Formylisophorone | 56621-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Formylisophorone
• 英文别名: 1-Cyclohexene-1-carboxaldehyde, 5,5-dimethyl-3-oxo-；5,5-dimethyl-3-oxocyclohexene-1-carbaldehyde
• CAS: 56621-35-3
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: PIGJMFZYQUTSNI-UHFFFAOYSA-N

物化性质

• 沸点：
  237.5±39.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Formylisophorone 在 selenium(IV) oxide 作用下， 以 溶剂黄146 为溶剂， 以63%的产率得到5,5-dimethyl-3,4-dioxo-1-cyclohexene-1-carbaldehyde
  参考文献：
  名称：

  Martin, Hans-Dieter; Kummer, Matthias; Martin, Georg, Chemische Berichte, 1987, vol. 120, p. 1133 - 1150

  摘要：

  DOI：
• 作为产物：
  描述：

  异佛尔酮 以61%的产率得到Formylisophorone
  参考文献：
  名称：

  Ketoisophorone manufacture

  摘要：

  一种通过在催化剂存在下利用氧气氧化α-异伏伦合成酮异伏伦的制备方法。

  公开号：

  US03960966A1

文献信息

• PROCESS FOR PREPARING 3-AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXYLAMINE
  申请人：Galle Markus

  公开号：US20130253226A1

  公开（公告）日：2013-09-26

  The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or, in abbreviated form, IPDA, by: I. preparation of isophorone by catalyzed aldol condensations with acetone as reactant; II. reaction of isophorone with HCN to form isophoronenitrile (IPN, 3-cyano-3,5,5-trimethylcyclohexanone); III. catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminative hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, hereinafter called isophoronenitrile or, in abbreviated form, IPN, to give the isophoronediamine.

  该发明涉及一种改进的制备3-氨甲基-3,5,5-三甲基环己胺的方法，以下简称异佛酮二胺或简称IPDA，具体步骤包括：I. 用丙酮作为反应物进行催化醛缩制备异佛酮；II. 将异佛酮与HCN反应形成异佛酮腈（IPN，3-氰基-3,5,5-三甲基环己酮）；III. 对3-氰基-3,5,5-三甲基环己酮进行催化氢化和/或催化还原胺化（也称为氨基氢化）处理，以下简称异佛酮腈或简称IPN，制得异佛酮二胺。
• HYDROLYSIS OF THE RESIDUES OBTAINED IN THE PRODUCTION OF ISOPHORONE TO RECOVER ISOPHORONE AND ACETONE
  申请人：NITZ Joerg-Joachim

  公开号：US20150045585A1

  公开（公告）日：2015-02-12

  A process for preparing isophorone (3,5,5-trimethyl-2-cyclohexen-1-one) is provided wherein distillation vapors from the work-up of product fractions are recycled to earlier stages of operation of the process.

  提供了一种制备异佛酮（3,5,5-三甲基-2-环己烯-1-酮）的方法，其中从产品分馏工作过程中产生的蒸馏蒸汽被循环利用到工艺过程的较早阶段。
• Enhanced Catalytic Activity and Selectivity in Oxidation of α-Isophorone to Ketoisophorone with Phosphomolybdic Acid
  作者：Eamonn F. Murphy、Michael Schneider、Tamas Mallat、Alfons Baiker

  DOI：10.1055/s-2001-12358

  日期：——

  Aerobic allylic oxidation of α-isophorone with phosphomolybdic acid as catalyst in combination with DMSO and potassium tert-butoxide provides ketoisophorone in unprecedented high yield. This study suggests that the solvent can play a pivotal role in directing selectivity in allylic oxidations of highly substituted cyclic olefins.

  使用磷钼酸作为催化剂，结合DMSO和叔丁氧钾进行有氧烯丙基氧化α-异佛尔酮，可以以前所未有的高产率获得酮异佛尔酮。这项研究表明，溶剂在高度取代的环烯烃的烯丙基氧化反应中，可以发挥关键作用，指导选择性。
• CATALYTIC OXIDATION OF 3,5,5-TRIMETHYLCYCLOHEXA-3-ENE-1-ONE (ß-ISOPHORONE) WITH HYDROGEN PEROXIDE TO AFFORD 2,6,6-TRIMETHYL-2-CYCLOHEXENE-1,4-DIONE (KETO-ISOPHORONE)
  申请人：Evonik Degussa GmbH

  公开号：US20180155264A1

  公开（公告）日：2018-06-07

  The present invention provides a novel process for producing 2,6,6-trimethyl-2-cyclohexene-1,4-dione (keto-isophorone) by catalytic oxidation of 3,5,5-trimethylcyclohexa-3-ene-1-one (β-isophorone) with hydrogen peroxide as the oxidant. In particular, the novel process includes phase transfer reagent in a biphasic system including an organic phase and an aqueous phase wherein the biphasic system includes 1) a tungsten polyoxyometallate as catalyst and hydrogen peroxide, and/or 2) a mixture of a) a mineral acid, b) hydrogen peroxide, and c) a metal tungstate.

  该发明提供了一种新型的生产2,6,6-三甲基-2-环己烯-1,4-二酮（酮异佛酮）的工艺，通过将3,5,5-三甲基环己烯-3-酮（β-异佛酮）在双氧水作为氧化剂的催化氧化中转化而成。具体而言，该新工艺包括在一个包括有机相和水相的两相体系中加入相转移试剂，所述两相体系包括1）作为催化剂的钨聚氧酸盐和双氧水，和/或2）a）矿酸、b）双氧水和c）金属钨酸盐的混合物。
• An Efficient and Mild Oxidation of α-Isophorone to Ketoisophorone Catalyzed by N-Hydroxyphthalimide and Copper Chloride
  作者：Lihua Chen、Ruiren Tang、Zhongying Li、Shan Liang

  DOI：10.5012/bkcs.2012.33.2.459

  日期：2012.2.20

  N-hydroxyphthalimide (NHPI) and copper chloride ($CuCl_2$) were first utilized for aerobic oxidation of $\alpha}$-isophorone ($\alpha}$-IP) to ketoisophorone (KIP) and the effects of co-catalysts, temperature, reaction time, solvent, amount of $CuCl_2$ and pressure of oxygen were investigated extensively. NHPI/$CuCl_2$ turned out to be highly efficient to this oxidation with up to 91.3% conversion and 81.0% selectivity under mild conditions. And various hydrocarbons including benzylic compounds, cycloalkene and its derivatives were also oxidized smoothly under optimized conditions. Moreover, the possible reaction mechanism was proposed and verified by FT-IR spectra.

  N-羟基邻苯二甲酰亚胺（NHPI）和氯化铜（CuCl₂）首次被用于α-异佛尔酮（α-IP）的有氧氧化，生成酮异佛尔酮（KIP），并广泛研究了助催化剂、温度、反应时间、溶剂、CuCl₂ 的用量以及氧气压力的影响。NHPI/CuCl₂ 证明对该氧化反应具有高效性，在温和条件下达到最高 91.3% 的转化率和 81.0% 的选择性。此外，包括苯甲基化合物、环烯烃及其衍生物在内的各种烃在优化条件下也被顺利氧化。此外，还提出了可能的反应机制，并通过傅里叶变换红外光谱（FT-IR）进行了验证。