JP2002146371A - Colorless petroleum marker dye - Google Patents
Colorless petroleum marker dyeInfo
- Publication number
- JP2002146371A JP2002146371A JP2001284464A JP2001284464A JP2002146371A JP 2002146371 A JP2002146371 A JP 2002146371A JP 2001284464 A JP2001284464 A JP 2001284464A JP 2001284464 A JP2001284464 A JP 2001284464A JP 2002146371 A JP2002146371 A JP 2002146371A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- hydrogen
- formula
- bromo
- 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.)
- Withdrawn
Links
- 239000003550 marker Substances 0.000 title claims abstract description 12
- 239000003208 petroleum Substances 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000003209 petroleum derivative Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000003350 kerosene Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002283 diesel fuel Substances 0.000 claims description 3
- 239000000446 fuel Substances 0.000 claims description 3
- 239000000295 fuel oil Substances 0.000 claims description 3
- 239000003502 gasoline Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- CPBJMKMKNCRKQB-UHFFFAOYSA-N 3,3-bis(4-hydroxy-3-methylphenyl)-2-benzofuran-1-one Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 CPBJMKMKNCRKQB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 241000900241 Arua Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LDKDGDIWEUUXSH-UHFFFAOYSA-N Thymophthalein Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C LDKDGDIWEUUXSH-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
- C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/20—Organic compounds containing halogen
- C10L1/202—Organic compounds containing halogen aromatic bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/20—Organic compounds containing halogen
- C10L1/205—Organic compounds containing halogen carboxylic radical containing compounds or derivatives, e.g. salts, esters
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)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
Description
【0001】本発明は、概して、無色のマーカー染料と
液体石油製品を含む組成物、並びに、石油製品をマーキ
ングする方法に関する。特定のフタレイン誘導体が、石
油用途、およびペイントおよびプラスチックをはじめと
する他の産業用途におけるマーカーとして公知であり、
使用されている。例えば、米国特許第6002056号
はチモールフタレイン、クレゾールフタレインおよび関
連する化合物を、石油製品のためのマーカーとして使用
することを開示する。しかし、この参考文献は2つのフ
ェノール性ヒドロキシル基を有する化合物しか開示して
おらず、マーカーとしてのフタレインエステルの使用を
示唆していない。[0001] The present invention relates generally to compositions comprising a colorless marker dye and a liquid petroleum product, as well as a method for marking petroleum products. Certain phthalein derivatives are known as markers in petroleum applications and other industrial applications, including paints and plastics,
It is used. For example, US Pat. No. 6,020,056 discloses the use of thymolphthalein, cresolphthalein and related compounds as markers for petroleum products. However, this reference only discloses compounds having two phenolic hydroxyl groups and does not suggest the use of phthalein esters as markers.
【0002】フタレイン誘導体の欠点は、石油製品中で
の該フタレイン誘導体の典型的に低い溶解性から生じて
いる。この特性の結果、フタレインマーカーは、マーキ
ングを除くことが望まれる場合に故意に、またはマーキ
ングされた石油製品が貯蔵タンク内で下層の水と接触す
る結果、水での抽出によってマーキングされた石油製品
から除かれることができる。本発明によって取り扱われ
る問題は、石油製品中で向上された溶解性を有する無色
のマーカー染料を見出すことである。[0002] The disadvantages of phthalein derivatives result from the typically low solubility of the phthalein derivatives in petroleum products. As a result of this property, the phthalein marker can be used to deliberately mark the petroleum that has been marked by extraction with water, either deliberately when it is desired to remove the marking, or as a result of the marked petroleum product contacting the underlying water in the storage tank. Can be removed from the product. The problem addressed by the present invention is to find colorless marker dyes with improved solubility in petroleum products.
【0003】本発明は、液体石油製品、および視覚的に
検出可能でない量で式Iの化合物を含む組成物に関す
る。[0003] The present invention relates to liquid petroleum products and compositions comprising a compound of formula I in an amount which is not visually detectable.
【0004】[0004]
【化4】 Embedded image
【0005】式Iにおいては、R1はC1−C18アル
キル、C1−C18アルケニル、アリールまたはアルア
ルキルであり;R2、R3およびR4は独立して、水
素、C 1−C12アルキル、クロロまたはブロモであ
り;さらにR5は水素、クロロまたはブロモである。本
発明は、視覚的に検出できない量の式Iの化合物をマー
カーとして石油製品に添加し、該マーカーが顕色剤と接
触して発色することを含む、液体石油製品をマーキング
する方法にも関する。In formula I, R1Is C1-C18Al
Kill, C1-C18Alkenyl, aryl or arua
Luquil; R2, R3And R4Independently of the water
Elementary, C 1-C12Alkyl, chloro or bromo
R;5Is hydrogen, chloro or bromo. Book
The invention provides a method for producing visually undetectable amounts of a compound of Formula I.
The car is added to petroleum products as a car, and the marker contacts the developer.
Marking liquid petroleum products, including touching to develop color
How to do it.
【0006】「アルキル」基とは、直鎖、分岐鎖または
環式の配列で、1〜18個の炭素原子を有する炭化水素
基をいう。アルキル基は、ハロ、アルコキシ、アルカノ
イルまたはアミド基の1以上で置換可能であり、アルコ
キシ、アルカノイルおよびアミド基は、同様に1以上の
ハロ置換基で置換されることができる。好ましくは、ア
ルキル基は非置換のものである。「アルケニル」基と
は、「アルキル基」における少なくとも1つの単結合が
二重結合で置き換えられているものである。「アリール
基」とは、芳香族化合物に由来する置換基であり、窒
素、酸素および硫黄から選択されるヘテロ原子を有する
ヘテロ環式芳香族化合物を含む。アリール基は、全部で
5〜20個のリングアトム(ring atom)を有
し、別々のまたは縮合した1以上の環を有する。アリー
ル基は、ハロ、アルキル、アルケニル、アルコキシ、ア
ルカノイルまたはアミド基の1以上で置換されることが
でき、アルキル、アルケニル、アルコキシ、アルカノイ
ルまたはアミド基は、1以上のハロ基で置換されること
ができる。好ましくは、アリール基は非置換のものであ
るか、またはハロもしくはアルキル基だけで置換された
ものである。「アルアルキル」基とは、「アリール」基
で置換された「アルキル」基である。[0006] An "alkyl" group refers to a hydrocarbon group having from 1 to 18 carbon atoms in a straight, branched or cyclic arrangement. Alkyl groups can be substituted with one or more halo, alkoxy, alkanoyl or amide groups, and alkoxy, alkanoyl and amide groups can be similarly substituted with one or more halo substituents. Preferably, the alkyl groups are unsubstituted. An “alkenyl” group is one in which at least one single bond in the “alkyl group” has been replaced with a double bond. An “aryl group” is a substituent derived from an aromatic compound, and includes a heterocyclic aromatic compound having a heteroatom selected from nitrogen, oxygen, and sulfur. Aryl groups have a total of 5 to 20 ring atoms and have one or more separate or fused rings. An aryl group can be substituted with one or more halo, alkyl, alkenyl, alkoxy, alkanoyl, or amide groups, and an alkyl, alkenyl, alkoxy, alkanoyl, or amide group can be substituted with one or more halo groups. it can. Preferably, the aryl groups are unsubstituted or substituted only with halo or alkyl groups. An “aralkyl” group is an “alkyl” group substituted with an “aryl” group.
