5614-37-9

Basic information

• Product Name: Cyclopentyl methyl ether
• Synonyms: Cyclpentyl methyl ether;Cyclopentane,methoxy-;Cyclopentyl methyl ether,99.5%,Extra Dry,stabilized;Cyclopentyl methyl ether, stabilized, 99+%;Cyclopentyl methyl ether, stabilized, AcroSeal, Extra Dry, 99.5%;Cyclopentyl methyl ether, stabilized, extra pure, 99+%;Cyclopentyl Methyl ether, stabilized, extra pure;Cyclopentyl Methyl Ether CPME
• CAS NO: 5614-37-9
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• Product Categories: cyclopentyl-f,whatsapp;8618031153937 ada@tuskwei.com
• Mol File: 5614-37-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: -140°C
• Boiling Point: 106°C
• Flash Point: 106°C
• Appearance: APHA: ≤10/Liquid
• Density: 0.86
• Vapor Pressure: 34.6mmHg at 25°C
• Refractive Index: 1.4210
• Storage Temp.: Flammables area
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility: Miscible with water, alcohols, ketones and hydrocarbons.
• Stability: Volatile
• CAS DataBase Reference: Cyclopentyl methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentyl methyl ether(5614-37-9)
• EPA Substance Registry System: Cyclopentyl methyl ether(5614-37-9)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-22-36/38
• Safety Statements: 26
• RIDADR: UN3271
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 5614-37-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Reactions:
Cyclopentyl methyl ether is used as a greener alternative solvent for various chemical reactions, including Grignard reaction, Friedel-Crafts reaction, Claisen condensation, and Beckmann reaction. It is favored for its high boiling point and relative stability under acidic and basic conditions.
Used in Extraction and Polymerization:
Cyclopentyl methyl ether is used as a solvent in extraction and polymerization reactions, as well as in surface coatings. It is considered a replacement for tetrahydrofuran, methyl tert-butyl ether, dioxane, and other existing ether solvents due to its excellent properties.
Used in Green Chemistry:
Cyclopentyl methyl ether is used as a greener alternative solvent in reactions containing alkali agents, Lewis acid-mediated reactions, organometallic reactions, reduction and oxidation processes, and transition metal catalysts. It also aids in azeotropic water removal and is assessed for its toxicological properties as a green solvent.
Used in Binary Eluents:
Cyclopentyl methyl ether is used as a direct replacement for CH2Cl2 in binary eluents using MeOH as the modifier with MeOH-DMC and i-PrOH-EtOAc, offering considerable potential and advantage in terms of environmental sustainability and operational cost reduction.
Used in the Chemical Industry:
Cyclopentyl methyl ether is used as a reaction solvent in the chemical industry for reactions such as Grignard reaction, coupling reaction, coupling amination reaction, metal reduction reaction, Lewis acid reaction, and Fried-Clark reaction. It is also utilized for extraction, crystallization, surface treatment, and polymerization processes.

Flammability and Explosibility

Highlyflammable

InChI:InChI=1/C6H12O/c1-7-6-4-2-3-5-6/h6H,2-5H2,1H3

Synthetic route

methanol (67-56-1) + Cyclopentanol (96-41-3) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
With large-pore aluminosilicate zeolite ZSM-5 with Si\Al ratio of 40 at 100℃; for 6h; Reagent/catalyst; Temperature;	80.4%

methanol (67-56-1) + cyclopentene (142-29-0) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
With dry acidic ion-exchange resin (SPC108) at 90℃; under 760 Torr; for 7h;	75.5%
With dry acidic ion-exchange resin (SPC118) at 90℃; under 760 Torr; for 7h;	68.9%
With H-ZSM-5-type zeolite at 150℃; under 16501.7 Torr; Temperature; Pressure; Flow reactor;	68.3%

trimethyl phosphite (512-56-1) + Cyclopentanol (96-41-3) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
With PPA at 180 - 190℃; for 2h;	63%

methanol (67-56-1) + cyclopentanone (120-92-3) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
With C6H16Si*AlCl3 In 2-methyltetrahydrofuran at 80℃; for 2h;	56%
With hydrogenchloride; hydrogen; platinum(IV) oxide

Cyclopentyl bromide (137-43-9) + sodium methylate (124-41-4) → cyclopentyl methyl ether (5614-37-9) + cyclopentene (142-29-0)

cyclopentyl chloride (930-28-9) + sodium methylate (124-41-4) → cyclopentyl methyl ether (5614-37-9) + cyclopentene (142-29-0)

