1,5-Pentanediol

Base Information

• Chemical Name: 1,5-Pentanediol
• CAS No.: 111-29-5
• Molecular Formula: C5H12O2
• Molecular Weight: 104.149
• Hs Code.: 29053980
• European Community (EC) Number: 203-854-4
• NSC Number: 5927
• UNII: 07UXZ0SCST
• DSSTox Substance ID: DTXSID2041256
• Nikkaji Number: J5.107A
• Wikipedia: 1,5-Pentanediol
• Wikidata: Q161557
• Metabolomics Workbench ID: 134611
• ChEMBL ID: CHEMBL448289
• Mol file: 111-29-5.mol

Synonyms:1,5-pentanediol;1,5-pentanediol, disodium salt;1,5-pentanediol, sodium salt;1,5-pentanediol, titanium (4+) salt (4:1);pentane-1,5-diol

Chemical Property of 1,5-Pentanediol

Chemical Property:

• Appearance/Colour: clear colorless oily liquid
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: -18 °C
• Refractive Index: n20/D 1.450(lit.)
• Boiling Point: 238.999 °C at 760 mmHg
• PKA: 14.83±0.10(Predicted)
• Flash Point: 129.444 °C
• PSA: 40.46000
• Density: 0.982 g/cm³
• LogP: 0.14130
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: Methanol (Slightly)
• Water Solubility.: Miscible
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 104.083729621
• Heavy Atom Count: 7
• Complexity: 25.3

Purity/Quality:

99% ^*data from raw suppliers

1,5-Pentanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C(CCO)CCO
• Recent EU Clinical Trials: A randomized, double-blind, parallell-group, controlled study of topical pentane-1,5-diol hydrogel in patients with impetigo
• Uses: 1,5-Pentanediol has a wide range of applications. Intermediate finds applications in Initial product for chemical syntheses, Inks and coatings, Plasticizers and Solvent, Industrial chemicals. 1,5-Pentanediol is used as a plasticizer in cellulose products and adhesives. It is used as a brake fluid additive. It reacts with 3,4-dihydro-2H-pyran to get 5-tetrahydropyran-2-yloxy-pentan-1-ol. It is also used to prepare polyesters for emulsifying agents and resin intermediates. it is used in ink, toner and colorant products. In addition to this, it is used in brake fluid compositions. 1,5-Pentanediol is used to produce materials made of polyester or polyurethane, for the manufacturing of monomers, for the manufacture of polyester polyols, polycarbonatedioles and acrylic monomers, for the production of delta valerolactone and for molecules that act as reactive diluents, for the production of halogenated substances and for the production of adhesives, putties and sealing compounds, cleaners and auxiliary agents. used in the processes to produce hydrogen, hydrogen peroxide, sodium perborate and peroxyacetic acid and as an intermediate for pharmaceutical products. It is used as an ingredient for the production of polymeric thickeners, plasticizers for polyvinyl chloride, sizing agents, surfactants, for starches and chemically modified starch for application in the paper, textile and food industry, for personal hygiene products like shampoo, creams, and for paints. 1,5-Pentanediol is used largely as a chemical intermediate. Industrial exposure is likely to be from direct contact. 1,5-Pentanediol is used as a reagent in the total synthesis of (+)-Rubriflordilactone A, a nortriterpenoid natural product. 1,5-Pentanediol is also the starting material in the synthesis of Pseudomonic Acid D Sodium (P839520); an antibiotic isolated from Pseudomonas fluorescens.

