Method for producing aldehyde

Patent metadata

Field	Value
Publication number	US-2016289151-A1
Application number	US-201415035586-A
Country	US
Kind code	A1
Filing date	Dec 26, 2014
Priority date	Dec 26, 2013
Publication date	Oct 6, 2016
Grant date	—

Abstract

Provided is a method for producing aldehydes that brings an excellent alcohol conversion and aldehyde selectivity while suppressing generation of aldol condensates, etc. The method for producing aldehydes includes a step of dehydrogenating primary alcohol in the presence of a catalyst composition. The catalyst composition is a first catalyst composition obtained by adding a potassium salt of a weak acid to a dehydrogenation catalyst containing copper as an active species.

First claim

1 - 11 . (canceled)

12 . A method for producing an aldehyde, comprising
dehydrogenating a primary alcohol in the presence of a catalyst composition, wherein the catalyst composition is a first catalyst composition obtained by adding a potassium salt of a weak acid to a dehydrogenation catalyst comprising copper as an active species, and a quantity of surface acid sites of the dehydrogenation catalyst measured by a temperature-programmed desorption analysis of ammonia is in a range of 0.10 mmol/g or more and 0.20 mmol/g or less.

13 . The method for producing an aldehyde according to claim 12 , wherein the quantity of surface acid sites of the dehydrogenation catalyst in the first catalyst composition measured by the temperature-programmed desorption analysis of ammonia is in a range of 0.11 mmol/g or more and 0.16 mmol/g or less.

14 . The method for producing an aldehyde according to claim 12 , wherein a quantity of surface base sites of the dehydrogenation catalyst in the first catalyst composition measured by a temperature-programmed desorption analysis of carbon dioxide is in a range of 0.65 mmol/g or more and 1.50 mmol/g or less.

15 . The method for producing an aldehyde according to claim 14 , wherein a difference between the quantity of surface base sites and surface acid sites of the dehydrogenation catalyst in the first catalyst composition is in a range of 0.40 to 1.30 mmol/g.

16 . The method for producing an aldehyde according to claim 12 , wherein the dehydrogenation catalyst is supported on a carrier.

17 . The method for producing an aldehyde according to claim 16 , wherein the carrier is an oxide or a hydroxide of zinc or aluminum.

18 . The method for producing an aldehyde according to claim 12 , wherein the dehydrogenation catalyst comprises at least two components that comprise a metallic element other than copper.

19 . The method for producing an aldehyde according to claim 12 , wherein the dehydrogenation catalyst is CuFeAl, CuCrMn or CuZnAl.

20 . The method for producing an aldehyde according to claim 12 , wherein the dehydrogenation catalyst comprises copper-iron-aluminum (CuFeAl), and the atomic ratio of the elements constituting the catalyst (copper/iron/aluminum) is 1/0.4-2.5/0.5-5.0.

21 . The method for producing an aldehyde according to claim 12 , wherein an addition amount of the potassium salt of the weak acid is in a range of 0.1 mmol or more and 1.0 mmol or less based on a total amount of 1 g of metallic elements in the dehydrogenation catalyst.

22 . The method for producing an aldehyde according to claim 12 , wherein the catalyst composition is a second catalyst composition obtained by calcinating the first catalyst composition.

23 . The method for producing an aldehyde according to claim 12 , wherein the primary alcohol is an aliphatic alcohol with a carbon number of 4 to 15.

24 . The method for producing an aldehyde according to claim 12 , wherein the primary alcohol is a saturated aliphatic alcohol with a carbon number of 4 to 15.

25 . The method for producing an aldehyde according to claim 12 , wherein said dehydrogenating of the primary alcohol is performed at a temperature of from 180 degree C. to 300 degree C.

26 . The method for producing an aldehyde according to claim 12 , wherein the potassium salt of the weak acid is at least one salt selected from the group consisting of potassium carbonate, potassium acetate, and potassium hydrogencarbonate.

27 . A catalyst composition,
wherein the catalyst composition is obtained by adding a potassium salt of a weak acid to a dehydrogenation catalyst comprising copper as an active species, and wherein a quantity of surface acid sites of the dehydrogenation catalyst measured by a temperature-programmed desorption analysis of ammonia is in a range of 0.10 mmol/g or more and 0.20 mmol/g or less.

28 . The catalyst composition according to claim 27 wherein the quantity of surface acid sites of the dehydrogenation catalyst measured by the temperature-programmed desorption analysis of ammonia is in a range of 0.11 mmol/g or more and 0.16 mmol/g or less.

29 . The catalyst composition according to claim 27 , wherein the dehydrogenation catalyst comprises copper-iron-aluminum (CuFeAl), and the atomic ratio of the elements constituting the catalyst (copper/iron/aluminum) is 1/0.4-2.5/0.5-5.0.

30 . A method for producing a catalyst composition, comprising mixing a potassium salt of a weak acid into a dehydrogenation catalyst comprising copper as an active species,
wherein a quantity of surface acid sites of the dehydrogenation catalyst measured by a temperature-programmed desorption analysis of ammonia is in a range of 0.10 mmol/g or more and 0.20 mmol/g or less.

31 . The method for producing a catalyst composition according to claim 30 , further comprising calcinating a mixture of the dehydrogenation catalyst and the potassium salt of the weak acid.

Assignees

• Kao Corp

Inventors

• Arai Tsubasa
• Kono Jun
• Ataka Yoshiharu

Classifications

• B01J37/035

  Precipitation on carriers · CPC title

• C07C45/002 Primary

  by dehydrogenation · CPC title

• B01J31/0275

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0269 · CPC title

• B01J23/745

  Iron · CPC title

• B01J2231/763

  of -CH-XH (X= O, NH/N, S) to -C=X or -CX triple bond species · CPC title