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110-71-4

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110-71-4 Usage

Synthesis

1,2-Dimethoxyethane is derived from the reaction of ethylene glycol monomethyl ether with sodium metal and methyl chloride. The ethylene glycol monomethyl ether and the metal sodium were refluxed together until the metal sodium was completely reacted, the temperature was lowered to 45° C., and methyl chloride was introduced. After the reaction is completed, fractional distillation is performed to collect fractions at 84-85.5°C to obtain 1,2-Dimethoxyethane.

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 110-71-4 differently. You can refer to the following data:
1. Solvent commonly employed in organometallic reactions,1 particularly organolithium reactions.2 May also function as a ligand.3
2. Monoglyme is used in the electrolyte solutions for lithium batteries.
3. 1,2-Dimethoxyethane is widely used as a solvent for electrolyte of lithium batteries, polysilicones, oligo- and polysaccharides. It plays an important role in Grignard reactions, Suzuki reactions and Stille couplings in organometallic chemistry and in pharmaceutical synthesis. It is a higher boiling point solvent and is used as an alternative to diethyl ether and tetrahydrofuran. It is used for the etching of synthetic polymers like polytetrafluoroethylene and other fluoropolymers with alkali metal dispersions.

Definition

ChEBI: A diether that is the 1,2-dimethyl ether of ethane-1,2-diol.

General Description

A liquid with a sharp odor. Less dense than water. Flash point 34°F. Mildly toxic by ingestion and inhalation. Severely irritates skin and eyes. Vapors heavier than air. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

When the solvent, 1,2-Dimethoxyethane, was poured into a funnel previously used to introduce the lithium aluminum hydride, a fire ignited the funnel, [MCA Case History 1182(1966)].

Hazard

Moderate fire risk.

Health Hazard

If ingested causes nausea, vomiting, cramps, weakness, coma.

Fire Hazard

Behavior in Fire: Containers may explode in fires.

Flammability and Explosibility

Highlyflammable

Safety Profile

An experimental teratogen. Other experimental reproductive effects. Readdy forms an explosive peroxide. A very dangerous fire hazard when exposed to heat, flame, or oxidzers. Mixture with lithium tetrahydroaluminate may ignite orexplode if heated. When heated to decomposition it emits acrid smoke and fumes. See also GLYCOL ETHERS.

Purification Methods

Traces of water and acidic materials have been removed from it by refluxing with Na, K or CaH2, decanting and distilling from Na, K, CaH2 or LiAlH4. The reaction has been speeded up by using vigorous high-speed stirring with molten potassium. For virtually complete elimination of water, 1,2-dimethoxyethane has been dried with Na-K alloy until a characteristic blue colour is formed in the solvent at Dry-ice/cellosolve temperatures: the solvent is kept with the alloy until distilled for use [Ward J Am Chem Soc 83 1296 1961]. Alternatively, glyme, refluxed with benzophenone and Na-K, is dry enough if, on distillation, it gives a blue colour of the ketyl immediately on addition to benzophenone and sodium [Ayscough & Wilson J Chem Soc 5412 1963]. It has also been purified by distillation under N2 from sodium benzophenone ketyl (see above). [Beilstein 1 IV 2376.]

Check Digit Verification of cas no

The CAS Registry Mumber 110-71-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 110-71:
(5*1)+(4*1)+(3*0)+(2*7)+(1*1)=24
24 % 10 = 4
So 110-71-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3

110-71-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A12986)  1,2-Dimethoxyethane, 99+%, stab. with BHT   

