13352-76-6

Basic information

• Product Name: 2,4,6,8,10,12-Hexaoxatridecane
• Synonyms: 2,4,6,8,10,12-Hexaoxatridecane
• CAS NO: 13352-76-6
• Molecular Formula: C₇H₁₆O₆
• Molecular Weight: 196.19834
• Mol File: 13352-76-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 18.3 °C
• Boiling Point: 123-135℃/8Torr
• Appearance: /
• Density: 1.1003 g/cm3(Temp: 25 °C)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,4,6,8,10,12-Hexaoxatridecane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6,8,10,12-Hexaoxatridecane(13352-76-6)
• EPA Substance Registry System: 2,4,6,8,10,12-Hexaoxatridecane(13352-76-6)

Safety Data

• Hazardous Substances Data: 13352-76-6(Hazardous Substances Data)

Usage

General Description

2,4,6,8,10,12-Hexaoxatridecane, also known as triethylene glycol dimethyl ether or triglyme, is an organic compound primarily used as a solvent or plasticizer. It is a colorless liquid with a very high boiling point and is also used as a stabilizer in various manufacturing industries. The compound's chemical formula is C9H20O6 and its molecular weight is 236.25 g/mol. It has the capability to form hydrogen bonds due to the presence of oxygen atoms. Despite its usefulness, it should be handled with care as it can cause skin and eye irritation, and prolonged or repeated exposure can lead to serious health issues. Therefore, safety measures must be strictly adhered to while dealing with this substance.

Synthetic route

1,3,5-Trioxan (110-88-3) + 1,1-dimethoxyethane (534-15-6) → C11H24O10 + C13H28O12 + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane (54261-86-8) + POMM5 (13352-76-6) + CH3-(OCH2)7-OCH3 (13353-04-3) + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
Amberlite IR 120 at 100℃; for 24h; Product distribution / selectivity;
trifluorormethanesulfonic acid at 100℃; for 40h; Product distribution / selectivity;
sulfuric acid In water at 100℃; for 12h; Product distribution / selectivity;

...Expand

1,3,5-Trioxan (110-88-3) + 1,1-dimethoxyethane (534-15-6) + bis(methoxymethyl)ether (628-90-0) → C11H24O10 + C13H28O12 + bis-methoxymethoxy-methane (13353-03-2) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane (54261-86-8) + POMM5 (13352-76-6) + CH3-(OCH2)7-OCH3 (13353-04-3) + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
sulfuric acid In water at 100℃; for 12h; Product distribution / selectivity;

...Expand

1,3,5-Trioxan (110-88-3) + bis(methoxymethyl)ether (628-90-0) → C11H24O10 + C13H28O12 + 1,1-dimethoxyethane (534-15-6) + bis-methoxymethoxy-methane (13353-03-2) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane (54261-86-8) + POMM5 (13352-76-6) + CH3-(OCH2)7-OCH3 (13353-04-3) + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
sulfuric acid In water at 100℃; for 12h; Product distribution / selectivity;

...Expand

formaldehyd (50-00-0) + 1,1-dimethoxyethane (534-15-6) → C11H24O10 + C13H28O12 + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + Methoxymethoxymethoxymethoxymethoxy-methoxymethoxymethoxymethoxymethoxymethoxy-methane (54261-86-8) + POMM5 (13352-76-6) + CH3-(OCH2)7-OCH3 (13353-04-3) + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
Amberlite IR 120 at 100℃; for 8h; Product distribution / selectivity;

...Expand

methanol (67-56-1) + formaldehyd (50-00-0) → bis-methoxymethoxy-methane (13353-03-2) + POMM4 (13352-75-5) + POMM5 (13352-76-6)

Conditions	Yield
With C16H36NO3S(1+)*CH3O4S(1-) at 125 - 130℃; under 26252.6 - 30003 Torr; Reagent/catalyst; Inert atmosphere;

methanol (67-56-1) + formaldehyd (50-00-0) → Dimethoxymethane (109-87-5) + bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + POMM5 (13352-76-6)

Conditions	Yield
With C16H36NO3S(1+)*CH3O4S(1-) In water at 125 - 130℃; under 26252.6 - 30003 Torr; Reagent/catalyst;

1,3,5-Trioxan (110-88-3) + Dimethoxymethane (109-87-5) → POMM5 (13352-76-6)

Conditions	Yield
With C13H25N2O3S(1+)*HO4S(1-) at 150℃; for 10h; Autoclave;

