EP0887087A2 - Process for removing polychlorobiphenyls from mineral oils - Google Patents
Process for removing polychlorobiphenyls from mineral oils Download PDFInfo
- Publication number
- EP0887087A2 EP0887087A2 EP98110525A EP98110525A EP0887087A2 EP 0887087 A2 EP0887087 A2 EP 0887087A2 EP 98110525 A EP98110525 A EP 98110525A EP 98110525 A EP98110525 A EP 98110525A EP 0887087 A2 EP0887087 A2 EP 0887087A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- accordance
- polychlorobiphenyls
- catalyst
- hydrogenation catalyst
- mineral oils
- Prior art date
- 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- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 21
- 239000002480 mineral oil Substances 0.000 title claims description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 235000010446 mineral oil Nutrition 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 2
- 229910052750 molybdenum Inorganic materials 0.000 claims 2
- 239000011733 molybdenum Substances 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 239000010941 cobalt Substances 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 239000010937 tungsten Substances 0.000 claims 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000003444 phase transfer catalyst Substances 0.000 description 4
- 230000036632 reaction speed Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000007038 hydrochlorination reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 description 1
- MOWMLACGTDMJRV-UHFFFAOYSA-N nickel tungsten Chemical compound [Ni].[W] MOWMLACGTDMJRV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- -1 superoxide ions Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/37—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by reduction, e.g. hydrogenation
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/22—Organic substances containing halogen
Definitions
- the present invention concerns a process for removing polychlorobiphenyls (PCBs) from mineral oils, and especially from dielectric oils contaminated in electrical equipment.
- PCBs polychlorobiphenyls
- the latter compound may to all intents and purposes be considered a component of the mineral oil.
- the said catalyst may be chosen among the families of typical catalysts for "hydrotreating/hydrogenation/saturation” and “hydrorefining” processes, that is to say, catalysts that will activate substitution reactions of the more common heteroatoms, nitrogen, sulphur and oxygen being cases in point, using molecular hydrogen as the hydrogen source.
- Nickel-Molybdenum Ni/Mo
- Co/Mo Cobalt-Molybdenum
- Ni/W Nickel-Tungsten
- the invented process is capable of application to mineral oils contaminated with PCBs in a wide range of concentrations, preferably between 5 and 50,000 ppm.
- reaction speed diminishes in such a manner as to render the process not particularly suitable for industrial applications.
- the reaction speed will be raised by operating at higher pressures, preferably between 5 and 50 bar, and at higher temperatures, preferably between 250°C and 400°C.
- the initial concentration of the PCBs in the examples here described was in the range between 730 ppm and 123 ppm.
- the hydrogenation catalyst was Ni/Mo and the temperature was 300° C.
- the pressure was between 5 and 45 bar.
- CSTR continuous stirred tank reactor
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Water Treatment By Sorption (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
In a batch reactor (1), complete with heat exchanger (2) and agitator (3), the
dielectric oil (4) contaminated by polychlorobiphenyls is placed in contact with
gaseous hydrogen (5) and caused to react therewith at temperatures between 250
and 400°C and pressures between 5 and 50 bar in the presence of a hydrogenation
catalyst (6). The decontaminated oil (7) is separated by means of a filter (8) from
the recovered catalyst (9).
Description
The present invention concerns a process for removing polychlorobiphenyls
(PCBs) from mineral oils, and especially from dielectric oils contaminated in
electrical equipment.
The problem of decontaminating such mineral oils from the toxic PCBs, that
as known, are not biodegradable has been tackled by means of various methods. In
literature there exist descriptions of chemical treatments with strongly oxidizing
substances (Journal of Am. Chem Soc., 1987, 109, 8081 and Environm. Sci.
Technol., 1988, 22, 1182), with alkaline metals, with metallic sodium, or with
strong nucleophiles (US. Pat. No. 4,327,368; US. Pat. No. 4,353,793; Eur. Pat. No.
397.310; US. Pat. No. 4,663027 and US. Pat. No. 4,748,292), thermodestruction
methods and treatments with ultraviolet radiation,
As regards chemical treatments, it is also known from the prior art, see our
own European patent application No. 95116723.8, that hydrochlorination of the
PCBs with hydrogen or a hydrogen precursor produces a biphenyl as the sole
reaction product (Equation 1):
C12H10-nCln+nH2→Biphenyl + nHCl
The latter compound may to all intents and purposes be considered a
component of the mineral oil.
