Skip to main content
Erschienen in: Biomass Conversion and Biorefinery 2/2015

01.06.2015 | Original Article

Catalytic upgrading of crude tall oil into a paraffin-rich liquid

verfasst von: Jinto M. Anthonykutty, Juha Linnekoski, Ali Harlin, Antero Laitinen, Juha Lehtonen

Erschienen in: Biomass Conversion and Biorefinery | Ausgabe 2/2015

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Catalytic upgrading via hydrotreatment is an essential method to produce paraffin-range renewable feedstocks from bio-derived oils. This research approach studies the catalytic hydrotreating of crude tall oil (CTO) over a sulfided NiMo catalyst under industrial-relevant conditions in order to produce hydrocarbon fraction, a steam cracker feed with maximum amount of paraffins and high degree of deoxygenation. Initial activity of the catalyst (6 h of time on stream) has been investigated, and we report that hydrotreating experiments at most favorable tested conditions (weight hourly space velocity, WHSV = 1 h−1 and T = 350–400 °C) produces hydrocarbon fraction with 45 wt% of paraffins (n-alkanes + i-alkanes). The highest degree of deoxygenation (91 %) was achieved at WHSV = 1 h−1 and T = 350 °C. Furthermore, the potential of hydrotreated CTO for steam cracking applications has been assessed in this study in view of the achieved product distribution and degree of deoxygenation from the hydrotreating of CTO.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Rapra S (2012) The future of bio plastics, market forecasts to 2017, Market Research Report- 262984. Accessed 11 Nov 2013 Rapra S (2012) The future of bio plastics, market forecasts to 2017, Market Research Report- 262984. Accessed 11 Nov 2013
2.
Zurück zum Zitat Pyl SP, Schietekat CM, Reyniers MF, Abhari R, Marin GB, Van Geem KM (2011) Biomass to olefins: cracking of renewable naphtha. Chem Eng J 176–177:178–187CrossRef Pyl SP, Schietekat CM, Reyniers MF, Abhari R, Marin GB, Van Geem KM (2011) Biomass to olefins: cracking of renewable naphtha. Chem Eng J 176–177:178–187CrossRef
3.
Zurück zum Zitat Kubičková I, Kubička D (2010) Utilization of triglycerides and related feedstocks for production of clean hydrocarbon fuels and petrochemicals: a review. Waste Biomass Valorization 1(3):293–308CrossRef Kubičková I, Kubička D (2010) Utilization of triglycerides and related feedstocks for production of clean hydrocarbon fuels and petrochemicals: a review. Waste Biomass Valorization 1(3):293–308CrossRef
4.
Zurück zum Zitat Huber GW, O’Connor P, Corma A (2007) Processing biomass in conventional oil refineries: production of high quality diesel by hydrotreating vegetable oils in heavy vacuum oil mixtures. Appl Catal 329:120–129CrossRef Huber GW, O’Connor P, Corma A (2007) Processing biomass in conventional oil refineries: production of high quality diesel by hydrotreating vegetable oils in heavy vacuum oil mixtures. Appl Catal 329:120–129CrossRef
5.
Zurück zum Zitat Abhari R, Havlik PZ (2009) Hydrodeoxygenation process. US patent publication 2009/0163744 Abhari R, Havlik PZ (2009) Hydrodeoxygenation process. US patent publication 2009/0163744
6.
Zurück zum Zitat Abhari R, Tomlinson HL, Roth EG (2009) Biorenewable naphtha. US patent publication 2009/0300971 A1 Abhari R, Tomlinson HL, Roth EG (2009) Biorenewable naphtha. US patent publication 2009/0300971 A1
7.
Zurück zum Zitat Sunde K, Brekke A, Solberg B (2011) Environmental impacts and costs of hydrotreated vegetable oils, transesterified lipids and woody BTL—a review. Energies 4(6):845–877CrossRef Sunde K, Brekke A, Solberg B (2011) Environmental impacts and costs of hydrotreated vegetable oils, transesterified lipids and woody BTL—a review. Energies 4(6):845–877CrossRef
