IP Library Granted Patent US 8,536,385
Granted Patent B2
US 8,536,385 · App. 13/370,007 · Granted Sep 17, 2013

Process for preparing dimethyl ether and process for preparing a mixture of dimethyl ether and methanol

Inventors: Keiichi Okuyama (Kawasaki, JP); Yotaro Ohno (Tokyo, JP); Takashi Ogawa (Tokyo, JP); Seiji Aoki (Tokyo, JP); Tsutomu Shikada (Kawasaki, JP); Yasuhiro Mogi (Kawasaki, JP); Toshifumi Suzuki (Kawasaki, JP); Yasuo Miyoshi (Kawasaki, JP); Nobuaki Kobayashi (Tokyo, JP); Kazuro Suzuki (Tokyo, JP)
Assignees: Inpex Corporation; Japan Petroleum Exploration Co., Ltd.; Total Gas & Power Ventures; Toyota Tsusho Corporation
C07C29/16
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Quick Facts
Patent No.
US 8,536,385
App. No.
13/370,007
Granted
Sep 17, 2013
Kind
B2
Abstract

A process for preparing dimethyl ether or a mixture of dimethyl ether and methanol including passing a raw gas containing carbon monoxide and hydrogen through a catalyst slurry containing a mixture including (a) a medium oil having as a main component, a branched, saturated aliphatic hydrocarbon having 16 to 50 carbon atoms, 1 to 7 tertiary carbon atoms, 0 quaternary carbon atoms, and 1 to 16 carbon atoms in the branched chains bonded to the tertiary carbon atom; and at least one of the tertiary carbon atoms is bonded to hydrocarbon chains with a chain length having 4 or more of carbon atoms in three directions, (b) a methanol synthesis catalyst; (c) a methanol dehydration catalyst; and (d) a methanol shift catalyst or a methanol dehydration/shift catalyst.

Claims (12)

1. A process for preparing dimethyl ether comprising passing a raw gas containing carbon monoxide and hydrogen through a catalyst slurry containing a mixture comprising (a) a medium oil comprising, as a main component, a branched, saturated aliphatic hydrocarbon having 16 to 50 carbon atoms, 1 to 7 tertiary carbon atoms, 0 quaternary carbon atom, and 1 to 16 carbon atoms in the branched chains bonded to the tertiary carbon atoms; and at least one of the tertiary carbon atoms being bonded to hydrocarbon chains with a chain length having 4 or more of carbon atoms in three directions; (b) a methanol synthesis catalyst; (c) a methanol dehydration catalyst; and (d) a methanol shift catalyst or a methanol dehydration/shift catalyst.

2. A process for preparing a mixture of dimethyl ether and methanol comprising passing a raw gas containing carbon monoxide and hydrogen through a catalyst slurry containing a mixture comprising (a) a medium oil comprising as a main component, a branched, saturated aliphatic hydrocarbon having 16 to 50 carbon atoms, 1 to 7 tertiary carbon atoms, 0 quaternary carbon atom, and 1 to 16 carbon atoms in the branched chains bonded to the tertiary carbon atoms; and at least one of the tertiary carbon atoms being bonded to hydrocarbon chains with a chain length having 4 or more of carbon atoms in three directions; (b) a methanol synthesis catalyst; (c) a methanol dehydration catalyst; and (d) a methanol shift catalyst or a methanol dehydration/shift catalyst.

3. The process according to claim 1 , wherein the branched, saturated aliphatic hydrocarbon has 20 to 40 carbon atoms and 1 to 4 tertiary carbon atoms.

4. The process according to claim 1 , wherein the branched, saturated aliphatic hydrocarbon is represented by formula (I):

wherein R 1 , R 2 and R 4 are independently an n- or iso-alkyl group having 4 to 16 carbon atoms, R 3 is an n- or iso-alkyl group having 1 to 3 carbon atoms, m is an integer of 1 to 7, n is an integer of 0 to 37, and p is an integer of 0 to 12, provided that —(CR 2 H)—, —(CH 2 )— and —(CR 3 H)— are bonded in any order and the total numbers of each unit are m, n and p, respectively.

5. The process according to claim 1 , wherein the branched, saturated aliphatic hydrocarbon is an α-olefin polymer.

6. The process according to claim 1 , wherein the medium oil has a pour point of −10° C. or lower.

7. The process according to claim 2 , wherein the branched, saturated aliphatic hydrocarbon has 20 to 40 carbon atoms and 1 to 4 tertiary carbon atoms.

8. The process according to claim 2 , wherein the branched, saturated aliphatic hydrocarbon is represented by formula (I):

wherein R 1 , R 2 and R 4 are independently an n- or iso-alkyl group having 4 to 16 carbon atoms, R 3 is an n- or iso-alkyl group having 1 to 3 carbon atoms, m is an integer of 1 to 7, n is an integer of 0 to 37, and p is an integer of 0 to 12, provided that —(CR 2 H)—, —(CH 2 )— and —(CR 3 H)— are bonded in any order and the total numbers of each unit are m, n and p, respectively.

9. The process according to claim 2 , wherein the branched, saturated aliphatic hydrocarbon is an α-olefin polymer.

10. The process according to claim 2 , wherein the medium oil has a pour point of −10° C. or lower.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2016
From: INPEX CORPORATION; JAPAN PETROLEUM EXPLORATION CO., LTD.; TOTAL GAS & POWER VENTURES; TOYOTA TSUSHO CORPORATION
To: RENFUD CORPORATION
Reel/Frame 039330/0304 →
MERGER Recorded Apr 12, 2016
From: INPEX CORPORATION; TEIKOKU OIL CO., LTD.
To: INPEX CORPORATION
Reel/Frame 038257/0776 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2012
From: OKUYAMA, KEIICHI; OHNO, YOTARO; OGAWA, TAKASHI; AOKI, SEIJI; SHIKADA, TSUTOMU; MOGI, YASUHIRO; SUZUKI, TOSHIFUMI; MIYOSHI, YASUO; KOBAYASHI, NOBUAKI; SUZUKI, KAZURO
To: LNG JAPAN CORPORATION; INPEX CORPORATION; JFE HOLDINGS, INC.; JFE STEEL CORPORATION; JFE ENGINEERING CORPORATION; JAPAN PETROLEUM EXPLORATION CO., LTD.; TOTAL GAS & POWER VENTURES; TOYOTA TSUSHO CORPORATION; TAIYO NIPPON SANSO CORPORATION; HITACHI, LTD.; MARUBENI CORPORATION
Reel/Frame 027681/0107 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2012
From: LNG JAPAN CORPORATION; JFE HOLDINGS, INC.; JFE STEEL CORPORATION; JFE ENGINEERING CORPORATION; TAIYO NIPPON SANSO CORPORATION; HITACHI, LTD; MARUBENI CORPORATION
To: INPEX CORPORATION; JAPAN PETROLEUM EXPLORATION CO., LTD.; TOTAL GAS & POWER VENTURES; TOYOTA TSUSHO CORPORATION
Reel/Frame 027681/0242 →
Priority Claims (8)
JP 2003-059840 · Mar 6, 2003 · national
JP 2003-059897 · Mar 6, 2003 · national
JP 2003-059898 · Mar 6, 2003 · national
JP 2003-060560 · Mar 6, 2003 · national
JP 2004-060291 · Mar 4, 2004 · national
JP 2004-061170 · Mar 4, 2004 · national
JP 2004-061445 · Mar 4, 2004 · national
JP 2004-061446 · Mar 4, 2004 · national
Continuity (3)
Division 12800051 · May 7, 2010
Division 10546221
Related Publication 20120157554A1 · Jun 21, 2012