US20010005766A1 - Compositions based on dimethyl disulphide with a masked smell - Google Patents

Compositions based on dimethyl disulphide with a masked smell Download PDF

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Publication number
US20010005766A1
US20010005766A1 US09/350,994 US35099499A US2001005766A1 US 20010005766 A1 US20010005766 A1 US 20010005766A1 US 35099499 A US35099499 A US 35099499A US 2001005766 A1 US2001005766 A1 US 2001005766A1
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Prior art keywords
dmds
ppm
composition according
smell
phthalate
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Abandoned
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US09/350,994
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English (en)
Inventor
Georges Fremy
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Arkema France SA
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Elf Atochem SA
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Application filed by Elf Atochem SA filed Critical Elf Atochem SA
Assigned to ELF ATOCHEM S.A. reassignment ELF ATOCHEM S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FREMY, GEORGES
Publication of US20010005766A1 publication Critical patent/US20010005766A1/en
Priority to US10/043,281 priority Critical patent/US6639110B2/en
Priority to US10/043,282 priority patent/US6743951B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/26—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton

Definitions

  • the present invention relates to the field of organic sulphides and more particularly that of dimethyl disulphide.
  • DMDS Dimethyl disulphide
  • DMDS has a strong and aggressive smell due in part to the presence of highly odorous impurities and in part to the garlicky and ethereal smell intrinsic to DMDS. This strong smell hinders the increased growth of this product in applications such as the sulphurization of catalysts or as loading additive for steam cracking.
  • DMDS exhibits numerous advantages, in particular a high sulphur content (68%) and non-coking degradation products (CH 4 , H 2 S).
  • CH 4 , H 2 S non-coking degradation products
  • DMDS results in generally superior performances to other products, such as tert-alkyl polysulphides.
  • these other products have markedly lower odorous levels which, for this reason, make them easier to handle in comparison with DMDS.
  • a particularly efficient and economical method, among the methods for the synthesis of DMDS, is the oxidation of methyl mercaptan by sulphur according to the reaction:
  • U.S. Pat. No. 5,559,271 recommends adding a certain amount of masking product to them, such as, in particular, vanillin or ethyl vanillin.
  • a certain amount of masking product such as, in particular, vanillin or ethyl vanillin.
  • vanillin or ethyl vanillin.
  • this patent is more particularly targeted at the treatment of heavy polysulphides, such as, for example, di-t-nonyl pentasulphide.
  • the application of this method to DMDS does not allow its nauseating and highly unpleasant smell to be masked.
  • R 1 represents an optionally unsaturated, linear or branched hydrocarbon-comprising radical comprising from 1 to 4 carbon atoms
  • R 2 represents an optionally unsaturated, linear, branched or cyclic hydrocarbon-comprising radical comprising from 2 to 8 carbon atoms.
  • the subject-matter of the invention is therefore a DMDS-based composition, characterized in that it comprises, by weight, at least 95% of dimethyl disulphide, less than 500 ppm of methyl mercaptan (MM), less than 100 ppm of dimethyl sulphide (DMS) and up to 1% of at least one odour-masking agent, preferably an ester of general formula (I).
  • MM methyl mercaptan
  • DMS dimethyl sulphide
  • I odour-masking agent
  • any method known to a person skilled in the art for producing a DMDS with reduced contents of volatile impurities, such as MM and DMS, can be used in the context of the present invention.
  • a particularly preferred method consists of a distillative topping. This method exhibits the advantage of jointly removing MM and DMS, whereas the usual methods for smell reduction, generally based on removing residual mercaptans by specific reaction of a mercaptan functional group with a removal agent, such as a base or an alkene oxide in the presence of a base, are without effect on DMS present in DMDS.
