WO2019087156A1 - Composés, préparation de composés et application de ceux-ci - Google Patents

Composés, préparation de composés et application de ceux-ci Download PDF

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Publication number
WO2019087156A1
WO2019087156A1 PCT/IB2018/058661 IB2018058661W WO2019087156A1 WO 2019087156 A1 WO2019087156 A1 WO 2019087156A1 IB 2018058661 W IB2018058661 W IB 2018058661W WO 2019087156 A1 WO2019087156 A1 WO 2019087156A1
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WIPO (PCT)
Prior art keywords
coal
compound
formula
formaldehyde resin
formaldehyde
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Ceased
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PCT/IB2018/058661
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English (en)
Inventor
Debjani Nag
Pratik Swarup Dash
Soumitra GHORAI
Jyotirmayee Dash
Shilpi KARMAKAR
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Indian Association For Cultivation Of Science (iacs)
Tata Steel Ltd
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Indian Association For Cultivation Of Science (iacs)
Tata Steel Ltd
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Publication of WO2019087156A1 publication Critical patent/WO2019087156A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/16—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with amino- or nitrophenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
    • C10B57/00—Other carbonising or coking processes; Features of destructive distillation processes in general
    • C10B57/04—Other carbonising or coking processes; Features of destructive distillation processes in general using charges of special composition
    • C10B57/06—Other carbonising or coking processes; Features of destructive distillation processes in general using charges of special composition containing additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
    • C10B57/00—Other carbonising or coking processes; Features of destructive distillation processes in general
    • C10B57/08—Non-mechanical pretreatment of the charge, e.g. desulfurization

Definitions

  • the present disclosure is in the field of metallurgy in general.
  • the disclosure relates to compound of Formula I.
  • the disclosure further relates to a process for preparing the compounds of Formula I.
  • the disclosure furthermore relates to a method of improving coking potential of weak coal using the compounds of Formula I.
  • the disclosure also relates to a coal with improved coking potential.
  • Coke serves very important purposes in a blast furnace process; it is a fuel, reducing agent and is responsible for the permeability of the charge. Because of the numerous functions of coke in blast furnace, stringent quality parameters of its physical and chemical properties are required to ensure smooth operation of high productivity in modern blast furnaces. As the price of prime coking coal is high and the worldwide reserve of prime coking coal is low, there is a need to develop some alternate carbonaceous material, which can improve the coke quality.
  • additives can be organic or inorganic in nature and have been used in both solid and liquid form as binders in coal briquettes or as direct additions to the coal blend.
  • the additives are categorized in three main categories: organic, inorganic and bio by origin.
  • blends of coals of different origin and quality is the normal practice in the coke making industry.
  • other types of carbonaceous materials are also included in the formulation of industrial blends for coke production.
  • additives can be introduced in the coke oven e.g. non-coking coals such as anthracite and bituminous materials like coal-tar or coal-tar pitch.
  • materials from petroleum processing have also been used as additives in coke production.
  • Addition of binders like coal tar pitch to the coal blend, prior to stamping is expected to reduce the consumption of thermal energy and would impart the requisite strength and stability at lower moisture levels.
  • the pitch addition improves the strength characteristics of the resultant coke made from coals having poor rheological properties.
  • Formed coke is, in fact, a reconstituted fuel based on briquetting of coal, char or lignite, whereby the particulate matter is compacted with a suitable binder under pressure.
  • the raw or 'green' briquettes so obtained are subjected to oxythermal treatment (curing) and then carbonised with the purpose of reducing the volatiles.
  • the commonly used base materials for production of briquetted coke/formed coke include coal/lignites of different properties, char from low temperature carbonization of coal, coke breeze, or even mixtures of these, and the most common bituminous binders used for making formed coke for industrial purposes are residual products from processing coal tar and petroleum.
  • Another organic binder used in coke making is different form of plastics.
  • the additives of the prior art include addition of 2 wt. % plastic waste which causes a decrease in the maximum fluidity of the coal developed during thermal heating between 400°C and 500°C. The extent of the reduction being influenced by the initial value of coal fluidity, the thermal behaviour of the plastic waste itself, the composition of the pyrolysis products and, consequently, the hydrogen donor and acceptor abilities of the polymer.
