PERACETIC ACID

1

Peracetic Acid

1

O

H

O

O

[79-21-0]

C

2

H

4

O

3

(MW 76.06)

InChI = 1/C2H4O3/c1-2(3)5-4/h4H,1H3
InChIKey = KFSLWBXXFJQRDL-UHFFFAOYAD

(electrophilic reagent capable of reacting with many functional
groups; delivers oxygen to alkenes, sulfides, selenides, and

amines)

Alternate Name:

peroxyacetic acid.

Physical Data:

mp 0

◦

C; bp 25

◦

C/12 mmHg; d 1.038 g cm

−

3

at

20

◦

C.

Solubility:

sol acetic acid, ethyl acetate, CHCl

3

, acetone, ben-

zene, CH

2

Cl

2

, ethylene dichloride, water.

Form Supplied in:

40% solution in acetic acid (d 1.15 g cm

−

3

)

having approximately the following composition by weight:
peracetic acid, 40–42%; H

2

O

2

, 5%; acetic acid, 40%; H

2

SO

4

,

1%; water, 13%; diacetyl peroxide, nil; other organic com-
pounds, nil; stabilizer, 0.05%. A solution of the peracid in ethyl
acetate is also available commercially.

Analysis of Reagent Purity:

assay using iodometry;

2

estimation

of diacetyl peroxide.

3

Preparative Methods:

prepared in the laboratory by reacting

Acetic Acid with hydrogen peroxide in the presence of cat-
alytic quantities (1% by weight) of Sulfuric Acid; when 30%
H

2

O

2

is used the concentration of the peracid reagent obtained

is less than 10%.

1a

If a stronger solution of the reagent is

required, 70–90% H

2

O

2

must be used. Caution: for hazards

see Hydrogen Peroxide. Hydrogen Peroxide–Urea (which is
commercially available and is safe to handle) has been used as
a substitute for anhydrous hydrogen peroxide.

3

In the prepa-

ration of peracetic acid from acetic anhydride and H

2

O

2

, the

dangerously explosive diacetyl peroxide may become the major
product if the reaction is not carried out properly.

1a

Purification:

peracetic acid is rarely prepared in pure undiluted

form for safety reasons. The commercially available material
contains acetic acid, water, H

2

O

2

, and H

2

SO

4

. After neutral-

ization of the sulfuric acid, this reagent is satisfactory for most
reactions. If water is undesirable, an ethyl acetate solution of the
reagent may be used. Details for the preparation of the H

2

O

2

-

free reagent are available.

4

Handling, Storage, and Precautions:

peracetic acid is an explo-

sive compound but is safe to handle at room temperature in or-
ganic solutions containing less than 55%. Use in a fume hood.
Since peroxides are potentially explosive, a safety shield should
generally be used.

5

Peracetic acid can be stored at 0

◦

C with es-

sentially no loss of active oxygen and at rt with only negligible
losses over several weeks.

Original Commentary

A. Somasekar Rao & H. Rama Mohan
Indian Institute of Chemical Technology, Hyderabad, India

General Considerations.

Peracetic acid oxidizes simple

alkenes, alkenes carrying a variety of functional groups (such as
ethers, alcohols, esters, ketones, and amides), some aromatic com-
pounds, furans, sulfides, and amines. It oxidizes β-lactams in the
presence of catalysts. Ketones and aldehydes undergo oxygen in-
sertion reaction (Baeyer–Villiger oxidation).

Epoxidation of Alkenes. Peracetic acid is a comparatively

safe reagent for small-scale reactions. In industry, to avoid the
hazards involved in handling large quantities of the reagent, it is
prepared in situ. Peracetic acid prepared in this fashion is widely
used for epoxidation of vegetable oils and fatty acid esters. To
the substrate in acetic acid containing catalytic (1% by weight)
quantities of H

2

SO

4

maintained around 50

◦

C is added gradually,

with stirring, 50% H

2

O

2

at such a rate that there is no buildup in the

concentration of H

2

O

2

. The peracid is consumed as it is formed

(eq 1). The addition of H

2

O

2

is usually completed in 2 h and then

the temperature is raised to and maintained at 60

◦

C until all the

H

2

O

2

is consumed (about 3 h). The reaction mixture is diluted

with water, at which point the epoxides (being water-insoluble)
separate out. The use of hexane during the reaction minimizes
epoxide ring opening. Since the catalyst (H

2

SO

4

) is essential for

the speedy formation of peracetic acid, in situ methods can be
used for preparing only those epoxides which can tolerate the
presence of the acid catalyst. Epoxides of fatty acid esters are
obtained in good yields if the reaction temperature and time taken
for completion of the reaction are properly controlled.

