EP0957150A1 - Teer- und/oder Ölpech mit geringem Gehalt an polycyclischen aromatischen Stoffen und dessen Herstellung - Google Patents

Teer- und/oder Ölpech mit geringem Gehalt an polycyclischen aromatischen Stoffen und dessen Herstellung Download PDF

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Publication number
EP0957150A1
EP0957150A1 EP98830298A EP98830298A EP0957150A1 EP 0957150 A1 EP0957150 A1 EP 0957150A1 EP 98830298 A EP98830298 A EP 98830298A EP 98830298 A EP98830298 A EP 98830298A EP 0957150 A1 EP0957150 A1 EP 0957150A1
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EP
European Patent Office
Prior art keywords
benzo
pitch
evaporator
residue
ppm
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98830298A
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English (en)
French (fr)
Inventor
Martino Caranti
Remo Chiettini
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Carbochimica SpA
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Carbochimica SpA
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Publication date
Application filed by Carbochimica SpA filed Critical Carbochimica SpA
Priority to EP98830298A priority Critical patent/EP0957150A1/de
Publication of EP0957150A1 publication Critical patent/EP0957150A1/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
    • C10C3/00—Working-up pitch, asphalt, bitumen
    • C10C3/06—Working-up pitch, asphalt, bitumen by distillation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
    • C10C1/00—Working-up tar
    • C10C1/04—Working-up tar by distillation

Definitions

  • the present invention relates in general to a tar or oil pitch with a low content of polycyclic aromatic substances.
  • the present invention relates to a pitch of the aforementioned type which is substantially free of benzo[a]pyrene.
  • tar pitch and "oil pitch” are intended to define residues which can be produced, respectively, by the distillation of coal tar and of petroleum fractions and/or residues thereof resulting from processes such as thermal or catalytic cracking.
  • the present invention also relates to a method of producing tar and/or oil pitches which are substantially free of benzo [a] pyrene.
  • pitches are widely used in various industrial applications but they have the serious disadvantage of containing various aromatic compounds which are suspected of having or which have carcinogenic properties, and the presence of which leads to considerable problems due to environmental impact and constitutes a potential hazard to workers' health.
  • benzo[a]pyrene is benzo[a]pyrene; this compound, which has been confirmed to be carcinogenic, is found in concentrations of about 0.5-1.5% by weight in soft pitches derived from tar and about 0.1-1% by weight in soft pitches derived from petroleum.
  • the concentration of benzo[a]pyrene is reduced as a result of the second distillation and is generally within the range of 4,000-12,000 ppm.
  • benzo[a]pyrene in pitches is in any case not desirable and, moreover, the current regulations classify pitches having a benzo[a]pyrene content greater than 50 ppm as carcinogenic products and provide for particular care and attention during their handling.
  • European patent EP 0 510 315 describes a method of producing pitches having a benzo[a]pyrene content of less than 50 ppm in which a residue of the primary distillation of tar is distilled at a temperature of 300-380°C and at a pressure of less than 1 mbar in an evaporator having a heat-exchange area:volume ratio of between 330 and 10,000 m 2 /m 3 , with the residue spending a period of 2-10 minutes in the evaporator.
  • a filtered tar pitch having a low softening point is distilled in a thin-layer evaporator at a temperature of 300-425°C and at a pressure no greater than 10 mbars.
  • pitches having optical anistropy of less than 2% are thus produced by distillation in thin-layer evaporators.
  • thin-layer or thin-film evaporators have the disadvantage that it is extremely difficult to achieve a uniform layer of pitch on their exchange surfaces so that exchange efficiency is not particularly high.
  • the technical problem upon which the present invention is based is that of providing tar and/or oil pitches which are substantially free of benzo[a]pyrene and which, at the same time, also have low optical anisotropy so that they can be used in all industrial applications which require substantially isotropic pitches.
  • a tar and/or oil pitch characterized in that it has a benzo[a]pyrene content less than or equal to 5 ppm and optical anisotropy of less than 1%.
  • the pitches of the invention are preferably characterized in that they are free of benzo[a]pyrene.
  • the pitches of the invention are further characterized in that they have a content of less than 50 ppm, preferably less than 5 ppm, of each of the following polycyclic aromatic compounds: benzo[a]anthracene, chrysene, benzo[a]fluoranthene, benzo[k]fluoranthene, benzo[b]fluoranthene, benzo[e]pyrene, indeno[1,2,3-c,d]pyrene, dibenzo[a,h]anthracene and benzo[g,h,i]perylene.
