2568-90-3

Basic information

• Product Name: FORMALDEHYDE DI-N-BUTYL ACETAL
• Synonyms: DI-N-BUTOXYMETHANE;FORMALDEHYDE DI-N-BUTYL ACETAL;1,1'-[methylenebis(oxy)]dibutane;FORMALDEHYDE DI-N-BUTYL ACETAL 98+%;Butane, 1,1-methylenebis(oxy)bis-;5,7-Dioxahendecane;5,7-Dioxaundecane;Bis(butyloxy)methane
• CAS NO: 2568-90-3
• Molecular Formula: C₉H₂₀O₂
• Molecular Weight: 160.25
• EINECS: 219-909-0
• Mol File: 2568-90-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: -58.1°C
• Boiling Point: 180°C
• Flash Point: 60°C
• Appearance: /
• Density: 0,84 g/cm3
• Vapor Pressure: 1.29mmHg at 25°C
• Refractive Index: n20/D1.406
• Water Solubility: 222.5-250mg/L at 20℃
• CAS DataBase Reference: FORMALDEHYDE DI-N-BUTYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: FORMALDEHYDE DI-N-BUTYL ACETAL(2568-90-3)
• EPA Substance Registry System: FORMALDEHYDE DI-N-BUTYL ACETAL(2568-90-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3271
• WGK Germany: 1
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2568-90-3(Hazardous Substances Data)

Usage

Uses

Formaldehyde dibutyl acetal is a halogen-free and less toxic solvent that can be used to solubilize commercial low-density polyethylene (LDPE) samples to analyze molecular weight distribution using gel permeation chromatography (GPC). It can also be used as a reactant to prepare butoxymethyltriphenylphosphonium iodide, which is used for carbon homologation and also as a useful key intermediate in organic synthesis.

Preparation

A flask containing 15 gm (0.5 mole) of paraformaldehyde, 74 gm (1.0 mole) of η-butyl alcohol, and 2.0 gm of anhydrous ferric chloride is refluxed for 10 hr. The lower layer of 3-4 ml of material is discarded and then 50 ml of 10% aqueous sodium carbonate solution is added to remove the ferric chloride as ferric hydroxide. The product is shaken with a mixture of 40 ml of 20% hydrogen peroxide and 5 ml of 10% sodium carbonate solution at 45°C in order to remove any remaining aldehyde. The product is also washed with water, dried, and distilled from excess sodium metal to afford 62 gm (78%).

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 3341, 1980 DOI: 10.1021/jo01304a039

General Description

Formaldehyde dibutyl acetal is an acetal used in the manufacture of synthetic resins, antiseptics, deodorants, and fungicides. It is also used as a fuel additive to increase the octane number of gasoline or the n-cetane number of diesel fuels and reduce smoke and particulate emissions.

InChI:InChI=1/C9H20O2/c1-3-5-7-10-9-11-8-6-4-2/h3-9H2,1-2H3

Synthetic route

formaldehyd (50-00-0) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With aminosulfonic acid Reflux;	96.8%
With kaolin for 12h; Heating;	80%
With Montmorillonite K 10 for 12h; Heating;	72%

n-Butyl nitrite (544-16-1) + 4-bromo-N,N-dimethylaniline (586-77-6) → di-n-butyloxymethane (2568-90-3) + 4-bromo-N-nitroso-N-methylaniline (937-23-5)

Conditions	Yield
With water; ammonium chloride for 0.25h; Product distribution; Heating; also PTSA instead of NH4Cl;	A n/a B 88%

4-bromo-N,N-dimethylaniline (586-77-6) → di-n-butyloxymethane (2568-90-3) + 4-bromo-N-nitroso-N-methylaniline (937-23-5)

Conditions	Yield
With n-Butyl nitrite; water; ammonium chloride for 0.25h; Heating;	A n/a B 88%

Dimethoxymethane (109-87-5) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3) + methanol butoxymethoxymethane (89979-37-3)

Conditions	Yield
With h-mordenite In methanol at 120℃; under 22502.3 Torr; for 6h; Reagent/catalyst; Pressure; Temperature; Inert atmosphere; Autoclave; Green chemistry;	A 85% B 9%

4-methoxy-N,N-dimethylanilne (701-56-4) → di-n-butyloxymethane (2568-90-3) + 4-Methoxy-2-nitro-N,N-dimethylbenzeneamine (60049-83-4) + 4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine (130717-81-6)