Technology Process of 1,5-Pentanediol

There total 176 articles about 1,5-Pentanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

furfural (98-01-1) → 2-methylfuran (534-22-5) + 1 ,5-pentanediol (111-29-5)

Guidance literature:

With hydrogen; In 1,4-dioxane; isopropyl alcohol; at 200 ℃; for 24h; under 48754.9 Torr;

DOI:10.1039/d0ra02003f

Reference yield: 41.0%

furfural (98-01-1) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 2-methyltetrahydrofuran (96-47-9) + Tetrahydrofurfuryl alcohol (97-99-4) + 2-methylfuran (534-22-5) + 1 ,5-pentanediol (111-29-5) + 1,2-pentanediol (5343-92-0)

Guidance literature:

With 3% Pd/C; hydrogen; In isopropyl alcohol; at 219.84 ℃; for 40h; under 25858.1 Torr; Inert atmosphere;

Reference yield: 32.0%

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) → Tetrahydrofurfuryl alcohol (97-99-4) + 2-methylfuran (534-22-5) + 1 ,5-pentanediol (111-29-5) + 1,2-pentanediol (5343-92-0) + pentan-1-ol (71-41-0)

Guidance literature:

With Cu⁽⁵⁰⁾,Zn⁽⁵⁰⁾ (X%); hydrogen; at 170 ℃; for 2h; under 112511 - 187519 Torr; Reagent/catalyst; Autoclave;

upstream raw materials:

Tetrahydrofurfuryl alcohol

furfural

(2-furyl)methyl alcohol

2-methoxy-3,4-dihydro-2H-pyran

Downstream raw materials:

2-phenoxy-[1,3,2]dioxaphosphocane

1,5-diacetoxypentane

1,5-diphenylcarbamoyloxypentane

pentane-1,5-diyl bis-(p-nitrobenzoate)

Refernces

• 1、 Pinazzi et al.. "". . p. 9,11. Retrieved 1976.
• 2、 Bianchi, Mario,Menchi, Gloria,Francalanci, Franco,Piacenti, Franco,Matteoli, Ugo,et al.. "HOMOGENEOUS CATALYTIC HYDROGENATION OF FREE CARBOXYLIC ACIDS IN THE PRESENCE OF CLUSTER RUTHENIUM CARBONYL HYDRIDES". . p. 109 - 120. Retrieved 1980.
• 3、 Karakhanov, E. A.,Neimerovets, E. B.,Pshezhetskii, V. S.,Dedov, A. G.. "HYDROGENATION OF FURFURAL ON POLYMER-CONTAINING CATALYSTS". . p. 243 - 246. Retrieved 1986.
• 4、 Koso, Shuichi,Ueda, Naoyuki,Shinmi, Yasunori,Okumura, Kazu,Kizuka, Tokushi,Tomishige, Keiichi. "Promoting effect of Mo on the hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Rh/SiO2". . p. 89 - 92. Retrieved 2009.
• 5、 An, Zhe,He, Jing,Jiang, Yitao,Ma, Xiaodan,Shu, Xin,Song, Hongyan,Xiang, Xu,Zhang, Jian,Zhang, Zhijun,Zhao, Wenfang,Zheng, Lirong,Zhu, Yanru. "Selective Activation of C-OH, C-O-C, or Ca? C in Furfuryl Alcohol by Engineered Pt Sites Supported on Layered Double Oxides". . p. 8032 - 8041. Retrieved 2020.
• 6、 Zaidi, Javid H.,Fauq, Abdul H.,Ahmed, Naseera. "Comparative studies of the deprotection of various acid sensitive protecting groups with pyridinium p-toluenesulphonate". . p. 4137 - 4138. Retrieved 1998.
• 7、 Asano, Takehiro,Nakagawa, Yoshinao,Tamura, Masazumi,Tomishige, Keiichi. "Hydrogenolysis of tetrahydrofuran-2-carboxylic acid over tungsten-modified rhodium catalyst". . . Retrieved 2020.
• 8、 Kliger, G. A.,Lesik, O. A.,Ryzhikov, V. P.,Gleb, L. S.,Loktev, S. M.. "REACTION OF TETRAHYDROFURFURYL ALCOHOL WITH DIMETHYLAMINE AND/OR HYDROGEN". . p. 2644 - 2645. Retrieved 1987.
• 9、 Brown,H.C. et al.. "-". . p. 3561 - 3567. Retrieved 1972.
• 10、 Koso, Shuichi,Nakagawa, Yoshinao,Tomishige, Keiichi. "Mechanism of the hydrogenolysis of ethers over silica-supported rhodium catalyst modified with rhenium oxide". . p. 221 - 229. Retrieved 2011.