69847-38-7

Basic information

• Product Name: butyl 4-hydroxyvalerate
• Synonyms: butyl 4-hydroxyvalerate;4-Hydroxypentanoic acid butyl ester
• CAS NO: 69847-38-7
• Molecular Formula: C₉H₁₈O₃
• Molecular Weight: 174.23742
• EINECS: 274-150-2
• Mol File: 69847-38-7.mol

Chemical Properties

• Boiling Point: 254.2°C at 760 mmHg
• Flash Point: 98.8°C
• Appearance: /
• Density: 0.976g/cm³
• Vapor Pressure: 0.00269mmHg at 25°C
• Refractive Index: 1.439
• PKA: 14.92±0.20(Predicted)
• CAS DataBase Reference: butyl 4-hydroxyvalerate(CAS DataBase Reference)
• NIST Chemistry Reference: butyl 4-hydroxyvalerate(69847-38-7)
• EPA Substance Registry System: butyl 4-hydroxyvalerate(69847-38-7)

Safety Data

• Hazardous Substances Data: 69847-38-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H18O3/c1-3-4-7-12-9(11)6-5-8(2)10/h8,10H,3-7H2,1-2H3

Upstream product

• 2052-15-5 butyl levulinate 
• 64-17-5 ethanol 
• 141-32-2 acrylic acid n-butyl ester 

Relevant articles and documents

Ammonia borane enabled upgrading of biomass derivatives at room temperature

Simplifying biomass conversion to valuable products with high efficiency is pivotal for the sustainable development of society. Herein, an efficient catalyst-free system using ammonia borane (AB) as the hydrogen donor is described, which enables controllable reaction selectivity towards four value-added products in excellent yield (82-100%) under very mild conditions. In particular, the system is uniquely efficient to produce γ-valerolactone (GVL) at room temperature. Combined in situ NMR and computational studies elucidate the hydrogen transfer mechanism of AB in methanol, the novel pathway of GVL formation from levulinate in water, and a competitive mechanism between reduction and reductive amination in the same system. Moreover, carbohydrates are converted directly into GVL in good yield, using a one-pot, two-step strategy. Products of a rather broad scope are prepared within a short reaction time of 30 min by using this catalyst-free strategy in methanol at room temperature. This journal is

Screening of Solvents, Hydrogen Source, and Investigation of Reaction Mechanism for the Hydrocyclisation of Levulinic Acid to Γ-Valerolactone Using Ni/SiO2–Al2O3 Catalyst

Abstract: Commercial 65% Ni/SiO2–Al2O3 (Ni/SA) catalyst was investigated for hydrocyclisation of levulinic acid (LA) to γ-valerolactone (Gvl) in presence of different hydrogen sources such as molecular hydrogen, isopropyl alcohol (IPA), and formic acid. At optimized reaction condition (200?°C, 10?bar H2 for 30?min), the Ni/SA catalyst showed 100% yield of Gvl using molecular H2 in tetrahydrofuran (THF) medium. The catalyst also exhibited 99% yield of Gvl in IPA through catalytic transfer hydrocyclisation of LA at 200?°C in 15?min. Further, the hydrocyclisation was successfully demonstrated in continuous mode using molecular hydrogen for 20?h time-on-stream which showed 98–99% conversion of LA with 100% selectivity of Gvl at optimized reaction condition in THF medium. Graphical Abstract: [Figure not available: see fulltext.]

H-Bonding-promoted radical addition of simple alcohols to unactivated alkenes

H-Bonding-induced radical addition of simple alcohols to unactivated olefins was achieved. It effectively solved the long-standing problems of reactivity and selectivity in this type of reaction. The hydroxyalkylation occurred via site-specific cleavage of the α-hydroxyl-C-H bond in alcohols. This method allows a highly atom-economical, operationally simple and environmentally benign access to diverse primary, secondary and tertiary alcohols, diols, and even polyfluorinated alcohols. These useful chemicals are traditionally synthesized by using commercially unavailable organometallics via complex operations. In contrast, they can be facilely obtained through this protocol utilizing widely available starting materials.

Conversion of biomass-derived levulinate and formate esters into γ-valerolactone over supported gold catalysts

The utilization of biomass has recently attracted tremendous attention as a potential alternative to petroleum for the production of liquid fuels and chemicals. We report an efficient alcohol-mediated reactive extraction strategy by which a hydrophobic mixture of butyl levulinate and formate esters, derived from cellulosic biomass, can be converted to valuable γ-valerolactone (GVL) by a simple supported gold catalyst system without need of an external hydrogen source. The essential role of the supported gold is to facilitate the rapid and selective decomposition of butyl formate to produce a hydrogen stream, which enables the highly effective reduction of butyl levulinate into GVL. This protocol simplifies the recovery and recycling of sulfuric acid, which is used for cellulose deconstruction.