Conditions	Yield
With n-Butyl nitrite; toluene-4-sulfonic acid for 72h; Ambient temperature;	A n/a B 84% C 2%

1,1-dibromomethane (74-95-3) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water; chlorobenzene at 50℃; for 2h; other alcohols; other solvents; other phase transfer catalysts; var. amounts of KOH and H2O; var. reaction time;	83.22%
With potassium hydroxide; tetrabutylammomium bromide In water; chlorobenzene at 50℃; for 2h;	83.22%
With potassium hydroxide; tetrabutyl-ammonium chloride In benzene at 50℃; for 5h;	70%

tert-butyl 3-bromodiazirine-3-carboxylate (1351865-61-6) + sodium butanolate (2372-45-4) → di-n-butyloxymethane (2568-90-3) + Dibutyl carbonate (542-52-9)

Conditions	Yield
In N,N-dimethyl-formamide; butan-1-ol at 0 - 20℃; for 0.333333h;	A 31% B 82%

dichloromethane (75-09-2) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With sodium hydroxide; Tixogel VP for 72h; Heating;	80%
With potassium hydroxide; methyl-tridecylammonium chloride Heating;

n-Butyl nitrite (544-16-1) + 4-bromo-N,N-dimethylaniline (586-77-6) → formaldehyd (50-00-0) + di-n-butyloxymethane (2568-90-3) + Tributyl orthoformate (588-43-2) + 2,4-dibromo-N,N-dimethylaniline (64230-27-9) + 4-Bromo-N,N-di(n-butoxymethyl)benzeneamine (130717-78-1) + 4-bromo-N-nitroso-N-methylaniline (937-23-5)

Conditions	Yield
for 60h; Product distribution; Heating;	A n/a B 30 % Chromat. C 7 % Chromat. D n/a E 10 % Chromat. F 78%

dimethyl sulfoxide (67-68-5) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With bromine In tetrachloromethane for 4h; Ambient temperature; alcohol addition;	78%

sodium butanolate (2372-45-4) + butyl 3-bromo-3H-diazirine-3-carboxylate (792950-89-1) → di-n-butyloxymethane (2568-90-3) + Dibutyl carbonate (542-52-9)

Conditions	Yield
In N,N-dimethyl-formamide; butan-1-ol at 0 - 20℃; for 0.333333h;	A 35% B 75%

Dimethoxymethane (109-87-5) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With toluene-4-sulfonic acid for 2.5h; Heating;	38%
With SiO2 supported H3PW12O40 at 160℃; under 22502.3 Torr; for 6h; Temperature; Pressure; Autoclave; Inert atmosphere;
With H-ZSM-35 at 70℃; under 7500.75 - 15001.5 Torr; for 10h; Time; Autoclave; Inert atmosphere;
With Amberlyst 15 at 120℃; under 22502.3 Torr; for 6h; Catalytic behavior; Concentration; Pressure; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere;

Dimethoxymethane (109-87-5) + dibutyl acetal (871-22-7) → 1,1-dimethoxyethane (534-15-6) + di-n-butyloxymethane (2568-90-3) + 1-methoxy-1-butoxyethane (75677-94-0) + methoxyisobutoxymethane (76050-98-1)

Conditions	Yield
With KU-2 resin at 40℃; for 5h;	A 26% B 9% C 8% D 31%

diethyl ether (60-29-7) + 1,2-bis(chloromethoxy)ethane (13483-18-6) + sodium butanolate (2372-45-4) → di-n-butyloxymethane (2568-90-3) + 1,2-bis-butoxymethoxy-ethane (5703-97-9) + bis-(2-butoxymethoxy-ethyl) ether (7736-68-7)

Conditions	Yield
weitere Reaktionen mit Natriumalkoholaten in den entsprechenden Alkoholen sowie in Aether;

1,2-bis-chloromethoxy-propane (16721-81-6) + sodium butanolate (2372-45-4) → di-n-butyloxymethane (2568-90-3) + 1-butoxymethoxy-propan-2-ol (59569-56-1) + 1,2-bis-butoxymethoxy-propane (59569-51-6)

Conditions	Yield
Reaktionen mit weiteren Natriumalkoholaten;

