CA2127242C - Extraction de contaminants organiques toxiques a partir du bois - Google Patents

Extraction de contaminants organiques toxiques a partir du bois Download PDF

Info

Publication number: CA2127242C
Authority: CA; Canada
Prior art keywords: wood; process according; extraction; pentachlorophenol; contaminants
Prior art date: 1994-06-30
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.): Expired - Lifetime

Application number

CA002127242A

Other languages

English (en)

Other versions

CA2127242A1 (fr

Inventor

John N.R. Ruddick

Futong Cui

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bell Canada Inc

Original Assignee

Bell Canada Inc

Priority date (The priority date 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 date listed.)

1994-06-30

Filing date

1994-06-30

Publication date

2006-12-19

1994-06-30 Application filed by Bell Canada Inc filed Critical Bell Canada Inc

1994-06-30 Priority to CA002479571A priority Critical patent/CA2479571C/fr

1994-06-30 Priority to CA002127242A priority patent/CA2127242C/fr

1995-12-31 Publication of CA2127242A1 publication Critical patent/CA2127242A1/fr

2006-12-19 Application granted granted Critical

2006-12-19 Publication of CA2127242C publication Critical patent/CA2127242C/fr

2014-06-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000605 extraction Methods 0.000 title claims abstract description 84
239000002023 wood Substances 0.000 title claims abstract description 59
239000000356 contaminant Substances 0.000 title claims abstract description 35
231100000331 toxic Toxicity 0.000 title claims abstract description 29
230000002588 toxic effect Effects 0.000 title claims abstract description 29
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims abstract description 182
238000000034 method Methods 0.000 claims abstract description 73
230000008569 process Effects 0.000 claims abstract description 55
238000000194 supercritical-fluid extraction Methods 0.000 claims abstract description 41
239000012530 fluid Substances 0.000 claims abstract description 33
150000004826 dibenzofurans Chemical class 0.000 claims abstract description 25
150000004827 dibenzo-1,4-dioxins Chemical class 0.000 claims abstract description 20
239000003504 photosensitizing agent Substances 0.000 claims abstract description 15
239000003795 chemical substances by application Substances 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000002002 slurry Substances 0.000 claims abstract description 7
230000002522 swelling effect Effects 0.000 claims abstract description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 74
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
239000001569 carbon dioxide Substances 0.000 claims description 37
229910002092 carbon dioxide Inorganic materials 0.000 claims description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
239000002904 solvent Substances 0.000 claims description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
229910001868 water Inorganic materials 0.000 claims description 28
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
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KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 claims description 12
238000001782 photodegradation Methods 0.000 claims description 12
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229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
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235000003270 potassium fluoride Nutrition 0.000 claims description 4
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
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IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 2
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FOIBFBMSLDGNHL-UHFFFAOYSA-N 1,2,3,4,6,7,8,9-Octachlorodibenzo-p-dioxin Chemical compound ClC1=C(Cl)C(Cl)=C2OC3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3OC2=C1Cl FOIBFBMSLDGNHL-UHFFFAOYSA-N 0.000 description 9
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KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 7
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WCLNVRQZUKYVAI-UHFFFAOYSA-N 1,2,3,4,6,7,8-Heptachlorodibenzodioxin Chemical compound O1C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2OC2=C1C=C(Cl)C(Cl)=C2Cl WCLNVRQZUKYVAI-UHFFFAOYSA-N 0.000 description 6
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000006184 cosolvent Substances 0.000 description 4
150000002013 dioxins Chemical class 0.000 description 4
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
230000014759 maintenance of location Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
244000005700 microbiome Species 0.000 description 4
239000001294 propane Substances 0.000 description 4
WDMKCPIVJOGHBF-UHFFFAOYSA-N 1,2,3,4,6,7,8-Heptachlorodibenzofuran Chemical compound ClC1=C(Cl)C(Cl)=C2C(C=C(C(=C3Cl)Cl)Cl)=C3OC2=C1Cl WDMKCPIVJOGHBF-UHFFFAOYSA-N 0.000 description 3
