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CAS No. : | 2566-91-8 | MDL No. : | |
Formula : | C19H36O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 312.49 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 12h; | |
99% | With tert.-butylhydroperoxide; [MoO<SUB>3</SUB>(2,2'-bipyridine)] In 1,2-dichloro-ethane at 75℃; for 24h; | |
97% | With formic acid; dihydrogen peroxide at 20℃; |
97% | With formic acid; dihydrogen peroxide | |
96% | With Oxone; edetate disodium; sodium hydrogencarbonate; 1,1-dioxotetrahydrothiopyran-4-one In acetonitrile for 3h; Ambient temperature; | |
96% | With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide In acetonitrile at 25℃; for 4h; Autoclave; | |
96% | With formic acid; dihydrogen peroxide In neat (no solvent) at 20 - 30℃; for 8h; Cooling with ice; | |
96% | With formic acid; dihydrogen peroxide at 60℃; for 5h; | |
96% | With formic acid; dihydrogen peroxide | |
95% | With Rf2Bimpy; oxygen; isobutyraldehyde In chlorobenzene; acetone at 40℃; for 1h; | |
93% | With formic acid; dihydrogen peroxide at 0 - 20℃; for 5h; | Epoxidation of Methyl Oleate; The epoxidation reaction was based on a Swern epoxidation19,20 which has been modified for oleochemical use by Bunker and Wool29 and used by our laboratory in the past.32 First, 420.0 g (1.4 mol) of methyl oleate is placed in a heavy duty separatory funnel type 500 mL roundbottom flask equipped with an overhead stirrer. Next, 15 g (0.3 mol) of formic acid was slowly added forming a layered mixture. The reaction flask was cooled in an ice bath and 254 g of 30% hydrogen peroxide (2.2 mol) is added over about 5 min while monitoring the temperature of the solution. The peroxide was added slowly enough such that the temperature of the solution remained below room temperature. Gas bubbles were evident as the hydrogen peroxide was added. The reaction was allowed to proceed at room temperature and alliquots were taken and analyzed by GC. The reaction was judged to be complete after 5 hrs. The product was purified in the reaction flask by stirring with 100 mL of hexanes and discarding the aqueous/formic acid layer. Then, 110 mL of saturated sodium bicarbonate solution was stirred with the hexane layer and removed. This sodium bicarbonate washing was repeated leaving the solution slightly basic. The hexane layer was dried over 80 g of anhydrous sodium sulfate, filtered through a fritted funnel. The hexane was removed with rotary evaporation (60° C.; overnight). Molecular sieves were added to ensure the product remained dry. The isolated yield was 410 g (1.3 mol: 93% yield). |
92% | With dihydrogen peroxide for 0.166667h; Irradiation; | |
92% | With ((4-(methacryloyloxy)phenyl)dimethylsulfonium)4[Mo8O26]; dihydrogen peroxide In methanol at 60℃; for 6h; | |
89% | With Amano A. lipase; 1-n-butyl-3-methylimidazolium tetrafluoroborate; dihydrogen peroxide at 30℃; for 1h; Enzymatic reaction; | |
85% | With dihydrogen peroxide; 3C25H54N(1+)*O24PW4(3-) In water at 60℃; for 5h; Green chemistry; | Cyclooctene and methyl oleate epoxidation. General procedure: In a typical catalytic run, an aqueous hydrogen peroxide solution (30-33%, 18 mmol) was placed into the 20 ml glass thermostated reactor with a magnetic stirrer.Then the catalyst (9 μmol) was added and the resulting solution was stirred for 10 min at room temperature. To initiate the reaction, the substrate (9 mmol for [Sub]/[Cat] ratio of 1000) was carefully added without stirring and then both stirring and heating of the reactor were activated simultaneously. The agitation rate was 1200 rpm. The samples were taken during the reaction at regular intervals without interruption of the stirring using an automatic micropipette. Bi-phasic samples were then diluted with ethyl acetate (190 μl) and analyzed using gas chromatography (GC) |
