Long-term performance of oils for stationary gas engines ... · AC²T research GmbH,...
Transcript of Long-term performance of oils for stationary gas engines ... · AC²T research GmbH,...
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AC²T research GmbH, Viktor-Kaplan-Straße 2, 2700 Wiener Neustadt, Austria
Tel. +43 (0) 2622 / 816 00-210, Fax +43 (0) 2622 / 816 00-99, e-mail: [email protected], web: www.ac2t.at
Long-term performance of oils for stationary gas engines
determined by lab-based artificial ageing as economic means
Need for novel artificial ageing methods… is based on general but significant requirements:
Knowledge about the impact of fuel in the oilEconomically short test durationPeriodical oil condition monitoring
… but not yet provided by standardized ageing procedures, e.g.,ASTM D 4871 – 06ASTM D 7079-09CEC L-48-A-00
A strong connection to the real-life conditions is required!
IntroductionGrowing interest in renewable energy due to:
Environmental concerns, e.g. global warmingAwareness of limited fossil fuel resources Reduction of dependence on oil imports and on increasing oil prices
Increasing use of bio-fuels from renewable materials
But trends towards high-power engines and the use of bio-fuels result in:Accelerated oil degradation and therefore shortened oil drain intervalsAcidification with unforeseen corrosion
Experimental set-upThe oil sample is kept at a selected temperature in a closed ageing reactor *). By circulation of the oil using a pump the oil is brought in contact with dried air. The air can be mixed with gaseous contaminations prior to supply to the ageing reactor. Over an outlet in the oil cycle continuous monitoring and/or automatic sampling is done.
Artificial ageing was carried out under following parameters:
Oil temperature: 160 °CAir flow: 10 L/hOil sampling: every 10 hTest duration with air: 120 hTest duration with air containing contamination: 60 hAmount of sample: 500 mL
Various oil parameters were monitored. The most important are:
Oxidation by FTIR in [Absorbance/cm]Total Base Number (TBN)Neutralization Number (NN)
Results and discussionArtificial ageing was carried out with a commonly available gas engine oil with and without contamination. The visual appearance (Fig. 1) of the oil after different artificial ageing periods clearly states the strong impact of contaminations on oil deterioration.
ConclusionsThe simulation of engine processes using the novel lab-based artificial ageing method has enabled …
good correlation between artificially aged engine oils and oils from the field according to conventional oil parameters,
differentiation in performance between different oil formulations,
understanding of ageing mechanisms by interactions with biogas, and
valuable input for the formulation of engine oils.
AcknowledgementThis work was funded by the "Austrian Kplus-Program" (governmental funding program for pre-competitive research) via the Austrian Research Promotion Agency
(FFG) and the Province of Niederösterreich (TecNet Capital GmbH) and has been carried out within the "Austrian Center of Competence for Tribology“.
[Faninger, G.: Renewable Energy Resources and Technologies in Austria – State of the art report 2005. Berichte aus Energie- und Umweltforschung 26/2006]
Fig. 2: Comparison of different artificial ageing conditions with field
conditions (a) Total Base Number and (b) Neutralization Number
The results were compared to oil samples from a gas engine in the field lubricated by the same oil.Fig. 2 shows the comparison of the most important oil parameters, namely total base number and neutralization number according to the respective oxidation values of artificially and naturally aged oils.
Fig. 1: Visual appearance of artificially aged oil samples
(a) with air and (b) with gaseous contamination
(a)
(b)
fresh 1d 2d 3d 4d
0
2
4
6
8
10
0 5 10 15 20
Oxidation [Abs/cm]
TB
N [
mg
KO
H/g
]
0
1
2
3
4
5
6
0 5 10 15 20
Oxidation [Abs/cm]
NN
[m
g K
OH
/g]
(a)
(b)
Ageing reactor
Pump Continuouscondition
monitoringand/or
automaticsampling
*) patentapplied
Ageing with air
Ageing with gas. contamination
Real engine filling 1
Real engine filling 2
Development of a novel lab-based artificial ageing method for …
rapid evaluation of the impact of biogas on the performance of selected gas engine oils, and
close-to-reality oil deterioration.
