Greener Solvent

Alternatives
Supporting the Advancement of Chemistry
through Sound Environmental, Social &
Fiscal Responsibilities
Alternative Solvents
Increased Safety, Low Peroxides Formation
Reduced Environmental Footprint
2Vot|y|tot..|yJ.c|J..:
yc|cpo:ty| not|y| ot|o.
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Features & Benefts
Ap.ct|c pc|.. sc|vo:t
|osonb|os c|Jo:o |: p|ys|c.| p.cpo.t|os
b.cnc .:J |cJc C.|g:..Js to:J tc bo nc.o sc|Jb|o |:
2Vo|| .|o.o .s c||c.c C.|g:..J .o.go:ts to:J tc bo
|oss sc|Jb|o
|c.ns .: ..oct.cpo .|c| .|t| ..to.
.: bo more easily dried t|.: || c. |V
||n|toJ n|sc|b|||ty |: ..to. (14g/100g .t 23)
|.sy sop...t|c: .:J .occvo.y |.cn ..to. reduces the
waste stream
||g|o. bc|||:g pc|:t (80) ccnp..oJ tc ||
||g|o. .o.ct|c: tonpo..tJ.o reduces overall
reaction time
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2-Methyltetrahydrofuran Cat. No.
A:|yJ.cJs, 990 414247-100ML
c:t.|:s 250 ppn b| 414247-1L
414247-6X1L
414247-2L
414247-4X2L
414247-200L-P2
A:|yJ.cJs, 990 673277-100ML
|:||b|tc.|.oo 673277-12X100ML
673277-1L
673277-200L-P2
ReagentPlus, 995 155810-100ML
c:t.|:s 150400 ppn b| 155810-12X100ML
155810-500ML
155810-4X4L
155810-20L
|c. |o.t v.pc.|..t|c:
Less solvent loss JJ.|:g .o.ct|c: .o| Jx
Saves energy JJ.|:g J|st|||.t|c: .:J .occvo.y
Alternative to Tetrahydrofuran for
organometallic reactions
C.|g:..J
|o|c.n.tsk|| (|o|c.n.tsky)
||t||.t|c:
|yJ.|Jo |oJJct|c:
Vot.|.t.|y.oJ cJp||:g (|ock, St|||o, SJ.Jk|)
Alternative to Dichloromethane for
biphasic reactions
A|ky|.t|c:
An|J.t|c:
|Jc|ocp||||c SJbst|tJt|c: |o.ct|c:
2-Methyltetrahydrofuran (2-MeTHF)
CAS No.: 96-47-9
A Truly Green Alternative to Dichloromethane and Tetrahydrofuran
2Vo|| |s Jo.|voJ |.cn renewable resources sJc| .s cc.:ccbs .:J b.g.sso \|o:
JsoJ .s .: c.g.:cnot.|||c sc|vo:t, 2Vo|| c|o.s bct| occ:cn|c.| .:J o:v|.c:no:t.||y
|.|o:J|y .Jv.:t.gos cvo. ot..|yJ.c|J..:
Green Chemistry
|o .|n c| g.oo: c|on|st.y |s tc .oJJco c|on|c.| .o|.toJ
|np.ct c: |Jn.: |o.|t| .:J v|.tJ.||y o||n|:.to cc:t.n|:.t|c:
c| t|o o:v|.c:no:t t|.cJg| JoJ|c.toJ, sJst.|:.b|o
p.ovo:t|c: p.cg..ns C.oo: c|on|st.y so..c|os |c. .|to.:.t|vo,
o:v|.c:no:t.||y |.|o:J|y .o.ct|c: noJ|. .:J .t t|o s.no
t|no st.|vos tc |:c.o.so .o.ct|c: ..tos .:J |c.o. .o.ct|c:
tonpo..tJ.os
|o g.oo: c|on|st.y cc:copt .pp||os |::cv.t|vo sc|o:t||c
sc|Jt|c:s tc sc|vo o:v|.c:no:t.| |ssJos pcsoJ |: t|o |.bc..tc.y
|.J| A:.st.s, .: c.g.:|c c|on|st .c.k|:g |: t|o O|co c|
|c||Jt|c: |.ovo:t|c: .:J cx|:s .t t|o ||A, .:J 'c|: \..:o.
Jovo|cpoJ t|o Twelve Principles of Green Chemistry |: 1991
|oso p.|:c|p|os c.: bo g.cJpoJ |:tc Reducing Risk .:J
Minimizing the Environmental Footprint.
|
3
Cyclopentyl methyl ether (CPME)
CAS No.: 5614-37-9
Environmentally Friendly Alternative to Tetrahydrofuran,
tert-Butyl methyl ether (MTBE), 1,4 Dioxane and other ether solvents
|V| p.cv|Jos . g.oo: sc|Jt|c: |c. t|cso |cck|:g tc |np.cvo t|o|. c|on|c.| p.ccoss by :ct c:|y
n|:|n|.|:g t|o sc|vo:t ..sto st.o.n, bJt .|sc |np.cvos |.bc..tc.y s.|oty JJo tc |V|s J:|,Jo
ccnpcs|t|c: .||c| .os|sts t|o |c.n.t|c: c| po.cx|Jos
Cyclopentyl methyl ether Cat. No.
A:|yJ.cJs, 999
c:t.|:s 50 ppn b|
675970-100ML
675970-1L
675970-2L
ReagentPlus, 999
c:t.|:s 50 ppn b|
675989-500ML
675989-1L
