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DMI™ (1,3-Dimethyl-2-imidazolidinone)

1,3-Dimethyl-2-imidazolidinone

Applications detail

High polar and aprotic solvent

Applications

Films, sheets
Raw materials for pharmaceuticals etc.
Agricultural materials
Basic chemical products
Other (chemical products)

Product Overview

DMI™ is an aprotic solvent with high polarity. DMI™ is used in a wide range of fields for its excellent dissolving power, stability, and high quality

Substance

Chemical NameSynonymsCAS No.
1,3-Dimethyl-2-ImidazolidinoneDMEU
Dimethylethyleneurea		80-73-9

Structural Formula

1,3-Dimethyl-2-imidazolidinone 1,3-Dimethyl-2-imidazolidinone

United StatesTSCA:On this inventory, or in compliance with the inventory.
European UnionREACH:Contact us for information.
CanadaDSL:
NDSL:		Not in compliance with the inventory.
AustraliaAICS:On this inventory, or in compliance with the inventory.

Physical properties

DMI™ is easy to handle since boiling point and flash point are high, and freezing point is low.
(Boiling point 222℃、Flash point 120℃(open cup)/ 95℃(closed cup)、Melting point 7.5℃)

Stability

Compared to general aprotic polar solvents, DMI™ is stable even in the presence of acids and alkalis.
DMI™ has excellent resistance to acids and alkalis at high temperature

Solubility

Due to high dielectric constant and dipole moment, DMI™ exhibits high solubility in various inorganic and organic compounds.

Reaction solvents (for synthesis of pharmaceuticals, agricultural chemicals, and polymers), detergents, additives, solvents, surface treatment agents etc.

ItemsSpecificationTest method
APPEARANCECOLORLESS LIQUIDMCI method
COLOR (APHA)≦50MCI method
PURITY (GC%)≧98.0MCI method
REFRACTIVE INDEX ( n25D )1.468 -1.473MCI method
MOISTURE (wt%)≦0.1MCI method

ContainerNet weight
Iron Can18KG
Iron Drum200KG

1. Physical Constants
ItemsUnitsPhysical constants
Molecular weight―114.14
Boiling point (℃)222 (760mmHg)
Melting point(℃)7.5
Specific gravity( d204 )1.06
Refractive index1)( n25D )1.471
Kinetic viscosity1)( mm2/S )1.95 (20℃)
1.43 (40℃)
Surface tension(mN/m)41 (20℃)
Specific heat(J/g･℃)1.80 (adiabatic continuity method, 20℃)
Heat conductivity(kJ/hr･m･℃)0.62 (thermic rays method、25℃)
Vaporization latent heat(kJ/mol)51.9 (=454.7J/g)　
Flash point(℃)120 (Cleveland open method)
95 (Pensky-Martens close method)
Dipole moment1)(D)4.05～4.09
Dielectric constant1)(F/m)37.60 (25℃、1MHz)

1) J. Chem. Eng. Data 21, 150 (‘76)

2. Physical constants compared with other solvents

DMI™ has high values of dielectric constant and dipole moment, and solubility and solvation effect are high compared to similar solvents

Boiling point
(℃)		Melting point
(℃)		Dielectric constant2）
(F/m)		Dipole moment
(D)		Flash point
(℃)		Viscosity3）
(mPa･s)
DMI™2227.537.64.05 - 4.091201.94
DMF153-6137.63.86530.92
DMAC165.5-2037.83.72660.92
NMP220-24324.0981.31.67

2) 25℃, 1MHz
3) DMI™ 25℃, Others 20℃

3. Temperature dependency of dielectric constant, viscosity, density and refractive index
Temperature
(℃)		Dielectric constant4)
(F/m)		Absolute viscosity
(mPa･s)		Density
(kg/m3)		Refractive index
( n25D )
2537.601.9441,0521.471
3535.971.6331,0431.466
4534.431.3931,0341.462
5532.961.2041,025-
7530.350.9381,008-
10027.420.720986-

4) 25℃, 1MHz

4. Rate of moisture adsorption
dmi_pict02
5. Change of water content with drying agent
Drying agentWater content(ppm)
InitialAfter 2.5hrAfter 68hrAfter 116hr
KOH1,5231,6241,6832,211
CaH21,5231,26021696
Zeolite A-3
Pellet1.5mmΦ		1,523200146

Drying agent (10g) was added in DMI™ (50g). After shaking with hand, the water content was measured by the Karl-Fischer Method.

