EP1109881B1 - Odorierung von gas - Google Patents

Odorierung von gas Download PDF

Info

Publication number
EP1109881B1
EP1109881B1 EP99944331A EP99944331A EP1109881B1 EP 1109881 B1 EP1109881 B1 EP 1109881B1 EP 99944331 A EP99944331 A EP 99944331A EP 99944331 A EP99944331 A EP 99944331A EP 1109881 B1 EP1109881 B1 EP 1109881B1
Authority
EP
European Patent Office
Prior art keywords
gas
acrylate
process according
jonol
weight
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.)
Expired - Lifetime
Application number
EP99944331A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP1109881A1 (de
Inventor
Gerd Mansfeld
Ute Rohde
Fritz Henke
Heribert Kaesler
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.)
Dragoco Gerberding and Co GmbH
EOn Ruhrgas AG
Symrise AG
Original Assignee
Haarmann and Reimer GmbH
Ruhrgas AG
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.)
Filing date
Publication date
Application filed by Haarmann and Reimer GmbH, Ruhrgas AG filed Critical Haarmann and Reimer GmbH
Priority to EP03004711A priority Critical patent/EP1329495B1/de
Priority to SI9930239T priority patent/SI1109881T1/xx
Publication of EP1109881A1 publication Critical patent/EP1109881A1/de
Application granted granted Critical
Publication of EP1109881B1 publication Critical patent/EP1109881B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L3/00Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/003Additives for gaseous fuels
    • C10L3/006Additives for gaseous fuels detectable by the senses

Definitions

  • the present invention relates to gas odorization.
  • City and coke oven gases obtained by thermal processes contained intense smelling components and therefore had a strong inherent smell, so that escaping Gas could be perceived easily.
  • the acrylic acid esters A include acrylic acid methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl and dodecyl esters.
  • mixtures of acrylic acid-C 1 -C 6 -alkyl esters are used as component A; a particularly preferred combination contains methyl and ethyl acrylates side by side.
  • the acrylate mixtures can each contain the lower and the higher esters in a weight ratio of 9: 1 to 1: 9, preferably 7: 3 to 3: 7.
  • Preferred compounds (I) are e.g. 2-methylpyrazine, 2,3-dimethylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, tetramethylpyrazine, 2-ethylpyrazine, 2,3-diethylpyrazine, 5,2-methylethylpyrazine, 2,3-methylethylpyrazine, 5,2,3-methyldiethylpyrazine and 3,5,2- and 3,6,2-dimethylethylpyrazine, 2,3-methylethylpyrazine and tetramethylpyrazine are preferred.
  • the nitrogen compounds B can be used in amounts of 1 to 100, preferably 30 to 100, in particular 10 to 50 parts by weight per 1,000 parts by weight of A are used become.
  • the odorants can be used to protect against unwanted oxidation antioxidants included, as for example in Römpp-Lexikon Chemie Version 1.3 are described.
  • the antioxidants C are preferred in amounts of 0.01 to 5, in particular 0.05 up to 2, especially 0.1 to 1 part by weight per 1,000 parts by weight A.
  • Preferred gas odorants can, for example, have the following compositions have:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treating Waste Gases (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Polymerisation Methods In General (AREA)
EP99944331A 1998-08-17 1999-08-04 Odorierung von gas Expired - Lifetime EP1109881B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP03004711A EP1329495B1 (de) 1998-08-17 1999-08-04 Gasodorierungsmittel
SI9930239T SI1109881T1 (en) 1998-08-17 1999-08-04 Gas odorization method

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19837066A DE19837066A1 (de) 1998-08-17 1998-08-17 Odorierung von Gas
DE19837066 1998-08-17
PCT/EP1999/005639 WO2000011120A1 (de) 1998-08-17 1999-08-04 Odorierung von gas

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP03004711A Division EP1329495B1 (de) 1998-08-17 1999-08-04 Gasodorierungsmittel

Publications (2)

Publication Number Publication Date
EP1109881A1 EP1109881A1 (de) 2001-06-27
EP1109881B1 true EP1109881B1 (de) 2003-03-05

Family

ID=7877650

Family Applications (2)

Application Number Title Priority Date Filing Date
EP99944331A Expired - Lifetime EP1109881B1 (de) 1998-08-17 1999-08-04 Odorierung von gas
EP03004711A Expired - Lifetime EP1329495B1 (de) 1998-08-17 1999-08-04 Gasodorierungsmittel