75% | With tert.-butylhydroperoxide In water; acetonitrile at 70℃; for 24h; | |
50.4% | With peracetic acid In diethyl ether at 20℃; for 20h; | |
24% | With oxygen at 60℃; for 72h; | |
With tert.-butylhydroperoxide at 70℃; for 80h; Yield given; | ||
100 % Spectr. | With 3-chloro-benzenecarboperoxoic acid In chloroform at 19.85℃; for 0.333333h; | |
With dihydrogen peroxide; acetic acid In water; toluene at 70℃; for 9h; | 1.1 Methyl oleate (100 parts) was epoxidized using 30% hydrogen peroxide (54.68 parts), catalyzed by Amberlite IR- 120H (16.85 parts) and acetic acid (10.1 1 parts). Toluene (47.90 parts) was added in order to improve the miscibility between the fatty acid methyl esters and the hydrogen peroxide. The epoxidation was carried out at 70°C for 9 hours. The product was then washed multiple times with water until the pH of the aqueous phase was approximately 7. The epoxidized methyl oleate was dried at 90°C under reduced pressure (<3 Torr). | |
With tert.-butylhydroperoxide In decane | ||
With formic acid; dihydrogen peroxide | ||
With tert.-butylhydroperoxide; titania nanoparticles supported on silica In dichloromethane at 89.84℃; for 24h; Inert atmosphere; | ||
With formic acid; dihydrogen peroxide In water at 0 - 20℃; for 19h; | 3 Example 3 Epoxidation of methyl oleate (EMO); To a stirred solution of methyl oleate (MO) (200.00 g, 675 mmol) and formic acid (62.09 g, 1.35 mol) cooled in an ice bath (0°C), H202 (30.0% in H20, 306.00 mL, 2.70 mol) was added slowly. The reaction was then allowed to proceed at room temperature with vigorous stirring until LC/MS analysis indicated that MO had been consumed (around 19 hr). The reaction was then transferred to a separatory funnel, and ethyl acetate (500 mL) was added and the lower aqueous phase was removed. The organic phase was then washed with water, NaHC03 and brine, dried with Na2S04, filtered, concentrated using a rotary evaporator, and placed under vacuum until constant weight was achieved to yield epoxidized oleic acid (EMO) as a clear light yellow oil (225.0 g). | |
100 %Chromat. | With C18H43Mn2N6O3(2+)*2F6P(1-); dihydrogen peroxide; oxalic acid In water; acetonitrile at 25℃; | |
With dihydrogen peroxide In water at 60℃; for 3h; | ||
74 %Chromat. | With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; | |
With 1H-imidazole; sodium periodate In water; acetonitrile at 20℃; for 48h; Molecular sieve; | ||
47 %Chromat. | With oxygen; benzaldehyde at 80℃; for 6h; | 2; 5 Example 2 Example 2 [0115] This example describes the synthesis of functionalized compounds starting from the methyl oleate. Several aldehydic reagents were tested, comprising hexanal, decanal and benzaldehyde. These three tests lead to the formation of the following products, respectively: methyl 9-(hexanoyloxy)-10-hydroxyoctadecanoate and methyl 10-(hexanoyloxy)-9-hydroxyoctadecanoate if hexanal is used; methyl 9-(decanoyloxy)-10-hydroxyoctadecanoate and methyl 10-(decanoyloxy)-9-hydroxyoctadecanoate for decanal; and lastly methyl 9-(benzoyloxy)-10-hydroxyoctadecanoate and methyl 10-(benzoyloxy)-9-hydroxyoctadecanoate when benzaldehyde was used. These three reactions are presented in Diagrams 3, 4 and 5. [0116] The reaction was carried out in a 100 ml glass reactor with mechanical agitation. In all cases, a weight of 25.0 g of methyl ester of sunflower oil HTO (high oleic content-purity: 85% methyl oleate) was placed in the reactor. A quantity of aldehyde was added; the quantity is equivalent to approximately one and one-half the number of moles of methyl oleate used. So, for the hexanal