6. Vapor pressure curve
dmi_pict03
7. Freezing point of the mixture with water
dmi_pict04
8.Solubility of inorganic compounds
Inorg.Compd.g/100g(℃)Inorg.Compd.g/100g(℃)
AgNO350(60)LiCl50(70)
AlCl335(20)NaBH411.4(25)
CaCl25(20)NaBr3.2(20)
CaF20.02(20)NaCl0.05(20)
CH3ONa0.02(20)NaCN0.02(20)
CuCl24(20)Na2CO3＜0.01(20)
FeCl3＞50(20)Nal＞200(20)
I2＞150(20)NaOH＜0.1(25)
KCN0.03(20)PCl3＞50(20)
K2CO3＜0.01(20)P2O570(20)
Kl30(60)Mg(ClO4)2＞50(60)
KOH＜0.1(25)S11(100)
KSCN50(80)ZnCl250(60)
LiBr9.3(20)ZnO5(20)
9. Solubility of inorganic compounds
Inorg.Compd.g/100g (℃)
DMI™DMFNMP
CaCl25(20)0.5(r.t.)－
FeCl3＞50(20)＞20(r.t.)－
I2＞150(20)＞25(r.t.)－
KCN0.03(20)0.22(r.t.)－
K2CO3＜0.01(20)0.05(r.t.)－
KOH＜0.1(25)0.1(r.t.)－
LiBr9.3(20)－25.5(25)
NaBH411.4(25)25.5(r.t.)
NaBr3.2(20)－5.5(25)
NaCl0.05(20)＜0.05(r.t.)0.02(25)
NaCN0.02(20)0.76(r.t.)－
Na2CO3＜0.01(20)＜0.05(r.t.)－
NaI＞200(20)14.4(r.t.)28.8(25)
10. Solubility of organic compounds (at room temperature)
Org. Compd.Solubility
Petroleum Benzineinsoluble
Cyclohexane insoluble
Decalinsoluble
Xylenesoluble
Tetralinsoluble
Chloroformsoluble
Trichloroethylene soluble
Methanolsoluble
Isopropyl alcoholsoluble
n-Octyl alcoholsoluble
Ethylene glycolsoluble
Ethyl ethersoluble
Tetrahydrofuransoluble
Org. Compd.Solubility
Acetonesoluble
Acetic acidsoluble
Acetonitrilesoluble
Benzonitrilesoluble
Dimethylformamidesoluble
Ethyl acetatesoluble
Methyl benzoatesoluble
Anilinesoluble
Pyridinesoluble
Quinolinesoluble
Crbon disulfidesoluble
Sulfolanesoluble
Nitrobenzenesoluble
Nitromethanesoluble
11. Solubility of resins
Chemical nameSolubility% (℃)
Epoxy resin＞100(20)
Acrylic styrene resin＞45(20)
Polystyrene＞45(20)
Vinylidene fluoride＞30(20)
Phenol-formaldehyde resin＞20(20)
Polyvinylchloride＞20(20)
Nylon＞5(160)
Polyvinylalcohol＞5(80)
Polyacrylonitrile＞5(70)
Ultem＞3(120)
Chemical nameSolubility% (℃)
Polysulfone＞3(20)
Polyethersulfone＞3(20)
Polymethylmethacrylate＞3(20)
Polyurethane＞1(70)
U-polymer＞1(20)
Noryl＞1(20)
Polyacrylamide＜1(120)
Polyetheretherketone＜1(120)
Polyphenylenesulfide＜1(120)
Polycarbonateswollen(20)
Polytetrafluoroethyleneinsoluble
PolyethyleneInsoluble
12. Explosibility

Lower explosion limit 1.3%
Upper explosion limit 8.4%

13. Solubility parameter

A solubility parameter is calculated as follows:

dmi_pict23

where
ΔH= heat of vaporization (J/mol)
R=gas constant (J/K･mol)
T=absolute temperature (K)
M=molar weight (g/mol)
d=density (Kg/m3)

when the following values are substituted in ①,

ΔH=51,882 (J/mol)
R=8.315 (J/K･mol)
T=298 (K)
M=114.14 (g/mol)
d=1,052 (Kg/m3)

The solubility parameter of DMI™ is obtained as follows:

dmi_pict24
14. Distribution coefficients between organic compounds and water
Org. Compd.Distribution coefficient
(27℃～30℃)
Chloroform2.5
Dichloromethane2.5
1,2-Dichloroethane0.77
1,1,2-Trichlorethylene0.26
Benzene0.22
Toluene0.14
1,1,2-Trichloroethane0.12
Diethylether0.06

Distribution coefficient = conc.of DMI™ in org.layer/conc.of DMI™ in water layer

Stability to acids and alkalines

DMI™ can be used for a wide variety of uses because DMI™ has higher heat stability in the presence of acids and alkalines than general aprotic polar solvents.