  • 110-71-4

  • 100ml

  • 298.0CNY

  • Detail
  • Alfa Aesar

  • (A12986)  1,2-Dimethoxyethane, 99+%, stab. with BHT   

  • 110-71-4

  • 500ml

  • 514.0CNY

  • Detail
  • Alfa Aesar

  • (A12986)  1,2-Dimethoxyethane, 99+%, stab. with BHT   

  • 110-71-4

  • 2500ml

  • 2057.0CNY

  • Detail
  • Sigma-Aldrich

  • (72405)  1,2-Dimethoxyethane  analytical standard

  • 110-71-4

  • 72405-1ML-F

  • 356.85CNY

  • Detail
  • Sigma-Aldrich

  • (72405)  1,2-Dimethoxyethane  analytical standard

  • 110-71-4

  • 72405-5ML-F

  • 1,409.85CNY

  • Detail
  • Sigma-Aldrich

  • (259527)  1,2-Dimethoxyethane  anhydrous, 99.5%, inhibitor-free

  • 110-71-4

  • 259527-100ML

  • 855.27CNY

  • Detail
  • Sigma-Aldrich

  • (259527)  1,2-Dimethoxyethane  anhydrous, 99.5%, inhibitor-free

  • 110-71-4

  • 259527-250ML

  • 1,389.96CNY

  • Detail
  • Sigma-Aldrich

  • (259527)  1,2-Dimethoxyethane  anhydrous, 99.5%, inhibitor-free

  • 110-71-4

  • 259527-1L

  • 1,574.82CNY

  • Detail
  • Sigma-Aldrich

  • (259527)  1,2-Dimethoxyethane  anhydrous, 99.5%, inhibitor-free

  • 110-71-4

  • 259527-12X100ML

  • 8,669.70CNY

  • Detail
  • Sigma-Aldrich

  • (259527)  1,2-Dimethoxyethane  anhydrous, 99.5%, inhibitor-free

  • 110-71-4

  • 259527-2L

  • 2,548.26CNY

  • Detail
  • Sigma-Aldrich

  • (259527)  1,2-Dimethoxyethane  anhydrous, 99.5%, inhibitor-free

  • 110-71-4

  • 259527-6X1L

  • 7,950.15CNY

  • Detail
  • Sigma-Aldrich

  • (E27408)  1,2-Dimethoxyethane  ReagentPlus®, ≥99%, inhibitor-free

  • 110-71-4

  • E27408-100ML

  • 833.04CNY

  • Detail

110-71-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-dimethoxyethane

1.2 Other means of identification

Product number -
Other names 1,2-dimethyloxyethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Processing aids, not otherwise listed
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:110-71-4 SDS

110-71-4Synthetic route

methylene chloride
74-87-3

methylene chloride

2-(2-methoxyethoxy)ethyl alcohol
111-77-3

2-(2-methoxyethoxy)ethyl alcohol

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With sodium hydroxide In water at 60℃;99.8%
Dimethyl ether
115-10-6

Dimethyl ether

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With MCM-22 In 1,4-dioxane at 50℃; under 750.075 Torr; Pressure; Reagent/catalyst; Temperature; Inert atmosphere;
With hydrogen-type mordenite molecular sieve, Si:Al ratio 4:1 at 200℃; under 60006 Torr; Temperature; Pressure; Reagent/catalyst; Autoclave;
2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With sodium Behandeln des Reaktionsgemisches mit Methylchlorid, zuletzt bei 60grad;
With sulfuric acid
With H-type ZSM-5(SiO2/Al2O3=280) at 180℃; for 11h;
With sulfuric acid
With sodium Behandeln des Reaktionsgemisches mit Dimethylsulfat, zuletzt bei 85-90grad;
methanol
67-56-1

methanol

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With MCM-22 zeolite at 50℃; under 750.075 Torr; Reagent/catalyst; Pressure; Temperature;
2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

ethylene glycol
107-21-1

ethylene glycol

Conditions
ConditionsYield
With H-β molecular sieve catalyst at 70℃; under 3750.38 Torr; Reagent/catalyst; Temperature; Pressure; Inert atmosphere;
methanol
67-56-1

methanol

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

ethylene glycol
107-21-1

ethylene glycol

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With NAFION 1100 EW Polymer (H+ form) at 200℃; under 36201.3 - 51716.2 Torr; for 82h;
Dimethyl ether
115-10-6

Dimethyl ether

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

A

1,4-dioxane
123-91-1

1,4-dioxane

B

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With sulfonated styrene-divinylbenzene copolymer acidic cation exchange resin (D005) at 130℃; under 37503.8 Torr; Reagent/catalyst; Autoclave;
1,1-dichloroethane
75-34-3

1,1-dichloroethane

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
In methanol73%
oxirane
75-21-8

oxirane

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

methyl ester (3-hydroxy) propionic acid
6149-41-3

methyl ester (3-hydroxy) propionic acid

C

ethylene glycol
107-21-1

ethylene glycol

D

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium tetracarbonylcobaltate at 75℃; under 27752.8 Torr; for 10h; Autoclave;
carbon monoxide
201230-82-2

carbon monoxide

A

methanol
67-56-1

methanol

B

propan-1-ol
71-23-8

propan-1-ol

C

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

D

methane
34557-54-5

methane

E

ethanol
64-17-5

ethanol

F

ethane
74-84-0

ethane

G

2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

H

Methyl formate
107-31-3

Methyl formate

I

acetaldehyde
75-07-0

acetaldehyde

J

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In carbon dioxide; nitrogen at 300℃; under 38787.1 Torr; for 20h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 22h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 22h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 20h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 20h; Conversion of starting material;
ethylene glycol
107-21-1

ethylene glycol

methyl iodide
74-88-4

methyl iodide

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With iron(III) perchlorate In dichloromethane at 20℃; for 1.5h;90%
methanol
67-56-1

methanol

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With alumina at 249.84℃; under 757.576 Torr; Kinetics; Reagent/catalyst;
methylene chloride
74-87-3

methylene chloride

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With sodium hydroxide at 90℃; for 15h;
Dimethyl ether
115-10-6

Dimethyl ether

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

1,2,3-trimethoxy glycerol ether
20637-49-4

1,2,3-trimethoxy glycerol ether

Conditions
ConditionsYield
With di-tert-butyl peroxide at 135℃; Autoclave;
Dimethyl ether
115-10-6

Dimethyl ether

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

diethylene glycol dimethyl ether
111-96-6

diethylene glycol dimethyl ether

C

1,2,3-trimethoxy glycerol ether
20637-49-4

1,2,3-trimethoxy glycerol ether

Conditions
ConditionsYield
With di-tert-butyl peroxide at 150℃; for 4h; Temperature; Autoclave;
methanol
67-56-1

methanol

ethylene glycol
107-21-1

ethylene glycol

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

Conditions
ConditionsYield
With phosphorus pentoxide 1.) reflux, 2 h, 2.) a) from 150 deg C to 175 deg C, 5 h, b) from 130 deg C to 160 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
With NAFION 1100 EW Polymer (H+ form) at 198 - 200℃; under 48096 Torr; for 5h;
With SAPO-34 zeolite In water at 209.84℃; under 2250.23 Torr; for 1.66667h; Catalytic behavior; Reagent/catalyst; Time; Flow reactor; Inert atmosphere; Green chemistry;
potassium
7440-09-7

potassium

ytterbium

ytterbium

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

potassium bis({8}annulene)ytterbate(III)
92670-64-9

potassium bis({8}annulene)ytterbate(III)

