US3886287A - Cosmetics containing saturated, branched synthetic higher hydrocarbon - Google Patents

Cosmetics containing saturated, branched synthetic higher hydrocarbon Download PDF

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Publication number
US3886287A
US3886287A US363372A US36337273A US3886287A US 3886287 A US3886287 A US 3886287A US 363372 A US363372 A US 363372A US 36337273 A US36337273 A US 36337273A US 3886287 A US3886287 A US 3886287A
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United States
Prior art keywords
eicosane
trimethylbutyl
trimethyl
octyl
ethyl
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Expired - Lifetime
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US363372A
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English (en)
Inventor
Susumu Kobayashi
Kenichi Tomita
Hakuji Katsura
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Shiseido Co Ltd
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Shiseido Co Ltd
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C9/00—Aliphatic saturated hydrocarbons
    • C07C9/22—Aliphatic saturated hydrocarbons with more than fifteen carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks

Definitions

  • the present invention relates to cosmetics, more par ticularly, relates to cosmetics containing as a cosmetic base, a synthetic higher hydrocarbon having excellent physiological properties.
  • the conventional cosmetic contain a cosmetic base consisting of saturated higher hydrocarbons selected from higher mineral hydrocarbons, for example, liquid paraffins, higher animal hydrocarbons, for example, squalane which is prepared by completely hydrogenating squalene obtained from fish liver oil, and higher vegetable hydrocarbons, for instance, completely hydrogenated terpenes and polymerized terpenes.
  • higher mineral hydrocarbons for example, liquid paraffins
  • animal hydrocarbons for example, squalane which is prepared by completely hydrogenating squalene obtained from fish liver oil
  • higher vegetable hydrocarbons for instance, completely hydrogenated terpenes and polymerized terpenes.
  • the liquid mineral paraffins consist of a mixture of multiple component hydrocarbons, varying in molecular weight and chemical structure. Sometimes, some of the component hydrocarbons stimulate human skin and are easily decomposed by the action of microorganisms. Accordingly, the liquid paraffins guarantee little in cosmetic quality, that is, they neither ensure non-irritation to human skin nor stability during prolonged storage.
  • the vegetable hydrocarbons also include a plurality of component hydrocarbons varying in number of carbon atoms and chemical structure. Therefore, the vegetable hydrocarbons sometimes include undesirable component hydrocarbons having considerable stimulating effect on human skin and low resistance to toggle-organisms.
  • squalane is a simple higher animal hydrocarbon of 30 carbon atoms and does not stimulate human skin and has an excellent stability in storage.
  • the squalane is prepared from squalene include in fish liver oil which is not always readily available, the supply of squalane is limited and variable in quantity.
  • One object of the present invention is to provide cosmetics comprising, as a cosmetic base, a synthetic higher hydrocarbon having a non-stimulative property, a high stability to the action of micro-organisms, and other physiological properties.
  • the other object of the present invention is to provide cosmetics, for example, skin, hair, make-up, bath and toilet cosmetics, comprising a cosmetic base effective for protecting the human body from the action of micro-organisms, with sufficient safety.
  • the above-stated objects are accomplished by the cosmetics of the present invention.
  • the cosmetics of the present invention comprise a base consisting of at least one saturated, branched synthetic higher hydrocarbon having 26 to 48 carbon atoms, of the formula:
  • R,, R R and R represent an alkyl radical of 2 to 15 carbon atoms, but R, differs from R, and R, differs from R and other cosmetic additives.
  • the synthetic higher hydrocarbons usable for the present invention are ideal for the cosmetic base.
  • the synthetic higher hydrocarbons of the present invention can eliminate the above-mentioned drawbacks of the conventional cosmetic base, and be stored for a prolonged period without deterioration. Also, the synthetic higher hydrocarbons of the present invention are greatly effective for protecting human skin from chemical and physical stimulation, preventing the penetration of micro-organisms into the human body, and maintaining human skin in a normal physiological condition even if circumstance changes.
  • Table 1 indicates physical properties of the typical synthetic higher hydrocarbons usable for the present invention. Further, Table 1 shows the physical properties of the synthetic hydrocarbons of less than 26 carbon atoms and squalane. namely, 2,6,10,15,19,23- hexamethyl-tetracosane.
  • the synthetic higher hydrocarbons usable for the present invention include 26 to 48 carbon atoms.
  • the hydrocarbons of less than 26 carbon atoms are not to be considered for the cosmetic base because of too low viscosity and excessive stimulation to human skin.
