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Chemical compound From Wikipedia, the free encyclopedia
5-Amino-1-pentanol is an amino alcohol with a primary amino group and a primary hydroxy group at the ends of a linear C5-alkanes. As a derivative of the platform chemical furfural (that is easily accessible from pentoses), 5-amino-1-pentanol may become increasingly important in the future as a building block for biodegradable polyesteramides and as a starting material for valerolactam — the monomer for polyamides.
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.017.926 |
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Properties | |
C5H13NO | |
Molar mass | 103.16 g·mol−1 |
Density | 0.9488 at 17 °C |
Melting point | 38.5 °C (101.3 °F; 311.6 K) |
Boiling point | 221.5 °C (430.7 °F; 494.6 K) |
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GHS labelling:[1] | |
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H302, H314 | |
P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The complete hydrogenation of furfural (furan-2-aldehyde) yields tetrahydrofurfuryl alcohol (2-hydroxymethyltetrahydrofuran), which undergoes ring expansion upon dehydration to give dihydropyran. Dihydropyran reacts with ammonia in a reductive amination under ring opening to produce 5-amino-1-pentanol.[2]
Product yields of up to 85% can be achieved with a continuous process using a nickel-hydrotalcite catalyst.
Similarly, the hemiacetal 2-hydroxytetrahydropyran[3] that is formed from dihydropyran with hydrochloric acid can be converted to 5-amino-1-pentanol by reductive amidation with ammonia and hydrogen upon water elimination.[4]
5-Amino-1-pentanol forms white crystalline clumps at solidification temperatures around 35 °C, which dissolve in water, ethanol, and acetone.[5] The aqueous solution (500 g-l−1) reacts strongly alkaline (pH 13.2 at 20 °C).[6]
Amino alcohols such as 5-amino-1-pentanol have been studied for their suitability of absorption of carbon dioxide.[7][8]
5-Amino-1-pentanol dehydrates when heated over ytterbium(III) oxide (Yb2O3) to give 4-penten-1-amine (I). Also formed piperidine (II), 2,3,4,5-tetrahydropyridine (III), and 1-pentylamine (IV).[9]
Being bifunctional, 5-amino-1-pentanol reacts in a polycondensation reaction with esters of dicarboxylic acids (or their cyclic acid anhydrides, such as succinic anhydride) to give polyesteramides. These polymers have been investigated as biodegradable plastics, e.g. absorbable sutures.[10][11] During the reaction, the succinic anhydride reacts initially with the nucleophilic amino group to form an ω-hydroxycarboxylic acid, which is subsequently polycondensed with carbodiimides, such as the hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimides (EDC-HCl).
In a dehydrogenation, catalyzed by rhodium and ruthenium complexes, valerolactam, the δ-lactam of 5-aminopentanoic acid, is formed from 5-amino-1-pentanol in high (94%) yield.[12][13]
Valerolactam could be of relevance for polyamide 5. Polyamide 5 has garnered little attention so far but is of interest due to its ferroelectricity.[14]
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