18449-60-0

Basic information

• Product Name: D,L-sec-butyl D,L-lactate
• Synonyms: 2-butyl lactate; 2-Butyl 2-hydroxypropionate; AI3-33998; Secbutyl lactate; D,L-sec-Butyl D,L-lactate; Propanoic acid, 2-hydroxy-, 1-methylpropyl ester; butan-2-yl 2-hydroxypropanoate
• CAS NO: 18449-60-0
• Molecular Formula: C₇H₁₄O₃
• Molecular Weight: 146.1843
• EINECS: 242-334-1
• Mol File: 18449-60-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 181.6°C at 760 mmHg
• Flash Point: 65.6°C
• Density: 1.002g/cm³
• Vapor Pressure: 0.247mmHg at 25°C
• Refractive Index: 1.43
• CAS DataBase Reference: D,L-sec-butyl D,L-lactate(CAS DataBase Reference)
• NIST Chemistry Reference: D,L-sec-butyl D,L-lactate(18449-60-0)
• EPA Substance Registry System: D,L-sec-butyl D,L-lactate(18449-60-0)

Safety Data

• Hazardous Substances Data: 18449-60-0(Hazardous Substances Data)

Usage

General Description

D,L-sec-Butyl D,L-lactate is a chemical compound that belongs to the class of lactate esters. It is a clear, colorless liquid with a slight fruity odor, and it is often used as a solvent or chemical intermediate in various industries. D,L-sec-Butyl D,L-lactate is synthesized through the esterification of lactic acid with sec-butanol. D,L-sec-Butyl D,L-lactate is commonly used in the production of polymers, resins, coatings, and inks. It also has applications in the formulation of personal care and cosmetic products, as well as in the manufacturing of flavors and fragrances. Additionally, it is considered to be biodegradable and is often used as an environmentally friendly alternative to other solvents.

Upstream product

• 849585-22-4 LACTIC ACID 
• 78-92-2 iso-butanol 
• 547-64-8 methyl lactate 
• 4221-99-2 (S)-2-butanol 
• 7699-00-5 (R)-Ethyl lactate 
• 687-47-8 (S)-Ethyl lactate 

Downstream Products

• 5349-70-2 2-lauroyloxy-propionic acid sec-butyl ester 
• 5401-64-9 diethylene glycol-O.O-dicarboxylic acid bis-(1-carbo-sec-butyloxy-ethyl ester) 

Relevant articles and documents

Lipase-catalyzed oligomerization and hydrolysis of alkyl lactates: Direct evidence in the catalysis mechanism that enantioselection is governed by a deacylation step

Lipase-catalyzed oligomerization of alkyl d-and l-lactate monomers (RDLa and RLLa, respectively) was studied for the first time. It has been found that the oligomerization occurs enantioselectively only for d-lactates to give oligomers up to heptamers of lactic acid (LA) in good to high yields by using primary C1 to C8 alkyl groups and sec-butyl group for d-lactate monomers. No reaction happened for all l-lactates in similar conditions. Lipase-catalyzed hydrolysis of alkyl d-and l-lactates was also examined, revealing that the hydrolysis took place for both d-and l-lactates, although l-lactates proceeded a couple of times slower. The hydrolysis results clearly demonstrate that the lipase catalysis mechanism involves an acyl-enzyme intermediate (EM) formation via the acylation step from both d-and l-lactates as a rate-determining step, and the subsequent deacylation step, a nucleophilic attack of water to the EM, takes place to produce free LA. On the other hand, in the oligomerization of d-lactates, the deacylation step, in which a sec-alcohol group of the monomer or of the propagating chain-end attacks to the EM, is only allowed for the sec-d-alcohol group to give a one-LA-unit-elongated oligomer. l-Lactates form the EM; however, the subsequent deacylation reaction with both the sec-l-and sec-d-alcohol groups does not take place, failing in the oligomerization to occur. These results provide with the first direct evidence in the lipase catalysis that the enantioselection is governed by the deacylation step. In the co-oligomerization between l-and d-lactates, the l-isomer retarded the reaction rate of the d-isomer, which was found due to the function of the former as a competitive inhibitor in the acylation step toward the latter.