Process for producing 1-(4-isobutylphenyl)ethanol by hydrogenation of 1-(4-isobutyl-phenyl)ethanone in the presence of a catalyst composition comprising copper

Patent metadata

Field	Value
Publication number	US-12378174-B2
Application number	US-201917298692-A
Country	US
Kind code	B2
Filing date	Dec 2, 2019
Priority date	Dec 3, 2018
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

Described is a process for producing 1-(4-isobutylphenyl)ethanol by reacting 1-(4-isobutyl-phenyl)ethanone with hydrogen in the presence of a catalyst composition comprising cop-per and one or more metals other than copper, and a use of a respective composition and/or of a pre-composition, the pre-composition comprising a mixture of oxides of copper and oxides of one or more metals other than copper, in a catalytic hydrogenation process for producing 1-(4-isobutylphenyl)ethanol from 1-(4-isobutylphenyl)ethanone.

First claim

The invention claimed is:

1. A process for producing 1-(4-isobutylphenyl) ethanol comprising:
S3) reacting 1-(4-isobutylphenyl)ethenone with hydrogen in the presence of a catalyst composition comprising copper and one or more metal other than copper,
wherein the catalyst composition comprises
c1) the copper in a total amount in a range of from 65 mass-% to 92.5 mass-%, relative to the total mass of metals present in the catalyst composition;
c2) a carrier component comprising one or more substance selected from the group consisting of silicon and silicon compounds, wherein a total amount of silicon in the catalyst composition, relative to the total mass of copper present in the catalyst composition, is in a range of from 3.5 mass-% to 15.0 mass-%;
and
c3) manganese in a total amount in a range of from 0.75 mass-% to 3.15 mass-%, relative to the total mass of metals present in the catalyst composition;
and
one or more metal selected from the group consisting of sodium and calcium, wherein a total amount of the one or more metal selected from the group consisting of sodium and calcium in the catalyst composition, relative to the total mass of metals present in the catalyst composition, is in a range of from 4.5 mass-% to 15.0 mass-%; and
wherein the catalyst composition has a molar ratio of copper:aluminum of ≥10.

2. The process according to claim 1 , wherein the catalyst composition comprises:
c1) copper in the total amount in a range of from 65 mass-% to 92.5 mass-%, relative to the total mass of metals present in the catalyst composition;
c2) a carrier component comprising one or more substance selected from the group consisting of silicon and silicon compounds, wherein a total amount of silicon in the catalyst composition, relative to the total mass of copper present in the catalyst composition, is in a range of from 5.0 mass-% to 15.0 mass-%;
and
c3) manganese in the total amount in a range of from 0.75 mass-% to 3.15 mass-%, relative to the total mass of metals present in the catalyst composition; and
one or more metal selected from the group consisting of sodium and calcium, wherein a total amount of the one or more metals selected from the group consisting of sodium and calcium in the catalyst composition, relative to the total mass of metals present in the catalyst composition, is in a range of from 7.5 mass-% to 12.5 mass-%.

3. The process according to claim 1 , wherein added masses of components c1) and c3) present in the catalyst composition make up a total mass of metals present in the catalyst composition.

4. The process according to claim 1 , wherein in the catalyst composition a molar ratio of:
copper:nickel is >10;
and/or
copper:chromium is >10;
and/or
copper: ruthenium is >10;
and/or
copper: palladium is >10
and/or
copper: graphite carbon is >50.

5. The process according to claim 1 ,
wherein
in the catalyst composition, a molar ratio of
copper:zinc is >10,

and/or
the 1-(4-isobutylphenyl) ethanone present in S3) comprises other organic and/or inorganic chemical compounds selected from the group consisting of acetic acid, acetates, fluorides, chlorides; oxygen-containing compounds selected from ketones, aldehydes, esters, ethers and water; nitrogen-containing compounds selected from amines, amides, urea compounds, nitrates, nitrites, and nitrosyl compounds; and sulfur-containing compounds selected from thiols, thio ethers, sulfides, sulfates, and sulfones,
in an amount of ≤10 mass-%, relative to the total mass of the 1-(4-isobutylphenyl) ethanone and the other organic and/or inorganic chemical compounds.

