EP0635283A1 - Procédé pour la déshalogénation réductive des matériaux solides et liquides contenant des composés organiques halogénés - Google Patents

Procédé pour la déshalogénation réductive des matériaux solides et liquides contenant des composés organiques halogénés Download PDF

Info

Publication number: EP0635283A1
Authority: EP; European Patent Office
Prior art keywords: sodium; solid; ammonia; minutes; carried out
Prior art date: 1993-07-24
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.): Granted

Application number

EP94250184A

Other languages

German (de)

English (en)

Other versions

EP0635283B1 (fr

Inventor

Frank-Dieter Kopinke

Matthias Remmler

Ulrich Stottmeister

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.)

Helmholtz Zentrum fuer Umweltforschung GmbH UFZ

Original Assignee

Helmholtz Zentrum fuer Umweltforschung GmbH UFZ

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.)

1993-07-24

Filing date

1994-07-20

Publication date

1995-01-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6493654&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0635283(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1994-07-20 Application filed by Helmholtz Zentrum fuer Umweltforschung GmbH UFZ filed Critical Helmholtz Zentrum fuer Umweltforschung GmbH UFZ

1995-01-25 Publication of EP0635283A1 publication Critical patent/EP0635283A1/fr

1999-01-20 Application granted granted Critical

1999-01-20 Publication of EP0635283B1 publication Critical patent/EP0635283B1/fr

2014-07-20 Anticipated expiration legal-status Critical

Status Revoked legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 15
238000005695 dehalogenation reaction Methods 0.000 title claims abstract description 11
230000002829 reductive effect Effects 0.000 title claims abstract description 5
239000011344 liquid material Substances 0.000 title 1
239000011343 solid material Substances 0.000 title 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 30
239000011734 sodium Substances 0.000 claims abstract description 29
229910052708 sodium Inorganic materials 0.000 claims abstract description 29
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 claims abstract description 28
239000007787 solid Substances 0.000 claims abstract description 21
150000008282 halocarbons Chemical class 0.000 claims abstract description 7
239000007788 liquid Substances 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims abstract description 4
239000000126 substance Substances 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 12
229910021529 ammonia Inorganic materials 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 4
238000000354 decomposition reaction Methods 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 2
230000002040 relaxant effect Effects 0.000 claims description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
235000011114 ammonium hydroxide Nutrition 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
238000000605 extraction Methods 0.000 abstract description 3
239000013049 sediment Substances 0.000 abstract description 2
239000002689 soil Substances 0.000 abstract 1
239000002699 waste material Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
-1 hydrogen halides Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
GKEUODMJRFDLJY-UHFFFAOYSA-N 1-Methylfluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2C GKEUODMJRFDLJY-UHFFFAOYSA-N 0.000 description 1
JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
IUYHQGMDSZOPDZ-UHFFFAOYSA-N 2,3,4-trichlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 IUYHQGMDSZOPDZ-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000047875 Pica hudsonia Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000000571 coke Substances 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
230000006837 decompression Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000010881 fly ash Substances 0.000 description 1
JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229960002809 lindane Drugs 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000010808 liquid waste Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000010327 methods by industry Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000006491 negative regulation of transport Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005406 washing Methods 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
- 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
- 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
- A62D3/34—Dehalogenation using reactive chemical agents able to degrade
- 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
- 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
- A62D2203/00—Aspects of processes for making harmful chemical substances harmless, or less harmful, by effecting chemical change in the substances
- A62D2203/04—Combined processes involving two or more non-distinct steps covered by groups A62D3/10 - A62D3/40

Definitions

the invention relates to a chemical process for the dehalogenation of halogenated hydrocarbons which are contained in mixtures of solid or liquid substances.
Waste or by-products of industrial processes which contain organically bound halogens (fluorine, chlorine, bromine, iodine as organohalogens or halogenated hydrocarbons) represent a considerable risk potential because of their ecotoxic properties. Numerous processes are known for their destruction and z. T. technically tested (see G. Dehoust, Ch. Ewen, R. Gensicke: waste factory, shown using the example of the disposal of organic halogen waste, waste and refuse 1991 (5), 283-294).
Lissel and Fründ provide a current overview of available non-thermal processes ⁇ M. Lissel, M. Fründ, Labor 2000, 1991, 205 - 208Ü. After the Degussa sodium process DE-PS 28 13 200 C2 (1978), US Pat. 4 255 252 (1979) Sodium as a suspension (average 20 particle diameter below 100 ⁇ m, preferably below 30 ⁇ m) in oil at elevated temperatures (90-160 ° C) reacted with pretreated waste oils.
An advantage of this sodium process is its selectivity. In contrast to oxidative degradation and catalytic hydrogenation, hydrocarbons are not affected. Because of its high reactivity, sodium can cause complete dehalogenation even at low temperatures and short reaction times, provided that there is no transport limitation in the reaction medium.
the technical implementation of the sodium process requires a comparatively low investment and is therefore particularly suitable for smaller, possibly mobile systems.
An obvious disadvantage of using metal suspensions is that solid products cannot be easily treated with them because solid-solid reactions have a high inhibition of transport. It is precisely this application which is of interest for the treatment of solids such as loaded activated carbons and cokes, filter dusts and others in which there are low concentrations of more or less bound hydrogen halides on a solid matrix.
the invention solves the problem of making halogenated hydrocarbons, which are sorbed on solid matrices, available for direct dehalogenation with sodium without the need for an additional extraction step.
the contaminated solid is arranged in a fixed bed and a sodium solution in ammonia flows through it.
the treatment can be carried out at temperatures near the boiling point of ammonia under atmospheric pressure or at temperatures near ambient temperature under elevated pressure or under conditions between these corner points.
solvent ammonia can either be removed as a liquid phase from the purified solid or evaporated directly.
the evaporation is achieved depending on the reaction conditions by heating and / or relaxing. In any case, the ammonia is circulated.
Reaction temperatures above 30 ° C only make sense if this is to cause additional effects on the solid matrix (e.g. extraction of further pollutants).
the processing of the reaction products depends on the chosen embodiment and the waste product to be cleaned. It contains the following steps, which can be combined in different ways: (i) decomposition of excess sodium by adding water or other reagents with active hydrogen (e.g. methanol, acetic acid, dilute mineral acids or the like); (ii) evaporation of the solvent by heating or decompression, the evaporated ammonia being recycled after liquefaction; (iii) washing and neutralizing the cleaned solid or wash water, if necessary.
active hydrogen e.g. methanol, acetic acid, dilute mineral acids or the like

