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Formaldehyde di-n-butyl acetal, also known as dibutyl formal, is an organic compound that belongs to the acetal class. It is a colorless liquid with a characteristic odor and is used in various industrial applications due to its unique properties.

2568-90-3

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2568-90-3 Usage

Uses

Used in Chemical Synthesis:
Formaldehyde di-n-butyl acetal is used as a reactant for the preparation of butoxymethyltriphenylphosphonium iodide, which is utilized in carbon homologation and serves as a key intermediate in organic synthesis.
Used in Plastics Industry:
Formaldehyde di-n-butyl acetal is used as a halogen-free and less toxic solvent for solubilizing commercial low-density polyethylene (LDPE) samples. This allows for the analysis of molecular weight distribution using gel permeation chromatography (GPC).
Used in Fuel Industry:
Formaldehyde di-n-butyl acetal is used as a fuel additive to increase the octane number of gasoline or the n-cetane number of diesel fuels. Additionally, it helps in reducing smoke and particulate emissions, contributing to a cleaner and more efficient combustion process.
Used in Manufacturing of Synthetic Resins, Antiseptics, Deodorants, and Fungicides:
Formaldehyde di-n-butyl acetal is employed in the production of various chemical products, including synthetic resins, antiseptics, deodorants, and fungicides, due to its versatile properties and reactivity.

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

Check Digit Verification of cas no

The CAS Registry Mumber 2568-90-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,6 and 8 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2568-90:
(6*2)+(5*5)+(4*6)+(3*8)+(2*9)+(1*0)=103
103 % 10 = 3
So 2568-90-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H20O2/c1-3-5-7-10-9-11-8-6-4-2/h3-9H2,1-2H3

2568-90-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(butoxymethoxy)butane

1.2 Other means of identification

Product number -
Other names Butane, 1,1‘-[methylenebis(oxy)]bis-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2568-90-3 SDS

2568-90-3Synthetic route

formaldehyd
50-00-0

formaldehyd

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
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

n-Butyl nitrite

4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

4-bromo-N-nitroso-N-methylaniline
937-23-5

4-bromo-N-nitroso-N-methylaniline

Conditions
ConditionsYield
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

4-bromo-N,N-dimethylaniline

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

4-bromo-N-nitroso-N-methylaniline
937-23-5

4-bromo-N-nitroso-N-methylaniline

Conditions
ConditionsYield
With n-Butyl nitrite; water; ammonium chloride for 0.25h; Heating;A n/a
B 88%
Dimethoxymethane
109-87-5

Dimethoxymethane

butan-1-ol
71-36-3

butan-1-ol

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

methanol butoxymethoxymethane
89979-37-3

methanol butoxymethoxymethane

Conditions
ConditionsYield
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

4-methoxy-N,N-dimethylanilne

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

4-Methoxy-2-nitro-N,N-dimethylbenzeneamine
60049-83-4

4-Methoxy-2-nitro-N,N-dimethylbenzeneamine

C

4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine
130717-81-6

4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine

Conditions
ConditionsYield
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

1,1-dibromomethane

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
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

tert-butyl 3-bromodiazirine-3-carboxylate

sodium butanolate
2372-45-4

sodium butanolate

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

Dibutyl carbonate
542-52-9

Dibutyl carbonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide; butan-1-ol at 0 - 20℃; for 0.333333h;A 31%
B 82%
dichloromethane
75-09-2

dichloromethane

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
With sodium hydroxide; Tixogel VP for 72h; Heating;80%
With potassium hydroxide; methyl-tridecylammonium chloride Heating;
n-Butyl nitrite
544-16-1

n-Butyl nitrite

4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

A

formaldehyd
50-00-0

formaldehyd

B

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

C

Tributyl orthoformate
588-43-2

Tributyl orthoformate

D

2,4-dibromo-N,N-dimethylaniline
64230-27-9

2,4-dibromo-N,N-dimethylaniline

E

4-Bromo-N,N-di(n-butoxymethyl)benzeneamine
130717-78-1

4-Bromo-N,N-di(n-butoxymethyl)benzeneamine

F

4-bromo-N-nitroso-N-methylaniline
937-23-5

4-bromo-N-nitroso-N-methylaniline

Conditions
ConditionsYield
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

dimethyl sulfoxide

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
With bromine In tetrachloromethane for 4h; Ambient temperature; alcohol addition;78%
sodium butanolate
2372-45-4

