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WO1999060077A1 - Formulation liquide d'hydrocarbures - Google Patents

Formulation liquide d'hydrocarbures Download PDF

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Publication number
WO1999060077A1
WO1999060077A1 PCT/GB1999/001523 GB9901523W WO9960077A1 WO 1999060077 A1 WO1999060077 A1 WO 1999060077A1 GB 9901523 W GB9901523 W GB 9901523W WO 9960077 A1 WO9960077 A1 WO 9960077A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid
stabiliser
aliphatic hydrocarbon
agent
hydrocarbon
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.)
Ceased
Application number
PCT/GB1999/001523
Other languages
English (en)
Inventor
Bernd Renner
Ulrich Schmidt
Cameron James SMITH
Philip Gerald TAYLOR
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.)
Macfarlan Smith Ltd
Original Assignee
Macfarlan Smith Ltd
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 Macfarlan Smith Ltd filed Critical Macfarlan Smith Ltd
Priority to EP99922304A priority Critical patent/EP1080165B1/fr
Priority to GB0030498A priority patent/GB2354255B/en
Priority to AU39411/99A priority patent/AU745819B2/en
Priority to JP2000549686A priority patent/JP2002515536A/ja
Priority to DE1999614323 priority patent/DE69914323T2/de
Publication of WO1999060077A1 publication Critical patent/WO1999060077A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • C10L1/1857—Aldehydes; Ketones
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides

Definitions

  • This invention relates to a denaturant formulation suitable for discouraging the ingestion of hydrocarbon liquids particularly paraffinic liquids such as lamp oil, white spirit, kerosene and other hydrocarbon solvents.
  • Liquid hydrocarbons are widely used for various technical purposes and are often available for household purposes, where unguarded use or storage may present risks to children and domestic animals who may confuse them with potable liquids. This is especially so in third world countries where near starving children will consume virtually any liquid in their desperation to quench a thirst.
  • the inadvertent consumption of such liquids by vulnerable individuals is also a high risk because they are available as essentially colourless transparent liquids which are visually indistinguishable from water.
  • the physiological damage arising from deliberate or inadvertent consumption of these liquids is serious and may be fatal.
  • Aversive agents are known which impart a highly bitter taste to substances when mixed therewith. These cause such a bitter taste if an attempt is made to swallow the substance that the substance is rejected immediately, which usually avoids absorption or ingestion of amounts having any lasting harmful effect.
  • Denatonium benzoate otherwise known as lignocaine benzyl benzoate is cited in the Guinness Book of Records as the most bitter substance known to man, and its preparation and properties are described in GB-A-955 309. It is available commercially under the Registered Trade Mark “BITREX” .
  • Other denatonium salts are known in the literature.
  • Denatonium saccharide is a bittering agent analogous to denatonium benzoate and is described in US-A-4 652 577.
  • Liquid hydrocarbons of the type of concern here are predominantly organic liquids of an aliphatic character (alkanes) and mainly recognisable as of the liquid paraffin type but the invention is not restricted to a particular petroleum distillate fraction commonly called paraffin oil.
  • the problem may be explained more generally by an understanding that aliphatic liquids are useful because of their relative chemical inertness. This, for example, makes white spirit useful as a diluent in enamel paints or as a cleaning liquid for removal of certain paints from surfaces without chemically attacking the surface.
  • This predictable non-reactive character and stability whilst providing desirable properties for marketing products based on such liquids, also presents a problem when seeking to include a denaturant or aversive agent therein.
  • denatonium benzoate is extremely insoluble in apolar liquids. Therefore even though that denaturant would exhibit an acceptable level of aversive activity at concentrations as low as 10 ppm it has not proved possible to introduce it directly to liquid hydrocarbons and maintain a satisfactory level of concentration therein for a sufficient period of time even to satisfy a typical shelf life before eventual use. As cited in GB-B-2 212 814, the denaturant does not form a stable solution in kerosine or the like liquids and tends to migrate rapidly to the container walls.
  • this objective is achievable by utilising a stabiliser in the form of a co- solvent which is at least miscible with the target hydrocarbon but insoluble in water and has sufficient affinity with the selected aversion agent (preferably denatonium benzoate) to permit introduction of effective amounts thereof to the target hydrocarbon with satisfactory stability of the final formulation.
  • a stabiliser in the form of a co- solvent which is at least miscible with the target hydrocarbon but insoluble in water and has sufficient affinity with the selected aversion agent (preferably denatonium benzoate) to permit introduction of effective amounts thereof to the target hydrocarbon with satisfactory stability of the final formulation.
  • Suitable co-solvents for the purposes of the invention include certain aliphatic or alicyclic alkanols, including diols and diol mono-ethers, esters, and mixtures thereof.
  • a preliminary screening test to confirm or determine suitability of a co-solvent from amongst these classes of solvents would include determining if the solvent under consideration is miscible with the hydrocarbon to be denatured and if it is also capable of dissolving the desired denaturant at a satisfactory level, say 0.1%. Preliminary work suggests that substituted alkanols would be acceptable.
  • a method for rendering a liquid hydrocarbon unpalatable with an aversive agent having poor solubility in said liquid hydrocarbon comprising selecting a stabiliser in the form of a co-solvent from amongst aliphatic or alicyclic alkanols and diols, optionally substituted, with ester, ether, ketonic, alicyclic and/or aromatic groups, singularly or as mixtures, said co-solvent being miscible with the liquid hydrocarbon to be denatured and being a solvent in which the aversive agent is soluble, dissolving the aversive agent in the co-solvent and introducing an effective amount of the solution into the liquid hydrocarbon.
  • Preferred stabilisers include diols and diol mono-ethers, esters, and mixtures thereof particularly branched chain lower secondary alkanol esters of lower fatty acids, especially those formed using a secondary diol.
  • An especially suitable co-solvent is 2 , 2 , 4-trimethylpentan-l , 3-diol-monoisobutanoate (CAS-Nr.: 25265-77-4, C ⁇ 2 H 24 0 3 ) which proved to be uniquely suitable for the purpose of the invention.
  • Alkanols which have not been derivatised have also been observed to be useful for the purposes of the invention with varying degrees of stability.
  • aliphatic or alicyclic alkanols i.e. C 2 -C 20 and above such as 1-butanol and isopropanol
  • a base oil to be denatured is selected, a preferred denaturant such as the aversive agent denatonium benzoate is provided, a stabilising co-solvent therefor is selected from amongst alkanols and aliphatic esters of the aforesaid type, the denaturant is introduced to the co-solvent and dissolved therein e.g. by stirring or similar agitation, to provide a doping medium and thereafter an amount of said doping medium sufficient to have an aversive organoleptic effect is added to the base oil to denature same.
  • a preferred denaturant such as the aversive agent denatonium benzoate
  • a stabilising co-solvent therefor is selected from amongst alkanols and aliphatic esters of the aforesaid type
  • Table I The successful co-solvent in Table I is commercially available under the trade mark TEXANOL® from Eastman Chemical Company (USA) .