Charlotte Bessera*, Christoph Schneidhofera, Nicole Dörra, Franz Novotny-Farkasb, Günter Allmaierc
aAustrian Center of Competence for Tribology – AC²T research GmbH, Wiener Neustadt, AustriabOMV Refining & Marketing GmbH, Vienna, Austria
cInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Vienna, Austria*corresponding author: Charlotte Besser, e-mail: [email protected]
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AC²T research GmbH, Viktor-Kaplan-Straße 2, 2700 Wiener Neustadt, Austria
Tel. +43 (0) 2622 / 816 00-210, Fax +43 (0) 2622 / 816 00-99, e-mail: [email protected], web: www.ac2t.at
AcknowledgementThis work was funded by the “European Commission" within the FP7 programme Marie Curie “Initial Training Network MINILUBES (216011-2)” and has been
carried out within the "Austrian Center of Competence for Tribology“.
Degradation of ionic liquid based lubricantsstudied by mass spectrometry
a Austrian Center of Competence for Tribology – AC²T research GmbH, Wiener Neustadt, Austriab Institute of Chemical Technologies and Analytics, Vienna University of Technology, Vienna, Austria
*corresponding author: Lucia Pisarova, e-mail: [email protected]
Lucia Pisarovaa,b*, Christoph Gablera, Nicole Dörra, Ernst Pittenauerb, Günter Allmaierb
Introduction
Ionic liquids (IL) are object of research for their use in
lubricants. Compounds with both long-term performance and environmentally benign behaviour have to be made available to comply with the demand for sustainability.
For this reason, the chemical structure of a IL based on short chain ammonium bis(trifluoromethylsulfonyl)imide (NTF2) was modified step by step. Thermo-oxidative stability was investigated using high end mass spectrometry (MS) to elucidate the ageing behaviour on the molecular level.
Analysis of artificially aged IL
Visual appearance (colour and transparency)
Condition monitoring by Fourier Transformation Infrared Spectrometry with Attenuated Total Reflection (FTIR-ATR)
MS analysis by Laser Desorption Ionization - ReflectronTime-of-Flight (LDI-RTOF) MS and MS/MS (TOF/RTOF)
Conclusions
Low molecular IL were successfully examined by LDI-RTOF-MS and MS/MS (CID) for structural elucidation.
Methylated choline of IL3 was identified as degradation product under all artificial ageing conditions.
In contrast, choline moiety in IL2 remained stable under all artificial ageing conditions.
The importance to consider IL moieties together and not separately has been confirmed.
LDI-MS and MS/MS turned out as valuable technique to investigate lubricants applied for long-term lubrication.
LDI-RTOF mass spectrometric analysis
IL1 and IL2 which contain the NTF2 anion show no degradation
under all artificial ageing conditions.
Choline (m/z 104) degradation of IL3 under all examined conditions
by formation of (2-methoxy-ethyl)-trimethyl-ammonium (m/z 118).
Fig. 3: IL3 FTIR spectra, fresh, aged, 190°C
Fig. 6: Mass spectrum of artificially aged IL3, no metal immersed,190°C
Fig. 5: Mass spectrum of artificially aged IL2, no metal immersed,190°C
Reference
Zabet-Moghaddam, et al.: Matrix-assisted laser desorption/ ionization mass spectrometry
for the characterization of ionic liquids and the analysis of amino acids, peptides and
proteins in ionic liquids. J. Mass Spectrom. 2004, 24, 1494.