NLBQVWJHLWAFGJ-UHFFFAOYSA-N 1,2,3,4,6,7-hexachlorodibenzo-p-dioxin Chemical compound ClC1=C(Cl)C(Cl)=C2OC3=C(Cl)C(Cl)=CC=C3OC2=C1Cl NLBQVWJHLWAFGJ-UHFFFAOYSA-N 0.000 description 3
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KSMVNVHUTQZITP-UHFFFAOYSA-N 2,3,7,8-Tetrachlorodibenzofuran Chemical compound O1C2=CC(Cl)=C(Cl)C=C2C2=C1C=C(Cl)C(Cl)=C2 KSMVNVHUTQZITP-UHFFFAOYSA-N 0.000 description 1
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical class OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical class OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
GQKDZDYQXPOXEM-UHFFFAOYSA-N 3-chlorocatechol Chemical compound OC1=CC=CC(Cl)=C1O GQKDZDYQXPOXEM-UHFFFAOYSA-N 0.000 description 1
JDQDSEVNMTYMOC-UHFFFAOYSA-N 3-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1 JDQDSEVNMTYMOC-UHFFFAOYSA-N 0.000 description 1
HGCFMGDVMNCLNU-UHFFFAOYSA-N 3-thiophen-2-ylsulfonylpyrazine-2-carbonitrile Chemical compound N=1C=CN=C(C#N)C=1S(=O)(=O)C1=CC=CS1 HGCFMGDVMNCLNU-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
208000001348 Chloracne Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
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
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
108010029541 Laccase Proteins 0.000 description 1
108010054320 Lignin peroxidase Proteins 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
102000003992 Peroxidases Human genes 0.000 description 1
241000222393 Phanerochaete chrysosporium Species 0.000 description 1
244000019397 Pinus jeffreyi Species 0.000 description 1
235000013267 Pinus ponderosa Nutrition 0.000 description 1
235000013269 Pinus ponderosa var ponderosa Nutrition 0.000 description 1
235000013268 Pinus ponderosa var scopulorum Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000779819 Syncarpia glomulifera Species 0.000 description 1
DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000001273 butane Substances 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
238000005202 decontamination Methods 0.000 description 1
230000003588 decontaminative effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000007862 dimeric product Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 1
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000005264 electron capture Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000005357 flat glass Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 1
VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
235000020664 gamma-linolenic acid Nutrition 0.000 description 1
229960002733 gamolenic acid Drugs 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000002655 kraft paper Substances 0.000 description 1
238000009533 lab test Methods 0.000 description 1
238000011005 laboratory method Methods 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000003913 materials processing Methods 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
108040007629 peroxidase activity proteins Proteins 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
OZPGBBYMZZTDMV-UHFFFAOYSA-N propane;tetrachloromethane Chemical compound CCC.ClC(Cl)(Cl)Cl OZPGBBYMZZTDMV-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000006042 reductive dechlorination reaction Methods 0.000 description 1
238000005067 remediation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
239000010891 toxic waste Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
239000007861 trimeric product Substances 0.000 description 1
229940036248 turpentine Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000003171 wood protecting agent Substances 0.000 description 1
238000004876 x-ray fluorescence Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
- C07C39/27—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms all halogen atoms being bound to ring carbon atoms
- C07C39/36—Pentachlorophenol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Toxicology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Business, Economics & Management (AREA)
Emergency Management (AREA)
Extraction Or Liquid Replacement (AREA)
Treatment Of Water By Oxidation Or Reduction (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002127242A 1994-06-30 1994-06-30 Extraction de contaminants organiques toxiques a partir du bois Expired - Lifetime CA2127242C (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA002479571A CA2479571C (fr)	1994-06-30	1994-06-30	Extraction de contaminants organiques toxiques
CA002127242A CA2127242C (fr)	1994-06-30	1994-06-30	Extraction de contaminants organiques toxiques a partir du bois

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002127242A CA2127242C (fr)	1994-06-30	1994-06-30	Extraction de contaminants organiques toxiques a partir du bois

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002479571A Division CA2479571C (fr)	1994-06-30	1994-06-30	Extraction de contaminants organiques toxiques

Publications (2)

Publication Number	Publication Date
CA2127242A1 CA2127242A1 (fr)	1995-12-31
CA2127242C true CA2127242C (fr)	2006-12-19

