Paul T. Bially

The Chemistry of

Alkyl Polyglucoside Esters

Organic Chemistry of Esters

Carboxylic acid derivatives in which hydroxyl group

(-OH) is replaced by an alkoxy group (-OR)

R—C—OH + R’—OH R—C—O—R’ + H2O

Esterification:OO

ACID ALCOHOL ESTER

Synthesis of Alkyl Polyglucosides

OO

OOHH

OOHHOOHH

OOHHOOHH HHOO

OOOOHH

OOHHOOHH

OOOOHH

OOHHOOHH

OOHH

OO

OO

-- HH22OO

HH++

nn

nnmm

++

GLUCOSE FATTY

ALCOHOL

ALKYL

POLYGLUCOSIDE

1) Maleic Anhydride

2) Sodium Sulfite

1) Citric Acid

2) Sodium Hydroxide

1) Tartaric Acid

2) Sodium Hydroxide

AlkylpolyglucosideAlkylpolyglucoside

SulfosuccinateSulfosuccinate

OOHH

++

OOOOHH

OOHHOOHH

OOOOHH

OOHHOOHH

OO

OO

nnmm

Alkylpolyglucoside

Synthesis of Alkyl Polyglucoside Esters (AGEs)

AlkylpolyglucosideAlkylpolyglucoside

CitrateCitrate

AlkylpolyglucosideAlkylpolyglucoside

TartrateTartrate

AGEs Retain Favorable APG Properties…

Derived from

natural, renewable

raw materials

Strong biological

performance as

built-in and tank

mix adjuvants

Biodegradable,

not harmful to

the environment

Free from dioxane,

ethylene oxide, and

nitrosamine

precursors

Mild to skin and

non-irritating to

the eyes

AGEs Are Highly Effective Soil Penetrants

WDPT (s)

Treatment 8000mgL-1 2000mgL-1 1000mgL-1 500mgL-1

Citrate Ester 2.0 52.6 68.0 155.0

Tartrate Ester 2.0 61.4 83.3 180.0

Sulfosuccinate Ester 2.8 65.2 100.7 135.0

L61 4.2 110.6 128.3 325.9

31R1 5.5 121.0 284.2 471.8

L62 8.0 152.7 167.9 468.4

25R2 9.8 203.3 394.4 >600

L64 8.0 511.4 >600 >600

APG (C8-10) 3.0 >600 >600 >600

APG (C9-11) 3.0 >600 >600 >600

Top 3 performers in GREEN

Patent pending