Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
  • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
  • C10G27/12—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen with oxygen-generating compounds, e.g. per-compounds, chromic acid, chromates
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S585/00—Chemistry of hydrocarbon compounds
  • Y10S585/929—Special chemical considerations
  • Y10S585/947—Terpene manufacture or recovery

Definitions

• ABSTRACT There is provided a process for the upgrading of a malodorous. sulfur-contaminated. aliphatic. aromatic or cycloaliphatic olefinic derivative or mixture thereof which involves contacting said malodorous. sulfurcontaminated derivative or mixture thereof with from 1 to 2 equivalents of a per(lower)alkanoic acid per mole of sulfur in said olefinic derivative. the amount of said acid being sufficient to oxidize the sulfur content therein. maintaining the treated solution at a temperature ranging from about l0C. to about 80C. or
• the present invention relates to a novel process for upgrading sulfur-contaminated olefinie derivatives. More particularly, it relates to a process for upgrading malodorous sulfur-contaminated aliphatic, aromatic or cycloaliphatic olefinic derivatives and mix t'ures'thereof by substantially removing the offensive odor therefrom. Still more particularly,'the invention is concerned with a method for treating said sulfur-contaminated olefinic derivatives or mixtures thereof with an organic peracid defined hereinbelow with particularity in anamount sufficient to obtain storage-stable, odor improved olefinic derivatives.
• the odor of the so-treated olefinic derivative is markedly improved and remains storage-stable with respect to odor over a prolonged period of time, whereas the olefinic derivative remains unaffected notwithstanding the known conversion of olefms to epoxides in the presence of peracids.
• any commercially available sulfur-contaminated olefinic derivative or mixture thereof can be subjected to the action of an organic peracid over a temperature ranging from 10C. to 80C. or higher up" to the decomposition point of the peracid.
• an organic peracid over a temperature ranging from 10C. to 80C. or higher up" to the decomposition point of the peracid.
• the addition of from about one equivalent to not more than two equivalents of an organic peracid per mole of sulfur in said olefinic derivative is sufficient to oxidize the sulfur content therein, thereby reducing any offensive odor therein to a highly commercially acceptable level.
• Such per(lower)-alkanoic acids aswell as their method for preparation are well known in the art.
• from one to two equivalents of said peracid per mole of sulfur in said olefinic derivative is sufficient to oxidize the sulfur content.
• a good operating amount of peracid based on200 to 5,000 ppm. sulfur usually ranges from about 0:1 to about 5.0 percent, and preferably from 0.5 to 2 percent, all by weight of said organic peracid.
• Such amount of peracid, when added to a sulfur contaminated olefinic derivative is sufficient to reduce offensive odors therein to a highly commercially acceptable level. Of course, such amount is dependent upon the overall sulfur content. However, the utilization ofan amount in excess of 5 percent of the peracid when not required to oxidize sulfur is not preferred for the reason that the cost is increased and little, if any, additional advantage either by way of increasing the level or extending the period of odor control is attained.
• EXAMPLE 1 A suitable flask immersed in a water bath at 20C.
• EXAMPLE 2 A suitable flask equipped with a magnetic stirring bar is charged with (a) 100 parts of anethole containing 160 ppm. of sulfur and (b) 1.0 part of 40% aqueous peracetic acid. Resultant mixture is stirred for one hour and then washed with water and subsequently steam distilled, employing the procedure of Example l above, to yield 93 parts of organic distillate of significantly improved odor. On analysis, the distillate exhibited a sulfur content of ppm.
• EXAMPLE 3 A suitable flask, immersed in a water bath and equipped with a stirrer and a thermometer is charged with 100 parts of a particularly foul smelling crude sulfate turpentine containing 4,800 ppm. of sulfur. Stirring is initiated and 7.0 parts of 40% aqueous peracetic acid are slowly added at a rate so as not to exceed a pot temperature of C.
• the resulting mixture is stirred at ambient temperature for one hour and is then washed with water to obtain an odor improved product containing 200 ppm. sulfur. It is next steam distilled as set forth in Example 1, to yield 93 parts of a pleasant smelling distillate which is found to contain 95 ppm. of sulfur.
• EXAMPLE 5 A 100 g. sample of malodorous cyclohexene, containing 5,000 ppm. sulfur present as n-butyl ethyl sulfide, is cooled to 15C. and 4.0 g. of 40% (by weight) peracetic acid is slowly added at a rate so as not to exceed a pot temperature of 25C.
• the resulting mixture is stirred briefly at ambient temperature and is Washed successively with 2 X 100 ml. portions of deionized H 0, 50 ml. of 5% Na CO and finally, an additional 100 ml. of deionized H O.
• the washed material is then steam distilled to yield 90 g. of a pleasant smelling distillate which is found to contain 35 ppm. of sulfur.
• a method for the upgrading of a malodorous, sulfur-contaminated aliphatic, aromatic, or cyclic olefinic derivative or mixture thereof which comprises the steps of: contacting said malodorous sulfur-contaminated olefinic derivative or mixture thereof with between about 0.1 and about 5.0 percent, by weight, of a per(lower)alkanoic acid, at a temperature ranging from minus() 10C. to C., water washing the so-treated olefinic derivative, and thereafter recovering an odorimproved, storage-stable, sulfur-reduced olefin.
• per(lower)alkanoic acid is selected from the group consisting of peracetic, perpropionic, perbutyric and perpentanoic acids.

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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)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Treating Waste Gases (AREA)

Priority Applications (9)

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Publications (1)

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Cited By (6)

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Citations (10)

• 1974
  • 1974-09-23 US US508300A patent/US3909395A/en not_active Expired - Lifetime
• 1975
  • 1975-08-12 CA CA233,343A patent/CA1055520A/en not_active Expired
  • 1975-08-19 GB GB34479/75A patent/GB1518124A/en not_active Expired
  • 1975-09-05 BR BR7505715*A patent/BR7505715A/pt unknown
  • 1975-09-15 DE DE2541055A patent/DE2541055C2/de not_active Expired
  • 1975-09-18 IT IT51399/75A patent/IT1047507B/it active
  • 1975-09-23 ES ES441185A patent/ES441185A1/es not_active Expired
  • 1975-09-23 FR FR7529149A patent/FR2285356A1/fr active Granted
  • 1975-09-23 JP JP50114380A patent/JPS609489B2/ja not_active Expired

Patent Citations (10)

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