Conditions	Yield
at 60℃;
With methanol at 60℃;

cyclopentyl chloride (930-28-9) → cyclopentyl methyl ether (5614-37-9) + cyclopentene (142-29-0)

Conditions	Yield
With sodium methylate at 60℃;

sodium cyclopentanolate (5736-19-6) + methyl iodide (74-88-4) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
With diethyl ether

Cyclopentanol (96-41-3) + dimethyl sulfate (77-78-1) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
(i) NaNH2, (ii) /BRN= 635994/; Multistep reaction;

trans-1-bromo-2-methoxycyclopentane (51422-76-5) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
With sodium In ammonia

1-chloromercurio-2-methoxycyclopentane (1193-67-5) + acrylonitrile (107-13-1) → cyclopentyl methyl ether (5614-37-9) + trans-2-Methoxy-1-cyclopentanpropannitril (88536-55-4, 91222-87-6)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In water; N,N-dimethyl-formamide Yield given;

cyclopentene (142-29-0) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimid 2: Na / liquid ammonia View Scheme

1-(trichloromethyl)-cyclopentanol (10292-51-0) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. KOH 2: ZnSO4 / (heating) View Scheme

cyclopentanone (120-92-3) + cyclopentanone-vapour → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: KOH 2: aq. KOH 3: ZnSO4 / (heating) View Scheme

Cyclopentanol (96-41-3) + methyl iodide (74-88-4) → cyclopentyl methyl ether (5614-37-9)

Conditions	Yield
Stage #1: Cyclopentanol With sodium hydride In DMF (N,N-dimethyl-formamide) at 20 - 120℃; for 2h; Stage #2: methyl iodide In DMF (N,N-dimethyl-formamide) at 50 - 120℃; for 5h;

1-Phenylprop-1-yne (673-32-5) + cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(1-methoxy-1-phenylprop-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	99%

4-methylpent-2-yne (21020-27-9) + cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(2-methoxy-4-methylpent-2-en-3-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	99%

1-phenyl-1-butyne (622-76-4) + cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(1-methoxy-1-phenylbut-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 1-(p-tolyl)-1-hexyne (180071-98-1) → (E)-1-(1-methoxy-1-(p-tolyl)hex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + phenylacetylene (536-74-3) → (E)-1-(2-methoxy-2-phenylvinyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 4-n-methylphenylacetylene (766-97-2) → (E)-1-(2-methoxy-2-(p-tolyl)vinyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

4-Octyne (1942-45-6) + cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(5-methoxyoct-4-en-4-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	97%

cyclopentyl methyl ether (5614-37-9) + C23H45IrNOP2(1+)*C32H12BF24(1-) → C25H45IrNOP2(1+)*C32H12BF24(1-)

Conditions	Yield
With tert-butylethylene at 60℃; for 1.5h; Glovebox; Inert atmosphere; Sealed tube;	97%

cyclopentyl methyl ether (5614-37-9) + 1-ethynyl-3-methyl-benzene (766-82-5) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(2-methoxy-2-(m-tolyl)vinyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	96%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 1-chloro-4-(1-hexynyl)benzene (112545-94-5) → (E)-1-(1-(4-chlorophenyl)-1-methoxyhex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	95%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 1-(hex-1-yn-1-yl)-3-methoxybenzene (112545-96-7) → (E)-1-(1-methoxy-1-(3-methoxyphenyl)hex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	95%

cyclopentyl methyl ether (5614-37-9) + N,N-dimethyl-8-phenyloct-7-ynamide + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-7-(3,3-bis(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl)-8-methoxy-N,N-dimethyl-8-phenyloct-7-enamide

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	94%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 2-methyl-1-buten-3-yne (78-80-8) → (E)-1-(2-methoxy-3-methylbuta-1,3-dien-1-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	94%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 1,1'-biphenyl-1-hexyne → (E)-1-(1-([1,1'-biphenyl]-4-yl)-1-methoxyhex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	93%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 2-(hex-1-ynyl)thiophene (19482-59-8) → (E)-1-(1-methoxy-1-(thiophen-2-yl)hex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	93%