Conditions
ConditionsYield
With cyclooctatetraen In ammonia NH3 (liquid); cyclooctatetraene is added to a dry ice/2-propanol cooled liquid NH3 soln. of Yb metal and of K metal;; evapn.;;A n/a
B 86%
2-(2-methoxyethoxy)ethyl alcohol
111-77-3

2-(2-methoxyethoxy)ethyl alcohol

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

Triethylene glycol dimethyl ether
112-49-2

Triethylene glycol dimethyl ether

C

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

D

diethylene glycol dimethyl ether
111-96-6

diethylene glycol dimethyl ether

Conditions
ConditionsYield
5%-palladium/activated carbon; nickel at 220℃; under 2250.23 Torr; for 10h;A 75%
B 2%
C 10%
D 11%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With water
tert-butyl methyl ether
1634-04-4

tert-butyl methyl ether

A

methanol
67-56-1

methanol

B

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

C

Isobutane
75-28-5

Isobutane

D

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
HF/Attapulgite at 140 - 150℃; under 1535.79 Torr; for 120 - 384h; Product distribution / selectivity; Gas phase;
mixed metal oxide catalyst (Ce 2.64 wt.percent; Zr 64.12 wt.percent; S 0.69 wt.percent) at 140 - 150℃; under 1535.79 Torr; for 120 - 744h; Product distribution / selectivity; Gas phase;
mixed metal oxide catalyst (W 18.1 wt.percent; Zr 54.3 wt.percent; Fe 0.58 wt.percent; S 0.69 wt.percent) calcined to 500 C in flowing air for 3 h at 140 - 150℃; under 1535.79 Torr; for 24 - 504h; Product distribution / selectivity; Gas phase;
oxirane
75-21-8

oxirane

boron fluoride dimethyl etherate

boron fluoride dimethyl etherate

3-methoxypropylbenzene
2046-33-5

3-methoxypropylbenzene

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
In water
oxirane
75-21-8

oxirane

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

C

methyl ester (3-hydroxy) propionic acid
6149-41-3

methyl ester (3-hydroxy) propionic acid

D

ethylene glycol
107-21-1

ethylene glycol

Conditions
ConditionsYield
With immobilization of carbonylcobalt catalyst by poly(4-vinylpyridine)(P4VP) In tetrahydrofuran at 75℃; under 22502.3 Torr; for 15h;
With dicobalt octacarbonyl; triphenylphosphine In tetrahydrofuran at 75℃; under 22502.3 Torr; for 15h;
oxirane
75-21-8

oxirane

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

methyl ester (3-hydroxy) propionic acid
6149-41-3

methyl ester (3-hydroxy) propionic acid

C

ethylene glycol
107-21-1

ethylene glycol

Conditions
ConditionsYield
With immobilization of carbonylcobalt catalyst by poly(4-vinylpyridine)(P4VP) In tetrahydrofuran at 75℃; under 22502.3 Torr; for 15h;
oxirane
75-21-8

oxirane

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

C

methyl ester (3-hydroxy) propionic acid
6149-41-3

methyl ester (3-hydroxy) propionic acid

Conditions
ConditionsYield
With immobilization of carbonylcobalt catalyst by poly(4-vinylpyridine)(P4VP) In tetrahydrofuran at 75℃; under 22502.3 Torr; for 15h;
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With diethyl ether; copper
With diethyl ether; sodium
bis(bis(trimethylsilyl)amino)ytterbium * 1,2-dimethoxyethane
90669-97-9

bis(bis(trimethylsilyl)amino)ytterbium * 1,2-dimethoxyethane

A

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

B

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

C

ytterbium(III) chloride
10361-91-8

ytterbium(III) chloride

D

ammonium chloride

ammonium chloride

Conditions
ConditionsYield
With hydrogenchloride In toluene condensing gaseous HCl with liquid nitrogen in an ampul containing toluene solution of (((CH3)3Si)2N)2Yb*CH3O(CH2)2OCH3; warming to room temperature; removing volatile compounds ((CH3)3SiCl, DME) by vac. condensation; vac. sublimation at 100°C (1E-2 mm): NH4Cl;;A 100%
B 90%
C 100%
D 92%
2-Methoxyethoxymethyl chloride
3970-21-6

2-Methoxyethoxymethyl chloride

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); poly(phenylsilane) In benzene-d6 at 82 - 85℃; for 3h; sealed;96 % Spectr.
Mo[C3(C(CH3)3)2][OC(CH3)(CF3)2]2((CH3OCH2)2)

Mo[C3(C(CH3)3)2][OC(CH3)(CF3)2]2((CH3OCH2)2)

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

Mo[C3(C(CH3)3)2][OC(CH3)(CF3)2]2

Mo[C3(C(CH3)3)2][OC(CH3)(CF3)2]2

Conditions
ConditionsYield
In (2)H8-toluene under N2, dissolution in toluene-d8; not isolated; detected by NMR;
praseodymium heptakis[tris(pentafluorophenyl)germanyl]dimercurate*3(dimethoxyethane)

praseodymium heptakis[tris(pentafluorophenyl)germanyl]dimercurate*3(dimethoxyethane)

