高真空蒸馏来分离和纯化所生产的须二酸酯。
• 사용된 촉매의 회수 및 재사용 공정을 포함하는 뮤코네이트 제조 방법
  申请人：HYUNDAI MOTOR COMPANY 현대자동차주식회사(119980045675) Corp. No ▼ 110111-0085450BRN ▼101-81-09147

  公开号：KR20180062041A

  公开（公告）日：2018-06-08

  본 발명은 사용된 촉매의 회수 및 재사용 공정을 포함하는 뮤식산으로부터 뮤코네이트를 제조하는 방법에 관한 것으로, 보다 상세하게는 반응 용매에 뮤식산 다이에스터와, 촉매 용액을 넣고 혼합하여 반응 용액을 준비하는 단계, 상기 준비된 반응 용액을 일정 온도에서 일정시간 동안 디옥시디하이드레이션(deoxydehydration) 반응시키는 단계, 상기 반응한 반응 용액을 농축시킨 후 유기용매를 넣고 혼합하여 촉매를 포함하는 하층부의 이온성액체 층과 뮤코네이트를 포함하는 상부층의 유기용매 층으로 분리하고, 분리된 두 개의 층을 각각 회수하는 단계, 상기 회수된 상층부의 유기용매 층을 농축하고 정제하여 뮤코네이트를 수득하는 단계, 및 상기 촉매를 녹인 상태로 회수된 하부층의 이온성액체 층은 농축하여 촉매 용액으로 재사용하는 단계를 포함한다. 이러한 본 발명의 제조방법에 따르면 해양자원과 같은 바이오 매스로부터 나일론 66의 원료물질이 되는 아디픽산을 제조하여 환경 친화적일 뿐만 아니라, 이온성액체를 사용하여 고가의 촉매를 효율적으로 분리한 후 회수된 촉매를 수회 재사용 함으로써 전체 공정의 효율성 및 경제성을 높이는 효과를 갖는 장점이 있다.

  本发明涉及一种从椰子油酸制造己内酰胺的方法，其中包括回收和再利用催化剂的过程。更具体地，该方法包括将椰子油酸二酯和催化剂溶液加入反应溶剂中混合制备反应溶液，将制备的反应溶液在一定温度下进行一定时间的脱水脱氧反应，浓缩反应后的溶液并加入有机溶剂混合，将含催化剂的离子液层和含己内酰胺的有机溶剂层分离，分别回收两个分离的层，浓缩和精制回收的有机溶剂层以获得己内酰胺，并将回收的催化剂溶液浓缩以便再次使用。根据本发明的制造方法，可以从生物质如海洋资源中制造己内酰胺的原料，这是一种环保的方法。此外，使用离子液体有效地分离和回收高成本的催化剂，可以多次重复使用催化剂，提高整个过程的效率和经济性。