Collected Applications Thermal Analysis EVOLVED GAS ANALYSIS

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1 Collected Applications Thermal Analysis EVOLVED GAS ANALYSIS

2 Preface Over the past decades, the development and characterization of materials has become increasingly specialized due to the ever-increasing demands placed on quality. In addition, the widespread use of products such as blends, composites, new stabilizers and additives has resulted in relatively complex chemical systems. The great interest in material sciences has created a need for specific analytical tools to characterize the constituent inorganic and organic molecules. One particularly important development has been to combine well-established separation and identification techniques into one instrument system. This drastically increases the amount of specific information that can be obtained and shortens analysis times. This booklet provides an insight into two such so-called hyphenated techniques, TGA-FTIR and TGA- MS. The first part of the booklet focuses on basic principles and describes the techniques. It also includes a practical section and an introduction to the interpretation of spectra. The second part discusses some 15 different applications performed in our applications laboratory using TGA-MS and/or TGA-FTIR. Two additional applications illustrate the use of the rather unusual combination of TMA with MS. I would like to thank the Materials Characterization Section of the Market Support Group in Schwerzenbach, Switzerland for their helpful discussions, Mrs. Helga Judex for preparing the layout and Dudley May for checking the text. Schwerzenbach, October 2001 Cyril Darribère This application booklet presents selected application examples. The experiments were conducted with the utmost care using the instruments specified in the description of each application. The results were evaluated according to the current state of our knowledge. This does not however absolve you from personally testing the suitability of the examples for your own methods, instruments and purposes. Since the transfer and use of an application is beyond our control, we cannot of course accept any responsibility. When chemicals, solvents and gases are used, general safety rules and the instructions given by the manufacturer or supplier must be observed. TM All names of commercial products can be registered trademarks, even if they are not denoted as such. METTLER-TOLEDO Collected Applications EVOLVED GAS ANALYSIS Page 1

3 Contents Preface...1 Content...2 Abbreviations and Acronyms...3 Introduction to TGA-EGA...4 TGA-MS...5 TGA-FTIR...11 Introduction to the Applications...20 Applications List Decomposition of Acetylsalicylic Acid Thermal Degradation of BHET Influence of the Heating Rate on MS Response Decomposition of Technical Lauryl Alcohol Detection of Residual Solvents in a Pharmaceutical Substance Decomposition of Calcium Oxalate Monohydrate (Tutorial) Influence of Sample Weight on MS Sensitivity Decomposition of Copper Sulfate Pentahydrate (Tutorial) Desorption of a Zeolite Filled with Organic Matter Pyrolysis of PVC Powder Investigation of Fluorinated Cable Wires Detection of Methyl Salicylate in a Sample of Rubber Degradation of a Silicone Polymer Curing and Decomposition of an Amino Resin Identification of BR and NR Rubbers. Study of Thermal Transitions and Decomposition Delamination of Printed Circuit Boards Expansion and Decomposition of the Polymer Used to Encapsulate a Blowing Agent...63 Index...66 Notes...68 Page 2 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

4 2 Thermal Degradation of BHET Purpose Sample The aim of the experiment was to demonstrate how the evolved gas profile and evolved group profile techniques can be used to identify degradation products. BHET (bis-hydroxylethyl terephthalate). A common industrial synthetic route involves the esterification of terephthalic acid (TPA) with ethylene glycol (EG). BHET is usually polymerized to polyethylene terephthalate (PET). HO O O OH OH O + 2 HO O HO TPA EG BHET O O OH + 2 H2 O Conditions Measuring cells: Pan: TGA/SDTA851 e coupled to a Nicolet Nexus FTIR Alumina 70 µl, no lid Sample preparation: As received, no preparation mg TGA measurement: Heating from 50 C to 900 C at 10 K/min, blank curve corrected Atmosphere: Nitrogen, 80 ml/min % 50 0 %min^ TGA curve DTG curve Degradation of BHET (A) :47:28 Step % mg Step % mg Gram-Schmidt curve C Interpretation The two-step degradation of BHET results in maxima in the DTG curve at about 300 C and 450 C. Theses peaks correspond to the maxima in the Gram- Schmidt curve. Page 24 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