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP03004711A Expired - Lifetime EP1329495B1 (de) 1998-08-17 1999-08-04 Gasodorierungsmittel

Country Status (23)

Country Link
US (1) US7108803B1 (es)
EP (2) EP1109881B1 (es)
JP (1) JP3818060B2 (es)
AT (2) ATE376045T1 (es)
AU (1) AU750863B2 (es)
BR (1) BR9913053A (es)
CA (1) CA2340729C (es)
CZ (1) CZ296172B6 (es)
DE (3) DE19837066A1 (es)
DK (2) DK1109881T3 (es)
EE (1) EE200100095A (es)
ES (2) ES2189476T3 (es)
HU (1) HU227576B1 (es)
IL (1) IL141169A (es)
MX (1) MXPA01001769A (es)
NO (1) NO330898B1 (es)
PL (1) PL190984B1 (es)
PT (1) PT1109881E (es)
RU (1) RU2226207C2 (es)
SK (1) SK286720B6 (es)
TR (1) TR200100463T2 (es)
WO (1) WO2000011120A1 (es)
YU (1) YU49389B (es)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003201487A (ja) * 2002-01-10 2003-07-18 Toyota Motor Corp 燃料電池用燃料ガス
DE10235750A1 (de) * 2002-08-05 2004-02-19 Symrise Gmbh & Co. Kg Gasodorierung mit Ketonen
DE10235753A1 (de) * 2002-08-05 2004-02-19 Symrise Gmbh & Co. Kg Ester zur Odorierung von Brenngasen
DE10235756A1 (de) * 2002-08-05 2004-02-19 Symrise Gmbh & Co. Kg Gasodorierung mit Phenolen und/oder Phenolethern
DE10235752A1 (de) * 2002-08-05 2004-02-19 Symrise Gmbh & Co. Kg Gasodorierung mit Carbonsäuren und Alkinen
WO2004092054A2 (en) * 2002-08-13 2004-10-28 Enersol Inc., N.A., L.P. Hydrogen odorants and odorant selection method
DE10240028A1 (de) * 2002-08-27 2004-03-11 Symrise Gmbh & Co. Kg Schwefelarme Odoriermittel für Flüssiggas
US6820464B2 (en) 2002-12-16 2004-11-23 Air Products And Chemicals, Inc. Odorized seals for the detection of gas leak
US7192459B2 (en) 2002-12-16 2007-03-20 Air Products And Chemicals, Inc. Addition of odorants to gases for leak detection
US7024869B2 (en) 2002-12-16 2006-04-11 Air Products And Chemicals, Inc. Addition of odorants to hydrogen by incorporating odorants with hydrogen storage materials
DE10359743A1 (de) * 2003-12-19 2005-07-14 Symrise Gmbh & Co. Kg Odorierung von Brenngas mit schwefelarmen Odoriermitteln
FR2868790B1 (fr) * 2004-04-08 2008-07-25 Arkema Sa Melange odorisant pour combustible gazeux inodore
RU2377279C2 (ru) 2004-11-09 2009-12-27 Живодан Са Одорант газа
BRPI0518020A (pt) 2004-11-09 2008-10-21 Givaudan Sa odorante para gás
WO2006128314A1 (en) * 2005-05-30 2006-12-07 Givaudan Sa Gas odorant comprising a cycloalkadiene
FR2891841B1 (fr) * 2005-10-11 2007-12-28 Arkema Sa Melange odorisant pour combustible gazeux inodore
BE1016960A3 (nl) * 2006-01-19 2007-11-06 Rostyne Alexander Jozef Magdal Verbeterde helikopter.
FR2902798B1 (fr) * 2006-06-26 2009-04-24 Arkema France Melange odorisant pour combustible gazeux inodore
WO2009143327A1 (en) * 2008-05-21 2009-11-26 Enersol, Inc.., N.A. L.P. Hydrogen odorization
PL3039100T3 (pl) 2013-10-01 2017-11-30 Aygaz Anonim Sirketi Bezsiarkowy nawaniacz gazu
EP3174561A4 (en) 2014-07-30 2019-07-24 GPCP IP Holdings LLC AIR FRESH DISPENSERS, CARTRIDGES THEREOF, SYSTEMS AND METHOD
FR3065375B1 (fr) 2017-04-25 2019-06-28 Arkema France Procede d'odorisation de fluide cryogenique
CN113956904A (zh) * 2021-11-25 2022-01-21 沈阳光正工业有限公司 一种可燃气体用无硫含量的气味添加剂及其制备方法
CN114507552A (zh) * 2022-01-24 2022-05-17 成都小号科技有限公司 一种适用于可燃气体泄露警示的低硫添加剂
CN114561236B (zh) * 2022-01-24 2023-06-27 成都小号科技有限公司 一种适用于可燃气体泄露警示的环保添加剂
US11712672B1 (en) 2022-05-03 2023-08-01 GPL Odorizers LLC Accurate odorization control
CN115057764A (zh) * 2022-06-30 2022-09-16 辽宁厚安科技有限公司 一种无硫加臭剂用阻聚剂
CN115340848B (zh) * 2022-07-27 2024-05-28 湖北瑞能华辉能源管理有限公司 具有警示作用的碳氢制冷剂及其应用