  • the DMDS thus topped, which preferably comprises less than 200 ppm of MM and less than 50 ppm of DMS, is used to prepare a composition according to the invention by simple addition of at least one odour-masking agent.
  • odour-masking agent(s) As one of the main advantages of DMDS in its applications is its high sulphur content (68%), an excessively high content of odour-masking agent in the composition would result in this sulphur assay being lowered and would decrease the advantage of this product in its main applications.
  • the maximum content of odour-masking agent(s) is therefore set at 1% but this content is preferably between 0.1 and 0.5% and more particularly equal to approximately 0.2%.
  • esters of general formula (I) of butyl acetate, isoamyl acetate, benzyl acetate, ethyl butyrate, propyl butyrate, butyl butyrate, 2-methylbutyl butyrate or isoamyl butyrate. Isoamyl acetate, 2-methylbutyl butyrate, isoamyl butyrate, benzyl acetate and the mixtures of these compounds are more particularly preferred.
  • the esters (I) may or may not be used in combination with ortho-phthalates corresponding to the general formula:
  • R 3 and R 4 which are identical or different, each represent an optionally unsaturated, linear, branched or cyclic hydrocarbon-comprising radical comprising from 1 to 8 carbon atoms. Mention may more particularly be made, as non-limiting example of compound (II), of diethyl ortho-phthalate.
  • a typical composition of the present invention comprises, by weight: isoamyl acetate 0.1% diethyl ortho-phthalate 0.1% topped DMDS 99.8%
  • Another typical composition of the present invention comprises, by weight: isoamyl acetate 0.05% 2-methylbutyl butyrate 0.03% benzyl acetate 0.02% diethyl ortho-phthalate 0.1% topped DMDS 99.8%
  • FIG. 1 is a diagram of the plant used, combining two reactors (primary reactor 1 and finishing reactor 3 ).
  • the primary reactor is a stirred reactor and the finishing reactor is a stationary-bed tubular reactor.
  • a degassing system is positioned between these two reactors, this system being composed of a jacketed receptacle 2 equipped with a stirrer and surmounted by a cooled column which allows the methyl mercaptan, which can be carried away with the hydrogen sulphide, to be recondensed before being removed.
  • This plant is completed by a pump, placed between the outlet of the degasser 2 and the inlet of the finishing reactor 3 , which makes it possible to feed this reactor with liquid product treated in the degasser.
  • a degassing column 4 serves to completely remove H 2 S dissolved in the liquid exiting from the reactor 3 .
  • a distillation column 5 makes it possible to separate most of the excess methyl mercaptan for the purpose of recycling it via the pipe 22 to the reactor 1 .
  • the column 6 makes it possible to separate the residual dimethyl polysulphides (DMPS) for the purpose of recycling them in the reactor 3 or the reactor 1 .
  • DMPS dimethyl polysulphides
  • This reaction mixture is then conveyed into the degasser 2 via the pipe 14 in order to be treated.
  • the mixture freed from H 2 S, is conveyed via the pipe 17 into the finishing reactor 3 , which contains a charge of 94 g of dry A21 resin.
  • the pressure in the reactor is 5.5 bar relative and the temperature 40° C.
  • the mixture has the following composition by weight, excluding H 2 S and excluding excess methyl mercaptan: DMDS 98.5%, DMPS 1.5%.
  • the mixture is then introduced via the pipe 18 into the degasser 4 , in order to remove the H 2 S which has formed in the reactor 3 during the retrogression of the dimethyl polysulphides by methyl mercaptan to give DMDS.
  • the mixture is introduced via the pipe 21 into the first distillation column 5 , in order to remove virtually all the excess methyl mercaptan.
  • This methyl mercaptan can be recycled via the pipe 22 to the introduction of the reactants into the reactor 1 .
  • the mixture is conveyed via the pipe 23 into the second distillation column 6 , where the DMPSs are removed at the column bottom via the pipe 25 , in order optionally to be recycled in the reactor 3 , or via the pipe 26 , in order optionally to be recycled in the reactor 1 .
