Conditions | Yield |
---|---|
With Mesoscopically Assembled SulfatedZirconia Nanoparticles at 49.84℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; | 100% |
With sulfuric acid; trimethyl orthoformate for 10h; Reflux; | 100% |
With ammonium cerium(IV) nitrate at 20℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With methanesulfonic acid at 80℃; | 98% |
With SO3H and NH2+ functional carbon-based solid acid at 100℃; under 760.051 Torr; for 8h; Catalytic behavior; Temperature; Sealed tube; | 95% |
With sulfuric acid at 30℃; Kinetics; |
Conditions | Yield |
---|---|
With hydrogen; ethylenediamine In ethanol; water stereoselective reaction; | 97% |
With ethanol; nickel Hydrogenation; | |
With sodium hypophosphite; Pd/Pb/C In tetrahydrofuran for 19.5833h; Ambient temperature; | 97 % Chromat. |
With palladium diacetate; bis-(1,2-dimethylpropyl)borane 2.) THF, RT, overnight; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sulfuric acid In methanol at 20℃; | 96% |
Conditions | Yield |
---|---|
In methanol; diethyl ether; toluene at 20℃; for 0.5h; | 96% |
In methanol; diethyl ether; toluene at 20℃; for 0.5h; | |
In hexane at 30℃; for 0.166667h; |
Conditions | Yield |
---|---|
In acetonitrile at 120℃; for 0.0833333h; microwave irradiation; | 96% |
Conditions | Yield |
---|---|
With Dowex 50WX8-100 at 70℃; for 24h; | 94% |
oleic anhydride
benzaldehyde dimethyl acetal
Methyl oleate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In chloroform at 61℃; for 4h; Acylation; | 93% |
Conditions | Yield |
---|---|
With aluminium(III) iodide In acetonitrile; benzene for 1h; | 92% |
Conditions | Yield |
---|---|
With Dowex 50WX8-100 at 20℃; for 12h; | 92% |
sodium methylate
1-[(Z)-octadec-9-enoyl]-1,3-dicyclohexylurea
A
Methyl oleate
B
1,3-Dicyclohexylurea
Conditions | Yield |
---|---|
In methanol at 0℃; for 3h; Product distribution; different acylureas, reagent, solvent and reaction temperature; | A 68% B 90% |
Conditions | Yield |
---|---|
With sulfonated carbonized β-cyclodextrin CD-3 at 80℃; under 15001.5 Torr; for 12h; Catalytic behavior; Pressure; Autoclave; | A 90% B n/a |
vanadia at 150℃; for 24h; Product distribution / selectivity; | A 88% B 32% |
With manganese titanate at 200℃; under 37503.8 Torr; for 24h; Mechanism; Reagent/catalyst; Temperature; Flow reactor; | A 87% B 49% |
Conditions | Yield |
---|---|
86% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 21h; Heating; | 72% |
Conditions | Yield |
---|---|
With Dowex 50WX8-100 at 70℃; for 24h; | 70% |
Conditions | Yield |
---|---|
With lithium hydroxide for 48h; Heating; characterization; | 65% |
Conditions | Yield |
---|---|
With diethyl ether | |
In diethyl ether at 5 - 15℃; | 78 mg |
In diethyl ether for 2h; Ambient temperature; | 29.6 g |
Conditions | Yield |
---|---|
With methanol dann Erhitzen des entstandenen Tetramethylammoniumoleats; |
Conditions | Yield |
---|---|
With ethene; nickel at 220℃; |
methanol
cis-Octadecenoic acid
toluene-4-sulfonic acid
Methyl oleate
Conditions | Yield |
---|---|
at 30℃; Rate constant; | |
at 40℃; Rate constant; |
Conditions | Yield |
---|---|
(i) NaI, MeCOEt, (ii) Ph3P, (iii) /BRN= 1236701/, NaOMe, DMF; Multistep reaction; |
methanol
cis-Octadecenoic acid
A
Methyl oleate
B
methyl 10-oxooctadecanoate
C
10-hydroxy stearic acid methyl ester
D
methyl (S)-10-hydroxyoctadecanoate
