Solvents containing cycloakyl alkyl ethers and process for production of the ethers

• US 20050065060A1
• Filed: 06/27/2002
• Published: 03/24/2005
• Est. Priority Date: 06/28/2001
• Status: Active Grant

• Current Assignee: ZEON Corporation
• Original Assignee: ZEON Corporation
• Inventors: Kin, Idan, Watanabe, Kiyoshi, Teraishi, Kazuo, Ohta, Genichi
• Granted Patent: US 7,494,962 B2
• Time in Patent Office: Days
• US Class Current: 510/506
• 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 solvent comprising at least one cycloalkyl alkyl ether compound represented by the formula (1):

R¹—

O—

R², 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.

11. The solvent according to claim 1, having a water content of 100 ppm or less.

12. The solvent according to claim 1, further comprising an antioxidant.

13. A method of reacting an organic metal characterized by using the solvent according to any one of claims 1-3, 5 or 6.

14. A Grignard reaction method characterized by using the solvent according to any one of claims 1-3, 5 or 7.

15. A method of extracting an organic compound characterized by using the solvent according to any one of claims 1-3 or 8.

16. A method of cleaning an article characterized by using the solvent according to any one of claims 1-4.

17. A method for manufacturing electronic or electrical parts characterized by using the solvent according to any one of claims 1-3, 9, or 10.

2. A solvent comprising at least one cycloalkyl alkyl ether compound represented by the formula (2):

R¹—

O—

R³, wherein R¹ is the same as defined above and R³ represents an alkyl group having 1-10 carbon atoms or a cycloalkyl group having 3-8 carbon atoms.

3. A solvent comprising at least one cycloalkyl alkyl ether compound represented by the formula (3):

R⁴—

O—

R³, wherein R⁴ is a cyclopentyl group and R³ is the same as defined above.

4. A cleaning solvent comprising at least one cycloalkyl alkyl ether compound represented by the above formulas (1), (2), or (3).

5. A reaction solvent comprising at least one cycloalkyl alkyl ether compound represented by the above formulas (1), (2), or (3).

6. An organic metal reaction solvent comprising at least one cycloalkyl alkyl ether compound represented by the above formulas (1), (2), or (3).

7. A Grignard reaction solvent comprising at least one cycloalkyl alkyl ether compound represented by the above formulas (1), (2), or (3).

8. An extraction solvent comprising at least one cycloalkyl alkyl ether compound represented by the above formulas (1), (2), or (3).

9. A solvent for electronic or electrical materials comprising at least one cycloalkyl alkyl ether compound represented by the above formulas (1), (2), or (3).

10. A parting solvent comprising at least one cycloalkyl alkyl ether compound represented by the above formulas (1), (2), or (3).

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

19. A process for recovering a cycloalkyl alkyl ether compound comprising:

(1) a step of carrying out a reaction using the cycloalkyl alkyl ether compound as a solvent,

(2) a step of adding water to the reaction mixture to form an organic layer and a water layer,

(3) a step of separating the organic layer from the water layer, and

(4) a step of recovering the cycloalkyl alkyl ether compound from the organic layer.

20. A process for carrying out an organic synthesis reaction using a recovered cycloalkyl alkyl ether compound comprising:

(1) a step of carrying out a reaction using a cycloalkyl alkyl ether compound as a solvent,

(2) a step of adding water to the reaction mixture to form an organic layer and a water layer,

(3) a step of separating the organic layer from the water layer,

(4) a step of recovering the cycloalkyl alkyl ether compound from the organic layer, and

(5) a step of supplying the recovered cycloalkyl alkyl ether compound to the step (1).