  • polystyrene, polyethylene terephthalate which are characterized by the presence of aromatic rings in the polymer chain and a loss of volatile matter in the coal pre-plastic stage and in the earlier stages of fluidity development.
  • polystyrene and polyethylene terephthalate that have an aromatic group in their structure inhibits the fluidity development of a low-fluid coal, while the high-fluid coal still retains a certain degree of fluidity, except for the blend with poly ethylene terephalate (PET).
  • the present disclosure relates to a compound of Formula I
  • 'Ar' is selected from a group comprising phenyl, quinolinyl and naphthyl amino; 'Ri' is methyl or amino; and
  • 'n' ranges from 10 to 25.
  • the present disclosure further provides a process for preparing compound of Formula I, comprising act of:
  • the present disclosure further relates to a method of improving coking potential of coal, comprising acts of:
  • the Crucible Swelling Number (CSN) of the coal ranges from 1 to 4.5.
  • the compound is used at a concentration ranging from 0.5 to 3 %.
  • the present disclosure further relates to a coal comprising the compound of Formula I.
  • the coal comprising the compound of Formula I has a Crucible Swelling Number (CSN) ranging from about 1.5 to 6.5.
  • Figure 1 (a-d) depicts FTIR graph of m-cresol-formaldehyde resin (CF), 8-hydroxyquinoline- formaldehyde resin (HQF), 5-amino-l-Naphthol-formaldehyde resin (ANF), and 4- aminophenol-formaldehyde resin (APF).
  • CF m-cresol-formaldehyde resin
  • HQF 8-hydroxyquinoline- formaldehyde resin
  • NAF 5-amino-l-Naphthol-formaldehyde resin
  • API 4- aminophenol-formaldehyde resin
  • Figure 2 depicts TGA graphs of m-cresol-formaldehyde resin (CF), 8-hydroxyquinoline- formaldehyde resin (HQF), 5-amino-l-Naphthol-formaldehyde resin (ANF), and 4- aminophenol-formaldehyde resin (APF).
  • CF m-cresol-formaldehyde resin
  • HQF 8-hydroxyquinoline- formaldehyde resin
  • NAF 5-amino-l-Naphthol-formaldehyde resin
  • API 4- aminophenol-formaldehyde resin
  • Figure 3 depicts standard button for CSN.
  • Figure 4 depicts normalized hydrogen intensity for Coal A, m-cresol-formaldehyde resin (CF), 8-hydroxyquinoline-formaldehyde resin (HQF), 5-amino-l-Naphthol-formaldehyde resin (ANF), and 4- aminophenol-formaldehyde resin (APF).
  • Figure 5 depicts normalized hydrogen intensity for Coal Aand m-cresol-formaldehyde resin (CF).
  • Figure 6 depicts normalized hydrogen intensity for Coal A and 8-hydroxyquinoline- formaldehyde resin (HQF).
  • Figure 7 depicts normalized hydrogen intensity for Coal A and 5-amino-l-Naphthol- formaldehyde resin (ANF).
  • Figure 8 depicts normalized hydrogen intensity for Coal A and 4- aminophenol-formaldehyde resin (APF).
  • the term/phrase 'coal' refers to weak coal or inferior coal.
  • the present disclosure relates to a compound of Formula I
  • 'Ar' is selected from a group comprising phenyl, quinolinyl and naphthyl amino;
  • 'Ri ' is methyl or amino
  • 'n' ranges from 10 to 25.
  • the compound of Formula I is selected from a group comprising m-cresol-formaldehyde resin (CF), 8-hydroxyquinoline-formaldehyde resin (HQF), 5-amino-l-Naphthol-formaldehyde resin (ANF), and 4- aminophenol-formaldehyde resin (APF).
  • CF m-cresol-formaldehyde resin
  • HQF 8-hydroxyquinoline-formaldehyde resin
  • NAF 5-amino-l-Naphthol-formaldehyde resin
  • API 4- aminophenol-formaldehyde resin
  • the compound of Formula I is thermally stable.
  • thermal stability of the resins ranges from 300°C to 400°C.
  • the compound of Formula I upon Fourier transform infrared (FTIR) spectroscopy illustrates presence of phenolic-OH stretches at about 3400cm “1 to 3200cm “1 , peak for aliphatic -CH is present at about 2062 cm “1 and 2870 cm “1 .
  • the peaks at about 900cm " 1 and about 690 cm “1 illustrates the presence of aromatic -CH bending.