  • the DMDS finally collected at the top of the column 6 via the pipe 24 and known as A o for the olfactory tests described in the following examples, has the following composition by weight: DMDS 99.3% DMPS 3000 ppm MM 4000 ppm DMS 300 ppm
  • the synthetic procedure is the same as that described in Example 1, except that the DMDS exiting from the column 6 via the pipe 24 is introduced into a third distillation column 7 (see diagram in the appended FIG. 2), where the volatile impurities, such as methyl mercaptan and dimethyl sulphide, are removed at the column top via the pipe 27 .
  • the DMDS collected at the column bottom via the pipe 28 has the following composition by weight: DMDS 99.7% DMPS 3000 ppm MM ⁇ 100 ppm DMS ⁇ 50 ppm
  • This purified DMDS hereinafter known as B o
  • a DMDS sample A o prepared in Example 1 were subjected to an olfactory test.
  • the 8 people invited to this test unanimously recognized a marked improvement in the smell of the B o DMDS in comparison with the A o DMDS but everyone also reported that a garlicky and ethereal smell remained in the B o DMDS.
  • Example 3 The vanillin used in Example 3 was replaced by 2000 ppm of ethyl vanillin (3-ethoxy-4-hydroxybenzaldehyde). Its dissolution was observed after one hour at 25° C. The resulting sample was known as B 2 .
  • Examples 5 and 6 illustrate the preparation of DMDS-based compositions with the smell masked by the preferred products of the present invention.
  • Example 5 The mixture used in Example 5 was replaced by 2000 ppm of a mixture having the following composition by weight: isoamyl acetate 25% diethyl ortho-phthalate 50% 2-methylbutyl butyrate 15% benzyl acetate 10%
  • the samples B o , B 1 , B 2 , B 3 and B 4 were subjected to a comparative olfactory test carried out by the panel of 8 people mentioned in Example 2. It was asked of these 8 people to attribute to the samples a note ranging from 0 to 5 according to their preference with respect to the smell, the note 0 being attributed to the least preferred smell, the note 5 to the most preferred smell and the notes 1 , 2 , 3 and 4 allowing them to classify the intermediate levels.
  • Comparative Examples 7 to 11 illustrate the need to remove most of the volatile impurities from the DMDS in order to observe a significant odour-masking effect.
  • Example 3 was repeated (masking agent: vanillin) but replacing 100 g of B o DMDS with 100 g of the non-topped DMDS A o prepared in Example 1. The resulting sample was known as A 1 .
  • the 8 members of the panel compared the smell of A 1 with that of B o and everyone preferred the smell of B o (DMDS purified of its volatile impurities and without masking agent) to that of the composition A 1 based on unpurified DMDS and on vanillin.
  • Example 7 The procedure of Example 7 was followed, vanillin being replaced by ethyl vanillin.
  • the 8 people of the panel preferred the smell of the sample B o to that of the resulting sample (A 2 ).
  • Example 7 The procedure of Example 7 was followed, vanillin being replaced by menthol. The smell of the sample B o was still preferred to that of the resulting sample (A 3 ).
  • Example 7 The procedure of Example 7 was followed, vanillin being replaced by the mixture of masking products mentioned in Example 5. The resulting sample was known as A 4 .
  • the 8 people of the panel preferred the smell of B o to that of A 4 .
  • Example 7 The procedure of Example 7 was followed, vanillin being replaced by the mixture of masking products mentioned in Example 6.
  • the resulting sample was known as A 5 .
  • the smell of the sample B o was still preferred to that of the sample A 5 .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)
  • Exhaust Gas Treatment By Means Of Catalyst (AREA)
US09/350,994 1998-07-31 1999-07-12 Compositions based on dimethyl disulphide with a masked smell Abandoned US20010005766A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/043,281 US6639110B2 (en) 1998-07-31 2002-01-14 Method for making dimethyl disulphide compositions having a masked smell
US10/043,282 US6743951B2 (en) 1998-07-31 2002-01-14 Compositions based on dimethyl disulphide with a masked smell

