The document discusses alkyl polyglucoside esters (AGEs), which are synthesized from alkyl polyglucosides and various acids. Three types of AGEs are synthesized - those using maleic anhydride, citric acid, and tartaric acid. AGEs retain the favorable properties of being biodegradable, non-toxic, and mild to skin and eyes. Testing showed that AGEs, particularly citrate and tartrate esters, were highly effective soil penetrants and performed better than alkyl polyglucosides and other reference substances.

1. The Chemistry of
Alkyl Polyglucoside Esters
Paul T. Bially

2. Organic Chemistry of Esters
Esterification:
O O
R—C—OH + R’—OH R—C—O—R’ + H2O
ACID ALCOHOL ESTER
Carboxylic acid derivatives in which hydroxyl group
(-OH) is replaced by an alkoxy group (-OR)

3. Synthesis of Alkyl Polyglucosides
OH
O
OH
OH OH HO H+
OH +
n -H O
2
GLUCOSE FATTY
OH ALCOHOL
O
OH
OH O
OH
O
OH
OH O
OH
n
m
ALKYL
POLYGLUCOSIDE

4. Synthesis of Alkyl Polyglucoside Esters (AGEs)
OH
O
OH
OH O
OH
O
OH
OH O
OH
n
m
Alkylpolyglucoside
+
1) Maleic Anhydride 1) Citric Acid 1) Tartaric Acid
2) Sodium Sulfite 2) Sodium Hydroxide 2) Sodium Hydroxide
Alkylpolyglucoside Alkylpolyglucoside Alkylpolyglucoside
Sulfosuccinate Citrate Tartrate

5. AGEs Retain Favorable APG
Properties…
Free from dioxane,
Derived from Biodegradable, ethylene oxide, and
natural, renewable not harmful to nitrosamine
raw materials the environment precursors
Strong biological
Mild to skin and performance as
non-irritating to built-in and tank
the eyes mix adjuvants

6. 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