(1)

MeCO

2

H

+

H

2

O

2

MeCO

3

H

+

H

2

O

H

+

Peracetic acid in ethyl acetate is a better reagent for preparing

epoxides from alkenes than the reagent in acetic acid since the
large quantities of acetic acid in the latter reagent facilitate epoxide
ring opening. However, since the reagent in acetic acid is more
readily available, it is normally used for epoxidation; the sulfuric
acid present in the commercial sample has to be neutralized by
adding sodium acetate before the epoxidation. After epoxidizing
the alkene with peracetic acid, the reaction mixture is diluted with
water. The unreacted peracid, acetic acid, and traces of hydrogen
peroxide are removed in the aqueous layer. The separated epoxide
is filtered if it is a solid; when the epoxide is a liquid, the organic
layer is separated using a small quantity of solvent, if needed.
Another method of workup is to remove unreacted peracid and
acetic acid through evaporation under reduced pressure.

Epoxidation of terminal alkenes with organic peracids is slug-

gish since the double bond is not electron rich (eq 2).

6

(2)

O

MeCO

3

H, NaOAc

Na

2

CO

3

, CH

2

Cl

2

20 °C, 4 d

53%

Adequately substituted acrylic esters furnish epoxides in good

yields. Ethyl crotonate has been epoxidized in kg quantities
according to eq 3;

7

the workup is simple, involving direct frac-

tionation of the reaction mixture. For the preparation of epoxide
(1) from ethyl crotonate using Trifluoroperacetic Acid, the yield
is 73%.

8

The sensitive allylic epoxide (2) has been prepared

according to eq 4.

9

This procedure has been applied successfully

Avoid Skin Contact with All Reagents

2

PERACETIC ACID

for the preparation of allylic epoxides from 1,3-cyclopentadiene,
1,3-cycloheptadiene, and 1,3-cyclooctadiene.

CO

2

Et

CO

2

Et

(3)

O

MeCO

3

H, EtOAc

85 °C, 5.5 h

75%

(1)

(4)

(2)

O

40% MeCO

3

H

Na

2

CO

3

, CH

2

Cl

2

rt

69%

Epoxidation of the triene (3)

2

is regioselective, involving re-

action at the tetrasubstituted double bond (eq 5). Epoxidation of
(3) using m-Chloroperbenzoic Acid furnishes the monoepoxide
in 76% yield.

10

Epoxidation of the diene (4) was regio- and stereo-

selective (eq 6);

11

the more substituted double bond was epoxi-

dized from the less hindered side.

(5)

(3)

O

MeCO

3

H, CH

2

Cl

2

Na

2

CO

3

, 15 °C

79–84%

O

O

TBDMSO

H

H

H

O

O

TBDMSO

H

H

H

MeCO

3

H (2.9 equiv)

EtOAc, 25 °C, 10.5 h

72%

(6)

O

(4)

Epoxidation of the unsaturated γ-lactone (5) furnished stereo-

selectively the epoxide (6), involving approach of the reagent from
the more hindered side of the double bond (eq 7).

12

This selectivity

is observed only when acetic acid is the solvent. The selectivity
was much less when m-CPBA was used.

O

O

O

O

O

O

O

(7)

MeCO

3

H, AcOH

25 °C, 16 h

96%

O

+

(6)

(5)

89:11

Moderate stereoselectivity is observed during the epoxidation

of sterically unbiased 3,3-diarylcyclopentenes; the major product
is formed through approach of the electrophile from the side trans
to the better electron donor (eq 8).