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)
Fire-Extinguishing Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Extraction Or Liquid Replacement (AREA)

EP94250184A 1993-07-24 1994-07-20 Procédé pour la déshalogénation réductive des matériaux solides contenant des composés organiques halogénés Revoked EP0635283B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4324931A DE4324931A1 (de)	1993-07-24	1993-07-24	Verfahren zur reduktiven Dehalogenierung von organohalogenhaltigen festen und flüssigen Stoffen
DE4324931		1993-07-24

Publications (2)

Publication Number	Publication Date
EP0635283A1 true EP0635283A1 (fr)	1995-01-25
EP0635283B1 EP0635283B1 (fr)	1999-01-20

Family

ID=6493654

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP94250184A Revoked EP0635283B1 (fr)	1993-07-24	1994-07-20	Procédé pour la déshalogénation réductive des matériaux solides contenant des composés organiques halogénés

Country Status (3)

Country	Link
EP (1)	EP0635283B1 (fr)
AT (1)	ATE175882T1 (fr)
DE (2)	DE4324931A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0880378A4 (fr) *	1995-11-07	1999-03-24	Commodore Applied Technologies	Procede et equipement de destruction d'agents de guerre chimique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2003230638A (ja) *	2002-02-07	2003-08-19	Toshiba Corp	有害有機塩素化合物の無害化処理システムおよび無害化処理された生成物と廃棄物のリサイクル方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2017143A (en) *	1978-03-25	1979-10-03	Degussa	Process for regenerating spent lubricating oils
EP0288408A1 (fr) *	1987-03-30	1988-10-26	A.L. Sandpiper Corporation	Procédé pour la décontimination de substrats pollués
US4910353A (en) *	1983-02-07	1990-03-20	Transformer Service, Inc.	Dehalogenation of polychlorinated biphenyls and other related compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2249679C3 (de) *	1972-10-11	1980-09-11	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von 9cis Tricosen, Muscalure
CH668709A5 (de) *	1985-12-06	1989-01-31	Ciba Geigy Ag	Verfahren zur enthalogenierung von polyhalogenierten aliphatischen und aromatischen verbindungen.

1993
- 1993-07-24 DE DE4324931A patent/DE4324931A1/de not_active Withdrawn
1994
- 1994-07-20 AT AT94250184T patent/ATE175882T1/de active
- 1994-07-20 EP EP94250184A patent/EP0635283B1/fr not_active Revoked
- 1994-07-20 DE DE59407681T patent/DE59407681D1/de not_active Expired - Fee Related

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2017143A (en) *	1978-03-25	1979-10-03	Degussa	Process for regenerating spent lubricating oils
US4910353A (en) *	1983-02-07	1990-03-20	Transformer Service, Inc.	Dehalogenation of polychlorinated biphenyls and other related compounds
EP0288408A1 (fr) *	1987-03-30	1988-10-26	A.L. Sandpiper Corporation	Procédé pour la décontimination de substrats pollués

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 76, no. 13, 27 March 1972, Columbus, Ohio, US; abstract no. 69170s, M.V.KENNEDY ET AL: "Chemical and Thermal Aspects of Pesticide Disposal" page 115; column 2; *
CHEMICAL ABSTRACTS, vol. 83, no. 14, 6 October 1975, Columbus, Ohio, US; abstract no. 125874h, E.S.LAHANIATAS ET AL: "Ecological chemistry. XCIV. Analysis and photochemistry of high-boiling polychlorinated paraffin mixtures" page 805; column 1; *
J.DE LANNOY ET AL: "Sodium-Ammonia Reductions in N-Heteroaromatic Chemistry.", BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. 79, 1970, OXFORD GB, pages 329 - 336 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0880378A4 (fr) *	1995-11-07	1999-03-24	Commodore Applied Technologies	Procede et equipement de destruction d'agents de guerre chimique
US5998691A (en) *	1995-11-07	1999-12-07	Commodore Applied Technologies, Inc.	Method and apparatus to destroy chemical warfare agents

Also Published As

Publication number	Publication date
ATE175882T1 (de)	1999-02-15
DE59407681D1 (de)	1999-03-04
DE4324931A1 (de)	1995-01-26
EP0635283B1 (fr)	1999-01-20

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