626-95-9

Basic information

• Product Name: 1,4-Pentanediol
• Synonyms: 1,4-Dihydroxy-1-methylbutane;1,4-Dihydroxypentane; 2,5-Pentanediol; 4-Hydroxy-1-pentanol
• CAS NO: 626-95-9
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.1476
• EINECS: 210-973-5
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 626-95-9.mol
• Article Data: 152

Chemical Properties

• Melting Point: 50.86°C (estimate)
• Boiling Point: 72-73 °C0.03 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.986 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00029mmHg at 25°C
• Refractive Index: 1.443
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol (Sparingly)
• PKA: 15.09±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 1,4-Pentanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Pentanediol(626-95-9)
• EPA Substance Registry System: 1,4-Pentanediol(626-95-9)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 626-95-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 626-95-9 differently. You can refer to the following data:
1. 1,4-Pentanediol is a useful synthetic intermediate. It was used in the preparation of poly(ortho ester). 1,4-Pentanediol on dehydration in water at 573K yields five-membered ether, 2-methyltetrahydrofuran.
2. 1,4-Pentanediol was used in the preparation of poly(ortho ester).

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 1961, 1947 DOI: 10.1021/ja01200a036

General Description

1,4-Pentanediol on dehydration in water at 573K yields five-membered ether, 2-methyltetrahydrofuran.

InChI:InChI=1/C5H12O2/c1-5(7)3-2-4-6/h5-7H,2-4H2,1H3

Upstream product

• 534-22-5 2-methylfuran 
• 123-76-2 levulinic acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 19953-93-6 (2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-ol 
• 75-07-0 acetaldehyde 
• 764-37-4 (E)-3-penten-1-ol 
• 624-24-8 methyl valerate 
• 73476-17-2 4-(4-Cyanbenzyloxy)-1-pentanol 
• 109-52-4 valeric acid 
• 591-12-8 5-methyl-2-furanone 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 60-29-7 diethyl ether 
• 7732-18-5 water 

Downstream Products

• 5412-69-1 5-diethylaminopentan-2-ol 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 106018-81-9 5-[(phenylmethyl)thio]pentan-2-ol 
• 59-49-4 2-hydroxybenzoxazole 
• 18381-22-1 5-acetoxy-2-pentanol 
• 431-03-8 dimethylglyoxal 
• 32864-71-4 1,4-diacetoxypentane 
• 26903-61-7 1,4-Pentadiolbisbenzoat 
• 128733-37-9 Benzoic acid 4-(dimethyl-phenyl-silanyloxy)-pentyl ester 
• 128733-36-8 1,4-Pentanediol 4-O-benzoyl ester 1-dimethylphenylsilyl ether 
• 5185-97-7 4-oxopentyl acetate 
• 96-47-9 2-methyltetrahydrofuran 
• 6032-29-7 (+/-)-2-pentanol 
• 626-87-9 1,4-dibromopentane 

Relevant articles and documents

Partially biobased polymers: The synthesis of polysilylethers via dehydrocoupling catalyzed by an anionic iridium complex

Partially biobased polysilylethers (PSEs) are synthesized via dehydrocoupling polymerization catalyzed by an anionic iridium complex. Different types (AB type or AA and BB type) of monomers are suitable. Levulinic acid (LA) and succinic acid (SA) have been ranked within the top 10 chemicals derived from biomass. BB type monomers (diols) derived from LA and SA have been applied to the synthesis of PSEs. The polymerization reactions employ an air-stable anionic iridium complex bearing a functional bipyridonate ligand as catalyst. Moderate to high yields of polymers with number-average molecular weights (Mn) up to 4.38 × 104 were obtained. A possible catalytic cycle via an Ir-H species is presented. Based on the results of kinetic experiments, apparent activation energy of polymerization in the temperature range of 0–10 °C is about 38.6 kJ/mol. The PSEs synthesized from AA and BB type monomers possess good thermal stability (T5 = 418 °C to 437 °C) and low glass-transition temperature (Tg = ?49.6 °C).