13

O

2

N

O

2

N

O

O

2

N

(8)

O

10 equiv MeCO

3

H

CH

2

Cl

2

, 23 °C, 18 h

+

73:27

A systematic study of the epoxidation of the acyclic allyl

alcohol (7) has been carried out, employing several reagents.

14

Epoxidation with peracetic acid generated from urea/H

2

O

2

showed small syn selectivity (eq 9). m-CPBA epoxidation of (7)
furnished in 87% yield a 40:60 mixture of the epoxy alcohols (8)
and (9).

OH

OH

(9)

O

(7)

OH

urea–H

2

O

2

Ac

2

O, Na

2

HPO

4

CH

2

Cl

2

62%

(9)

O

(8)

+

57:43

Epoxidation of Alkenes via Peracids Generated In Situ.

Alkenes have been epoxidized by reacting them with peracids
generated in situ. The system consisting of molecular oxygen and
aldehydes, particularly isobutyraldehyde and Pivalaldehyde, con-
verts various alkenes to epoxides in high yields when they are
reacted at 40

◦

C for 3–6 h (eq 10).

15

H

C

5

H

11

H

H

C

5

H

11

H

(10)

O

Me

2

CHCHO (1.5 equiv)

EDC, O

2

bubbling

40 °C, 3 h

100%

Oxidation of Furans. 2,5-Disubstituted furans are oxidatively

cleaved by peracids; for example, see eq 11.

16

m

-CPBA can also be

used for this reaction. 

3

-Butenolides have been synthesized by

oxidizing 2-trimethylsilyl furans with peracetic acid; as in eq 12.

17

O

TMS

Et

O O

TMS

Et

(11)

NaOAc (1.2 equiv)
MeCO

3

H (4 equiv)

CH

2

Cl

2

, 7 °C, 1 h

70%

A list of General Abbreviations appears on the front Endpapers

PERACETIC ACID

3

O

TMS

R

O

O

R

MeCO

3

H

NaOAc, CH

2

Cl

2

7 °C, 3.5 h

78%

(12)

R = Me

2

CHCH

2

CH

2

-

This reaction does not proceed smoothly when there is a

hydroxyl group in the furfuryl position; however, the reaction is
facile if the furfuryl OH is blocked. The reaction does not take
place if electron-withdrawing groups are present on the furan ring.
m

-CPBA is not a good reagent for this oxidation. An interesting

application of this reaction has been published.

18

Oxidation of Aromatic Compounds.

Suitably substituted

aromatic compounds are oxidized efficiently to the quinones by
peracetic acid. The quinone (10) is obtained in 22% yield by oxi-
dizing naphtho[b]cyclobutene.

19

Slow addition of 1,5-dihydroxy-

naphthalene to excess peracetic acid furnished juglone (11) in
46–50% yield.

20

O

O

O

O

OH

(10)

(11)

Baeyer–Villiger Oxidation.

A systematic study of the

Baeyer–Villiger reaction of the bicyclic ketone (12) has been
carried out employing different organic peracids.

21

Selective

formation of lactone (13) was highest when peracetic acid was
used (eq 13). Reaction of (12) with m-CPBA furnishes a 55:45
mixture of (13) and (14) in 81% yield.

MeO

OCH

2

Ph

O

MeO

OCH

2

Ph

O

O

O

MeO

OCH

2

Ph

(12)

O

H

2

O

2

, MeCO

3

H

NaOAc

36 h, rt

72%

+

(13)

(13)

(14)

92:8

Position-specific Baeyer–Villiger rearrangement has been

observed in the reaction of peracetic acid with some polycyclic
ketones.

22,23

An ε-lactone, required for the synthesis of erythrono-

lide B, was synthesized in 70% yield through position-specific
Baeyer–Villiger rearrangement of a cyclohexanone having sub-
stituents on all the ring carbons;

24

the ketone was treated with

excess 25% peracetic acid in ethyl acetate for 6 days at 55–58

◦

C.

Peracetic acid oxidation of the keto β-lactam (15) furnishes stereo-
selectively the interesting β-lactam (16) (eq 14);

25

the initially

formed Baeyer–Villiger reaction product undergoes further reac-
tion. Ketone (15) has also been reacted with m-CPBA in acetic
acid but the selectivity is slightly less, forming (16):(17) in 10:1
ratio.