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

praseodymium(III) chloride
10361-79-2

praseodymium(III) chloride

C

tris(pentafuorophenyl)germane
42371-50-6

tris(pentafuorophenyl)germane

D

Chloro[tris(perfluorophenyl)]-germane
1259-89-8

Chloro[tris(perfluorophenyl)]-germane

E

mercury

mercury

Conditions
ConditionsYield
With HCl In tetrahydrofuran excess of HCl; in evacuated ampul maintained overnight at 20°C, heated 2 h up to 70°C; organic layer decanted; gas-liq. chromy.;A 97.5%
B 89%
C 94.5%
D 72.2%
E 65.5%
2-Methoxyethoxymethyl chloride
3970-21-6

2-Methoxyethoxymethyl chloride

A

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

B

bis(chloromethoxy)methane
15112-21-7

bis(chloromethoxy)methane

C

Dimethyl ether
115-10-6

Dimethyl ether

D

1,2-Diiodoethane
624-73-7

1,2-Diiodoethane

Conditions
ConditionsYield
Stage #1: 2-Methoxyethoxymethyl chloride With niobium(V) iodide In dichloromethane; chloroform-d8 at 20℃; for 48h; Inert atmosphere;
Stage #2: With water In dichloromethane; chloroform-d8 Inert atmosphere;
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

1,2-dimethoxy-ethane; compound with trichloroborane

1,2-dimethoxy-ethane; compound with trichloroborane

Conditions
ConditionsYield
With boron trichloride at -78 - 0℃;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

methyl 3-benzyloxy-6-(1-pyrrolidinyl)picolinate

methyl 3-benzyloxy-6-(1-pyrrolidinyl)picolinate

methyl 3-hydroxy-6-(1-pyrrolidinyl)picolinate

methyl 3-hydroxy-6-(1-pyrrolidinyl)picolinate

Conditions
ConditionsYield
In methanol; palladium-carbon100%
In methanol; palladium-carbon100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

ytterbium

ytterbium

bis(hexamethyldisilylamido)mercury(II)

bis(hexamethyldisilylamido)mercury(II)

A

bis(bis(trimethylsilyl)amino)ytterbium * 1,2-dimethoxyethane
90669-97-9

bis(bis(trimethylsilyl)amino)ytterbium * 1,2-dimethoxyethane

B

mercury

mercury

Conditions
ConditionsYield
In 1,2-dimethoxyethane addn. of a solution of ((CH3)3Si)2N)2Hg in CH3O(CH2)2OCH3 to Yb metal in an evacuated ampul (20°C, 6 h);; decantation, crystn. (pentane), elem. anal.;A 88%
B 100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

bis(tetrahydrofuran)tris(trimethylsilyl)lutetium(III)
312304-82-8, 827342-25-6

bis(tetrahydrofuran)tris(trimethylsilyl)lutetium(III)

Lu(CH2SiMe3)3(THF)(DME)
884911-37-9

Lu(CH2SiMe3)3(THF)(DME)

Conditions
ConditionsYield
In pentane all manipulations under dry, oxygen-free N2 atm.; mixt. of DME and pentane added to soln. of Lu compd., slowly cooled to 0°C then to -30°C; white solid pptd., vessel cooled to -78°C, mother liquor decanted, residue dried under vac.; elem. anal.;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Pr4O7

Pr4O7

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

[PrBr3(dimethoxyethane)2]
783338-78-3

[PrBr3(dimethoxyethane)2]

Conditions
ConditionsYield
With water In 1,2-dimethoxyethane byproducts: (CH3)3SiOSi(CH3)3; DME, (CH3)3SiBr and water added to Pr4O7; suspn. stirred for 8 days at room temp.; dried in vacuum; elem. anal.;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

(η5-pentamethylcyclopentadienyl)silicon(II) tetrakis(pentafluorophenyl)borate

(η5-pentamethylcyclopentadienyl)silicon(II) tetrakis(pentafluorophenyl)borate

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

[bis(trimethysilyl)amino](pentamethylcyclopentadienyl)[(2-methoxy)ethoxy](methyl)silane
1186017-72-0

[bis(trimethysilyl)amino](pentamethylcyclopentadienyl)[(2-methoxy)ethoxy](methyl)silane

Conditions
ConditionsYield
In hexane at -40℃; for 2h; Inert atmosphere;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

ThCl4(1,4-dioxane)2

ThCl4(1,4-dioxane)2

ThCl4(dimethoxyethane)2

ThCl4(dimethoxyethane)2

Conditions
ConditionsYield
In 1,2-dimethoxyethane room temp., 10 min;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Th(Cl)4(THF)3.5

Th(Cl)4(THF)3.5

ThCl4(dimethoxyethane)2

ThCl4(dimethoxyethane)2

Conditions
ConditionsYield
In 1,2-dimethoxyethane room temp., 10 min;100%
Na13(PH2)(OtBu)12

Na13(PH2)(OtBu)12

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Na13(dme)3(PH2)(OtBu)12

Na13(dme)3(PH2)(OtBu)12

Conditions
ConditionsYield
at 20℃; for 48h;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene
1384933-47-4