Results and Discussion
Experimental
Fig. 8: CID fragmentation tree of methylated choline
Fig. 7: Artificially aged IL3, MS/MS (CID) of precursor ion m/z 118
Visual appearance
Optical changes do not necessarily indicate structural changes of IL
Artificial ageing procedure
Parameters
�Temperature
�Air (O2)
�Water
�Metals immersed
IL1
IL2
IL3
collision induced dissociation (CID) for the identification of ions originating from the precursor ion m/z 118 (methylated choline)
proposed fragmentation for the structural confirmation of methylated choline (m/z 118) as precursor ion exhibiting structures of the resulting product ions
Ionic liquids selected
FTIR-ATR ionic liquid monitoring
comparison of FTIR spectra of fresh and aged IL
no valuable information on
structural changes gained
so far not directly applicable
for IL condition monitoring
Hydrophobic IL with good thermal-oxidative stability
Hydroxyl group to give biologically degradable structure, namely choline
NTF2 replaced by environmentally more benign methanesulfonate
Choline Methylatedcholine
Fig. 1: Small scale artificial ageing
sampling
sampling
7 days 14 days 21 days
150°C
175°C
190°C
Fig. 2: Optical appearance during artificial ageing at atmosphere
150°C 175°C 190°C
IL1Butyl-trimethyl-
ammonium NTF2
IL2Choline
NTF2
IL3Choline
methanesulfonate
IL
code
Sta
rt Access to air Name
Optical changes
�� �� �� �� ��� ��
�������
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� ����� ��������� Rela
tive a
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�� �� �� �� ��� ��
�������
����
��������
���
������� ���� ����
� ����� ��������� Rela
tive a
bundance
N+
CH3
CH3
CH3OCH
3
M+ (m/z 118)
N+
CH2CH2
CCH2
O
H+
+
CH3
O
+
N+
CH2
CH3
CH3
CH3
O CH2
CH2
+N
+
CH3
CH3
CH3
H
N+
CH3
CH3
CH3
CH3
N+
CH3
CH3
CH3
CH2
m/z 42
m/z 43
m/z 43
m/z 58
m/z 59m/z 60
m/z 74
m/z 86
m/z 102
N+
CH3
CH3
CH3
O
� N+
CH3
CH3
CH3OCH
3
M+ (m/z 118)
N+
CH2
CH2
CCH2
O
H+
+
CH3
O
+
N+
CH2
CH3
CH3
CH3
O CH2
CH2
+N
+
CH3
CH3
CH3
H
N+
CH3
CH3
CH3
CH3
N+
CH3
CH3
CH3
CH2
m/z 42
m/z 43
m/z 43
m/z 58
m/z 59m/z 60
m/z 74
m/z 86
m/z 102
N+
CH3
CH3
CH3
O
�
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Tel. +43 (0) 2622 / 816 00-10, Fax +43 (0) 2622 / 816 00-99, e-mail: [email protected], web: www.ac2t.at
ANALYSIS OF ANTIOXIDANTS APPLIED IN LUBRICANTS BY
ESI- AND AP-MALDI ION TRAP MSn (n = 1 - 3)
Alexander Kassler1,2, Ernst Pittenauer1, Nicole Doerr2 and Guenter Allmaier1
1Vienna University of Technology, Institute of Chemical Technologies and Analytics, Vienna, Austria2Austrian Center of Competence for Tribology (AC²T research GmbH), Wr. Neustadt, Austria
IntroductionAn important group of additives for lubricants are antioxidants applied for
stabilization and therefore improving oil change intervals considerably.
Important antioxidants constitute either sterically hindered phenolic compounds or
aromatic amines [1]. Investigation of both groups is necessary because phenols
and amines behave differently. Amines quench radical oxidation intermediates
very fast whereas slower reacting phenols regenerate the amines. Only in the
proper combination of these compounds an optimal stabilization of the lubricant
takes place. For first mass spectrometric experiments 22 different compounds
were selected for detailed mass spectrometric investigation.
ExperimentalAll analytes were measured by means of positive- and/or negative-ion ESI- and
AP-MALDI IT MS (Esquire 3000plus and HCTplus, respectively; Bruker Daltonics,
Bremen, Germany). For ESI measurements the samples were dissolved in
methanol: 2-propanol = 1: 1 (v/v). For the verification of molecular ions of aromatic
amines samples were also analyzed in methanol: water = 1: 1 (v/v) containing 0.1
% acetic acid. For AP-MALDI-MS -cyano-4-hydroxy cinnamic acid (CHCA) was
used as matrix. Samples were prepared either on gold-, TiN-, micro diamond-
covered targets or on SS targets (polished, sand-blasted). The elemental com-
position of certain selected ions was determined by accurate mass measurements
utilizing an ESI/AP-MALDI LTQ Orbitrap MS (Thermo, Bremen, Germany).
