US009 l20734B2

United States Patent (io Patent No.: US 9,120,734 B2

Kelkar et al. (4s Date of Patent: Sep. 1, 2015

(54) TWO-STEP SYSTEM AND METBOD FOR (56) References Cited

TBE PRODUCTION OF METHYL ISOBUTYL
KETONE U.S. PATENT DOCUMENTS
2,827,490 A 3'1958 Martin
(71) Applicant: ClearWaterBay Technology, Inc., 3,953,517 A 4'1976 Schmitt et al.
Pomona, CA (US) 5,149,881 A 9'1992 Ushikubo et al.
5,684,207 A 11'1997 Chen et al.
(72) Inventors: Vaibhav V. Kelkar, Chino Hills, CA 6,762,328 B2 7'2004 Saayman et al.
(US); Drow Lionel OYoung, Walnut, 7,671,239 B2 3'2010 Hahn et al.
CA ITIS); Christianto Wibowo, Chino 8,242,314 B2 8'2012 Hahn et al.
2010'0317897 Al 12'2010 Sawrey
Hills, CA (US); Madhura Kelkar,
Chino Hills, CA (US); Bok Chung OTHER PUBLICATIONS
Chan, Hong Kong (CN)
S. Kudo, Formation of Higher Molecular Weight Ketones from
(73) Assignee: ClearWaterBay Technology, Inc., Acetone or Isopropanol, J. Chem. Soc. Japan Ind. Chem. Sec., 58
Pomona, CA (US) (1955), 785-787.
Uhde GmbH, Uhde Technology Profile, Methyl isobutyl ketone
Notice: Subject to any disclaimer, the term of this (MIBK), 2 pages, 2005.
patent is extended or adjusted under 35 International Search Report and Written Opinion in International
U.S.C. 154(b) by 0 days. Application No. PCT/US2014'047086, mailed Oct. 8, 2014.

Appl. No.: 14/289,592 Primary Examine r Sikarl Witherspoon

(74) Attorney, Agent, or Firm Nixon Peabody LLP
Filed: May 28, 2014
(57) ABSTRACT
(65) Prior Publication Data
Embodiments of the present invention describe systems and
US 2015/0025277 Al Jan. 22, 2015 methods for production of methyl isobutyl ketone (MIBK)
from acetone and hydrogen in a two-step process. In a first
Related U.S. Application Data step, acetone is converted to a product stream containing
(60) Provisional application No. 61/847,507, filed on Jul. mesityl oxide (MO) at a temperature in the range of about
17, 2013. 0-120 C. and a pressure in the range of about 1-3 atm. The
composition of the product stream from the first reaction step
Int. Cl. is adjusted so that the resulting stream can undergo a favor-
CO7C 45773 (2006.01) able liquid-liquid separation in a decanter, and an MO rich
B01J 8700 (2006.01) product stream can be recovered. The composition of the feed
B01J 19700 (2006.01) to the decanter is controlled by choosing the number ofreac-
U.S. CI. tor stages for the first reaction step and their operating tem-
CPC CO7C 45773 (2013.01); B01J 1970046 peratures, and/or by recycling some MIBK to the decanter
(2013.01); B01J 2219/00006 (2013.01); B01J feed. The method does not require a substantially complete
2219/00306 (2013.01) conversion of acetone in the first reaction step, nor does it
Field of Classification Search require a removal of DAA from the product of the first reac-
CPC C07C 45/73; B01J 2219/00006 tion step by separation.
USPC 568/388, 392, 396
See application file for complete search history. 15 Claims, 2 Drawing Sheets
U.S. Patent Sep. 1, 2015 Sheet 1 of 2 US 9,120,734 B2

Solvent Solvent

M3

MI M4
04
02 A2 A4

MO Water MIBK Water

(a) (b)

Solvent

M5 O6
M6

MO

A6
Water

FIG. 1(a) - FIG. 1(c)

(not to scale)
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