Furthermore, our previously mentioned patent application envisages that the
hydrodehalogenation of PCBs in mineral oil as solvent should take place in a
multiphase system consisting of an alkaline aqueous solution and a hydrogenation
catalyst whenever there is present also a phase transfer catalyst. It has also been
reported that no reaction will take place when the operation is carried out without
the phase transfer catalyst.
The drawbacks of the processes known from the prior art (with the exclusion
of ultraviolet radiation and hydrodechlorination) consist of the formation of subproducts
that have to be handled in one way or another, the slow reaction speed (for
treatments with superoxide ions and ultraviolet radiation) or the associated
explosion risk (in the case alkaline metal treatments).
We have now found that mineral oils contaminated by PCBs can be
decontaminated even in the absence of the phase transfer catalyst when the
hydrodehalogenation reaction is made to take place at a convenient temperature and
pressure and in the presence of a hydrogenation catalyst.
The said catalyst may be chosen among the families of typical catalysts for
"hydrotreating/hydrogenation/saturation" and "hydrorefining" processes, that is to
say, catalysts that will activate substitution reactions of the more common heteroatoms,
nitrogen, sulphur and oxygen being cases in point, using molecular hydrogen
as the hydrogen source.
The most efficacious of the said catalysts have been found to be Nickel-Molybdenum
(Ni/Mo), Cobalt-Molybdenum, (Co/Mo) and Nickel-Tungsten (Ni/W)
on an alumina support.
The invented process is capable of application to mineral oils contaminated
with PCBs in a wide range of concentrations, preferably between 5 and 50,000 ppm.
It should be noted that when the operations are carried out at low pressures
and temperatures, the reaction speed diminishes in such a manner as to render the
process not particularly suitable for industrial applications.
According to the particular given industrial needs, therefore, the reaction
speed will be raised by operating at higher pressures, preferably between 5 and 50
bar, and at higher temperatures, preferably between 250°C and 400°C.
The principal advantages of the invention consist of:
Further advantages as compared with the previously known methods and
already present in our previous patent application consist of the possibility of
operating on the mineral oil without any preparatory treatment; the complete
absence of any harmful process subproducts; the high reaction speed and the
possibility of re-utilizing the treated mineral oil in an electric transformer after
having duly removed the humidity and gases contained in it.
The invention will now be described in greater detail by reference to three
realization examples and the attached
The initial concentration of the PCBs in the examples here described was in
the range between 730 ppm and 123 ppm.
In the said examples the reactions were carried out in a batch reactor.
The hydrogenation catalyst was Ni/Mo and the temperature was 300° C.
The pressure was between 5 and 45 bar.
Into a batch reactor, indicated by the reference number 1 in Figure 1,
having a nominal volume of 350 ml and provided with a heat exchanger 2 and an
agitator 3 , there were introduced 100 ml of dielectric oil 4 contaminated with 730
ppm of PCBs. The said oil 4 was made to react with gaseous hydrogen 5 at a
pressure of 45 bar and a temperature of 300°C in the presence of 1 g of Ni/Mo
catalyst 6. After being separated by means of a filter 8 from the recovered catalyst
9 , the recovered oil was analyzed in order to determine the residual PCBs.
Following 4 hours of reaction time, gas chromatography analysis with an ECD
detector showed that the degradation yield was 95%. The oil contained a residue of
40 ppm of PCBs.
Into a batch reactor having a nominal volume of 350 ml there were
introduced 100 ml of dielectric oil contaminated with 123 ppm of PCBs and made
to react with gaseous hydrogen at a pressure of 10 bar and a temperature of 300°C
in the presence of 1 g of Ni/Mo catalyst. Following a reaction time of 1 hour, gas
chromatography analysis with an ECD detector showed that the degradation yield
was 95%. The oil contained a residue of 6 ppm of PCBs.
Into a batch reactor having a nominal volume of 350 ml there were
introduced 100 ml of dielectric oil contaminated with 700 ppm of PCBs and made
to react with gaseous hydrogen at a pressure of 5 bar and a temperature of 300°C in
the presence of 1 g of Ni/Mo catalyst. Following a reaction time of 9 hours, gas
chromatography analysis with an ECD detector showed that the degradation yield
was 98%. The oil contained a residue of 11 ppm of PCBs.