AcknowledgmentsThis work was funded by the "Austrian Kplus-Program" (governmental funding program for pre-
competitive research) via the Austrian Research Promotion Agency (FFG), the TecNet Capital
GmbH (Province of Lower Austria) and has been carried out within the AC²T research GmbH.
The AP-MALDI IT MS was provided by the Vienna University of Technology to G. Allmaier.
Research Research groupgroup biobio--
and polymer and polymer analysisanalysis
References1. Migdal, C. A, in Lubricant Additives: Chemistry and Application (Rudnick, L. R., Ed., CRC
Press, Boca Raton, Florida) 1-28 (2003).
Results and Discussion
OH
O
O
16
(A) OH
N
(B)
ESI-Ion Trap
All 22 selected antioxidants showed good results in positive-, whereas only some
of them could be detected in negative-ion mode.
In a water-free solution some aromatic amines like N,N‘-di-sec-butyl-p-
phenylenediamine (Fig. 1) primarily formed a M+• radical ion and relatively low
abundant [M+H]+- and [M+Na]+-ions (Fig. 2A). Only by changing the solvent to
methanol: water = 1: 1 containing 0.1% acetic acid the radical molecular ion could
be suppressed by favouring the [M+H]+-ion (Fig. 2B).
Data interpretation was performed by exporting mass spectra and CID spectra
into MassFrontier 5.0 (HighChem, Bratislava, Slovac Republic) for creating
spectral trees from MS1- up to MS3-spectra, which were created manually by
using the features of the Spectral Library (Fig. 3). Interpretation of CID spectra
was done by using tools of Fragmentation Library. With these features
fragmentation trees for all measured precursor ions of the antioxidants were
developed and saved to enhance the Library for future use (Fig. 4).
AP-MALDI-Ion Trap
In positive-ion AP-MALDI MS all aromatic amines and the phenols with a second
functional group were successfully desorbed/ionized and often formed unusual
molecular ions as M+• and [M-H]+. Desorption/ionization of simple phenols as
butylated hydroxytoluene was not feasible under the applied conditions. None of
the analytes could be measured in negative-ion AP-MALDI MS mode.
In addition, the effects of different target surfaces on the intensity of the molecular
ions of octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate and 2,6-di-tert-
butyl-4-(dimethylamino-methyl) phenol (Fig. 5) were investigated. Three spots of
each analyte were prepared on gold-, titan nitride- (TiN), micro diamond-covered
targets and on two different SS ones (polished, sand blasted) (Fig. 6). On the
plane gold-, TiN- and polished SS surfaces sample preparations give distinct
small spots (1 µl gave ø 3-4 mm). Solutions deposited on rough micro diamond-
covered and sand-blasted SS surfaces show the tendency to spread across a
larger area (1 µl gave ø 5-8 mm) (Fig. 6D-F).
First of all, the results show very little effect related to the target material on the
peak ratio of the analyte molecular ions with the exception of micro diamond-
covered target (Fig. 7). Because of the large area of the analyte solution,
crystallization was uneven and also the concentration per area was rather low at
rough surfaces. So, these mass spectra exhibited relatively low intensity and
reproducibility. Standard deviations of the measurements were up to half of the
average intensity. Again, the micro diamond-surface yields differing results with
respect to intensity and types of different molecular ions formed (Fig. 7B). Finally,
comparison of the two analytes does not show any trend for a target material
being more suitable for measuring antioxidants then the others. Hence it will be
necessary to find the optimal target for each antioxidant.
ConclusionsBased on the chemical structures of the antioxidants investigated, practically
all compounds could be characterized by positive-ion ESI and AP-MALDI MS.
Only a few compounds could be analyzed by negative-ion ESI MS in the
selected solvent system and none by negative-ion AP-MALDI MS with the
matrix CHCA.
