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

Overview

Cyclopentyl methyl ether (CPME), also known as methoxycyclopentane, is new environmentally friendly hydrophobic ether solvent with high performance, and could replace tetrahydrofuran, methyl tetrahydrofuran, methyl tert-butyl ether and dioxane and other ether solvents. As a reaction solvent, it can be used for reaction such as Grignard reaction, coupling reaction, coupling amination reaction, metal reduction reaction, Lewis acid reaction and Fried-Clark reaction, etc. It is also used for extraction, crystallization, surface treatment and polymerization processes.

Chemical Properties

Clear liquid

Uses

Different sources of media describe the Uses of 5614-37-9 differently. You can refer to the following data:
1. Cyclopentyl methyl ether (CPME) is an alternative to ether solvents such as THF, diethyl ether, and MTBE with a higher resistance to peroxide formation. The more environmentally conservative CPME solvent replaces hazardous solvents in order to achieve sustainability and reduce environmental and operational costs. CPME offers considerable potential and advantage as a direct replacement for CH2Cl2 in binary eluents using MeOH as the modifier with MeOH-DMC and i-PrOH-EtOAc.
2. Cyclopentyl methyl ether is a hydrophobic ether solvent widely used in Grignard reaction, Friedel-Crafts reaction, Claisen condensation and Beckmann reaction. It plays an important role in extraction and polymerization reactions as well as in surface coatings. It is considered as a replacement for tetrahydrofuran, methyl tert-butyl ether, dioxane and other existing ether solvents due to its excellent properties like high boiling point and relative stability under acidic and basic conditions.
3. Greener alternative solvent in reactions containing the following reagents:Alkali agentsLewis acid-mediated reactionsOrganometallicReduction and OxidationTransition metal catalystsAzeotropic water removalCan also be used in extraction, polymerization, crystallization and surface coatings.The toxicological assessment of cyclopentyl methyl ether (CPME) as a green solvent.

General Description

Cyclopentyl methyl ether (CPME) is a greener alternative to other ethereal solvents such as tetrahydrofuran (THF), 2-methyl tetrahydrofuran (2-MeTHF), dioxane (carcinogenic), tert-Butyl methyl ether (MTBE), and 1,2-dimethoxyethane (DME) and thus has been enhanced for "Safer Solvents and Auxiliaries".

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

• 137-43-9 Cyclopentyl bromide 
• 124-41-4 sodium methylate 
• 930-28-9 cyclopentyl chloride 
• 5736-19-6 sodium cyclopentanolate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 120-92-3 cyclopentanone 
• 96-41-3 Cyclopentanol 
• 77-78-1 dimethyl sulfate 
• 51422-76-5 trans-1-bromo-2-methoxycyclopentane 
• 1193-67-5 1-chloromercurio-2-methoxycyclopentane 
• 107-13-1 acrylonitrile 
• 292638-85-8 acrylic acid methyl ester 
• 142-29-0 cyclopentene 

Downstream Products

• 1316673-54-7 N-benzylidene-2-methoxy-1-(1-methoxycyclopentyl)-2-oxoethanamine N-oxide 
• 1316673-55-8 N-benzylidene-3-(cyclopentyloxy)-1-methoxy-1-oxopropan-2-amine N-oxide 
• 26084-46-8 cyclohexyl thionobenzoate 
• 137-43-9 Cyclopentyl bromide 
• 51440-20-1 (cyclopentyloxy)triethylsilane 
• 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.

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.

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.