1-ethynyl-4-fluorobenzene (766-98-3) + cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(2-(4-fluorophenyl)-2-methoxyvinyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	92%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 1,4-di(hex-1-yn-1-yl)benzene (168213-37-4) → (E)-1-(1-(4-(hex-1-yn-1-yl)phenyl)-1-methoxyhex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	91%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-2-(1-hexyne-1-yl)benzene + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(1-(2-fluorophenyl)-1-methoxyhex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	91%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + hex-1-yne (693-02-7) → (E)-1-(2-methoxyhex-1-en-1-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	91%

cyclopentyl methyl ether (5614-37-9) + 4-trifluoromethylphenylacetylene (705-31-7) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(2-methoxy-2-(4-(trifluoromethyl)phenyl)vinyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	87%

cyclopentyl methyl ether (5614-37-9) + 1-ethynyl-3-methoxybenzene (768-70-7) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → (E)-1-(2-methoxy-2-(3-methoxyphenyl)vinyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	85%

cyclopentyl methyl ether (5614-37-9) + benzonitrile (100-47-0) → N-cyclopentylbenzamide (53226-42-9)

Conditions	Yield
With iron(III) perchlorate hydrate In neat (no solvent) at 100℃; for 2h; Ritter Amidation;	84%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 4-(hexyn-1-yl)anisole (131558-77-5) → (E)-1-(1-methoxy-1-(4-methoxyphenyl)hex-1-en-2-yl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	84%

1-Azidoadamantane (24886-73-5) + cyclopentyl methyl ether (5614-37-9) → cyclopentyl N-(adamantyl)formimidate

Conditions	Yield
With tert-butylethylene; C27H47IrNP2(1+)*C32H12BF24(1-) at 90℃; for 22h; Reagent/catalyst; Temperature; Glovebox; Inert atmosphere; Irradiation; Sealed tube;	84%

cyclopentyl methyl ether (5614-37-9) + 2,2,2-trichloroethyl 2-(4-bromophenyl)-2-diazoacetate (1641528-26-8) → 2,2,2-trichloroethyl (R)-2-(4-bromophenyl)-3-(cyclopentyloxy)propanoate

Conditions	Yield
With dirhodium tetrakis[(R)-(1-(biphenyl)-2,2-diphenylcyclopropanecarboxylate)] In dichloromethane at 0℃; enantioselective reaction;	83%

cyclopentyl methyl ether (5614-37-9) + 4-methoxybenzoic acid (100-09-4) → cyclopentyloxymethyl 4-methoxybenzoate

Conditions	Yield
With di-tert-butyl peroxide; Fe3O(1,4-benzenedicarboxylate)3 at 120℃; for 3h; High pressure;	83%

cyclopentyl methyl ether (5614-37-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole + 1-(3-ethynylphenyl) ethan-1-one (139697-98-6) → (E)-1-(3-(2-(3,3-bis(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl)-1-methoxyvinyl)phenyl)ethan-1-one

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	83%

cyclopentyl methyl ether (5614-37-9) + methyl 3-ethynylbenzoate (10602-06-9) + 1-fluoro-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → methyl (E)-3-(2-(3,3-bis(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl)-1-methoxyvinyl)benzoate

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	82%

tert-Butyl acrylate (1663-39-4) + cyclopentyl methyl ether (5614-37-9) + 4-bromobenzenecarbonitrile (623-00-7) → tert-butyl 2-(4-cyanophenyl)-3-(1-methoxycyclopentyl)propanoate

Conditions	Yield
With dipotassium hydrogenphosphate; 4-(4-methoxybenzoyl)benzonitrile; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide for 24h; Catalytic behavior; Reagent/catalyst; Wavelength; Irradiation; Inert atmosphere; Sealed tube; regioselective reaction;	81%

Upstream product

• 930-28-9 cyclopentyl chloride 
• 124-41-4 sodium methylate 
• 5736-19-6 sodium cyclopentanolate 
• 74-88-4 methyl iodide 
• 96-41-3 Cyclopentanol 
• 77-78-1 dimethyl sulfate 
• 51422-76-5 trans-1-bromo-2-methoxycyclopentane 
• 120-92-3 cyclopentanone 
• 67-56-1 methanol 
• 142-29-0 cyclopentene 
• 10292-51-0 1-(trichloromethyl)-cyclopentanol 
• 512-56-1 trimethyl phosphite 
• 17860-28-5 1-methoxycyclopentanecarboxylic acid 
• 1193-67-5 1-chloromercurio-2-methoxycyclopentane 

Downstream Products

• 26084-46-8 cyclohexyl thionobenzoate 
• 21823-29-0 Cyclopentyl Nitrate 
• 120-92-3 cyclopentanone 

