CN101056964A - Gas odorant - Google Patents
Gas odorant Download PDFInfo
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- CN101056964A CN101056964A CN 200580038263 CN200580038263A CN101056964A CN 101056964 A CN101056964 A CN 101056964A CN 200580038263 CN200580038263 CN 200580038263 CN 200580038263 A CN200580038263 A CN 200580038263A CN 101056964 A CN101056964 A CN 101056964A
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- CN
- China
- Prior art keywords
- odorant
- gas
- pyrazine
- fuel
- fuel gas
- 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.)
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- 239000003205 fragrance Substances 0.000 title claims abstract description 58
- 239000007789 gas Substances 0.000 claims abstract description 49
- -1 alkoxy alkynes Chemical class 0.000 claims abstract description 33
- 239000002737 fuel gas Substances 0.000 claims abstract description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 19
- 239000005864 Sulphur Substances 0.000 claims description 13
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 11
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000446 fuel Substances 0.000 claims description 10
- YAIMUUJMEBJXAA-UHFFFAOYSA-N 2-(2-methylpropyl)pyrazine Chemical compound CC(C)CC1=CN=CC=N1 YAIMUUJMEBJXAA-UHFFFAOYSA-N 0.000 claims description 4
- DXLUAQMRYDUZCJ-UHFFFAOYSA-N 2-(methoxymethyl)pyrazine Chemical compound COCC1=CN=CC=N1 DXLUAQMRYDUZCJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001154 2-(methoxymethyl)pyrazine Substances 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 4
- 235000019634 flavors Nutrition 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003915 liquefied petroleum gas Substances 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- KDBZVULQVCUNNA-UHFFFAOYSA-N 2,5-di-tert-butylphenol Chemical class CC(C)(C)C1=CC=C(C(C)(C)C)C(O)=C1 KDBZVULQVCUNNA-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- WXEHBUMAEPOYKP-UHFFFAOYSA-N methylsulfanylethane Chemical compound CCSC WXEHBUMAEPOYKP-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Landscapes
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention refers to the use as gas odorant of alkoxy alkynes of formula (I) wherein R<1> is methoxy or ethoxy; and R<2> is hydrogen or methyl, to a process of odorizing gas and to fuel gas comprising it.
Description
The present invention relates to the purposes of alkoxy alkyne, give the method and the fuel gas that comprises them of gas smell-adding as gas odorant.
Because the relative high purity with them in source of fuel gas causes them tasteless basically.Leakage then can not form explosive mixture apace if in time notice with high-risk possibility.For security reason, therefore come to gas smell-adding by adding odorant.For example, in whole European Union area, use the odorant of tetramethylene sulfide (THT), usually as unique odorant as city gas.In the North America, tert-butyl mercaptan is widely used as main odorant, and usually is used in combination with other alkyl sulfhydryl and various sulfide and disulphide.For example, for liquefied petroleum gas, ethanethio is used as odorant.These compounds especially are very suitable for as gas odorant, this be because they have very powerful, make us unhappy and special smell.In addition, because they are used very chronically, therefore, they generally are associated with fuel gas now, therefore satisfy the requirement of special and known gas leakage warning.Yet from the environment aspect, sulphur compound is so unsuitable, and this is because form sulfurous gas in this burning of gas process that adds flavor.In addition, known to changing into H
2During S, sulfur-based compound is poisoned the electrode catalyst of fuel cell, and this causes fuel cell performance seriously to descend.
In order highly to be suitable as gas odorant, the mixture of compound or compound (being composition) must satisfy many requirements.Especially, for fear of obscuring danger, the smell of gas odorant needs:
-enough unusual, so that exist considerably less danger that it is identified as any other smell.It is desirable to, it should be associated with the smell of present gas odorant immediately, this is because they widely-used makes smell identification easily for most of users of this gas.
-have detection threshold than the low several magnitude of the limits of explosion of fuel gas so that have average sense of smell and an average physiological situation everyone can detect this smell.
In addition, gas odorant must be stable under the storage of fuel gas and transport condition.
Carried out that several trials substitute or reduced the use of the sulphur compound of the gas odorant that acts as a fuel at least.For example, DE-A 19837066 discloses the purposes of the mixture of alkyl acrylate and nitrogen compound.The fuel gas odorant that contains alkynes (for example fourth-1-alkynes, vinylacetylene and hexin) and be selected from least two kinds of compounds in methyl acrylate, ethyl propenoate, methyl methacrylate, allyl methacrylate(AMA), ethyl propionate, methyl butyl and the methyl isobutyrate is disclosed in JP-A-55-104393 (summary).The problem of alkyl acrylate is that their smell is very similar to for example some acrylplasticss and paint.
