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
  • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
  • C10L3/003—Additives for gaseous fuels
  • C10L3/006—Additives for gaseous fuels detectable by the senses

Definitions

• Natural gas for public gas supply is odorized worldwide with sulfur-containing odorants.
• sulfur-containing odorants For example, mercaptans or thiophenes are used. These substances are added to give the almost odorless natural gas a warning smell.
• the substances used up to now are very suitable for odorization, their combustion still releases sulfur dioxide, which pollutes the environment.
• odorized natural gas decentrally for catalytic processes for example for use in fuel cells.
• the object of the present invention was to find an odorant for town gas which meets the above-mentioned basic requirements and has a low tendency to adsorb the odorant on pipe walls and in the ground.
• the object is achieved by a mixture of at least two components, one of the components being norbomene or a norbornene derivative and one component being a diluent.
• the odorant for gas contains norbornene or a norbornene derivative, a diluent and another substance. It has surprisingly been found that the mixtures according to the invention meet all requirements. In particular, the new odorant has excellent adsorption properties due to the non-polar nature of the norbomene.
• Pure norbomene is less suitable as an odorant because it is solid at room temperature (melting point: 45 ° C).
• An important requirement for odorants, however, is that the cloud point be at a temperature of -30 ° C or below.
• the cloud point is the temperature at which a liquid odorant can visually observe a cloudiness due to solidification of the melt or the failure of a component.
• the diluent therefore lowers the cloud point of the norbomene or the norbornene derivative. Mixtures of norbomene or norbomene derivatives with diluents meet all requirements.
• the norbomene derivatives which can be used according to the invention are generally compounds which contain a norbomene or norbornane skeleton, but the basic skeleton of the bicyclus must not contain any heteroatoms.
• Norbomene derivatives such as norbomene carboxylic acids, alcohols derived from norbomene, but in particular non-polar norbomene derivatives, can be used advantageously.
• This Norbomene derivatives can be norbomene or norbomadiene, its derivatives, norbomene and norbomadiene derivatives substituted by alkyl or aryl groups, in particular norbomene derivatives, which can be prepared by Diels-Alder reaction of cyclopentadiene or cyclopentadiene derivatives, in particular pentamethylcyclopentadiene and unsaturated hydrocarbons, for example 1 2,3,4,7-pentamethylnorbomene, 5-ethylidene-2-norbornene and 5-vinyl-2-norbomene.
• Saturated compounds which contain a norbomane skeleton such as, for example, camphane-bornan and also fenchane terpenes and trinorbornane and compounds derived therefrom, can also be used as norbomene derivatives.
• the suitable norbomene derivatives are generally known and are described, for example, in: Beilstein E IV 5: 394; Blechert, sympatheticen aus Chemie,technik und Laboratorium, 28 (1980) 724-726; Buchbauer, Popp, Chemiker-Zeitung 107 (1983) 327-339; Burkert, Angew. Chem.
• diluents should have an evaporation behavior similar to that of norbomene; Compounds which form azeotropes or azeotrope-like compositions with norbomene are therefore particularly suitable.
• Suitable diluents are, in particular, aliphatic and aromatic hydrocarbons such as petroleum ether, gasoline, light petrol, methane, ethane, propane, butane, isobutane, and linear and branched hydrocarbons with 5 to 10 carbon atoms, or also benzene, toluene, xylenes, ethylbenzene and diethylbenzene and in general Substituted benzene derivatives, especially benzene derivatives, which are substituted with alkyl radicals containing 1 to 4 carbon atoms.
• esters in particular formic acid esters, acetic acid esters, propionic acid esters, butanoic acid esters and valeric acid esters, in particular the esters with short-chain aliphatic alcohols such as methanol, ethanol, propanol or butanol, such as, for example, methyl formate and ethyl ester, and ethyl acetate.
• Linear and cyclic ethers are also suitable, such as, for example, tetrahydrofuran, dioxane and isopropyl methyl ether.
• Preferred diluents for use with norbornene are ethyl acetate and Ethyl propionate, particularly preferred are aliphatic ethers, in particular tetrahydrofuran, very particularly preferred are hydrocarbons such as aromatic hydrocarbons, toluene and xylene, in particular aliphatic hydrocarbons, of which pentane, hexane, heptane, and their isomers and petroleum ether are particularly preferred.
• Petroleum ether is generally a mixture of various low-boiling (about 50 to 70 ° C) hydrocarbons. The diluents can be used individually or as a mixture.
• the diluents must be at least partially miscible with norbomene and have a boiling point at normal pressure of 20 ° C to 200 ° C.
• the diluents are used in a concentration range from 10 percent by weight to 80 percent by weight, preferably from 20 to 50 percent by weight.
• norbomene is soluble in the diluent and the odorant according to the invention is a solution of norbomene in the diluent.
• the cloud points of the mixtures according to the invention are at least ⁇ 30 ° C., advantageously ⁇ 40 ° C., in particular ⁇ 41 ° C. or lower temperatures.
• concentration range of the further additives is in the range from 0.01 to 10 percent by weight, preferably in the range from 0.1 to 5 percent by weight. Further preferred configurations can be found in the claims
• Petroleum ether (boiling range 80 - 100 ° C): 35 percent by weight

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• 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)
• Crystals, And After-Treatments Of Crystals (AREA)
• Liquid Carbonaceous Fuels (AREA)

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• 2000
  • 2000-11-27 DE DE10058805A patent/DE10058805A1/de not_active Withdrawn
• 2001
  • 2001-10-29 DE DE50112348T patent/DE50112348D1/de not_active Expired - Lifetime
  • 2001-10-29 AT AT01997533T patent/ATE359348T1/de not_active IP Right Cessation
  • 2001-10-29 AU AU2002219065A patent/AU2002219065A1/en not_active Abandoned
  • 2001-10-29 EP EP01997533A patent/EP1381659B1/fr not_active Expired - Lifetime
  • 2001-10-29 RU RU2003119082/04A patent/RU2267519C2/ru not_active IP Right Cessation
  • 2001-10-29 WO PCT/EP2001/012472 patent/WO2002042396A2/fr active IP Right Grant
  • 2001-10-29 US US10/433,240 patent/US20050258402A1/en active Pending

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