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Chris Rayner

Professor of Organic Chemistry
Member of the Process Research and Development group

Contact details

Room: G52d
Tel: +44 (0)113 3436579
Email: C.M.Rayner@leeds.ac.uk

Keywords

Chemistry in supercritical carbon dioxide
Capture and reactions of carbon dioxide
Synthetic photochemistry
Continuous reactions and reactors
Environmentally friendly coloration technology and polymerisation
Natural product synthesis and utilisation
Complex polyamines and their interactions with biomolecules

Photograph of Chris Rayner

Research interests

My research is in the following main areas:

The Chemistry of Carbon Dioxide.
We have been working on utilising carbon dioxide in synthetic organic chemistry and related applications for over 15 years. The current importance of CO2 and its chemistry cannot be overstated, and we have a range of important projects underway which include using supercritical CO2 as a solvent for pharmaceutical synthesis, utilisation of CO2 in novel crystallisation processes(with Prof. Kevin Roberts (School of Process, Environmental and Materials Engineering, University of Leeds), conversion of CO2 into C-1 building blocks (e.g. formic acid); and novel CO2 capture processes for sequestration and storage applications. We also have a joint project with Professor M. Arai (Hokkaido University) to determine the importance of fundamental interactions between CO2 and solutes in controlling reactions in CO2.

Novel reactor chemistry
Following on from our expertise in carrying out reactions in supercritical CO2, we are also interested in other ways of carrying out organic chemistry. A key aspect of this is to carry out reactions continuously rather than in a batch reaction. This allows a range of reactions to be carried out which are not feasible in a conventional batch reactor, but are capable of producing large amounts of material in continuous mode, and this work is particularly relevant to fine chemical and pharmaceutical process chemistry. Typical examples include novel photochemical and microwave accelerated processes, including polymerisation reactions (with Prof. Sebastien Perrier, University of Sydney).

New coloration technology
In collaboration with Dr Richard Blackburn (Centre for Technical Textiles, University of Leeds) and Dr Patrick McGowan (School of Chemistry, University of Leeds) we have a range of projects underway which focus on environmentally and user friendly coloration methods. This can involve the use and/or modification of natural dyes for specific consumer applications, or for the production of biodegradable and renewable (i.e. not from petrochemicals) coloured polymers (e.g. poly-lactic acid) of the future. Much of this work is carried out in conjunction with our University spin-out company, DyeCat Ltd.

Reactive intermediate chemistry
Reactive intermediates such as aziridinium ions are being exploited for the synthesis of polyamines capable of interacting selectively with nucleic acids (with Prof. Peter Stockley (Astbury Centre, University of Leeds)).

I am also very interested in teaching at the Chemistry - Chemical Engineering interface to enhance the effectiveness of research collaborations between chemists and chemical engineers. We run a 3 day short course, Chemistry for Chemical Engineers, accredited by the IChemE, designed to facilitate such interactions. From September 2008, as part of the recently established Institute for Process Research and Development will lead a new MSc in Chemical Process Research and Development in collaboration with colleagues from the School of Process, Environmental and Materials Engineering.

Useful links

DyeCat   
Chemistry for Chemical Engineers   
Institute of Process Research and Development   

Publications

Henderson RL; Rayner CM; Blackburn RS Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation. Phytochemistry 95 105-108, 2013
DOI:10.1016/j.phytochem.2013.07.001
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Wang M; Ramskill NP; Barns S; Raynel G; Qiu C; Rayner CM A feasible process tomography and spectroscopy measurement system to determine carbon dioxide absorption Flow Measurement and Instrumentation 31 77-85, 2013
DOI:10.1016/j.flowmeasinst.2012.09.005
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Wang M; Ramskill NP; Barns S; Rayner CM; Raynel G; Qiu C A feasible process tomography and spectroscopy measurement system to determine carbon dioxide absorption Flow Measurement and Instrumentation -, 2012
DOI:10.1016/j.flowmeasinst.2012.09.005
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Blackburn RS; McGowan PC; Pask CM; Rayner CM CATALYSED DYE SYSTEMS, 2011
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Macrae RO; Pask CM; Burdsall LK; Blackburn RS; Rayner CM; McGowan PC Backside Cover: The Combined Synthesis and Coloration of Poly(lactic acid) (Angew. Chem. Int. Ed. 1/2011)., 2011
DOI:10.1002/anie.201006804