  • the pitches of the invention are further characterized in that they are free of the above-mentioned polycyclic aromatic compounds.
  • the present invention also relates to a method of preparing tar and/or oil pitches substantially free of benzo[a]pyrene, the method comprising the steps of:
  • the period for which the residue or the mixture is distilled in the evaporator is between 20 minutes and 10 hours.
  • the pitch produced in the manner described above also has optical anisotropy of less than 1%.
  • the removal of the benzo[a]pyrene from the above-mentioned residue or from the above-mentioned mixture by distillation for long periods is not accompanied by the formation of unacceptable quantities of mesophase in the final pitch.
  • the operative temperature and vacuum conditions of the evaporator and the distillation time can be selected within the above-mentioned ranges according to the chemico-physical characteristics and the benzo[a]pyrene content of the residue or of the mixture to be distilled so as to produce a final pitch substantially free of this compound.
  • the pitches produced by the method of the invention can be produced free of the following polycyclic aromatic compounds: benzo[a]anthracene, chrysene, benzo[a]fluoranthene, benzo[k]fluoranthene, benzo[b]fluoranthene, benzo[e]pyrene, indeno[1,2,3-c,d]pyrene, dibenzo[a,h]anthracene and benzo[g,h,i]perylene, or, alternatively, have a content of less than 50 ppm, preferably less than 5 ppm, of the above-mentioned compounds.
  • the apparatus used for the distillation of the residue from the primary distillation of tar and/or petroleum or of the mixture of this residue with tar and/or petroleum is of particular importance and should have a heat-exchange area:volume ratio of between 1 m 2 /m 3 and 200 m 2 /m 3 , preferably between 5 m 2 /m 3 and 60 m 2 /m 3 , and should enable the residue or the mixture to be mixed continuously during distillation.
  • the distillation of the above-mentioned residue or of the above-mentioned mixture is performed in an evaporator which at the same time acts as a mixer and which comprises a cylindrical body provided with a jacket for heating its internal wall, at least one inlet opening for the residue or the mixture, at least one outlet opening for the final pitch, at least one distillate-recovery opening connected to a system for applying a reduced pressure to the interior of the cylindrical body, and a rotary shaft which can be heated and is supported for rotating in the cylindrical body, and along the axis of which radial mixing elements, which may also be capable of being heated, are disposed.
  • the evaporator further comprises opposed mixing elements fixed radially to the internal wall of the cylindrical body and interposed between the radial elements in order to facilitate the removal of the residue or of the mixture from the peripheral surface of the shaft and from the surfaces of the mixing elements.
  • the radial mixing elements comprise disc sectors to which mixing bars are fixed and the opposed mixing elements are substantially hook-shaped with at least one portion skimming the disc sectors and at least one portion skimming the peripheral surface of the shaft.
  • the rotary shaft of the evaporator is heated by means of a diathermic fluid which flows through an internal circuit thereof and the mixing elements (the disc sectors and the bars) may also be heated by the same fluid; in this case, ducts through which the fluid can flow and which are in communication with the heating circuit of the rotary shaft are formed in the mixing element.
  • the distillation of the residue of the primary distillation of tar and/or petroleum or of the mixture of the residue with tar and/or petroleum comprises the steps of:
  • the evaporator comprises the above-mentioned opposed fixed mixing elements, these facilitate the removal of the residue or of the mixture from the peripheral surface of the rotary shaft and from the surfaces of the mixing elements.
  • evaporator-mixers which may be used continuously, semi-continuously or for batch operation, have the advantage of highly efficient heat exchange and mass transfer since the product treated therein is mixed continuously in conditions permitting thermal exchange with contact surfaces all of which can be heated and which at the same time are cleaned of the product by any opposed mixing elements.
  • evaporators are known per se and are used for performing various processes such as drying, evaporation, sublimation, etc., by the thermal and mechanical treatment of products in liquid, paste or powder form.
  • the pitches produced by the method of the invention can be used in various industrial applications for which an isotropic pitch is required.
  • They can be used, for example, as binding agents in the production of electrodes, refractory materials or special graphitized materials, as impregnating agents, or as a raw material for the production of paints, pitch coke and rechargeable batteries.
  • At least one viscosity-modifying agent is generally added to the pitches of the invention before use.
  • the pitch thus produced is advantageously used directly without the aid of viscosity-modifying agents.