1,3-di(chloromethoxy)propane (138418-40-3) + sodium butanolate (2372-45-4) → di-n-butyloxymethane (2568-90-3) + 1,3-bis-butoxymethoxy-propane

Conditions	Yield
With butan-1-ol

1,3-bis-chloromethoxy-butane (89583-59-5) + sodium butanolate (2372-45-4) → di-n-butyloxymethane (2568-90-3) + 1,3-bis-butoxymethoxy-butane (92318-80-4)

Conditions	Yield
With butan-1-ol

1,4-bis(chloromethoxy)crotonylene (138649-02-2) + sodium butanolate (2372-45-4) → di-n-butyloxymethane (2568-90-3) + 1,4-bis-butoxymethoxy-but-2-yne

Conditions	Yield
Reaktionen mit weiteren Natriumalkoholaten;

hexamethylenetetramine (100-97-0) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With hydrogenchloride at 60 - 100℃;

1-(chloromethoxy)butane (2351-69-1) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

1,2-bis(chloromethoxy)ethane (13483-18-6) + sodium butanolate (2372-45-4) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

1-(chloromethoxy)butane (2351-69-1) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride

chloro-trimethyl-silane (75-77-4) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With dimethyl sulfoxide In benzene

bis-methanesulfonyloxymethyl ether (62609-70-5) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
In acetonitrile

n-Butyl nitrite (544-16-1) + 4-methoxy-N,N-dimethylanilne (701-56-4) → di-n-butyloxymethane (2568-90-3) + Tributyl orthoformate (588-43-2) + N-methyl-N-nitroso-p-anisidine (940-11-4) + 4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine (130717-81-6)

Conditions	Yield
With water for 72h; Product distribution; Ambient temperature;	A n/a B n/a C 68 % Chromat. D 28 % Chromat.

n-Butyl nitrite (544-16-1) + 4-methoxy-N,N-dimethylanilne (701-56-4) → di-n-butyloxymethane (2568-90-3) + 4-Methoxy-2-nitro-N,N-dimethylbenzeneamine (60049-83-4) + 4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine (130717-81-6)

Conditions	Yield
With toluene-4-sulfonic acid for 72h; Product distribution; Ambient temperature;	A n/a B 84 % Chromat. C 2 % Chromat.

n-Butyl nitrite (544-16-1) + 4-bromo-N,N-dimethylaniline (586-77-6) → di-n-butyloxymethane (2568-90-3) + 4-Bromo-N-(n-butoxymethyl)-N-methylbenzeneamine (130717-77-0) + 4-bromo-N-nitroso-N-methylaniline (937-23-5)

Conditions	Yield
With ammonium chloride for 0.25h; Product distribution; Heating;	A 4 % Chromat. B 55 % Chromat. C 20 % Chromat.

Dibutoxymethoxy-benzene (49758-73-8) → di-n-butyloxymethane (2568-90-3)

Conditions	Yield
With lithium aluminium tetrahydride; magnesium bromide In diethyl ether Ambient temperature;

formaldehyd (50-00-0) + 1-ethoxymethyl-1H-imidazole (67319-04-4) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3) + 1-Butoxymethyl-3-ethoxymethyl-3H-imidazol-1-ium; chloride (118178-99-7)

Conditions	Yield
With hydrogenchloride 2.) 2 h, 90 deg C; Yield given. Multistep reaction;

formaldehyd (50-00-0) + butan-1-ol (71-36-3) → di-n-butyloxymethane (2568-90-3) + 1-(chloromethoxy)butane (2351-69-1)

Conditions	Yield
With hydrogenchloride Title compound not separated from byproducts;

octanol (111-87-5) + di-n-butyloxymethane (2568-90-3) → formaldehyde-(butyl-octyl-acetal) (84260-76-4)

Conditions	Yield
With Nafion-H SAC-13 silica nanocomposite Heating;	100%

di-n-butyloxymethane (2568-90-3) + 2-phenylethanol (60-12-8) → formaldehyde-(butyl-phenethyl-acetal) (92101-62-7)

Conditions	Yield
With Nafion-H SAC-13 silica nanocomposite at 100℃;	100%

di-n-butyloxymethane (2568-90-3) + benzyl alcohol (100-51-6) → formaldehyde-(benzyl-butyl-acetal) (91764-40-8)

