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]
synthesis of 5-amino-1-pentanol from 2-hydroxytetrahydropyran
Propertiesedit
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]
Applicationsedit
Amino alcohols such as 5-amino-1-pentanol have been studied for their suitability of absorption of carbon dioxide from combustion gases,[7] or by binding it in concrete.[8]
When heating 5-amino-1-pentanol to 400 °C over ytterbium(III) oxide Yb2O3, 4-penten-1-amine (I) is formed with high selectivity by water splitting, in addition to small quantities of piperidine (II), 2,3,4,5-tetrahydropyridine (III) and 1-pentylamine (IV).[9] Also the formation of 5-hydroxypentanal and 1-methylpiperidine has been reported.
polyesteramides with 5-amino-1-pentanol and succinic anhydride
In a dehydration coupling catalyzed by rhodium(I) complexes, valerolactam, the δ-lactam of 5-aminopentanoic acid, is formed from 5-amino-1-pentanol in high (94%) yield.[12]
valerolactam formation from 5-amino-1-pentanol
The oxidative ring closure of 5-amino-1-pentanol to lactam 2-piperidone also succeeds with the hydrogen transfer catalyst triruthenium dodecacarbonyl Ru3(CO)12, in conjunction with a phosphane complex.[13]
The high availability of valerolactam as a direct downstream product of 5-amino-1-pentanol, which comes readily and efficiently from renewable raw materials, could be of relevance for polyamide 5. Polyamide 5 has garnered little attention so far, but is of interest due to its ferroelectricity.[14]
^X. Li; J. Tian; H. Liu; X. Hu; J. Zhang; C. Xia; J. Chen; H. Liu; Z. Huang (2020), "Efficient Synthesis of 5-Amino-1-pentanol from Biomass-Derived Dihydropyran over Hydrotalcite-Based Ni–Mg3AlOx Catalysts", ACS Sustain. Chem. Eng., 8 (23): 6352–6362, doi:10.1021/acssuschemeng.0c00394, S2CID 216508238
^T. Oishi; M. Kanemoto; R. Swasono; N. Matsumori; M. Murata (2008), "Combinatorial Synthesis of the 1,5-Polyol System Based on Cross Metathesis: Structure Revision of Amphidinol 3", Org. Lett., 10 (22): 5203–5206, doi:10.1021/ol802168r, PMID 18959425
^J. Zhang; et al. (2021), "Reductive amination of bio-based 2-hydroxytetrahydropyran to 5-amino-1-pentanol over nano-Ni-Al2O3 catalysts", New J. Chem., vol. 45, no. 9, pp. 4236–4245, doi:10.1039/D0NJ04962J, S2CID 234007765
^William M. Haynes (2017), CRC Handbook of Chemistry and Physics (97th ed.), Boca Raton, FL: CRC Press, pp. 3–22, ISBN978-1-4987-5429-3
^P. Singh; G.F. Versteeg (2008), "Structure and activity relationships for CO2 regeneration from aqueous amine-based absorbents" (PDF), Process Saf. Environ. Prot., 86 (5): 347–359, doi:10.1016/j.psep.2008.03.005
^S. Oa; B.-J. Kim; J.-W. Park (2020), "Effects of carbonation on carbon dioxide capture and the mechanical properties of concrete with amine sorbents", Adv. Cement Res., 32 (11): 502–509, doi:10.1680/jadcr.18.00198, S2CID 155957571
^K. Ohta; Y. Yamada; S. Sato (2016), "Dehydration of 5-amino-1-pentanol over rare earth oxides", Appl. Catal A: General, 517: 73–80, doi:10.1016/j.apcata.2016.03.001
^US 4209607, S.W. Shalaby & D.D. Jamiolkowski, "Polyesteramides derived from bis-oxamidodiols and dicarboxylic acids", published 1980-6-24, assigned to Ethicon, Inc.