Conditions | Yield |
---|---|
With hydrogenchloride 1.) 30 deg C, 3 d, Corynebacterium sp. S-401, 2.) r. t., 2 d; Multistep reaction; |
Conditions | Yield |
---|---|
With lithium hydroxide for 48h; Heating; characterization; |
Conditions | Yield |
---|---|
With lithium hydroxide for 48h; Heating; characterization; |
Conditions | Yield |
---|---|
In methanol; benzene for 0.5h; Ambient temperature; Yield given; | |
sulfuric acid In methanol | |
Multi-step reaction with 2 steps 1: chloroform-d1 / Inert atmosphere; Cooling 2: chloroform-d1 / Inert atmosphere; Cooling View Scheme | |
With toluene-4-sulfonic acid In methanol at 70℃; for 2h; Temperature; | |
With methanol In water at 24.84℃; for 4h; Kinetics; Temperature; |
Conditions | Yield |
---|---|
zinc sulfide In methanol at 25℃; Quantum yield; Product distribution; Irradiation; other catalysts, other solvents; | |
In pentane for 0.333333h; Product distribution; Kinetics; Irradiation; at 185 nm, photostationary state at 185, 214, and 229 nm; | 76 % Turnov. |
With 2-hydroxyethanethiol; dinitrogen monoxide; tert-butyl alcohol at 22℃; Product distribution; Equilibrium constant; Kinetics; Further Variations:; absorbed dose of radiation; γ-Irradiation; |
Conditions | Yield |
---|---|
With hydrogen; nickel(II) acetylacetonate; triethylaluminum In cyclohexane at 25℃; under 982.6 Torr; Thermodynamic data; ΔE(excit.); |
Methyl linoleate
A
Methyl oleate
B
methyl (9E)-octadec-9-enoate
C
Methyl stearate
D
cis-12-octadecenoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogen; bis(acetylacetonate)nickel(II); triethylaluminum In cyclohexane at 25℃; under 1197.1 Torr; Product distribution; Rate constant; other fatty acid esters, var. temp. and pressures; |
methyl linoleate
A
methyl petroselinate
B
methyl 6(E)-octadecenoate
C
Methyl oleate
D
methyl (9E)-octadec-9-enoate
E
Methyl stearate
F
trans-methyl 8-octadecenoate
Conditions | Yield |
---|---|
With hydrogen; palladium In ethanol at 24℃; Product distribution; potencial controlled catalytic hydrogenation of other unsaturated fatty acid esters, effects of potential, electrolytes, solvents, double bond distribution; |
Conditions | Yield |
---|---|
Stage #1: Methyl oleate With ozone In dichloromethane at -78℃; Stage #2: With triphenylphosphine In dichloromethane at -78 - 23℃; for 18h; | A 100% B 100% |
With N-methyl-2-indolinone; ozone at 0℃; | A 74% B 96% |
With ozone; acetic acid; zinc 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2, 30 min; Multistep reaction. Yields of byproduct given; |
Methyl oleate
methyl 9,10-dibromostearate
Conditions | Yield |
---|---|
With bromine In chloroform | 100% |
With bromine | |
With bromine at 0℃; | |
With bromine In diethyl ether for 0.25h; | |
With bromine In tetrachloromethane at 0℃; |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 12h; | 100% |
With tert.-butylhydroperoxide; [MoO3(2,2'-bipyridine)] In 1,2-dichloro-ethane at 75℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Time; | 99% |
With formic acid; dihydrogen peroxide at 20℃; | 97% |
Methyl oleate
erythro-9,10-dihydroxyoctadecanoic acid methyl ester
Conditions | Yield |
---|---|
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone; tert-butyl alcohol at 20℃; for 24h; | 100% |
With osmium(VIII) oxide; water; potassium carbonate; potassium hexacyanoferrate(III) In tert-butyl alcohol | 99% |