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR98/09864 1998-07-31
FR9809864A FR2781795B1 (fr) 1998-07-31 1998-07-31 Compositions a base de dimethyldisulfure a odeur masquee

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US10/043,282 Continuation US6743951B2 (en) 1998-07-31 2002-01-14 Compositions based on dimethyl disulphide with a masked smell
US10/043,281 Division US6639110B2 (en) 1998-07-31 2002-01-14 Method for making dimethyl disulphide compositions having a masked smell

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US10/043,281 Expired - Lifetime US6639110B2 (en) 1998-07-31 2002-01-14 Method for making dimethyl disulphide compositions having a masked smell
US10/043,282 Expired - Lifetime US6743951B2 (en) 1998-07-31 2002-01-14 Compositions based on dimethyl disulphide with a masked smell

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US10/043,282 Expired - Lifetime US6743951B2 (en) 1998-07-31 2002-01-14 Compositions based on dimethyl disulphide with a masked smell

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US (3) US20010005766A1 (es)
EP (1) EP0976726B1 (es)
JP (1) JP4394201B2 (es)
KR (1) KR100609276B1 (es)
CN (1) CN1160325C (es)
AR (1) AR024507A1 (es)
AT (1) ATE241597T1 (es)
AU (1) AU764075B2 (es)
BR (1) BR9902938B1 (es)
CA (1) CA2277895C (es)
CO (1) CO5231229A1 (es)
DE (1) DE69908252T2 (es)
DK (1) DK0976726T3 (es)
EG (1) EG22544A (es)
ES (1) ES2200481T3 (es)
FR (1) FR2781795B1 (es)
GC (1) GC0000106A (es)
HU (1) HU224221B1 (es)
ID (1) ID23475A (es)
MY (1) MY121424A (es)
NO (1) NO313669B1 (es)
NZ (1) NZ336950A (es)
PL (1) PL191732B1 (es)
PT (1) PT976726E (es)
RO (1) RO120406B1 (es)
RU (1) RU2219168C2 (es)
SG (1) SG93838A1 (es)
SK (1) SK283797B6 (es)
TR (1) TR199901835A3 (es)
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Cited By (9)

* Cited by examiner, † Cited by third party
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US20090312273A1 (en) * 2005-09-12 2009-12-17 Abela Pharmaceuticals, Inc. Compositions compromising Dimethyl Sulfoxide (DMSO)
US7955418B2 (en) 2005-09-12 2011-06-07 Abela Pharmaceuticals, Inc. Systems for removing dimethyl sulfoxide (DMSO) or related compounds or odors associated with same
US8435224B2 (en) 2005-09-12 2013-05-07 Abela Pharmaceuticals, Inc. Materials for facilitating administration of dimethyl sulfoxide (DMSO) and related compounds
US8480797B2 (en) 2005-09-12 2013-07-09 Abela Pharmaceuticals, Inc. Activated carbon systems for facilitating use of dimethyl sulfoxide (DMSO) by removal of same, related compounds, or associated odors
US8673061B2 (en) 2005-09-12 2014-03-18 Abela Pharmaceuticals, Inc. Methods for facilitating use of dimethyl sulfoxide (DMSO) by removal of same, related compounds, or associated odors
US9145362B2 (en) 2009-07-31 2015-09-29 Arkema France Solvent composition based on an oxide of an organic sulfide with masked odour
US9839609B2 (en) 2009-10-30 2017-12-12 Abela Pharmaceuticals, Inc. Dimethyl sulfoxide (DMSO) and methylsulfonylmethane (MSM) formulations to treat osteoarthritis
CN114057783A (zh) * 2021-12-23 2022-02-18 山东海科创新研究院有限公司 一种双草酸硼酸锂的制备方法
WO2022126043A1 (en) * 2020-12-09 2022-06-16 Exxonmobil Upstream Research Company Odor management for disulfide solvents and surfaces contacted therewith