  • Viscosity-modifying agents which may be used are, for example, aromatic oils, resins, bituminous products miscible with pitches, etc., selected in dependence on the final use of the pitches.
  • the at least one viscosity-modifying agent added to the pitches of the invention is advantageously substantially free of benzo[a]pyrene so that compositions comprising the pitches of the invention and at least one such agent can be used in the various applications without problems of environmental impact or risk to workers' health.
  • the drawing is a schematic side view of an evaporator, partially open, which is usable for implementing the method of the invention, and is of the type described, for example, in US patent 5,121,992, the text of which should be referred to for a detailed description.
  • an evaporator generally indicated R, comprises a cylindrical body 1 arranged with its longitudinal axis horizontal, surrounded by a heating jacket 2 through which a diathermic fluid is intended to flow, and having an inlet opening 3 for a residue or a mixture to be distilled, an outlet opening 4 for the final pitch, and a distillate-recovery opening 5 connected to a system (not shown) for applying a reduced pressure to the interior of the cylindrical body 1.
  • a shaft 6 supported for rotating in the cylindrical body 1 about a rotation axis A is heated by a diathermic fluid which is admitted to its interior through an opening 7 and emerges therefrom through an opening 8.
  • a motor M is provided for driving the shaft 6 at a speed of between 1 and 150 revolutions/minute.
  • radial mixing elements 9 Arranged along the longitudinal axis of the shaft 6 are radial mixing elements 9 between which opposed mixing elements 10, arranged radially on the internal wall 13 of the cylindrical body 1, are interposed.
  • the mixing elements 9 comprise disc sectors 11 to which mixing bars 12 are fixed.
  • the disc sectors 11 rotate together with the shaft 6 and the bars 12 pass a small distance from the internal wall 13 of the cylindrical body 1.
  • the internal wall 13 is thus cleaned of the product subjected to distillation in the evaporator R.
  • the opposed mixing elements 10 are substantially hook-shaped and each comprises a support 17 and portions 18, 20 and 21.
  • the support 17 is arranged radially relative to the shaft 6 and is joined to the portion 18 which is parallel to the axis of rotation A.
  • the portion 18 forms, together with the respective portion of the mixing bar 12, a slot 19 through which the bar 12 can move.
  • the product to be treated is thus also forced between the portion 18 and the internal wall 13 of the cylindrical body 1 and is mixed continuously.
  • the portion 18 in turn is joined, in the region of the disc sector 11, to a radial portion 20 which extends as far as the vicinity of the shaft 6.
  • this portion 20 is to remove the product from the disc sectors 11, preventing the formation of deposits on these sectors and, at the same time, to mix the product between the portion 20 and the disc sectors 11, thus improving the mixing action.
  • the portion 20 in turn is joined to a portion 21 parallel to the peripheral surface of the shaft 6 and inclined away from the section 20 in the direction of rotation of the shaft 6.
  • This portion 21 is to remove the product from the peripheral surface of the shaft 6.
  • the drawing shows opposed mixing elements 10 which skim the surface of the disc sectors 11 on one side.
  • Similar opposed mixing elements may be provided in the cylindrical body 1 in an opposite arrangement so as to remove the product from the other surface of the disc sectors 11 with a corresponding radial portion, and from the peripheral surface of the shaft 6 which is not cleaned by the portion 21.
  • a residue from the primary distillation of tar and/or petroleum or a mixture of this residue with tar and/or petroleum is supplied to the mixer R through the inlet opening 3 and is taken from this inlet and worked mechanically by the mixing elements 9 of the shaft 6 which are kept rotating at a suitable speed.
  • the residue or mixture is then mixed continuously by the mixing elements 9 in a relationship permitting thermal exchange with the internal wall 13 of the cylindrical body 1 and with the shaft 6 which are kept at a predetermined temperature and in conditions of reduced pressure in the cylindrical body 1, applied through the opening 5 thereof, through which the distillate is also recovered.
  • the mixing of the residue or of the mixture takes place substantially in the space 14, in the slot 19 and between the radial portion 20 and the disc sectors 11 and, at the same time, it is removed from the surfaces of the disc sectors 11 by means of the radial portions 20 and from the peripheral surface of the shaft 6 by means of the portions 21 of the opposed mixing elements 10.
  • evaporator for example, to its shape, its size and the arrangement of its component parts, or it may have one or more inlet and outlet openings and one or more heating and cooling jackets, for example, in order to achieve a temperature gradient and thus to implement an exchange of heat for the purposes of particular working requirements.