4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene

Li2(DME)2[4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene(2-)]

Li2(DME)2[4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene(2-)]

Conditions
ConditionsYield
With n-butyllithium In hexane at -78 - 20℃; for 12h;100%
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

5-nitro-2H-tetrazole
55011-46-6

5-nitro-2H-tetrazole

A

[Na(1,,2-dimethoxyethane)3][bis(5-nitro-2H-tetrazolyl)dihydroborate]

[Na(1,,2-dimethoxyethane)3][bis(5-nitro-2H-tetrazolyl)dihydroborate]

B

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
at 20℃; for 4h; Inert atmosphere;A 100%
B 3.9 mmol
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

5-(trinitromethyl)-2H-tetrazole
75393-84-9

5-(trinitromethyl)-2H-tetrazole

A

[Na(1,,2-dimethoxyethane)3][bis(5-(trinitromethyl)-2H-tetrazolyl)dihydroborate]

[Na(1,,2-dimethoxyethane)3][bis(5-(trinitromethyl)-2H-tetrazolyl)dihydroborate]

B

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
at 20℃; for 4h; Inert atmosphere;A 100%
B 3.8 mmol
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

5-(fluorodinitromethyl)tetrazole
75393-85-0

5-(fluorodinitromethyl)tetrazole

A

[Na(1,,2-dimethoxyethane)3][bis(5-(fluorodinitromethyl)-2H-tetrazolyl)dihydroborate]

[Na(1,,2-dimethoxyethane)3][bis(5-(fluorodinitromethyl)-2H-tetrazolyl)dihydroborate]

B

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
at 20℃; for 4h; Inert atmosphere;A 100%
B 3.7 mmol
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

3,5-dinitro-1H-1,2,4-triazole
26621-32-9

3,5-dinitro-1H-1,2,4-triazole

A

[Na(1,,2-dimethoxyethane)3][bis(3,5-dinitro-1H-1,2,4-triazolyl)dihydroborate]

[Na(1,,2-dimethoxyethane)3][bis(3,5-dinitro-1H-1,2,4-triazolyl)dihydroborate]

B

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
at 20℃; for 4h; Inert atmosphere;A 100%
B 4.1 mmol
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

K{2,6-diisopropylphenylamine(1-)}K{N(SiMe3)2}

K{2,6-diisopropylphenylamine(1-)}K{N(SiMe3)2}

[(DME)K{μ-N(SiMe3)2}{μ-2,6-diisopropylphenylamine(1-)}K]2

[(DME)K{μ-N(SiMe3)2}{μ-2,6-diisopropylphenylamine(1-)}K]2

Conditions
ConditionsYield
at 5℃; for 168h; Inert atmosphere; Schlenk technique;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

hexane
110-54-3

hexane

[C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF)
1541157-10-1

[C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF)

triphenyltin chloride
639-58-7

triphenyltin chloride

0.5C4H8O*0.25C6H14*C36H50ClN4O2Yb

0.5C4H8O*0.25C6H14*C36H50ClN4O2Yb

B

hexaphenylditin
1064-10-4

hexaphenylditin

Conditions
ConditionsYield
Stage #1: [C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF); triphenyltin chloride In tetrahydrofuran for 12h; Schlenk technique;
Stage #2: 1,2-dimethoxyethane; hexane Schlenk technique;
A 75%
B 100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

bis(trifluoromethane)sulfonimide lithium
90076-65-6

bis(trifluoromethane)sulfonimide lithium

C4H10O2*C2F6NO4S2(1-)*Li(1+)

C4H10O2*C2F6NO4S2(1-)*Li(1+)

Conditions
ConditionsYield
at 79.84℃; for 0.5h;100%
With lithium nitrate Concentration; Inert atmosphere; Glovebox;
Glovebox; Sealed tube; Heating;
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

[{2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-tert-butyl-N-(p-tolyl)aniline-(2H)}Na2(tetrahydrofuran)]2

[{2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-tert-butyl-N-(p-tolyl)aniline-(2H)}Na2(tetrahydrofuran)]2

{2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-tert-butyl-N-(p-tolyl)aniline-(2H)}{Na(1,2-dimethoxyethane)}2

{2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-tert-butyl-N-(p-tolyl)aniline-(2H)}{Na(1,2-dimethoxyethane)}2

Conditions
ConditionsYield
In toluene for 0.166667h; Inert atmosphere; Schlenk technique; Glovebox;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

carbon dioxide
124-38-9

carbon dioxide

C98H144K3N2O9Ti2(1-)*C24H48KO6(1+)

C98H144K3N2O9Ti2(1-)*C24H48KO6(1+)

C89H120N2O12Ti2(4-)*4K(1+)*3C4H10O2

C89H120N2O12Ti2(4-)*4K(1+)*3C4H10O2

Conditions
ConditionsYield
Stage #1: carbon dioxide; C98H144K3N2O9Ti2(1-)*C24H48KO6(1+) In tetrahydrofuran under 750.075 Torr; for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: 1,2-dimethoxyethane Inert atmosphere; Glovebox; Schlenk technique;
100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

3,7,10-trioxa-1,5-bis(trimethylsilyl)octamethylbicyclo[3.3.3]undecasilane

3,7,10-trioxa-1,5-bis(trimethylsilyl)octamethylbicyclo[3.3.3]undecasilane

(x)C4H10O2*C12H36O3Si8(2-)*2K(1+)