10.
Zurück zum Zitat Vermeiren W, Gyseghem VN (2012) Process for the production of bio-naphtha from complex mixtures of natural occurring fats and oils. US patent publication 2012/0142983 A1 Vermeiren W, Gyseghem VN (2012) Process for the production of bio-naphtha from complex mixtures of natural occurring fats and oils. US patent publication 2012/0142983 A1
11.
Zurück zum Zitat Coll R, Udas S, Jacoby WA (2001) Conversion of the rosin acid fraction of crude tall oil into fuels and chemicals. Energy Fuel 15:1166–1172CrossRef Coll R, Udas S, Jacoby WA (2001) Conversion of the rosin acid fraction of crude tall oil into fuels and chemicals. Energy Fuel 15:1166–1172CrossRef
12.
Zurück zum Zitat Sharma RK, Bakhshi NN (1991) Catalytic conversion of crude tall oil to fuels and chemicals over HZSM-5: effect of co-feeding steam. Fuel Process Technol 27:113–130CrossRef Sharma RK, Bakhshi NN (1991) Catalytic conversion of crude tall oil to fuels and chemicals over HZSM-5: effect of co-feeding steam. Fuel Process Technol 27:113–130CrossRef
13.
Zurück zum Zitat Chatterjee S, Omori S, Marda S, Shastri S (2010) Process for making biodiesel from crude tall oil. US patent publication 7695532 B2 Chatterjee S, Omori S, Marda S, Shastri S (2010) Process for making biodiesel from crude tall oil. US patent publication 7695532 B2
15.
Zurück zum Zitat Knuuttila P, Kukkonen P, Hotanen Ulf (2010) Method and apparatus for preparing fuel components from crude tall oil. Patent publication WO2010097519 A2 Knuuttila P, Kukkonen P, Hotanen Ulf (2010) Method and apparatus for preparing fuel components from crude tall oil. Patent publication WO2010097519 A2
16.
Zurück zum Zitat Stigsson L, Naydenov V (2009) Conversion of crude tall oil to renewable feedstock for diesel range fuel compositions. European patent publication WO 2009/131510 A1 Stigsson L, Naydenov V (2009) Conversion of crude tall oil to renewable feedstock for diesel range fuel compositions. European patent publication WO 2009/131510 A1
17.
Zurück zum Zitat Diaz MAF, Markovits RA, Markovits SA (2005) Process for refining a raw material comprising black liquor soap, crude tall oil or tall oil pitch. EP1568 760 A1 Diaz MAF, Markovits RA, Markovits SA (2005) Process for refining a raw material comprising black liquor soap, crude tall oil or tall oil pitch. EP1568 760 A1
18.
Zurück zum Zitat Myllyoja J, Aalto P, Savolainen P, Purola V, Alopaeus V, Grönqvist J (2012) Process for the manufacture of diesel range hydrocarbons. US 8212094 B2 Myllyoja J, Aalto P, Savolainen P, Purola V, Alopaeus V, Grönqvist J (2012) Process for the manufacture of diesel range hydrocarbons. US 8212094 B2
19.
Zurück zum Zitat Anthonykutty JM, Van Geem KM, Bruycker RD, Linnekoski J, Laitinen A, Räsänen J, Harlin A, Lehtonen J (2013) Value added hydrocarbons from distilled tall oil via hydrotreating over a commercial NiMo catalyst. Ind Eng Chem Res 52(30):10114–10125CrossRef Anthonykutty JM, Van Geem KM, Bruycker RD, Linnekoski J, Laitinen A, Räsänen J, Harlin A, Lehtonen J (2013) Value added hydrocarbons from distilled tall oil via hydrotreating over a commercial NiMo catalyst. Ind Eng Chem Res 52(30):10114–10125CrossRef
20.
