Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid: dual activated 1,2-hydride shift mechanism by protonated Al(OH)3 species

2009 ◽  
pp. 2688 ◽  
Author(s):  
Takashi Ohshima ◽  
Yoshihiro Yamamoto ◽  
Usaji Takaki ◽  
Yoshihisa Inoue ◽  
Takuya Saeki ◽  
...  
Keyword(s):  
Glycolic Acid ◽  
Theoretical Study ◽  
Hydride Shift

Experimental and Theoretical Study on Glycolic Acid Provided Fast Bio/Seawater-Degradable Poly(Butylene Succinate-co-Glycolate)

2021 ◽  
Vol 9 (10) ◽  
pp. 3850-3859
Author(s):  
Han Hu ◽  
Jiayi Li ◽  
Ying Tian ◽  
Chao Chen ◽  
Fenglong Li ◽  
...  
Keyword(s):  
Glycolic Acid ◽  
Theoretical Study ◽  
Butylene Succinate

ChemInform Abstract: A THEORETICAL STUDY OF VARIOUS ROTAMERS OF GLYCOLIC ACID

1982 ◽  
Vol 13 (7) ◽  
Author(s):  
T.-K. HA ◽  
C. E. BLOM ◽  
HS. H. GUENTHARD
Keyword(s):  
Glycolic Acid ◽  
Theoretical Study

A theoretical study of various rotamers of glycolic acid

1981 ◽  
Vol 85 (3-4) ◽  
pp. 285-292 ◽  
Author(s):  
Tae-Kyu Ha ◽  
C.E. Blom ◽  
H.S.H. Günthard
Keyword(s):  
Glycolic Acid ◽  
Theoretical Study

Reactions between Glycolic Acid and Cu+in the Gas Phase. An Experimental and Theoretical Study

2002 ◽  
Vol 106 (40) ◽  
pp. 9359-9368 ◽  
Author(s):  
Laurence Boutreau ◽  
Pierre Toulhoat ◽  
Jeanine Tortajada ◽  
Alberto Luna ◽  
Otilia Mó ◽  
...  
Keyword(s):  
Gas Phase ◽  
Glycolic Acid ◽  
Theoretical Study

scholarly journals Tandem catalysis for the production of alkyl lactates from ketohexoses at moderate temperatures

2015 ◽  
Vol 112 (38) ◽  
pp. 11777-11782 ◽  
Author(s):  
Marat Orazov ◽  
Mark E. Davis
Keyword(s):  
Lactic Acid ◽  
High Temperature ◽  
Molecular Sieves ◽  
Glycolic Acid ◽  
Catalyst Deactivation ◽  
Aldol Reactions ◽  
Tandem Catalysis ◽  
Alkyl Esters ◽  
Hydride Shift ◽  
Lactate Formation

Retro-aldol reactions have been implicated as the limiting steps in catalytic routes to convert biomass-derived hexoses and pentoses into valuable C2, C3, and C4 products such as glycolic acid, lactic acid, 2-hydroxy-3-butenoic acid, 2,4-dihydroxybutanoic acid, and alkyl esters thereof. Due to a lack of efficient retro-aldol catalysts, most previous investigations of catalytic pathways involving these reactions were conducted at high temperatures (≥160 °C). Here, we report moderate-temperature (around 100 °C) retro-aldol reactions of various hexoses in aqueous and alcoholic media with catalysts traditionally known for their capacity to catalyze 1,2-intramolecular carbon shift (1,2-CS) reactions of aldoses, i.e., various molybdenum oxide and molybdate species, nickel(II) diamine complexes, alkali-exchanged stannosilicate molecular sieves, and amorphous TiO2–SiO2 coprecipitates. Solid Lewis acid cocatalysts that are known to catalyze 1,2-intramolecular hydride shift (1,2-HS) reactions that enable the formation of α-hydroxy carboxylic acids from tetroses, trioses, and glycolaldehyde, but cannot readily catalyze retro-aldol reactions of hexoses and pentoses at these moderate temperatures, are shown to be compatible with the aforementioned retro-aldol catalysts. The combination of a distinct retro-aldol catalyst with a 1,2-HS catalyst enables lactic acid and alkyl lactate formation from ketohexoses at moderate temperatures (around 100 °C), with yields comparable to best-reported chemocatalytic examples at high temperature conditions (≥160 °C). The use of moderate temperatures enables numerous desirable features such as lower pressure and significantly less catalyst deactivation.

Sign in / Sign up

Export Citation Format

Share Document