Stability in acids (in a stream of N2)

DMI™
Residual ratio (%)		NMP
Residual ratio (%)
0hr12hr0hr12hr
Flake NaOH(3g)/ DMI™ or NMP (30g), 200℃10010010069
Powder K2CO3(3g)/ DMI™ or NMP(30g), 200℃10010010086
10% NaOH(3g)/ DMI™ or NMP (7.5g), 100℃10010010029

Stability in alkalines (in a stream of N2)

DMI™
Residual ratio (%)		NMP
Residual ratio (%)
0hr12hr0hr12hr
50% Sulfuric acid, (15g)/ DMI™ or NMP (30g), 100℃10010010077

1. Solvent for reaction

With its high dielectric constant and solvation effect, DMI™ accelerates anionic nucleophilic reactions, and reactions that place with solvation of cation.
DMI™ is thermally and chemically stable with excellent dissolving power for organic and inorganic compounds.
Since DMI™ is extremely useful as a reaction solvent, it is used in various reactions to synthesize medical drugs and pesticides.

Aldol condensation

As a reaction solvent in the production of benzylidene derivatives that are used as anti-inflammatory agents.

dmi_pict05

Nitric acid esterification

As a reaction solvent in the production of (S)-naproxen-4-nitroxybutyl ester used as anti-inflammatory agents, and analgesics.

dmi_pict06

Alkylation

(1) As a reaction additive in the production of alkyl compounds of γ-butyrolactone.

dmi_pict07

(2) As a reaction additive in the production of substituted acetylene compounds used as pharmaceutical intermediates.

dmi_pict08

Silyl etherification

As a reaction solvent in the production of silyl ether compound used as pharmaceutical intermediates.

dmi_pict09

As a reaction solvent in the production of triazole derivative used as an herbicide.

dmi_pict10

As a reaction solvent to produce tetrafluoroethoxybenzenes used as intermediates for germicides, antibacterial agents, insecticides, and herbicides.

dmi_pict11

DMI™ improves the reactivity with its excellent solubility, cation solvation, and suppresses side reactions because of its high stability at high temperatures and in the presence of alkalis.

  • In the production of polyamides and polyimides, DMI™ accelerates the formation of amide and imide groups to produce high molecular weight polymers.1）
  • Polymers suitable for electronic parts with less ionic impurities can be obtained in the production process of polyphenylene sulfide.2）
  • DMI™ can suppress side reactions in the production process of polyethersulfone to produce high quality polymers.3）
  • DMI™ treatment during film formation of polyimide, stretching of polyether ketone film, and production of polysulfone membrane produces uniform and excellent quality products.4）

1)JP63108027A, JP 05140308A
2)JP63268740A
3)JP0586186A
4)JP61195130A, JP0313314A, JP6219209A

Phenyl ethers

dmi_pict12

Amines

dmi_pict13

Fluorobenzenes

dmi_pict14

Reduction

dmi_pict15

Oxydation

dmi_pict16

Kolbe-Schmitt reaction

dmi_pict17

Self-condensation

dmi_pict18

Dimerization

dmi_pict19

Addition reaction

dmi_pict20

Dehydrating agent

DMI™ reacts with halogenating reagents such as phosgene, oxalyl chloride, and is effective as a dehydrating agent.

dmi_pict21

2. Detergents

DMI™ has strong dissolving power and is used in detergents such as paint peeling agents and photoresist stripping agents.5）

5)JP0715111A, JP06228591A

Paint peeling agents

A patent example for DMI™ used in paint peeling agents of acrylic, melamine, urethane type resins, which have sufficient paint removability and excellent workability.
The results after the evaluation test is shown in the table with number of changes for each of the following, ⊚ when changes are observed in the coating and primer resin; O, when the primer resin peels off by disintegration or swelling; Δ when peeling off is observed by partial dissolution or disintegration or swelling; X when no changes are observed (5 test samples were used)

DetergentsComposition
(wt%)		Temperature
(℃)		Results
◎〇△×
DMI™/EtOH90／1050～1005   
Methylene Chloride10040  32
DMF10050～100  32
DMSO10050～100  41

※Acrylic curable paint with melamine coated on parts of polyolefin resin with primer
(Coating I and coating II have different chemical compositions for the coating and primer resins.)

6）JP2924323B2

Photoresist Stripping Agents

A patent example in which DMI™ has been used for photoresist stripping agents that are not corrosive to silver and silver alloys and has high peelability for photoresist and photoresist deteriorated layers7）

Photoresist Stripping AgentsComposition
（mass%）		Results
Photoresist
Peelability		Photoresist alteration
layer Peelability		Corrosive to
silver alloys
DMI™/2-(2-Aminoethoxy)ethanol70／30◎◎◎
DMI™/Monoethanolamine70／30◎◎×
DMI™/Triethanolamine70／30××◎
DMI™/N,N-Diethanolamine70／30○×◎
DMI™/2-(2-minoethoxy)ethanol/Water60／30／10◎××

※Peelability:◎＝ Eliminable,○＝Slight remaining,×＝ not eliminable

※Corrosive :◎＝Remain the same,○＝Discolored parts occur,
×＝ Discolored ・gloss level variation・stripped membranes parts occur

【Test Method】

The substrate used for evaluation was subject to dry etching and then immersed in a photoresist stripping agent at 70℃ for 10 minutes, and the peelability was evaluated using optical and electron microscopes.