  • the aliphatic-CH bends is present at about 1439cm "1 and about 1399cm “1 . Peaks at about 1630 cm “1 to 1400 cm “1 indicates presence of aromatic C-C stretches.
  • the compound of Formula I releases hydrogen upon contacting with coal at a temperature ranging from about 400°C to 600°C. In another embodiment, the compound of Formula I releases hydrogen upon contacting with coal at a temperature of about 400°C, about 450°C, about 500°C, about 550°C or about 600°C.
  • the compound of Formula I improves the coking potential of inferior coal. In an embodiment, the compound of Formula I acts as fluidity enhancer.
  • the compound of Formula I acts as hydrogen donor and help to stabilise metaplast during co-pyrolysis with coal.
  • the present disclosure also relates to a process for preparing compound of Formula I, wherein the process is a single step process.
  • the process of preparing the compound of Formula I comprises step of reacting phenol derivative with formaldehyde in presence of a base.
  • the process of preparing the compound of Formula I comprises step of reacting excess formaldehyde with phenol derivative in presence of base catalyst in water solution to yield compound of Formula I, which is a low-molecular weight prepolymer with CH2OH groups attached to the phenol rings.
  • the compound upon heating condenses with loss of water and formaldehyde to yield thermosetting networks of compound of Formula I.
  • the phenol derivative is selected from a group comprising m-cresol, 8-hydroxy quinoline, 5-amino-l-Naphthol, and 4-aminophenol.
  • the base or the base catalyst employed in the process of the preparing compound of Formula I is sodium hydroxide (NaOH).
  • the phenol derivative and the formaldehyde is at a ratio of about 1 :2.
  • the NaOH is at a concentration ranging from about 8% to 12%.
  • the NaOH is at a concentration of about 8%, about 9%, about 10%, about 11% or about 12%.
  • the compound of Formula I is condensed by heating to a temperature ranging from about 70°C to 90°C.
  • the compound of Formula I is condensed by heating to a temperature of about 70°C, about 80°C or about 90°C.
  • the carbon density is increased with the increment of aromatic ring and due to positive inductive (+ I) effect of alkyl group the ortho position of the phenol derivative is more reactive.
  • the present disclosure further relates to a method of improving coking potential of coal by employing the compound of Formula I of the present invention.
  • the method of improving the coking potential of coal comprises steps of: contacting the compound of Formula I defined above with the coal; and
  • the heating of the compound of Formula I and the coal is carried out at a temperature ranging from about 400°C to 600°C.
  • the compound of Formula I donates its sacrificial active hydrocarbon sites which helps in pairing up with coal molecules, which in turn helps in efficient aromatization of coal followed by condensation of large polyaromatic hydrocarbon within the coal, thus improving the coking potential of the coal.
  • the hydrogen evolution is in sufficient amount which acts as a feed for the cracked molecules in the coal.
  • the hydrogen evolution during the process is a measure of aromatization process and it reaches its maximum at the maximum fluidity temperature ranging from about 300°C to 700°C.
  • evolution of hydrogen gas at the temperature ranging from about 300°C to 700°C showed a correlation for coke making.
  • contacting the compound of Formula I with coal and heating to a temperature ranging from about 400°C to 600°C improves hydrogen evolution and swelling of coal .
  • the obtained coal with improved coking potential exhibits good thermoplastic behavior.
  • Cib Swelling Number (CSN) of the coal ranges from 1 to 4.5.
  • the compound is used at a concentration ranging from 0.5 to 3 %.
  • CSN of coal after addition of compound ranges from 1.5 to 6.5.
  • the present disclosure further relates to a coal comprising the compound of Formula I.
  • coal comprising the compound of Formula I has improved coking potential.
  • the coal comprising the compound of Formula I has enhanced Crucible Swelling Number (CSN).
  • the coal comprising the compound of Formula I has a Crucible Swelling Number (CSN) ranging from about 1.5 to 6.5.
  • CSN Crucible Swelling Number
  • cresol alkyl substitute phenol (C6H5ROH)
  • C6H5ROH alkyl substitute phenol
  • the synthesized compound of Formula I is characterized by Fourier transform infrared (FTIR) analysis.
  • FTIR Fourier transform infrared
  • the infrared spectrum provides important information on molecular structure, especially the functionalities of organic compounds.
