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Identification of Rosin and Rosin Derivatives

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Identification of Rosin and Rosin Derivatives H4R CONSORTIUM Reference Document on the Identification of Rosin and Rosin Derivatives 1 Sponsored by the H4R Consortium December 2012 Notice Please read this notice carefully before using the “Reference Document on the Identification of Rosin and Rosin Derivatives” provided by H4R (“Document”). This Document has been prepared by H4R Consortium, who has decided to make it available to interested parties for their information. .Note however, that this document is made available “as is” and “for what it may be worth.” It is not intended to provide counsel, guidance or advice. Before you make any use of this document, you must decide whether it is appropriate for you and whether you are willing and ready to assume any risk inherent in its use. The H4R Consortium service providers and its members do not make any representation or provide any warranty, whether explicit or implied, with respect to this Document nor accept any responsibility or liability for any statements, deficiencies, omissions or other shortcomings in this Document. If you do not agree with any of the above disclaimers and limitations, you may not make any use of the Document. 1 c/o Penman Consulting bvba, Rue Royale 157 Bte 13, 1210 Brussels, Belgium http://www.h4rconsortium.com/ Reference Document on the Identification of Rosin and Rosin derivatives Executive Summary The different analytical techniques commonly used in regulatory fora have been reviewed for their utility in determining the identification and composition of rosin and its derivatives. There is no single analytical technique available that identifies the chemical nature of the rosin or rosin derivatives. Only by combining techniques and also knowing the chemical process applied, can the identity and composition be established to the maximum extent possible. From this review the following analyses are recommended. Table 1 - Overview of analyses Rosin, Rosin adducts Rosin Category / hydrogenated Rosin adduct Section Rosin esters and rosin Information rosin and their esters adducts salts salts Infra-Red 2.1 + + + + UV-VIS 2.2 + + + + 1H-NMR 2.3 + + + + 13C-NMR 2.4 - - - - Chromatography GC 2.4.1 + - + - HPLC 2.4.2 - - - - SEC 2.4.2 - + - + Mass spectrometry* LCMS + + - + Fragmentation MS - - + - 2.5 MALDI / - - - - Electrospray *Not a routine technique for these types of substances This document gives reference values and also an example of good practice when reporting the data. December 2012 Page 1 of 106 Reference Document on the Identification of Rosin and Rosin derivatives Contents Executive Summary ................................................................................................................................... 1 1. Introduction ...................................................................................................................................... 3 2. Review of analytical techniques for rosin and rosin derivatives ...................................................... 5 2.1 Infra-Red spectroscopy ............................................................................................................. 5 2.2 UV-VIS ....................................................................................................................................... 8 2.3 1H-NMR ................................................................................................................................... 11 2.4 13C-NMR .................................................................................................................................. 21 2.5 Chromatography ..................................................................................................................... 23 2.5.1 Gas chromatography (GC) ................................................................................................... 23 2.5.2 Liquid Chromatography ...................................................................................................... 25 2.6 Mass spectrometry ................................................................................................................. 28 2.7 Acid value ................................................................................................................................ 37 3. Manufacturing: ............................................................................................................................... 38 3.1 Rosin ........................................................................................................................................ 38 3.2 Hydrogenated rosin ................................................................................................................ 38 3.3 Rosin esters ............................................................................................................................. 38 3.4 Rosin adducts & Rosin adduct salts ........................................................................................ 38 3.5 Rosin adduct, esters ................................................................................................................ 41 3.5.1 Rosin, formaldehyde adduct ............................................................................................... 41 4. Conclusions ......................................................................................................................................... 41 Appendix 1 - Reference IR Spectra.......................................................................................................... 43 Appendix 2 - Reference Spectra UV-VIS.................................................................................................. 47 Appendix 3 – NMR .................................................................................................................................. 48 Appendix 4 - Mass spectra for specific rosin acid methyl esters .......................................................... 104 December 2012 Page 2 of 106 Reference Document on the Identification of Rosin and Rosin derivatives 1. Introduction Rosin is obtained from pine trees and consists of hundreds of components. The variation in the ratio of the components is caused, amongst others, by geographical as well as climatic differences (see Table 1 below). For this reason rosin and its derivatives from industrial processes based on rosin are UVCB’s. The question arises as to how to demonstrate that the substance used in testing (phys/chem, tox and ecotox) is indeed the substance that has been registered. As we will see below, there is no single analytical technique available that identifies the chemical nature of the rosin or rosin derivatives. Only by combining techniques and also knowing the chemical process applied, can the identity and composition be established to the maximum extent possible. This document is intended to give guidelines on the identification of rosin and rosin derivatives. December 2012 Page 3 of 106 Reference Document on the Identification of Rosin and Rosin derivatives Table 2Principal Resin Acids Source: Naval Stores, 1989, editors Duane F. Zinkel and James Russell, ISBN 0-9600416-2-5 December 2012 Page 4 of 106 Reference Document on the Identification of Rosin and Rosin derivatives 2. Review of analytical techniques for rosin and rosin derivatives 2.1 Infra-Red spectroscopy IR spectroscopy can be used to provide an overview of some functional groups and has specific profile dependent upon the rosin derivative. Analysis of the IR spectrum shows some items that are noteworthy: - The O-H stretch vibration at ~3500 cm-1 is only visible in the esters, not in rosin or hydrogenated rosin. The intensity of the peak could be caused by excess alcohol or incomplete esterification of the polyol (ratio of mono-, di-, tri- and/or tetra-ester may vary). - The O-H stretch vibration of the acid group is visible as a very broad band from 3500 – 2500 cm-1 (dotted, curved line in the spectra below) with two weak absorptions at 2652 and 2528 cm-1, which do not appear in any of the spectra of the esters. - The C=O stretch vibration in the acid group absorbs at a lower wavenumber (1690-1700 cm-1) than in the esters (1715-1735 cm-1). The C=O stretch vibration region for the metal salts of rosin acids need special attention. Remarkable are the two absorptions in the regions in the range of 1520 – 1550 (strong) and 1620 – 1650 cm-1 (medium). The frequency of these absorptions seems to be depending on the water or hydroxide content of the test sample. Rosin monovalent salts (e.g. Na, K) are hygroscopic; divalent salts (e.g. Ca, Mg, Zn) are not hygroscopic, but may contain hydroxide. - The complex region below 1500 cm-1 is the so-called fingerprint area. In general it is difficult to assign absorption to specific vibrations. Comparison of the spectrum of the test sample with reference spectra can give information on the substance identity. IR characteristics of different rosin derivatives are given in Table 2 Reference spectra (See Appendix 1) It is noted that the commonly available published spectra were prepared over 20 years ago. It is unclear as to the quality of the samples used, as well as the calibration of the spectrometer. For this reason H4R organised a new reference set in 2011. Conclusion: Infrared spectra can give indications on the nature of the substance. However, it is only possible to identify a substance by comparing carefully the spectra of rosin and rosin derivatives with reference spectra. December 2012 Page 5 of 106 Reference Document on the Identification of Rosin and Rosin derivatives
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