16096-31-4

Basic information

• Product Name: 1,6-Hexanediol diglycidyl ether
• Synonyms: 1,6-HEXANEDIOL DIGLYCIDYL ETHER;(generic)phosphoramide;1,6-bis(2,3-Epoxypropoxy)hexane;2,2’-[1,6-hexanediylbis(oxymethylene)]bis-oxiran;Oxirane, 2,2-1,6-hexanediylbis(oxymethylene)bis-;1,6-Bis(2,3-epoxypropoxy)hexan;2,2'-(1,6-Hexanediylbis(oxymethylene))oxirane;1,6-Bis(glycidyloxy)hexane
• CAS NO: 16096-31-4
• Molecular Formula: C₁₂H₂₂O₄
• Molecular Weight: 230.3
• EINECS: 240-260-4
• Mol File: 16096-31-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 328.7 °C at 760 mmHg
• Flash Point: 120 °C
• Appearance: /
• Density: 1.076 g/cm³
• Vapor Pressure: 9.75E-09mmHg at 25°C
• CAS DataBase Reference: 1,6-Hexanediol diglycidyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Hexanediol diglycidyl ether(16096-31-4)
• EPA Substance Registry System: 1,6-Hexanediol diglycidyl ether(16096-31-4)

Safety Data

• Hazardous Substances Data: 16096-31-4(Hazardous Substances Data)

Usage

Uses

Its primary use is as a reactive diluent in epoxy resin systems to reduce viscosity and to allow higher filler loading.

Production Methods

The compound results from condensation of hexanediol with epichlorohydrin followed by dehydrochlorination with caustic.

Contact allergens

This chemical is a reactive diluent in epoxy resins.

InChI:InChI=1/C6H10O3.C6H14O2/c1(5-3-8-5)7-2-6-4-9-6;7-5-3-1-2-4-6-8/h5-6H,1-4H2;7-8H,1-6H2

Synthetic route

1,6-hexanediol (629-11-8) + epichlorohydrin (106-89-8) → 1,6 hexanediol diglycidyl ether (16096-31-4)

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In water at 40℃; for 2h;	68.2%
With tetrabutylammomium bromide; sodium hydroxide In water at 40℃; for 2h;
Etherification;
tin(IV) chloride Etherification;

1,6-bis(allyloxy)hexane (81866-56-0) → 1,6 hexanediol diglycidyl ether (16096-31-4) + C12H22O3 (1246463-46-6)

Conditions	Yield
With dihydrogen peroxide; benzonitrile; triethylamine In water at 60℃; for 25h; Conversion of starting material;	A 29% B 44%

1,6-hexanediol (629-11-8) + epichlorohydrin (106-89-8) → 1,6 hexanediol diglycidyl ether (16096-31-4) + 6-hydroxy hexyl glycidyl ether

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 5h; Heating;	A 14 g B 50 g

1,6-hexanediol (629-11-8) + 1,2-Epoxy-3-bromopropane (3132-64-7) → 1,6 hexanediol diglycidyl ether (16096-31-4) + 6-hydroxy hexyl glycidyl ether

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 7h; Heating;	A 35 g B 35 g

1-chloro-3-[6-(3-chloro-2-hydroxy-propoxy)-hexyloxy]-propan-2-ol (20387-39-7) → 1,6 hexanediol diglycidyl ether (16096-31-4)

Conditions	Yield
With sodium hydride In hexane; toluene at 20℃; for 0.0833333h; Cyclization;	228 mg

1,6-hexanediol (629-11-8) → 1,6 hexanediol diglycidyl ether (16096-31-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: SnCl4 / toluene; heptane / 3 h / 90 °C 2: 228 mg / NaH / toluene; hexane / 0.08 h / 20 °C View Scheme

1,6 hexanediol diglycidyl ether (16096-31-4) + 2-oxo-1,3-dioxolane-4-carboxylic acid (871835-30-2) → C20H30O14

Conditions	Yield
With chromium(III) acetylacetonate; triethylamine In tetrahydrofuran at 80℃; for 16h;	100%