Drivas I; Blackburn RS; Rayner CM Natural anthraquinonoid colorants as platform chemicals in the synthesis of sustainable disperse dyes for polyesters DYES PIGMENTS 88 7-17, 2011
DOI:10.1016/j.dyepig.2010.04.009

Blackburn RS; Rose PM; Rayner CM NATURAL HAIR DYES, 2010
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Rayner CM; Rose PM; Barnes DC Synthetic organic chemistry in supercritical fluids In Handbook of Green Chemistry , 2010
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Blackburn RS; McGowan PC; Pask CM; Rayner CM Combined Synthesis and Coloration of Poly(lactic acid) - The DyeCat Process, 2009

Dharmayat S; Hammond RB; Kilner C; Lai XJ; Palmer RA; Potter BS; Rayner CM; Roberts KJ Comparison of the crystal chemistry, the process conditions for crystallization and the relative structural stability of two polymorphic forms of N-G-monomethyl-L-arginine hydrochloride ORG PROCESS RES DEV 12 860-868, 2008
DOI:10.1021/op700171b

Akiyama Y; Fujita S; Senboku H; Rayner CM; Brough SA; Arai M An in situ high pressure FTIR study on molecular interactions of ketones, esters, and amides with dense phase carbon dioxide J SUPERCRIT FLUID 46 197-205, 2008
DOI:10.1016/j.supflu.2008.03.009

Dharmayat S; Hammond RB; Lai X; Roberts KJ; Kilner CA; Rayner CM Comparison of the crystal chemistry the process conditions for crystallization and the relative structural stability of two polymorphic forms of NG-monomethyl L-Arginine hydrochloride Organic Process Research and Development pp.1-, 2008
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Rayner CM; Oakes RS; Sakakura T; Yasuda H Supercritical Carbon Dioxide, 2007
DOI:10.1002/9780470988770.ch4

Blackburn RS; Rayner CM; Pask CM; McGowan PC Novel catalytic materials and their use in the preparation of colored polymeric materials, 2007
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Brown SL; Rayner CM; Graham S; Cooper A; Rannard SP; Perrier S Ultra-fast microwave enhanced reversible addition-fragmentation chain transfer (RAFT) polymerization: monomers to polymers in minutes Chemical Communications 21 2145-2147, 2007
DOI:10.1039/b703386a
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Rayner CM; Brown SL; Perrier S Microwave-accelerated RAFT polymerization of polar monomers Macromolecular Rapid Communications 28 478-483, 2007

Scanlon S; Aggeli A; Boden N; Koopmans R; Brydson R; Rayner CM peptide aerogels comprising self-assembling nanofibrils Micro&Nano Letters 24-29, 2007

Brown SL; Rayner CM; Graham S; Cooper A; Rannard S; Perrier S Ultra-fast microwave enhanced reversible addition-fragmentation chain transfer (RAFT) polymerization: Monomers to polymers in minutes Chemical Communications 2145-2147, 2007
DOI:10.1039/b703386a
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Rayner CM The potential of carbon dioxide in synthetic organic chemistry ORG PROCESS RES DEV 11 121-132, 2007
DOI:10.1021/op060165d

Saffarzadeh-Matin S; Kerton FM; Lynam JM; Rayner CM Formation and catalytic activity of Pd nanoparticles on silica in supercritical CO2 GREEN CHEM 8 965-971, 2006
DOI:10.1039/b607118j

