EP0839891A2 - Verfahren zur Herstellung von Ölen mit einen Polycycloaromatengehalt unter 3 % verwendbar als Produktöle - Google Patents

Verfahren zur Herstellung von Ölen mit einen Polycycloaromatengehalt unter 3 % verwendbar als Produktöle Download PDF

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Publication number
EP0839891A2
EP0839891A2 EP97500182A EP97500182A EP0839891A2 EP 0839891 A2 EP0839891 A2 EP 0839891A2 EP 97500182 A EP97500182 A EP 97500182A EP 97500182 A EP97500182 A EP 97500182A EP 0839891 A2 EP0839891 A2 EP 0839891A2
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EP
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Prior art keywords
solvent
flow
aromatic
oils
less
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Granted
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EP97500182A
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English (en)
French (fr)
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EP0839891A3 (de
EP0839891B1 (de
Inventor
Rodriguez Juan Miguel Moreno
Serrano Carlos Monjas
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Repsol Petroleo SA
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Repsol Petroleo SA
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Priority claimed from ES9602311A external-priority patent/ES2122917B1/es
Application filed by Repsol Petroleo SA filed Critical Repsol Petroleo SA
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Publication of EP0839891A3 publication Critical patent/EP0839891A3/de
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/28—Recovery of used solvent