With cethyltrimethylammonium permanganate In dichloromethane at 20℃; for 100h; | 37% |
Methyl oleate
2,4,4-trimethyl-1-pentyl hypophosphorous acid
10-[hydroxy-(2,4,4-trimethylpentyl)phosphinoyl]octadecanoic acid methyl ester
Conditions | Yield |
---|---|
With di-tert-amyl peroxide at 140℃; for 6h; Inert atmosphere; | 100% |
Methyl oleate
Conditions | Yield |
---|---|
With di-tert-amyl peroxide; hypophosphorous acid at 140℃; for 5h; Inert atmosphere; | 100% |
diiodomethane
Methyl oleate
9,10-methyleneoctadecanoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: Methyl oleate With diethylzinc In hexane; dichloromethane at -5 - 0℃; for 1h; Inert atmosphere; Stage #2: diiodomethane In hexane; dichloromethane at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate In n-heptane at 105℃; for 22h; Inert atmosphere; | 99% |
In hexane at 30℃; for 72h; Corynebacterium sp. S-401; | 16% |
With Candida rugosa lipase at 40℃; under 15.0012 - 30.0024 Torr; for 48h; | |
With Lipozyme IM at 80℃; under 15.0012 - 30.0024 Torr; for 48h; |
Conditions | Yield |
---|---|
With phosphotungstic acid; dihydrogen peroxide In water at 80℃; pH=Ca. 1; Catalytic behavior; Kinetics; Temperature; Reagent/catalyst; chemoselective reaction; | 99% |
With dihydrogen peroxide; magnesium sulfate; methyltrioxorhenium(VII) In tert-butyl alcohol at 25℃; for 24h; | 92% |
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 20℃; for 2h; | 85% |
Methyl oleate
(Z)-9,10-epoxyoctadecanoic acid methyl ester
Conditions | Yield |
---|---|
With formic acid; dihydrogen peroxide In water at 0 - 23℃; for 24h; | 98.8% |
With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide In water; acetonitrile at 25℃; for 4h; | 97% |
With tert.-butylhydroperoxide In decane for 2h; Reflux; | 97% |
Methyl oleate
methyl (Z)-2-((Z)-hexadec-7-en-1-yl)-3-oxoicos-11-enoate
Conditions | Yield |
---|---|
With tributyl-amine; titanium tetrachloride In toluene at -5 - 0℃; for 1h; Inert atmosphere; | 98% |
With tributyl-amine; titanium tetrachloride In toluene at 0 - 5℃; for 1h; Inert atmosphere; | 93% |
With sodium hydride; xylene | |
With sodium hydride In 1,2-dimethoxyethane |
Conditions | Yield |
---|---|
With isopropyl alcohol In hexane at 0℃; for 0.0833333h; Bouveault-Blanc Reduction; Inert atmosphere; | 98% |
With C32H36ClNO2P2Ru; potassium tert-butylate; hydrogen In tetrahydrofuran at 120℃; under 38002.6 Torr; for 20h; Autoclave; Green chemistry; | 98% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 50℃; for 24h; Inert atmosphere; Enzymatic reaction; | 98% |
Conditions | Yield |
---|---|
Stage #1: Methyl oleate With ozone In dichloromethane Stage #2: With dimethylsulfide In dichloromethane | 97% |
With oxygen; ozone; 4-methylmorpholine N-oxide In dichloromethane at 0℃; | 96% |
With oxygen; ozone; 4-methylmorpholine N-oxide In dichloromethane at -78 - 20℃; for 2.41667h; | 93% |
Methyl oleate
phenylphosphinic acid
10-(hydroxyphenylphosphinoyl)octadecanoic acid methyl ester
Conditions | Yield |
---|---|
With di-tert-amyl peroxide at 140℃; for 5h; Inert atmosphere; | 97% |
diiodomethane
Methyl oleate
cis-9,10-methyleneoctadecanoic acid mthyl ester
Conditions | Yield |
---|---|
Stage #1: diiodomethane With 2,4,6-Cl3C6H2OZnEt In dichloromethane at -40℃; Stage #2: Methyl oleate In dichloromethane at 20℃; | 96% |