Silver alloy corrosivity: A silver alloy formed on a glass substrate was immersed in a photoresist stripping agent at 70℃ for 10 minutes and evaluated for corrosivity using optical and electron microscopes.

7) WO2005/022268A1

3. Additives

DMI™ is used as an additive for adhesives, rubber processing aids, and electrolytes.

Adhesives

A patent example in which proper shape is retained, bonding duration is retained without decreasing the initial tack, has excellent and powerful adhesiveness that even bonds with coated paper for which adhesion is difficult, and used in the stick adhesive that has polyvinyl pyrrolidone as the main component.8）

 Example1Example2Example3
Adhesive ingredienta）95%95%95%
AdditiveDMI™ 5%ε-Caprolactam 5%None
Bonding strength test resultb）100％90％30％
Hardness test resultc）1.011.510.98

※a)Adhesive composition: 27% of polyvinyl pyrrolidone, 8% of sodium stearate, 50% of water, and 10% of glycerin

※b)Bonding strength test: Breaking rate of paper when high quality papers are stuck together and peeled after 3 days

※c)Hardness: Penetration distance (mm) by a 12.5 g needle in 10 seconds. Smaller the penetration distance, greater the hardness

8)JP11189757A

Rubber Processing Aids

A patent example of use in a modifying agent of rubber processing aids that can avoid deterioration of rebound resilience due to addition of processing aids, and deterioration in processability due to dispersion of carbon black. Evaluation of extrusion processability using a rubber composition according to the ASTM D2230-77A method

DenaturantWeight average
molecular weight of
liquid rubber		Additive amount
of liquid rubbera）		60℃
Repulsiveb）		Wetskid
resistancec）		Extrusion
processability
DMI™6,00010596116
None6,00010555812

a)The amount of liquid rubber added is based on 100 g of SBR

b)The test specimen exposed to the atmosphere at 60℃ was measured according to JIS K-6301

c)Measured using a portable skid tester on the road surface of ASTME-303-74 specifications at 23℃
(manufactured by Stanley UK)

9）JP03281645A

Electrolytes

A patent example showing high specific conductivity and thermal stability, used as a solute precipitation inhibitor for electrolyte in which the solute of diazabicycloalkene carboxylate salt does not precipitate even at low temperatures10）

 Electrolyte
composition(wt%)		Specific conductivity
(30℃,ms/cm)
InitialAfter
the heat
treatment
Example1Solute(25)
γ－Butyrolactone(70)
DMI™ (5)		7.17.2
Example2Solute(20)
γ－Butyrolactone(65)
Ethylene glycol(15)		7.04.9
Example3Solute(10)
γ－Butyrolactone(90)		4.54.5

Solute：Phthalic acid mono-1,5-Diazabicyclo[4.3.0]non-5-ene The heat treatment：150℃，10 hours

dmi_pict22

10)JP097895A

4. Solvent

When DMI™ is used as a solvent in the ink of inkjet printers, print density, drying resistance, and storage stability of the ink are known to improve.11)

 

11)JP04339873A, JP06172690A

5. Surface treatment agent

When the surface of the Teflon, a fluorine resin, is treated using a solution (etching agent) prepared by dissolving sodium, potassium, and lithium metal polyallyl complex dispersion is dissolved in DMI™, the bonding strength of epoxy resin adhesive improves.12）

 

12)JP5484501A

 

All references to the possible uses of our products contained in this brochure are made without any warranty, either express or implied.
Nothing herein shall be construed as a representation that our products are fit for use in manufacturing finished product similar or identical to those products displayed herein or for any other purpose.
Our customers must ultimately decide on the use of our products based on their sole independent judgment without any reliance on this brochure.
Nothing herein shall be construed as permission or as recommendation for uses which might infringe valid patents.
(Including patent applications), whether existing now or in the future, or as extending a license under such valid patents.
Because the conditions and methods of use on the part of our customers are beyond our control, we disclaim any liability incurred in connection with the use of our products.
For the detailed safety information, please refer to Materials Safety Data sheet of DMI™.

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MITSUI FINE CHEMICALS, INC., Advanced Chemicals Division, Personal Care Materials Business Sector