1,3,5-Trioxan (110-88-3) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + POMM5 (13352-76-6)

Conditions	Yield
With C10-AS-50 at 105℃; under 9750.98 Torr; for 2h; Catalytic behavior; Inert atmosphere;

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5) + CH3-(OCH2)8-OCH3 (13352-78-8) + POMM5 (13352-76-6) + CH3-(OCH2)7-OCH3 (13353-04-3) + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
With lanthanum(III) sulfate at 130℃; under 3750.38 Torr; for 6h; Reagent/catalyst; Concentration; Time; Temperature; Pressure; Overall yield = 75.5 %;	A 20.74 %Chromat. B 25.87 %Chromat. C 13.77 %Chromat. D 1.11 %Chromat. E 8.14 %Chromat. F 2.37 %Chromat. G 4.23 %Chromat.

...Expand

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → Dimethyl ether (115-10-6) + Methyl formate (107-31-3) + POMM5 (13352-76-6)

Conditions	Yield
With C16AlF36O4(1-)*C3H9O(1+) at 25 - 30℃; Schlenk technique; Inert atmosphere;

1,3,5-Trioxan (110-88-3) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + POMM4 (13352-75-5) + POMM5 (13352-76-6)

Conditions	Yield
With Amberlyst A15 resin at 50℃; for 1h;	A 42 %Chromat. B 29 %Chromat. C 14 %Chromat.

POMM5 (13352-76-6) + phenol (108-95-2) → Bis(2-hydroxyphenyl)methane (2467-02-9) + 2-[(4-hydroxyphenyl)methyl]phenol (2467-03-0) + bis-(4-hydroxyphenyl)methane (620-92-8)

Conditions	Yield
With phosphoric acid In water at 80℃; for 4h; Overall yield = 74.8 %;

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 109-87-5 Dimethoxymethane 
• 50-00-0 formaldehyd 
• 67-56-1 methanol 
• 534-15-6 1,1-dimethoxyethane 
• 628-90-0 bis(methoxymethyl)ether 

Downstream Products

• 2467-02-9 Bis(2-hydroxyphenyl)methane 
• 2467-03-0 2-[(4-hydroxyphenyl)methyl]phenol 
• 620-92-8 bis-(4-hydroxyphenyl)methane 

Relevant articles and documents

AQUEOUS COMPOSITION BASED ON POLYOXYMETHYLENE DIALKYL ETHERS (POM) AND THEIR USE FOR THE PRESERVATION AND/OR EMBALMING OF THE HUMAN OR ANIMAL BODY

The invention relates to a composition comprising: a) a mixture of polyoxymethylene dialkyl ethers (POM) having a restricted specific molecular distributionb) at least one biocidal agentc) at least one pro-penetrating agentd) at least one dyee) optionally, another additiveand water as diluent. It also relates to a non-therapeutic method of preserving and/or embalming a dead human or animal body using the composition, such as the use of this composition for anatomopathological purposes.

Synthesis of polyoxymethylene dimethyl ethers catalyzed by rare earth compounds

Polyoxymethylene dimethyl ethers (PODMEn) have been synthesized in moderate yields by the reaction of methylal (PODME1) and paraformaldehyde catalyzed by rare earth compounds. The activities of catalyst in the reaction were investigated and the

Synthesis of polyoxymethylene dimethyl ethers from methylal and trioxane catalyzed by Br?nsted acid ionic liquids with different alkyl groups

Br?nsted acid ionic liquids with different alkyl group carbon chain lengths and an alkane sulfonic acid group were synthesized through bromoalkane, imidazole and 1,4-butane sultone as raw materials. The structures and properties of the ionic liquids were experimentally characterized. Catalytic reaction of methylal (DMM) with trioxane (TOX) for preparation of polyoxymethylene dimethyl ethers (PODMEn, CH3O(CH2O)nCH3, where n > 1) was investigated in various Br?nsted acid ionic liquids with different carbon chain length of alkyl groups. The carbon chain length of alkyl groups and activity correlation for the ionic liquids was studied. It was found that the structures of ionic liquids were consistent with the designed structure and their purities were high. They possessed high thermal stability and wide liquid range. The hydrophobicity of ionic liquids became stronger with the increase of carbon chain length. With increasing the carbon chain length of ionic liquids, the selectivity of PODME3-8 is increased at first and then decreased. Among all the ionic liquids, [C6ImBS][HSO4] shows the best catalytic performance and the selectivity of PODME3-8 is 57.85%.