^S.K. Murase; J. Puiggali (2014), "Poly(ester amides)s: Recent Developments on Synthesis and Applications", in S.G. Kumbar; C.T. Laurencin; M. Deng (eds.), Natural and Synthetic Biomedical Polymers, Amsterdam: Elsevier, pp. 154–166, ISBN978-0-12-396983-5
^M. Trincado; K. Kühlein; H. Grützmacher (2011), "Metal-ligand cooperation in the catalytic dehydrogenative coupling (DHC) of polyalcohols to carboxylic acid derivatives", Chem. Eur. J., 17 (42): 11905–11913, doi:10.1002/chem.201101084, PMID 21901769
^D. Pingen; D. Vogt (2014), "Amino-alcohol cyclization: selektivem synthesis of lactams and cyclic amines from amino-alcohols", Catal. Sci. Technol., 4: 47–52, doi:10.1039/C3CY00513E, S2CID 52265163
^T. von Tiedemann; S. Anwas; U. Kemmer-Jonas; K. Asadi; H. Frey (2020), "Synthesis and solution processing of nylon-5 ferroelectric thin films: The renaissance of odd-nylons?", Macromol. Chem. Phys., 221 (5): 1900468, doi:10.1002/macp.201900468, hdl:21.11116/0000-0005-A118-A, S2CID 213517034
December 15, 2023
amino, pentanol, amino, alcohol, with, primary, amino, group, primary, hydroxy, group, ends, linear, alkanes, derivative, platform, chemical, furfural, that, easily, accessible, from, pentoses, amino, pentanol, become, increasingly, important, future, building. 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 5 Amino 1 pentanol IdentifiersCAS Number 2508 29 4 Y3D model JSmol Interactive imageChEMBL ChEMBL333552ChemSpider 68156ECHA InfoCard 100 017 926EC Number 219 718 2PubChem CID 75634CompTox Dashboard EPA DTXSID10179771InChI InChI 1S C5H13NO c6 4 2 1 3 5 7 h7H 1 6H2Key LQGKDMHENBFVRC UHFFFAOYSA NSMILES C CCN CCOPropertiesChemical formula C5H13NOMolar mass 103 16 g mol 1Density 0 9488 at 17 CMelting point 38 5 C 101 3 F 311 6 K Boiling point 221 5 C 430 7 F 494 6 K HazardsGHS labelling 1 PictogramsSignal word DangerHazard statements H302 H314Precautionary statements 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 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Occurrence and preparation 2 Properties 3 Applications 4 ReferencesOccurrence and preparation editThe 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 nbsp synthesis of 5 amino 1 pentanol from dihydropyranProduct 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 nbsp synthesis of 5 amino 1 pentanol from 2 hydroxytetrahydropyranProperties edit5 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 Applications editAmino alcohols such as 5 amino 1 pentanol have been studied for their suitability of absorption of carbon dioxide from combustion gases 7 or by binding it in concrete 8 When heating 5 amino 1 pentanol to 400 C over ytterbium III oxide Yb2O3 4 penten 1 amine I is formed with high selectivity by water splitting in addition to small quantities of piperidine II 2 3 4 5 tetrahydropyridine III and 1 pentylamine IV 9 Also the formation of 5 hydroxypentanal and 1 methylpiperidine has been reported nbsp dehydration of 5 amino 1 pentanolThe bifunctional 5 amino 1 pentanol can react in a polycondensation reaction with esters of dicarboxylic acids or their cyclic acid anhydrides such as succinic anhydride to obtain 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 w hydroxycarboxylic acid which is subsequently polycondensed with carbodiimides such as the hydrochloride of 1 ethyl 3 3 dimethylaminopropyl carbodiimides EDC HCl nbsp polyesteramides with 5 amino 1 