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3620982A (en) * 1968-09-18 1971-11-16 Int Flavors & Fragrances Inc Perfume composition containing dihydroisocaryophyllene oxide
JPS5134841B2 (es) * 1972-01-28 1976-09-29
DE2427314C3 (de) 1974-06-06 1978-04-20 Siemens Ag, 1000 Berlin Und 8000 Muenchen Verriegelbarer Betätigungshandgriff für gekapselte Schaltgeräte mit variablem Schwenkbereich
JPS5912386B2 (ja) * 1974-09-19 1984-03-22 新日本製鐵株式会社 消耗電極式自動ア−ク溶接方法とその装置
JPS5845005B2 (ja) 1976-09-14 1983-10-06 日本ビクター株式会社 光変調の変調度安定化装置
JPS55104393A (en) 1979-02-02 1980-08-09 Nippon Zeon Co Ltd Fuel gas odorant
JPS5842235A (ja) 1981-09-08 1983-03-11 Toshiba Corp 半導体乾式エツチング装置
US4487613A (en) * 1983-09-26 1984-12-11 International Flavors & Fragrances Inc. Odorization of combustible hydrocarbon gases
JPS621998A (ja) 1985-06-27 1987-01-07 松本 嘉司 シ−ルドトンネル掘削装置
US5321005A (en) * 1992-12-09 1994-06-14 International Flavors & Fragrances Inc. Flavor and fragrance compositions produced using process for quantitatively and qualitatively substantially continuously analyzing the aroma emitted from a living fruit
CA2262462C (en) * 1996-08-02 2009-01-13 Andreas Ott Use of 1-nonen-3-one as a flavouring agent

Also Published As

Publication number Publication date
TR200100463T2 (tr) 2001-07-23
ES2292868T3 (es) 2008-03-16
DK1109881T3 (da) 2003-07-14
EP1329495A3 (de) 2006-04-05
NO330898B1 (no) 2011-08-08
MXPA01001769A (es) 2002-06-04
JP3818060B2 (ja) 2006-09-06
WO2000011120A1 (de) 2000-03-02
EP1329495A2 (de) 2003-07-23
AU5730899A (en) 2000-03-14
JP2002523557A (ja) 2002-07-30
US7108803B1 (en) 2006-09-19
PL346017A1 (en) 2002-01-14
NO20010691D0 (no) 2001-02-09
EP1329495B1 (de) 2007-10-17
ATE233802T1 (de) 2003-03-15
DE59914530D1 (de) 2007-11-29
ES2189476T3 (es) 2003-07-01
CZ296172B6 (cs) 2006-01-11
IL141169A (en) 2004-09-27
HU227576B1 (en) 2011-08-29
PL190984B1 (pl) 2006-02-28
DE59904474D1 (de) 2003-04-10
CZ2001616A3 (cs) 2001-07-11
SK2332001A3 (en) 2001-09-11
DE19837066A1 (de) 2000-02-24
SK286720B6 (sk) 2009-04-06
CA2340729A1 (en) 2000-03-02
YU11201A (sh) 2003-01-31
EP1109881A1 (de) 2001-06-27
YU49389B (sh) 2005-11-28
ATE376045T1 (de) 2007-11-15
DK1329495T3 (da) 2007-11-26
AU750863B2 (en) 2002-08-01
PT1109881E (pt) 2003-07-31
RU2226207C2 (ru) 2004-03-27
EE200100095A (et) 2002-06-17
HUP0103084A2 (hu) 2001-11-28
NO20010691L (no) 2001-02-09
BR9913053A (pt) 2001-05-08
HUP0103084A3 (en) 2003-01-28
IL141169A0 (en) 2002-02-10
CA2340729C (en) 2006-12-12

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