Therefore, continuing needs to seek the alternate odorant, and this odorant is suitable for as gas odorant.Surprisingly, find some alkynes be particularly suitable for acting as a fuel odorant of gas.
Therefore, one aspect of the present invention alkoxy alkyne of relating to general formula (I) purposes of gas odorant that acts as a fuel:
R wherein
1It is methoxy or ethoxy; With
R
2Be hydrogen or methyl.
Especially preferred 1-methoxyl group-butylene-3-alkynes gas odorant that acts as a fuel.
The term that in implication of the present invention, uses " gas odorant " can be meant single odor compound or this odor compound mixture the two.
Fuel gas generally is used for perhaps being used for heating, illumination and digestion process by burning generates electric energy in the power station in buildings.They also can be used for generating hydrogen for using by usually being called the technology of " reformation " in hydrogen fuel cell.The term that uses in the application's implication " fuel gas " representative is as any combustible hydrogen or the appropriate hydrocarbon gas of main or the less important energy.They are (25 ℃ of normal pressure and temperatures; 1000mbar) be gas form down, but also can liquid form processing transport and store for convenient.Fuel gas includes but not limited to city or cities and towns gas, Sweet natural gas (comprising its liquefied form), liquefied petroleum gas (LPG, it is the mixture of the alkane that separates and be made up of butane and propane basically) and hydrogen from gasoline.Alkynes, for example acetylene also is suitable as fuel gas.In the application's implication, oxygenated hydrocarbon, for example dme (it can be used as the energy or be used to generate the hydrogen that fuel cell is used by burning) also belongs to the fuel gas class.
Compound of the present invention can use separately or in conjunction with known gas odorant (being sulphur compound and the compound that does not conform to sulphur).Especially preferred and the binding substances of the gas odorant of sulfur-bearing (for example pyrazine) not, the consumption of wherein said pyrazine is preferably maximum 10 weight parts in alkoxy alkyne or its mixture of 100 weight part general formulas (I), more preferably maximum 5.5 weight parts, for example 0.1-5.5 weight part.If combine with sulphur compound, then to preferably include the total amount based on gas odorant be maximum 60wt% to the fuel gas odorant, more preferably 1-30wt%, for example sulphur compound of 1-10wt% or its mixture.
Suitable pyrazine includes but not limited to ethyl pyrazine, methoxyl group isobutyl pyrazine and methoxymethyl pyrazine.In JP-A-08-60167, disclose further suitable pyrazine, be introduced into by reference at this.By The compounds of this invention and more a spot of pyrazine are mixed, can realize even better result.
Suitable sulphur compound includes but not limited to be selected from following compound: C
1-C
4Alkyl sulfhydryl, for example tert-butyl mercaptan and ethanethio; Aryl mercaptan, for example benzyl mercaptan; Organic sulfide and disulphide, for example dimethyl thioether and ethyl-methyl thioether; With tetramethylene sulfide and derivative thereof.
Therefore, the gas odorant that especially preferably comprises following substances:
A) alkoxy alkyne of at least a general formula (I); With
B) at least a pyrazine compound, wherein said pyrazine are preferably selected from ethyl pyrazine, methoxyl group isobutyl pyrazine and methoxymethyl pyrazine; And/or
C) at least a sulphur compound.
In special embodiment, gas odorant comprises the alkoxy alkyne and at least a sulphur compound of at least a general formula (I).
Also can add other vehicle (for example antioxidant) in odorant or directly join in the fuel gas of flavor.Suitable antioxidant includes but not limited to butylhydroxy anisole, 2,5-DI-tert-butylphenol compounds (lonol), hydroquinone monomethyl ether and alpha-tocopherol, 2,6 ditertiary butyl p cresol and tertiary butyl hydroxytoluene.
The further aspect of the present invention is the fuel gas that contains the gas odorant, and described gas odorant comprises:
A) alkoxy alkyne of at least a general formula (I); With
B) randomly, at least a pyrazine compound, wherein said pyrazine are preferably selected from ethyl pyrazine, methoxyl group isobutyl pyrazine and methoxymethyl pyrazine;
C) and randomly, at least a sulphur compound.
In special embodiment, fuel gas comprises the alkoxy alkyne that comprises at least a general formula (I) and the gas odorant of at least a sulphur compound.