【0007】R2、R3およびR4は、水素、または1
〜4つの炭素原子を有するアルキルであることが好まし
い。また、R1は、1〜4つの炭素原子を有するアルキ
ルであることが好ましい。R5は水素であることが好ま
しい。液体石油製品はガソリン、ディーゼル燃料、ジェ
ット燃料、燃料油、ケロシンまたは灯油(lamp o
il)であることが好ましい。式Iの化合物は0.5p
pm〜100ppmの量で存在することが好ましく、
0.5ppm〜10ppmの量で存在することがより好
ましい。式Iの化合物は、高沸点の炭化水素可溶性溶媒
との混合物として調製されることが好ましい。好ましい
溶媒としては、1−オクチル−2−ピロリドン、混合メ
チルナフタレン類(Exxon Corporatio
nによって、AROMATIC 200として販売され
ている)、または芳香族炭化水素溶媒が挙げられる。溶
媒中でのマーカーの好ましい濃度は20%〜30%であ
る。顕色剤は強塩基性の薬剤であり、例えば、アルカリ
金属または4級アンモニウムイオンの水酸化物である。
好ましくは、該薬剤は4級アンモニウムの水酸化物であ
る。本発明は、さらに、R1がプロピルであり、R2が
メチルであり、R3、R4およびR5が水素である、式
Iの化合物にも関する。本化合物の調製方法は実施例1
に開示されている。R 2 , R 3 and R 4 are hydrogen or 1
Preferably, it is an alkyl having up to 4 carbon atoms. Also, R 1 is preferably an alkyl having 1 to 4 carbon atoms. Preferably, R 5 is hydrogen. Liquid petroleum products include gasoline, diesel fuel, jet fuel, fuel oil, kerosene or kerosene (lamp o
il). The compound of formula I has 0.5 p
preferably present in an amount of from pm to 100 ppm,
More preferably, it is present in an amount of 0.5 ppm to 10 ppm. The compounds of formula I are preferably prepared as a mixture with a high boiling hydrocarbon soluble solvent. Preferred solvents include 1-octyl-2-pyrrolidone, mixed methylnaphthalenes (Exxon Corporation)
n, sold as AROMATIC 200), or aromatic hydrocarbon solvents. The preferred concentration of the marker in the solvent is between 20% and 30%. The developer is a strongly basic drug, for example, a hydroxide of an alkali metal or quaternary ammonium ion.
Preferably, the agent is a quaternary ammonium hydroxide. The invention further relates to compounds of formula I, wherein R 1 is propyl, R 2 is methyl and R 3 , R 4 and R 5 are hydrogen. The method for preparing this compound is described in Example 1.
Is disclosed.
【0008】実施例 実施例1 o−クレゾールフタレインのジ−n−ブチルエステルの
調製 スターラー、熱電対および凝縮器が備え付けられた10
0mLの3つ首丸底フラスコに、次の原料物質が添加さ
れた:(1)o−クレゾールフタレイン、1.73g
(0.005モル);(2)水、30mL;(3)50
%NaOH、0.8g;(4)Na2CO3、0.6
g;および(5)キシレン、8g。混合物が20〜25
℃で、1時間撹拌され、撹拌の間に2gの無水酪酸が添
加された。次いで、混合物は、TLCによってエステル
化反応の完了が示されるまで、50〜55℃に加熱され
た。上部のキシレン層が分けられ、それに、2.5gの
1−オクチル−2−ピロリドンが添加された。キシレン
および水が、真空下で共沸的に除去された。6.6gの
残留物が得られた。EXAMPLES Example 1 Preparation of di-n-butyl ester of o-cresolphthalein 10 equipped with a stirrer, thermocouple and condenser
The following starting materials were added to a 0 mL three neck round bottom flask: (1) o-cresolphthalein, 1.73 g
(0.005 mol); (2) water, 30 mL; (3) 50
% NaOH, 0.8 g; (4) Na 2 CO 3 , 0.6
g; and (5) xylene, 8 g. The mixture is 20-25
Stirred at 1 ° C. for 1 hour, during which 2 g of butyric anhydride was added. The mixture was then heated to 50-55 C until TLC indicated that the esterification reaction was complete. The upper xylene layer was separated and to it was added 2.5 g of 1-octyl-2-pyrrolidone. Xylene and water were removed azeotropically under vacuum. 6.6 g of residue were obtained.
【0009】キシレン(100mL)に前記残留物10
0mgを溶解し、該残留物溶液の1mLをケロシンで1
00mLにして10ppm溶液を作成することにより、
マーカー溶液が調製された。顕色剤はメタノール中のベ
ンジルトリメチルアンモニウムヒドロキシドの40%溶
液1gを、99gの2−エチル−1−ヘキサノール中に
溶解することにより作成された。上述のように調製され
た10ppmのマーカー溶液の10mLに、顕色剤の
2.5mLが添加された。混合物は、数秒間振とうされ
た後に、青−紫色となった。所望の場合には、マーカー
濃度の定量的決定は、581nmの波長で該溶液の吸光
度を測定することによって成されることができる。上述
のように調製された10ppm溶液の10mLが、10
mLの水と共に、1/2時間撹拌され、層が分けられ
た。2mLの顕色剤溶液が有機層に添加され、青−紫色
の発色が生じた。2mLの発色剤溶液を水層に添加して
も発色しなかった。このことは、該マーカーが水層に抽
出されなかったことを示す。The residue 10 is dissolved in xylene (100 mL).