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)

Abstract

On rend un hydrocarbure liquide désagréable au goût par introduction dans cet hydrocarbure d'un agent dénaturant servant à décourager l'ingestion de cet hydrocarbure liquide, ce qui a jusqu'à maintenant présenté des difficultés, en particulier, en ce qui concerne des liquides paraffiniques, tels que le pétrole lampant, le white spirit, le kérosène et d'autres solvants d'hydrocarbures. Cet agent dénaturant est un composé de denatonium, de préférence, du benzoate de denatonium ou un de ses analogues ou dérivés exerçant des effets organoleptiques similaires, avec lequel on utilise une quantité suffisante d'un stabilisant liquide miscible avec ledit hydrocarbure liquide, par exemple, un alcanol ou un de ses dérivés, afin d'obtenir une solution stable ou une suspension dudit agent dénaturant dans ledit hydrocarbure liquide.
PCT/GB1999/001523 1998-05-15 1999-05-13 Formulation liquide d'hydrocarbures Ceased WO1999060077A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP99922304A EP1080165B1 (fr) 1998-05-15 1999-05-13 Formulation liquide d'hydrocarbures
GB0030498A GB2354255B (en) 1998-05-15 1999-05-13 Hydrocarbon liquid formulation
AU39411/99A AU745819B2 (en) 1998-05-15 1999-05-13 Hydrocarbon liquid formulation
JP2000549686A JP2002515536A (ja) 1998-05-15 1999-05-13 炭化水素液体調合物
DE1999614323 DE69914323T2 (de) 1998-05-15 1999-05-13 Kohlenwasserstoffflüssigkeitsformulierung