presence test, a quantity equal to 7.1 g of hexanal (purity: 98%-Sigma-Aldrich-ref.: 115606) was placed in the reactor. For decanal, this quantity was equivalent to 11.2 g (purity: 98% 0 Sigma-Aldrich-ref. D7384) and in the case of benzaldehyde, 8.6 g of benzaldehyde (purity: 99%-Sigma-Aldrich-ref.: B 1334) were added. The solid ruthenium on silica catalyst, containing 1.5% by weight of ruthenium, was added to the reaction mix at a ratio of 2% by weight of the quantity of methyl oleate used, i.e. 500 mg. [0117] Then, the medium was heated to 80° C. by a continuous bubbling air flow at atmospheric pressure. The air flow rate was controlled by a ball flow meter and was 30 ml/min. In the case of hexanal and benzaldehyde, after 6 hours of reaction, the air flow rate was stopped and the reaction medium was placed in an inert atmosphere (nitrogen). In the case of decanal, the same operation was carried out after 10 hours of reaction time. In all cases, the time necessary for total conversion of the aldehyde was allotted. Then, the reaction temperature was increased to 150° C. These parameters were maintained for 20 additional hours in the case of hexanal, 15 hours for decanal and 9 hours for benzaldehyde. Samples of the reaction medium were taken at regular intervals in order to determine the progress of the reactions. The composition of the various reaction media after each reaction step is shown in Table 2: [TABLE-US-00002] Function- alized Conversion Conversion products Type of Time to methyl to aldehyde Epoxide yield aldehyde (hours) oleate (%) (%) yield (%) (%) hexanal 6 63 100 47 0 20 76 100 11 10 decanal 10 92 100 45 2 25 95 100 10 7 benz- 6 100 93 56 0 aldehyde 15 100 96 7 17 [0118] The composition of the reaction medium was determined by gas phase chromatographic analysis. The Agilent Technologies 6870N chromatograph used is as described in Example 1. [0119] Two different temperature programs were used. The first was as follows: 50° C. (5 min.)-10° C./min.-100° C. (5 min.)-10° C./min.-150° C. (5 min.)-10° C./min.-220° C. (5 min.)-10° C./min.-250° C. (5 min.). [0120] This program allowed hexanal in particular to be detected. The hold time of the various products under the conditions described above, with a pressure level at the head of the column equal to 16.32 psi were as follows: hexanal (6.9 min.); dodecane (8.1 min.); methyl oleate (30.0 min.); methyl trans-9,10-epoxy-stearate (34.5 min); methyl cis-9,10-epoxy-stearate (34.9 min). [0121] The conversion of the reagents at time t is expressed as described in Example 1. The epoxide yield at time t was calculated as described in Example 1. [0122] The second temperature program for the furnace was as follows: 80° C. (0 min.)-13° C./min.-180° C. (6 min.)-13° C./min.-220° C. (6 min.)-17° C./min.-250° C. (10 min.). The functionalized products were detected upon completion of the analysis. [0123] The hold time for the various products at the conditions described above were as follows: dodecane (2.9 min.); decanal (5.2 min.); benzaldehyde (5.4 min.); methyl oleate (12.6 min.); methyl trans-9,10-epoxy-stearate (18.9 min.); methyl cis-9,10-epoxy-stearate (19.2 min.); methyl 9-(hexanoyloxy)-10-hydroxyoctadecanoate and methyl methyl 10-(hexanoyloxy)-9-hydroxyoctadecanoate (29.8 et 29.9 min.); methyl 9-(decanoyloxy)-10-hydroxyoctadecanoate and methyl 10-(decanoyloxy)-9-hydroxyoctadecanoate (34.4 et 34.5 min.); methyl 9-(benzoyloxy)-10-hydroxyoctadecanoate and methyl 10-(benzoyloxy)-9-hydroxyoctadecanoate (38.7 et 38.9 min.). [0124] Yields of functionalized products were calculated by assigning a response factor equal to one to a surface area of the corresponding chromatographic peaks related to that of the initial methyl oleate. [0125] All functionalized products were identified by gas phase chromatographic analysis coupled with a mass spectrometer as well as steric exclusion chromatograph. |