Conditions	Yield
With toluene-4-sulfonic acid Heating;	99%

2,6-diethylaniline (579-66-8) + di-n-butyloxymethane (2568-90-3) → 2,6-diethyl-N-(butoxymethyl)aniline

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 135 - 140℃; for 9h;	96.2%

dimethylformamide [DMF] + di-n-butyloxymethane (2568-90-3) + tralopyril (122454-29-9) → 4-Bromo-1-(n-butoxymethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Conditions	Yield
With triethylamine; trichlorophosphate In water	94.6%

di-n-butyloxymethane (2568-90-3) + rac-octan-2-ol (4128-31-8) → 2-butoxymethoxy-octane

Conditions	Yield
With Nafion-H SAC-13 silica nanocomposite In benzene Heating;	88%

di-n-butyloxymethane (2568-90-3) + Dichlorophenylphosphine (644-97-3) → (butoxymethyl)phenylphosphinic acid (75425-74-0)

Conditions	Yield
With zinc(II) chloride at 110℃; for 4h;	87.7%

di-n-butyloxymethane (2568-90-3) + cyclohexanol (108-93-0) → Cyclohexyl--ether (91243-24-2)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	86%

di-n-butyloxymethane (2568-90-3) + chlorodiphenylphosphonium tetrachloroaluminate → (butoxymethyl)diphenylphosphine oxide (75425-77-3)

Conditions	Yield
In diethyl ether for 1.5h; Heating;	85%

dibutyl chlorophosphite (4124-92-9) + di-n-butyloxymethane (2568-90-3) → O,O-dibutyl(butoxymethyl)phosphonate (59375-49-4)

Conditions	Yield
With zinc(II) chloride at 80℃; for 7h;	84.5%

di-n-butyloxymethane (2568-90-3) + 1-Phenylethanol (98-85-1, 13323-81-4) → (1-butoxyethyl)benzene (4157-77-1) + 1-Phenethyl-methoxy-butylether (92423-62-6)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	A 16% B 84%
With Nafion-H SAC-13 silica nanocomposite In benzene Heating;	A 58% B 42%

di-n-butyloxymethane (2568-90-3) + butyl glycolate (7397-62-8) → Butoxymethoxy-acetic acid butyl ester + Butoxycarbonylmethoxymethoxy-acetic acid butyl ester

Conditions	Yield
With toluene-4-sulfonic acid at 130 - 150℃; for 5h;	A 83% B 7%

di-n-butyloxymethane (2568-90-3) + cholesterol (57-88-5) → (3S,8S,9S,10R,13R,14S,17R)-3-Butoxymethoxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

Conditions	Yield
With Nafion-H SAC-13 silica nanocomposite In benzene Heating;	83%

di-n-butyloxymethane (2568-90-3) + 3-chloro-2-hydroxy-propionic acid butyl ester (60593-60-4) → 2-Butoxymethoxy-3-chloro-propionic acid butyl ester

Conditions	Yield
With toluene-4-sulfonic acid at 130 - 150℃; for 5h;	78%

di-n-butyloxymethane (2568-90-3) + 1,4-bis(trimethylsilyl)-2-butyne (21752-78-3) → (2-Butoxymethyl-buta-2,3-dienyl)-trimethyl-silane (80404-94-0) + 2,3-Bis-butoxymethyl-buta-1,3-diene (80405-01-2)

Conditions	Yield
With titanium tetrachloride In dichloromethane Product distribution; -60 deg C, 15 min, from -60 deg C to 0 deg C, 15 min, 0 deg C, 15 min; various acetal/TiCl4/silane ratio, several acetals;	A 77% B n/a
With titanium tetrachloride In dichloromethane 1.) -60 deg C, 15 min, 2.) from -60 deg C to 0 deg C, 15 min, 3.) 0 deg C, 15 min; Yields of byproduct given;	A 77% B n/a
With titanium tetrachloride In dichloromethane 1.) -60 deg C, 15 min, 2.) from -60 deg C to 0 deg C, 15 min, 3.) 0 deg C, 15 min; Yields of byproduct given;	A n/a B 70%

di-n-butyloxymethane (2568-90-3) + 2-chloro-N-(2,6-dimethylphenyl)acetamide (1131-01-7) → N-(n-butoxymethyl)-N-chloroacetyl-2,6-dimethylaniline