Definitions

  • This invention relates to a new process for obtaining aromatic oils having a polycyclic aromatic (PCA) compounds content of less than 3% (IP-346), the aromatic oils so obtained and their application as process oils, such as rubber extenders and oils for printing inks.
  • PCA polycyclic aromatic
  • the components used in the manufacture of rubber, especially in the application for pneumatic tyres, include aromatic oils.
  • aromatic oils are obtained as a by-product of the process of solvent extraction (basically using phenol, furfural, and N-methyl pyrrolidone) of vacuum distillates used as a raw material for the manufacture of lubricant base oils.
  • DAE distillate aromatic extracts
  • PAH polyaromatic hydrocarbons
  • PAC polyaromatic compounds
  • aromatic oils used in the manufacture of rubber are their volatility, which if high leads to the emission of smoke during the manufacturing process.
  • the aromatic oils currently in use are obtained as a by-product in the manufacture of lubricant base oils during solvent extraction of the various vacuum distillates and the deasphalted vacuum bottoms obtained from reduced crude.
  • a flow rich in saturated hydrocarbons having a small solvent content known as mixed raffinate which is the raw material for the manufacture of lubricant base oils
  • a flow known as the mixed extract which mainly consists of solvent and oil rich in aromatic hydrocarbons.
  • the mixed extract flow is passed to a system for the recovery of solvent which is recycled to the extraction column, and an aromatic oil is obtained having a composition which depends on the nature of the vacuum distillate, the conditions under which extraction took place and the efficiency of the extraction column.
  • the process according to this invention can bring about a considerable reduction in polyaromatic hydrocarbons (PAH) content in accordance with US standard EPA-8270 in comparison with the extracts in the state of the art.
  • PAH polyaromatic hydrocarbons
  • the products obtained according to the invention are of a predominantly aromatic nature, with an aromatic hydrocarbons + polar compounds content of more than 45% according to ASTM D-2007, and preferably within the range 60 - 90%.
  • the aromatic oils obtained cease to be regarded as potentially carcinogenic and can be used among other applications as extender oils for rubber or in formulations for printing inks.
  • This invention is based on the following grounds:
  • the invention provides a process for obtaining aromatic oils from which potential carcinogenicity has been removed, from the mixed extract flow obtained in the manufacture of lubricant base oils, a flow which contains a polar solvent, preferably of the group comprising phenol, furfural and N-methyl-2-pyrrolidone, preferably furfural, characterized in that it comprises the stages of:
  • the invention provides aromatic oils which can be regarded as being without carcinogenic potential, obtained in accordance with the process of the first feature of the invention from aromatic extracts obtained from vacuum distillates or deasphalted bottoms having the following characteristics:
  • the invention includes the use of the said low PAC content aromatic oils which can be regarded as being without carcinogenic potential, obtained according to the invention, as process oils such as extenders for rubber, and oils for printing inks.
  • the invention provides rubbers having a high percentage of aromatic groups, such as styrene-butadiene rubbers, which have been extended with the aromatic oils obtained according to the invention.
  • an anti-solvent for example water
  • an anti-solvent for example water
  • An important aspect of the process according to the invention is that the quantity of additional solvent in relation to the flow of the hydrocarbon phase in the mixed extract flow is always less than 1.5:1 and preferably less than 1:1.
  • part of the solvent contained in the flow of starting mixed extract can be removed before the cooling stage in order to achieve an approximately 50% distribution of solvent in the stages prior to settling, or add a hydrocarbonated phase with an initial boiling point (IBP) greater than 200°C, preferably greater than 300°C, to regulate the solvent/solute rate and increase the production capacity of aromatic oils with a PCA content below 3%.
  • IBP initial boiling point
  • a counter-solvent can be added before the first cooling stage in order to increase the selectivity of the solvent contained in the mixed extract flow.
  • the said counter-solvent may be a hydrocarbon flow with a maximum boiling point of less than 160°C, preferably less than 140°C.
  • the cooling temperature prior to the settling stages lies within the range 10 - 90°C, preferably within the range 10 - 60°C and in particular within the range 20 - 50°C.
  • Figure 1 is a flow diagram of the process according to the state of the art for obtaining aromatic oils as by-products in the production of lubricant base oils during the solvent extraction of various vacuum distillates and the deasphalted vacuum bottom obtained from reduced crude.
  • Figure 2 is a flow diagram of the process according to this invention for obtaining aromatic oils with a PAC content of less than 3% from the flow of mixed extract according to the state of the art, in which the process is based on the alternatives of reducing the temperature of the mixed extract flow and the optional addition of an anti-solvent, or of a hydrocar-bonated stream with IBP greater than 200°C.
  • Figure 3 is a flow diagram of the process according to the invention for obtaining the said aromatic oils, in which the process is based on the alternatives of reducing the temperature of the mixed extract flow and adding a counter-solvent.
  • Figure 1 shows a flow diagram of the process according to the state of the art used for the production of aromatic extracts.
  • vacuum distillate (2) and extraction solvent (1) are placed in countercurrent contact in column C-1.
  • the most frequently used solvents are: phenol, furfural and N-methyl-2-pyrrolidone.