The chemical structures are the main reason for the formation of seldom
observed molecular ions as M+• radical cations and even [M-H]+-ions which
are stabilized through the aromatic ring (some MALDI matrices exhibit a
similar behaviour).
Utilizing different target materials are influencing the signal intensity in AP-
MALDI MS. Therefore varying results of selected antioxidants on different
target surfaces indicate that for individual analyte molecules appropriate target
surfaces have to be found.
Fig. 5 Chemical structures of octadecyl-3-(3,5-di-tert-
butyl-4-hydroxyphenyl) propionat [MWt. monoisotopic
530.470 calculated] (A), 2,6-di-tert-butyl-4-(dimethyl-
amino-methyl) phenole [MWt. monoisotopic 263.225
calculated] (B).
Fig. 2 Positive-ion ESI-ion trap mass spectra of the antioxidants N,N‘-di-sec-butyl-p-phenylenediamine in
methanol : 2-propanol = 1: 1 (v/v) (A) and in methanol : water = 1: 1 (v/v) containing 0.1% acetic acid (B).
Fig. 3 Spectral tree of thiodiethylene bis-(3-(3,5-di-t-butyl-4-hydroxyphenyl) propionate) in Spectral Library based
on positive-ion ESI-MSn (n = 1 - 3) of the [M+H]+-, [M+NH4]+-, [M+Na]+- and [M+K]+- precursor ions.
MS3
MS2
MS2
O
O
OH
SO
O
OH
m/z 642.395
O
O
OH
SO
O
OH
NH4+
m/z 660.429
H+
O
O
OH
S
m/z 365.214
O
O
OH
S
H+
m/z 309.152
H+
O
O
OH
m/z 249.149
O
O
OH
H+
m/z 193.086
H+
O
O
m/z 175.075
+NH4+
+H+, rHR
MS2
rHC MS3
MS3
MS3
Fig. 4 Fragmentation tree of the [M+Na]+- precursor ion of thiodiethylene bis-(3-(3,5-di-t-butyl-4-hydroxyphenyl)-
propionate) in Fragmentation Library based on positive-ion ESI-MSn (n=1-3). Shown m/z-values are based on
theoretical calculations.
Fig. 1 Chemical structures of N,N‘-di-sec-butyl-p-phenylenediamine [MWt. monoisotopic 220.194 calculated] (A)and thiodiethylene bis-(3-(3,5-di-t-butyl-4-hydroxyphenyl) propionate) [MWt. monoisotopic 642.395 calculated] (B).
OH
O
O
S
OH
O
O
NH
NH
(B)(A)
60 80 100 120 140 160 180 200 220 240 m/z
RE
LA
TIV
E A
BU
ND
AN
CE
(B) Positive-ion ESI, 0.1% acetic acid
(A) Positive-ion ESI, water-free
[M+H]+
221.1
M+•
220.1
M+•
220.1
[M+Na]+
243.1
[M+H]+
221.1
Fig. 6 Different targets used in positive-ion AP-MALDI-
ion trap MS: gold-covered target (A), titan nitride-
covered target (B), polished SS target (C), different
sand-blasted SS target with one half more (D) and the
other half less rough-textured (E) and micro diamond-
covered target (F).
(A)
(C)
(B)
(E)(D)
(F)
Fig. 7 Comparison of the influence of the target materials expressed by the intensity of the molecular ions observed
([M-H]+, M+• and [M+H]+) by positive ion AP-MALDI-IT MS. Diagrams are representing an average value of 3
individual measurements (3 preparations in parallel on the same day) of octadecyl-3-(3,5-di-t-butyl-4-
hydroxyphenyl) propionat (A) and 2,6-di-t-butyl-4-(dimethylamino-methyl) phenole (B). Additionally, elemental
composition of molecular ions were determined by an AP-MALDI LTQ Orbitrap MS [R = 30.000, FWHM] (C),respectively (D).