6. The process according to claim 1 wherein
the 1-(4-isobutylphenyl) ethanone is present in a liquid phase for at least a part of the process or process time of S3),
and/or
1-(4-isobutylphenyl) ethanone and/or 1-(4-isobutylphenyl) ethanol make up ≥90.0 vol.-% of a liquid phase in S3).

7. The process according to claim 1 , wherein the reacting in S3) is carried out at least for a part of the process or process time:
at a hydrogen pressure in a range of from 0.5 to 8.0 MPa;
and/or
at a molar ratio of hydrogen to the 1-(4-isobutylphenyl) ethanone which is present at the start of S3) in a range of from 1 to 20;
and/or
at a temperature in the range of from 30° C. to 200° C.

8. The process according to claim 1 , wherein
the reacting in S3) is carried out continuously for at least a part of the process or process time.

9. The process according to claim 8 , wherein the reacting in S3) is carried out continuously for at least a part of the process or process time
in one or more fixed-bed reactors
and/or
in two or more serially connected reactors comprising one or more main reactors, each comprising one or more recycle loops or one combined recycle loop, and one or more post-reactors, not comprising recycle loops,
and/or
the catalyst composition is or comprises a fixed-bed catalyst or fixed-bed catalyst composition,
and/or
the catalyst load is in the range of from 0.1 kg [1-(4-isobutylphenyl) ethanone]/(kg catalyst composition*h) to 5.0 kg [1-(4-isobutylphenyl) ethanone]/(kg catalyst composition*h),
where the kg [1-(4-isobutylphenyl) ethanone] is the total amount of 1-(4-isobutylphenyl) ethanone present at the start of the reaction;
and/or
1-(4-isobutylphenyl) ethanone is continuously fed into or provided to reaction step S3) in an amount of ≤500 t/h.

10. The process according to claim 9 , wherein the reacting in step S3) is carried out continuously for at least a part of the process or process time in two or more serially connected reactors comprising one or more main reactors, each comprising one or more recycle loops or one combined recycle loop, and one or more post-reactors, not comprising recycle loops, wherein a recycle ratio in the one or more recycle loops is in a range of from 0.1 to 20.

11. The process according to claim 1 , further comprising before S3):
S1) providing or preparing a pre-catalyst composition comprising a mixture of oxides of copper and oxides of one or more metals other than copper,
wherein the pre-catalyst composition comprises oxides of copper in a total amount in a range of from 55 mass-% to 80 mass-%, relative to a total mass of the pre-catalyst composition;
and wherein the pre-catalyst composition comprises in addition to the oxides of copper:
p2) a carrier comprising oxides of silicon,
wherein a total amount of oxides of silicon in the pre-catalyst composition, relative to the total mass of the pre-catalyst composition, is in a range of from 3.0 mass-% to 35.0 mass-%;
and
p3) oxides of manganese, wherein a total amount of the oxides of manganese in the pre-catalyst composition, relative to the total mass of the pre-catalyst composition, is in a range of 0.5 mass-% to 5.0 mass-%,
and
oxides of one or more metal selected from the group consisting of sodium and calcium, wherein a total amount of the oxides of one or more metal selected from the group consisting of sodium and calcium, relative to the total mass of the pre-catalyst composition, is in a range of from 5.0 mass-% to 25.0 mass-%,

and
S2) reacting the pre-catalyst composition from step S1) with hydrogen at a temperature in a range of from 120° C. to 230° C.,
such that the catalyst composition comprising copper and one or more metal other than copper used in S3) results.

12. The process according to claim 11 , wherein
the pre-catalyst composition is present for at least a part of the process or process time as a formulation of solid particles selected from the group consisting of extrudates, tablets, pellets, strands, stars, powders, granules, granulates, and mixtures thereof;
and/o

Assignees

• Basf Se

Inventors

• Werner Albert
• Wentink Annebart
• Kokolakis Simon
• Weickgenannt Andreas
• Pinkos Rolf

Classifications

• B01J35/77

  Compounds characterised by their crystallite size · CPC title

• B01J35/50

  characterised by their shape or configuration · CPC title

• B01J35/32

  Bulk density · CPC title

• B01J2235/15

  X-ray diffraction · CPC title

• B01J23/8892

  Manganese · CPC title