New one-pot methods for preparation of cyclohexanecarbonitrile
– Green Chemistry metrics evaluation for one-pot and similar
multi-step syntheses

J 2014

New one-pot methods for preparation of cyclohexanecarbonitrile – Green Chemistry metrics evaluation for one-pot and similar multi-step syntheses

ŠIMBERA, Jan; Richard ŠEVČÍK a Pavel PAZDERA

Základní údaje

Originální název

New one-pot methods for preparation of cyclohexanecarbonitrile – Green Chemistry metrics evaluation for one-pot and similar multi-step syntheses

Autoři

ŠIMBERA, Jan; Richard ŠEVČÍK a Pavel PAZDERA

Vydání

Green and Sustainable Chemistry, Delaware, USA, Scientific Research Publishing, 2014, 2160-6951

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Kód RIV

RIV/00216224:14310/14:00074529

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.4236/gsc.2014.42011

Klíčová slova česky

Cyclohexanecarbonitrile; One-Pot Synthesis; EcoScale; EATOS; SIS; Synthesis of Organic Molecules; Catalysis; Green and Sustainable Chemistry; Waste Management AT SOURCE.

Klíčová slova anglicky

Cyclohexanecarbonitrile; One-Pot Synthesis; EcoScale; EATOS; SIS; Synthesis of Organic Molecules; Catalysis; Green and Sustainable Chemistry; Waste Management AT SOURCE.

Štítky

AKR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 13. 3. 2018 11:00, RNDr. Richard Ševčík, Ph.D.

Anotace

V originále

Three new multi-step one-pot processes for high-yielding cyclohexanecarbonitrile synthesis starting from cyclohexanone were developed for industrial application. In contrast to the current synthetic process all of the processes described were designed to proceed completely in methanol as a uniform solvent and the key oxidation step can be realized either as stoichiometric or catalytic. Atom efficiency of processes is rel-atively advanced with high regioselectivity, reaction by-products are either from environmental pool – carbon dioxide and nitrogen or they can be reused – sodium chloride. Solvent – methanol and other aux-iliaries – cyclohexane, copper catalyst can be reused after recycling as well. EcoScale for all three designed processes was evaluated and compared with current synthesis described in the past. Green chemistry metrics, including newly introduced evaluative tool – Sustainability Index of the Synthesis (SIS), were applied to evaluate design of described one-pot syntheses.

Návaznosti

2A-1TP1/090, projekt VaV

Název: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.

Investor: Ministerstvo průmyslu a obchodu ČR, Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy

Citovat

ŠIMBERA, Jan; Richard ŠEVČÍK a Pavel PAZDERA. New one-pot methods for preparation of cyclohexanecarbonitrile – Green Chemistry metrics evaluation for one-pot and similar multi-step syntheses. Green and Sustainable Chemistry. Delaware, USA: Scientific Research Publishing, 2014, roč. 2014, č. 4, s. 70-79. ISSN 2160-6951. Dostupné z: https://doi.org/10.4236/gsc.2014.42011.

@article{1188694,
   author = {Šimbera, Jan and Ševčík, Richard and Pazdera, Pavel},
   article_location = {Delaware, USA},
   article_number = {4},
   doi = {https://doi.org/10.4236/gsc.2014.42011},
   keywords = {Cyclohexanecarbonitrile; One-Pot Synthesis; EcoScale; EATOS; SIS; Synthesis of Organic Molecules; Catalysis; Green and Sustainable Chemistry; Waste Management AT SOURCE.},
   language = {eng},
   issn = {2160-6951},
   journal = {Green and Sustainable Chemistry},
   title = {New one-pot methods for preparation of cyclohexanecarbonitrile – Green Chemistry metrics evaluation for one-pot and similar multi-step syntheses},
   url = {http://dx.doi.org/10.4236/gsc.2014.42011},
   volume = {2014},
   year = {2014}
}

TY  - JOUR
ID  - 1188694
AU  - Šimbera, Jan - Ševčík, Richard - Pazdera, Pavel
PY  - 2014
TI  - New one-pot methods for preparation of cyclohexanecarbonitrile – Green Chemistry metrics evaluation for one-pot and similar multi-step syntheses
JF  - Green and Sustainable Chemistry
VL  - 2014
IS  - 4
SP  - 70-79
EP  - 70-79
PB  - Scientific Research Publishing
SN  - 21606951
KW  - Cyclohexanecarbonitrile
KW  - One-Pot Synthesis
KW  - EcoScale
KW  - EATOS
KW  - SIS
KW  - Synthesis of Organic Molecules
KW  - Catalysis
KW  - Green and Sustainable Chemistry
KW  - Waste Management AT SOURCE.
UR  - http://dx.doi.org/10.4236/gsc.2014.42011
L2  - http://dx.doi.org/10.4236/gsc.2014.42011
N2  - Three new multi-step one-pot processes for high-yielding cyclohexanecarbonitrile synthesis starting from cyclohexanone were developed for industrial application. In contrast to the current synthetic process all of the processes described were designed to proceed completely in methanol as a uniform solvent and the key oxidation step can be realized either as stoichiometric or catalytic. Atom efficiency of processes is rel-atively advanced with high regioselectivity, reaction by-products are either from environmental pool – carbon dioxide and nitrogen or they can be reused – sodium chloride. Solvent – methanol and other aux-iliaries – cyclohexane, copper catalyst can be reused after recycling as well. EcoScale for all three designed processes was evaluated and compared with current synthesis described in the past. Green chemistry metrics, including newly introduced evaluative tool – Sustainability Index of the Synthesis (SIS), were applied to evaluate design of described one-pot syntheses.
ER  -

ŠIMBERA, Jan; Richard ŠEVČÍK a Pavel PAZDERA. New one-pot methods for preparation of cyclohexanecarbonitrile – Green Chemistry metrics evaluation for one-pot and similar multi-step syntheses. \textit{Green and Sustainable Chemistry}. Delaware, USA: Scientific Research Publishing, 2014, roč.~2014, č.~4, s.~70-79. ISSN~2160-6951. Dostupné z: https://doi.org/10.4236/gsc.2014.42011.

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