1,6 hexanediol diglycidyl ether (16096-31-4) + (2-dimethylamino-1-(4-morpholinophenyl)-2-(4-carboxyphenylmethyl)butan-1-one) → C60H82N4O12

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile for 10h; Reflux;	88%

1,6 hexanediol diglycidyl ether (16096-31-4) → 3-{[6-(2,3-dihydroxypropoxy)hexyl]oxy}-1,2-propanediol

Conditions	Yield
With water; trifluoroacetic acid Hydrolysis; ring cleavage;	63%

1,6 hexanediol diglycidyl ether (16096-31-4) + n-Octylamine (111-86-4) → di[(2-hydroxy-3-octylamino)propyloxy]hexamethylene (189192-11-8)

Conditions	Yield
In ethanol for 4h;	105 g

1,6 hexanediol diglycidyl ether (16096-31-4) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → acetic acid 2-acetoxy-1-[6-(2,3-diacetoxy-propoxy)-hexyloxymethyl]-ethyl ester

Conditions	Yield
Acetoxylation; acetylation; ring cleavage;

1,6 hexanediol diglycidyl ether (16096-31-4) + reduced [3H]glutathione (148102-19-6) → oxidized glutathione + (S)-2-Amino-4-[2-[3-(6-{3-[2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-2-hydroxy-propoxy}-hexyloxy)-2-hydroxy-propylsulfanyl]-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

Conditions	Yield
In phosphate buffer; dimethyl sulfoxide at 20℃; for 18h; pH=7.4; Enzyme kinetics; Kinetics; Further Variations:; Reaction partners; Condensation;

1,6 hexanediol diglycidyl ether (16096-31-4) + 2-methyl-2-morpholin-4-yl-1-(4-piperazinylphenyl)propan-1-one (886463-09-8) → C48H76N6O8

Conditions	Yield
1,8-diazabicyclo[5.4.0]undec-7-ene In toluene for 10h; Heating / reflux;

2-Benzoylbenzoic acid (85-52-9) + 1,6 hexanediol diglycidyl ether (16096-31-4) → C40H42O10

Conditions	Yield
With triphenylphosphine at 110℃; for 8h;

1,6 hexanediol diglycidyl ether (16096-31-4) + malonic acid dimethyl ester (108-59-8) → 1,6-bis[(γ-butyrolactone-4-yl)methyloxy]hexane

Conditions	Yield
Stage #1: 1,6-diglycidyloxy hexamethylene; malonic acid dimethyl ester With potassium tert-butylate In tert-butyl alcohol for 16h; Reflux; Stage #2: With sodium hydroxide In tert-butyl alcohol at 70℃; for 5h;	64 g

1,6 hexanediol diglycidyl ether (16096-31-4) + 1,6-hexanediol (629-11-8) + Octamethyltrisiloxane (107-51-7) + acrylic acid (79-10-7) → C84H178O36Si6

Conditions	Yield
Stage #1: octamethyltrisiloxabe; acrylic acid With dihydrogen hexachloroplatinate at 80℃; for 48h; Stage #2: 1,6-diglycidyloxy hexamethylene With tetrabutylammomium bromide; hydroquinone at 100℃; for 14h; Stage #3: 1,6-hexanediol With sulfuric acid at 140℃; for 6h;

1,6 hexanediol diglycidyl ether (16096-31-4) + 2,2-bis(hydroxymethyl)propionic acid (4767-03-7) → C22H42O12

Conditions	Yield
With triphenylphosphine at 140℃; for 3h;

1,6 hexanediol diglycidyl ether (16096-31-4) + carbon dioxide (124-38-9) → C14H22O8

Conditions	Yield
With [N,N'-bis(2-pyridinylmethyl)cyclohexane-1,2-diamine]iron(II) chloride; tetrabutylammomium bromide In neat (no solvent) at 100℃; under 22502.3 Torr; for 4h; Catalytic behavior; Time; Autoclave; Glovebox; Green chemistry;

