Physical Properties and Potential Toxicity of Diethylene Glycol Dibutyl Ether in Industrial Applications

Introduction

Diethylene glycol dibutyl ether (DEGDBE) is a versatile solvent and intermediate widely used in polyurethane coatings, polymer processing, and specialty chemicals. Structurally related to diethylene glycol dimethyl ether (DEGDBE) shares chemical characteristics that influence its behavior in industrial and environmental contexts. Studies on related ethers highlight their roles as blocking agents in one-component polyurethane systems, offering improved film performance and processing stability. However, research also underscores potential developmental toxicity in animal models, linking similar glycol ethers to adverse fetal growth and morphological effects.

Densities of Diethylene Glycol Dibutyl Ether

Due to their miscibility with water and with organic solvents, as well as their favorable properties (low vapor pressure, low toxicity, low viscosity, and high chemical stability), glycol ethers are widely used as industrial solvents in a variety of applications, including inks, paints, coatings, brake fluids, and cleaners. For industrial applications of glycol ethers, accurate density data are necessary. New experimental data are reported for densities of diethylene glycol dibutyl ether (DEGDBE) from (283.15 to 363.15) K at pressures up to 60 MPa. [1]

Diethylene Glycol Dibutyl Ether and Toxicity

Diethylene glycol dimethyl ether is structurally related to several compounds which produce reproductive and developmental toxicity, including teratogenicity inlaboratory animals. In the present study, diethylene glycol dimethyl ether (0, 62.5, 125, 250, or 500 mg/kg/day) was administered by gavage in distilled water to timed-pregnant CD-1 mice during major organogenesis (gestational days (gd) 6–15]. Clinical status of treated females was monitored daily during treatment and on gd 17. At sacrifice (gd 17), pregnancy was confirmed by uterine examination for 20–24 dams per group; each live fetus was examined for external, visceral, and skeletal malformations. No maternal deaths, morbidity, or treatment-related clinical signs were observed. Reduced maternal weight gain during treatment at ≥250 mg/kg/day was primarily attributed to compromised pregnancy status resulting in reduced gravid uterine weight. Maternal weight gain during gestation corrected for gravid uterine weight, and relative liver weight (% body weight) were not affected. Average fetal body weight/litter was significantly reduced at ≥125 mg/kg/day. The percentage of postimplantation loss/litter (5, 8, 7, 12, and 50% for control through high dose) and the percentage of malformed live fetuses/litter (0.4, 0, 2, 24, and 96%) were significantly increased at ≥250 mg/kg/day. Developmental defects involved primarily the neural tube, limbs and digits, craniofacial structures, abdominal wall, cardiovascular system, urogenital organs, and both the axial and appendicular skeleton. In summary, oral administration of diethylene glycol dimethyl ether during major organogenesis did not produce any distinctive signs of maternal toxicity, but did produce selective and profound adverse effects upon fetal growth, viability, and morphological development at ≥125 mg/kg/day. [2]

Conformational Changes in Diethylene Glycol Dimethyl Ether

Conformational changes in diethylene glycol dimethyl ether induced by complexation with lithium trifluoromethanesulfonate (LiCFSS03) have been investigated using Raman scattering and infrared transmission spectroscopy. In both the diethylene glycol dimethyl ether and polymer complex new bands were observed in spectral regions involving a significant amount of CH₂ bending motion. These bands are attributed to a conformation which is not energetically favored in the pure polymer or oligomer but which is stabilized through interactions of the cation with the polyether oxygen atoms. Polarized Raman spectra of the glyme and the glyme-salt complex in parallel and perpendicular scattering geometries establish that the intense mode in the CH₂ rocking region which shifts to higher frequency upon complexation belongs to the totally symmetric irreducible representation, ie., an A symmetry species mode. Ab initio calculations of this frequency as a function of monoglyme conformation show that the frequency sharply increases as the O-C-C-O torsional angle decreases in passing from the TGT conformer to the TOT conformer. [3]

References:

[1] Kang, K., Wang, X., Yang, F., & Prausnitz, J. M. (2016). Densities of diethylene glycol, monobutyl ether, diethylene glycol dibutyl ether, and ethylene glycol monobutyl ether from (283.15 to 363.15) K at pressures up to 60 MPa. Journal of Chemical & Engineering Data, 61(8), 2851-2858.

[2] Price, C. J., Kimmel, C. A., George, J. D., & Marr, M. C. (1987). The developmental toxicity of diethylene glycol dimethyl ether in mice. Fundamental and applied toxicology, 8(1), 115-126.

[3] Frech, R., & Huang, W. (1995). Conformational changes in diethylene glycol dimethyl ether and poly (ethylene oxide) induced by lithium ion complexation. Macromolecules, 28(4), 1246-1251.

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