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US6572847B2 (en) 2000-03-31 2003-06-03 The Lubrizol Corporation Elimination of odors from lubricants by use of a combination of thiazoles and odor masks
US6362374B1 (en) * 2000-05-01 2002-03-26 The Lubrizol Corporation Composition of and method for polysulfides having a reduced odor level
JP2006246855A (ja) * 2005-03-14 2006-09-21 Pokka Corp 高品質な飲料・食品の製造方法
FR2910348B1 (fr) * 2006-12-22 2012-05-18 Arkema France Agent de sulfuration de catalyseur d'hydrotraitement et son utilisation pour la presulfuration in-situ et ex-situ
JP2009067767A (ja) * 2006-12-28 2009-04-02 Takeda Chem Ind Ltd 戻り臭除去方法
US8331685B2 (en) 2008-05-28 2012-12-11 Apple Inc. Defining a border for an image
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FR2935142B1 (fr) * 2008-08-20 2010-11-19 Arkema France Dimethyldisulfure issu au moins partiellement de matieres renouvellables
CN101606533B (zh) * 2009-07-27 2012-05-02 山东美罗福农化有限公司 一种土壤熏蒸剂组合物及其应用
FR2962441A1 (fr) * 2010-07-08 2012-01-13 Arkema France Agents raft a odeur amelioree et polymeres a odeur amelioree obtenus a l'aide de ces agents
FR2965562B1 (fr) * 2010-09-30 2013-03-01 Arkema France Procede de preparation de disulfures de dialkyle
RU2457029C1 (ru) * 2011-03-15 2012-07-27 Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН Способ получения диметилсульфида
CN102816093B (zh) * 2012-08-14 2014-05-28 张怀有 甲硫醇氧化法生产二甲基二硫的方法
FR3023288B1 (fr) 2014-07-04 2016-07-15 Arkema France Procede de preparation de disulfure de dimethyle
FR3023287B1 (fr) 2014-07-04 2016-07-22 Arkema France Procede de preparation de methylmercaptan
FR3041636B1 (fr) 2015-09-30 2018-11-16 Arkema France Procede de production de mercaptans par hydrogenolyse enzymatique de disulfures a l'aide d'hydrogene
WO2020005524A1 (en) * 2018-06-27 2020-01-02 Exxonmobil Upstream Research Company Solvent mixtures for dissolving elemental sulfur, methods of utilizing the solvent mixtures, and methods of forming the solvent mixtures
FR3122877B1 (fr) 2021-05-11 2024-05-10 Arkema France Procédé de co-production de méthylmercaptan et de diméthyldisulfure à partir d’oxydes de carbone
FR3122876B1 (fr) 2021-05-11 2024-03-08 Arkema France Procédé de co-production d’alkylmercaptan et de dialkyldisulfure à partir d’alcool

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9186472B2 (en) 2005-09-12 2015-11-17 Abela Pharmaceuticals, Inc. Devices for removal of dimethyl sulfoxide (DMSO) or related compounds or associated odors and methods of using same
US8673061B2 (en) 2005-09-12 2014-03-18 Abela Pharmaceuticals, Inc. Methods for facilitating use of dimethyl sulfoxide (DMSO) by removal of same, related compounds, or associated odors
US8298320B2 (en) 2005-09-12 2012-10-30 Abela Pharmaceuticals, Inc. Systems for removing dimethyl sulfoxide (DMSO) or related compounds, or odors associated with same
US8435224B2 (en) 2005-09-12 2013-05-07 Abela Pharmaceuticals, Inc. Materials for facilitating administration of dimethyl sulfoxide (DMSO) and related compounds
US20090312273A1 (en) * 2005-09-12 2009-12-17 Abela Pharmaceuticals, Inc. Compositions compromising Dimethyl Sulfoxide (DMSO)
US8480797B2 (en) 2005-09-12 2013-07-09 Abela Pharmaceuticals, Inc. Activated carbon systems for facilitating use of dimethyl sulfoxide (DMSO) by removal of same, related compounds, or associated odors
US7955418B2 (en) 2005-09-12 2011-06-07 Abela Pharmaceuticals, Inc. Systems for removing dimethyl sulfoxide (DMSO) or related compounds or odors associated with same
US9427419B2 (en) 2005-09-12 2016-08-30 Abela Pharmaceuticals, Inc. Compositions comprising dimethyl sulfoxide (DMSO)
US8440001B2 (en) 2005-09-12 2013-05-14 Abela Pharmaceuticals, Inc. Systems for removing dimethyl sulfoxide (DMSO) or related compounds, or odors associated with same
US9186297B2 (en) 2005-09-12 2015-11-17 Abela Pharmaceuticals, Inc. Materials for facilitating administration of dimethyl sulfoxide (DMSO) and related compounds
US9145362B2 (en) 2009-07-31 2015-09-29 Arkema France Solvent composition based on an oxide of an organic sulfide with masked odour
US9839609B2 (en) 2009-10-30 2017-12-12 Abela Pharmaceuticals, Inc. Dimethyl sulfoxide (DMSO) and methylsulfonylmethane (MSM) formulations to treat osteoarthritis
US9855212B2 (en) 2009-10-30 2018-01-02 Abela Pharmaceuticals, Inc. Dimethyl sulfoxide (DMSO) or DMSO and methylsulfonylmethane (MSM) formulations to treat infectious diseases
US10596109B2 (en) 2009-10-30 2020-03-24 Abela Pharmaceuticals, Inc. Dimethyl sulfoxide (DMSO) or DMSO and methylsulfonylmethane (MSM) formulations to treat infectious diseases
WO2022126043A1 (en) * 2020-12-09 2022-06-16 Exxonmobil Upstream Research Company Odor management for disulfide solvents and surfaces contacted therewith
CN114057783A (zh) * 2021-12-23 2022-02-18 山东海科创新研究院有限公司 一种双草酸硼酸锂的制备方法

