Methoxypropoxypropanol
[CAS# 34590-94-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: Methoxypropoxypropanol
• Synonyms: Dipropyleneglycol monomethyl ether; (2-Methoxymethylethoxy)propanol; DPM; DPGME; Arcosolv Dpm; Dowanol dpm
• Molecular Formula: C₇H₁₆O₃
• Molecular Weight: 148.20
• CAS Registry Number: 34590-94-8
• EC Number: 252-104-2
• SMILES: CC(COC(C)COC)O

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 0.95 g/mL (Expl.)
• Melting point: -80 °C (Expl.)
• Boiling point: 203.3±15.0 °C 760 mmHg (Calc.)^*, 208.3 - 209.4 °C (Expl.)
• Flash point: 76.7±20.4 °C (Calc.)^*, 82.2 °C (Expl.)
• Solubility: Miscible (Expl.)
• Index of refraction: 1.422 (Calc.)^*, 1.422 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H227-H320-H335-H336
• Safety Statements: P501-P261-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P304+P340+P312-P403+P233-P403+P235-P405

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H336
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	2	H371

Discovery and Applications

Methoxypropoxypropanol, also referred to as dipropylene glycol monomethyl ether, was developed in mid‑20th century as part of expanding propylene glycol ether solvents derived from propylene oxide alkylation. It belongs to the family of propylene‑oxide derived glycol ethers, most commonly produced by reacting propylene oxide with methanol under acidic or basic catalysis within continuous industrial processes. Solid base catalysts such as MgO and Al‑pillared clays have been studied for efficient synthesis, promoting methanol dissociation and epoxide ring opening to yield mono‑alkyl‑ ether products with high selectivity under controlled temperature and reactant ratios.

One key study demonstrated synthesis of propylene glycol methyl ether by methanol opening of propylene oxide over MgO and CaO catalysts, revealing that moderate base strength catalysts such as MgO favored high selectivity towards the mono‑ether product, while stronger bases yielded side reactions. Similar catalyst systems have been applied to dipropylene glycol methyl ether (methoxypropoxypropanol) synthesis by controlling propylene oxide feed ratio and temperature to generate di‑ether structures selectively. Al‑pillared clay catalysts (Al‑PILCs) have provided enhanced activity and selectivity by tuning acid‑base properties and surface area.

Applications of methoxypropoxypropanol emerged due to its physicochemical properties: miscibility with water and many organic solvents, boiling point around 190–195 °C, moderate vapor pressure, high solvency for resins, inks, coatings, adhesives, and grease. It functions effectively as a coalescing solvent in formulations to improve film formation in paints and coatings, and as a coupling solvent in cleaning solutions and printing inks to dissolve organic contaminants while maintaining stability and controlled evaporation rates. Its high flash point compared to smaller glycol ethers enhances handling safety.

Safety and toxicological investigations confirm that dipropylene glycol monomethyl ether exhibits low acute toxicity via oral, inhalation, or dermal routes in rodent studies. A 13‑week inhalation toxicity study in rats and rabbits revealed only mild and reversible liver effects at high exposures, with no evidence of teratogenicity or systemic toxicity at realistic use levels. A disposition study using radiolabeled compound showed rapid metabolism and excretion, with major elimination via urine and expired CO₂ within 48 hours, and no significant bioaccumulation. Broader category assessments of propylene glycol ethers indicate that the predominant “alpha” isomer form of these solvents does not form alkoxy‑propionic acid metabolites associated with reproductive toxicity, explaining their favorable safety classification relative to lower molecular weight glycol ethers.

Environmental profiling within regulatory frameworks further classifies methoxypropoxypropanol as readily biodegradable, with low potential for persistence or bioaccumulation. Standard handling recommendations include use of adequate ventilation, avoidance of skin contact and inhalation, and use of personal protective equipment as appropriate. Industrial hygiene standards place it in low‑priority hazard category under screening chemical programs.

Discovery of methoxypropoxypropanol reflects broader innovation in solvent chemistry aimed at combining high solvency, water compatibility, and lower volatility. Its controlled synthesis via epoxide opening, and application in paint, cleaning, ink, and adhesive formulations, illustrate its role as a versatile solvent in industrial and consumer chemical products.

References

Landry TD, Gushow TS, Yano BL (1984) Dipropylene glycol monomethyl ether: a 13‑week inhalation toxicity study in rats and rabbits. Fundam Appl Toxicol 4(4):612–618 DOI: 10.1093/toxsci/4.4.612

Miller RR, Hermann EA, Calhoun LL et al. (1985) Metabolism and disposition of dipropylene glycol monomethyl ether in male rats. Toxicol Sci 5(4):721–726 DOI: 10.1093/toxsci/5.4.721

Timofeeva MN, Panchenko VN, Gil A et al. (2011) Synthesis of propylene glycol methyl ether from methanol and propylene oxide over alumina‑pillared clays. Appl Catal B Environ 102(3‑4):433–440 DOI: 10.1016/j.apcatb.2010.12.020