Zurück zum Zitat Anthonykutty JM, Kaila R, Pyl SP, Van Geem KM, Linnekoski J, Laitinen A Rasanen J, Penttinen T, Harlin A, Krause O (2012) Catalytic upgrading of tall oil and its fractions into value hydrocarbons via hydrodeoxygenation. Paper presented at 20th European Biomass Conference and Exhibition, Milan, Italy. 10.5071/20thEUBCE2012-3CO.11.1 Pages, 1532 – 1535 Anthonykutty JM, Kaila R, Pyl SP, Van Geem KM, Linnekoski J, Laitinen A Rasanen J, Penttinen T, Harlin A, Krause O (2012) Catalytic upgrading of tall oil and its fractions into value hydrocarbons via hydrodeoxygenation. Paper presented at 20th European Biomass Conference and Exhibition, Milan, Italy. 10.​5071/​20thEUBCE2012-3CO.​11.​1 Pages, 1532 – 1535
21.
Zurück zum Zitat Pyl SP, Dijkmans T, Antonykutty JM, Reyniers MF, Harlin A, Van Geem KM, Marin GB (2012) Wood-derived olefins by steam cracking of hydrodeoxygenated tall oils. Bioresour Technol 126:48–55CrossRef Pyl SP, Dijkmans T, Antonykutty JM, Reyniers MF, Harlin A, Van Geem KM, Marin GB (2012) Wood-derived olefins by steam cracking of hydrodeoxygenated tall oils. Bioresour Technol 126:48–55CrossRef
22.
Zurück zum Zitat Kirshner M (2005) Chemical profile: tall oil. Chem Mark Report 34 Kirshner M (2005) Chemical profile: tall oil. Chem Mark Report 34
23.
Zurück zum Zitat De Guzman D (2006) Markets—oils, fats, & waxes. Chem Mark Report 21 De Guzman D (2006) Markets—oils, fats, & waxes. Chem Mark Report 21
24.
Zurück zum Zitat Beens J, Brinkman UA (2005) Comprehensive two-dimensional gas chromatography—a powerful and versatile technique. Analyst 130(2):123–127CrossRef Beens J, Brinkman UA (2005) Comprehensive two-dimensional gas chromatography—a powerful and versatile technique. Analyst 130(2):123–127CrossRef
25.
Zurück zum Zitat Warnqvist J (2013) Process for obtaining a diesel like fuel. EP 2602306A1 Warnqvist J (2013) Process for obtaining a diesel like fuel. EP 2602306A1
26.
Zurück zum Zitat Donnis B, Egeberg RG, Blom P, Knudsen KG (2009) Hydroprocessing of bio-oils and oxygenates to hydrocarbons. Understanding the reaction routes. Top Catal 52(3):229–240CrossRef Donnis B, Egeberg RG, Blom P, Knudsen KG (2009) Hydroprocessing of bio-oils and oxygenates to hydrocarbons. Understanding the reaction routes. Top Catal 52(3):229–240CrossRef
27.
Zurück zum Zitat Kubička D, Šimáček P, Žilková N (2009) Transformation of vegetable oils into hydrocarbons over mesoporous-alumina-supported CoMo catalysts. Top Catal 52(1–2):161–168CrossRef Kubička D, Šimáček P, Žilková N (2009) Transformation of vegetable oils into hydrocarbons over mesoporous-alumina-supported CoMo catalysts. Top Catal 52(1–2):161–168CrossRef
28.
Zurück zum Zitat Kikhtyanin OV, Rubanov AE, Ayupov AB, Echevsky GV (2010) Hydroconversion of sunflower oil on Pd/SAPO-31 catalyst. Fuel 89(10):3085–3092CrossRef Kikhtyanin OV, Rubanov AE, Ayupov AB, Echevsky GV (2010) Hydroconversion of sunflower oil on Pd/SAPO-31 catalyst. Fuel 89(10):3085–3092CrossRef
29.
Zurück zum Zitat Guzman A, Torres JE, Prada LP, Nunez ML (2010) Hydroprocessing of crude palm oil at pilot plant scale. Catal Today 156(1–2):38–43CrossRef Guzman A, Torres JE, Prada LP, Nunez ML (2010) Hydroprocessing of crude palm oil at pilot plant scale. Catal Today 156(1–2):38–43CrossRef
30.
Zurück zum Zitat Rozmysłowicz B, Mäki-Arvela P, Lestari S, Simakova OA, Eränen K, Simakova IL, Murzin DY, Salmi TO (2010) Catalytic deoxygenation of tall oil fatty acids over a palladium-mesoporous carbon catalyst: a new source of biofuels. Top Catal 53:1274–1277CrossRef Rozmysłowicz B, Mäki-Arvela P, Lestari S, Simakova OA, Eränen K, Simakova IL, Murzin DY, Salmi TO (2010) Catalytic deoxygenation of tall oil fatty acids over a palladium-mesoporous carbon catalyst: a new source of biofuels. Top Catal 53:1274–1277CrossRef
31.