675989-4L
Nucleophilic reactions
An|Jo sy:t|os|s by t|o .o.ct|c: c| .c|J c||c.|Jo
.|t| .n|:o
S|||y|.t|c: .:J Jos|||y|.t|c:
|o.ct|c: c| ..bc: .:|c: .|t| .|Jo|yJo
|obo:.y|.t|c:
A|ky|.t|c: c| .n|:o
So|oct|vo not|y|.t|c: c| p|o:c|s
b.cn|:.t|c: c| .|cc|c| .|t| |b.
3
SJ||c:y|c||c.|Jo sy:t|os|s by t|o .o.ct|c: c|
sJ||c:|c .c|J .|t| ||
5
Reactions using metals
|o.ct|c: c| kotc:o Js|:g |.b|
4
|o.ct|c: c| .coty|o:os .|t| |(O|)
4
|o.ct|c: Js|:g :bJ|| c. ||t||Jn |||scp.cpy| An|Jo
|.J|c.| cyc||..t|c: c| t.|c||c.c.cot.to Js|:g J c.t
|oJJct|c: c| ot|y| bo:.c.to Js|:g ||t||Jn
A|Jn|:|Jn |yJ.|Jo
|c.n.t|c: c| scJ|Jn J|spo.s|c:
|:t..nc|ocJ|.. o:o .o.ct|c: Js|:g :|
2
Features & Benefts
Vc.o st.b|o t|.: || .:J 2Vo|| (st.b|||.o. .o,J|.oJ)
Resists peroxide formation
Reduces t|o |.o,Jo:cy c| po.cx|Jo tost|:g
|cvo| |yJ.cp|cb|c ot|o. sc|vo:t
|so|J| |: n.:y c.g.:cnot.|||c .o.ct|c:s
Provides better yields .:J ||g|o. so|oct|v|ty cvo. ||
|c.ns .: ..oct.cpo .|c| .|t| ..to.
.: bo nc.o easily dried t|.: || .:J 2Vo||
||n|toJ n|sc|b|||ty |: ..to. (11g/100g .t 23)
|.sy sop...t|c: .:J .occvo.y |.cn ..to. reduces the waste
stream
||g|o. bc|||:g pc|:t (106) ccnp..oJ tc || .:J
2Vo||
||g|o. .o.ct|c: tonpo..tJ.o reduces overall
reaction time
|c. |o.t v.pc.|..t|c:
Less solvent loss JJ.|:g .o.ct|c: .o|Jx
Saves energy JJ.|:g J|st|||.t|c: .:J .occvo.y
CPME applications
Higher optical purity or selectivity were observed
Asynnot.|c V|c|.o| A|ky|.t|c:
V|c|.o| .JJ|t|c: c| |
2
J||
A|ky|.t|c: c| c||..| .n|Jo
C|yccs|J.t|c:
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4
|yJ.cs||y|.t|c: by |J c.t
CPME is a proven alternative to THF,
providing better yields and higher
selectivity.
O|
3
3
Check out the new
Spec Comparison page
to fnd the perfect Sigma-Aldrich
solvent for your application.
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Properties CPME 2-MeTHF THF Ether DCM 1,4-Dioxane MTBE
Density (20 C) [g/cm3] 0.86 0.86 089 01 132 103 04
Dielectric constant (25 C) 4.76 6.97 58 419 893 222
Boiling point [C] 106 80 65 346 398 101 55
Heat of Vaporization
(bp) [Kcal/kg]
69.2 87.1 981 861 805 986 81
Solubility of Solvent in Water (23 C) 1.1 14 |:|:|to 65 13 |:|:|to 48
Solubility of Water in Solvent (23 C) 0.3 4.4 |:|:|to 12 02 |:|:|to 15
Azeotropic temperature with Water [C] 83 89 64 34 39 88 52
Flash point [C] 1 11.1 142 45 12 28
Explosion range [vol%]
Lower / Upper limit
1.1% / 9.9% 184 / 118 185 / 48 14 / 22 2 / 22 16 / 151
Physical Properties of Solvents
Peroxide Formation of Ether Solvent
Conditions
20 n| c| o.c| s.np|o |: . b.c.: bctt|o
(c.p.c|ty c| 65 n|)
Stc.oJ .t .ccn tonpo..tJ.o, |: . J..k p|.co
.:J |: t|o p.oso:co c| .|.
CPME is a product of Zeon Corporation with approval by Toxic
Substances Control Act (TSCA) and European List of Notifed
Chemical Substances (ELINCS).
0
50
100
150
200
250
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Days (x)
P
e
r
o
x
i
d
e

w
t
.

p
p
m
Y = 15.277e
0.0962x
+ 12.9 ppm
Y = 0.8218x + 15.9 ppm
Y = 0.1397x + 4.5 ppm
Rate of Peroxide Formation by days (x)
CPME Stabilized 683 days to reach 100 ppm
THF Stabilized 102 days to reach 100 ppm
THF 19 days to reach 100 ppm
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326510361
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