sodium butanolate

butyl 3-bromo-3H-diazirine-3-carboxylate
792950-89-1

butyl 3-bromo-3H-diazirine-3-carboxylate

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

Dibutyl carbonate
542-52-9

Dibutyl carbonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide; butan-1-ol at 0 - 20℃; for 0.333333h;A 35%
B 75%
Dimethoxymethane
109-87-5

Dimethoxymethane

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
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

Dimethoxymethane

dibutyl acetal
871-22-7

dibutyl acetal

A

1,1-dimethoxyethane
534-15-6

1,1-dimethoxyethane

B

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

C

1-methoxy-1-butoxyethane
75677-94-0

1-methoxy-1-butoxyethane

D

methoxyisobutoxymethane
76050-98-1

methoxyisobutoxymethane

Conditions
ConditionsYield
With KU-2 resin at 40℃; for 5h;A 26%
B 9%
C 8%
D 31%
diethyl ether
60-29-7

diethyl ether

1,2-bis(chloromethoxy)ethane
13483-18-6

1,2-bis(chloromethoxy)ethane

sodium butanolate
2372-45-4

sodium butanolate

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

1,2-bis-butoxymethoxy-ethane
5703-97-9

1,2-bis-butoxymethoxy-ethane

C

bis-(2-butoxymethoxy-ethyl) ether
7736-68-7

bis-(2-butoxymethoxy-ethyl) ether

Conditions
ConditionsYield
weitere Reaktionen mit Natriumalkoholaten in den entsprechenden Alkoholen sowie in Aether;
1,2-bis-chloromethoxy-propane
16721-81-6

1,2-bis-chloromethoxy-propane

sodium butanolate
2372-45-4

sodium butanolate

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

1-butoxymethoxy-propan-2-ol
59569-56-1

1-butoxymethoxy-propan-2-ol

C

1,2-bis-butoxymethoxy-propane
59569-51-6

1,2-bis-butoxymethoxy-propane

Conditions
ConditionsYield
Reaktionen mit weiteren Natriumalkoholaten;
1,3-di(chloromethoxy)propane
138418-40-3

1,3-di(chloromethoxy)propane

sodium butanolate
2372-45-4

sodium butanolate

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

1,3-bis-butoxymethoxy-propane

1,3-bis-butoxymethoxy-propane

Conditions
ConditionsYield
With butan-1-ol
1,3-bis-chloromethoxy-butane
89583-59-5

1,3-bis-chloromethoxy-butane

sodium butanolate
2372-45-4

sodium butanolate

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

1,3-bis-butoxymethoxy-butane
92318-80-4

1,3-bis-butoxymethoxy-butane

Conditions
ConditionsYield
With butan-1-ol
1,4-bis(chloromethoxy)crotonylene
138649-02-2

1,4-bis(chloromethoxy)crotonylene

sodium butanolate
2372-45-4

sodium butanolate

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

1,4-bis-butoxymethoxy-but-2-yne

1,4-bis-butoxymethoxy-but-2-yne

Conditions
ConditionsYield
Reaktionen mit weiteren Natriumalkoholaten;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
With hydrogenchloride at 60 - 100℃;
1-(chloromethoxy)butane
2351-69-1

