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

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

Uses

Used in Pharmaceutical Formulation:
2,4,6,8,10-Pentaoxaundecane is used as a pharmaceutical excipient for its ability to dissolve a wide range of active pharmaceutical ingredients, enhancing solubility and bioavailability.
Used in Cosmetics:
In the cosmetics industry, 2,4,6,8,10-Pentaoxaundecane is used as a humectant to retain moisture in skin and hair products, providing hydration and improving texture.
Used in Industrial Applications:
2,4,6,8,10-Pentaoxaundecane is utilized as a solvent in various industrial processes due to its capacity to dissolve both polar and non-polar substances, facilitating chemical reactions and material processing.
Used in Household and Personal Care Products:
As a surfactant, 2,4,6,8,10-Pentaoxaundecane is employed in household and personal care products to lower surface tension, improving the spread and effectiveness of these products.
Used in Chemical Synthesis:
2,4,6,8,10-Pentaoxaundecane serves as an intermediate in the synthesis of more complex organic compounds, contributing to the development of new materials and chemical products.

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

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

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 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%.

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

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.

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.

Polyoxymethylene to dimethyl ether synthesis method of polyoxymethylene

The invention relates to a method for synthesizing polyoxymethylene dimethyl ether by using polyoxymethylene, and the method is mainly used for solving the problems of low reaction efficiency of the traditional catalyst and relatively high cost caused by taking trioxymethylene as a raw material. The problems are better solved according to the technical scheme that methanol, dimethoxymethane and polyoxymethylene are used as raw materials, wherein the mass ratio of methanol to dimethoxymethane to polyoxymethylene is (0-10):(0-10):1, the dosages of methanol and dimethoxymethane cannot be simultaneously equal to zero, the raw materials are in contact with a catalyst to react to generate polyoxymethylene dimethyl ether under the conditions that the reaction temperature is 70-200 DEG C and the reaction pressure is 0.2-6MPa, the dosage of the catalyst accounts for 0.05-10% of the weight of the raw materials, and the adopted catalyst comprises the following components in parts by weight: 30-80 parts of molecular sieve carriers (a) and 20-70 parts of rare earth modified solid super acid (b). The method can be used for industrial production of polyoxymethylene dimethyl ether.

REACTION SYSTEM AND PROCESS FOR PREPARING POLYMETHOXY DIMETHYL ETHER

The invention relates to a reaction system and process for continuously preparing polymethoxy dimethyl ether (DMM3-8) by a continuous acetalization reaction between an aqueous formaldehyde solution or paraformaldehyde and methanol in the presen

Reaction system and process for preparing polymethoxy dimethyl ether

The invention relates to a reaction system and process for continuously preparing polymethoxy dimethyl ether (DMM3-8) by a continuous acetalization reaction between an aqueous formaldehyde solution or paraformaldehyde and methanol in the presence of a functionalized acidic ionic liquid as a catalyst. The reaction system of the invention preferably comprises a formaldehyde-concentrating unit, a vacuum-drying unit, an acetalization reaction unit, a product-separating unit and a catalyst-regenerating unit. The process of the invention uses aqueous formaldehyde solution as an initial raw material, which is concentrated in the formaldehyde-concentrating unit to a concentrated formaldehyde of 50～80 wt.%, and vacuum-dried to paraformaldehyde, or uses paraformaldehyde as raw material directly, then obtains DMM3-8 by an acetalization reaction. The raw materials of the reaction used in the invention are cheap and available easily, and the utilization rate of formaldehyde is high; an efficient separation between the catalyst and product, as well as the reuse of the catalyst and raw materials, are realized by a separation mode of combining extraction and rectification together.

A method for synthesizing polyoxymethylene dimethyl ethers

The present invention relates to the field of chemical engineering and technology, in particular relates to the sub-field of synthesis of high quality alternative liquid engine fuel from non-petroleum based feedstock, more particularly relates to a method