JPH0220596A - Odorant for fuel gas - Google Patents
Odorant for fuel gasInfo
- Publication number
- JPH0220596A JPH0220596A JP16887688A JP16887688A JPH0220596A JP H0220596 A JPH0220596 A JP H0220596A JP 16887688 A JP16887688 A JP 16887688A JP 16887688 A JP16887688 A JP 16887688A JP H0220596 A JPH0220596 A JP H0220596A
- Authority
- JP
- Japan
- Prior art keywords
- odorant
- sulfide
- gas
- unsatd
- odor
- 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.)
- Granted
Links
- 239000003205 fragrance Substances 0.000 title claims abstract description 40
- 239000002737 fuel gas Substances 0.000 title claims abstract description 9
- QPUBNJBEYGHVGN-UHFFFAOYSA-N 1-methylsulfanylbut-2-ene Chemical compound CSCC=CC QPUBNJBEYGHVGN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003568 thioethers Chemical class 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000007789 gas Substances 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 239000011593 sulfur Substances 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 15
- 235000019645 odor Nutrition 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003915 liquefied petroleum gas Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 5
- 230000009965 odorless effect Effects 0.000 description 4
- 239000003949 liquefied natural gas Substances 0.000 description 3
- OFSJHBMVJFGCIG-UHFFFAOYSA-N 2-methyl-3-methylsulfanylprop-1-ene Chemical group CSCC(C)=C OFSJHBMVJFGCIG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- AFGACPRTZOCNIW-UHFFFAOYSA-N ethenylsulfanylethane Chemical compound CCSC=C AFGACPRTZOCNIW-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- AMBKPYJJYUKNFI-UHFFFAOYSA-N methylsulfanylethene Chemical compound CSC=C AMBKPYJJYUKNFI-UHFFFAOYSA-N 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- -1 unsaturated sulfide compound Chemical class 0.000 description 2
- BQOGWZALJJSRCR-UHFFFAOYSA-N 1-prop-1-enylsulfanylbutane Chemical compound CCCCSC=CC BQOGWZALJJSRCR-UHFFFAOYSA-N 0.000 description 1
- GPAXHCWZVQHLFJ-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enylsulfanyl)but-2-ene Chemical compound CC(C)=CCSCC=C(C)C GPAXHCWZVQHLFJ-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 206010017740 Gas poisoning Diseases 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N sulfure de di n-propyle Natural products CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は液化天然ガスや液化石油ガス等の燃料ガス用付
臭剤に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to an odorant for fuel gas such as liquefied natural gas or liquefied petroleum gas.
（従来の技術）
従来から液化天然ガスやｊ良化石油ガス等の燃料ガスに
は、ガス漏れによる引火３ｓ発、ガス中毒を防止するた
めに特有な臭気物質（付臭剤）が添加されている。付臭
剤の望ましい性質としては、
■ 微量の添加量で効果のあること、
■ ガス臭であると認識できろこと、
■ 嗅覚疲労をおこしにくいこと、
■ 人間に対しては無害で毒性のないもの、■ 燃焼後
；ま無臭になるもの、
■ 供給系統への腐食、導管内で凝縮、化学反応をおこ
さないもの、
■ 家庭内での匂い、その他に実質が類似しないもの、
■ 土壌透過性のよいもの、
■ ＬＰＧボンベ中でガスの使用につれて付臭剤が′ａ
縮されないもの、であることが挙げられろ。(Prior art) Unique odor substances (odorants) have traditionally been added to fuel gases such as liquefied natural gas and JRyoka Petroleum Gas to prevent ignition and gas poisoning due to gas leaks. There is. Desirable properties of an odorant include: ■ It is effective when added in a small amount; ■ It is recognizable as a gas odor; ■ It does not cause olfactory fatigue; ■ It is harmless and non-toxic to humans. ■ Things that become odorless after combustion, ■ Things that do not corrode the supply system, condense in conduits, or cause chemical reactions, ■ Things that have no similar substance, such as odors in the home, etc.
■ Materials with good soil permeability; ■ As gas is used in LPG cylinders, odorants are
Name something that cannot be reduced.
従来の付臭剤は上記の要求特性を十分に満足していると
はいえず更に理想的な付臭剤の開発が望まれている。It cannot be said that conventional odorants fully satisfy the above-mentioned required characteristics, and it is desired to develop a more ideal odorant.