1-(chloromethoxy)butane

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

1,2-bis(chloromethoxy)ethane
13483-18-6

1,2-bis(chloromethoxy)ethane

sodium butanolate
2372-45-4

sodium butanolate

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

1-(chloromethoxy)butane
2351-69-1

1-(chloromethoxy)butane

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
With dimethyl sulfoxide In benzene
bis-methanesulfonyloxymethyl ether
62609-70-5

bis-methanesulfonyloxymethyl ether

butan-1-ol
71-36-3

butan-1-ol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
In acetonitrile
n-Butyl nitrite
544-16-1

n-Butyl nitrite

4-methoxy-N,N-dimethylanilne
701-56-4

4-methoxy-N,N-dimethylanilne

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

Tributyl orthoformate
588-43-2

Tributyl orthoformate

C

N-methyl-N-nitroso-p-anisidine
940-11-4

N-methyl-N-nitroso-p-anisidine

D

4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine
130717-81-6

4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine

Conditions
ConditionsYield
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

n-Butyl nitrite

4-methoxy-N,N-dimethylanilne
701-56-4

4-methoxy-N,N-dimethylanilne

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

4-Methoxy-2-nitro-N,N-dimethylbenzeneamine
60049-83-4

4-Methoxy-2-nitro-N,N-dimethylbenzeneamine

C

4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine
130717-81-6

4-Methoxy-2-nitro-N-methyl-N-nitrosobenzeneamine

Conditions
ConditionsYield
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

n-Butyl nitrite

4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

4-Bromo-N-(n-butoxymethyl)-N-methylbenzeneamine
130717-77-0

4-Bromo-N-(n-butoxymethyl)-N-methylbenzeneamine

C

4-bromo-N-nitroso-N-methylaniline
937-23-5

4-bromo-N-nitroso-N-methylaniline

Conditions
ConditionsYield
With ammonium chloride for 0.25h; Product distribution; Heating;A 4 % Chromat.
B 55 % Chromat.
C 20 % Chromat.
Dibutoxymethoxy-benzene
49758-73-8

Dibutoxymethoxy-benzene

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Conditions
ConditionsYield
With lithium aluminium tetrahydride; magnesium bromide In diethyl ether Ambient temperature;
formaldehyd
50-00-0

formaldehyd

1-ethoxymethyl-1H-imidazole
67319-04-4

1-ethoxymethyl-1H-imidazole

butan-1-ol
71-36-3

butan-1-ol

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

1-Butoxymethyl-3-ethoxymethyl-3H-imidazol-1-ium; chloride
118178-99-7

1-Butoxymethyl-3-ethoxymethyl-3H-imidazol-1-ium; chloride

Conditions
ConditionsYield
With hydrogenchloride 2.) 2 h, 90 deg C; Yield given. Multistep reaction;
formaldehyd
50-00-0

formaldehyd

butan-1-ol
71-36-3

butan-1-ol

A

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

B

1-(chloromethoxy)butane
2351-69-1

1-(chloromethoxy)butane

Conditions
ConditionsYield
With hydrogenchloride Title compound not separated from byproducts;
octanol
111-87-5

octanol

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

formaldehyde-(butyl-octyl-acetal)
84260-76-4

formaldehyde-(butyl-octyl-acetal)

Conditions
ConditionsYield
With Nafion-H SAC-13 silica nanocomposite Heating;100%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

2-phenylethanol
60-12-8

2-phenylethanol

formaldehyde-(butyl-phenethyl-acetal)
92101-62-7

formaldehyde-(butyl-phenethyl-acetal)

Conditions
ConditionsYield
With Nafion-H SAC-13 silica nanocomposite at 100℃;100%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

benzyl alcohol
100-51-6

benzyl alcohol

formaldehyde-(benzyl-butyl-acetal)
91764-40-8

formaldehyde-(benzyl-butyl-acetal)

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;99%
2,6-diethylaniline
579-66-8

2,6-diethylaniline

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

2,6-diethyl-N-(butoxymethyl)aniline

2,6-diethyl-N-(butoxymethyl)aniline

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 135 - 140℃; for 9h;96.2%
dimethylformamide [DMF]

dimethylformamide [DMF]

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

tralopyril
122454-29-9

tralopyril

4-Bromo-1-(n-butoxymethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

4-Bromo-1-(n-butoxymethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In water94.6%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

rac-octan-2-ol
4128-31-8

rac-octan-2-ol

2-butoxymethoxy-octane

2-butoxymethoxy-octane

Conditions
ConditionsYield
With Nafion-H SAC-13 silica nanocomposite In benzene Heating;88%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Dichlorophenylphosphine
644-97-3

