MTHP

New innovative reaction solvent "MTHP"
leads to environmental friendly processes.

Features

1.High Hydrophobicity
  • simplifies your organic process
  • reduce wastewater and emissions
2.High Safety
  • oxidaizing slower
3.High Stability
  • stable in acids, bases and Lewis acids
4.High Solvency Power
  • similar to THF
  • dissolve inorganic salts
5.Various Usage in Organic Reactions
  • stable in organometallic reagents
  • higher boiling point than other ethers

Applications

Organic Reactions
  • Esterification, acetalification by azeotropic dehydration
  • Esterification with acid chloride
  • Grignard reaction / Coupling reaction
  • Reduction with metals (LAH, NaBH4, etc.)
  • Reaction with n-BuLi
  • Hydrogenation
Extractions
Crystallizations
Coatings
Anionic polymerizations / Cationic polymerizations
High level of vinyl content

General Information / Quality

Chemical name
4-Methyltetrahydropyran
Molecular weight
100.16 (C6H12O)
CAS No.
4717-96-8
Purity (%GC)
>99.0
Water content (ppm)
<200
Additive
BHT 20ppm
Packages
  • Drum（160kg）
  • Can（14kg）
  • ISO container（bulk）
  • Tank truck

Physical Properties

 
MTHP
THF
2MTHF
CPME
Et2O
1,4-Dioxane
B.P.
（℃）		 M.P.
（℃）		 Specific Gravity
（20℃,g/cm3）		 Viscosity
（cP）		 Flash Point
（℃）		 Solubility in Water
（wt%）		 Water Solubility
（wt%）		 Azeotropic Point
（℃）(H2O ratio)		 SP Value*
(cal/cm3)^0.5
105 -92 0.86 0.78 6.5 1.5 1.4 85(19wt%) 9.0
65 -109 0.89 0.55 -15 ∞ ∞ 64(6.0wt%) 9.5
80 -136 0.85 0.60 -11 14 4.4 71(11wt%) 8.9
106 -140 0.86 0.55 -1 1.1 0.3 83(16wt%) 8.4
34.6 -116 0.70 0.24 -45 6.5 1.2 34(1.3wt%) 7.6
101 12 1.04 1.30 11 ∞ ∞ 88(18wt%) 10.0
*Calculated according to “Hansen solubility parameters a user’s handbook 2nd edition, CRC Press, ISBN: 0-8493-7248-8”

Japanese Domestic Regulation

Fire Service Act
Class-4 No.1 petroleums Not water-soluble
Chemical Substances Control Act
5-6997
Industrial Safety and Health Act
8-(4)-1740
Poisonous and Deleterious Substances, PRTR
Not listed

Safety Data

 
LD50(oral)
Eye damage / irritation
Skin corrosion / irritation
Ames test
Chromosome aberration test
Mutation
Repeated-dose toxicity
Biodegradability
Ecotoxicity Fish
Ecotoxicity Daphnia magna
Ecotoxicity Algae growth inhibition
MTHP THF(1) 2MTHF(1) CPME
1000-2000mg/kg(2) 1650mg/kg 300-2000mg/kg 1000-2000mg/kg
Irritation Corrosive Corrosive Irritation
Corrosive Mild irritation Mild irritation Irritation
Negative Negative Negative Negative
Negative(3) Negative(4) Negative(5) Negative
No data Negative Negative No data
NOEL=120mg/kg/day(6) NOAEL=111.3mg/kg/day(6) NOAEL=26mg/kg/day(7) NOAEL=150mg/kg/day
Persistent nature Biodegradable Persistent nature Persistent nature
LC50(96hr)>110mg/L LC50(96hr)=2160mg/L LC50(96hr)>100mg/L LC50(96hr)>220mg/L
>100mg/L 3485mg/L >139mg/L 35mg/L
EC50(72hr)>100mg/L EC0(8day)=225mg/L EC50(72hr)>104mg/L EC50(72hr)>100mg/L
  1. Cited by ECHA’s homepage
  2. In-house testing
  3. Species : Chinese Hamster Lung cells
  4. Species : Chinese Hamster Ovary cells
  5. Species : lymphocytes; peripheral human
  6. 28 days oral toxicity study on rats
  7. three-month oral toxicity study on rats

High Hydrophobicity

MTHP simplifies the process, reduces wastewater and emissions

Stability

<Stability in Acid and Bases>

MTHP can be used in acidic & basic conditions.

  • Esterification and acetalization with acid catalyst
  • Cationic polymerization with acid catalyst
  • Reduction with LAH (at the workup, low pH)
  • Esterification using acid chloride

<Stability in Lewis Acid>

<Stability of Alkyl Lithium>

Test Conditions
  • 1.6M　n-BuLi/Hexane 30mL
  • Solvent 30mL
  • Temp. ; 50℃

Reaction rate and Half-life period

  K1 Half-life period
MTHP 0.27 2.4hr
THF 4.91 0.1hr
2MTHF 0.69 0.8hr
CPME 0.13 5.6hr

<Stability to Autoxidation>

Test Method
  • Under air at 25℃, without stabilizer
  • POV was measured by Iodometry method

Solubility

<Solubility of Inorganic Salts>

<Solubility of Resins>

Resins MTHP THF 2MTHF CPME
ABS ○ ○ ○ ○
Acrylic resin ○ ○ ○ ○
Polystyrene ○ ○ ○ ○
Vinyl chloride ○ ○ ○ △
Polycarbonate △ ○ ○ △
Fluoro rubber △ △ ○ △
Styrene-butadiene rubber △ △ ○ △
Polyurethane △ △ ○ △
Butyl rubber △ × △ ×
Nylon-6 × × × ×
Phenol resin × × × ×
Polypropylene × × × ×
High density polyethylene × × × ×
Low density polyethylene × × × ×
Teflon × × × ×
Test Method
  • Test panel of resin was dipped into each solvent at 50℃ for 7 days.
  • After dipping, size was measured and increasing volume rate was calculated.
  • Evaluation of volume increase.
    ○
    more than 100%, dissolved
    △
    from 30% to 100%
    ×
    less than 30%

Reaction Examples

<Grignard reaction>

  MTHP 2MTHF THF*
Yield
In Org. Layer		 83.9 70.5 0.0
Yield
In Aq. Layer
= Loss !		 0.9 2.5
* Grignard reagent was not generated in THF

<LAH reduction>

MTHP enables be reduction of the loss of products and the use of solvents.
  Loss in Aq.
Layer 1		 Loss in Aq.
Layer 2		 Total Yield Solvent
recovery
MTHP Prod. 2%
Solv. 2%		 Prod. 5%
Solv. 2%		 82% MTHP 85%
THF Prod. 15%
Solv. 35%		 Prod. 5%
Solv. 3%		 68% THF 60%
Ester 87%