Joseph H. Simons and his work in Fluorine Chemistry

Journal of Fluorine CRcmistry. 32

JOSEPH

(I 986) 25-28

H. SIMONS AND HIS WRK

25

IN FLUORINE

CHEMISTRY

R. D. DRESDNER

Department

of Chemistry,

University

of Florida,

Gainesville,

Florida

32611

(U.S.A.)

Professor tist.

Joseph

His interests

physics

H. Simons was the model of the interdisciplinary and accomplishments

and engineering.

Nevertheless

straddled

his most prolific

found in the areas of fluorine

and fluorocarbon

studies

research

and his early personal

ern University properties

and Pennsylvania

and chemistry

For example, ment of eight point,

[l-7] properties

vapor pressure,

ity, the molecular organic

of hydrogen

liquids

which HF was used as a reagent

181 and organosilicon

area of chemistry

rearrangement

reactions.

being exemplary

initiated

in two kinetic chloride

studies

[20, 211.

'catalyed'

inhibited

for the practical

the fluorination

fluorine

of the alkylation

was apparently

Methods

However,

of different

by mercury

generated

0020-l 139/86/$3.50

191.

fluorides

viscosof HF in

in work in such as a

Some of the data collec-

for the phenomenon

and exploited

in alkylation,

of hydrogen

manifested

by HF.

by Simon6 at Penn.

condensation

and

in some 20 publications

including

only ten are listed in the references

of the nature of the work

the HF catalysis

heat of vaporization,

and association

This work resulted

of DDT.

with the measure-

He also was involved

fluorides

State was the use of HF as a catalyst

a new preparation

at Northwest-

These were the freezing

to prepare

evidence

and its effect on the structure

Another

investigator,

tension,

in reactions

ted in these early studies provided bonding

His graduate

of the gas and liquid and the solubility and octane.

are

in the liquid and gas states.

of this material.

such as benzene

fluorocarbonate

fluoride

surface

achievements

chemistry.

scien-

chemistry,

dealt, by and large, with the

as a principle

density,

structure

fields,

work as a faculty person

State College

he was associated,

several

[lo-191.

A more precise

of phenol with -t-butyl chloride The alkylation

scale preparation

a process

began with

usually

or one of its salts to inhibit explosions method

is recorded

by HCl 1221.

of fluorocarbons

of carbon,

by the high temperature

study of

of toluene with -t-butyl

by HF but enhanced

varieties

as

[23, 241 using

[25].

0 ElsevierSequoia/Printedin The Netherlands

26 Professor chemistry

Simons

continued

his researches

of fluorine-containing Publications

and thereafter. other organic this period

fluorides

compounds

on the preparation

chemical

carbon bond in fluorocarbons

and

of World War II

halides

[26,

acid

Cleavage

[32].

by Cl2 and Br2 1301 suggested

of the carbon-carbon

271,

129, 301 appeared

papers on the dielectric

[31] and trifluoroacetic

on the hydrogenolysis

the period

of CF3 derivates

[28] and the fluorocarbon

as well as physical

of fluorocarbons

in the preparation

through

in

properties

of a carbon-

the successful

bond to form fluorocarbon

work

hydrides

1331. Although containing carried papers

the work on the electrochemical

compounds

out over a period on the process

Pandora's

exotic compound

entered

the chemical

process

[35] and the preparation

in the early

literature

[373, ethers

The synthetic

[38], acids

Simons moved

reaction

to the University

1361,

[40].

and properties

of silver

of its acid in aqueous

of Florida

a part of the department

ketones,

of the esters with PC15

dimers

Chemistry

[43] esters

[48], mercury

of the acid dimers

Professor

in fluorine

Simons'

two pieces

researches

of work,

Besides

acids

Chemistry,

which

This period

and fluorocarbon

acid

of the amides of

chemistry

terminated

of fluorocarbon

[51] and the silver halide

iodides

complexes

[52].

his research

RF and its solutions

or diluents

1451 the

of fluorocarbon

derivates

1501.