Dichlorophenylphosphine

(butoxymethyl)phenylphosphinic acid
75425-74-0

(butoxymethyl)phenylphosphinic acid

Conditions
ConditionsYield
With zinc(II) chloride at 110℃; for 4h;87.7%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

cyclohexanol
108-93-0

cyclohexanol

Cyclohexyl--ether
91243-24-2

Cyclohexyl--ether

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;86%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

chlorodiphenylphosphonium tetrachloroaluminate

chlorodiphenylphosphonium tetrachloroaluminate

(butoxymethyl)diphenylphosphine oxide
75425-77-3

(butoxymethyl)diphenylphosphine oxide

Conditions
ConditionsYield
In diethyl ether for 1.5h; Heating;85%
dibutyl chlorophosphite
4124-92-9

dibutyl chlorophosphite

di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

O,O-dibutyl(butoxymethyl)phosphonate
59375-49-4

O,O-dibutyl(butoxymethyl)phosphonate

Conditions
ConditionsYield
With zinc(II) chloride at 80℃; for 7h;84.5%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

A

(1-butoxyethyl)benzene
4157-77-1

(1-butoxyethyl)benzene

B

1-Phenethyl-methoxy-butylether
92423-62-6

1-Phenethyl-methoxy-butylether

Conditions
ConditionsYield
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

di-n-butyloxymethane

butyl glycolate
7397-62-8

butyl glycolate

A

Butoxymethoxy-acetic acid butyl ester

Butoxymethoxy-acetic acid butyl ester

B

Butoxycarbonylmethoxymethoxy-acetic acid butyl ester

Butoxycarbonylmethoxymethoxy-acetic acid butyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 130 - 150℃; for 5h;A 83%
B 7%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

cholesterol
57-88-5

cholesterol

(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

(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
ConditionsYield
With Nafion-H SAC-13 silica nanocomposite In benzene Heating;83%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

3-chloro-2-hydroxy-propionic acid butyl ester
60593-60-4

3-chloro-2-hydroxy-propionic acid butyl ester

2-Butoxymethoxy-3-chloro-propionic acid butyl ester

2-Butoxymethoxy-3-chloro-propionic acid butyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 130 - 150℃; for 5h;78%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

1,4-bis(trimethylsilyl)-2-butyne
21752-78-3

1,4-bis(trimethylsilyl)-2-butyne

A

(2-Butoxymethyl-buta-2,3-dienyl)-trimethyl-silane
80404-94-0

(2-Butoxymethyl-buta-2,3-dienyl)-trimethyl-silane

B

2,3-Bis-butoxymethyl-buta-1,3-diene
80405-01-2

2,3-Bis-butoxymethyl-buta-1,3-diene

Conditions
ConditionsYield
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

di-n-butyloxymethane

2-chloro-N-(2,6-dimethylphenyl)acetamide
1131-01-7

2-chloro-N-(2,6-dimethylphenyl)acetamide

N-(n-butoxymethyl)-N-chloroacetyl-2,6-dimethylaniline

N-(n-butoxymethyl)-N-chloroacetyl-2,6-dimethylaniline

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 5h; Heating;77%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

1-(Difluoro-nonafluorobutyloxy-methoxy)-1,1,2,2,3,3,4,4,4-nonafluoro-butane

1-(Difluoro-nonafluorobutyloxy-methoxy)-1,1,2,2,3,3,4,4,4-nonafluoro-butane

Conditions
ConditionsYield
With 1,1,2-Trichloro-1,2,2-trifluoroethane; fluorine; sodium fluoride75%
With fluorine; sodium fluoride In 1,1,2-Trichloro-1,2,2-trifluoroethane75%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