Transformation of γ-valerolactone into 1,4-pentanediol and 2-methyltetrahydrofuran over Zn-promoted Cu/Al2O3catalysts

The transformation of γ-valerolactone (GVL) into 1,4-pentanediol (1,4-PDO) and 2-methyltetra-hydrofuran (2-MTHF) in the presence of H2, one of the useful biomass conversion and utilization processes, was investigated with monometallic Cu/Al2O3 and bimetallic ZnCu/Al2O3 catalysts. A 10 wt% Cu-loaded monometallic catalyst produced 1,4-PDO and 2-MTHF in comparable quantities at a medium conversion (～50%). When Zn was added in a range of Zn/Cu molar ratios of up to 2, in contrast, the catalysts yielded 1,4-PDO in a high selectivity of about 97% at low and high conversion levels. In addition, the 1,4-PDO selectivity over the ZnCu/Al2O3 catalysts remained almost unchanged during recycled runs. That is, the addition of Zn to Cu/Al2O3 switched the product selectivity and improved the catalyst stability and reusability. Furthermore, the physicochemical properties of the catalysts were characterized by several methods including XRD, TEM, TPR, XPS, FTIR of adsorbed pyridine, and so on. On the basis of those results, the relationships between the catalytic performance (activity, selectivity, and reusability) and the catalyst structural features were discussed.

Manganese-Catalyzed Hydrogenation of Sclareolide to Ambradiol

The hydrogenation of (+)-Sclareolide to (?)-ambradiol catalyzed by a manganese pincer complex is reported. The hydrogenation reaction is performed with an air- and moisture-stable manganese catalyst and proceeds under relatively mild reaction conditions at low manganese and base loadings. A range of other esters could be successfully hydrogenated leading to the corresponding alcohols in good to quantitative yields using this easy-to-make catalyst. A scale-up experiment was performed leading to 99.3 % of the isolated yield of (?)-Ambradiol.

Ru Nanoparticles on a Sulfonated Carbon Layer Coated SBA-15 for Catalytic Hydrogenation of Furfural into 1, 4-pentanediol

Furfural (FFR) is one of the most important biomass-derived chemicals. Its large-scale availability calls for the exploration of new transformation methods for further valorization. Herein, we demonstrate that Ru nanoparticles (Ru NPs)-supported on a sulfonated carbon layer coated SBA-15 can be employed as an efficient bi-functional catalyst for one step conversion of FFR into 1,4-pentanediol (1,4-PeDO). The optimum bi-functional catalyst can afford the full the conversion of FFR and 86% selectivity to 1,4-PeDO. The catalysts have been characterized thoroughly by using a complementary combination of powder X-ray diffraction, N2 adsorption–desorption, scanning/transmission electron microscopy, Fourier transform infrared spectroscopy, elemental analysis, and X-ray photoelectron spectroscopy. The characterization revealed that acidic groups (–SO3H) have been introduced on the surface of the carbon layer coated SBA-15 support after sulfonation with 98% H2SO4 and the surface acidity can be tuned facilely by the sulfonating time. Meantime, Ru(0) sites was highly dispersed via an impregnation and sequential reduction and directly adjacent to the surface –SO3H group. There existed an electronic interaction between Ru(0) sites and sulfonic groups, in which the electronic transfer from sulfonic sites to Ru(0) sites occurred. Br?nsted acid sites (–SO3H) have a significant influence on the FFR conversion and the selectivity to 1,4-PeDO. The ordered mesoporous structure, the appropriate density of acid sites and the electron-rich Ru(0) sites accounted for the the excellent performance of the catalyst for an efficient production of 1,4-PeDO from FFR. Graphic Abstract: [Figure not available: see fulltext.].

Synthesis method of pentanediol, and synthesis method for preparing biomass-based pentadiene through conversion of levulinic acid and derivatives of levulinic acid

The invention provides a synthesis method of pentanediol, and the method comprises the following steps: carrying out conversion reaction on a mixed solution obtained by mixing levulinic acid and/or levulinic acid derivatives, a catalyst and an organic solvent in a hydrogen-containing atmosphere to obtain the pentanediol. According to the method, a large amount of cheap and easily available bio-based chemical levulinic acid or derivatives thereof can be utilized, pentanediol is obtained through catalytic conversion, and m-pentadiene is further obtained. The raw materials are derived from renewable resources, the m-pentadiene is prepared through hydrogenation and dehydration, and particularly, a green and sustainable process route for synthesizing the m-pentadiene is finally obtained through a dehydration reaction route and construction of a dehydration catalyst. The invention provides a method for green and sustainable synthesis of linear pentadiene based on bio-based chemical conversion, and the method has the advantages of simple operation, short flow, no need of harsh experimental conditions, easy preparation of raw materials and catalysts, and large-scale synthesis prospect.