従来好ましいとされる付臭剤にはチオール類とスルフィ
ド類があり、スルフィド類の方がチオール類よりも認知
濃度（臭気の質がわからなくなる限界濃度をいい、気体
の単位容積中当たりの臭気成分濃度たとえばμｇ／ １
７１’等で表わす）が比較的高い。従来知られたスルフ
ィド系付臭剤はジメチルスルフィド、エチルメチルスル
フィド、ジエチルスルフィド、ビニルメチルスルフィド
、テトラヒドロチオフェン等の炭素数２から４までの化
合物である。Traditionally preferred odorants include thiols and sulfides, with sulfides having a higher perceived concentration (the limit concentration at which the quality of the odor becomes unnoticeable) than thiols. Concentration for example μg/1
71' etc.) is relatively high. Conventionally known sulfide odorants are compounds having 2 to 4 carbon atoms, such as dimethyl sulfide, ethyl methyl sulfide, diethyl sulfide, vinyl methyl sulfide, and tetrahydrothiophene.
（発明が解決しようとするＩｆ！１ｍ）本発明の目的は
従来知られな付臭剤に比し前記した要求特性をより満足
する付臭剤を提供することにあり、特に化学的に安定で
従来最もよいとされている公知のスルフィド系付臭剤よ
りも更に付臭効果の大きい付臭剤を提供することにある
。(If! 1m to be solved by the invention) An object of the present invention is to provide an odorant that satisfies the above-mentioned required characteristics more than conventionally known odorants, and in particular, is chemically stable. The object of the present invention is to provide an odorant that has an even greater odor-adding effect than the known sulfide-based odorants that are conventionally considered to be the best.
（ｆｌを解決するための手段）
本発明の燃料ガス用付臭剤は一般式 Ｒ−８−Ｒ但
しＲは炭素数４個の不飽和アルキル基を示し、Ｒは炭素
数１から５個の飽和もしくは不飽和アルキル基を示す、
にて表わされろ不飽和スルフィドを必須成分とするもの
である。(Means for solving fl) The fuel gas odorant of the present invention has the general formula R-8-R, where R represents an unsaturated alkyl group having 4 carbon atoms, and R represents an unsaturated alkyl group having 1 to 5 carbon atoms. represents a saturated or unsaturated alkyl group,
It is expressed as having unsaturated sulfide as an essential component.
本発明の付臭剤は上記一般式で示されろ不飽和スルフィ
ド単独からなるものでも、また通常の付臭剤と同様適宜
他の付臭成分や希釈成分等と混合したものでもよい。The odorant of the present invention may be composed of an unsaturated sulfide represented by the above general formula alone, or may be mixed with other odorant components, diluent components, etc., as appropriate, like ordinary odorants.
本発明の、付臭剤は付臭剤の添加を要する適宜の燃料ガ
ス、例えば液化天然ガスや液化石油ガス、に常法に従っ
て混入されろ。The odorant of the present invention is mixed into a suitable fuel gas requiring the addition of an odorant, such as liquefied natural gas or liquefied petroleum gas, in accordance with conventional methods.
次に臭気強度の試験結果を示す。Next, the odor intensity test results are shown.
臭気強度の測定は６名の充分に訓練されたパネルにより
官能判定を行うもので、試験は無臭室にて行い表（１）
に示す６段階奥９Ｃ強度表示法を用いて官能判定をした
。Odor intensity is measured using a sensory evaluation conducted by a panel of six well-trained people, and the test is conducted in an odor-free room as shown in Table (1).
Sensory evaluation was performed using the 6-level Oku9C intensity display method shown in .
この試験方法は悪臭公害研究会や日本環ｔｔ１衛生セン
ター内の臭気対策研究会などで用いられているものであ
る。This test method is used by the Offensive Odor Pollution Study Group and the Odor Control Study Group within the Japan Kankan TT1 Hygiene Center.
無臭室における奥９に強度測定の結果、従来用いられて
いるスルフィド系付臭剤の認知演度は、ジメチルスルフ
ィドで６０μｇ／ｒｎ’、メチルビニルスルフィドで３
０ ｐ ｇ／ ｒｎ” 、プロペニルブチルスルフィド
で２０μｇ／ ｍ 、テトラヒドロチオフェンで１５μ
ｇ／ ｍ”である。As a result of intensity measurement in the back 9 of an odor-free room, the recognition performance of conventionally used sulfide-based odorants was 60 μg/rn' for dimethyl sulfide and 3 for methyl vinyl sulfide.
0 p g/rn”, 20 μg/m for propenylbutyl sulfide, 15 μg for tetrahydrothiophene.
g/m”.
これに比べ本発明の炭素数４個の不飽和アルキル基をも
つ不飽和スルフィド化合物は１〜８μｇ／ｍで認知する
ことができ極めて付臭効果が高いことが判る。In comparison, the unsaturated sulfide compound having an unsaturated alkyl group having 4 carbon atoms according to the present invention can be detected at 1 to 8 μg/m, indicating that it has an extremely high odorizing effect.