0 mg, dissolve 1 mL of the residue solution with kerosene
By making 10 mL solution to make 00 mL,
A marker solution was prepared. The developer was made by dissolving 1 g of a 40% solution of benzyltrimethylammonium hydroxide in methanol in 99 g of 2-ethyl-1-hexanol. To 10 mL of the 10 ppm marker solution prepared as described above, 2.5 mL of the developer was added. The mixture turned blue-purple after shaking for a few seconds. If desired, a quantitative determination of the marker concentration can be made by measuring the absorbance of the solution at a wavelength of 581 nm. 10 mL of the 10 ppm solution prepared as described above
Stirred with mL of water for 1/2 hour and separated the layers. 2 mL of the developer solution was added to the organic layer and a blue-purple color developed. No color was formed even when 2 mL of the color former solution was added to the aqueous layer. This indicates that the marker was not extracted in the aqueous layer.
───────────────────────────────────────────────────── フロントページの続き Fターム(参考) 4C037 RA02 4H013 CE03 CE05 4H056 BA02 BB01 BB14 BC01 BD01 BF08 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C037 RA02 4H013 CE03 CE05 4H056 BA02 BB01 BB14 BC01 BD01 BF08
Claims (10)
ルケニル、アリールまたはアルアルキルであり;R2、
R3およびR4は独立して、水素、C1−C12アルキ
ル、クロロまたはブロモであり;さらにR5は水素、ク
ロロまたはブロモである。〕を有する化合物を含む組成
物であって、該化合物が視覚的に検出可能でない量で存
在する前記組成物。1. A liquid petroleum product and formula [In the formulas, R 1 is C 1 -C 18 alkyl, C 1 -C 18 alkenyl, aryl or aralkyl; R 2,
R 3 and R 4 are independently hydrogen, C 1 -C 12 alkyl, chloro or bromo; and R 5 is hydrogen, chloro or bromo. Wherein the compound is present in an amount that is not visually detectable.
mの量で存在する、請求項1記載の組成物。2. The method according to claim 1, wherein the compound is 0.5 ppm to 100 pp.
The composition of claim 1, wherein the composition is present in an amount of m.
料、ジェット燃料、燃料油、ケロシンまたは灯油である
請求項2記載の組成物。3. The composition according to claim 2, wherein the liquid petroleum product is gasoline, diesel fuel, jet fuel, fuel oil, kerosene or kerosene.
〜4個の炭素原子を有するアルキルである請求項3記載
の組成物。4. R 2 , R 3 and R 4 are hydrogen, or 1
The composition of claim 3 which is an alkyl having from 4 to 4 carbon atoms.
キルであり、R5が水素である請求項4記載の組成物。5. The composition according to claim 4, wherein R 1 is alkyl having 1 to 4 carbon atoms and R 5 is hydrogen.
ルケニル、アリールまたはアルアルキルであり;R2、
R3およびR4は独立して、水素、C1−C12アルキ
ル、クロロまたはブロモであり;さらにR5は水素、ク
ロロまたはブロモである。〕の化合物をマーカーとして
石油製品に添加し、該化合物は視覚的に検出可能ではな
く、さらに該化合物は顕色剤と接触して発色することを
含む、液体石油製品をマーキングする方法。7. A compound of the formula [In the formulas, R 1 is C 1 -C 18 alkyl, C 1 -C 18 alkenyl, aryl or aralkyl; R 2,
R 3 and R 4 are independently hydrogen, C 1 -C 12 alkyl, chloro or bromo; and R 5 is hydrogen, chloro or bromo. A method for marking a liquid petroleum product, comprising adding the compound of the formula (1) as a marker to a petroleum product, wherein the compound is not visually detectable, and the compound is colored by contact with a developer.
mの量で存在する請求項7記載の方法。8. The method according to claim 1, wherein the compound is 0.5 ppm to 100 pp.
8. The method of claim 7, wherein the method is present in an amount of m.
料、ジェット燃料、燃料油、ケロシンまたは灯油である
請求項8記載の方法。9. The method according to claim 8, wherein the liquid petroleum product is gasoline, diesel fuel, jet fuel, fuel oil, kerosene or kerosene.
