Cyclopentyl methyl ether (CPME)
Cyclopentyl methyl ether (CPME) is a totally new hydrophobic ether solvent, which was established out of ZEON's unique synthetic technology and C5 raw materials.
Unlike other common ether solvents, CPME has unique excellent properties and is widely applicable as a replacement for Tetrahydrofuran (THF), Methyl Tert-Butyl Ether (MTBE), Dioxane and other existing ether solvents.

CAS:
TSCA:
ELINCS
Japan:		 5614-37-9
Approved
Approved
3-4548


Novel hydrophobic ether solvent
Cyclopentyl methyl ether (CPME)

Benefits >>
Applications >>
Physical Properties >>
Comparison of CPME with MeTHF and THF >>
Physical property Comparison of CPME versus MeTHF and THF >>
Organic Processes with CPME vs. THF >>
Peroxide Formation of Ether Solvents >>
Product Specifications >>
Packings >>
Cautions >>


Benefits
HIGH HYDROPHOBICITY
Easy separation and recovery from water, reducing emissions and wastewater Wide applicability as a reaction, extraction and crystallization solvent, giving simple and One-pot syntheses
WIDE LIQUIDITY RANGE
Wide applications from lower to higher temperature, accelerating reaction rate
LOW HEAT OF VAPORIZATION
Saving energy for distillation and recovery
RESIST PEROXIDE FORMATION
Low exothermic decomposition energy of solvent containing it's peroxides
NARROW EXPLOSION AREA
RELATIVELY STABLE TO ACIDS OR BASES
EASY DRYING


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Applications
REACTIONS
Grignard Reaction, Suzuki Coupling, Buchwald Amination, Metal Reductions (NaBH4, LiAlH4, i-Bu2AlH), Reactions with n-BuLi, Reactions with Lewis Acid, Friedel Crafts Reactions
EXTRACTIONS
CRYSTALLIZATIONS
POLYMERIZATIONS
COATINGS


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Physical Properties
  CPME THF MeTHF Diethyl ether Dioxane MTBE
Density (20°C)[g/cm3] 0.86 0.89 0.85 0.71 1.03 0.74
Vapor specific gravity (air = 1) 3.45 2.49 2.97 2.56 3.3 3.03
Boiling point [°C] 106 65 80 34.6 101 55
Melting point [°C] <-140 -108.5 -136 -116.3 11.8 -108.7
Viscosity (20°C)[cP] 0.55 0.55 0.6
(25°C)		 0.2448 1.31 0.35
Surface tension (20°C)[mN/m] 25.17 26.4 Unknown 17.3 33.74 19.8
Heat of vaporization (boiling point)[Kcal/kg] 69.2 98.1 89.7 86.08 98.6 81.7
Specific heat (20°C)[Kcal/kg・K] 0.4346 0.469 Unknown 0.5385 0.41 0.51
Refractive index (20°C) 1.4189 1.407 1.406 1.353 1.422 1.369
Solubility parameter [cal/ml] 8.4 9.5 8.52 7.4 Unknown Unknown
Dielectric constant (25°C) 4.76 7.58 7 4.197 2.227 2.6
Dipole moment [D] 1.27
(calcd.)		 1.7 Unknown 1.12 0.45 1.4
Azeotropic point with water [°C] 83(a) 64 71(b) 34.2 87.8 52.9(c)
Solubility in water (23°C)[g/100g] 1.1 ∞ 14 6.5 ∞ 4.8
Solubility of water in the solvent (23°C)[g/100g] 0.3 ∞ 4.4 1.2 ∞ 1.4
Flash point [°C] -1 -14.5 -11 -45 12 -28
Ignition point [°C] 180 205 270 180
～190		 180 224
LogPow 1.59 0.47 Unknown 0.89 -0.42 0.94
Explosion range [vol%] (Lower limit) 1.1 1.84 1.5 1.85 2 1.6
Explosion range [vol%] (Upper limit) 9.9 11.8 8.9 48 22 8.4

azeotrope(wt%)    
(a) composition= CPME:83.7 H2O:16.3
(b) composition= MeTHF:89.4 H2O:10.6
(c) composition= MTBE:96.5 H2O:3.5


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Comparison of CPME with MeTHF and THF
  excellent good poor
  CPME MeTHF THF
Recovery rate from water[%][g/cm3] 90 70 60
Waste rate (1 - recovery rate)[%] 10 30 40
Explosive Peroxide formation SLow high high
Stability to acid strong weak weak
Solubility in water[g/100g-water] 1.1 14 ∝
Boiling Point[°C] 106 80 65
Flash Point[°C] -1 -11 -14.5
Vaporization Energy (at bp)[Kcal/kg] 69.2 89.7 98.1



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Physical property Comparison of CPME versus MeTHF and THF
  CPME MeTHF THF
CAS number
Molecular weight		 5614-37-9
100.16		 96-47-9
86.13		 109-99-9
72.11
(1) Solubility of solvent in water
(23°C) [g/100g]
Solubility of water in solvent
(23°C) [g/100g]		 1.1

0.3

 14

4.4

 Indinite

Indinite
(2) Flash point [°C]
Peroxide formation
Explosion range
[vol%] (Lower / Upper limit)		 -1
slower
1.1 / 9.9

 -11
faster
1.5 / 8.9

 -14.5
faster
1.84 / 11.8
(3) Stability to acids more stable less stable unstable
(4) Boiling point [°C]
Melting point [°C]
Latent heat of vaporization
(bp) [Kcal/kg]		 106
<-140
69.2

 80
-136
89.7

 66
-108.5
98.0
(5) Azeotropic temperature with water
[°C]
Azeotropic composition
(solvent / water) [wt%]		 83

83.7/16.3

 71

89.4/10.6

 64

93.3/6.7
(6) Solubility parameter[cal/ml]
Dielectric constant(25°C)
Dipole moment [D]		 8.4
4.76
1.27		 8.52
7.0
-		 9.15
7.4
1.7
(1)CPME has extremely low miscibility with water.
- You can easily make clear phase separation.
- You can use CPME as a extraction solvent as well as reaction.
- You can reduce variable and fixed cost by telescoping and one-pot reaction with CPME.
- You can recover greater than 95% of CPME.
(2)CPME has higher flash point and lower peroxide formation.
- You can use CPME in filtration.
- The peroxide formation of CPME is much slower than that of MeTHF.
(3)CPME has more stability to acids.
- You can use CPME in acidic conditions such as 4M-HCl in CPME solution.
(4)CPME has higher boiling point and lower vaporization energy.
- You can accelerate reaction and save reaction time.
- You can use CPME as a crystallization solvent as well as reaction and extraction.
(5)CPME has higher efficiency for azeotropic dehydration.
- You can easily dry CPME by azeotropic distillation.
(6)CPME has medium polarity.
- You can use CPME as a crystallization solvent as well as reaction and extraction.


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Organic Processes with CPME vs. THF
CPME simplifies processes, reduces wastewater and emissions.


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Peroxide Formation of Ether Solvents



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Product Specifications
purity(GC) 99.9% min
Water 100ppm max
Color(Hazen No) 10 max
Peroxide 50 mgeq/kg max


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Packings
170kg Drum, 16kg Can


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Cautions
  • The information contained herein is believed to be reliable, but no representations, guarantees or warranties of any kind are made as to its accuracy, stability for particular applications or results to be obtained.
  • Please read the Material Safety Data Sheet (MSDS) carefully prior to handling.
  • This product was developed for the applications herein. In case of other applications, please handle under your confirmation of safety for the applications, or please talk to Zeon Corporation beforehand.





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