The dosage of gas odorant of the present invention in fuel gas depends primarily on the composition of odorant, and can change between about 100ppm 1, preferably between 5 to 50ppm, more preferably between 20 to 40ppm.
In addition, the present invention relates to add the method for flavor to fuel gas, this method comprises that at least a above-described alkoxy alkyne of mixing significant quantity is as odorant.
Fuel gas odorant of the present invention at room temperature is a liquid, and therefore optionally odorant preparation of compositions and mixing odorant/odorant composition all are not crucial in fuel gas.Can use method known to those skilled in the art and equipment.
Refer now to following non-limiting example, further describe the present invention.
Embodiment 1: the gas odorant composition
Table 1 shows preferred gas odorant of the present invention and known gas odorant (1-5) in contrast.
Abbreviation below in table 1, using:
MET:1-methoxyl group-butylene-3-alkynes
MEP: ethyl pyrazine
THT: tetramethylene sulfide
TBM: tert-butyl mercaptan
DMS: dimethyl thioether
EAC: ethyl propenoate
MAC: methyl acrylate
Table 1
| Odorant | Odor compound | ||
| MET | MEP | Other compound | |
| A | 100 | ||
| B | 95 | 5 | |
| C | 80 | 20(TBM) | |
| D | 80 | 14(DMS)，6(TBM) | |
| 1 | 100(THT) | ||
| 2 * | 2.5 | 60(EAC)，37.5(MAC) | |
| 3 ** | Labogaz 206 | ||
| 4 *** | 70(DMS)，30TBM | ||
| 5 | 100(TBM) | ||
wt％
*: Gasodor S-FREE
, as disclosed at Gas und Wasserfach, Gas, Erdgas142/11 732,779-780,782-784 (November calendar year 2001).
*: have the commercial propane/butane gas of the mixture of sulphur compound as gas odorant.In France with Campingaz
TMForm is sold.
* *:, be used for the mixture of the gas odorant of LPG in France.
Embodiment 2: with the comparative studies of known gas odorant
Preparation contains the isobutane gas aerosol of odorant A, B, 1,2 or 3 (embodiment 1, table 1) that dosage is 40ppm.This aerosol spray is spread across 7m
3Cell in, and by be familiar with 30 of the gas smell independently the testee hear by the portlet of this cell door and smell.Inquire them, keeping firmly in mind on the basis of smell, with 4 minutes grade evaluation smell, (4=agrees (that is, equaling the smell of gas) fully, and the 3=great majority agree that the 2=great majority are disagreed with and 1=disagrees with fully).The blind test odorant, the testee does not know to form.Listed average result in the table 2.
Table 2
| Odorant | Similar degree | Odorant | Similar degree | |
| A | 2.33 | 1 | 3.88 | |
| B | 2.40 | 2 | 1.84 | |
| C | 3.24 | 3 | 3.90 | |
| D | 3.00 |
Claims (7)
1. the alkoxy alkyne of general formula (I) purposes of gas odorant that acts as a fuel:
R wherein
1It is methoxy or ethoxy; With
R
2Be hydrogen or methyl.
2. the 1-methoxyl group-butylene of claim 1-3-alkynes purposes of gas odorant that acts as a fuel.
3. fuel gas odorant, it comprises the alkoxy alkyne of general formula (I):
R wherein
1It is methoxy or ethoxy; With
R
2Be hydrogen or methyl.
4. the fuel gas odorant of claim 3, it further comprises at least a sulphur compound.
5. claim 3 or 4 fuel gas odorant, it further comprises at least a pyrazine compound, and wherein said pyrazine is preferably selected from ethyl pyrazine, methoxyl group isobutyl pyrazine and methoxymethyl pyrazine.
6. fuel gas, it comprises the gas odorant of claim 3,4 or 5 any one definition.
7. one kind adds the method for flavor to fuel gas, the alkoxy alkyne that this method comprises at least a general formula (I) that mixes significant quantity as odorant in fuel gas:
R wherein
1It is methoxy or ethoxy; And R
2Be hydrogen or methyl.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04300770 | 2004-11-09 | ||
| EP04300770.7 | 2004-11-09 | ||
| EP05290463.8 | 2005-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101056964A true CN101056964A (en) | 2007-10-17 |
Family
ID=38796144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200580038263 Pending CN101056964A (en) | 2004-11-09 | 2005-11-08 | Gas odorant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101056964A (en) |
-
2005
- 2005-11-08 CN CN 200580038263 patent/CN101056964A/en active Pending
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |