Subscribe to RSS

DOI: 10.1055/a-2243-0268
Continuous Flow Multigram-Scale Synthesis of Cetylpyridinium Chloride

Abstract
Cetylpyridinium chloride is popularly employed as an antimicrobial agent in high-volume commodity and consumer products. Given its high tonnage requirements annually, challenges in its synthesis using conventional batch manufacturing involving higher reaction temperatures at scale, lower yields and purity, and excessively long reaction times could be circumvented by adopting continuous flow as a safe and sustainable approach. We herein report a facile, gram-scale continuous flow protocol for the synthesis of cetylpyridinium chloride (CPC) that reduces reaction time from ≥24 hours to 30 minutes with an isolated product yield of >90% and an HPLC purity of >99%.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2243-0268.
- Supporting Information
Publication History
Received: 22 October 2023
Accepted after revision: 10 January 2024
Article published online:
25 January 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
Kashyap Patel, Anant R. Kapdi, Manish Manohar Shinde, Karuna Veeramani, Srinivas Oruganti. Continuous Flow Multigram-Scale Synthesis of Cetylpyridinium Chloride. Sustainability & Circularity NOW 2024; 01.
DOI: 10.1055/a-2243-0268
-
References
- 1
Zhou Z,
Zhou S,
Zhang X,
Zeng S,
Xu Y,
Nie W,
Zhou Y,
Xu T,
Chen P.
Bioconjugate Chem. 2023; 34: 302-325
MissingFormLabel
- 2a
Mao X,
Auer DL,
Buchalla W,
Hiller K.-A,
Maisch T,
Hellwig E,
Al-Ahmad A,
Cieplik F.
Antimicrob. Agents Chemother. 2020; 64: e00576-20
MissingFormLabel
- 2b
D’Amico F,
Moro M,
Saracino M,
Marmiere M,
Cilona MB,
Lloyd-Jones G,
Zangrillo A.
Mol. Oral Microbiol. 2023; 38: 171-180
MissingFormLabel
- 3
Lopes JS,
Cosate de Andrade MF,
Morales AR.
J. Polym. Environ. 2023; 31: 4703-4713
MissingFormLabel
- 4
Teoman B,
Muneeswaran ZP,
Verma G,
Chen D,
Brinzari TV,
Almeda-Ahmadi A,
Norambuena J,
Xu S,
Ma S,
Boyd JM,
Armenate PM,
Potanin A,
Pan L,
Asefa T,
Dubovoy V.
ACS Omega 2021; 6: 35433-35441
MissingFormLabel
- 5
Knight GA,
Shaw BD.
J. Chem. Soc. 1938; 682-683
MissingFormLabel
- 6a
Shelton S,
van Campen MG,
Tilford CH,
Lang HC,
Nisonger L,
Bandelin FJ,
Rubenkoenig HL.
J. Am. Chem. Soc. 1946; 68: 753-755
MissingFormLabel
- 6b
Shelton S,
van Campen MG,
Tilford CH,
Lang HC,
Nisonger L,
Bandelin FJ,
Rubenkoenig HL.
J. Am. Chem. Soc. 1946; 68: 757-759
MissingFormLabel
- 7
Barni E,
Savarino P,
Larovere R,
Viscardi G,
Pelizzetti E.
J. Het. Chem. 1986; 23: 209-221
MissingFormLabel
- 8
Buszka M,
Slezak T.
Polish Patent PL149740B1, 1986
MissingFormLabel
- 9
Sano K,
Urano Y,
Kimura T,
Sano A.
European Patent EP1125927B1, 2001
MissingFormLabel
- 10
Su W.-Y.
US patent US5041664A, 1990
MissingFormLabel
- 11
Shiqun S,
Fan S,
Yuguo X.
Chinese patent CN103539727A, 2013
MissingFormLabel
- 12
Pandey A,
Pandey SP,
Verma PK,
Agrawal A.
PCT Application WO2016092499A1, 2015
MissingFormLabel
- 13a
Guidi M,
Seeberger PH,
Gilmore K.
Chem. Soc. Rev. 2020; 49: 8910-8932
MissingFormLabel
- 13b
Plutschack MB,
Pieber B,
Gilmore K,
Seeberger PH.
Chem. Rev. 2017; 117: 11796-11893
MissingFormLabel
- 14
Gambacorta G,
Sharley JS,
Baxendale IR.