Zurück zum Zitat Calvin M (1965) The Bakerian lecture, chemical evolution. Proc R Soc Lond A 288(1415):441–446CrossRef Calvin M (1965) The Bakerian lecture, chemical evolution. Proc R Soc Lond A 288(1415):441–446CrossRef
32.
Zurück zum Zitat Volkman JK, Barrett MS, Dunstan AG, Jeffrey SW (1993) Geochemical significance of the occurrence of dinosterol and other 4-methyl sterols in a marine diatom. Org Geochem 20:7–15CrossRef Volkman JK, Barrett MS, Dunstan AG, Jeffrey SW (1993) Geochemical significance of the occurrence of dinosterol and other 4-methyl sterols in a marine diatom. Org Geochem 20:7–15CrossRef
33.
Zurück zum Zitat Dutta RP, Schobert HH (1993) Hydrogenation/dehydrogenation reactions of rosin. Fundam Stud Coal Liquefaction 38(3):1140–1146 Dutta RP, Schobert HH (1993) Hydrogenation/dehydrogenation reactions of rosin. Fundam Stud Coal Liquefaction 38(3):1140–1146
34.
Zurück zum Zitat Zhao C, He J, Lemonidou AA, Li X, Lercher JA (2011) Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes. J Catal 280(1):8–16CrossRef Zhao C, He J, Lemonidou AA, Li X, Lercher JA (2011) Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes. J Catal 280(1):8–16CrossRef
35.
Zurück zum Zitat Şenol OI, Ryymin EM, Viljava TR, Krause AOI (2007) Effect of hydrogen sulphide on the hydrodeoxygenation of aromatic and aliphatic oxygenates on sulphided catalysts. J Mol Catal A Chem 277(1–2):107–112 Şenol OI, Ryymin EM, Viljava TR, Krause AOI (2007) Effect of hydrogen sulphide on the hydrodeoxygenation of aromatic and aliphatic oxygenates on sulphided catalysts. J Mol Catal A Chem 277(1–2):107–112
36.
Zurück zum Zitat Deutsch KL (2012) Copper catalysts in the C–O hydrogenolysis of biorenewable compounds. Dissertation, Iowa State University, Ph.D Deutsch KL (2012) Copper catalysts in the C–O hydrogenolysis of biorenewable compounds. Dissertation, Iowa State University, Ph.D
37.
Zurück zum Zitat Cunningham IM, Overton KH (1974) Steric factors in the hydrogenolysis of some steroidal allylic alcohols by mixed hydrides. J Chem Soc Perkin 1(21):2458–2462CrossRef Cunningham IM, Overton KH (1974) Steric factors in the hydrogenolysis of some steroidal allylic alcohols by mixed hydrides. J Chem Soc Perkin 1(21):2458–2462CrossRef
38.
Zurück zum Zitat Nelan DR (1980) Process for dehydrogenation of sterols to produce Δ4-3-ketosteroids. US patent publication 4226785 A Nelan DR (1980) Process for dehydrogenation of sterols to produce Δ4-3-ketosteroids. US patent publication 4226785 A
39.
Zurück zum Zitat Yin Y, Liu C, Tang LQ, Liu Z (2012) Recoverable Pd/C catalyst mediated dehydrogenation of sterols and an improved synthesis of 1α-hydroxydehydroepiandrosterone. Steroids 77(13):1419–1422CrossRef Yin Y, Liu C, Tang LQ, Liu Z (2012) Recoverable Pd/C catalyst mediated dehydrogenation of sterols and an improved synthesis of 1α-hydroxydehydroepiandrosterone. Steroids 77(13):1419–1422CrossRef
40.
Zurück zum Zitat Yuandong L, Gao L, Wen L, Zong B (2009) Recent advances in heavy oil hydroprocessing technologies. Recent Patents Chem Eng 2(1):22–36CrossRef Yuandong L, Gao L, Wen L, Zong B (2009) Recent advances in heavy oil hydroprocessing technologies. Recent Patents Chem Eng 2(1):22–36CrossRef
Metadaten
Titel
Catalytic upgrading of crude tall oil into a paraffin-rich liquid
verfasst von
Jinto M. Anthonykutty
Juha Linnekoski
Ali Harlin
Antero Laitinen
Juha Lehtonen
Publikationsdatum
01.06.2015
Verlag
Springer Berlin Heidelberg
Erschienen in
Biomass Conversion and Biorefinery / Ausgabe 2/2015
Print ISSN: 2190-6815
Elektronische ISSN: 2190-6823
DOI
https://doi.org/10.1007/s13399-014-0132-8

Weitere Artikel der Ausgabe 2/2015

Biomass Conversion and Biorefinery 2/2015 Zur Ausgabe