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TR199901835A2 (xx) 2000-02-21
NZ336950A (en) 2000-01-28
CA2277895C (fr) 2005-12-06
BR9902938A (pt) 2000-05-09
TWI224092B (en) 2004-11-21
EP0976726A1 (fr) 2000-02-02
ID23475A (id) 2000-04-27
UA64738C2 (uk) 2004-03-15
HUP9902626A2 (hu) 2000-08-28
ZA994890B (en) 2000-02-02
EP0976726B1 (fr) 2003-05-28
GC0000106A (en) 2005-06-29
CN1243825A (zh) 2000-02-09
US6743951B2 (en) 2004-06-01
HUP9902626A3 (en) 2002-01-28
SK283797B6 (sk) 2004-01-08
RU2219168C2 (ru) 2003-12-20
EG22544A (en) 2003-03-31
ATE241597T1 (de) 2003-06-15
RO120406B1 (ro) 2006-01-30
TR199901835A3 (tr) 2000-02-21
PT976726E (pt) 2003-10-31
US20020151753A1 (en) 2002-10-17
SG93838A1 (en) 2003-01-21
AR024507A1 (es) 2002-10-16
AU4234599A (en) 2000-02-24
CA2277895A1 (fr) 2000-01-31
US6639110B2 (en) 2003-10-28
PL191732B1 (pl) 2006-06-30
CO5231229A1 (es) 2002-12-27
JP4394201B2 (ja) 2010-01-06
CN1160325C (zh) 2004-08-04
KR20000012068A (ko) 2000-02-25
MY121424A (en) 2006-01-28
DE69908252D1 (de) 2003-07-03
HU224221B1 (hu) 2005-06-28
AU764075B2 (en) 2003-08-07
DK0976726T3 (da) 2003-09-29
NO993642D0 (no) 1999-07-27
KR100609276B1 (ko) 2006-08-09
FR2781795A1 (fr) 2000-02-04
HU9902626D0 (en) 1999-10-28
JP2000053637A (ja) 2000-02-22
NO313669B1 (no) 2002-11-11
FR2781795B1 (fr) 2000-09-08
DE69908252T2 (de) 2004-03-25
US20020156326A1 (en) 2002-10-24
PL334700A1 (en) 2000-02-14
BR9902938B1 (pt) 2010-12-14
SK101899A3 (en) 2000-02-14
NO993642L (no) 2000-02-01
ES2200481T3 (es) 2004-03-01

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