261 262 263 264 265 266m/z
0
10
20
30
40
50
60
70
80
90
100
Rela
tive A
bund
ance
[M+H]+
264.23273
[M-H]+
262.21732
Isotopic Peak
C1613CH30ON
265.23611
Isotopic Peak
C1613CH28ON
263.22067
(D)(B)
528 529 530 531 532 533m/z
0
10
20
30
40
50
60
70
80
90
100
Rela
tive A
bund
ance
M+•
530.46960[M-H]+
529.46191
Isotopic Peak
C3413CH62O3
531.47345
(C)(A)
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IONICRAIL
Systemische Schienenkopf-Konditionierung durch alternative Konditioniermittel, wie Ionische Flüssigkeiten,
und Aufbringungsapparaturen
KonsortiumPartner 1: AC²T research GmbH (Projektleitung)
Kontakt: [email protected] 2: Wiener Linien GmbH & Co KG
Kontakt: [email protected] 3: HY-POWER Produktions- und Handels-GmbH
Kontakt: [email protected] 4: Büro für angewandte Mechanik und
Mathematik - Dr. Mittermayr Scientific Consulting GmbH (BAMM)Kontakt: [email protected]
Partner 5: psiA-Consult Umweltforschung und Engineering GmbH
Kontakt: [email protected] 6: Technische Universität Wien
Institut für Angewandte SynthesechemieKontakt: [email protected] 7: Technische Universität Wien
Institut für Verkehrswissenschaften, Forschungsbereich für Eisenbahnwesen, Verkehrswirtschaft und Seilbahnen
Kontakt: [email protected]
03.2009 - 02.2011 Projektart: IF
Ziel / InhalteEinstellung der Traktion zwischen Rad und Schiene
Ganzheitliche Erfassung des Tribosystems Rad-Schienenkopf-Konditioniermittel
Formulierung und Evaluierung alternativer Konditioniermittelauf Basis ionischer Flüssigkeiten
Optimierte Gestaltung einer automatischen ortsfestenKonditioniermittel-Aufbringung
Ionische Flüssigkeiten sind organische Salze mit
niedrigem Schmelzpunkt
(Zwischen)ErgebnisseKandidaten aus ionischen Flüssigkeiten
für die Erprobung in Feldversuchen erarbeitet
Theoretische (mathematische Simulation der mechanischenund thermischen Gegebenheiten) und
experimentelle (tribologischer Modellkontakt) Abbildung des Rad-Schiene-Kontakts
MilestonesAnforderungsprofil (Simulation, Erfahrung) an alternativer
Konditioniermittel erstellt
Definition, Formulierung und Untersuchungen alternativer Konditioniermittel im Labormaßstab abgeschlossen
Abstimmung zwischen Konditioniermittel und Aufbringungsapparatur erfolgt
Alternative Konditioniermittel und Aufbringungsapparaturin Feldversuchen evaluiert
KooperationenfractINSPECT, sysBahnLärm, UI2P InfraIntegrity,
UV wave, WDS Rille
Lessons LearnedStrukturanpassung ionischer Flüssigkeiten an die
Anforderungen eines alternativen Konditionierungsmittelsbzgl. biologischer Aktivität, Korrosivität, tribologischer
Eigenschaften
Erarbeitung geeigneter tribometrischer Messmethoden
Optimierungsansätze zur Konditioniermittel-Aufbringung
AusblickAusbau des interdisziplinären und intersektoralen Konsortiums auf
nationaler und internationaler EbeneÜbertragung der Erkenntnisse auf die Vollbahn
Verfeinerung der Formulierung und Kommerzialisierung alternativer Konditioniermittel
Geschlossen Geschlossen Offen
Pur Wasser gesättigt Pur
Start
150°C
175°C
Optische Veränderungen und Korrosionsverhalten einer ionischen Flüssigkeit gegenüber Schienen-Probekörper
Innere (von Mises) Spannungen in einem Rad-Schiene-Kontakt
N+
N
P
F
F
F
F
F
F
0
200
400
600
800
1000
1200
1400
1600
Fe
[p
pm
]
150 175 190
Temperatur [°C]