19255-82-4

Usage

Physical state

Colorless liquid

Molecular weight

188.26 g/mol

Uses

a. Solvent in coatings, paints, and adhesives
b. Intermediate in the manufacture of other chemicals
c. Production of specialty chemicals and pharmaceuticals

Solubility

Able to dissolve a wide range of substances

Toxicity

Low toxicity, but should be handled with care and in accordance with safety guidelines

InChI:InChI=1/C11H22O3/c1-4-6-8-13-11(10(3)12)14-9-7-5-2/h11H,4-9H2,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 78-98-8 2-oxopropanal 
• 71-36-3 butan-1-ol 
• 624-67-9 Propargylic aldehyde 
• 544-16-1 n-Butyl nitrite 
• 67-64-1 acetone 
• 2648-49-9 2-ethoxyprop-2-enal 
• 63234-15-1 2-butylsulfanylpropenal 
• 56-82-6 Glyceraldehyde 
• 96-26-4 dihydroxyacetone 

Downstream Products

• 13040-58-9 7-methylpterin 
• 708-75-8 2-amino-6-methylpteridin-4(1H)-one 
• 24201-52-3 4-methyl-5-butoxy1,3-oxazole 

Relevant academic research and scientific papers

Reactions of 2-butylsulfanyl-2-alkenals with alcohols and water

2-Butylsulfanyl-2-alkenals react with alcohols at room temperature in the presence of acid catalysts to give 45-90% of the corresponding acetals. Acetals derived from 2-butylsulfanylpropenal readily undergo hydrolysis at the vinylsulfanyl group (20°C, catalysis by HCl or TsOH) with formation of 2-oxopropionaldehyde O,O- or O,S-acetals in 70-90% yield. Unlike 2-butylsulfanyl-2-propenal O,O-dialkyl acetals, the initial aldehydes and 2,4-dinitrophenylhydrazones derived therefrom are stable to hydrolysis under analogous conditions: the vinyl sulfide moiety remains unchanged even under considerably more severe conditions (100°C, 3 h; HCl, H2SO 4, CF3SO2OH, or TiCl4).

Preparation method of pyruvic aldehyde glycol

The invention relates to a method for preparing pyruvic aldehyde glycol, which comprises the following step of: reacting 1, 3-dihydroxy acetone with alcohol in the presence of a catalyst to obtain the pyruvic aldehyde glycol.

Zeolite-catalysed conversion of C3 sugars to alkyl lactates

The direct conversion of C3 sugars (or trioses) to alkyl lactates was achieved using zeolite catalysts. This reaction represents a key step towards the efficient conversion of bio-glycerol or formaldehyde to added-value chemicals such as lactate derivatives. The highest yields and selectivities towards the desired lactate product were obtained with Ultrastable zeolite Y materials having a low Si/Al ratio and a high content of extra-framework aluminium. Correlating the types and amounts of acid sites present in the different zeolites reveals that two acid functions are required to achieve excellent catalysis. Bronsted acid sites catalyse the conversion of trioses to the reaction intermediate pyruvic aldehyde, while Lewis acid sites further assist in the intramolecular rearrangement of the aldehyde into the desired lactate ester product. The presence of strong zeolitic Bronsted acid sites should be avoided as much as possible, since they convert the intermediate pyruvic aldehyde into alkyl acetals instead of lactate esters. A tentative mechanism for the acid catalysis is proposed based on reference reactions and isotopically labelled experiments. Reusability of the USY catalyst is demonstrated for the title reaction.

Tin-catalyzed conversion of trioses to alkyl lactates in alcohol solution

Tin chlorides, SnCl2 and SnCl4·5H2O are excellent catalysts for the reactions of trioses, dihydroxyacetone and glyceraldehyde with alcohols (MeOH, EtOH and nBuOH) to give alkyl lactates, whose reaction mechanism involves the intermediary formation of pyruvic aldehyde followed by its esterification, which is distinctively promoted by tin halides. The Royal Society of Chemistry 2005.

Reactions of alcohols with α-alkoxyacroleins at room temperature

The first stage of the reactions of alcohols with α-alkoxyacroleins in an acidic medium at 20°C under kinetically controlled conditions is the Markovnikoff addition at the C=C bond to form 2,2-dialkoxypropanals (methylglyoxal ketals). Under conditions of thermodynamic control, subsequent acetalization of the aldehyde group occurs to form 1,1,2,2-tetraalkoxypropanes. When the duration of the reaction is further increased in the absence of a water acceptor, the ketal group undergoes hydrolysis and methylglyoxal acetals are formed. A method was developed for the preparation of methylglyoxal ketals.

Process for synthesizing methyl glyoxal acetals

A one-step process for the synthesis of methyl glyoxal acetals from dihydroxyacetone wherein dihydroxyacetone, an alkanol and an acid catalyst are reacted to produce the acetals.