Conditions	Yield
With toluene-4-sulfonic acid for 5h; Heating;	77%

di-n-butyloxymethane (2568-90-3) → 1-(Difluoro-nonafluorobutyloxy-methoxy)-1,1,2,2,3,3,4,4,4-nonafluoro-butane

Conditions	Yield
With 1,1,2-Trichloro-1,2,2-trifluoroethane; fluorine; sodium fluoride	75%
With fluorine; sodium fluoride In 1,1,2-Trichloro-1,2,2-trifluoroethane	75%

di-n-butyloxymethane (2568-90-3) + Acetanilid (103-84-4) → N-(n-butoxymethyl)acetanilide

Conditions	Yield
With toluene-4-sulfonic acid for 5h; Heating;	72%

di-n-butyloxymethane (2568-90-3) + 4-methoxyacetanilide (51-66-1) → N-butoxymethyl-N-(4-methoxy-phenyl)-acetamide

Conditions	Yield
With toluene-4-sulfonic acid for 5h; Heating;	71%

Upstream product

• 60-29-7 diethyl ether 
• 13483-18-6 1,2-bis(chloromethoxy)ethane 
• 2372-45-4 sodium butanolate 
• 89583-59-5 1,3-bis-chloromethoxy-butane 
• 2351-69-1 1-(chloromethoxy)butane 
• 71-36-3 butan-1-ol 
• 50-00-0 formaldehyd 
• 75-77-4 chloro-trimethyl-silane 
• 75-09-2 dichloromethane 
• 62609-70-5 bis-methanesulfonyloxymethyl ether 
• 544-16-1 n-Butyl nitrite 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 109-99-9 tetrahydrofuran 

Downstream Products

• 13093-19-1 N,N'-Methylen-di-ε-caprolactam 
• 109-87-5 Dimethoxymethane 
• 76050-97-0 1-butoxy-1-methoxymethane 
• 71-36-3 butan-1-ol 
• 6572-90-3 1,3-dioxocane 
• 1618-26-4 2,4-dithiapentane 
• 75-09-2 dichloromethane 
• 109-69-3 n-Butyl chloride 
• 592-84-7 n-butyl formate 
• 123-72-8 butyraldehyde 
• 2351-69-1 1-(chloromethoxy)butane 
• 75-65-0 tert-butyl alcohol 
• 85332-34-9 (1-Butoxymethyl-3-phenyl-propa-1,2-dienyl)-trimethyl-silane 
• 75425-77-3 (butoxymethyl)diphenylphosphine oxide 

Relevant articles and documents

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Utilization of Formic Acid as C1 Building Block for the Ruthenium-Catalyzed Synthesis of Formaldehyde Surrogates

Dialkoxymethanes are becoming increasingly important as fuel additives, formaldehyde surrogates, and chemical intermediates, but the effective synthesis remains challenging. Herein, the catalytic synthesis of dialkoxymethane products using a molecular catalyst is reported. The catalytic system, comprising the [Ru(triphos)(tmm)] in combination with the Lewis acid Al(OTf)3, enables the direct synthesis of dialkoxymethane products with formic acid as C1 building block in high to excellent turnover numbers.

Tailor-made Molecular Cobalt Catalyst System for the Selective Transformation of Carbon Dioxide to Dialkoxymethane Ethers

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Preparation method of dibutoxymethane

The invention discloses a preparation method of dibutoxymethane and relates to a preparation method of methane. The method comprises the process as follows: dimethoxymethane and n-butanol in a certain proportion are taken as raw materials, various liquid acids and supported liquid acids are taken as catalysts, the mixture is subjected to a reaction at the temperature of 0-160 DEG C and under the pressure of 0.1-10.0 MPa, and dibutoxymethane is generated in a high-selectivity manner; a heteropolyacid catalyst is prepared with an equivalent-volume impregnation method, and at least one of activated carbon, TiO2, Al2O3, SiO2, SBA-15 and MCM-41 is taken as a supporter; the supported heteropolyacid catalyst comprises heteropolyacid and a supporter for supporting the heteropolyacid, and heteropolyacid is one or more of phosphotungstic acid, silicotungstic acid, phosphomolybdic acid and silicomolybdic acid. A product prepared with the method is relatively single, the selectivity is high, required raw materials are cheap and easy to obtain, the whole process is simple to operate, no chemical substances polluting the environment are produced, and the preparation method belongs to an environment-friendly technological route.