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9810408.6A GB9810408D0 (en) 1998-05-15 1998-05-15 Hydrocarbon liquid formulation
GB9810408.6 1998-05-15

Publications (1)

Publication Number Publication Date
WO1999060077A1 true WO1999060077A1 (fr) 1999-11-25

Family

ID=10832084

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1999/001523 Ceased WO1999060077A1 (fr) 1998-05-15 1999-05-13 Formulation liquide d'hydrocarbures

Country Status (9)

Country Link
EP (1) EP1080165B1 (fr)
JP (1) JP2002515536A (fr)
AR (1) AR015299A1 (fr)
AU (1) AU745819B2 (fr)
DE (1) DE69914323T2 (fr)
ES (1) ES2213368T3 (fr)
GB (2) GB9810408D0 (fr)
WO (1) WO1999060077A1 (fr)
ZA (1) ZA200006574B (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB866605A (en) * 1960-02-27 1961-04-26 T & H Smith Ltd Denaturing of potable alcoholic liquids
GB955309A (en) * 1959-11-20 1964-04-15 Edinburgh Pharmaceutical Ind L New quaternary salts and compositions containing them
US4005038A (en) * 1974-04-15 1977-01-25 Peerless Paint And Varnish Corporation Paint composition containing denatonium benzoate or lignocaine benzyl octanoate with a latex resin binder for application over old paint films to prevent ingestion of poisons therefrom
US4084939A (en) * 1976-12-22 1978-04-18 Colgate-Palmolive Company Audibly burning gelled alcohol
EP0318262A1 (fr) * 1987-11-24 1989-05-31 Glaxo Group Limited Compositions
DE19605162C1 (de) * 1996-02-13 1997-09-18 Elf Oil Deutschland Gmbh Synthetisches Schmieröl und dessen Verwendung
EP0884377A2 (fr) * 1997-06-09 1998-12-16 Shell Internationale Researchmaatschappij B.V. Composition de LPF

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2668420B2 (ja) * 1988-11-07 1997-10-27 新高化学工業株式会社 誤食防止性能を有する固形燃料
JP3724043B2 (ja) * 1995-03-30 2005-12-07 ぺんてる株式会社 描画材組成物
CN1048751C (zh) * 1996-05-29 2000-01-26 鲜京工业股份有限公司 含有苦味剂的气体组合物
GB9624070D0 (en) * 1996-11-20 1997-01-08 Rolls Royce Plc Control system for a ducted fan gas turbine engine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB955309A (en) * 1959-11-20 1964-04-15 Edinburgh Pharmaceutical Ind L New quaternary salts and compositions containing them
GB866605A (en) * 1960-02-27 1961-04-26 T & H Smith Ltd Denaturing of potable alcoholic liquids
US4005038A (en) * 1974-04-15 1977-01-25 Peerless Paint And Varnish Corporation Paint composition containing denatonium benzoate or lignocaine benzyl octanoate with a latex resin binder for application over old paint films to prevent ingestion of poisons therefrom
US4084939A (en) * 1976-12-22 1978-04-18 Colgate-Palmolive Company Audibly burning gelled alcohol
EP0318262A1 (fr) * 1987-11-24 1989-05-31 Glaxo Group Limited Compositions
DE19605162C1 (de) * 1996-02-13 1997-09-18 Elf Oil Deutschland Gmbh Synthetisches Schmieröl und dessen Verwendung
EP0884377A2 (fr) * 1997-06-09 1998-12-16 Shell Internationale Researchmaatschappij B.V. Composition de LPF

Also Published As

Publication number Publication date
ZA200006574B (en) 2001-10-15
EP1080165B1 (fr) 2004-01-21
EP1080165A1 (fr) 2001-03-07
DE69914323T2 (de) 2004-11-18
GB9810408D0 (en) 1998-07-15
AU3941199A (en) 1999-12-06
JP2002515536A (ja) 2002-05-28
GB2354255B (en) 2002-10-23
AR015299A1 (es) 2001-04-18
AU745819B2 (en) 2002-04-11
GB2354255A8 (en) 2003-08-07
GB0030498D0 (en) 2001-01-31
GB2354255A (en) 2001-03-21
ES2213368T3 (es) 2004-08-16
DE69914323D1 (de) 2004-02-26

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