  • the hydrocarbons having more than 48 carbon atoms are unsuitable for use as cosmetic base because of excessive viscosity and poor spreadability.
  • the synthetic higher hydrocarbons usable for the present invention may be prepared by the conventional methods for synthesizing alkane compounds.
  • the synthetic higher hydrocarbons may be prepared in accordance with the Wurtz reaction or Frankland reaction. That is, two saturated branched hydrocarbon halides of the formula:
  • cacn x and xcn ca 1.
  • 2,2,4-trimethyl-lO ethyl-7( l,3,3-trimethylbutyl)tetradecane and 2,2,4,13,15,]5-hexamethyl-7,l0-bis(1,3,3- trimethylbutyl)hexadecane The above mentioned hydrocarbon compounds were prepared by condensing Z-ethylexyl bromide and 5,7,7- trimethyl 2(l,3,3-trimethyl-butyl)octyl bromide.
  • the lethylhexene-Z-al-l was prepared by condensing n'butylaldehyde in an aqueous solution of 2% by weight of sodium hydroxide, and then, converted to 2' ethylhexanol by hydrogenating in the presence of a raney nickel catalyst.
  • a mixture of one mol of Z ethylhexanol and 2.1 mols of hydrobromic acid (which was an aqueous solution of more than 47% of hydrobromic acid, having a specific gravity of 1.48) was charged into a one litre, three neck flask, and then, 1 part by mol of concentrated sulfuric acid was added by drops while the flask contents were being cooled with ice.
  • reaction mixture was gradually heated while stirring to a temperature of C and maintained at that temperature for 6 hours.
  • the reaction product was diluted with hexane, successively washed with water, concentrated sulfuric acid, water and thereafter, an aqueous solution of sodium carbonate, dried over calcium chloride and then, distilled.
  • the 5,7,7-trimethy1-2( 1,3 ,3-trimethyl-butyl)octy1 bromide was prepared by the following procedure.
  • 3,5,5-trimethy1-hexyl aldehyde was prepared from isooctene by OXO synthesis (hydroformylation) and then, converted to 5,7,7-trimethyl-2(1,3,3-trimethylbutyl) octanol by the aldol condensation process.
  • the 5,7,7-trimethy1-2(1,3,3-trimethyl-butyl) octanol was converted to butyl)octyl bromide having a boiling point of 120 128l2 mml'lg by reacting with the hydrobrornic acid in the same procedure as that of the Z-ethylhexyl bromide, in an yield of 72.7%.
  • the condensation of the 2- ethylhexyl bromide with the 5,7,7-trimethyl-2 (1,3,3-trimethylbutyl)octyl bromide was effected by the following procedure.
  • a 100 ml three neck flask was charged with a reaction mixture of 0.085 mol of the 2-ethylhexyl bromide and 0.085 mol of the 5,7,7-trimethyl-2( 1,3,3-triinethyl butyl)octyl bromide. 0.187 mol of metallic sodium was added to the reaction mixture, which was being cooled with ice and stirred for 5 hours under the cooled condition. The non-reacted metallic sodium was treated with methanol and water. The reaction product was dried with anhydrous sodium sulfate and then distilled to iso' late the resultant hydrocarbon compounds from each other.
  • hydrocarbon compounds (B) and (C) thus obtained are novel compounds of the present invention and have the formulae (1) and (ll).
  • 2-hexyl decanol was prepared from n-octylaldehyde in the same procedure as that of the 2-ethyl hexanol in Example 1.
  • a reaction mixture of 2 mols of the 2- hexyldecanol and 3.mols of pyridine was charged into a 2 litre three neck flask and 2.4 mols of thiony] chloride were added by drops while the mixture was stirred and cooled with ice. After completing the addition of the thionyl chloride, the reaction mixture was heated at a temperature of 120 to 140C for 8 hours.
  • the reaction product was diluted with hexane, successively washed with concentrated sulfuric acid, water and an aqueous solution of sodium carbonate, dried with anhydrous sodium sulfate and then distilled.
  • 2-hexyldecyl chloride with a boiling point of l20 125C/3 mmHg was obtained in an amount of 276 g (yield: 53%).
  • the 2-hexyldecyl chloride in an amount of 0.274 mol was charged into a 200 ml three neck reaction flask, 0.275 mol of metallic sodium was added, while stirring, at room temperature and then maintained at a temperature f l to 140C while stirring for 2 hours. Thereafter, the reaction mixture was heated at a temperature of 130C for 8 hours.
  • the non-reacted metallic sodium was deactivated with ethanol,
  • the reaction product was diluted with hexane, washed with water, dried with anhydrous sodium sulfate and then, distilled.
  • boiling -dihexyl eicosane having 32 carbon atoms, a boiiling point of l 210C/l 2 mmHg, a viscosity at 25C of 31.5 cps, a specific gravity at 19C of 0.8230 and a freezing point of lower than 8.0C was obtained in a yield of 35%.
  • the 9,12-dihexyl eicosane is a novel compound of the present invention and has the following formula I): cu.
  • the 2-hexyldecyl bromide was prepared from 2 hexyl decanol using the same method as that of 2 ethylhexyl bromide in Example 1. i
  • a 500 ml three neck reaction flask was charged with 0.l mol of metallic magnesium and a small amount of iodine, and a small amount ofthe 2-hexyldecyl bromide was added by drops. Thereafter, a solution of 0.2 mol of the Z-hexyldecyl bromide in 200 ml of anhydrous ether was further added by drops into the reaction flask. The reaction mixture was heated at a tempera ture of 55 65C for 24 hours while refluxing, and