Beilstein J. Org. Chem. 2021; 17: 1181-1312
MissingFormLabel
- 15a
Noel T,
Cao Y,
Laudadio G.
Acc. Chem. Res. 2019; 52:
2858-2869
MissingFormLabel
- 15b
Kobayashi S.
Chem. Asian J. 2016; 11: 425-436
MissingFormLabel
- 15c
Muschelknautz S,
Wellenhofer A.
Chem. Eng. Technol. 2003; 26:
797-803
MissingFormLabel
- 15d
Gutmann B,
Cantillo D,
Kappe CO.
Angew. Chem. Int. Ed. 2015; 54: 6688-6728
MissingFormLabel
- 16a
Spennacchio M,
Colella M,
Andresini M,
Dibenedetto RS,
Graziano E,
Aramini A,
Degennaro L,
Luisi R.
Chem. Commun. 2023; 59: 1373-1376
MissingFormLabel
- 16b
Colella M,
Nagaki A,
Luisi R.
Chem. Eur. J. 2020; 26: 19-32
MissingFormLabel
- 16c
Razzaq T,
Kappe CO.
Chem. Asian J. 2010; 5: 1274-1289
MissingFormLabel
- 17a
Ley SV,
Chen Y,
Robinson A,
Otter B,
Godineau E,
Battilocchio C.
Org. Process Res. Dev. 2021; 25: 713-720
MissingFormLabel
- 17b
Pastre JC,
Murray PR. D,
Browne DL,
Brancaglion GA,
Galaverna RS,
Pilli RA,
Ley SV.
ACS Omega 2020; 5:
18472-18483
MissingFormLabel
- 17c
Watanabe E,
Chen Y,
May O,
Ley SV.
Chem. Eur. J. 2020; 26: 186-191
MissingFormLabel
- 18a
Bianchi P,
Williams JD,
Kappe CO.
J. Flow Chem. 2020; 10:
475-490
MissingFormLabel
- 18b
Dallinger D,
Gutmann B,
Kappe CO.
Acc. Chem. Res. 2020; 53: 1330-1341
MissingFormLabel
- 19a
Wen Z,
Pintossi D,
Nuno M,
Noël T.
Nat. Commun. 2022; 13: 6147
MissingFormLabel
- 19b
Bajada MA,
Sanjosé-Orduna J,
Di Liberto G,
Tosoni S,
Pacchioni G,
Noël T,
Vilé G.
Chem. Soc. Rev. 2022; 51:
3898-3925
MissingFormLabel
- 19c
Mazzarella D,
Pulcinella A,
Bovy L,
Broersma R,
Noël T.
Angew. Chem. Int. Ed. 2021; 60: 21277-21282
MissingFormLabel
- 20
Breen CP,
Nambiar AM. K,
Jamison TF,
Jensen KF.
Trends Chem. 2021; 3: 373-386
MissingFormLabel
- 21a
van Melis CG. W,
Penny MR,
Garcia AD,
Petti A,
Dobbs AP,
Hilton ST,
Lam K.
ChemElectroChem 2019; 6: 4144-4148
MissingFormLabel
- 21b
Penny MR,
Rao ZX,
Peniche BF,
Hilton ST.
Eur. J. Org. Chem. 2019; 3783-3787
MissingFormLabel
- 22
Hayashi Y.
Acc. Chem. Res. 2021; 54: 1385-1398
MissingFormLabel
- 23
Gaware S,
Kori S,
Serrano JL,
Dandela R,
Hilton S,
Sanghvi YS,
Kapdi AR.
J. Flow Chem. 2023; 13: 293-310
MissingFormLabel
- 24a
Oruganti S,
Vijaykumar BV. D,
Manudhane KS,
Nalluri S,
Shende CA,
Uppada MK.
Continuous flow process for the preparation of polymerizable cationic monomer derivatives
and precursors thereof. Indian Patent No. 435339, 2020
MissingFormLabel
- 24b
Shukla CA,
Udaykumar B,
Saisivanarayana Y,
Ismaili A,
Haripriya T,
Shinde M,
Neti S,
Uppada M,
Eda V,
Sen S,
Oruganti S.
J. Flow. Chem. 2022; 12: 1-7
MissingFormLabel
- 24c
Veeramani K,
Shinde M,
Eda VV. R,
Darapaneni BC,
Hindupur RM,
Madarapu SR,
Sen S,
Oruganti S.
Tetrahedron Lett. 2023; 116 154344
MissingFormLabel