第１図は付臭剤濃度と臭気強度の関係を示したものであ
り、ＡとＢは本発明の付臭剤の例として、Ａは２−ブテ
ニルメチルスルフィド、Ｂは２−メチル−２−プロペニ
ルメチルスルフィドを、またＣ−Ｅは従来のジスルフィ
ド系付臭剤としてＣはテトラヒドロチオフェン、Ｄはビ
ニルエチルスルフィド、Ｅはジメチルスルフィドを、そ
れぞれ単独で用いた場合を示す。Figure 1 shows the relationship between odorant concentration and odor intensity, where A and B are examples of the odorant of the present invention, A is 2-butenyl methyl sulfide, B is 2-methyl-2 -propenyl methyl sulfide, C-E is a conventional disulfide odorant, C is tetrahydrothiophene, D is vinyl ethyl sulfide, and E is dimethyl sulfide.
第１図からも本発明の付臭剤が従来最も優れているとさ
れる公知のスルフィド系付臭剤よりもさらに顕著に優れ
ていることが判る。It can also be seen from FIG. 1 that the odorant of the present invention is significantly superior to the known sulfide-based odorant, which is considered to be the best in the past.
本発明の付臭剤のうちでは前記一般式においてＲが２−
ブテニル基である化合物、特に礼が２−ブテニル基でＩ
ｔ、がメチル基である化合物が顕著な効果を示す。Among the odorants of the present invention, R in the general formula is 2-
Compounds with a butenyl group, especially compounds with a 2-butenyl group
Compounds in which t is a methyl group exhibit remarkable effects.
（発明の効果）
本発明の付臭剤は前記したとおり、従来最も優れるとさ
れろ公知のスルフィド系付臭剤に比し、より微量で大き
な付臭効果を示すが、これは経済性もさることながらガ
ス中の硫黄含有率を低く抑えろことを可能にするという
効果も示す。また本発明の付臭剤は有機溶剤に溶は易く
、水に不溶であり、吸着性が少なく、金属に対する腐食
がなく、化学的には極めて安定であるなど付臭剤に要求
される他の要求特性をも満足するものであり、その実用
的効果は従来の付臭剤に比し顕著に大きい。(Effects of the Invention) As mentioned above, the odorant of the present invention exhibits a greater odor-adding effect in a smaller amount than the known sulfide-based odorant, which is said to be the best in the past, but this is also economically efficient. Notably, it also has the effect of making it possible to keep the sulfur content in the gas low. In addition, the odorant of the present invention is easily soluble in organic solvents, insoluble in water, has low adsorption, does not corrode metals, and is extremely chemically stable. It also satisfies the required properties, and its practical effects are significantly greater than those of conventional odorants.
（実施例）
以下にその実施例を示すが本発明は実施例によって限定
されろものではない。(Example) Examples are shown below, but the present invention is not limited by the examples.
（実施例−１）
２−ブテニルメチルスルフィド５０重量％、ヘキサン５
０重量％を混合攪拌、脱水して製品とする。ついでこの
製品を無臭のＬＰＧｌｋｇに対して２０１Ｉｇの割合で
添加した。このガスを空気で１０００倍に希釈した状態
で臭気試験を行ったところ強いガス臭を感じた。(Example-1) 2-butenyl methyl sulfide 50% by weight, hexane 5
0% by weight is mixed, stirred, and dehydrated to produce a product. This product was then added at a ratio of 201 Ig to 1kg of odorless LPG. When this gas was diluted 1000 times with air and an odor test was conducted, a strong gas odor was detected.
（実施例−２）
２−メチル−１−プロペニルメチルスルフイド３０重量
％１テトラヒト四チオフエン２０重量％、ヘキサン５０
１１ｉ量％を混合攪拌、脱水して製品とする。ついでと
の製品を無臭の天然ガスに対して５ ｗｎｇ ／ Ｎ
ｒｎ’添加した。このガスを空気で１０００倍に希釈し
た状態で臭気試験を行ったところ強いガス臭を感じた。(Example-2) 30% by weight of 2-methyl-1-propenylmethyl sulfide, 20% by weight of 1-tetrahydrotetrathiophene, 50% by weight of hexane
11i mass % is mixed, stirred and dehydrated to obtain a product. Incidentally, the product is 5 wng/N against odorless natural gas.
rn' was added. When this gas was diluted 1000 times with air and an odor test was conducted, a strong gas odor was detected.
