13353-03-2

Basic information

• Product Name: 2,4,6,8-Tetraoxanonane
• Synonyms: 2,4,6,8-Tetraoxanonane;2,4,6,8-Tetraoxanone
• CAS NO: 13353-03-2
• Molecular Formula: C₅H₁₂O₄
• Molecular Weight: 136.14638
• Mol File: 13353-03-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: -42--40.5 °C
• Boiling Point: 158-159℃
• Appearance: /
• Density: 1.0242 g/cm3(Temp: 25 °C)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,4,6,8-Tetraoxanonane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6,8-Tetraoxanonane(13353-03-2)
• EPA Substance Registry System: 2,4,6,8-Tetraoxanonane(13353-03-2)

Safety Data

• Hazardous Substances Data: 13353-03-2(Hazardous Substances Data)

Synthetic route

formaldehyd (50-00-0) + methoxymethanol (4461-52-3) → bis-methoxymethoxy-methane (13353-03-2)

Conditions	Yield
With acetic acid Reflux;	96.2%

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With sulfuric acid at 109.99℃; under 7500.75 Torr;	A n/a B 26%

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

Conditions	Yield
With ZrO2#dotLa2O3 at 130℃; under 6000.6 Torr; for 4h; Pressure; Reagent/catalyst;	A 23% B 23.3% C 14.9%

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
With La2O3 doped titania at 130℃; under 4500.45 Torr; for 4h; Reagent/catalyst; Pressure; Autoclave;	A 22.4% B 17.5% C 8.4%
With macroporous strong acidic styrene type cation exchange resin catalyst at 100℃; under 15001.5 Torr; for 10h; Temperature; Time; Overall yield = 51.66 %;
With Cl -/TiO2-La2O3/SBA-15 (Si/Al=38) at 130℃; under 4500.45 Torr; for 4h; Reagent/catalyst; Temperature; Pressure;

methanol (67-56-1) + formaldehyd (50-00-0) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With ZrO2#dotLa2O3 at 130℃; under 5250.53 Torr; for 4h;	A 8.3% B 16.7%

methanol (67-56-1) + formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2)

Conditions	Yield
With sulfuric acid

methanol (67-56-1) + formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) + sulfuric acid (7664-93-9) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

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-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
sulfuric acid In water at 100℃; for 16h; Product distribution / selectivity;

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

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → 1,3,5-Trioxan (110-88-3) + 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) + CH3-(OCH2)7-OCH3 (13353-04-3) + C14H30O13 + C15H32O14 + CH3-(OCH2)6-OCH3 (13352-77-7)

Conditions	Yield
With sulfuric acid at 55 - 115℃; Inert atmosphere;

...Expand

1,3,5-Trioxan (110-88-3) + formaldehyd (50-00-0) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0)

Conditions	Yield
With strong acidic styrene type cation exchange resin catalyst at 100℃; under 15001.5 Torr; for 3h; Temperature; Time; Overall yield = 43.26 %;

1,3,5-Trioxan (110-88-3) + formaldehyd (50-00-0) → bis-methoxymethoxy-methane (13353-03-2) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
With strong acidic styrene type cation exchange resin catalyst at 80 - 100℃; under 15001.5 Torr; for 3h; Temperature; Time; Overall yield = 47.55 %;

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

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)

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) → 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) → bis-methoxymethoxy-methane (13353-03-2)

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

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

Conditions	Yield
With SO42-/ZrO2-La2O3/SBA-15 (Si/Al=50) at 90℃; for 4h;

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)

Conditions	Yield
With SO42-/ZrO2-La2O3/SBA-15 (Si/Al=25) at 130℃; under 6000.6 Torr; for 4h; Reagent/catalyst; Temperature;

formaldehyd (50-00-0) + Dimethoxymethane (109-87-5) → bis-methoxymethoxy-methane (13353-03-2) + Dimethyl ether (115-10-6) + Methyl formate (107-31-3)

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) + bis(methoxymethyl)ether (628-90-0) + POMM4 (13352-75-5)

Conditions	Yield
With Amberlyst A15 resin at 50℃; for 1h;	A 33 %Chromat. B 48 %Chromat. C 12 %Chromat.

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.

bis-methoxymethoxy-methane (13353-03-2) + 6-ethyl-o-toluidine → 2-methyl-6-ethyl-N-(methoxymethoxymethyl)aniline

Conditions	Yield
In benzene at 75 - 80℃; for 18h;	97.2%

bis-methoxymethoxy-methane (13353-03-2) + 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 = 87.7 %;

Upstream product

• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 109-87-5 Dimethoxymethane 
• 7664-93-9 sulfuric acid 
• 110-88-3 1,3,5-Trioxan 
• 4461-52-3 methoxymethanol 
• 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 

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