With [((S,S)-N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine)FeII(OTf)2]; dihydrogen peroxide In acetic acid; acetonitrile at 0℃; for 2.5h; | ||
13 %Chromat. | With plant peroxygenase from tomato (Solanum lycopersicum); dihydrogen peroxide In glycerol at 20℃; for 1h; Enzymatic reaction; | 2.5. Screening of fatty acids as substrates for SlPXG General procedure: Microsomal protein containing SlPXG (50μg) was incubated with 2mmol/l fatty acid (1μmol in 10μl methanol) and 2.5mmol/l H2O2 (1.25μmol) in 500μl sodium acetate buffer (10mmol/l, pH 6, 2% glycerol) for 20 min at 40°C. Three controls were performed with microsomal proteins from empty vector yeast cells, without proteins and without H2O2, respectively. The products were extracted twice with each 500μl CH2Cl2, the organic layer was separated and dried under a stream of nitrogen. For methylation of free carboxyl groups, the pellet was solved in 300μl MeOH, mixed with 150ml trimethylsilyldiazomethane (2mol/l) and incubated for 60min at room temperature. The samples were dried by Speedvac, re-dissolved in 200ml n-hexane and analyzed by Trace GC Ultra gas chromatograph connected to a Trace DSQ mass spectrometer (2.12). Samples containing oleyl alcohol 3a were solved in 60μl MeOH (30%) and analyzed by LC-MS (2.13). The pH optimum was determined by varying the pH values of the reaction in steps of 1 between pH 4 and 6 in sodium acetate buffer (10mmol/l, 2% glycerol) and between 7 and 9 in Tris buffer (10mmol/l, 2% glycerol), whereas 1a and H2O2 served as substrates. The temperature optimum was determined by varying the reaction temperature in steps of 10°C between 0 and 80°C in sodium acetate buffer (10mmol/l, pH 6, 2% glycerol). For determination of saturating curves the substrate concentrations were varied between 0.02 and 2mmol/l in sodium acetate buffer (10mmol/l, pH 6, 2% glycerol) with 50μg microsomal protein containing SlPXG. The values of saturating curves were used for apparent Km value calculation with excel solver (Microsoft). |
With formic acid; dihydrogen peroxide for 5h; Reflux; | ||
With formic acid; dihydrogen peroxide at 30℃; Cooling with ice; | 1 Synthesis of Epoxidized Methyl Oleate (EMO) EMO was synthesized according to prior literature methods (Bunker and Wool, 2002. Synthesis and characterization of monomers and polymers for adhesives from methyl oleate. J. Polym. Sci., Part A: Polym. Chem. 40, 451-458; Doll and Erhan, 2005. Synthesis of carbonated fatty methyl esters using supercritical carbon dioxide. J. Agric. Food Chem. 53, 9608-9614; Findley et al., 1945. Epoxidation of Unsaturated Fatty Materials with Peracetic Acid in Glacial Acetic Acid Solution. J. Am. Chem. Soc. 67, 412-414; Schmits and Wallace, 1954. Epoxidation of Methyl Oleate with Hydrogen Peroxide. J. Amer. Oil Chem. Soc. 31, 363-365). In short, methyl oleate was placed into a roundbottom flask and 4 equivalents of formic acid was added. The reaction was cooled in an ice bath, and 2 equivalents of 30% hydrogen peroxide solution was added dropwise over about 5 minutes with continuous stirring of the solution. The ice bath was removed and the reaction allowed to proceed. The temperature was monitored and the reaction was not allowed to get above 30° C. Reaction progress was monitored by taking aliquots, dissolving in heptane and injecting into the GC-MS. After the reaction was done, 1 volume of heptane was added to help layer the solution with and a separatory funnel was used to remove the acid/peroxide layer. Sodium bicarbonate solution was added, shaken with the product layer, then removed. This was repeated until the solution was no longer acidic as measured by pH paper. A saturated sodium chloride solution was shaken with the product layer, removed, and the product was dried by rotary evaporation and then on a short path drying apparatus. | |
With Isopropylbenzene; oxygen In toluene at 100℃; for 8h; | 2 Experimental CuO/γ-Al2O3 and CuO/PVPy (PVPy=polyvinylpyridine) catalysts, with an 8% metal loading, were prepared by chemisorption-hydrolysis [9]. The support (γ-Al2O3 or PVPy, 10g) was added to a [Cu(NH3)4]2+ solution obtained by the addition of NH4OH to a Cu(NO3)2·H2O water solution (4g in 20ml) until pH9. After 20min under stirring, the slurry, held in an ice bath at 0°C, was slowly diluted in order to allow hydrolysis of the copper complex and deposition of the finely dispersed product to occur. The solid was separated by filtration, washed with 0.5l of water, dried in oven overnight at 120°C. Finally, CuO/Al2O3 was calcined in static in air at 350°C for 4h, while CuO/PVPy was not treated at high temperature, in order to preserve the polymer. (0008) Metal loadings were determined by ICP-OES (ICAP6300 Duo purchased from Thermo Fisher Scientific) and an external calibration methodology, after microwave digestion of fresh and used catalysts in HNO3. (0009) High-resolution transmission electron microscopy (HRTEM) analysis of CuO/PVPy was operated at 200kV with a LIBRA 200FE analytical transmission electron microscope, equipped with FEG source and purchased from Zeiss. Samples were deposited on holey carbon-coated grids from alcohol suspensions. Samples, in the form of powders, were ultrasonically dispersed in isopropyl alcohol, and a drop of the suspension was deposited on a holey carbon film grid (300mesh). Histograms of the metal particle size distribution for the Cu samples were obtained by counting at least 300 particles onto different high resolution micrographs; the mean particle diameter (dm) was calculated by using the formula dm=Σdini/Σni where ni was the number of particles of diameter di. (0010) Reactions were performed at 100°C and under stirring (1250rpm) in a 50ml glass flask provided of a condenser, operating at atmospheric pressure, without the use of radical initiators, by bubbling molecular oxygen (30-35ml/min), in the presence of cumene as both solvent and reactant, and eventually a co-solvent (cumene+co-solvent=20ml, olefin 10 or 5mmol, catalyst 250mg). All the products were analyzed by GC-MS HP-5890 series, equipped with HP5 (5% phenyl)-methyl-polysiloxane capillary column, length 30m (initial temperature=60°C and 3min hold, then 15°C/min to 280°C and 20min hold). Conversion was calculated by using the following equation: C(%)=molMOreactedStartingmolMO100C%=molMOreactedStartingmolMO100, while selectivity was calculated as C(%)=molMOreactedStartingmolMO100.C%=molMOreactedStartingmolMO100. (0011) X-ray powder diffraction patterns were recorded within the range of 10° to 70° 2θ, with a step of 0.02° 2θ and counting time 1 or 4s/step on Philips PW-3020 powder diffractometer Ni-filtered Cu Kα radiation. The peak of CuO (111) at 2θ=35.5° was used for line-broadening determinations. (0012) Copper leaching was measured after a sulfonitric digestion of a sample of 100mg of the reaction mixture, after catalyst filtration at the end of the reaction. | |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h; | 2.4. Preparation of fatty diol from methyloleate (diol 2) To a solution of methyloleate (17.7 mmol) in 100 mL of dichloromethane, in an erlenmeyer with magnetic stirring at 0 C,were added m-chloroperoxybenzoic acide (m-CPBA, 