1,6 hexanediol diglycidyl ether (16096-31-4) + C12H18N2 → C37H64N2O8

Conditions	Yield
at 75℃; for 3h;

1,6 hexanediol diglycidyl ether (16096-31-4) + 1,2-diamino-benzene (95-54-5) → C18H28N3O4(1+)

Conditions	Yield
Stage #1: 1,6-diglycidyloxy hexamethylene; 1,2-diamino-benzene at 65℃; for 1.5h; Inert atmosphere; Stage #2: With sulfuric acid; sodium nitrite In water at -10℃; for 3.5h;

Upstream product

• 81866-56-0 1,6-bis(allyloxy)hexane 
• 20387-39-7 1-chloro-3-[6-(3-chloro-2-hydroxy-propoxy)-hexyloxy]-propan-2-ol 
• 629-11-8 1,6-hexanediol 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 106-89-8 epichlorohydrin 

Downstream Products

• 121-24-4 oxidized glutathione 

Relevant articles and documents

Diol glycidyl ether-bridged cyclens: Preparation and their applications in gene delivery

Polymeric 1,4,7,10-tetraazacyclododecanes (cyclens) using diol glycidyl ether with different chain length as bridges (5a-e) were designed and synthesized from various diols, 1,7-diprotected cyclen and epichlorohydrin. The molecular weights of the title polymers were measured by GPC with good polydispersity. Agarose gel retardation and fluorescent titration using ethidium bromide showed good DNA-binding ability of 5. They could retard plasmid DNA (pDNA) at an N/P ratio of 4-6 and form polyplexes with sizes around 100-250 nm from an N/P ratio of 10 to 60 and relatively low zeta-potential values (5-22 mV). The cytotoxicity of 5 assayed by MTT is much lower than that of 20 kDa PEI. In vitro transfection against A549 and 293 cells showed that the transfection efficiency (TE) of 5c/DNA polyplexes is close to that of 20 kDa PEI at an N/P ratio of 5. Structure-activity relationship (SAR) of 5 was discussed in their DNA-binding, cytotoxicity, and transfection studies. The TE of 5c/DNA polyplexes could be improved by the introduction of 50 μM of chloroquine, the endosomolytic agents, to pretreated cells. These studies may extend the application areas of macrocyclic polyamines, especially for cyclen.

PROCESS FOR PRODUCING EPOXY COMPOUND

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Metabolic inactivation of five glycidyl ethers in lung and liver of humans, rats and mice in vitro

1. Some glycidyl ethers (GE) have been shown to be direct mutagens in short-term in vitro tests and consequently GE are considered to be potentially mutagenic in vivo. However, GE may be metabolically inactivated in the body by two different enzymatic routes: conjugation of the epoxide moiety with the endogenous tripeptide glutathione (GSH) catalysed by glutathione S-transferase (GST) or hydrolysis of the epoxide moiety catalysed by epoxide hydrolase (EH). 2. The metabolic inactivation of five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), has been studied in subcellular fractions of human, C3H mouse and F344 rat liver and lung. 3. All GE were chemically very stable and resistant to aqueous hydrolysis, but were rapidly hydrolysed by EH in cytosolic and microsomal fractions of liver and lung. The aromatic GE were very good substrates for EH. In general, microsomal EH is more efficient than cytosolic EH in hydrolysis of GE, and human microsomes are more efficient than rodent microsomes. 4. The more water-soluble GE, o-CGE and HDDGE, were good substrates for GST whereas the more lipophilic GE, YX4000 and C12GE, were poor substrates for GST. In general, rodents are more efficient in GSH conjugation of GE than humans. 5. In general, the epoxide groups of YX4000 are the most and those of HDDGE the least efficiently inactivated of the five GE under study. For the other three GE no general trend was observed: the relative efficiency of inactivation varied with organ and species. 6. The large variation in metabolism observed with five representative GE indicate that GE have variable individual properties and should not be considered as a single, homogenous class of compounds.