  • a mixture of 2-octyl dodecanol and the sodium salt of n'nonanoic acid was prepared by heating n-decanol at a temperature of 200 to 230C in the presence of sodium hydroxide. From the mixture, 2-octyl dodecanol was isolated by extraction and distillation. The 2-octyl dodecanol thus obtained, was converted to 2- octyldodecyl bromide having a boiling point of 175 185C/3 mml-lg by treating with hydrobromic acid in the same as that for 2-ethyl hexanol in Example 1.
  • the condensation of the 2-octyldodecyl bromide was carried out by heating together with metallic sodium at room temperature for 16 hours, at 55C for 6 hours and then, at 150C for 4 hours.
  • the condensation product was treated in the same method as that for the condensation product in Example I.
  • 1 l ,14-dioctyl tetracosane having 40 carbon atoms, a boiling point of 200 220"C/' mml-lg, a viscosity at 25C, of 52.5 cps, a specific gravity at 19C of 0.8169 and a freezing point of 7.5 105C was obtained in a yield of 74%.
  • the hydrocarbon compound thus prepared has the following formula IV:
  • the lint pieces were covered by 3.5 cm square gauzes secured onto the test portions by adhesive tapes and further completely covered by rubber dams.
  • the rabbits were maintained for 72 hours under the above-mentioned test conditions. After 24 hours the lint pieces on the rabbits were removed and the test portions were observed for red spots (erythemata) and dropsical swellings (edemata). The erythemata and edemata thus observed were valued in accordance with the predetermined evaluation standards as detailed hereinafter. Thereafter, the lint pieces were re-applied for the remaining 48 hours. After the testing was completed, the same evaluation as stated above was repeated.
  • Table 2 clearly shows that the synthetic higher hydrocarbons of the present invention had practically no stimulation of animal skin. This is the same as that of squalane. However, the fluid paraft'me and the comparative hydrocarbons having less than 26 carbon atoms had high stimulation of animal skins.
  • the synthetic higher hydrocarbons of the present invention as shown in Table 2 were further subjected to tests which might indicate stimulation of the mucous membranes of the eyes involving the cornea, iris and conjunctive which were observed at predetermined intervals of time. Also tests were carried out to observe effect on human skin and effects of acute toxicity resulting from ingestion of doses of 25 ml/kg body weight. All the results of the tests were negative. That is, the excellent safety of the synthetic higher hydrocarbons of the present invention was confirmed.
  • culture medium 10 g hydrocarbon compound to be tested 2.5 g K2HPO4 0.5 g KH2PO4 0.3 g MgSO 0.3 g CaCI; 3.0 g (NH SO 0.3 g NaCl 1000 ml water 2.
  • Culture condition 30 ml of culture medium was charged into a ml shaking flask sterilized in an autoclave at a high tem perature, and allowed to cool to room temperature.
  • One platinum loop of the bacterial suspension was inoculated into the culture medium.
  • the inoculated culture medium was shaken at a frequency of l20/minutes at a temperature of 30C for 7 days to culture the bacterium.
  • the multiplication of the bacterial fungus bodies was determined by the method detailed below.
  • the synthetic higher hydrocarbons of the present invention can be utilized as a cosmetic base for the treat ment and make-up products, such as O/W type nutritious cream, W/O type nutritious cream. pomade. lip stick, bath oil, skin lotion, skin moisturizer. eye make up and body lotion
  • the cosmetics are prepared by making the synthetic higher hydrocarbon with the other cosmetic ingredients. for example, cctylalcohol. vaseline, lanoiine, polyoxyethylcne cetylalcohol ether. polyethylene glycol. bees war-1 soibitan monoolealc,
  • the nutritious cream of the present example had cosmetic qualities similar to those of the comparison Cl'CLlr'T l.
  • EXAMPLE 2 A W/G type nutritious cream was prepared by the following procedures.
  • the resulting W/O type nutritious cream had excellent cosmetic properties.
  • EXAMPLE 4 A pomade was prepared by the following method. 9% of 9.12-dihexyl eicosane was mixed with 52% of white vascline. 6% of solid paraffin and 30% of olive oil and the mixture was melted at a temperature of C while stirring. The melt was mixed with a necessary amount of coloring matter. The colored melt was allowed to cool to a temperature of 40 50C and mixed with 3% of a perfume and a necessary amount of an antioxidizing agent while stirring. The mixture was fed into a container and allowed to cool to room temperature.
  • the resulting pomade was found to be satisfactory in cosmetic quality.
  • R R R and R represent an alkyl radical of 2 to carbon atoms respectively, but R differs from R and R differs from R 2.
  • said saturated, branched higher hydrocarbon is selected from the group consisting of 2,2,4-trimethy1-l0-ethy1-7-(1,3,3,- trimethylbutyl)tetradecane, 5-ethy1-8-octyloctadecane, 2,2,4-trimethyl-7-( 1,3,3-trimethylbutyl- )eicosane, 9,12-dihexyl-eicosane, hexaethyl-eicosane, S-ethyl-S-decyl-eicosane, 2,2,4,l 3,15 l S-hexamethyl- 7,l0-bis( 1 ,3,3-trimethylbutyl)hexadecane, 9-hexyl 1 2- octyl-doco
  • a cosmetic composition comprising conventional cosmetic agents, the improvement which comprises employing as a non-irritating cosmetic base of said cosmetic composition at least one saturated,