Murray BS; Dickinson E; Clarke DA; Rayner CM Stabilization of carbon dioxide-in-water emulsions by proteins CHEM COMMUN 1410-1412, 2006
DOI:10.1039/b515700e

McGowan PC; Rayner CM; Blackburn RJ Novel catalytic materials and their use in the preparation of polymeric materials, 2005

Rayner CM; Oakes R; Sakakura T; Yasuda H Supercritical Carbon Dioxide in 'Green Reaction Media in Organic Synthesis In Green Reaction Media in Organic Synthesis , 2005

Saffarzadeh-Matin S; Chuck CJ; Kerton F; Rayner CM Poly(dimethylsiloxane)-derived phosphine and phosphinite ligands: Synthesis, characterization, solubility in supercritical carbon dioxide, and sequestration on silica Organometallics 23 5176-5181, 2004
DOI:10.1021/om0496277

Kuiper JL; Shapley PA; Rayner CM Synthesis, structure, and reactivity of the ruthenium(VI)-nickel(II) complex (dppe)Ni(mu(3)-S)(2){Ru(N)Me-2}(2) Organometallics 23 3814-3818, 2004
DOI:10.1021/om034373v

McKay C; Wilson RJ; Rayner CM An iterative approach to novel polyamines via nucleophilic ring-opening of aziridinium ions with beta-amino alcohols CHEM COMMUN 1080-1081, 2004
DOI:10.1039/b401447b

McKay C; Wilson RJ; Rayner CM An iterative approach to novel polyamines via nucleophilic ring-opening of aziridinium ions with beta-amino alcohols. Chemical communications (Cambridge, England) 1080-1081, 2004
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Rayner CM; Martin C Phenylselenyl chloride In Encyclopaedia of Reagents for Oganic Synthesis , 2004

Clarke D; Ali MA; Clifford AA; Parratt AJ; Rose PM; Schwinn D; Bannwarth W; Rayner CM Reactions in unusual media None 4 729-771, 2004

Rayner CM; Martin C; Hernan AG Triphenylphosphine In Electronic Encyclopaedia of Reagents for Organic Synthesis , 2004

Parratt AJ; Adams DJ; Clifford AA; Rayner CM Manipulation of the stereochemical outcome and product distribution in the Henry reaction using CO2 pressure CHEM COMMUN 2720-2721, 2004
DOI:10.1039/b409451d

Forristal I; Lawson KR; Rayner CM Stereoselective conjugate addition of thiolate nucleophiles to (E)-γ-hydroxyα,β-unsaturated sulfoxides and sulfones Sulfur Letters 26 89-94, 2003
DOI:10.1080/0278611031000104989
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Graham MA; Wadsworth AH; Zahid A; Rayner CM Studies on the Lewis acid mediated cleavage of alpha-aminoacetals: synthesis of novel 1,2-aminoethers, and evidence for alpha-alkoxy aziridinium ion intermediates ORG BIOMOL CHEM 1 834-849, 2003
DOI:10.1039/b210116e

Rayner CM; Forristal I; Lawson KR “Stereselective conjugate addition of thiolate nucleophiles to (E)-g-hydroxy-a,b-unsaturated sulfoxides and sulfones Sulfur Letters 26 -, 2003

Clifford AA; Rose PM; Lee K; Rayner CM Thermodynamics of the Baylis-Hillman reaction in supercritical carbon dioxide, 2003
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Clifford AA; Rose PM; Lee K; Rayner CM Thermodynamics of reactions in carbon dioxide. ABSTR PAP AM CHEM S 223 U670-U670, 2002

Clifford AA; Rose PM; Lee K; Rayner CM Thermodynamics of reactions in carbon dioxide, 2002

Shezad N; Clifford AA; Rayner CT Pd-catalysed coupling reactions in supercritical carbon dioxide and under solventless conditions Special Publication - Royal Society of Chemistry 4 64-67, 2002