Relevant articles and documents

Gas-phase etherification of cyclopentanol with methanol to cyclopentyl methyl ether catalyzed by zeolites

Symmetric ethers can be synthesized through the acid-catalyzed self-etherification of biomass-derived alcohols. However, synthesis of asymmetric ethers via catalytic cross-etherification of alcohols is limited by poor selectivity. Herein, we developed an efficient zeolite-catalyzed one-step synthesis of valuable asymmetric cyclopentyl methyl ether (CPME) using gas-phase reaction of bio-based cyclopentanol and methanol. Among different medium- (FER, MCM-22, ZSM-5) and large-pore (BEA, MOR, USY) aluminosilicate zeolites, commercial ZSM-5 catalysts with 2D system of intersecting channels are markedly more selective to CPME. The targeted CPME was produced with a selectivity of 83 % and a yield higher than 80 % over the ZSM-5 catalysts with Si/Al ratios ranging from 15 to 40. Decrease in Si/Al ratio in ZSM-5 enhanced the conversion value, while not affecting the selectivity. FTIR study of the step-by-step adsorption of both reactants in ZSM-5 evidenced the Rideal-Eley mechanism with cyclopentanol adsorbed on acid sites. Therefore, heterogeneously catalyzed gas-phase cross-etherification of renewable cyclopentanol and methanol is a promising process for large-scale applications thanks to its mild operating conditions, high yields and selectivity when using commercial ZSM-5 zeolites as catalysts.

HYDROSILANE/LEWIS ACID ADDUCT, PARTICULARLY ALUMINUM, IRON, AND ZINC, METHOD FOR PREPARING SAME, AND USE OF SAID SAME IN REACTIONS FOR REDUCING CARBONYL DERIVATIVES

Disclosed is an adduct between a Lewis acid, preferably aluminum trichloride, iron trichloride, or zinc dichloride, and a hydrosilane;—a method for preparing same; and a method for for reducing, particularly, an aldehyde, a ketone, an α,β-unsaturated ketone, an imine, or an α,β-unsaturated imine.

METHOD FOR PRODUCING CYCLOPENTYL ALKYL ETHER COMPOUND

The present invention is a method for producing a cyclopentyl alkyl ether compound comprising reacting substituted or unsubstituted cyclopentene with an alcohol compound represented by a formula (2): R1OH in the presence of an acidic zeolite, the cyclopentyl alkyl ether compound being represented by a formula (1): R1—O—R2, wherein R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, and R2 represents a substituted or unsubstituted cyclopentyl group. The present invention provides a method that can produce a cyclopentyl alkyl ether with high reaction efficiency through a liquid-phase reaction even when the raw material feed rate (amount) is increased.

METHOD FOR PRODUCING CYCLOALKYL ALKYL ETHER COMPOUND

The present invention is a method for producing a cycloalkyl alkyl ether compound comprising reacting substituted or unsubstituted cyclopentene or substituted or unsubstituted cyclohexene with an alcohol compound represented by a formula (2): R1OH (wherein R1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms) in a gaseous state in presence of an acidic ion-exchange resin to produce a cycloalkyl alkyl ether compound represented by a formula (1): R1—O—R2 (wherein R1 is the same as defined above, and R2 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group), the acidic ion-exchange resin having a specific surface area of 20 to 50 m2/g, an average pore size of 20 to 70 nm, and a total exchange capacity of 4.8 to 6.0 eq/L-R wet resin.

Cyclopentyl methyl ether production method

The invention discloses a method for producing cyclopentyl methyl ether. According to the method, cyclopentene and methanol used as the raw materials are subjected to etherification reaction to produce cyclopentyl methyl ether, and the method comprises the following steps: (1) etherification, i.e. cyclopentene and methanol are mixed and heated for gasification to perform etherification reaction through a strong acid cation exchange resin fixed bed, the volume liquid hourly space velocity of the materials is controlled at 0.5-4.0 hr-1, the system pressure is controlled at 0.01-0.10 MPa, the feeding temperature is 75-90 DEG C, the mol ratio of cyclopentene to methanol is 1:(0.5-0.8); (2) regeneration, i.e. in the process of etherification, when the conversion rate of cyclopentene is reduced to 10.0 percent below, feeding is stopped and catalyst is regenerated under the conditions that the materials for etherification reaction are used as a regeneration solvent, the volume liquid hourly space velocity of the materials is controlled at 0.1-1.0 hr-1, the system pressure is controlled at 0.3-1.0 MPa, the feeding temperature is 20-90 DEG C, and the regeneration time is 10-30 hours. According to the method for producing cyclopentyl methyl ether, the activity stability of the catalyst is achieved by using the catalytic etherification-regeneration-catalytic etherification circulation process of the resin catalyst, so that the service life and the use period of the catalyst are prolonged, and the regeneration is simple, and the method is easy to achieve industrial operation.