  • Solvent (1) which is of greater density, is added to the column at a point close to the top, and distillate (2), of lower density, is introduced at a point close to the bottom.
  • the extraction column may be of various types although one of the most widely used is a mechanically stirred column. In the zone between the two inlet points, countercurrent contact takes place between the solvent and the vacuum distillate. As the solvent flows down the column it will become richer in the aromatic components for which it is most selective. At the same time the rising hydrocarbon flow becomes enriched in saturated hydrocarbons.
  • the column operates with a certain temperature gradient which makes it possible to achieve a greater efficiency in the flow which is rich in saturated hydrocarbons.
  • part of the descending flow (4) is removed from the column, generally at a point below that at which vacuum distillate enters, and is cooled in an external exchanger (E-1) returning to the column (C-1) via (5).
  • the extraction process yields a flow rich in saturated hydrocarbons with a small solvent content (3), known as mixed raffinate, which passes to the recovery system (SR-O) and constitutes the starting material for the manufacture of lubricant base oils, and a flow known as the mixed extract (6), which is predominantly made up of solvent and oil rich in aromatic hydrocarbons.
  • SR-O recovery system
  • the mixed extract (6) which is predominantly made up of solvent and oil rich in aromatic hydrocarbons.
  • the flow of mixed extract (6) is passed to a solvent recovery system (SR-3) which recycles to the extraction column (C-1) and an aromatic oil (28) is obtained whose composition depends on the nature of the vacuum distillate, the conditions under which extraction took place and the efficiency of the extraction column.
  • SR-3 solvent recovery system
  • the aromatic extracts obtained in accordance with this process according to the state of the art have a polyaromatic compounds (PAC) content of more than 3%, as a result of which they are regarded as being potentially carcinogenic.
  • PAC polyaromatic compounds
  • this shows the flow diagram of the process according to the invention based on cooling of the starting mixed extract flow and the optional addition of an anti-solvent, or of a hydrocarbonated stream with IBP greater than 200°C.
  • Figure 2 shows a flow diagram of the process according to the invention for obtaining aromatic oils having a PAC content of less than 3% from the mixed extract flow according to the state of the art (6) by cooling in E-2 (and optionally by the addition of water, or of a hydrocarbonated stream with IBP greater than 200°C (7)), and settling in D-1.
  • the light phase (12) obtained in D-1 is mixed with additional solvent at a higher temperature (14) to achieve satisfactory contact between the phases in mixer M-2 and partial or total redissolution.
  • the new flow, 16, is again cooled in exchanger E-4 and is fed to settler D-2 where a new light phase (18) separates out and is sent to a solvent recovery system (SR-2).
  • Flow (22), which is solvent-free, has a PAC content of less than 3% by weight.
  • the flow of mixed extract is originated from the solvent extraction of a deasphalted vacuum bottom, then the light phase obtained in settler D-1 can be passed directly to solvent recovery (SR-2), as this flow has a PAC content of less than 3%.
  • the flow of mixed extract (6) can be passed to a solvent recovery system (SR-1) to remove some of the solvent before the stage of cooling and settling in D-1.
  • SR-1 solvent recovery system
  • the solvent removed in SR-1 is passed together with the additional solvent required for mixing with the light flow from D-1 for further reextraction and settling in D-2.
  • Flow (6) leaves column C-1 at a temperature which generally varies within the range 50 - 115°C.
  • This flow has a solvent content which likewise varies within the range 70 - 95%, most frequently being 80-85%.
  • the oil contained in this flow has a polyaromatic hydrocarbons content which varies within the range 4 - 30%.
  • This flow is cooled to a temperature within the range 10 - 90°C, preferably 20 - 50°C, in exchanger E-2.
  • the cold flow from E2 is passed to settler D-1, where a light phase (12) having a low solvent content and a PAC content in the range 0.5 - 10%, fundamentally depending on the type of vacuum distillate (2), separates out.
  • the light flow leaving D-1 is mixed (M-2) with solvent at a higher temperature within the range 30 - 160°C to dissolve most of the hydrocarbon components and is again cooled to the desired settling temperature, generally within the range 10 - 90°C and preferably within the range 20 - 50°C, in exchanger E-4.
  • the cold flow (17) is passed to settler D-2 where a light phase (18) having a low solvent and polyaromatic compounds content again separates out.
  • Flow (18) is passed to system SR-2 for the removal of the solvent.
  • an anti-solvent (7) or a hydrocarbonated fraction with IBP greater than 200°C (7) may be added to the mixed extract flow, which, in order to simplify, have both been considered as the same stream in fig. 2.
  • Figure 3 shows the flow diagram for the process based on temperature reduction, the addition of a counter-solvent and reextraction.
  • a counter-solvent (7) is added to the flow of mixed extract (6), and the resulting flow is cooled in exchanger E-2.
  • the resulting flow (9) is passed to a mixer M-1 in order to achieve a satisfactory level of contact between the phases and then to a settler, D-1, where the phases separate out.
  • the light phase (12) is mixed with additional solvent (14) in a mixer M-2, and is again cooled in exchanger E-4, from which it passes to settler D-2.
  • the light phase (18) leaving D-2 is passed to a system SR-2 for the recovery of solvent and counter-solvent which are recycled to the process and a flow (22) having a PAC content of less than 3% is obtained.
  • the flow of mixed extract originates from the solvent extraction of a deasphalted vacuum bottoms then the light phase obtained in settler D-1 can be passed directly to solvent recovery SR-3 if its PAC content is less than 3%.