Rose PM; Clifford AA; Rayner CM The Baylis-Hillman reaction in supercritical carbon dioxide: enhanced reaction rates, unprecedented ether formation, and a novel phase-dependent 3-component coupling CHEM COMMUN 968-969, 2002
DOI:10.1039/b111347j

Graham MA; Wadsworth AH; Thornton-Pett MA; Rayner CM Tandem cationic cyclisation–aziridinium ion formation–nucleophilic ring opening: new methodology for the stereocontrolled synthesis of substituted pyrrolidines Chemical Communications 11 966-967, 2001
DOI:10.1039/b102124i

Graham MA; Wadsworth AH; Thornton-Pett M; Carrozzini B; Cascarano GL; Rayner CM Mechanistic and stereochemical aspects of the Lewis acid mediated cleavage of alpha-aminoacetals TETRAHEDRON LETT 42 2865-2868, 2001

Shezad N; Clifford AA; Rayner CM Suppression of double bond isomerisation in intramolecular Heck reactions using supercritical carbon dioxide TETRAHEDRON LETT 42 323-325, 2001

Rayner CM; Clifford AA; Shezad N Suppression of double bond isomerisation in intramolecular Heck reactions using supercritical carbon dioxide Tetrahedron Letters 42 323-326, 2001
DOI:10.1016/S0040-4039(00)01917-1

Rayner CM Catalysis in Supercritical Carbon Dioxide What Advantages does it have to Offer? Journal of Labelled Compounds and Radiopharmaceuticals pp.312-, 2001

Rayner CM; Graham M Product class 4; benzo[b]thiophens Science of Synthesis 155-184, 2001

Shezad N; Oakes R; Clifford AA; Rayner CM Pd-catalyzed coupling reactons in supercritical carbon dioxide Chemical Industries 82 459-464, 2001

Oakes RS; Clifford AA; Rayner CM The use of supercritical fluids in synthetic organic chemistry J CHEM SOC PERK T 1 917-941, 2001
DOI:10.1039/b101219n

Shezad N; Oakes R; Clifford AA; Rayner CM Use of fluorinated palladium sources for efficient Pd-catalysed coupling reactions in supercritical carbon dioxide. Tetrahedron Letters 40 2221-2224, 1999

Oakes R; Clifford AA; Bartle KD; Thornton-Pett MA; Rayner CM Sulfur oxidation in supercritical carbon dioxide: dramatic pressure dependant enhancement of diastereoselectivity for sulfoxidation of cysteine derivatives Chemical Communications 3 247-248, 1999

Fletcher SJ; Rayner CM Enzymatic resolution ofα -acetoxyethers: A new approach to the synthesis of homochiral O,O-acetals Tetrahedron Letters 40 7139-7142, 1999

Clifford AA; Pople K; Gaskill WJ; Bartle KD; Rayner CM Potential tuning and reaction control in the Diels-alder reaction between cyclopentadiene and methyl acrylate in supercritical fluid carbon dioxide Faraday Transactions 94 1451-1456, 1998

Rayner CM Lewis acid induced rearrangement of 1-Hetero-2,3-Epoxides. Synthesis, reactivity and synthetic applications of homochiral thiiranium and aziridinium ion intermediates. Synlett 1 11-21, 1997

Rayner CM; Liu Q; Marchington AP; Boden N Generation of homochiral aziridinium ion intermediates derived from 2,3-epoxy amines: regiospecific nucleophilic trapping with nitrogen nucleophiles. Application in the synthesis of novel morpholinosphingolipid analogues with potential glucosyl ......... Royal Society of Chemistry. Journal: Perkin Transactions 1 511-525, 1997

Rayner CM; Blackburn RS; McGowan PC; Pask CM Catalyzed dye systems for textile fibers or hair.,
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Rayner CM; Blackburn RS Natural hair dyes comprising polyphenols.,
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Rayner CM; Raynel GRJ; Bala S Process for the capture of carbon dioxide.,
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Rayner CM; Raynel GRJ Process for the Capture of Carbon Dioxide,
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