Continuous cyclopentylmethyl ether production process and production system

The present invention discloses a continuous cyclopentylmethyl ether production process and production system, the production process comprises vaporization of cyclopentene, filteration through an adsorption column, mixing with methanol and vaporization in a raw material vaporizer, catalytic addition reaction of the cyclopentene by entering a fixed bed reactor, distillation of the reaction solution by a light component removal tower, recovery and reuse of CPE and the methanol from light components, and rectification of a light component removal tower kettle liquid by a CPME rectification device to obtain cyclopentylmethyl ether, wherein the temperature of the catalytic addition reaction is 100-105 DEG C, the liquid hourly space velocity is 0.35-0.55hr, the gas hourly space velocity is 110-125hr, the pressure is 0.1-0.12Mpa. The conversion rate of the methanol is greater than 95%, the gas chromatography (GC) purity of a product in the reaction solution is greater than 90%, the purity of the cyclopentylmethyl ether prepared by refining is greater than 99.5% (the purity is detected by GC area normalization method), and the total yield of the cyclopentylmethyl ether is more than 80%.

METHOD FOR PRODUCING CYCLOALKYL ALKYL ETHER

PROBLEM TO BE SOLVED: To provide a method for producing a cycloalkyl alkyl ether through efficiently retrieving it in high purity and high yield as the objective product from a reaction mixture resulted from the addition reaction between an alicyclic olefin and an alcohol. SOLUTION: The method for producing the cycloalkyl alkyl ether comprises the following process: The reaction mixture resulted from the addition reaction between the alicyclic olefin and the alcohol is incorporated with another batch of the alicyclic olefin followed by carrying out a distillation, wherein it is especially preferable that the alicyclic olefin has a cyclopentene skeleton or cyclohexene skeleton and the alcohol is methanol.

SOLVENTS CONTAINING CYCLOALKYL ALKYL ETHERS AND PROCESS FOR PRODUCTION OF THE ETHERS

The present inventions are (A) a solvent comprising at least one cycloalkyl alkyl ether (1) represented by the general formula: R1-O-R2 (wherein R1 is cyclopentyl or the like; and R2 is C1-10 alkyl or the like); (B) a method of preparations the ethers (1) characterized by reacting an alicyclic olefin with an alcohol in the presence of an acid ion-exchange resin having a water content of 5 wt% or less. The solvent is useful as cleaning solvent for electronic components, precision machinery components or the like, reaction solvent using various chemical reactions, extraction solvent for extracting objective organic substances, solvent or remover for electronic and electrical materials, and so on. The process enables industrially advantageous production of the objective cycloalkyl alkyl ethers (1).

Direct methylation of primary and secondary alcohols by trimethyl phosphate to prepare pure alkyl methyl ethers

Primary and secondary alcohols and diols react autocatalytically with trimelhyl phosphate plus small amounts of polyphosphoric acid at 185°C to give the corresponding methyl ethers. High purity and good yields are achieved when the ether is distilled from the reaction mixture as it is formed. By controlled addition even low-boiling alcohols can be methylated successfully. The reaction mechanism is undetermined. Peroxide formation in ethers is inhibited by storage over 10 molal KOH. Pure isotropic optical crystals are used for refractometer calibration. Improved physical property and NMR data (1H and 13C) are reported for thirteen methyl ethers. Simple two-point linear extrapolation of NMR shifts (especially 13C) to infinite dilution produces highly reproducible δ°-values (to 0.01 ppm or better) which uniquely characterize a molecule even when unidentified and/or not isolated from a mixture. This capability appears not to have been recognized in the literature. Acta Chemica Scandinavica 1998.

Reactions of alkali metal anions. XV. Reaction of ketones with alkali metal anions

The potassium anions were found to react with ketones to39 yield both alcoholates and enolates. On the basis of the ESR and K NMR measurements the mechanism of this reaction is proposed. According to the proposed mechanism in the first step a ketyl radical is formed which after disproportionation yields an enolate and an alcoholate but only in the case of ketones having hydrogen atom in α-position in respect to carbonyl group.