3658-95-5

Basic information

• Product Name: 1,1-Diethoxybutane
• Synonyms: Butylaldehyde diethyl acetal;n-Butyraldehyde diethyl acetal;BUTYRALDEHYDE DIETHYL ACETAL;1,1-DIETHOXYBUTANE;BUTRALDEHYDE DIETHYL ACETAL;Butane, 1,1-diethoxy-;butyraldehyde ethyl acetal;BUTYRALDEHYDE DIETHYLACETAL, 97+%
• CAS NO: 3658-95-5
• Molecular Formula: C₈H₁₈O₂
• Molecular Weight: 146.23
• EINECS: 222-913-5
• Mol File: 3658-95-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 143°C/760mmHg
• Flash Point: 30 °C
• Appearance: Clear colorless/Liquid
• Density: 0.829 g/mL at 20 °C
• Vapor Pressure: 6.83mmHg at 25°C
• Refractive Index: n20/D1.396
• Storage Temp.: Flammables area
• BRN: 1697910
• CAS DataBase Reference: 1,1-Diethoxybutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Diethoxybutane(3658-95-5)
• EPA Substance Registry System: 1,1-Diethoxybutane(3658-95-5)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/38
• Safety Statements: 26-37/39-16
• RIDADR: UN 1993C 3 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 3658-95-5(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Preparation

To a three-necked flask equipped with an air-tight mechanical stirrer, dropping funnel, reflux condenser, and drying tube, are added 3.0 gm (1.25 gm-atom) magnesium turnings, 50 ml of dry ether, and a small crystal of iodine. Then 5 gm of rt-butyl bromide is added dropwise until 171.0 gm (1.25 mole) has been added. The reaction takes about ? - l h r if the reaction mixture is cooled. The solution is refluxed for ? hr, cooled to 50°C, and then 148 gm (1.0 mole) of triethyl orthoformate is added dropwise over a ?-hr period. The reaction mixture is refluxed for 16 hr, crushed ice added to decompose the excess Grignard reagent, the ether separated and washed with water. The water layer is added to a separatory funnel containing 200 ml of ether, treated with acetic acid to pH 7.0, shaken, and the ether separated. The latter ether layer is washed with 10% aqueous sodium carbonate, water, and dried. The latter water layer is extracted twice again with ether (200 ml). The combined ether layers are dried over potassium carbonate and fractionated to afford 128 gm (80%), b.p. 143°-144°.

InChI:InChI=1/C8H18O2/c1-4-7-8(9-5-2)10-6-3/h8H,4-7H2,1-3H3

Upstream product

• 78-10-4 tetraethoxy orthosilicate 
• 123-72-8 butyraldehyde 
• 623-81-4 diethyl sulphite 
• 64-17-5 ethanol 
• 927-77-5 n-propylmagnesium bromide 
• 122-51-0 orthoformic acid triethyl ester 
• 123-73-9 crotonaldehyde 
• 75-07-0 acetaldehyde 
• 998-30-1 Triethoxysilane 
• 6728-26-3 (E)-2-Hexenal 
• 10602-36-5 3-butenal 1,1-diethylacetal 
• 24964-76-9 triethyl orthobutyrate 

Downstream Products

• 100385-61-3 ethyl-(3-ethyl-1-propyl-pent-3-enyl)-ether 
• 78-40-0 triethyl phosphate 
• 3658-92-2 butyraldehyde-(ethyl-pentyl-acetal) 
• 34557-54-5 methane 
• 74-84-0 ethane 
• 75-65-0 tert-butyl alcohol 
• 106-97-8 n-butane 
• 929-05-5 1-ethoxybut-1-ene 
• 628-81-9 butyl ethyl ether 
• 101-33-7 1,1,3-triethoxy-hexane 
• 30989-75-4 ethoxy-1 formyl-2 butene-1 
• 4461-87-4 1,1-dimethoxybutane 
• 64-17-5 ethanol 
• 127248-85-5 1-ethoxy-1-methoxy-butane 

Relevant articles and documents

Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals

A versatile protocol for the production of acetals/thioacetals by means of direct electrochemical oxidation is developed here under neutral conditions, providing (thio)acetals with good functional group tolerance and a wide scope for both aldehydes and (thio)alcohols. DFT calculations reveal that direct electron transfer from the anode plays a key role in carbonyl activation during this acid free acetalization process.

Antimony(v) catalyzed acetalisation of aldehydes: An efficient, solvent-free, and recyclable process

A highly selective, solvent-free process for the acetalisation of aldehydes was achieved by the use of a readily accessible antimony(v) catalyst which we previously prepared in our lab as a tetraarylstibonium triflate salt ([1][OTf]). High yields of the acetals were achieved in the presence of stoichimetric amounts of either triethoxymethane or triethoxysilane. It was found that triethoxymethane reactions required longer time to reach completion when compared to triethoxysilane reactions which were completed upon mixing of the reagents. The products can be easily separated from the catalyst by distillation which enabled further use of [1][OTf] in additional calytic reactions (up to 6 cycles). Moreover, [1]+ also catalyzed the deprotection of the acetals into their corresponding aldehydes using only water as a solvent.

Synthesis of biodiesel without formation of free glycerol

A new approach to the synthesis of biodiesel has been developed on the basis of alcoholysis of a triglyceride in combination with acetalization of glycerol with lower carbonyl compounds or acetals derived therefrom. A model synthesis of biodiesel not involving free glycerol has been accomplished using rapeseed oil and acid catalysts, as well as without a catalyst under generation of ethanol supercritical fluid; in the latter case, monoalkyl glycerol ethers are formed in addition to the expected cyclic ketals.