pentanol and succinic anhydrideIn a dehydration coupling catalyzed by rhodium I complexes valerolactam the d lactam of 5 aminopentanoic acid is formed from 5 amino 1 pentanol in high 94 yield 12 nbsp valerolactam formation from 5 amino 1 pentanolThe oxidative ring closure of 5 amino 1 pentanol to lactam 2 piperidone also succeeds with the hydrogen transfer catalyst triruthenium dodecacarbonyl Ru3 CO 12 in conjunction with a phosphane complex 13 The high availability of valerolactam as a direct downstream product of 5 amino 1 pentanol which comes readily and efficiently from renewable raw materials could be of relevance for polyamide 5 Polyamide 5 has garnered little attention so far but is of interest due to its ferroelectricity 14 References edit 5 Aminopentan 1 ol pubchem ncbi nlm nih gov X Li J Tian H Liu X Hu J Zhang C Xia J Chen H Liu Z Huang 2020 Efficient Synthesis of 5 Amino 1 pentanol from Biomass Derived Dihydropyran over Hydrotalcite Based Ni Mg3AlOx Catalysts ACS Sustain Chem Eng 8 23 6352 6362 doi 10 1021 acssuschemeng 0c00394 S2CID 216508238 T Oishi M Kanemoto R Swasono N Matsumori M Murata 2008 Combinatorial Synthesis of the 1 5 Polyol System Based on Cross Metathesis Structure Revision of Amphidinol 3 Org Lett 10 22 5203 5206 doi 10 1021 ol802168r PMID 18959425 J Zhang et al 2021 Reductive amination of bio based 2 hydroxytetrahydropyran to 5 amino 1 pentanol over nano Ni Al2O3 catalysts New J Chem vol 45 no 9 pp 4236 4245 doi 10 1039 D0NJ04962J S2CID 234007765 William M Haynes 2017 CRC Handbook of Chemistry and Physics 97th ed Boca Raton FL CRC Press pp 3 22 ISBN 978 1 4987 5429 3 Sigma Aldrich Co product no id P Singh G F Versteeg 2008 Structure and activity relationships for CO2 regeneration from aqueous amine based absorbents PDF Process Saf Environ Prot 86 5 347 359 doi 10 1016 j psep 2008 03 005 S Oa B J Kim J W Park 2020 Effects of carbonation on carbon dioxide capture and the mechanical properties of concrete with amine sorbents Adv Cement Res 32 11 502 509 doi 10 1680 jadcr 18 00198 S2CID 155957571 K Ohta Y Yamada S Sato 2016 Dehydration of 5 amino 1 pentanol over rare earth oxides Appl Catal A General 517 73 80 doi 10 1016 j apcata 2016 03 001 US 4209607 S W Shalaby amp D D Jamiolkowski Polyesteramides derived from bis oxamidodiols and dicarboxylic acids published 1980 6 24 assigned to Ethicon Inc S K Murase J Puiggali 2014 Poly ester amides s Recent Developments on Synthesis and Applications in S G Kumbar C T Laurencin M Deng eds Natural and Synthetic Biomedical Polymers Amsterdam Elsevier pp 154 166 ISBN 978 0 12 396983 5 M Trincado K Kuhlein H Grutzmacher 2011 Metal ligand cooperation in the catalytic dehydrogenative coupling DHC of polyalcohols to carboxylic acid derivatives Chem Eur J 17 42 11905 11913 doi 10 1002 chem 201101084 PMID 21901769 D Pingen D Vogt 2014 Amino alcohol cyclization selektivem synthesis of lactams and cyclic amines from amino alcohols Catal Sci Technol 4 47 52 doi 10 1039 C3CY00513E S2CID 52265163 T von Tiedemann S Anwas U Kemmer Jonas K Asadi H Frey 2020 Synthesis and solution processing of nylon 5 ferroelectric thin films The renaissance of odd nylons Macromol Chem Phys 221 5 1900468 doi 10 1002 macp 201900468 hdl 21 11116 0000 0005 A118 A S2CID 213517034 Retrieved from https en wikipedia org w index php title 5 Amino 1 pentanol amp oldid 1185810631, wikipedia, wiki, book, books, library,