  • the method of the invention may also be implemented with the use of other evaporators based on the same operating principle as the evaporator described above, for example, evaporators of the type described in US patent 5,407,266 comprising two or more rotary shafts which carry radial mixing elements mating with one another in a manner such that the surfaces of the mixing elements of one shaft are continuously cleaned by the mixing elements of another shaft and vice versa during the processing of the product.
  • evaporators of the type described in US patent 5,407,266 comprising two or more rotary shafts which carry radial mixing elements mating with one another in a manner such that the surfaces of the mixing elements of one shaft are continuously cleaned by the mixing elements of another shaft and vice versa during the processing of the product.
  • This evaporator had a heat-exchange area:volume ratio of about 50 m 2 /m 3 .
  • the internal wall of the evaporator was heated to a temperature of about 320°C, the pressure inside the evaporator was brought to about 0.4 mbars, and the rotary shaft was rotated at a constant speed of 60 revolutions/minute.
  • the above-mentioned pitch showed no trace of benzo ⁇ a]pyrene or of the other polycyclic aromatic compounds given in Tables 1A and 1B, determined by gas-liquid chromatography (GLC) and liquid-liquid chromatography (HPLC) and also had zero optical anisotropy.
  • the internal wall of the evaporator was heated to a temperature of about 320°C, the pressure inside the evaporator was brought to about 0.4 mbars, and the rotary shaft was rotated at a constant speed of 30 revolutions/minute.
  • the above-mentioned pitch showed no trace of benzo[a]pyrene or of the other polycyclic aromatic compounds given in Tables 2A and 2B, determined by gas-liquid chromatography (GLC) and liquid-liquid chromatography (HPLC), and also had zero optical anisotropy.
  • the internal wall of the evaporator was heated to a temperature of about 320°C, the pressure inside the evaporator was brought to about 0.4 mbars, and the rotary shaft was rotated at a constant speed of 60 revolutions/minute.
  • the pitch showed no trace of benzo[a]pyrene or of the other polycyclic aromatic compounds given in the tables of the previous examples, determined by gas-liquid chromatography (GLC) and liquid-liquid chromatography (HPLC), and also had zero optical anisotropy.
  • This evaporator had a heat-exchange area:volume ratio of about 50 m 2 /m 3 .
  • the internal wall of the evaporator was heated to a temperature of about 320°C, the pressure inside the evaporator was brought to about 0.4 mbars, and the rotary shaft was rotated at a constant speed of 60 revolutions/minute.
  • the above-mentioned pitch showed no trace of benzo[a]pyrene or of the other aromatic compounds given in Tables 1A and 4B, determined by gas-liquid chromatography (GLC) and liquid-liquid chromatography (HPLC), and also had zero optical anisotropy.
  • pitches will in any case always be produced substantially free of benzo[a]pyrene and will have optical anisotropy of less than 1%.
  • a pitch having the following characteristics given in Table 5A was thus produced: Parameters Analytical method Value Mettler softening temperature (°C) ASTM D 3104 107.0 Insoluble in quinoline Q.I. (% by weight) ISO 6791 19.4 Insoluble in toluene, T.I.
  • This pitch can advantageously be used as a binding agent for the production of electrodes, for example, for the steel industry, the aluminium industry, etc.
  • This pitch can advantageously be used as an impregnation agent for electrodes and also as an impregnation and/or binding agent for aluminium anodes and for refractory materials.