It will readily be appreciated that the process can also be realized in a
continuous stirred tank reactor (CSTR), i.e a reactor of the continuous type
ensuring perfect mixing.
Claims (9)
- A process for removing polychlorobiphenyls from mineral oil by means of the hydrodehalogenization reaction, characterized in that the mineral oil containing the polychlorobiphenyls is placed into contact with a hydrogenation catalyst in a reactor and made to react with the said catalyst and a hydrogen source.
- A process in accordance with Claim 1, characterized in that the hydrogenation catalyst is a catalyst belonging to the families of catalysts typical for "hydrotreating/hydrogenation/saturation" and "hydrorefining" processes.
- A process in accordance with Claims 1 and 2, characterized in that the hydrogenation catalyst is Nickel/Molybdenum.
- A process in accordance with Claims 1 and 2, characterized in that the hydrogenation catalyst is Cobalt/Molybdenum.
- A process in accordance with Claims 1 and 2, characterized in that the hydrogenation catalyst is Nickel/Tungsten,
- A process in accordance with Claim 1, characterized in that the hydrogen source is molecular hydrogen.
- A process in accordance with any one of Claims 1 to 6, characterized in that the mineral oils containing polychlorobiphenyls are subjected to a temperature that may vary between 250°C and 400°C and to pressure in the range between 5 and 50 bar.
- A process in accordance with any one of Claims 1 to 7, characterized in that it is applied to mineral oils containing polychlorobiphenyls at concentrations in the range between 5 and 50,000 ppm.
- A process in accordance with Claim 1, characterized in that it is made to take place in a batch reactor or a continuous stirred tank reactor.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI971506 | 1997-06-26 | ||
| IT97MI001506A IT1292420B1 (en) | 1997-06-26 | 1997-06-26 | PROCESS FOR REMOVING POLYCHLOROBIPHENYLS FROM MINERAL OILS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0887087A2 true EP0887087A2 (en) | 1998-12-30 |
| EP0887087A3 EP0887087A3 (en) | 1999-01-20 |
Family
ID=11377439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP98110525A Withdrawn EP0887087A3 (en) | 1997-06-26 | 1998-06-09 | Process for removing polychlorobiphenyls from mineral oils |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0887087A3 (en) |
| IT (1) | IT1292420B1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178001A1 (en) * | 1984-09-14 | 1986-04-16 | Kinetics Technology International B.V. | Process for cleaning of waste materials by refining and/or elimination of biologically Difficult to degrade halogen-, nitrogen- and/or sulfur compounds |
| DE3623430A1 (en) * | 1986-07-11 | 1988-01-28 | Veba Oel Entwicklungs Gmbh | METHOD FOR HYDROGENATING TREATMENT WITH CHLORBIPHENYLENE AND THE LIKE CONTAMINATED MINERAL OILS |
| EP0299149A2 (en) * | 1987-07-17 | 1989-01-18 | Ruhrkohle Aktiengesellschaft | Process for working up used lubricants by hydrogenation |
| US5316663A (en) * | 1992-01-13 | 1994-05-31 | Uop | Process for the treatment of halogenated hydrocarbons |
-
1997
- 1997-06-26 IT IT97MI001506A patent/IT1292420B1/en active IP Right Grant
-
1998
- 1998-06-09 EP EP98110525A patent/EP0887087A3/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178001A1 (en) * | 1984-09-14 | 1986-04-16 | Kinetics Technology International B.V. | Process for cleaning of waste materials by refining and/or elimination of biologically Difficult to degrade halogen-, nitrogen- and/or sulfur compounds |
| DE3623430A1 (en) * | 1986-07-11 | 1988-01-28 | Veba Oel Entwicklungs Gmbh | METHOD FOR HYDROGENATING TREATMENT WITH CHLORBIPHENYLENE AND THE LIKE CONTAMINATED MINERAL OILS |
| EP0299149A2 (en) * | 1987-07-17 | 1989-01-18 | Ruhrkohle Aktiengesellschaft | Process for working up used lubricants by hydrogenation |
| US5316663A (en) * | 1992-01-13 | 1994-05-31 | Uop | Process for the treatment of halogenated hydrocarbons |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1292420B1 (en) | 1999-02-08 |
| EP0887087A3 (en) | 1999-01-20 |
| ITMI971506A0 (en) | 1997-06-26 |
| ITMI971506A1 (en) | 1998-12-26 |
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