5 Evolved gas profile Interpretation The evolved gas profile method (see chapter on interpretation procedures of TGA-FTIR measurements) was used to identify the cause of the first weight loss step (DTG maximum at 300 C). Direct comparison of the FTIR spectrum at 300 C with database spectra characterizes the first component evolved as pure ethylene glycol. The doublet between 2340 and 2360 cm -1 (A) is due to residual carbon dioxide in system. Absorption bands in the range cm -1 and cm -1 (B) are attributed to water (background moisture). Functional group profile %min^-1 Degradation of BHET (B) :47:37 DTG curve cm-1 Alkane cm-1 Alcohol cm-1 Carboxylic acid cm-1 Ester C METTLER-TOLEDO Collected Applications EVOLVED GAS ANALYSIS Page 25

6 Interpretation Direct comparison of the spectrum at 450 C with the database did not identify any one particular decomposition product. The functional group profiles of possible decomposition products are displayed above. As expected, the maxima correspond to the maxima of the DTG curve. The identification of the degradation products is based on the measurement of the absorption bands corresponding to different chemical groups, for example the characteristic absorption bands of C-O for alcohols, carboxylic acids and esters. The profiles for aromatic ring and ketones were measured but no significant signals were detected. In fact the side chains of BHET are cleaved at temperatures above 400 C with the formation of hydroxy formic acid ester (CH-CO-O-(CH 2 ) 2 -OH). Evaluation Step, % Peak temperature DTG, C Possible products ethylene glycol hydroxy formic acid ester Conclusion The two closely lying weight loss steps cannot be interpreted with TGA alone. The use of a TGA-FTIR combination allows a qualitative characterization of the decomposition process. Based on an analysis of the spectrum at 300 C, we concluded that the first decomposition step is due to the loss of ethylene glycol. The second step was assumed to be due to the cleavage of the side chains of the aromatic group, i.e. the elimination of hydroxy formic acid ester. This study illustrates the application of the evolved gas profile and the functional group profile methods described in the introduction. The two techniques provide complementary information. Page 26 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

7 3 Influence of the Heating Rate on MS Response Purpose Sample Conditions The aim of the experiment was to investigate the influence of different heating rates on the response of the mass spectrometer. Malonic acid (COOH-CH 2 -COOH). Measuring cells: TGA/SDTA851 e coupled to a Balzers Thermostar mass spectrometer Pan: Aluminum 40 µl, no lid Sample preparation: The crystals were ground in a mortar. Sample weights of approx. 10 mg were used. TGA measurement: Heating from 50 C to 640 C at 5, 10, 20, 30, 40 and 50 K/min, blank curve corrected Atmosphere: Nitrogen, 50 ml/min ^exo Influence Heating Rate on MS (A) :49:49 % 50 TGA curves 5 K/min 10 K/min 20 K/min 30 K/min 40 K/min 50 K/min 0 C SDTA curves C Interpretation Samples of malonic acid were measured with TGA at heating rates between 5 and 50 K/min and the corresponding TGA signals recorded. The thermal decomposition of malonic acid exhibits a single weight loss step that shifts toward higher temperatures with increasing heating rates. The SDTA curves indicate that the sample begins to melt at approximately 134 C (onset temperature), and that this is independent of the heating rate. The decomposition process in the liquid phase depends on the heating rate; higher heating rates shift the onset of decomposition and the decomposition range to higher temperatures. METTLER-TOLEDO Collected Applications EVOLVED GAS ANALYSIS Page 27

8 m/z 60 Influence Heating Rate on MS (B) :49:59 Heating rate Integral Integral Integral nsa nsa nsa Integral Integral Integral nsa 50 na nsa nsa min Interpretation The decomposition of malonic acid results in the elimination of acetic acid, which was confirmed by the m/z 60 ion curve (see MS spectrum of acetic acid in Application 1). The m/z 60 ion curve was measured at each different TGA heating rate and the corresponding peak areas calculated. The results are summarized in the above diagram. The TGA curve showed that the weight losses were the same for each sample, i.e. the amount of acetic acid evolved was independent of the heating rate. Constant peaks areas for the m/z 60 curves were therefore also expected. In fact the calculated peak area shows a slight increase at higher heating rates. Evaluation Heating rate, K/min Onset / peak temperatures SDTA, C Melting Decomposition MS peak area (m/z 60), nsa Page 28 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

