ALKYL POLYGLYCOSIDE

PRASHANT SONI
12 OIL 1005

Introduction

Alkyl polyglycosides are non ionic

surfactants

These are basically acetal products

from the reaction of alcohols and
saccharides (which contain a
aldehyde functionality) .

They have superior chemical

properties than other non-ionic
surfactants due to their chemical
structure (strong hydrophilic part:
glucose residue, strong
hydrophobic part: fatty alcohol
residue).

Chemistry of reaction

In synthesis of polyglycosides, a polyfunctional sugar component is

combined with a nucleophile such as an alcohol, carbohydrate etc.

The reaction involves an Sn2 substitution at anomeric carbon stereo

selectively with inversion of configuration.

Raw materials

1) fatty alcohols

Fatty alcohol blends are used to build up the hydrophobic part of the
molecule.

Fatty alcohols can be derived either from the petrochemical (synthetic

sources) or renewable sources (fats and oils)

Fatty alcohol blends used are c12/14 and c16/18 range .

Raw materials

2) Carbohydrate source

The hydrophilic part of the molecule is derived from a carbohydrate .

Both Polymeric and monomeric carbohydrates are suitable as raw

materials.

Polymeric carbohydrates include starch or glucose syrups while

monomeric carbohydrates include water free glucose, glucose
monohydrate (dextrose)

Synthesis

2 methods of synthesis are :

1)Direct process
2)Trans - acetalization process

in either case reaction can be done out in batches or continuously

Direct process

In this process carbohydrate reacts directly with fatty alcohol to form

required long chain alkyl polyglycosides.

In the direct synthesis, monomeric solid glucose types are used as fine
particles. (Carbohydrate is usually dried to remove the crystal- water). It
minimizes the side reactions to take place.

Highly degraded glucose syrup (DE>96) are used to react in such

process.

Sometimes, second solvents are used for providing a stable fine- droplet
dispersion between alcohol and glucose syrup.

This process is simpler from equipment point of view (since single stage
process).

Transcetalization process

It is a 2-stage process.

In first stage, carbohydrate reacts with a short-chain alcohol (n-butanol

or propylene glycol).

In second stage, short chain alkyl glycoside is trans-acetalized with a

long chain alcohol (C12-C18) to form required alkyl polyglycoside.

Industrial production

For production of alkyl polyglycosides based on fischer synthesis are

determined by type of the carbohydrate types used and by the chain length
of the alcohol used.

Low reaction temperatures (< 100 C) in the acetalization lead to alkyl

polyglycosides low in secondary products.

However, low temperatures result in relatively long reaction times and low
specific reactor efficiencies.

Relatively high reaction temperatures (> 100 C, typically 110-120 C) can

lead to changes in color of the carbohydrates.

By removing the lower-boiling reaction products (water in the direct

synthesis, short-chain alcohols in the transacetalization process) from the
reaction mixture, the acetalization equilibrium is shifted to the product side

Typical reaction pressures in the transacetalization and direct synthesis

variants are between 20 and 100 mbar.

Selection of catalyst for glycosidation process is also important.

Acetalization or transacetalization in the Fischer synthesis is catalyzed

by acids

Acids with sufficient strength suitable for this purpose are sulfuric acid,
para-toluene- and alkylbenzene sulfonic acid and sulfo succinic acid.

The reaction rate is dependent on the acidity and the concentration of

the acid in the alcohol.

Flow diagram for industrial

production

Industrial scale glycosidation process

Mass balance of product

For 100 kg of product :

Glucose +

We require

dodecanol

1. Glucose : 51.72 kg
2. Dodecanol : 53.44 kg
(Assuming 100% conversion )

dodecyl octyl glycoside

Application of alkyl polyglycosides

Bottle washing

Highly alkaline formulations

Metal Cleaners

Paint strippers

Personal care products

Aluminum brighteners

Glass cleaners

Highly alkaline detergents

Detergents

Industrial manufacturer

HENKEL is major player in production and R&D of alkyl polyglycosides.

Other companies which are offering such surfactants are:

BASF

AKZO NOBEL

SEPPIC

ICI

REFERENCES

Nonionic Surfactants: Alkyl Polyglucosidesedited by Dieter Balzer,

Harald Luders

Alkyl Polyglycosides: Technology, Properties, Applications edited

by Karlheinz Hill, Wolfgang von Rybinski, Gerhard Stoll

http://www.dow.com/surfactants/