(x)C4H10O2*C12H36O3Si8(2-)*2K(1+)

Conditions
ConditionsYield
With potassium tert-butylate for 12h;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

C83H131Ge2LiO2Si4

C83H131Ge2LiO2Si4

C75H115Ge2Si4*C12H30LiO6

C75H115Ge2Si4*C12H30LiO6

Conditions
ConditionsYield
for 1h; Inert atmosphere;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

methyllithium
917-54-4

methyllithium

[(tBuN)(Cl)W(μ-NtBu)2Ruη5-C5Me5 ]

[(tBuN)(Cl)W(μ-NtBu)2Ruη5-C5Me5 ]

[Li(DME)][(tBuN)2W(μ-NtBu)(μ-CH2)Ruη5-C5Me5 ]

[Li(DME)][(tBuN)2W(μ-NtBu)(μ-CH2)Ruη5-C5Me5 ]

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78 - 25℃; for 24h; Inert atmosphere; Schlenk technique;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

magnesium bis(trifluoromethane solfonyl)imide
133395-16-1

magnesium bis(trifluoromethane solfonyl)imide

C12H30MgO6(2+)*2C2F6NO4S2(1-)

C12H30MgO6(2+)*2C2F6NO4S2(1-)

Conditions
ConditionsYield
at 100℃; Sealed tube;100%
lanthanum(III) oxide

lanthanum(III) oxide

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

[LaCl3(DME)]

[LaCl3(DME)]

Conditions
ConditionsYield
With H2O In 1,2-dimethoxyethane byproducts: HCl, (CH3)3SiOSi(CH3)3; 4 ds, (Ar); vac. drying, elem. anal.;99.8%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

Ca(C3H(CH3)2N2(C6H3(C3H7)2)2)(C2H5OC2H5)(N(Si(CH3)3)2)

Ca(C3H(CH3)2N2(C6H3(C3H7)2)2)(C2H5OC2H5)(N(Si(CH3)3)2)

C39H69CaN3O2Si2

C39H69CaN3O2Si2

Conditions
ConditionsYield
In hexane at 20℃; for 12h; Inert atmosphere; Schlenk technique;99.7%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

neodymium(III) oxide

neodymium(III) oxide

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

[NdBr3(dimethoxyethane)2]
783338-79-4

[NdBr3(dimethoxyethane)2]

Conditions
ConditionsYield
With water In 1,2-dimethoxyethane byproducts: (CH3)3SiOSi(CH3)3; DME, (CH3)3SiBr and water added to Nd2O3; suspn. stirred for 8 days at room temp.; dried in vacuum; elem. anal.;99.6%
9-borabicyclo[3.3.1]nonane dimer
21205-91-4

9-borabicyclo[3.3.1]nonane dimer

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

trifluoroacetic acid
76-05-1

trifluoroacetic acid

9-trifluoroacetoxy-9-borabicyclo[3.3.1]nonane, adduct with 1,2-dimethoxyethane
169695-38-9

9-trifluoroacetoxy-9-borabicyclo[3.3.1]nonane, adduct with 1,2-dimethoxyethane

Conditions
ConditionsYield
In 1,2-dimethoxyethane byproducts: H2; (inert atmosphere); addn. of CF3COOH to a stirred soln. of the dimer in DME at 0°C, warming to room temp., stirring (14 h); solvent removal (vac.), sublimation;99.5%

110-71-4Related news

Oxidative dehydrogenation of dimethyl ether to 1,2-Dimethoxyethane (cas 110-71-4) over oxide catalysts08/29/2019

Catalysts based on silica-supported Ga2O3, In2O3, La2O3 possess higher activity in oxidative dehydrogenation of dimethyl ether to dimethoxyethane than co-precipitated CaO–SnO2, SrO–SnO2, BaO–SnO2 catalysts.detailed

Short communicationA synthesis of crystalline Li7P3S11 solid electrolyte from 1,2-Dimethoxyethane (cas 110-71-4) solvent08/28/2019

A crystalline solid electrolyte, Li7P3S11, was synthesized by a liquid-phase reaction of Li2S and P2S5 in an organic solvent. A precursor, which was a mixture of solvated Li3PS4 and Li4P2S7, was prepared by mixing Li2S and P2S5 powders in 1,2-dimethoxyethane (DME) solvent. After a vacuum drying ...detailed

Surface tension of diethyl carbonate, 1,2-Dimethoxyethane (cas 110-71-4) and diethyl adipate08/27/2019

The surface tension was investigated with a differential capillary rise method in the temperature range from 273 to 373 K for diethyl carbonate, 278 to 373 K for 1,2-dimethoxyethane, and 293 to 373 K for diethyl adipate, respectively. The uncertainties of the temperature and surface tension were...detailed

Insights into the oxidation kinetics of a cetane improver – 1,2-Dimethoxyethane (cas 110-71-4) (1,2-DME) with experimental and modeling methods08/22/2019

A kinetic investigation was carried out in this work for an oxygenated fuel additive, 1,2-dimethoxyethane (1,2-DME) to reveal the oxidation chemistry responsible for its practical function as a cetane improver. Experiments were conducted for 1,2-DME/O2/N2 mixtures with different equivalence rati...detailed

