Efficient Base Nickel-Catalyzed Hydrogenolysis of Furfural-DerivedTetrahydrofurfuryl Alcohol to 1,5-Pentanediol

被引：33

作者：

Al-Yusufi, Mohammed ^{[1
]}

Steinfeldt, Norbert ^{[1
]}

Eckelt, Reinhard ^{[1
]}

Atia, Hanan ^{[1
]}

Lund, Henrik ^{[1
]}

Bartling, Stephan ^{[1
]}

Rockstroh, Nils ^{[1
]}

Koeckritz, Angela ^{[1
]}

机构：

[1] Leibniz Inst Catalysis LIKAT, D-18059 Rostock, Germany

来源：

ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2022年 / 10卷 / 15期

关键词：

1; 5-pentanediol; hydrogenolysis; transfer hydrogenolysis; ring opening; nickel; lanthanide hydroxide; furfural; tetrahydrofurfuryl alcohol; C-O HYDROGENOLYSIS; TETRAHYDROFURFURYL ALCOHOL; SELECTIVE HYDROGENOLYSIS; CYCLIC ETHERS; CHEMOSELECTIVE HYDROGENOLYSIS; BIOMASS; METAL; OXIDE; HYDROGENATION;

D O I：

10.1021/acssuschemeng.1c08340

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nickel(0) supported by strongly basic lanthanidehydroxides/oxyhydroxides (Ni-Ln, Ln = La, Pr, and Sm) is anefficient alternative noble metal-free catalyst for hydrogenolysis oftetrahydrofurfuryl alcohol (THFA) to 1,5-pentanediol (1,5-PeD) inorganic solvents (e.g., isopropanol). The catalytic performance ofNi-Lnwas studied both in batch and continuous modes. The highestyield of 1,5-PeD was 88% in a batch system and 73% in aflow systemusing40Ni-La reduced. Interestingly,40Ni-La reducedwas not onlyselective (>= 84%) but also stable in a long-term continuous run (386h). It is proposed that a metal support interface (Ni-Ln)isresponsible for cleaving the C-O bond of THFA via two initialsteps: deprotonation of THFA and activation of hydrogen. Addition-ally, transfer hydrogenolysis took place in the presence of H2insecondary alcohols, resulting in higher yields of 1,5-PeD under batch conditions. However, addition of H2had almost no influenceon catalyst selectivity to 1,5-PeD underflow conditions.

引用

页码：4954 / 4968

页数：15

共 51 条

[1]

Adkins H., 1931, J. Am. Chem. Soc, V53, P1091, DOI DOI 10.1021/JA01354A041

[2] THERMODYNAMIC PROPERTIES OF ORGANIC OXYGEN COMPOUNDS .9. CRITICAL PROPERTIES AND VAPOUR PRESSURES, ABOVE 5 ATMOSPHERES, OF ALIPHATIC ALCOHOLS [J].

AMBROSE, D ;

TOWNSEND, R .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (JUL) :3614-&

[3] Recent advances in the catalytic transfer hydrogenation of furfural to furfuryl alcohol over heterogeneous catalysts [J].

An, Zhidong ;

Li, Jiang .

GREEN CHEMISTRY, 2022, 24 (05) :1780-1808

[4]

[Anonymous], 2021, 1 4 BUT BDO MARK SHA

[5] Resolving surface chemical states in XPS analysis of first row transition metals, oxides and hydroxides: Cr, Mn, Fe, Co and Ni [J].

Biesinger, Mark C. ;

Payne, Brad P. ;

Grosvenor, Andrew P. ;

Lau, Leo W. M. ;

Gerson, Andrea R. ;

Smart, Roger St. C. .

APPLIED SURFACE SCIENCE, 2011, 257 (07) :2717-2730

[6] X-ray photoelectron spectroscopic chemical state quantification of mixed nickel metal, oxide and hydroxide systems [J].

Biesinger, Mark C. ;

Payne, Brad P. ;

Lau, Leo W. M. ;

Gerson, Andrea ;

Smart, Roger St. C. .

SURFACE AND INTERFACE ANALYSIS, 2009, 41 (04) :324-332

[7] SOLUBILITY OF HYDROGEN IN ALCOHOLS [J].

BRUNNER, E .

BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1979, 83 (07) :715-721

[8] An attempt to achieve the direct hydrogenolysis of tetrahydrofurfuryl alcohol in supercritical carbon dioxide [J].

Chatterjee, Maya ;

Kawanami, Hajime ;

Ishizaka, Takayuki ;

Sato, Masahiro ;

Suzuki, Toshishige ;

Suzuki, Akira .

CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (08) :1466-1471

[9] C-O bond hydrogenolysis of cyclic ethers with OH groups over rhenium-modified supported iridium catalysts [J].

Chen, Kaiyou ;

Mori, Kazuma ;

Watanabe, Hideo ;

Nakagawa, Yoshinao ;

Tomishige, Keiichi .

JOURNAL OF CATALYSIS, 2012, 294 :171-183

[10] Chemoselective Hydrogenolysis of Tetrahydropyran-2-methanol to 1,6-Hexanediol over Rhenium-Modified Carbon-Supported Rhodium Catalysts [J].

Chen, Kaiyou ;

Koso, Shuichi ;

Kubota, Takeshi ;

Nakagawa, Yoshinao ;

Tomishige, Keiichi .

CHEMCATCHEM, 2010, 2 (05) :547-555

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