  • FTIR spectra of coal samples are run on KBr pellets (120 mg, 1 wt. %). Spectra are recorded by co-adding 124 scans at a resolution of 2 cm "1 in a Nicolet 550 spectrometer using a DTGS detector. Software facilities are used for baseline corrections of spectra which are scaled to 1 mg sample cm "2 . For quantitative measurements of spectra duplicate pellets are used.
  • FTIR spectroscopy is applied to confirm the functional group of the synthesized compound of Formula I quantitatively.
  • Figure 1 (a-d) shows the FTIR spectra of compound of Formula I.
  • Phenolic -OH stretches in the compound is present at about 3400 cm “1 to 3200 cm “1 .
  • Peak for aliphatic -CH is present at about 2062 cm “1 and about 2870 cm “1 .
  • Peaks at about 900 cm “1 and about 690 cm “1 indicates the aromatic -CH bending.
  • Aliphatic -CH bends are present at about 1439 cm “1 and about 1399 cm “1 .
  • Peaks at about 1630 cm “1 to 1400 cm “1 indicates presence of aromatic C-C stretches.
  • the aliphatic (Hai) and aromatic (Har) hydrogen contents are calculated from the integrated absorbance areas of the bands at about 3000 cm “1 to 2700 cm “1 and at about 900 cm “1 to 700 cm “1 , respectively.
  • the extinction coefficients used for converting integrated absorbance areas to concentration units are about 541 Abs cm “1 and about 710 Abs cm “1 mg cm “2 for the aromatic and aliphatic bands respectively of peat, lignite and subbituminous coal, and 684 and 744 Abs cm “1 mg cm “2 for bituminous coal and semi-anthracite. 5.2 TGA study
  • Thermogravimetric Analysis is used to investigate thermal events and kinetics during pyrolysis of solid raw materials such as coal, plastic etc. It provides a measurement of weight loss of the sample as a function of time and temperature. It is an excellent method for realizing the chemical changes that occurred during devolatilization of coal under progressive heating.
  • Thermogravimetric analysis of the individual coals is performed using a TGA apparatus. About 15 mg of the coal sample containing compound of Formula I is placed on a platinum cell. Then, the electric furnace is closed and purged with Ar with a flow rate of about 100 ml/min and at a pressure of about 0.5 bar.
  • the furnace is heated from ambient temperature of about 25°C to about 1100 ° C with a heating rate of about 3°C /min.
  • the relevant m/z values for instance, it is 2 for hydrogen
  • the software is fed to the software to trace out the path and intensity of the input compounds.
  • Figure 2 presents TGA graph of compounds of Formula 1. It shows that organic polymers have good thermal stability.
  • Figure 2 presents TGA graph of compounds of Formula 1. It shows that organic polymers have good thermal stability.
  • coal A and coal B which cannot pass through the plastic phase during pyrolysis and have poor hydrogen evolution during pyrolysis. Both are weaker coal having CSN 1 and 4, respectively. Initially, the properties of these two coals are evaluated. Then about 1 % of compound of Formula I is added to each of the coal, and then tested for coking potential like crucible swelling number. Upon addition of compound of Formula I the crucible swelling number (CSN) and hydrogen evolution of the coal are improved.
  • CSN crucible swelling number
  • the standard button for CSN is depicted in Figure 3. This test is performed using standard IS 1353: 1993. In which about 1 gm of coal sample (-0.212 mm size) is taken in a translucent squat shaped silica crucible and the sample is levelled by tapping the crucible for about 12 times. The crucible is covered with a lid and heated under standard conditions by a special type of gas burner. After the test, the shape of coke button is compared with a standard chart and accordingly, the crucible swelling number (1 to 9) is assigned to the coal sample. The initial CSN of coal A and B are 1 and 4.5 respectively.
  • Table 1 summarizes the CSN result of coal after the addition of compound of Formula I. In each case, about 0.5% to 3 % of the compound is added. From the results obtained, the preferred amount of polymer is found to be about 1%.
  • OP 1 refers to m-cresol-formaldehyde resin (CF)
  • OP2 refers to 8-hydroxyquinoline- formaldehyde resin (HQF)
  • OP3 refers to 5-amino-l-Naphthol-formaldehyde resin (ANF)
  • OP4 refers to 4- aminophenol-formaldehyde resin (APF). 5.5 Mass Spectroscopy study
  • Quadrupole mass spectrometer with heated capillary inlet system is used for the analysis of gases and gaseous decomposition products.