  • the flow of mixed extract (6) can be passed to a solvent recovery system (SR-1) to remove part of the solvent before the stage of cooling and settling in D-1.
  • SR-1 solvent recovery system
  • the solvent removed in SR-1 is passed together with the additional solvent required for mixing with the light flow from D-1 for further reextraction and settling in D-2.
  • the system comprising M-2, E-4 and D-2 may be replaced by countercurrent extraction.
  • flow (7) may be added after the cooling stage in E-2.
  • the cold flow from E-2 passes to mixer M-1 in order to achieve satisfactory contact between the phases and is passed to settler D-1 where a light phase consisting of solvent, counter-solvent and a mixture of hydrocarbons having a PAC content in the range 0.5 - 15%, depending fundamentally on the nature of vacuum distillate 2, separates out.
  • the light flow leaving D-1 is mixed (M-2) with solvent previously cooled in E-3 to a temperature below the boiling point of the most volatile component, preferably 30 - 50°C.
  • solvent previously cooled in E-3 to a temperature below the boiling point of the most volatile component, preferably 30 - 50°C.
  • it can be cooled again in exchanger E-4 to the desired settling temperature, generally within the range 15 - 90°C and preferably within the range 15 - 50°C.
  • Flow (17) which is cold, is passed to settler D-2 where a light phase (18) consisting of counter-solvent, solvent and a mixture of hydrocarbons having a low polyaromatic compounds content again settles out and is passed to system SR-2 to remove solvent and counter-solvent.
  • This example includes the results obtained in the treatment of the mixed extract flow (6) obtained from furfural extraction to obtain SN-600.
  • the outlet temperature of this flow was 85 - 95°C.
  • the flow was cooled at different temperatures in E2 and settled in D-1.
  • the light flow from D-1 was mixed with additional furfural at a higher temperature in M-2.
  • the resulting flow (16) was cooled to the same temperature as in E-2 and settled in D-2.
  • the results obtained were:
  • This example includes the results obtained from the treatment of the mixed extract flow 6 obtained from the furfural extraction of deasphalted vacuum bottoms.
  • the outlet temperature of this flow was 100 - 110°C.
  • the flow was cooled to different temperatures in E2 and settled in D-1.
  • the light flow from D-1 had a PAC content of less than 3% once the solvent had been removed, and it was not reextracted for this reason.
  • This example includes the results obtained from the treatment of the mixed extract flow, 6, obtained from furfural extraction to obtain a SN-150 base oil.
  • the outlet temperature of this flow was 80°C.
  • the flow was cooled to 40°C in E2 and settled in D-1.
  • the light flow from D-1 was mixed with additional furfural at a higher temperature in M-2.
  • the resulting flow 16 was cooled to the same temperature as in E-2 and settled in D-2.
  • the results obtained were: Experiment no.
  • This example includes the results obtained in treatment of the mixed extract flow, 6, obtained from furfural extraction to obtain SN-600.
  • the results obtained by cooling and reextracting at 40°C are compared with those obtained under similar conditions but with the addition of water to the flow 6.
  • the results obtained were: Experiment no.
  • This example includes the results obtained from the treatment of the mixed extract flow, 6, obtained from furfural extraction to obtain SN-600.
  • the results obtained by cooling and reextracting at 40°C are compared with those obtained under similar temperature conditions but with the addition of a counter-solvent prior to cooling in E-2.
  • the results obtained were: Experiment no.
  • This example includes the results obtained from the treatment of the mixed extract flow, 6, obtained from furfural extraction to obtain SN-600.
  • the results obtained by cooling and reextracting at 40°C are compared with those obtained under similar temperature conditions but with removing part of the furfural from the flow 6 in SR-1 before cooling in E-2 and reextracting the light phase from D-1 with additional furfural in order to make up the total furfural/extract ratio used in example 1.
  • This example contains the results obtained in the treatment of the flow of mixed extract 6, resulting from the extraction with furfural to obtain SN-600.
  • the results obtained by cooling and re-extracting at 40°C are compared with ones obtained in similar conditions of temperature but adding a hydrocarbonated stream with IBP greater than 200°C to the flow of mixed extract 6, before cooling at E-2 and extracting the light phase from D-1 with additional furfural to reduce the PCA content to below 3%.
  • One of the objectives of this invention is to develop aromatic oils having a low PAC content which will not be regarded as potentially carcinogenic for application as rubber extenders.
  • the table below includes the properties of the vulcanizates: Mixtures Mixture A Mixture B Mixture D Oil used A B D Property Shore hardness A 51.0 51.9 52.7 Resilience, % 30 30 28.5 100% deformation force, MPa 1.13 1.17 1.10 300% deformation force, MPa 4.50 4.67 4.23 500% deformation force, MPa 10.51 10.75 9.41 Tensile strength, MPa 16.31 16.32 17.14 Elongation on fracture, % 694 680 769 Tear resistance, N 55.3 53.7 57.2
EP19970500182 1996-10-31 1997-10-30 Verfahren zur Herstellung von Ölen mit einem Gehalt an polycyclischen Aromaten von weniger als 3%, verwendbar als Prozessöle Expired - Lifetime EP0839891B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
ES9602311A ES2122917B1 (es) 1996-10-31 1996-10-31 Proceso para la obtencion de aceites aromaticos con un contenido en compuestos aromaticos policiclicos inferior al 3% utiles como extenso res de cauchos.
ES9602311 1996-10-31
ES9702226A ES2137123B1 (es) 1996-10-31 1997-10-28 Mejoras introducidas en el objeto de la patente principal 9602311, presentada el 31 de octubre de 1996, sobre: un proceso para la obtencion de aceites aromaticos con un contenido en compuestos aromaticos policiclicos inferior al 38"
ES9702226 1997-10-28