Acetanilid
103-84-4

Acetanilid

N-(n-butoxymethyl)acetanilide

N-(n-butoxymethyl)acetanilide

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 5h; Heating;72%
di-n-butyloxymethane
2568-90-3

di-n-butyloxymethane

4-methoxyacetanilide
51-66-1

4-methoxyacetanilide

N-butoxymethyl-N-(4-methoxy-phenyl)-acetamide

N-butoxymethyl-N-(4-methoxy-phenyl)-acetamide

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

2568-90-3Relevant academic research and scientific papers

An efficient and convenient method for the synthesis of dialkoxymethanes using kaolinite as a catalyst

Pathak, Devendra D.,Gerald, J. Joe

, p. 1557 - 1561 (2003)

A one pot synthesis of dialkoxymethanes (2a-h) is described from the reaction of alcohols (1a-h) with paraformaldehyde under reflux in the presence of catalytic amount of kaolinite.

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

Beydoun, Kassem,Thenert, Katharina,Wiesenthal, Jan,Hoppe, Corinna,Klankermayer, Jürgen

, p. 1944 - 1947 (2020/04/08)

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.

Novel synthesis method of alkoxymethylamine compound

-

Paragraph 0047; 0048, (2019/10/01)

The invention relates to a novel synthesis method of an alkoxymethylamine compound. The novel synthesis method comprises the steps: (1) dehydrating formaldehyde HCHO and alcohol R1OH by carrying out an aldolization under the action of an acid catalyst to obtain dialkoxymethane; and (2) carrying out a hydrocarbylation reaction on dialkoxymethane obtained in step (1) and substituted amine R2-NH2 toremove alcohol to obtain an alkoxymethyl substituent amine compound N-R1 oxymethyl-N-R2 amine. The synthesis method disclosed by the invention is simple in operation and high in yield reaching 92% orabove; and compared with the prior art, the novel synthesis method has the advantages that no acid wastewater, waste salts and chloromethyl alkyl ether serving as a cancerogen are greatly generated, the environment protection cost is favorably reduced, and the industrial prospect is higher.

Br?nsted-acidic ionic liquids as efficient catalysts for the synthesis of polyoxymethylene dialkyl ethers

Song, Heyuan,Kang, Meirong,Jin, Fuxiang,Wang, Guoqin,Li, Zhen,Chen, Jing

, p. 853 - 861 (2017/05/24)

Acetalation of formaldehyde (HCHO) with dialkyl formal or aliphatic alcohol to prepare polyoxymethylene dialkyl ethers (RO(CH2O)nR, n ≥ 1) catalyzed by Br?nsted-acidic ionic liquids has been developed. The correlation between the structure and acidity activity of various ionic liquids was studied. Among the ionic liquids investigated, 1-(4-sulfonic acid)butyl-3-methylimidazolium hydrogen sulfate ([MIMBs]HSO4) exhibited the best catalytic performance in the reaction of diethoxymethane (DEM1) with trioxane. The influences of ionic liquid loading, molar ratio of DEM1 to HCHO, reaction temperature, pressure, time, and reactant source on the catalytic reaction were explored using [MIMBs]HSO4 as the catalyst. Under the optimal conditions of n([MIMBs]HSO4):n(DEM1):n(HCHO) = 1:80:80, 140 °C, and 4 h, the conversion of HCHO and selectivity for DEM2–8 were 92.6% and 95.1%, respectively. The [MIMBs]HSO4 catalyst could be easily separated and reused. A feasible mechanism for the catalytic performance of [MIMBs]HSO4 was proposed.

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

Schieweck, Benjamin G.,Klankermayer, Jürgen

supporting information, p. 10854 - 10857 (2017/08/30)

Herein a non-precious transition-metal catalyst system for the selective synthesis of dialkoxymethane ethers from carbon dioxide and molecular hydrogen is presented. The development of a tailored catalyst system based on cobalt salts in combination with selected Triphos ligands and acidic co-catalysts enabled a synthetic pathway, avoiding the oxidation of methanol to attain the formaldehyde level of the central CH2 unit. This unprecedented productivity based on the molecular cobalt catalyst is the first example of a non-precious transition-metal system for this transformation utilizing renewable carbon dioxide sources.

Preparation method of dibutoxymethane

-

Paragraph 0035; 0036, (2016/10/10)

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.

