WATER is a green SOLVENT in organic synthesis

HOCHI
CHIMINH
MINHUNIVERSITY
UNIVERSITYOF
OFTECHNOLOGY
TECHNOLOGY
HO

PRESENTATION

WATER is a green SOLVENT in organic synthesis
Dr Nam Thanh Son Phan


Group 1

01

Nguyễn Hoàng Đại Lợi
61305029

Trần Bảo Thanh vân
03

61304781 

Võ Quốc Anh
02

61300158

OUTLINE
The usual
usual properties
properties of
of
The
liquid water.
water.
liquid

Introduction
Introduction

I

Water
Water is
is a
a green
green solvent
solvent in
in

T

organic
organic synthesis
synthesis

Why
Why is
is water
water
green?
green?

W

3

W


OUTLINE
The usual
usual properties
properties of
of
The
liquid water.
water.
liquid

Introduction
Introduction

I

Water

Water is
is a
a green
green solvent
solvent in
in

T

organic
organic synthesis
synthesis

Why
Why is
is water
water
green?
green?

W

4

W


 INTRODUCTION

 Over 70% the Earth’s surface

  70% human bodies


 INTRODUCTION

 Water is limited resource


 INTRODUCTION

 In Chemistry:
 Water is a solvent  because of its high 
polarity. It is able to dissolve or dissociate 
many particle.

 A 104.5° bond angle creates a very 
strong dipole.

 Water has hydrogen bonding.

The salt is the solute, the water is the solvent.


OUTLINE
The usual
usual properties
properties of
of
The

liquid water.
water.
liquid

Introduction
Introduction

I

Water
Water is
is a
a green
green solvent
solvent in
in

T

organic
organic synthesis
synthesis

Why
Why is
is water
water
green?
green?

W

8

W


 The usual properties of water

•

Boiling Point and Freezing Point

•

Heat of Vaporization:
2.27 MJ/Kg


 The usual properties of water

 Surface Tension
80
70
60
50
40
30
20
10

0

acetone

benzen

ethyl acetate

Surface tension of water and other liquids

water


 The usual properties of water

 Vapor Pressure


 The usual properties of water
 Viscosity

0.9
0.8
0.7
0.6
0.5
0.4
0.3
0.2
0.1

0

Methanol

Acetonitrile

Viscosity of water and other liquid

Water


 The usual properties of water

 Cohesion:
 - Water's strong attraction 
to itself


 The usual properties of water

 State


OUTLINE
The usual
usual properties
properties of
of
The
liquid water.

water.
liquid

Introduction
Introduction

I

Water
Water is
is a
a green
green solvent
solvent in
in

T

organic
organic synthesis
synthesis

Why
Why is
is water
water
green?
green?

W

15

W


Water is a green solvent in origin synthesis


•  Diels- Alder reaction (Diene synthesis)

Reactor between a conjugated diene and dienophile (  component) to form a  cyclic 
structures.


Water is a green solvent in origin synthesis

 Turn of speed
  Ronald Breslow-Columbia University in New York -US. Breslow’s seminal paper on 
hydrophobic acceleration of Diels–Alder reactions appeared in 1980

  Better selectivity
  Faster reaction rates
  Higher yields
  Water’s environmentally benign


Water is a green solvent in origin synthesis

Floating on water

  But in almost all reactions in water, if thereagents aren’t soluble in water, but 
float on top, the reaction works even better.


Water is a green solvent in origin synthesis
Ronald Breslow

•
•

Synthetic chemists are under increasing pressure to exchange traditional organic 
solvents for water.
Water offers a host of advantages as a solvent – being cheap, abundant, nonflammable and non-toxic.


Water is a green solvent in origin synthesis
Ronald Breslow

•
•

Reactions run in water can give better results, including faster reaction rates and 
higher product yields.
Academic chemists have shown that a wide range of reactions can be run in water, and 
industry is increasingly adopting water as a solvent.


Water is a green solvent in origin synthesis

  Reduction of nitroarene in water is a green solvent: A  green  

synthetic method  for  fast  and convenient with reducing agent is NaBH4 
and effective catalyst is Nikel salt (NiCl2.6H20)


Water is a green solvent in origin synthesis

 Anilin: a toxic organic compoud, is used to produce precursor to
polyurethane and other industrial chemicals

 Rubber processing chemicals.
 Herbicides.
 Dyes and pigments.


Water is a green solvent in origin synthesis

Nitroarene: liquid, 
colourless, almod and very 
toxic.

Sodium borohydride(NaBH2): 

Nickel salts( NiCl2.6H20): is chosen as 

inorganic compound, white 

the effective catalyst, the anhydrous is 

powder, is used widely reducing 

yellown and the nickel salts in aqua is 

agent in organic chemistry

green.


Water is a green solvent in origin synthesis
TLC: thin layer chromtograph

  To purify determination of substrates, product and reaction.
  Stationary phase: silicagel 60 F254 aluminium sheet.
  Moble phase: solvent (CCl4/Et20:5/2)


 Experiment
Nitrobenzene

Solution (nitrobenzene:0.1231 g and
water:2ml)

Nickel salts (0,1188g)

NaBH4(0,1134g)

Stirr

Monitored

Extracted

Dry

Evaporation

Anilin

For 20 minutes and 60

By TLC

With CH2CL2