Process for production of cycloalkyl alkyl ethers

• US 8,017,813 B2
• Filed: 08/12/2008
• Issued: 09/13/2011
• Est. Priority Date: 06/28/2001
• Status: Expired due to Term

• Current Assignee: ZEON Corporation
• Original Assignee: ZEON Corporation
• Inventors: Watanabe, Kiyoshi, Teraishi, Kazuo, Ohta, Genichi, Kin, Idan
• Primary Examiner(s): Webb; Gregory E
• Application Number:
  US12/222,572
• Publication Number:
  US 20080312125A1
• Time in Patent Office: 1,127 Days
• Field of Search: 568/579, 568/697, 568/698, 510/175, 510/506
• US Class Current: 568/579
• CPC Class Codes: C07B 49/00 Grignard reactions
• CPC Class Codes: C07B 63/00 Purification; Separation separation of optically-active compounds C07B57/00; Stabilisation; Use of additives
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 29/40 with compounds containing carbon-to-metal bonds
• CPC Class Codes: C07C 33/20 monocyclic
• CPC Class Codes: C07C 35/21 polycyclic, at least one hydroxy group bound to a non-condensed ring
• CPC Class Codes: C07C 41/06 by addition of organic compounds only
• CPC Class Codes: C07C 43/184 to a carbon atom of a non-condensed ring
• CPC Class Codes: C11D 2111/22 Electronic devices, e.g. PCBs or semiconductors
• CPC Class Codes: C11D 7/263 Ethers
• CPC Class Codes: C11D 7/5022 containing oxygen
• CPC Class Codes: G11B 20/00086 Circuits for prevention of unauthorised reproduction or copying, e.g. piracy indicating unauthorised use of record carriers in general G11B23/28; scrambling for television signal recording H04N5/913; network architectures or network protocols for network security H04L63/00; cryptographic mechanisms or cryptographic arrangements for secret or secure communication H04L9/00
• CPC Class Codes: G11B 20/0021 involving encryption or decryption of contents recorded on or reproduced from a record carrier
• CPC Class Codes: G11B 20/00507 wherein consecutive physical data units of the record carrier are encrypted with separate encryption keys, e.g. the key changes on a cluster or sector basis

Abstract

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).

Claims

1. A process for producing a cycloalkyl alkyl ether compound of formula (1), (2), or (3):

R¹—

O—

R², 

 

formula (1)

wherein R¹ represents a cyclopentyl group or cyclohexyl group which may have a substituent and R² represents an alkyl group having 1-10 carbon atoms or a cycloalkyl group having 3-8 carbon atoms which may have a substituent;

R¹—

O—

R³, 

 

formula (2)

wherein R¹ represents a cyclopentyl group or cyclohexyl group which may have a substituent and R³ represents an alkyl group having 1-10 carbon atoms or a cycloalkyl group having 3-8 carbon atoms;

R⁴—

O—

R³, 

 

formula (3)

wherein R⁴ is a cyclopentyl group and R³ represents an alkyl group having 1-10 carbon atoms or a cycloalkyl group having 3-8 carbon atoms,

said process comprising reacting an alicyclic olefin with an alcohol in the presence of an acidic ion-exchange resin having a water content of 5 wt % or less.

2. The process of claim 1, wherein the substituent is selected from the group consisting of an alkyl group having 1-4 carbon atoms, an alkoxy group having 1-4 carbon atoms, an alkylthio group having 1-4 carbon atoms, and a halogen atom.

3. The process of claim 1, wherein said process comprises reacting a gaseous alicylic olefin with a gaseous alcohol in the presence of an acidic ion-exchange resin having a water content of 5 wt % or less.

4. The process of claim 1, wherein said process comprises flowing a mixture comprising an alicyclic olefin and an alcohol in a gaseous state through a column filled with an acidic ion-exchange resin having a water content of 5 wt % or less.

5. The process of claim 4, wherein said mixture is flowed in a down flow-type method.

6. The process of claim 4, wherein the mol ratio of the alicyclic olefin to the alcohol ranges from 1:

3 to 20;

1.