13352-75-5

Basic information

• Product Name: 2,4,6,8,10-Pentaoxaundecane
• Synonyms: 2,4,6,8,10-Pentaoxaundecane
• CAS NO: 13352-75-5
• Molecular Formula: C₆H₁₄O₅
• Molecular Weight: 166.17236
• Mol File: 13352-75-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: -8--6.5 °C
• Boiling Point: 76-80℃/8Torr
• Appearance: /
• Density: 1.0671 g/cm3(Temp: 25 °C)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,4,6,8,10-Pentaoxaundecane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6,8,10-Pentaoxaundecane(13352-75-5)
• EPA Substance Registry System: 2,4,6,8,10-Pentaoxaundecane(13352-75-5)

Safety Data

• Hazardous Substances Data: 13352-75-5(Hazardous Substances Data)

Usage

General Description

2,4,6,8,10-Pentaoxaundecane, also known as undecaethylene glycol, is a chemical compound with the molecular formula C11H24O5. It is a type of polyethylene glycol, which is a polymer made up of repeating ethylene oxide units. 2,4,6,8,10-Pentaoxaundecane is a water-soluble compound that is commonly used as a solvent, in cosmetics, and in various industrial applications. It is also used in the formulation of pharmaceuticals and as a surfactant in household and personal care products. 2,4,6,8,10-Pentaoxaundecane has a wide range of uses due to its ability to dissolve in both water and organic solvents, making it suitable for a variety of applications.

Synthetic route

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) + Dimethoxymethane (109-87-5) → POMM4 (13352-75-5)

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) + 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) + 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) → POMM4 (13352-75-5)

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) + 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) → Dimethyl ether (115-10-6) + Methyl formate (107-31-3) + POMM4 (13352-75-5)

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.

POMM4 (13352-75-5) + 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 = 81.0 %;

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 534-15-6 1,1-dimethoxyethane 
• 628-90-0 bis(methoxymethyl)ether 
• 50-00-0 formaldehyd 
• 67-56-1 methanol 
• 109-87-5 Dimethoxymethane 
• 7664-93-9 sulfuric acid 

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

Shape selectivity extending to ordered supermicroporous aluminosilicates

In the synthesis of polyoxymethylene dimethyl ethers (PODEn) catalyzed by ordered supermicroporous aluminosilicates, shape selectivity was observed and the high selectivity for target products (PODE3-8) was attributed to the particul

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

Towards a Sustainable Synthesis of Oxymethylene Dimethyl Ether by Homogeneous Catalysis and Uptake of Molecular Formaldehyde

Oxymethylene dimethyl ethers (OMEn; CH3(-OCH2-)nO-CH3, n=3–5) are a novel class of sustainable synthetic fuels, which are of increasing interest due to their soot-free combustion. Herein a novel anhyd

By poly-formaldehyde systems poly formaldehyde method of dimethyl ether

The invention relates to a method for preparing polyoxymethylene dimethyl ether from paraformaldehyde, and mainly solves the problem in the prior art that the cost is relative high when triformol is adopted as a raw material to synthesize polyoxymethylene dimethyl ether. According to the invention, methanol, dimethoxymethane, and paraformaldehyde are adopted as raw materials, wherein the mass ratio of methanol : dimethoxymethane : paraformaldehyde is (0-10) : (0-10) : 1, wherein the quantities of methanol and dimethoxymethane cannot both be 0; the catalyst is chosen from at least one component of the following tombarthite modified solid superacid: SO4/ZrO2-La2O3, SO4/ZrO2-Ce2O3, Cl/TiO2-La2O3, Cl/TiO2-Ce2O3, Cl/Fe2O3-Ce2O3, SO4/Al2O3-La2O3 or S2O8/ZrO2-La2O3. The technical scheme excellently solves the problem, and can be applied to the industrial production of polyoxymethylene dimethyl ether.