Table 2.
Glyme | Freezing point (°C) |
Boiling point (°C) |
Dynamic viscosity (mPa s) at 20 °C |
p (mm Hg) at 20 °Cd |
Density (g/mL) at 25 °Cv |
Flash point (°C)e |
LD50 (mg/Kg)f |
Solubility (20 °C) |
|
---|---|---|---|---|---|---|---|---|---|
Monoglyme (G1) | −69.0b,c,h | 85.2,b,h 85,c 84.5mm |
0.4236,o 0.432,q 0.417,bb 0.420,cc 0.455,ll 1.1(20 °C)b,h |
54b,h | 0.86124,j 0.86207,n 0.86132,o 0.8605,q 0.8613,s 0.86114,t,u 0.864,w 0.86260,y 0.86155,z 0.8615,bb 0.8626,cc,dd 0.8612,ii 0.859,ll 0.86370,mm 0.8683 (20 °C),b,h 0.867 (20 °C),c 0.86765 (20 °C),gg |
−6b,c,h | 5370b | miscible with H2O |
|
Ethyl glyme (G1-Et) | −74.0b,h | 121,b 121.4,h 121.2mm |
0.593,bb 0.7 (20 °C),b 0.65 (20 °C)h |
9,b 9.4h | 0.83607,z 0.8362,aa 0.8360,bb 0.83510,mm 0.8417(20 °C),b,h |
27b | 4400b | 20.4% in H2O, 3.3% H2O inb |
|
Butyl glyme (G1-Bu) | −69.1h | 203.6,h 206 (dec)mm |
0.09h | 0.83189,mm 0.8374(20 °C)h |
85h (open cup) |
0.2wt% in H2O, 0.6wt% H2O inh |
|||
Diglyme (G2) | −64.0,a,c −70,g −68h |
162a,c,g | 0.981,m 1.06,x 0.989,bb 0.985,cc 0.991,jj 0.976,nn 2.0 (20 °C),b,h 1.14(20 °C)x |
2,b 3.0 (100 °C)h |
0.93873,j 0.93882,k 0.93924,l 0.9394,m 0.93892,n 0.93871,t 0.93935,u 0.938,w 0.93897,y 0.93875,z 0.9385,bb 0.9389,cc 0.9399,jj 0.9397,kk 0.93961,nn 0.9434 (20 °C),a 0.944 (20 °C),c 0.945 (20 °C),g,h 0.94511 (20 °C)gg |
57,b 51c | 4670b | miscible with H2O, ethanol, diethyl ether |
|
Ethyl diglyme (G2-Et) | −44.3b | 189b | 1.238,bb 1.241,cc1.4 (20 °C)b |
0.5b | 0.9082(20 °C),b 0.9028,z 0.9021,bb 0.9035cc |
90b | 5000b | miscible with H2O |
|
Butyl diglyme (G2-Bu) | −60.2,b −60c |
256b,c | 2.122,cc 2.4 (20 °C)b |
<0.01b | 0.8814(20 °C),b 0.884(20 °C),c 0.87830,z 0.8781cc |
118,b 120c |
3900b | 0.3% in H2O, 1.4% H2O inb,c |
|
Triglyme (G3) | −43.8,a −40,c −45.0h |
218,a 220,c 216h |
1.96,r,nn 2.16,x 1.950,cc 3.8 (20 °C),b,h |
2.41(20 °C)x | 0.02b,h | 0.98001,i 0.98067,j 0.98117,l 0.9795,r 0.98058,t,u 0.981,w 0.98071,y 0.9807,cc 0.98042,ee 0.97981,ff 0.98023,nn 0.986 (20 °C),a,h 0.987 (20 °C),c 0.98569 (20 °C),gg 0.98541 (20 °C)hh |
111,b,h 113c |
5000b | very soluble in H2O, benzene |
Tetraglyme (G4) | −29.7,b,h −30c |
275b,c,h | 3.295,p 3.67,x 3.40,nn 4.1 (20 °C),b,h 4.18(20 °C)x |
<0.01b,h | 1.00662,i 1.00564,j 1.00627,l 1.0047,p 1.00666,t 1.00668,u 1.00628,y 1.00620,ee 1.00743,nn 1.0132(20 °C),b,h 1.0(20 °C),c 1.0116 (20 °C),gg 1.01115 (20 °C)hh |
141b,c,h | 5100b | miscible with H2O |
|
Proglyme (P2) | −71b, −80c |
175b,c | 1.1 (20 °C)b | 0.55b | 0.900(20 °C)b,c | 65b,c | — | 35% in H2O, 4.5% H2O inb,c |
|
PEG-DME 200 | −37c | >300c | 4.3 mm2/s (20 °C)c |
— | 1.01–1.02 (20 °C)c | 154c | — | ||
PEG-DME 250 | −23c | >300c | 7 mm2/s (20 °C),c 7.215 mm2/s (20 °C),gg |
— | 1.02–1.04(20 °C),c 1.0355 (20 °C)gg |
137c | — | ||
Polyglyme (MW=236)b | −28b | 275b | 12 (20 °C)b | 0.01b | 1.03(20 °C)b | 135b | — | ||
Polyglyme (MW=275)b | −23b | 275b | 12 (20 °C)b | <0.01b | 1.04(20 °C)b | >130b | — | miscible with H2O |
|
Higlyme (MW>400)b | −5–10b | >300b | 34 (20 °C)b | 0.1b | 0.975(20 °C)b | 140b | — | miscible with H2O |
|
PEG-DME 500 | 13c | >300c | 25 mm2/s (20 °C)c |
— | 1.05(50 °C)c | 220c | — | ||
PEG-DME 1000 | 36c | >300c | 11 mm2/s (100 °C)c |
— | 1.10(50 °C)c | 260c | — | ||
PEG-DME 2000 | 50c | >300c | 30 mm2/s (100 °C)c |
— | 1.08(60 °C)c | 254c | — |
Note:
Ref,40
production specifications from Novolyte Technologies (now a part of BASF),
production specifications from Clariant (viscosity is kinematic viscosity),
vapor pressure,
closed cup,
acute toxicity,
Ref41,
Ref42,
Ref,43
Ref,44
Ref45 (this reference also reported other thermodynamic properties of diglyme at 25 °C such as dipole moment μ = 1.87 D, heat capacity Cp = 276.9 J mol−1 K−1, etc.),
Ref,46
Ref,47
Ref,48
Ref49 (densities and viscosities of monoglyme at 308.15 K and 318.15 K were also reported),
Ref,50
Ref,51
Ref52 (this reference also reported dielectric constant of 7.62 as well as refractive index and molar refraction for triglyme),
Ref,53
Ref54,
Ref,55
density data for monoglyme and diglyme were reported at temperatures between 293.15 K and 353.15 K and up to 60 MPa,56
Ref,57
Ref,58
Ref59 (density data at 288.18 and 308.15 K were also reported),
Ref,60
Ref,61
Ref62 (densities and viscosities were reported for several glymes from 288.15 K to 343.15 K),
Ref,63
Ref,64
Ref,65
Ref,66
Ref67 (densities, kinematic viscosities and heat capacities were reported for several glymes including pentaethylene glycol dimethyl ether from 283.15 to 423.15 K),
Ref68 (data on density, isentropic compressibility and isothermal compressibility of triglyme and tetraglyme were reported at 293.15–353.15 K and 0.1–100 MPa),
Ref,69
Ref,70
Ref,71
Ref,72
Ref (densities, refractive indexes, and boiling points of other 1,2-disubstituted ethylene glycol derivatives such as propyl glyme were also reported),73
Ref,74