Method for synthesizing butoxy methoxymethane

-

Paragraph 0031; 0032, (2017/04/03)

The invention provides a method for synthesizing methane, in particular to a method for synthesizing butoxy methoxymethane. A brand-new synthesis path for butyl cellosolve and the preparation method for butoxy methoxymethane are developed. The path is characterized in that butoxy methoxymethane is synthesized by methylal and butanol at high selectivity; butoxy methoxymethane is subjected to directional carbonylation, and butoxy methyl acetate is generated; butoxy methyl acetate is hydrogenated to generate butyl cellosolve and methyl alcohol. The preparation method includes the steps that dimethoxymethane and n-butyl alcohol at a certain ratio serve as raw materials, at certain temperature and pressure, molecular sieves of different topological structures serve as catalysts, and butoxy methoxymethane is prepared at high selectivity. The raw materials needed for the method are cheap and easy to get, the whole process is simple in operation, and the product is single, high in selectivity and suitable for industrial production, and has good application prospects.

Method for preparing dibutoxymethane from dimethoxymethane and n-butyl alcohol

-

Paragraph 0026, (2017/04/03)

The invention provides a method for preparing dibutoxymethane from dimethoxymethane and n-butyl alcohol and relates to a method for preparing dibutoxymethane. The method comprises steps as follows: dimethoxymethane and n-butyl alcohol which serve as raw materials are subjected to a reaction in the presence of catalysts, namely, liquid acid and supported liquid acid, at the reaction temperature of 0-160 DEG C under the reaction pressure of 0.1-10.0 MPa, and dibutoxymethane is produced in a high-selective manner; a resin catalyst is one or more of KAD302, KC107, NKC-9, DA-330, D009B, Amberlyst-15, D072H and the like which contain sulfonic acid functional groups; the reaction temperature is 0-160 DEG C and the reaction pressure is 0.1-10.0 MPa. According to the method, a single product is produced, the selectivity is high, required raw materials are low in price and easy to obtain, the operation is simple in the whole procedure, no chemical substances polluting the environment are produced, and the method is an environment-friendly technological process.

Method for preparing dibutoxymethane

-

Paragraph 0034-0035, (2017/07/05)

The invention discloses a method for preparing dibutoxymethane, and relates to a method for preparing methane. The method comprises the following processes: dimethoxymethane and n-butanol are adopted as raw materials, and molecular sieves adopting different topological structures are adopted as catalysts for preparing dibutoxymethane at a temperature under the pressure; the atomic ratio of silicon to aluminum in the catalysts, namely, the molecular sieves adopting the different topological structures is as follows: Si/Al=3-100; the molecular sieves adopting the different topological structures are one or more of an H-type MCM-22 molecular sieve, an H-type ZSM-35 molecular sieve, an H-type ZSM-5 molecular sieve, H-mordenite, H-zeolite Y and an H-type Beta molecular sieve; structure types of the catalysts, namely, the molecular sieves adopting the different topological structures are selected from at least one of MWW, FER, MFI, MOR, FAU and BEA. According to the method, relatively single products are produced, the selectivity is high, required raw materials are cheap and easy to obtain, and the whole process is easy to operate; meanwhile, no chemical substances polluting the environment are produced, and the method belongs to an environment-friendly technological path.

Ruthenium-Catalyzed Synthesis of Dialkoxymethane Ethers Utilizing Carbon Dioxide and Molecular Hydrogen

Thenert, Katharina,Beydoun, Kassem,Wiesenthal, Jan,Leitner, Walter,Klankermayer, Jürgen

supporting information, p. 12266 - 12269 (2016/10/13)

The synthesis of dimethoxymethane (DMM) by a multistep reaction of methanol with carbon dioxide and molecular hydrogen is reported. Using the molecular catalyst [Ru(triphos)(tmm)] in combination with the Lewis acid Al(OTf)3resulted in a versatile catalytic system for the synthesis of various dialkoxymethane ethers. This new catalytic reaction provides the first synthetic example for the selective conversion of carbon dioxide and hydrogen into a formaldehyde oxidation level, thus opening access to new molecular structures using this important C1source.

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