1〜4個の炭素原子を有するアルキルであり、R1が1
〜4個の炭素原子を有するアルキルであり、R 5が水素
である請求項9記載の方法。10. R2, R3And R4Is hydrogen, or
Alkyl having 1-4 carbon atoms, R1Is 1
Alkyl having up to 4 carbon atoms; 5Is hydrogen
The method according to claim 9, wherein
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23550000P | 2000-09-26 | 2000-09-26 | |
US60/235500 | 2000-09-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2002146371A true JP2002146371A (en) | 2002-05-22 |
Family
ID=22885760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2001284464A Withdrawn JP2002146371A (en) | 2000-09-26 | 2001-09-19 | Colorless petroleum marker dye |
Country Status (5)
Country | Link |
---|---|
US (1) | US20020038064A1 (en) |
EP (1) | EP1191084A2 (en) |
JP (1) | JP2002146371A (en) |
KR (1) | KR20020024783A (en) |
BR (1) | BR0104274A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007037586A1 (en) * | 2005-08-22 | 2007-04-05 | Hyun-Ho Sim | Fluorescent marker comprising double bond ester group and method for marking and detecting the same |
JP2015522035A (en) * | 2012-07-06 | 2015-08-03 | ダウ グローバル テクノロジーズ エルエルシー | Tritylated alkyl aryl ether |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6482651B1 (en) * | 1999-06-30 | 2002-11-19 | United Color Manufacturing, Inc. | Aromatic esters for marking or tagging petroleum products |
KR100398506B1 (en) * | 2001-06-13 | 2003-09-19 | 오리엔트화학 (주) | Marker for idetification curable silicone composition having slip property |
US7910531B2 (en) * | 2004-06-17 | 2011-03-22 | C2C Technologies Llc | Composition and method for producing colored bubbles |
US20060257439A1 (en) * | 2005-03-29 | 2006-11-16 | Sabnis Ram W | Cleansing compositions with color changing indicator |
US20060222675A1 (en) * | 2005-03-29 | 2006-10-05 | Sabnis Ram W | Personal care compositions with color changing indicator |
US20060236470A1 (en) * | 2005-03-29 | 2006-10-26 | Sabnis Ram W | Novelty compositions with color changing indicator |
US20060222601A1 (en) * | 2005-03-29 | 2006-10-05 | Sabnis Ram W | Oral care compositions with color changing indicator |
US20070010400A1 (en) * | 2005-07-06 | 2007-01-11 | Sabnis Ram W | Use of color changing indicators in consumer products |
KR100846568B1 (en) * | 2005-09-02 | 2008-07-15 | 심현호 | Lactone marker comprising double bond ester group and method for marking and detecting the same |
KR20060018801A (en) * | 2005-09-02 | 2006-03-02 | 심현호 | Lactone marker comprising double bond ester group and method for markng and detecting the same |
KR102027114B1 (en) * | 2013-08-30 | 2019-10-11 | 에스케이이노베이션 주식회사 | Petroleum Markers and identifying method of petroleum using it |
MX2019002141A (en) * | 2016-08-24 | 2019-08-01 | United Color Mfg Inc | Marker compositions, and methods for making and using same. |
-
2001
- 2001-09-13 EP EP01307809A patent/EP1191084A2/en not_active Withdrawn
- 2001-09-14 KR KR1020010056668A patent/KR20020024783A/en not_active Application Discontinuation
- 2001-09-17 US US09/954,373 patent/US20020038064A1/en not_active Abandoned
- 2001-09-19 JP JP2001284464A patent/JP2002146371A/en not_active Withdrawn
- 2001-09-25 BR BR0104274-2A patent/BR0104274A/en not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007037586A1 (en) * | 2005-08-22 | 2007-04-05 | Hyun-Ho Sim | Fluorescent marker comprising double bond ester group and method for marking and detecting the same |
JP2015522035A (en) * | 2012-07-06 | 2015-08-03 | ダウ グローバル テクノロジーズ エルエルシー | Tritylated alkyl aryl ether |
Also Published As
Publication number | Publication date |
---|---|
EP1191084A2 (en) | 2002-03-27 |
KR20020024783A (en) | 2002-04-01 |
BR0104274A (en) | 2002-06-04 |
US20020038064A1 (en) | 2002-03-28 |
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