O

O

NH

H

H

O

O

NH

O

OCHO

NH

O

OCHO

OAc

H

OAc

H

MeCO

3

H, NaOAc

AcOH

83%

+

(14)

(15)

(16)

H

H

(17)

11:1

Ruthenium- and Osmium-catalyzed Oxidations. α-Ketols

have been synthesized by reacting alkenes with peracetic acid
in the presence of a Ruthenium(III) Chloride catalyst.

26

α

-Ketol

(19) was synthesized from the alkene (18) chemo- and stereoselec-
tively (eq 15). The two-phase aqueous system is essential for this
reaction. Conjugated dienes, allylic azides, and α,β-unsaturated
esters have been oxidized with this reagent.

OAc

MeO

2

C

OAc

MeO

2

C

O

OH

(15)

RuCl

3

, MeCO

3

H

MeCN, H

2

O, CH

2

Cl

2

55%

(18)

(19)

The methylene group adjacent to the nitrogen of β-lactams has

been oxidized with peracetic acid in the presence of a ruthe-
nium catalyst (eq 16).

27

Peracetic acid is the best oxidant for

this reaction. Instead of ruthenium, OsCl

3

can be used to cat-

alyze the oxidation.

28

The peracetic acid required for the reaction

can be generated in situ from acetaldehyde and molecular oxygen
(eq 17).

29

NH

O

OTBDMS

NH

O

OTBDMS

(16)

OAc

5% Ru cat

NaOAc, AcOH, MeCO

3

H

99% de

in EtOAc, rt, 2.5 h

99%

NH

O

NH

O

(17)

OAc

Ru cat, MeCHO, O

2

MeCO

2

H, NaOAc

EtOAc

88%

Other Applications. Peracetic acid has been used to (a) ox-

idize primary amines to nitroso compounds,

30

(b) oxidize sec-

ondary alcohols to ketones in the presence of a Cr

VI

ester catalyst

(eq 18)

31

or sodium bromide,

32

(c) oxidize sulfenamides to sul-

fonamides (eq 19),

33

(d) oxidize iodobenzene to iodosobenzene

diacetate

34

and iodoxybenzene,

35

and (e) oxidize N-heterocycles

such as pyridine to N-oxides.

36

α

,β-Unsaturated aldehydes (and

α

,β-unsaturated ketones) do not undergo facile epoxidation with

peracetic acid since the double bond is not electron rich. However,
the acetals of α,β-unsaturated aldehydes can be oxidized readily
(eq 20).

37

For the epoxidation of α,β-unsaturated aldehydes with

H

2

O

2

/base see Hydrogen Peroxide.

OH

O

Cr

O

O O

(18)

MeCO

3

H

0 °C, CH

2

Cl

2

CCl

4

, 30 min

( )

3

O

( )

3

96%

S

N

EtO

SNH

2

S

N

EtO

SO

2

NH

2

(19)

MeCO

3

H

K

2

CO

3

, EtOH, H

2

O

88%

Avoid Skin Contact with All Reagents

4

PERACETIC ACID

Ph

H

H

O

O

Ph

H

H

O

O

(20)

O

MeCO

3

H

EtOAc

40 °C, 7 h

45%

For industrial applications, peracetic acid is the most widely

used organic peracid since it is inexpensive. It is the only com-
monly used peracid which can be prepared in situ for epoxida-
tion reactions, since the acid catalyst (1% H

2

SO

4

; eq 1), which

can facilitate epoxide ring opening, is used in low concentrations;
the accompanying acetic acid, being a weak acid, is not very ef-
ficient in epoxide opening. The in situ method is not hazardous.
Although the reagent is available commercially, it is also prepared
in the laboratory since its preparation is easy, fairly fast, and no
solvent is required for isolation. Epoxidation reactions and sub-
sequent workup can be performed with no solvent, or only small
quantities of solvent since the peracid and accompanying acetic
acid are both water soluble and volatile. It is not essential that
the substrate should dissolve in the reagent (peracetic acid–acetic
acid).