9 3000 Peak area m/z 60 [nsa] Heating rate [K/min] Conclusion The weight loss step due to the decomposition of malonic acid to acetic acid is independent of the heating rate. The m/z 60 peak area depends to a slight extent on the heating rate, although similar quantities of material are transported to the mass spectrometer. This effect might be due to the fact that because the heating rates are different, the concentration of acetic acid in the evolved gases is in each case very different. METTLER-TOLEDO Collected Applications EVOLVED GAS ANALYSIS Page 29

10 4 Decomposition of Technical Lauryl Alcohol Purpose Sample Conditions The aim of the experiment was to investigate the possible decomposition products of lauryl alcohol. Technical 1-dodecanol; CH 3 (CH 2 ) 11 OH, lauryl alcohol. Measuring cells: Pan: TGA/SDTA851 e coupled to a Nicolet Nexus FTIR Aluminum 40 µl, pierced lid (diameter: 50 µm) Sample preparation: The waxy material was melted in a water bath at 50 C. The homogeneous liquid was then filled directly into the crucible and cooled to room temperature before measurement TGA measurement: Heating from 30 C to 600 C at 5 K/min, blank curve corrected Atmosphere: Nitrogen, 50 ml/min % 50 0 % C^-1-1 TGA curve DTG curve Decomposition of Lauryl Alcohol :47:14 Step % mg Step % mg Step % mg -2 Gram-Schmidt curve C Interpretation The measurements were performed in crucibles sealed with pierced lids to improve the separation of the two weight loss steps in the TGA curve compared with measurements in an open crucible. The Gram-Schmidt curve shows two peaks that correspond to the weight loss steps at 207 C and 395 C (maxima of the DTG curve). Page 30 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

11 Interpretation The FTIR spectrum measured at about 207 C was very similar to that of 1-decanol in the spectrum database (e.g. stretching and bending vibrations of the alkane part at 2970, 2930, 2860, 1460 and 1380 cm -1 and the primary alcohol at 3670, 1350 and 1050 cm -1 ). A detailed comparison of the measured spectrum and the reference spectrum of dodecanol in the range cm -1 confirms that no dodecanol evaporates. A distinct shoulder can be observed on the high-temperature side of the peaks in both the DTG and GS curves of the first weight loss step. Spectra recorded in this shoulder however showed no new absorption bands. Possible explanations for this could be presence of other dodecanol isomers in the original sample, i.e. isomers with a higher boiling point, or polymerization. This would have to be checked with TGA-MS measurements. METTLER-TOLEDO Collected Applications EVOLVED GAS ANALYSIS Page 31

12 Interpretation Evaluation Some additional peaks were observed in the spectrum at 395 C. Besides the characteristic bands for alkanes and alcohols, the absorption bands at 3085 cm -1 (C-H stretching), 1640 cm -1 (C=C stretching) and 990/910 cm -1 (out-of-plane C-H bending) indicate the presence of a vinyl group. The second weight loss step could result from the decomposition of a polymerized compound. Step, % Peak temperature DTG, C Possible products decanol isomerization / polymerization product alkyl chain with a vinyl and alcohol group Conclusion The main functional groups such as alkane, alcohol and alkene were identified by FTIR measurements. The cleavage of the dodecanol chain results mainly in a shorter aliphatic alcohol (first step) and an alkene (third step). An isomerization or polymerization reaction is proposed to explain the degradation products of the second weight loss step. Page 32 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