supported

of new interests,

[44], ethers

the first on the preparation

the use of solvents

of fluorocarbon

was generously

[46], the preparation

[47] and 'thiocyanates'

and set up his of chemical

a large breadth

[49] and the acid hydrolysis

RF t561,

the basic

at Penn. State terminated

of the preparation

Much of his work in Fluorine

such as fluorocarbon-aromatic

methods

describing

[393 and amines

It took a novel turn and reflected

without

opened a

many of which

of perfluoropiperidenes

1411 and the decomposition

in Reed Laboratory,

engineering.

with

fluorine

in the form of patents

1950s and consisted

Professor

amide

containing

and properties

series of five

[42].

activities

by 3M.

fluorine-

This process

1949 1341.

fluorine work that was initiated

undecafluorocarboxylate solution

to prepare

of quite a few years the classic

did not appear until

box for preparing

cyclohexamines

process

using HF as the solvent and source of fluorine was

in fluorine

chemistry

Joseph

Simons wrote reviews

[53], and on HF [54] in the 5 volume compendium,

he also edited.

or prescriptions

He contributed,

for the safe preparation

too, to Inorganic of fluorine

CF4 [57, 581, SF6, SeF6, and TeF6 [59] and BrF3 [60].

on

Fluorine Syntheses

[55], anhydrous

27 This summary

of Joseph

is by no means a complete effort and thoughtful broad

research

Simons'

deliberation

scope of his interests,

involved.

his dedication

of the large number of people who benefited turn, helped

to contribute

activities

in fluorine

review of his work nor does it reflect It tends rather

chemistry

the time,

to reflect

the

to his goals and the productivity from his mentorship

and who, in

to his memory.

REFERENCES

J.H.

Simons,

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2

J.H. Hildebrand

4

J-H. Simons,

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J.H. Simon6 and J. W. Bouknight,

J. Am. Chem. Sot., -54 (1932) 129.

J. Am. Chem. Sot., -55 (1933) 1458.

J.H. Bauer, J.Y. Beach and J.H. Simons, J. Am. Chem. Sot., -61 (1939) 19. J.H. Simons and R.D. Dresdner, J.H. Simons,

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J. Am. Chem. Sot., -53

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10

J.H. Simons,

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11

J.H. Simons,

J.C. Bacon, C.W. Bradley,

9

Paul Tarrant,

J. Am. Chew

12

J.H. Simons and S. Archer,

13

J.H. Simons,

J.I. Cassaday,

E.I. Hoeberg,

and

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S. Archer and Elizabeth

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2955. 14

D.I. Randall

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1795. 15

J.H. Simons and H.J. Passino,

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1624. 650.

16

J.H. Simons and G.C. Bassler,

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17

J.H. Simons and A.C. Meunier,

J. Am. Chem. Sot., -63 (1941) 1921.

18

J.H. Simon8 and A.C. Werner,

J. Am. Chem. Sot., -64

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19

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20

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21

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22

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23

J.H. Simons

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24

J.H. Simons

and L.P. Block, J. Am. Chem. Sot., -61 (1939) 2962.

25

J.H. Simons,

26

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(1937)

1407.

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28

27

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28

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29

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Chem.

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(1943)

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31

W.A. Wilson,

32

J.H. Simons and K.E. Lorentzen,

33

W.R. James,

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T.J. Brice, R.D. Dresdner,

Hogg, W.H. Pearlson

and W.A. Wilson,

H.T. Francis,

J. Electrochem.

35

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36

J.H. Simons,

U.S. Patent 2490098,

Dec. 6, 1949.

37

J.H. Simons,

U.S. Patent 2490099,

Dec. 6, 1949. Mar.

2456027 and 2456028,

W.J. Harland,

Sot., -95 (1949) 47-67

Dec. 14, 1948.

38

J.H. Simons,

U.S. Patent

39

J.H. Simons,

U.S. Patent 2593737,

40

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U.S. Patent 2616927, Nov. 4, 1952.

41

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42

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(1951)

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45

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46

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52

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