Phase equilibria of CO2 + 1,2-Dimethoxyethane (cas 110-71-4) at high-pressures08/20/2019

Vapor–liquid (VLE) data for the carbon dioxide + 1,2-dimethoxyethane binary system at 313.15, 323.15, 333.15, and 343.15 K up to 10.69 MPa and the critical curve are reported for the first time. Phase behavior measurements were made in a high-pressure visual cell with variable volume, using a s...detailed

110-71-4Relevant articles and documents

EFFECT OF MODIFIED ADDITIVES ON THE SELECTIVITY OF TRANSFORMATION OF METHANOL INTO AROMATIC HYDROCARBONS OR LOWER OLEFINS IN THE PRESENCE OF PENTASILS

Vasina, T. V.,Isaev, S. A.,Preobrazhenskii, A. V.,Rostanin, N. N.,Konoval'chikov, L. D.,et al.

, (1987)

-

CONVERSION OF METHANOL INTO HYDROCARBONS IN THE PRESENCE OF MODIFIED HIGH-SILICON ZEOLITE CATALYSTS

Vasina, T. D.,Khelkovskaya-Sergeeva, E. G.,Rostanin, N. N.,Konoval'chikov, B. K.,Nefedov, B. K.,Bragin, O. V.

, p. 1347 - 1351 (1986)

-

Niobia-modified aluminas prepared by impregnation with niobium peroxo complexes for dimethyl ether production

Rocha, Angela S.,Da S. Forrester, Aline M.,Lachter, Elizabeth R.,Faro Jr., Arnaldo C.,Sousa-Aguiar, Eduardo F.

, p. 104 - 111,8 (2012)

Use of a water-soluble niobium peroxo complex allowed the preparation of niobium-modified aluminas containing up to 90% of the theoretical niobia monolayer in one impregnation step. There was a maximum in the density of surface Lewis acid sites at 45% of the theoretical monolayer. FTIR of adsorbed pyridine and adsorbed CO2 suggest the vertical growth of the Nb 2O5 layer for the largest niobium contents. The addition of 22.5% of the theoretical monolayer eliminated about 80% of the basic surface hydroxyls, inhibiting the adsorption of gas phase CO2 by the samples. The niobia/alumina catalysts suffered less inhibition by CO2 than the pure alumina in the methanol dehydration reaction, confirming that Nb 2O5 is mainly deposited on sites where the CO2 adsorption is stronger, leaving free sites that are active in catalytic dehydration and less inhibited by CO2, however none of the niobia/aluminas was more active than the pure alumina. Nevertheless, in the direct syngas to DME conversion using a mixed catalyst system comprised of a CuZnAl methanol synthesis catalyst and a methanol dehydration component, the activity was significantly larger with a niobia/alumina as a dehydrating component than with the pure alumina.

Carbonylation of methanol to acetic acid using homogeneous Ru complex catalyst

Kelkar, Ashutosh A.,Kolhe, Devidas S.,Chaudhari, Raghunath V.

, p. 111 - 116 (1992)

Carbonylation of methanol to give acetic acid catalysed by Ru complexes such as trans-Ru(CO)2Cl2(PPh3)2, cis-Ru(CO)2Cl2(PPh3)2 and H2Ru(CO)(PPh3)3 is reported.The highest activity and selectivity were obtained with H2Ru(CO)(PPh3)3 as the catalyst precursor.Hydrogen increases the activity and selectivity of catalysts such as trans-Ru(CO)2Cl2(PPh3)2, cis-Ru(CO)2Cl2(PPh3)2, but has no influence on the activity and selectivity in the case of H2Ru(CO)(PPh3)3.

Marcus,Darwent,Steacie

, p. 993 (1948)

C-C Bond Formation from Dimethil Ether via a Radical Mechanism in the Presence of Strong Acid

Choukroun, Henri,Brunel, Daniel,Germain, Alain

, p. 6 - 7 (1986)

The selective radical dimerization of dimethyl ether by peroxodisulphuryl difluoride in fluorosulphuric acid, suggests that a radical intermediate for initial C-C bond formation in the conversion of methanol into hydrocarbons is a possibility.

Visualizing Element Migration over Bifunctional Metal-Zeolite Catalysts and its Impact on Catalysis

Cheng, Kang,Wang, Genyuan,Wang, Ye,Wang, Yuhao,Zhang, Qinghong,de Jong, Krijn P.,van der Wal, Lars I.

, p. 17735 - 17743 (2021)

The catalytic performance of composite catalysts is not only affected by the physicochemical properties of each component, but also the proximity and interaction between them. Herein, we employ four representative oxides (In2O3, ZnO, Cr2O3, and ZrO2) to combine with H-ZSM-5 for the hydrogenation of CO2 to hydrocarbons directed by methanol intermediate and clarify the correlation between metal migration and the catalytic performance. The migration of metals to zeolite driven by the harsh reaction conditions can be visualized by electron microscopy, meanwhile, the change of zeolite acidity is also carefully characterized. The protonic sites of H-ZSM-5 are neutralized by mobile indium and zinc species via a solid ion-exchange mechanism, resulting in a drastic decrease of C2+ hydrocarbon products over In2O3/H-ZSM-5 and ZnO/H-ZSM-5. While, the thermomigration ability of chromium and zirconium species is not significant, endowing Cr2O3/H-ZSM-5 and ZrO2/H-ZSM-5 catalysts with high selectivity of C2+ hydrocarbons.