13 5 Detection of Residual Solvents in a Pharmaceutical Substance Purpose Sample Conditions The aim of the experiment was to identify residues of solvents left in a pharmaceutical substance after recrystallization in a solvent mixture. Pharmaceutically active substance. Measuring cells: TGA/SDTA851 e coupled to a Balzers Thermostar mass spectrometer Pan: Alumina 70 µl, without lid Sample preparation: As received, no preparation mg TGA measurement: Heating from 30 C to 350 C at 10 K/min, blank curve corrected Atmosphere: Nitrogen, 20 ml/min % TGA curve Detection of Residual Solvents :48:21 Step % e-03 mg Step % e-03 mg lg(na) -2-3 MS curves m/z 31 m/z C Interpretation The TGA curve shows a number of weight loss steps in temperature range measured. The initial weight loss below 60 C is probably due to the gradual evaporation of adsorbed moisture or solvent(s) while the final step (above 250 C) no doubt arises from the decomposition of the product. The change in the intensities of the m/z 31 (methanol) and m/z 43 (acetone) fragment ions measured by TG-MS in the MID mode correspond to the weight loss steps in the range C and C respectively. The MS spectra of methanol and acetone are shown in the following diagrams. While methanol is evolved over a wide temperature range, the acetone (m/z 43) peak is appreciably sharper. The higher temperature indicates that acetone is more firmly bound in the substance in the form of a solvate. METTLER-TOLEDO Collected Applications EVOLVED GAS ANALYSIS Page 33

14 MS spectrum of methanol Rel. Abundance m/z MS spectrum of acetone Rel. Abundance m/z Evaluation Evaluation range, C Step, % Possible products methanol methanol, acetone Conclusion From the TG-MS results, it was possible to identify the solvents used to recrystallize the active ingredient. In this case (and in general), it is possible to distinguish between residual solvent that is merely adsorbed and solvent molecules that are more strongly bound in the form of solvates. Page 34 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

15 6 Decomposition of Calcium Oxalate Monohydrate (Tutorial) Purpose Sample Conditions Calcium oxalate monohydrate is used as a tutorial sample to demonstrate the decomposition reaction and stoichiometry. Calcium oxalate monohydrate decomposes in three reaction steps given by the following equations: (1) (2) (3) CaC 2 O 4.H 2 O CaC 2 O 4 CaCO 3 Calcium oxalate monohydrate (CaC 2 O 4.H 2 O). CaC 2 O 4 + H 2 O CaCO 3 + CO CaO + CO 2 Measuring cells: TGA/SDTA851 e coupled to a Balzers Thermostar mass spectrometer Pan: Alumina 70 µl, no lid Sample preparation: As received, no preparation mg TGA measurement: Heating from 70 C to 950 C at 30 K/min, blank curve corrected Atmosphere: Argon (50 ml/min) was used instead of nitrogen in order to be able to detect CO since CO and N 2 ions appear at the same m/z ratio % 100 TGA curve Decomposition of CaC2O4 (A) :46:48 Step % mg 80 Step % mg Step % mg Residue % mg C Interpretation The TGA curve shows three weight loss steps in agreement with the threestep reaction scheme given above. The loss of water of crystallization and the two decomposition steps yielded weight losses of 12.5%, 18.9% and 30.3% respectively. This is in good agreement with the theoretical stoichiometric values based on the fact that one mole of CaC 2 O 4 H 2 O gives rise to one mole each of H 2 O, CO and CO 2. METTLER-TOLEDO Collected Applications EVOLVED GAS ANALYSIS Page 35

16 ^exo Decomposition of CaC2O4 (B) :46:56 mgmin^-1 DTG curve -1-2 MS: H2O MS: CO MS: CO2 5 na C Interpretation From the above reaction scheme, one would expect H 2 O, CO and CO 2 to be evolved in turn at each step. The TG-MS ion curves showed this is in fact the case. However, in contrast to the reaction scheme, a small CO 2 peak was observed during the decomposition of the anhydrous oxalate in the second weight loss step. This is due to the disproportionation of CO to CO 2 (2CO CO 2 + C). Evaluation Stoichiometric step % Measured step % Peak temperatures DTG, C Possible products water of crystallization CO, CO CO 2 Conclusion According to the above reaction scheme, calcium oxalate monohydrate is expected to decompose in well-defined steps with the release of H 2 O, CO and CO 2. It seems that this process is more complicated as slight differences were observed between the measured and theoretical weight loss steps. The TG-MS results help clarify the matter by showing that CO 2 is also formed during the second reaction step. This was concluded as arising from the disproportionation reaction 2CO CO 2 + C. Page 36 EVOLVED GAS ANALYSIS METTLER-TOLEDO Collected Applications

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