3-(2-methyl-5-oxotetrahydrofuran-2-yl) 4-oxopentanoic acid | 856219-95-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-(2-methyl-5-oxotetrahydrofuran-2-yl) 4-oxopentanoic acid
• 英文别名: 3-(2-Methyl-5-oxooxolan-2-yl)-4-oxopentanoic acid
• CAS: 856219-95-9
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: UYNYFEJBGNEWRD-UHFFFAOYSA-N

物化性质

• 沸点：
  431.0±15.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-6-oxononanedioic acid 、 3-(2-methyl-5-oxotetrahydrofuran-2-yl) 4-oxopentanoic acid 、 3-acetyl-4-methylheptanedioic acid 、 2-methyl-5,γ-dioxotetrahydrofuran-2-valeric acid 、 乙醇 在 10 wt% nickel/0.1 wt% platinum on silica and zeolite β 氢气 作用下， 200.0~240.0 ℃ 、8.0 MPa 条件下， 反应 75.0h， 生成 diethyl 2-methylnonanedioate 、 3-ethyl-4-methyl-heptanedioic acid diethyl ester
  参考文献：
  名称：

  WO2006/67171

  摘要：

  公开号：
• 作为产物：
  描述：

  乙酰丙酸 在 SiO₂-SO₃H 作用下， 反应 6.0h， 生成 3-(2-methyl-5-oxotetrahydrofuran-2-yl) 4-oxopentanoic acid 、 3-acetyl-2-methyltetrahydro-5-oxo-2-furanpropanoic acid 、 2-methyl-5,γ-dioxotetrahydrofuran-2-valeric acid
  参考文献：
  名称：

  固体酸催化乙酰丙酸羟醛醛二聚反应制备C10可再生燃料和化学原料

  摘要：

  使用一系列固体酸催化剂研究了乙酰丙酸的酸催化缩合反应：Amberlyst-15，SiO 2 -SO 3 H，Dowex50WX8，Carbon-SO 3 H，TiO 2 -SO 3 H，Al 2 O 3 -SO 3 H，H 3 PW 12 O 40和Nb 2 O 5 .H 2O在110–130°C的纯净条件下。鉴定出主要的二聚产物为四氢-2-甲基-5，γ-二氧代-2-呋喃戊酸。另外，鉴定出四个次要产物为3-（2-甲基-5-氧代-四氢呋喃-2-基）-4-氧戊酸和3-乙酰基-2-甲基-四氢-5-氧代-2的非对映异构对。 -呋喃丙酸的光谱学和计算方法。提出了一种机制来解释五种二聚产物的形成，其中主要产物是通过乙酰丙酸的C5烯醇形式的醛醇缩合形成的，而四个次要产物是由乙酰丙酸的C3烯醇形式的醛醇缩合产生的。使用SiO 2 -SO 3可获得最高的总收率56％作为固体酸催化剂的H和质量平衡的提醒是未反应的乙酰丙酸。SiO

  DOI：

  10.1016/j.catcom.2019.02.022

文献信息

• [EN] PROCESS FOR HYDROGENATION<br/>[FR] PROCÉDÉ POUR L'HYDROGÉNATION
  申请人：SHELL INT RESEARCH

  公开号：WO2011015643A1

  公开（公告）日：2011-02-10

  A process for the hydrogenation of a reactant selected from: (a) a 5- or 6-membered lactone that is substituted at the ring-closing carbon atom and has a proton at a carbon atom adjacent to the ring-closing carbon atom; (b) an ester of a carboxylic acid having a gamma- carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group; and (c) a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group, which process involves contacting the reactant with a catalyst in the presence of hydrogen, at a temperature from 100 to 3500C and a pressure from 1 to 150 bar (absolute), provided the pressure is low enough to avoid condensation of the heaviest feed component at the temperature chosen, and wherein the catalyst is a weakly acidic heterogeneous catalyst comprising a hydrogenating metal.

  一种用于氢化反应物的方法，所选反应物包括：(a) 在环闭合碳原子处取代的5-或6-成员内酯，且在环闭合碳原子相邻的碳原子上有质子；(b) 具有γ-羰基和在羰基碳原子相邻的碳原子上有质子的羧酸酯；以及(c) 具有γ-羰基和在羰基碳原子相邻的碳原子上有质子的羧酸，该方法涉及将反应物与催化剂接触在氢气存在下，温度在100至350°C，压力在1至150 bar（绝对值）范围内进行，前提是压力足够低以避免在所选温度下最重的进料组分的凝结，并且催化剂是弱酸性的异质催化剂，包括氢化金属。
• PROCESS FOR HYDROGENATION
  申请人：Lange Jean-Paul

  公开号：US20110112326A1

  公开（公告）日：2011-05-12

  A process for the hydrogenation of a reactant selected from: (a) a 5- or 6-membered lactone that is substituted at the ring-closing carbon atom and has a proton at a carbon atom adjacent to the ring-closing carbon atom; (b) an ester of a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group; and (c) a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group, which process involves contacting the reactant with a catalyst in the presence of hydrogen, at a temperature from 100 to 350° C. and a pressure from 1 to 150 bar (absolute), provided the pressure is low enough to avoid condensation of the heaviest feed component at the temperature chosen, and wherein the catalyst is a weakly acidic heterogeneous catalyst comprising a hydrogenating metal.