Family

ID=4153940

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA002479571A Expired - Lifetime CA2479571C (fr)	1994-06-30	1994-06-30	Extraction de contaminants organiques toxiques
CA002127242A Expired - Lifetime CA2127242C (fr)	1994-06-30	1994-06-30	Extraction de contaminants organiques toxiques a partir du bois

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA002479571A Expired - Lifetime CA2479571C (fr)	1994-06-30	1994-06-30	Extraction de contaminants organiques toxiques

Country Status (1)

Country	Link
CA (2)	CA2479571C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119979205B (zh) *	2025-04-14	2025-06-17	湖南工程学院	一种从煤焦油中分段提取酚类化合物的方法

1994
- 1994-06-30 CA CA002479571A patent/CA2479571C/fr not_active Expired - Lifetime
- 1994-06-30 CA CA002127242A patent/CA2127242C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2127242A1 (fr)	1995-12-31
CA2479571A1 (fr)	1995-12-31
CA2479571C (fr)	2006-08-01

Legal Events

Date	Code	Title	Description
2001-04-11	EEER	Examination request
2014-09-01	MKEX	Expiry	Effective date: 20140630

Publication	Publication Date	Title
US5698829A (en)	1997-12-16	Photodegradation of toxic contaminants
US5075017A (en)	1991-12-24	Method for removing polychlorinated dibenzodioxins and polychlorinated dibenzofurans from paper mill sludge
Qu et al.	2022	Free radicals-triggered reductive and oxidative degradation of highly chlorinated compounds via regulation of heat-activated persulfate by low-molecular-weight organic acids
Anku et al.	2017	Phenolic compounds in water: sources, reactivity, toxicity and treatment methods
Lo Scalzo et al.	1994	Olea europaea chemicals repellent to Dacus oleae females
Pramauro et al.	1998	Photocatalytic degradation of naphthalene in aqueous TiO2 dispersions: effect of nonionic surfactants
Taylor Jr et al.	1999	Dissolved organic matter inhibition of sonochemical degradation of aqueous polycyclic aromatic hydrocarbons
Narkis et al.	1980	Ozone-induced biodegradability of a non-ionic surfactant
JPH11292799A (ja)	1999-10-26	超臨界水処理による芳香族化合物の製造方法
Corless et al.	1990	Ozonation of pyrene in aqueous solution
CA2006825C (fr)	1995-12-12	Methode de deshalogenation d'un produit contamine
CA2127242C (fr)	2006-12-19	Extraction de contaminants organiques toxiques a partir du bois
Hessler et al.	1996	Quenching of singlet oxygen (1Δg) by humic substances
Schynowski et al.	1996	Photochemistry of parathion on plant surfaces: relationship between photodecomposition and iodine number of the plant cuticle
US5552059A (en)	1996-09-03	Process to decontaminate soil containing chlorophenols
Yuliani et al.	2019	UV-induced colour generation of pulp and paper mill effluents as a proxy of ligno-cellulosic biorefinery wastewater
Abd Latif et al.	2021	Pineapple leaves based activated carbon for efficient removal of reactive black 5 in aqueous
Chen et al.	2023	Alkali-catalyzed hydrothermal oxidation treatment of triclosan in soil: Mechanism, degradation pathway and toxicity evaluation
Xu et al.	2023	Reactive oxygen species induced by plant essential oil for effective degradation of p-phenylenediamine
Wang et al.	2004	Dechlorination and decolorization of chloro-organics in pulp bleach plant E-1 effluents by advanced oxidation processes
Gelover et al.	2000	Catalytic photodegradation of alkyl surfactants
US7365236B2 (en)	2008-04-29	Generation of a creosote-like mixture, or recovery of metals, or both from preserved wood by reaction in supercritical water
Sun et al.	2016	Laccase-catalyzed oxidative coupling reaction of triclosan in aqueous solution
US5009745A (en)	1991-04-23	Method for removing polychlorinated dibenzodioxins and polychlorinated dibenzofurans from secondary fibers using supercritical CO2 extraction
Catallo et al.	2004	Hydrothermal treatment of CCA-and penta-treated wood