Synthesis, characterization and molecular structures of barium(II) trichloroacetate DME/1,4-dioxane compounds

Singh, Sukhjinder,Saini, Deepika,Mehta,Kaur, Ravneet,Ferretti, Valeria

, p. 202 - 209 (2012)

Two new barium(II) trichloroacetate compounds, [Ba(H2O)(DME) (μ-O2CCCl3)2]n (1) and [{Ba(H2O)2(diox)0.5(μ-O2CCCl 3)2}(diox)]n (2) were synthesized and characterized by elemental analyses, physiochemical studies, FT-IR, 1H NMR, thermogravimetric analyses (TG/DTG/DSC) and single crystal X-ray studies. The reaction of hydrated barium(II) trichloroacetate monohydrate with excess DME (1,2-dimethoxyethane) and diox (1,4-dioxane) in methanol at room temperature led to the isolation of the novel compounds 1 and 2, respectively. Bridging trichloroacetate groups are anticipated on the basis of FT-IR studies and this was confirmed by the X-ray studies. Both compounds dissociate to produce ions in water, as shown by molar conductance values. 1H NMR spectroscopy confirms that DME and 1,4-dioxane are coordinated to the metal ion in these compounds. Single crystal X-ray diffraction studies reveal that the barium cation is coordinated to nine O atoms in a deformed coordination polyhedron in both compounds. Structural data of barium(II) trichloroacetates compounds have been obtained for the first time in the present investigation.

The Ionic Hydrogen Bond. 2. Multiple NH+...O and CH?+...O Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers

Meot-Ner (Mautner), Michael

, p. 4912 - 4915 (1983)

Complexes of ammonium ions RNH3+ (R = CH3, c-C6H11), (CH3)3NH+, and pyridineH+ with polyethers and crown ethers are observed in the gas phase in the abscence of the solvent effects.The dissociation energies, ΔH0D, of the RNH3+ polyether complexes range from 29.4 kcal mol-1 (for RNH3+*CH3OCH2CH2OCH3) to 46 kcal mol-1 (RNH3+*18-crown-6).The large ΔH0D values for complexes of polydentate ligands indicate multiple -NH+...O-hydrogen bonding.Such mutiple bonding can contribute up to 18 kcal mol-1 to the bonding in RNH3+*CH3(OCH2CH2)3OCH3 and 21 kcal mol-1 in RNH3+*18-crown-6.Multiple interactions are also evident in the (CH3)3NH+*polyether complexes where -CH?+...O-hydrogen bonding seems to occur; and consecutive -CH?+...O-bonds contribute approximately 6, 4, and 2 kcal/mol-1 respectively for up to three such bonds.Total ΔH0D values in the (CH3)3NH+*polyether complexes thus range from 26.7 kcal mol-1 in (CH3)3NH+*CH3O(CH2)2OCH3 to 41 kcal mol-1 in (CH3)3NH+*18-crown-6.Multiple interaction effects, possibly including van der Waals dispersion forces, are observed also in pyridineH+*polyether complexes.Large negative entropies in RNH3+*acyclic polyether complexes vs.RNH3+*cyclic crown ethers make the acyclic polyethers less efficient ligands.

Alkali Metal Adducts of an Iron(0) Complex and Their Synergistic FLP-Type Activation of Aliphatic C-X Bonds

Tinnermann, Hendrik,Sung, Simon,Csókás, Dániel,Toh, Zhi Hao,Fraser, Craig,Young, Rowan D.

supporting information, p. 10700 - 10708 (2021/07/31)

We report the formation and full characterization of weak adducts between Li+ and Na+ cations and a neutral iron(0) complex, [Fe(CO)3(PMe3)2] (1), supported by weakly coordinating [BArF20] anions, [1·M][BArF20] (M = Li, Na). The adducts are found to synergistically activate aliphatic C-X bonds (X = F, Cl, Br, I, OMs, OTf), leading to the formation of iron(II) organyl compounds of the type [FeR(CO)3(PMe3)2][BArF20], of which several were isolated and fully characterized. Stoichiometric reactions with the resulting iron(II) organyl compounds show that this system can be utilized for homocoupling and cross-coupling reactions and the formation of new C-E bonds (E = C, H, O, N, S). Further, we utilize [1·M][BArF20] as a catalyst in a simple hydrodehalogenation reaction under mild conditions to showcase its potential use in catalytic reactions. Finally, the mechanism of activation is probed using DFT and kinetic experiments that reveal that the alkali metal and iron(0) center cooperate to cleave C-X via a mechanism closely related to intramolecular FLP activation.

PROCESSES FOR FORMING GLYCOLS

-

Paragraph 0096, (2020/05/28)

This disclosure provides processes for forming glycols by upgrading hydrocarbons. In one embodiment, a process for forming a glycol includes introducing a first ether to a dihydrocarbyl peroxide to form a diether and a first alcohol. The process includes introducing the diether to water to form a glycol and a second alcohol. Processes of this disclosure may include one or more of: introducing a hydrocarbyl hydroperoxide to a third alcohol to form the dihydrocarbyl peroxide; oxidizing a first feed stream comprising a branched hydrocarbon to form the hydrocarbyl hydroperoxide and the first alcohol; and/or introducing the second alcohol to a catalyst to form a second ether.

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