First Update

John E. Hofferberth
Kenyon College, Gambier, OH, USA

General Considerations. Peracetic acid has recently found

utility as a primary oxidant in catalytic oxidations. To avoid
the degradation of certain catalysts, a convenient preparation
of the reagent devoid of the sulfuric acid found in commercial
peracetic acid has been employed. The preparation involves treat-
ment of acetic acid with 50% hydrogen peroxide in the pres-
ence of the acidic resin Amberlite IR-120. Removal of the resin
yields solutions containing 8–10% peracetic acid (in acetic acid)
with pH ∼ 4 and <1% residual hydrogen peroxide.

38

Appropriate

caution should be exercised during the preparation of this
reagent as concentrated solutions of hydrogen peroxide in organic
solvents are potentially explosive.

Epoxidation of Electron-deficient Alkenes.

Electron-rich

olefins are readily epoxidized by peracetic acid while terminal
and electron-deficient olefins exhibit only sluggish reactivity. A
number of manganese complexes have been identified as effi-
cient catalysts for the peracetic acid epoxidation of electron-
deficient olefins.

38,39

The complex [Mn

II

(R,R-mcp)(CF

3

SO

3

)

2

]

(20) is sufficiently robust to tolerate commercial preparations of
peracetic acid as a primary oxidant and has been shown effective
in the epoxidation of a broad scope of electronically and streri-
cally distinct alkenes (eq 21). The electrophilic character of the
active oxidant allows for regioselective epoxidation of electron-
rich double bonds at reduced temperature (eq 22). The simple com-
plex [Mn

II

(bipy)

2

(CF

3

SO

3

)

2

] is an exceptionally active catalyst,

which benefits from the commercially available bipy ligand, how-
ever, requires peracetic acid devoid of sulfuric acid as the primary
oxidant (eq 23). Only modest enantio- and diastereoselectivites
have been observed for peracetic acid epoxidations catalyzed by
this class of manganese complexes.

N

N

Me

Me

N

N

(R,R-mcp) =

OAc

OAc

O

20 (0.1 mol

%)

(21)

32% CH

3

CO

3

H (in AcOH, 2 equiv)

CH

3

CN, rt, 5 min

89%

O

O

O

O

O

O

20 (0.5 mol

%)

CH

3

CO

3

H (1 equiv)

20 (0.5 mol

%)

CH

3

CO

3

H (3 equiv)

(22)

−20

°C, CH

3

CN

91%

0

°C, CH

3

CN

88%

O

5

[Mn

II

(bipy)

2

(CF

3

SO

3

)

2

] (0.1 mol

%)

(23)

CH

3

CO

3

H, rt, CH

3

CN, 5 min

94%

5

Oxidation of Saturated Hydrocarbons.

The oxidation of

unactivated C–H bonds to alcohols, acetylated alcohols, and
ketones by peracetic acid has been observed in the presence
of a number of transition metal catalysts including: Ru/C,

40

RuCl

3

,

40,41

Cu(MeCN)

4

BF

4

,

42

Cu(OAc)

2

,

42

Cu(ClO

4

)

2

,

42

and

n

-Bu

4

NVO

3

.

43

Consistent with the putative-free radical mecha-

nism of this reaction, selectivity and degree of oxidation depends
on the substrate, the catalyst, and the specific reaction conditions
employed. A wide range of alkanes are competent substrates, how-
ever, most yield a mixture of oxidized products. The relative reac-
tivity of C–H bonds in this type of oxidation follows the empirical
trend: tertiary > secondary ≫ primary. Oxidation of adamantane
highlights the synthetic potential of this technique when thought-
ful selection of alkane and reaction conditions is made (eq 24).

41

RuCl

3

(1 mol

%)

CH

3

CO

3

H (30% in EtOAc)

+

(24)

89%

9%

TFA/CH

2

Cl

2

(5:1)

70% conversion

OH

OH

Catalytic Oxidation of Primary Alcohols to Carboxy-

lates. Nitroxyl-radical-mediated oxidation is a selective and mild
approach to oxidize primary alcohols to their corresponding car-
boxylate salts in the presence of unprotected secondary alcohols.
It has recently been reported that peracetic acid is an effective
regenerating oxidant for the nitroxyl-radical catalyst 4-AcNH-
TEMPO (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl) in
the presence of cocatalytic sodium bromide (eq 25).