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US363372A 1972-10-06 1973-05-24 Cosmetics containing saturated, branched synthetic higher hydrocarbon Expired - Lifetime US3886287A (en)

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JP (1) JPS5231022B2 (enrdf_load_stackoverflow)
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FR (1) FR2201863B1 (enrdf_load_stackoverflow)
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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4183917A (en) * 1976-12-25 1980-01-15 The Lion Dentifrice Co., Ltd. Emulsion-type hair conditioner composition
US4784843A (en) * 1985-03-01 1988-11-15 Basf Aktiengesellschaft Dicyclohexylalkanes, their preparation, cosmetic and pharmaceutical formulations containing these compounds, and their use as oil components
US20040202739A1 (en) * 2000-06-27 2004-10-14 Crosby Martin G. Compositions and methods for treating female sexual response
US20070238909A1 (en) * 2006-02-03 2007-10-11 Gadewar Sagar B Continuous process for converting natural gas to liquid hydrocarbons
US20080171898A1 (en) * 2004-04-16 2008-07-17 Waycuilis John J Process for converting gaseous alkanes to liquid hydrocarbons
US20080200740A1 (en) * 2004-04-16 2008-08-21 Marathon Oil Company Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US20090312586A1 (en) * 2008-06-13 2009-12-17 Marathon Gtf Technology, Ltd. Hydrogenation of multi-brominated alkanes
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US7847139B2 (en) 2003-07-15 2010-12-07 Grt, Inc. Hydrocarbon synthesis
US20110015458A1 (en) * 2009-07-15 2011-01-20 Marathon Gtf Technology, Ltd. Conversion of hydrogen bromide to elemental bromine
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US20110218372A1 (en) * 2010-03-02 2011-09-08 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons
FR3041254A1 (fr) * 2015-09-22 2017-03-24 Biosynthis Sarl Ingredient cosmetique a base d'hydrocarbures satures ramifies

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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US4368189A (en) * 1981-08-03 1983-01-11 Eli Lilly And Company Cosmetic moisturizer formulation
US4609545A (en) * 1982-11-24 1986-09-02 Schlossman Mitchell L Compressing aid for compressing powders
GB9405320D0 (en) * 1994-03-18 1994-04-27 Procter & Gamble Powder cosmetic compositions

Citations (1)

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US3069324A (en) * 1959-06-19 1962-12-18 Monot Pierre Louis Victor Hydrogenated tallowperhydrosqualene dermatological excipient

Patent Citations (1)

