4792-15-8

Usage

Uses

Used in Chemical Synthesis:
PENTAETHYLENE GLYCOL is used as an intermediate for the synthesis of cyclic and noncyclic polyethers, complexing agents, and immobilized phase-transfer catalysts. Its versatile chemical properties make it a valuable component in creating a variety of compounds.
Used in Biodegradation:
PENTAETHYLENE GLYCOL is part of a group of compounds called polyethylene glycols (PEGs), which are major byproducts of non-ionic surfactants biodegradation. This highlights its role in the environmental breakdown of certain chemicals.
Used in Pharmaceutical Industry:
PENTAETHYLENE GLYCOL is used as a synthetic intermediate for synthesizing macrocyclic oligoesters through lipase-catalysis. This application is particularly relevant in the development of new pharmaceutical compounds and drug delivery systems.
Used in Solubility Enhancement:
PENTAETHYLENE GLYCOL is used to increase the water solubility of compounds in aqueous media. The presence of the PEG chain improves the solubility properties, making it a useful tool in the formulation of various products, including pharmaceuticals and chemicals.

Synthesis Reference(s)

Synthetic Communications, 16, p. 19, 1986 DOI: 10.1080/00397918608057683

InChI:InChI=1/C10H22O6/c11-1-3-13-5-7-15-9-10-16-8-6-14-4-2-12/h11-12H,1-10H2

Upstream product

• 75-21-8 oxirane 
• 111-46-6 diethylene glycol 
• 107-21-1 ethylene glycol 
• 106-93-4 ethylene dibromide 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 112-26-5 1,2-bis(2-chloroethoxy)ethane 
• 68375-98-4 2-methyl-17-crown-6 
• 7553-56-2 iodine 
• 2615-15-8 pentaethylene glycol 
• 141282-24-8 2-(2-{2-[2-(trityloxyethoxy)ethoxy]ethoxy}ethoxy)ethanol 
• 27712-99-8 1,3,6,9,2λ⁴-Tetraoxathia-2-cycloundecanon 
• 55489-58-2 triethylene glycol monobenzyl ether 
• 60389-48-2 C₂₄H₃₄O₆ 
• 81194-62-9 2,2-Diphenyl-1,3,6,9,12,15-hexaoxa-cycloheptadecane 

Downstream Products

• 57602-02-5 1,14-dibromo-3,6,9,12-tetraoxatetradecane 
• 34188-11-9 2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethanol 
• 69928-16-1 27-phenyl-7,8,10,11,13,14,16,17,19,20,22,27-dodecahydro-5H-6,9,12,15,18,21-hexaoxa-27-phospha-dibenzo[a,d]cyclotricosene 27-oxide 
• 68436-52-2 3,6,9,12,15,18-hexaoxa-24-azabicyclo<18.3.1>tetracosa-1(24),20,22-triene-2,19-dione 
• 25990-96-9 octaethylene glycol monomethyl ether 
• 5197-65-9 1,14-dichloro-3,6,9,12-tetraoxatetradecane 
• 70445-64-6 2,5,8,11,14,17-hexaoxa-1(2,6)-pyridina-cycloheptadecaphane-1³-carbonitrile 
• 60742-60-1 n-Decyl-18-crown-6 
• 84812-04-4 <(Allyloxy)-methyl>-18-crown-6 
• 75507-21-0 1-phenyl-2,5,8,11,14,17-hexaoxacyclooctadecane 
• 51105-00-1 1-[2-(2-{2-[2-(2-Butoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-butane 
• 130727-47-8 undec-1-en-11-ylpenta(ethylene glycol) 
• 76461-90-0 18-ethyl-1,4,7,10,13,16-hexaoxacyclononadecane-17,19-dione 
• 28821-35-4 pentadecaethylene glycol 

Relevant academic research and scientific papers

Photocatalytic Degradation of Hexaethylene Glycol

Abstract: Polyethylene glycol (PEG) photodegradation was studied in water under UV irradiation in the presence of catalytic amount of TiO2 using hexaethylene glycol as a model compound. Full conversion was achieved in 7 h with an average quantum yield around 1%. Formic acid was found to be the main intermediate and was slower to oxidize into CO2 (traces remains after 24 h). The other intermediates [lower PEG, oxidized PEG (formates, aldehydes and acids, acetic acid)] of the photodegradation have also been identified and quantified. A mechanism based on previous literature but also taking into account these new observations is proposed. Graphical Abstract: [Figure not available: see fulltext.].

Highly efficient synthesis of monodisperse poly(ethylene glycols) and derivatives through macrocyclization of oligo(ethylene glycols)

A macrocyclic sulfate (MCS)-based approach to monodisperse poly(ethylene glycols) (M-PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62-membered macrocycle) as versatile precursors for a range of monofunctionalized M-PEGs. Through iterative nucleophilic ring-opening reactions of MCS without performing group protection and activation, a series of M-PEGs, including the unprecedented 64-mer (2850Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M-PEGs. Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64-mer.