With copper In 1,2-dimethoxyethane at 80 - 90℃; for 4h; Irradiation; ultrasound; | 20% |
Stage #1: Methyl oleate With diethylzinc In hexane; dichloromethane at -5 - 0℃; Stage #2: diiodomethane In hexane; dichloromethane at 20℃; | |
With diethylzinc In dichloromethane |
Conditions | Yield |
---|---|
With potassium hydroxide at 180 - 185℃; for 6h; Time; | 96% |
methanol
Methyl oleate
carbon monoxide
dimethyl 1,19-nonadecandioate
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); methanesulfonic acid; 1,2-bis[di(t-butyl)phosphinomethyl]benzene at 80℃; under 22502.3 Torr; for 22h; Autoclave; Inert atmosphere; | 95% |
With methanesulfonic acid; palladium diacetate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene at 90℃; under 15001.5 Torr; for 22h; | 86% |
With 1,2-bis{(di-tert-butylphosphino)methyl}benzene palladium ditriflate at 90℃; under 15001.5 Torr; for 90h; Glovebox; Schlenk technique; Inert atmosphere; | 85% |
1,1,1,4,4,4-hexafluoro-2(Z)-butene
Methyl oleate
B
(Z)-1,1,1-trifluoro-2-undecene
Conditions | Yield |
---|---|
With C47H71ClMoN2O In benzene at 22℃; for 4h; Glovebox; Inert atmosphere; stereoselective reaction; | A 95% B 67% |
With C52H73ClMoN2O In benzene at 22℃; for 0.25h; Inert atmosphere; Glovebox; | A 95% B 67% |
Methyl oleate
1-amino-3-(dimethylamino)propane
(9Z)-N-[3-(dimethylamino)propyl]octadec-9-enamide
Conditions | Yield |
---|---|
With zeolite at 115 - 120℃; for 12h; Dean-Stark; | 95% |
Methyl oleate
Conditions | Yield |
---|---|
With ethyl [2]alcohol; sodium In hexane; mineral oil at 0 - 20℃; for 0.166667h; Bouveault-Blanc Reduction; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With hydrazine hydrate | 94% |
With hydrazine hydrate In ethanol for 8h; Reflux; | 82% |
With ethanol; water; hydrazine hydrate |
Conditions | Yield |
---|---|
With potassium carbonate at 144℃; under 0.1 - 10 Torr; for 6.65h; var. temp., reaction time, mole ratios of edducts; | 94% |
With potassium carbonate at 144℃; under 0.1 - 10 Torr; for 6.65h; | 94% |
RTECS : RK0895000
RTECS Class:Tumorigen
Ingestion: cis-oleic acid,methyl ester may cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation: cis-oleic acid,methyl ester may cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
cis-oleic acid,methyl ester may also cause skin and eye irritation.
Stability:Stable at room temperature in closed containers under normal storage and handling conditions.
First aid measures:
Ingestion: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation: Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin: Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Storage: Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Hazard Codes : F,Xn,N
Risk Statements :11-38-50/53-65-67
Safety Statements : 23-24/25-62-61-60-33-29-16-9
RIDADR : UN 1206 3/PG 2
WGK Germany : 1
F : 8-23
cis-oleic acid,methyl ester`s Categories: Biochemistry;Fatty Acid Esters (Plasticizer);Functional Materials;Higher Fatty Acids & Higher Alcohols;Plasticizer;Unsaturated Higher Fatty Acid Esters;Analytical Chemistry;Fatty Acid Methyl Esters (GC Standard);Standard Materials for GC
Personal Protection: Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.
Fire Fighting:Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. To extinguish fire use water spray, dry chemical, carbon dioxide, or appropriate foam.
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