44

Other

A list of General Abbreviations appears on the front Endpapers

PERACETIC ACID

5

common primary oxidants for TEMPO-catalyzed oxidations
include NaOCl, m-CPBA, KHSO

5

, NaClO

2

, and t-BuOCl.

O

O

HO

HO

ONa

O

n

4-AcNH-TEMPO (cat)

NaBr (cat), NaOH

O

O

HO

HO

OH

n

(25)

CH

3

CO

3

H (2 equiv)

5

°C, 10 h, pH 8.2

85%

Oxidation of Catechols. Muconic acids (2,4-hexadienedioic

acids) are readily prepared by treatment of catechols with 4 equiv
of peracetic acid (32% solution in acetic acid) (eq 26).

45

The

reaction mixture is allowed to warm from 0

◦

C to rt and stir for

2–3 d. The scope of the reaction has been demonstrated to include
alkyl- and chloro-substituted catechols in addition to a number of
dimeric catechols. Products commonly include geometric isomers
and lactonized isomers of the target muconic acid.

32% CH

3

CO

3

H (in AcOH, 4 equiv)

OH

OH

HO

2

C

CO

2

H

HO

2

C

HO

2

C

+

5:2

(26)

0

°C to rt, 48 h

70%

Oxidation of Phosphites. The need to synthesize phospho-

rylated organic molecules for biological evaluation has led to the
development of a one-pot chemical phosphorylation protocol.

46

An organic alcohol is first treated with dibenzyl N,N-diisopropyl
phosphoramidite in the presence of 1H-tetrazole and the result-
ing phosphite intermediate is oxidized with peracetic acid or
m

-CPBA to form the corresponding dibenzyl phosphates

(eq 27).

47

This protocol has become a standard method for the syn-

thesis of phosphorylated inositols due to the ease of purification
of dibenzyl phosphates by column chromatography or preparative
HPLC. Deprotection of purified dibenzyl phosphates by catalytic
hydrogenation often yields target organophosphates of sufficient
purity for direct analysis or functionalization.

48,49

(BnO)

2

PNi-Pr

2

, tetrazole, CH

3

CN

O

OMEM

HO

HO

HO

HO

O

OMEM

(BnO)

2

OPO

(BnO)

2

OPO

(BnO)

2

OPO

(BnO)

2

OPO

(27)

CH

3

CO

3

H (32% in AcOH)

Related Reagents.

m

-Chloroperbenzoic Acid; Perbenzoic

Acid.

1.

(a) Swern, D. Organic Peroxides; Wiley: New York, 1971; Vol. II, p 355.
(b) Plesnicar, B. Organic Chemistry; Academic: New York, 1978; Vol.
5C, p 211.

2.

Vogel, E.; Klug, W.; Breuer, A., Org. Synth. 1976, 55, 86.

3.

Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R., Synlett
1990, 533.

4.

Pandell, A. J., J. Org. Chem. 1983, 48, 3908.

5.

Hazards in the Chemical Laboratory

; Luxon, S. G., Ed.; Royal Society

of Chemistry: Cambridge, 1992.

6.

Kirmse, W.; Kornrumpf, B., Angew. Chem., Int. Ed. Engl. 1969, 8, 75.

7.

MacPeek, D. L.; Starcher, P. S.; Phillips, B., J. Am. Chem. Soc. 1959,
81

, 680.

8.

Emmons, W. D.; Pagano, A. S., J. Am. Chem. Soc. 1955, 77, 89.

9.

Crandall, J. K.; Banks, D. B.; Colyer, R. A.; Watkins, R. J.; Arrington,
J. P., J. Org. Chem. 1968, 33, 423.

10.

Shani, A.; Sondheimer, F., J. Am. Chem. Soc. 1967, 89, 6310.

11.

Corey, E. J.; Myers, A. G., J. Am. Chem. Soc. 1985, 107, 5574.

12.

Corey, E. J.; Noyori, R., Tetrahedron Lett. 1970, 311.

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Avoid Skin Contact with All Reagents

6

PERACETIC ACID

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A list of General Abbreviations appears on the front Endpapers