  • pitches produced in accordance with the method of the invention with different viscosity-modifying agents free of benzo[a]pyrene, having different characteristics from those of the oils mentioned in Examples 5 and 6, and/or will be able to use different mixing ratios so as to produce pitches more specifically suitable for individual uses/users' various requirements for characteristics/workability.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Civil Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Structural Engineering (AREA)
  • Working-Up Tar And Pitch (AREA)
EP98830298A 1998-05-15 1998-05-15 Teer- und/oder Ölpech mit geringem Gehalt an polycyclischen aromatischen Stoffen und dessen Herstellung Withdrawn EP0957150A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP98830298A EP0957150A1 (de) 1998-05-15 1998-05-15 Teer- und/oder Ölpech mit geringem Gehalt an polycyclischen aromatischen Stoffen und dessen Herstellung

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EP98830298A EP0957150A1 (de) 1998-05-15 1998-05-15 Teer- und/oder Ölpech mit geringem Gehalt an polycyclischen aromatischen Stoffen und dessen Herstellung

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005068391A1 (de) * 2004-01-17 2005-07-28 Rütgers Chemicals AG Herstellung von umweltfreundlichen kohlenstoffgebundenen feuerfesterzeugnissen im kaltmischverfahren
US7033485B2 (en) 2001-05-11 2006-04-25 Koppers Industries Of Delaware, Inc. Coal tar and hydrocarbon mixture pitch production using a high efficiency evaporative distillation process
CN101787297B (zh) * 2010-01-25 2013-03-06 重庆星博化工有限公司 一种煤焦油加工的工艺方法及装置
WO2021015824A1 (en) 2019-07-23 2021-01-28 Koppers Delaware, Inc. Heat treatment process and system for increased pitch yields
CN113025361A (zh) * 2021-03-08 2021-06-25 南京浩轩化工科技有限公司 一种煤沥青制备加工方法
EP4215481A1 (de) * 2022-01-24 2023-07-26 Rain Carbon bv Verbessertes kohlenstoffvorläufermaterial

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5413533A (en) * 1977-07-04 1979-02-01 Kawatetsu Kagaku Kk Method of reducing 3*4 benzpyrene in coal tar pitch
US5121992A (en) * 1989-10-04 1992-06-16 List Ag Mixing kneader
EP0510315A1 (de) * 1991-04-20 1992-10-28 Rütgerswerke Aktiengesellschaft Steinkohlenteerpech, seine Herstellung und Verwendung
US5746906A (en) * 1995-08-10 1998-05-05 Koppers Industries, Inc. Coal tar pitch blend having low polycyclic aromatic hydrocarbon content and method of making thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5413533A (en) * 1977-07-04 1979-02-01 Kawatetsu Kagaku Kk Method of reducing 3*4 benzpyrene in coal tar pitch
US5121992A (en) * 1989-10-04 1992-06-16 List Ag Mixing kneader
EP0510315A1 (de) * 1991-04-20 1992-10-28 Rütgerswerke Aktiengesellschaft Steinkohlenteerpech, seine Herstellung und Verwendung
US5746906A (en) * 1995-08-10 1998-05-05 Koppers Industries, Inc. Coal tar pitch blend having low polycyclic aromatic hydrocarbon content and method of making thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 7910, Derwent World Patents Index; Class HO9, AN 79-19202B, XP002081348 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7033485B2 (en) 2001-05-11 2006-04-25 Koppers Industries Of Delaware, Inc. Coal tar and hydrocarbon mixture pitch production using a high efficiency evaporative distillation process
US7066997B2 (en) 2001-05-11 2006-06-27 Koppers Delaware, Inc. Coal tar and hydrocarbon mixture pitch and the preparation and use thereof
US7465387B2 (en) 2001-05-11 2008-12-16 Koppers Delaware, Inc. Coal tar and hydrocarbon mixture pitch and the preparation and use thereof
WO2005068391A1 (de) * 2004-01-17 2005-07-28 Rütgers Chemicals AG Herstellung von umweltfreundlichen kohlenstoffgebundenen feuerfesterzeugnissen im kaltmischverfahren
US7772145B2 (en) 2004-01-17 2010-08-10 Rütgers Chemicals AG Manufacture of environmentally friendly carbon-bonded refractory product in the cold mixing process
CN101787297B (zh) * 2010-01-25 2013-03-06 重庆星博化工有限公司 一种煤焦油加工的工艺方法及装置
WO2021015824A1 (en) 2019-07-23 2021-01-28 Koppers Delaware, Inc. Heat treatment process and system for increased pitch yields
US11248172B2 (en) 2019-07-23 2022-02-15 Koppers Delaware, Inc. Heat treatment process and system for increased pitch yields
US11624029B2 (en) 2019-07-23 2023-04-11 Koppers Delaware, Inc. Heat treatment process for increased pitch yields
EP4004147A4 (de) * 2019-07-23 2023-08-09 Koppers Delaware, Inc. Wärmebehandlungsverfahren und -system für erhöhte pechausbeute
CN113025361A (zh) * 2021-03-08 2021-06-25 南京浩轩化工科技有限公司 一种煤沥青制备加工方法
EP4215481A1 (de) * 2022-01-24 2023-07-26 Rain Carbon bv Verbessertes kohlenstoffvorläufermaterial
WO2023139288A1 (en) * 2022-01-24 2023-07-27 Rain Carbon Bv An improved carbon precursor material

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