（実施例−３）
２−メチル−２−プロペニルミープロピルスルフィド３
０１ｆｌ量％、ジメチルスルフィド１０［ｉ％、テトラ
ヒドロチオフェン１０重量％、ヘキサン５０２１１量％
を混合撹拌、脱水して製品とする。ついでこの製品を無
臭のＬＰＧｌｋｇに対して３０■の割合で添加した。こ
のガスを空気で１０００倍に希釈した状態で臭気試験を
行ったところ強いガス奥を感じた。(Example-3) 2-methyl-2-propenyl-propylsulfide 3
01fl amount%, dimethyl sulfide 10 [i%, tetrahydrothiophene 10% by weight, hexane 50211% by weight
Mix, stir, and dehydrate to make a product. This product was then added at a rate of 30 μg per kg of odorless LPG. When this gas was diluted 1,000 times with air and an odor test was conducted, a strong gas was felt.
第１図は付臭剤濃度とそれに対する臭気強度の関係を表
わした線図である。
Ａ； ２−ブテニルメチルスルフィド、Ｂ； ２−メチ
ル−２−プロペニルメチルスルフィド、Ｃ：テトラヒド
ロチオフェン、Ｄ： ビニルエチルスルフィド、Ｅ：
ジメチルスルフィド。
同 弁理士 川 瀬 良 治FIG. 1 is a diagram showing the relationship between odorant concentration and odor intensity. A: 2-butenyl methyl sulfide, B: 2-methyl-2-propenyl methyl sulfide, C: tetrahydrothiophene, D: vinyl ethyl sulfide, E:
Dimethyl sulfide. Patent attorney Ryoji Kawase
Claims (1)
＿２は炭素数１から５個の飽和もしくは不飽和アルキル
基を示す、にて表わされる不飽和スルフィドを必須成分
とする燃料ガス用付臭剤。 ２、Ｒ＿１が２−ブテニル基である請求項１記載の燃料
ガス用付臭剤。 ３、不飽和スルフィドが２−ブテニルメチルスルフィド
である請求項１又は２記載の燃料ガス用付臭剤。[Claims] 1. General formula R_1-S-R_2 where R_1 represents an unsaturated alkyl group having 4 carbon atoms, and R
An odorant for fuel gas containing an unsaturated sulfide as an essential component, where _2 represents a saturated or unsaturated alkyl group having 1 to 5 carbon atoms. 2. The odorant for fuel gas according to claim 1, wherein R_1 is a 2-butenyl group. 3. The odorant for fuel gas according to claim 1 or 2, wherein the unsaturated sulfide is 2-butenylmethyl sulfide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63168876A JP2620119B2 (en) | 1988-07-08 | 1988-07-08 | Odorant for fuel gas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63168876A JP2620119B2 (en) | 1988-07-08 | 1988-07-08 | Odorant for fuel gas |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0220596A true JPH0220596A (en) | 1990-01-24 |
| JP2620119B2 JP2620119B2 (en) | 1997-06-11 |
Family
ID=15876200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63168876A Expired - Lifetime JP2620119B2 (en) | 1988-07-08 | 1988-07-08 | Odorant for fuel gas |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2620119B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500153A (en) * | 1994-07-05 | 1996-03-19 | The Procter & Gamble Company | Handwash laundry detergent composition having improved mildness and cleaning performance |
| WO2003050214A1 (en) * | 2001-12-11 | 2003-06-19 | Soda Aromatic Co.,Ltd. | Fuel gas odorant for fuel cell |
| JP2007327844A (en) * | 2006-06-07 | 2007-12-20 | Tokyo Gas Co Ltd | Evaluation method of odorant for fuel gas |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS512324A (en) * | 1974-05-30 | 1976-01-09 | Japan Broadcasting Corp | NIJIGEN JOHOJUSHINKI |
| JPS61185595A (en) * | 1985-02-12 | 1986-08-19 | Toho Gas Kk | Method for adding odor to liquefied natural gas |
-
1988
- 1988-07-08 JP JP63168876A patent/JP2620119B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS512324A (en) * | 1974-05-30 | 1976-01-09 | Japan Broadcasting Corp | NIJIGEN JOHOJUSHINKI |
| JPS61185595A (en) * | 1985-02-12 | 1986-08-19 | Toho Gas Kk | Method for adding odor to liquefied natural gas |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500153A (en) * | 1994-07-05 | 1996-03-19 | The Procter & Gamble Company | Handwash laundry detergent composition having improved mildness and cleaning performance |
| WO2003050214A1 (en) * | 2001-12-11 | 2003-06-19 | Soda Aromatic Co.,Ltd. | Fuel gas odorant for fuel cell |
| JP2007327844A (en) * | 2006-06-07 | 2007-12-20 | Tokyo Gas Co Ltd | Evaluation method of odorant for fuel gas |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2620119B2 (en) | 1997-06-11 |
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