The Highly Effective Hydrogenolysis-Based Debenzylation of Tetraacetyl-Dibenzyl-Hexaazaisowurtzitane (TADBIW) Using a Palladium/DOWEX Catalyst Having a Synergistic Effect

Kai Dong; Ying Chen; Yiying Zhang; Chenghui Sun; Siping Pang

doi:10.1080/07370652.2016.1267276

The Highly Effective Hydrogenolysis-Based Debenzylation of Tetraacetyl-Dibenzyl-Hexaazaisowurtzitane (TADBIW) Using a Palladium/DOWEX Catalyst Having a Synergistic Effect

Kai Dong, Ying Chen, Yiying Zhang, Chenghui Sun^*, Siping Pang

^*Corresponding author for this work

School of Material Science and Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

A Pd/resin catalyst system was prepared using a simple process and it exhibited excellent performance during the catalytic hydrogenolysis-based debenzylation of tetraacetyl-dibenzyl-hexaazaisowurtzitane (TADBIW) to 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (TAIW). Employing this system, the palladium concentration could be reduced from 1% to 0.4% while improving the yield from 92% to 98% under mild reaction conditions. These outstanding results can be attributed to a synergistic effect between the palladium and the acidic resin. A possible reaction mechanism is proposed for the acid-assisted removal of N-benzyl from TADBIW in the presence of this catalyst.

Original language	English
Pages (from-to)	421-429
Number of pages	9
Journal	Journal of Energetic Materials
Volume	35
Issue number	4
DOIs	https://doi.org/10.1080/07370652.2016.1267276
Publication status	Published - 2 Oct 2017

Keywords

Catalyst
TADBIW
debenzylation
hydrogenolysis
palladium/DOWEX

Access to Document

10.1080/07370652.2016.1267276

Cite this

@article{fafbde197e9f4b52ad581fc6da3b1b65,

title = "The Highly Effective Hydrogenolysis-Based Debenzylation of Tetraacetyl-Dibenzyl-Hexaazaisowurtzitane (TADBIW) Using a Palladium/DOWEX Catalyst Having a Synergistic Effect",

abstract = "A Pd/resin catalyst system was prepared using a simple process and it exhibited excellent performance during the catalytic hydrogenolysis-based debenzylation of tetraacetyl-dibenzyl-hexaazaisowurtzitane (TADBIW) to 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (TAIW). Employing this system, the palladium concentration could be reduced from 1% to 0.4% while improving the yield from 92% to 98% under mild reaction conditions. These outstanding results can be attributed to a synergistic effect between the palladium and the acidic resin. A possible reaction mechanism is proposed for the acid-assisted removal of N-benzyl from TADBIW in the presence of this catalyst.",

keywords = "Catalyst, TADBIW, debenzylation, hydrogenolysis, palladium/DOWEX",

author = "Kai Dong and Ying Chen and Yiying Zhang and Chenghui Sun and Siping Pang",

note = "Publisher Copyright: {\textcopyright} 2017 Taylor & Francis Group, LLC.",

year = "2017",

month = oct,

day = "2",

doi = "10.1080/07370652.2016.1267276",

language = "English",

volume = "35",

pages = "421--429",

journal = "Journal of Energetic Materials",

issn = "0737-0652",

publisher = "Taylor and Francis Ltd.",

number = "4",

}

TY - JOUR

T1 - The Highly Effective Hydrogenolysis-Based Debenzylation of Tetraacetyl-Dibenzyl-Hexaazaisowurtzitane (TADBIW) Using a Palladium/DOWEX Catalyst Having a Synergistic Effect

AU - Dong, Kai

AU - Chen, Ying

AU - Zhang, Yiying

AU - Sun, Chenghui

AU - Pang, Siping

PY - 2017/10/2

Y1 - 2017/10/2

N2 - A Pd/resin catalyst system was prepared using a simple process and it exhibited excellent performance during the catalytic hydrogenolysis-based debenzylation of tetraacetyl-dibenzyl-hexaazaisowurtzitane (TADBIW) to 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (TAIW). Employing this system, the palladium concentration could be reduced from 1% to 0.4% while improving the yield from 92% to 98% under mild reaction conditions. These outstanding results can be attributed to a synergistic effect between the palladium and the acidic resin. A possible reaction mechanism is proposed for the acid-assisted removal of N-benzyl from TADBIW in the presence of this catalyst.

AB - A Pd/resin catalyst system was prepared using a simple process and it exhibited excellent performance during the catalytic hydrogenolysis-based debenzylation of tetraacetyl-dibenzyl-hexaazaisowurtzitane (TADBIW) to 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (TAIW). Employing this system, the palladium concentration could be reduced from 1% to 0.4% while improving the yield from 92% to 98% under mild reaction conditions. These outstanding results can be attributed to a synergistic effect between the palladium and the acidic resin. A possible reaction mechanism is proposed for the acid-assisted removal of N-benzyl from TADBIW in the presence of this catalyst.

KW - Catalyst

KW - TADBIW

KW - debenzylation

KW - hydrogenolysis

KW - palladium/DOWEX

UR - http://www.scopus.com/inward/record.url?scp=85008187780&partnerID=8YFLogxK

U2 - 10.1080/07370652.2016.1267276

DO - 10.1080/07370652.2016.1267276

M3 - Article

AN - SCOPUS:85008187780

SN - 0737-0652

VL - 35

SP - 421

EP - 429

JO - Journal of Energetic Materials

JF - Journal of Energetic Materials

IS - 4

ER -

The Highly Effective Hydrogenolysis-Based Debenzylation of Tetraacetyl-Dibenzyl-Hexaazaisowurtzitane (TADBIW) Using a Palladium/DOWEX Catalyst Having a Synergistic Effect

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this