  • QMS-430-D Aelos gas analysis system is used for the qualitative determination of gaseous components, which are emitted during the thermogravimetric analysis.
  • a typical mass spectrometer gives the graph between ion current and temperature (°C). But as the ion currents vary from coal to coal in magnitudes, it is relatively difficult to compare some of the compounds on the above-mentioned basis. Therefore, a normalization technique is followed in order to have a fair comparison among all the coals and thereby trying to predict their coking behaviours.
  • the normalized ion intensities are calculated according to the following equation:
  • Ni 100 - 100( ' ⁇ ' 1 " 1 " )
  • Ni is the normalized ion intensity
  • Imax is the maximum ion current
  • Imin is the minimum ion current.
  • Normalized ion intensities are plotted against temperatures in order to compare the evolution profiles of various gases for various coals. Tracking of all the constituents is done by a quadruple mass analyzer under MID scan mode. There are 64 channels for specifying the molecular weights. In MID mode, the MS analyzer tracks the pre-specified compounds over the entire period of degradation temperature. This technique is very useful for doing comparative analysis of different types of metallurgical coals. 5.6 Hydrogen liberation and correlation with coking potential
  • Plastic zone is the most crucial zone in the coke making process. Good coking coals also exhibit good thermoplastic behaviour. Cracking and condensation reactions compete with each other and crosslinking of macromolecules take place. In this process H2 should evolve in sufficient amount to act as feed for the cracked molecules. Simultaneously H2 evolution is also a measure of aromatization process and it reaches its maximum at the maximum fluidity temperature. Thus, evolution of H2 gas in the zone of about 300°C to 700 °C shows a very good correlation for coke making perspective.
  • the normalized ion intensity curves basically represent the qualitative analysis of the evolution of H2 throughout the decomposition temperature range.
  • the thermoplastic zone which ranges from about 400°C to 600°C provides a better understanding of the coking potential, where the maximum evolution of volatile matter takes place and the peak of the DTG curve is obtained.
  • coal A wherein the cracking process is more which may not abstract H2 from the hydro aromatic compound, but addition of organic polymers donates it sacrificial active hydrocarbon sites which helps in pairing up with coal molecules for an efficient aromatization followed by condensation into a large polyaromatic hydrocarbon. In other words, it helps in efficient polymerization of coal during pyrolysis. It can be inferred that with the addition of organic polymers (OPl, OP2, OP3, OP4) hydrogen evolution at the range of 400°C to 600°C is improved.
  • organic polymers OPl, OP2, OP3, OP4
  • Figure 4-8 presents the normalized intensity of hydrogen with temperature for Coal without the addition of organic polymers (OP 1, OP2, OP3, OP4) and with the addition of organic polymers (OPl, OP2, OP3, OP4) individually. It is revealed from the figures that initially the hydrogen generation of non-coking coal in the plastic region is less. With addition of the different polymers the hydrogen generation in the plastic region get improved. Hence there is an indication of improvement of coking potential of a non-coking coal with the addition of organic compounds.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé de formule (I). L'invention concerne en outre un procédé de préparation du composé de formule (I). L'invention concerne en outre un procédé pour améliorer le potentiel de cokéfaction de charbon inférieur. Les composés de la présente invention améliorent le potentiel de cokéfaction du charbon lorsqu'il est comparé au charbon sans la présence de composés de la présente invention. L'invention concerne également un charbon ayant un potentiel de cokéfaction amélioré, ayant un CSN amélioré.
PCT/IB2018/058661 2017-11-06 2018-11-05 Composés, préparation de composés et application de ceux-ci Ceased WO2019087156A1 (fr)

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IN201731039496 2017-11-06

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6423467B1 (en) * 1998-04-06 2002-07-23 Fuji Photo Film Co., Ltd. Photosensitive resin composition

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6423467B1 (en) * 1998-04-06 2002-07-23 Fuji Photo Film Co., Ltd. Photosensitive resin composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
U. SWIETLIK ET AL.: "Modification of coking behaviour of coal blends by plasticizing additives", JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, vol. 52, no. 1, 1 September 1999 (1999-09-01), pages 15 - 31, XP055613916 *

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