Publications (3)

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EP0839891A2 true EP0839891A2 (de) 1998-05-06
EP0839891A3 EP0839891A3 (de) 1998-07-29
EP0839891B1 EP0839891B1 (de) 2004-06-16

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EP19970500182 Expired - Lifetime EP0839891B1 (de) 1996-10-31 1997-10-30 Verfahren zur Herstellung von Ölen mit einem Gehalt an polycyclischen Aromaten von weniger als 3%, verwendbar als Prozessöle

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EP (1) EP0839891B1 (de)
BR (1) BR9715050A (de)
DE (1) DE69729526T2 (de)
ES (1) ES2224215T3 (de)

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EP0940462A2 (de) * 1997-06-27 1999-09-08 Bridgestone Corporation Verbessertes öl mit hohem aromatengehalt, gummizusammensetzung und mit öl gestreckter, synthetischer gummi, beide hergestellt unter verwendung des hocharomatischen öles
EP0940462A4 (de) * 1997-06-27 2005-03-02 Bridgestone Corp Verbessertes öl mit hohem aromatengehalt, gummizusammensetzung und mit öl gestreckter, synthetischer gummi, beide hergestellt unter verwendung des hocharomatischen öles
EP1031621A2 (de) * 1999-02-26 2000-08-30 Idemitsu Kosan Co., Ltd. Prozessöle, Verfahren zu ihrer Herstellung und Kautschuk-Zusammensetzungen
EP1031621A3 (de) * 1999-02-26 2000-11-29 Idemitsu Kosan Co., Ltd. Prozessöle, Verfahren zu ihrer Herstellung und Kautschuk-Zusammensetzungen
US6399697B1 (en) 1999-02-26 2002-06-04 Idemitsu Kosan Co., Ltd. Process oil, process for producing the same and rubber composition
US6605695B2 (en) 1999-02-26 2003-08-12 Idemitsu Kosan Co., Ltd. Process oil, process for producing the same and rubber composition
US6802960B1 (en) 1999-03-02 2004-10-12 Bp Oil International Limited Two stage extraction oil treatment process
EP1106673A2 (de) * 1999-12-06 2001-06-13 Shell Internationale Researchmaatschappij B.V. Entfernung von polycyclischen aromatischen Verbindungen aus Extrakten
EP1106673A3 (de) * 1999-12-06 2002-02-06 Shell Internationale Researchmaatschappij B.V. Entfernung von polycyclischen aromatischen Verbindungen aus Extrakten
KR20020076626A (ko) * 2001-03-29 2002-10-11 금호산업 주식회사 저독성 연화제를 사용하여 내커팅/내칩핑 특성이 우수한트럭버스용 레디얼타이어 트래드고무조성물
KR20020076627A (ko) * 2001-03-29 2002-10-11 금호산업 주식회사 저독성 연화제를 사용하여 내열특성이 우수한 트럭버스용레디얼타이어 트래드고무조성물
EP1433833A4 (de) * 2001-10-02 2010-09-22 Japan Energy Corp Prozessöl und verfahren zu seiner herstellung
EP1433833A1 (de) * 2001-10-02 2004-06-30 Japan Energy Corporation Prozessöl und verfahren zu seiner herstellung
EP1493596A1 (de) 2003-06-30 2005-01-05 The Goodyear Tire & Rubber Company Luftreifen mit einer komponente enthaltend ein prozessöl mit niedrigen gehalt an polycyclischen aromaten
US7193004B2 (en) 2003-06-30 2007-03-20 The Goodyear Tire & Rubber Company Pneumatic tire having a component containing low PCA oil
EP1637353A1 (de) 2004-09-17 2006-03-22 The Goodyear Tire & Rubber Company Reifen mit Lauffläche, der eine nicht mischbare Kautschukmischung und Silica enthält
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US7406990B2 (en) 2005-08-10 2008-08-05 The Goodyear Tire & Rubber Company Runflat tire with sidewall component containing high strength glass bubbles
US7968630B2 (en) 2005-09-08 2011-06-28 The Goodyear Tire & Rubber Company Pneumatic tire containing zinc porphyrin compound
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US8939184B2 (en) 2006-12-21 2015-01-27 Bridgestone Americas Tire Operations, Llc Rubber composition and pneumatic tire using same
EP2113021B1 (de) * 2007-02-21 2019-06-12 BP p.l.c. Verfahren zur herstellung von basisöl und ihr verwendung
WO2011125042A1 (fr) * 2010-04-09 2011-10-13 Total Raffinage Marketing Procede de purification des extraits aromatiques contenant des composes polycycliques aromatiques
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EP2571961B1 (de) 2010-05-17 2022-03-02 PT PERTAMINA (Persero) Verfahren zur herstellung von prozessöl mit geringem gehalt an polyaromatischen kohlenwasserstoffen und erhaltenes produkt
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US9512366B2 (en) 2010-05-17 2016-12-06 Pt Pertamina (Persero) Process to produce process oil with low polyaromatic hydrocarbon content
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DE69729526T2 (de) 2005-08-18
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DE69729526D1 (de) 2004-07-22
BR9715050A (pt) 2001-05-22

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