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IFP : a research and industrial development and training center Active in the fields of : - oil, gas and coal, their uses, in particular in transport, - the new energy and environmental technologies IFP's staff : 1,125 researchers 239

SLIDE 1

IFP : a research and industrial development

and training center

SLIDE 2

Active in the fields of :

oil, gas and coal, their uses, in particular in transport,
the new energy and environmental technologies

IFP's staff : 1,125 researchers 239 doctoral and post doctoral researchers An applied research : a portfolio of more than 12,000 living patents A policy of commercial development of the results through the licensing

f processes, software, equipment, etc.

SLIDE 3

Objectives are :

to design refining and petrochemical processes that are clean and efficient
to diversify sources of energy for the production of fuels and hydrogen
to control emissions of CO2

Skill areas :

catalysis, separation technologies, analysis and physico-chemical characterization, thermodynamics, chemical engineering, modeling of processes, molecular modeling, high-flow tests and experiments

1,800 industrial units worldwide Recent achievements :

Esterfip-H: biodiesel production process by transesterification of vegetable oils. Marketed by Axens.

Esterfip-H unit under construction in Sète, France.

In refining-petrochemicals

SLIDE 4

ASIE

AM. NORD

EUROPE 18 6 7 MOYEN ORIENT 1

AM. SUD 1

AFRIQUE 2 ASIE

AM. NORD

EUROPE 18 6 7 MOYEN ORIENT 1

AM. SUD 1

AFRIQUE 2

Dimersol Process : for gasoline

One of the first examples of

application of homogeneous catalysis in refining industry

First industrial unit in 1977
35 units in operation worldwide
3.5 Mt products / year

+ +

6% 72 % 22 % Dimerization of propylene into isohexenes : octane booster for gasoline

SLIDE 5

Dimersol Process : for chemistry

+ +

6% 59% 34%

First industrial unit in 1980
0.4 Mt products / year

Dimerization of butenes into octenes : raw materials for the production of PVC phthalate plasticizers

SLIDE 6

mole AlCl3

T°C 20°C

60°C

liquid

solid solid

AlCl3

EMICl

Diagramme de phases

Cl

N-Me Et-N

AlCl3

+

EMIC Ethyl Methyl Imidazolium Chlorure

Non-Aqueous Ionic Liquids

From non aqueous electrolytes for batteries ...to a new class of solvents for catalysis

SLIDE 7

Products Reactants

solvent + catalyst

Reactants Products

Ni

Liquid-Liquid Biphasic Catalysis

SLIDE 8

Butenes Catalyst toward washing and distillation section

Dimersol process Difasol process

Products Reactants Active Phase containing the catalyst toward distillation section 4 reactors of 120 m3 reactor of 50 m3 catalyst consumption divided by 10 higher yield in dimers 20t/h feed rate

SLIDE 9

Dimerization of ethylene into 1-

butene (Ti homogeneous catalyst)

1-Butene is used as co-

monomer for polyethylene manufacture

Alphabutol process

First industrial unit in 1987
20 units in operation
0.4 Mt/Y
2005 : 3 new units 110 000t/Y

total capacity

AFRIQUE 2 MOYEN ORIENT 9 ASIE 8 AFRIQUE 2 MOYEN ORIENT 9 ASIE 8

SLIDE 10

M(CO)6/Al2O3 (M = Mo, W) Ethylene 2-Butene (trans et cis) Propylene

2 +

90°C-315°C

Banks et Bailey (Philips Petroleum Co.)

I. & E. C. Product Research and Development

1964, 3, 170-173.

1964 : a magic year...

WCl6/AlEt3

MoCl6/AlEt3

G. Natta Angew. Chem. Int. Ed. Engl. 1964, 3, 723
E. O. Fischer Angew. Chemie 1964, 76, 645

Heterogeneous catalysis... Homogeneous catalysis Metallocarbene

a new metal–carbon bond

SLIDE 11

2 +

2-pentene 2-butene 3-hexene

Disproportionation of olefins

Ethylene 2-Butene (trans et cis) Propylene

2 +

SLIDE 12

"Pairwise" mechanism

SLIDE 13

SLIDE 14

M(CO)6/Al2O3 (M = Mo, W) Ethylene 2-Butene (trans et cis) Propylene

2 +

90°C-315°C

Banks et Bailey (Philips Petroleum Co.)

I. & E. C. Product Research and Development

1964, 3, 170-173.

1964 : a magic year...

WCl6/AlEt3

MoCl6/AlEt3

G. Natta Angew. Chem. Int. Ed. Engl. 1964, 3, 723
E. O. Fischer Angew. Chemie 1964, 76, 645

Heterogeneous catalysis... Homogeneous catalysis Metallocarbene

a new metal–carbon bond

SLIDE 15

R2 R1

+

R1 R2 R1 R1 R2 R2 R1 R1 R2 R2

+ + + +

cyclopentene 2-pentene

C10 C9 C11 homogeneous W catalyst

Co-reaction of cyclopentene with 2-pentene

Hérisson et Chauvin Die Makromolekular Chemie 1971, 141, 161-176.

SLIDE 16

R C H M (CH2)n C H M CH CHR HC HC (CH2)n

+

etc…

Linear polymers with high molecular weight : observed at the beginning of the reaction

Carbene mechanism

[W] C H R

SLIDE 17

R1CH=CHR2

Soufflet, Commereuc et Chauvin C. R. Acad. Sc. 1973, 276, 169-171

formation of -olefins

Formation of the metallocarbene : WCl6 + Sn(CH3)n

[W]=CH2

SLIDE 18

Hérisson et Chauvin Die Makromolekular Chemie 1971, 141, 161-176.

SLIDE 19

Cross Metathesis (CM) Ring Closing Metathesis (RCM) Acyclic Diene Polymerization (ADMET) Ring Opening Metathesis (ROMP)

R1 R2 n R1 R1 R2 R2