Process for the preparation of a bicyclic fused-ring alkane

Patent metadata

Field	Value
Publication number	US-10519081-B1
Application number	US-201816158326-A
Country	US
Kind code	B1
Filing date	Oct 12, 2018
Priority date	Jul 24, 2018
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

Abstract

A process for preparation of a bicyclic fused-ring alkane. In the presence of a bifunctional solid catalyst, one or more cyclitols undergo a C—C coupling reaction with itself or each other at a temperature and in a nitrogen gas atmosphere, to produce a bicyclic alkane precursor mixture; then, the nitrogen gas is replaced by hydrogen gas, and the bicyclic alkane precursor mixture is hydrogenated or hydrodeoxygenated at a temperature and under a pressure, to produce the bicyclic fused-ring alkane. The proportion of the bicyclic fused-ring alkane in the product as prepared according to the process is not lower than 80 wt %.

First claim

What is claimed is:

1. A process for preparation of a bicyclic fused-ring alkane, comprising:
producing a bicyclic alkane precursor mixture by a C—C coupling reaction of one or more compounds with itself or each other at a first temperature and in a nitrogen gas atmosphere in presence of a bifunctional solid catalyst;
then, replacing nitrogen gas of the nitrogen gas atmosphere by hydrogen gas, and hydrogenating or hydrodeoxygenating the bicyclic alkane precursor mixture at a second temperature and under a pressure, to produce the bicyclic fused-ring alkane, wherein
the one or more compounds is one or more selected from the group consisting of cyclopentanol, methyl cyclopentanol, dimethyl cyclopentanol, ethyl cyclopentanol, propyl cyclopentanol, cyclohexanol, methyl cyclohexanol, dimethyl cyclohexanol, ethyl cyclohexanol, propyl cyclohexanol, cycloheptanol, methyl cycloheptanol, dimethyl cycloheptanol, ethyl cycloheptanol, propyl cycloheptanol and 5-ethyl-3-methyl cycloheptanol,
the bifunctional solid catalyst is one or more selected from the group consisting of Pd/SAPO, CoMo/HY, Ni/HZSM-5, CuCo/Hβ, Ir/Al-SBA-15, PtNi/Al-SBA-16, Ru/Ti-MCM-41, Pt/H-ZSM-5, PdFe/H-ZSM-5, Au/LaY, Pt/Al-SBA-16 and Pt/Hβ,
an acidity —H 0 of the bifunctional solid catalyst is not lower than 3.5, and the bifunctional solid catalyst is added in an amount from 1 wt % to 20 wt % based on a total weight of reactants of the one or more compounds, and
the bicyclic fused-ring alkane is decalin or alkyl substituted decalin.

2. The process according to claim 1 , wherein, the acidity —H 0 of the bifunctional solid catalyst is in a range from 4.4 to 12.

3. The process according to claim 1 , wherein, the first temperature of the C—C coupling reaction ranges from 100° C. to 250° C.; the second temperature is in a range from 90° C. to 160° C., and the pressure of the hydrogen gas is in a range from 2 MPa to 6 MPa.

Assignees

• Univ Tianjin

Inventors

• Zou Jijun
• Nie Genkuo
• Pan Lun
• Zhang Xiangwen

Classifications

• C07C2602/28

  Hydrogenated naphthalenes · CPC title

• C07C2602/10

  the other ring being six-membered, e.g. tetraline · CPC title

• C07C2601/18

  with a ring being at least seven-membered · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C2601/14

  The ring being saturated · CPC title