  一种用于氢化反应物的方法，所述反应物选自：(a)在环闭合碳原子处取代并在环闭合碳原子相邻碳原子处有质子的5-或6-成员内酯；(b)具有γ-羰基和在γ-羰基相邻碳原子处有质子的羧酸酯；以及(c)具有γ-羰基和在γ-羰基相邻碳原子处有质子的羧酸，该方法涉及将反应物与催化剂在氢气存在下接触，在温度为100至350°C和压力为1至150巴（绝对）的条件下，只要压力足够低以避免在所选温度下使最重的进料组分凝结，并且所述催化剂是弱酸性的异质催化剂，包括氢化金属。
• [EN] PROCESS FOR PREPARING AN ESTER<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'UN ESTER
  申请人：SHELL INT RESEARCH

  公开号：WO2011015385A1

  公开（公告）日：2011-02-10

  A process for preparing an ester of formula (I): R3CH2- (CR1R2)n-CH2-O-CO-(CR1R2)n-CH2R3 (I) wherein n is 1-3 and R1 and R2 are each, independently, a hydrogen atom or a carbon-linked organic group and R3 is a carbon-linked organic group, by hydrogenation of a reactant selected from: (a) a lactone of formula (II) wherein n is 1-3 and R1 and R2 are each, independently, a hydrogen atom or a carbon-linked organic group and R3 is a carbon-linked organic group; (b) an ester of a carboxylic acid of formula (III) R4-O-CO- (CR1R2)n-CO-R3 (III) wherein n is 1-3 and R1 and R2 are each, independently, a hydrogen atom or a carbon-linked organic group and R3 and R4 are a carbon-linked organic group; and c) a carboxylic acid of formula (IV) H-O-CO- (CR1R2)n-CO-R3 (IV) wherein n is 1-3 and R1 and R2 are each, independently, a hydrogen atom or a carbon-linked organic group and R3 is a carbon-linked organic group; which process involves contacting the reactant with a heterogeneous catalyst comprising a hydrogenating metal in the presence of hydrogen, wherein the catalyst is a zeolite-free heterogeneous catalyst comprising a hydrogenating metal supported on a metal oxide or a mixed oxide.

  制备式(I)酯的过程：R3CH2- (CR1R2)n-CH2-O-CO-(CR1R2)n-CH2R3 (I)，其中n为1-3，R1和R2分别独立地为氢原子或碳链有机基团，R3为碳链有机基团，通过选择的反应物的加氢制备：(a)式(II)内酯，其中n为1-3，R1和R2分别独立地为氢原子或碳链有机基团，R3为碳链有机基团；(b)式(III)羧酸酯，其中n为1-3，R1和R2分别独立地为氢原子或碳链有机基团，R3和R4为碳链有机基团；和(c)式(IV)羧酸，其中n为1-3，R1和R2分别独立地为氢原子或碳链有机基团，R3为碳链有机基团；该过程涉及将反应物与含有氢化金属的非均相催化剂接触，在氢气存在下，其中催化剂是一种不含沸石的非均相催化剂，包括负载在金属氧化物或混合氧化物上的氢化金属。
• HYDROGENATION PROCESS FOR THE CONVERSION OF A CARBOXYLIC ACID OR AN ESTER HAVING A CARBONYL GROUP
  申请人：Haan Johan Rene

  公开号：US20070208183A1

  公开（公告）日：2007-09-06

  A hydrogenation process for the conversion of a reactant selected from the group consisting of a carboxylic acid having a carbonyl group and an ester of a carboxylic acid having a carbonyl group to form a carboxylic acid or an ester with a hydroxyl group or a lactone, wherein the reactant is contacted with a heterogeneous catalyst comprising a hydrogenating compound, in the presence of formic acid, at a temperature in the range of from 150 to 400° C. and a pressure in the range of from 1.0 to 150 bar (absolute).

  一种氢化工艺，用于将来自以下组的反应物转化为具有羟基或内酯的羧酸或羧酸酯：具有羰基的羧酸或羧酸酯的酯，其中将反应物与含有氢化合物的非均相催化剂接触，在甲酸存在下，在温度为150至400℃和压力为1.0至150巴（绝对值）的范围内进行。
• Renewable hydrocarbons, method for producing the same and use thereof
  申请人：NESTE OYJ

  公开号：US10968397B2

  公开（公告）日：2021-04-06

  A method for conversion of levulinic acid and to a hydrocarbon composition obtainable by the method. The method includes a step of providing a feedstock, a conversion step of subjecting the feedstock to a C—C coupling reaction and a hydrotreatment, and a hydrodeoxygenation step. The content of levulinic acid dimer derivatives having 4 oxygen atoms subjected to the hydrodeoxygenation step is 20 wt.-% or more.

  一种转化乙酰丙酸和可通过该方法获得的碳氢化合物组合物的方法。该方法包括提供原料步骤、将原料进行 C-C 偶联反应和加氢处理的转化步骤以及加氢脱氧步骤。经过加氢脱氧步骤的具有 4 个氧原子的乙酰丙酸二聚体衍生物的含量为 20 wt.-% 或更多。