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US3069324A (en) * 1959-06-19 1962-12-18 Monot Pierre Louis Victor Hydrogenated tallowperhydrosqualene dermatological excipient

Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4183917A (en) * 1976-12-25 1980-01-15 The Lion Dentifrice Co., Ltd. Emulsion-type hair conditioner composition
US4784843A (en) * 1985-03-01 1988-11-15 Basf Aktiengesellschaft Dicyclohexylalkanes, their preparation, cosmetic and pharmaceutical formulations containing these compounds, and their use as oil components
US20040202739A1 (en) * 2000-06-27 2004-10-14 Crosby Martin G. Compositions and methods for treating female sexual response
US8128972B2 (en) 2000-06-27 2012-03-06 Semprae Laboratories, Inc. Compositions and methods for enhancing and treating female sexual response
US7875299B2 (en) * 2000-06-27 2011-01-25 Semprae Laboratories, Inc. Compositions and methods for enhancing or treating female sexual response
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US8415512B2 (en) 2001-06-20 2013-04-09 Grt, Inc. Hydrocarbon conversion process improvements
US7847139B2 (en) 2003-07-15 2010-12-07 Grt, Inc. Hydrocarbon synthesis
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US20080171898A1 (en) * 2004-04-16 2008-07-17 Waycuilis John J Process for converting gaseous alkanes to liquid hydrocarbons
US8008535B2 (en) 2004-04-16 2011-08-30 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US20080183022A1 (en) * 2004-04-16 2008-07-31 Waycuilis John J Process for converting gaseous alkanes to liquid hydrocarbons
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons
US20080200740A1 (en) * 2004-04-16 2008-08-21 Marathon Oil Company Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US8232441B2 (en) 2004-04-16 2012-07-31 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US7880041B2 (en) 2004-04-16 2011-02-01 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7560607B2 (en) 2004-04-16 2009-07-14 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7579510B2 (en) 2006-02-03 2009-08-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8053616B2 (en) 2006-02-03 2011-11-08 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US20070238909A1 (en) * 2006-02-03 2007-10-11 Gadewar Sagar B Continuous process for converting natural gas to liquid hydrocarbons
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US8921625B2 (en) 2007-02-05 2014-12-30 Reaction35, LLC Continuous process for converting natural gas to liquid hydrocarbons
US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US20090312586A1 (en) * 2008-06-13 2009-12-17 Marathon Gtf Technology, Ltd. Hydrogenation of multi-brominated alkanes
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8415517B2 (en) 2008-07-18 2013-04-09 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US20110015458A1 (en) * 2009-07-15 2011-01-20 Marathon Gtf Technology, Ltd. Conversion of hydrogen bromide to elemental bromine
US9133078B2 (en) 2010-03-02 2015-09-15 Gtc Technology Us, Llc Processes and systems for the staged synthesis of alkyl bromides
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US20110218372A1 (en) * 2010-03-02 2011-09-08 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
FR3041254A1 (fr) * 2015-09-22 2017-03-24 Biosynthis Sarl Ingredient cosmetique a base d'hydrocarbures satures ramifies
WO2017050943A1 (fr) * 2015-09-22 2017-03-30 Biosynthis Ingredient cosmetique a base d'hydrocarbures satures ramifies
KR20180054819A (ko) * 2015-09-22 2018-05-24 바이오신디스 분지형 포화 탄화수소 화장 성분
CN108348789A (zh) * 2015-09-22 2018-07-31 碧昂赛恩斯公司 支链饱和烃化妆品成分
EP3744402A1 (fr) 2015-09-22 2020-12-02 Biosynthis Ingredient cosmetique a base d'hydrocarbures satures ramifies
CN108348789B (zh) * 2015-09-22 2021-09-07 碧昂赛恩斯公司 支链饱和烃化妆品成分
US11571372B2 (en) 2015-09-22 2023-02-07 Biosynthis Branched saturated hydrocarbon cosmetic ingredient

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DE2327087A1 (de) 1974-04-25
FR2201863B1 (enrdf_load_stackoverflow) 1977-05-06
GB1379013A (en) 1975-01-02
DE2327087B2 (de) 1975-01-16
DE2327087C3 (enrdf_load_stackoverflow) 1975-08-28
FR2201863A1 (enrdf_load_stackoverflow) 1974-05-03
IT1047476B (it) 1980-09-10
JPS4955853A (enrdf_load_stackoverflow) 1974-05-30
JPS5231022B2 (enrdf_load_stackoverflow) 1977-08-12

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