Production method for indan and hydrindane

Patent metadata

Field	Value
Publication number	US-12331013-B2
Application number	US-202218270921-A
Country	US
Kind code	B2
Filing date	Jan 13, 2022
Priority date	Jan 15, 2021
Publication date	Jun 17, 2025
Grant date	Jun 17, 2025

Abstract

Provided is a production method for indan and hydrindane, including a reaction step of introducing a raw material composition including tetrahydroindene into a continuous reactor including a solid catalyst containing platinum, and bringing the raw material composition into contact with the solid catalyst under the conditions of 150° C. to 350° C. to obtain a reaction product including indan and hydrindane, in which the amount (mol/min) of hydrogen molecules is 5 times or less the amount (mol/min) of tetrahydroindene, and the amount (mol/min) of oxygen molecules is 0.1 times or less the amount (mol/min) of tetrahydroindene.

First claim

The invention claimed is:

1. A production method for indan and hydrindane, comprising:
reacting by introducing a raw material composition including 3a,4,7,7a-tetrahydroindene, optionally hydrogen molecules, and optionally oxygen molecules into a continuous reactor including a solid catalyst containing platinum, and bringing the raw material composition into contact with the solid catalyst under conditions of 150° C. to 350° C. to obtain a reaction product including indan and hydrindane,
wherein a ratio (C H2 /C 0 ) of an amount C H2 (mol/min) of the hydrogen molecules introduced into the continuous reactor per unit time with respect to an amount C 0 (mol/min) of the 3a,4,7,7a-tetrahydroindene introduced into the continuous reactor per unit time is 1 or less, and
a ratio (C O2 /C 0 ) of an amount C O2 (mol/min) of the oxygen molecules introduced into the continuous reactor per unit time with respect to an amount C 0 of the 3a,4,7,7a-tetrahydroindene introduced into the continuous reactor per unit time is 0.1 or less.

2. The production method according to claim 1 , wherein in the reacting, the raw material composition is brought into contact with the solid catalyst under conditions of 0.1 to 5.0 MPaG.

3. The production method according to claim 1 , wherein the solid catalyst contains a carrier and a supported metal supported on the carrier, and
the carrier includes aluminum, while the supported metal includes platinum.

4. The production method according to claim 3 , wherein a proportion occupied by platinum in the supported metal is 80% by mass or more.

5. The production method according to claim 3 , wherein the platinum is supported on the carrier by using a platinum source that includes no chlorine atom.

6. The production method according to claim 1 , wherein a content of 3a,4,7,7a-tetrahydroindene in the raw material composition is 5% by mass or more.

7. The production method according to claim 1 , wherein a mass ratio (C 1 /C 2 ) of a content C 1 of indan with respect to a content C 2 of hydrindane in the reaction product is 1.0 or more and 4.5 or less.

8. The production method according to claim 1 , wherein the reaction product further includes 3a,4,7,7a-tetrahydroindene, and a portion of the reaction product is reused as the raw material composition of the reacting.

9. The production method according to claim 1 , further comprising raw material synthesis by reacting butadiene with at least one selected from the group consisting of cyclopentadiene and dicyclopentadiene to obtain 3a,4,7,7a-tetrahydroindene.

Assignees

• Eneos Corp

Inventors

• Araki Yasuhiro
• Segawa Atsushi
• Iwasa Yasuyuki
• Ohuchi Tai
• Mayumi Kazuya
• YOSHIWARA Yukihiro

Classifications

• C07C5/48

  with oxygen as an acceptor · CPC title

• B01J23/42

  Platinum · CPC title

• C07C2602/08

  the other ring being five-membered, e.g. indane · CPC title

• C07C13/465

  Indenes; Completely or partially hydrogenated indenes · CPC title

• B01J35/51

  Spheres · CPC title