Novel C1-symmetric chiral crown ethers bearing rosin acids groups: Synthesis and enantiomeric recognition for ammonium salts

Four types of novel C1-symmetric chiral crown ethers including 28-crown-8, 20-crown-6, 17-crown-5 and 14-crown-3 (9a-m) were synthesized and their enantiodiscriminating abilities with protonated primary amines (10-14) were examined by 1H NMR spectroscopy. 20-crown-6 crown ethers exhibited good chiral recognition properties toward these guests and showed different complementarity to some chiral guests, indicating that 20-crown-6 crown ethers could be used as a chiral NMR solvating agent to determine the enantiopurity of these guests. In addition, the binding model and binding site between the hosts and guests were also studied by the computational modeling and experimental calculation.

Valency platform molecules comprising carbamate linkages

This invention pertains generally to valency molecules, such as valency platform molecules which act as scaffolds to which one or more molecules may be covalently tethered to form a conjugate. More particularly, the present invention pertains to valency platform molecules which comprise a carbamate linkage (i.e., —O—C(=O)—N). In one aspect, the present invention pertains to valency platforms comprising carbamate linkages, which molecules have the structure of any one of Formulae I, II, or III, shown in FIG. 1. In one aspect, the present invention pertains to valency platforms comprising carbamate linkages, which molecules have the structure of any one of Formulae IV, V, or VI, shown in FIG. 8. The present invention also pertains to methods of preparing such valency platform molecules, conjugates comprising such valency platform molecules, and methods of preparing such conjugates.

Intramolecular End-to-End Reactions of Photoactive Terminal Groups Linked by Poly(oxyethylene) Chains

The triplet-sensitized photochemical reaction using a series of poly(oxyethylene) chains with a pair of photoactive terminal groups, dibenzazepine (DBA) chromophores (DBA-COCH2CH2(OCH2CH2)nOCH2CH2CO-DBA, n=0-10) was examined.The photoirradiation of bichromophoric compounds caused either intra- or intermolecular reactions.These reactions were kinetically analyzed by two different methods: the measurement of deactivation processes of the reaction intermediates (excited triplet state of DBA) by nanosecond laser photolysis and the quantitative analysis of the reaction products by GPC.The intramolecular deactivation rate constant, kintra, showed a remarkable chain-length dependence; the maximum kintra value appeared at n=5 and it was found to be 5.9X104 s-1.On the other hand, the intramolecular cyclization rate also depends on the chain length; the maximum quantum yield, φintrad, was given at n=7 (φintrad=0.51).The chain length for the maximum cyclization yield shifted slightly to the longer region than that for the maximum kintra value due to the restriction of the terminal structure (anti-configuration).The results obtained for this reaction system are compared with those obtained for the previously reported polymethylene system and the effect of chain flexibility on the intramolecular ring-closure reaction is discussed.

A NOVEL, UNEQUIVOCAL SYNTHESIS OF POLYETHYLENE GLYCOLS

Unequivocal synthesis of polyethyleneglycols is presented.The key step for this synthesis is the selective monobenzylation of oligoethyleneglycols by the phase transfer catalysis technique.

Molecular Design of Crown Ethers. 1. Effects of Methylene Chain Length: 15- to 17-Crown-5 and 18- to 22-Crown-6

The ring-enlarged crown ethers, 16- and 17-crown-5 and 19- to 22-crown-6, were synthesized and their cation-binding abilities were evaluated by solvent extraction of aqueous alkali metal picrates.The cation-binding abilities of less symmetrical crown ethers, 3a-e and 4a,b, were generally lower than those of the common symmetrical crown ethers 15-crown-5 (5a) and 18-crown-6 (5b), for which the less symmetrical arrangement of the donor oxygen atoms must be responsible.Compared with 18-crown-6 (5b), the ring-extended crown ethers, 3d, 3e, and 4b, showed a significant shift in cation selectivity, probably due to the enlarged cavity size.The thermodynamic parameters for the extraction of sodium and potassium picrates with 3a, 3c, and 5a,b were calculated from the change of the extraction equilibrium constants (Kex) between 10-25 deg C.The stability of the cation-crown ether complexes was shown to be governed in general by the enthalpy change.However, a significant contribution of the entropy factor was found in unfavorable size combinations of K+ with 3a and Na+ with 3c.

The Influence of Cation Binding on the Kinetics of the Hydrolysis of Crown Ether Acetals

The rate of hydrogen ion-catalysed hydrolysis of crown ether acetals in 60:40 (v/v) dioxan-water is found to be strongly decreased by the addition of alkali and alkaline earth metal chlorides having cations of appropriate size to be complexed by the substrate ring.The compounds studied are the monoacetals CH3CH(OCH2CH2)xO with x=1-8.The dependence of the initial rate of formation of acetaldehyde on metal-ion concentration is expressed in terms of (i) the equilibrium constant for complex formation, (ii) the influence of the bound cation on the rate constant, and (iii) an electrolyte effect.A curve-fitting procedure is used to derive the parameters governing the first two of these effects.The equilibrium constants are large and cannot be evaluated with any precision, but a fair estimate of the influence of the guest cation on the rate can be obtained.This effect is explicable by the electrostatic repulsion between the cationic charges of the metal ion and the proton added to the acetal in the first step of the hydrolysis.The size of the effect requires the values of the effective relative permittivity of the space between the charges to be close to that of the bulk solvent.