26.6 mmol).After stirring for 3 h at 0° C, the reaction mixture was washed with water and this aqueous phase was extracted with dichloromethane. All organic phases were washed with warm water and dried(MgSO4). The solvent was evaporated to afford epoxidized methyloleate in 90-95 % yield. To a solution of lithium aluminohydride(1.83 g, 48.1 mmol) in 75 mL of anhydrous diethyl ether, in a two necked round bottom flask with magnetic stirring under nitrogen atmosphere, epoxidized methyl oleate (9.6 mmol) in 50 mL of anhydrous diethyl ether was added. After stirring for 6 h at room temperature, hydrolysis of lithioaluminate complexes was performed by dropwise addition of water. The reaction mixture was washed with saturated aqueous NaCl and dried (MgSO4). The solvent was evaporated to afford the fatty diol in 80-85% yields. 1HNMR (300 MHz, CDCl3,δ /ppm): 0.88 (s, 3H, J 6.72 Hz, CH3);1.24-1.59 (m, 30H, alkyl chain); 3.58 (m, 1H, CH-OH); 3.64 (m, 2H,CH2-OH). 13C NMR (75 MHz, CDCl3,δ /ppm): 13.2, 21.8, 25.3, 26.0,28.4-28.9, 31.0, 32.8, 37.1, 62.2, 71.2. IR (ATR): ν 3338 cm1(s,νOH), disappearance of ester band at 1740 cm-1. | |
With dihydrogen peroxide In acetonitrile at 80℃; for 5h; | 2.3. Methyl oleate epoxidation The catalytic performance of the niobium oxide-based mate-rials was evaluated in methyl oleate epoxidation with hydrogenperoxide as oxidant.Epoxidation reactions were carried out in a round-bottom glassbatch reactor, put in an oil bath, equipped with a condenser andthermometer, and a magnetic bar for vigorous stirring (300 rpm).In a typical experiment, 600 mg of catalyst, 20 cm3of acetonitrile,5 g of methyl oleate (25 mmol) and 6.9 g of hydrogen peroxide54.9 wt% (111 mmol) were used. The temperature was kept con-stant (≈80C) with solvent refluxing. All reagents were added inone pot at the beginning of the reaction. | |
With tert.-butylhydroperoxide; (H3biim)4[β-Mo8O26]; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 70℃; for 24h; | 2.3 Catalytic Tests Epoxidation reactions were carried out under autogenous pressure using 5 mL borosilicate reactors equipped with a Teflon valve and a magnetic stirrer. The reactors were charged with an amount of 1 equivalent to 18 lmol Mo, 1.8 mmol of olefin [cis-cyclooctene (Cy) or methyloleate (Ole)] and co-solvent (2 mL organic solvent or 0.3 mL IL), and immersed in an oil bath set at 55 or 70 °C. The organic solvent was CH3CN or α,α,α-trifluorotoluene (TFT), and the IL was 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([bmim]NTf2).The reaction mixtures were stirred at 1000 rpm at the reaction temperature for 10 min prior to addition of the oxidant [2.75 mmol of tert-butylhydroperoxide (TBHP) or H2O2]. This instant was taken as time zero for kinetics tudies.For reactions with TBHP as oxidant, samples were taken periodically, while for reactions with H2O2, individual experiments were performed for a given reaction time. The evolution of the reactions was monitored by gas chromatography using a Varian 3900 GC equipped with a DB-5 capillary column (30 m x 0.25 mm x 0.25 lm) and a FID detector, with H2 as carrier gas. Undecane and methyl decanoate were used as internal standards for Cy and Ole reactions, respectively. The reaction products were identifiedby GC-MS (Trace GC 2000 Series Thermo Quest CE Instruments GC; Thermo Scientific DSQ II) using He as carrier gas. | |
With formic acid; dihydrogen peroxide In water at 20℃; for 14h; Cooling with ice; | ||
With tert.-butylhydroperoxide; [Mo2O6((S)-4-(1-phenylpropyl)-1,2,4-triazole)2]*H2O In decane at 70℃; for 6h; | ||
With 3C41H72N2(2+)*2O24PW4(3-); dihydrogen peroxide In water at 60℃; for 3h; | ||
With tert.-butylhydroperoxide; molybdenum(IV) dioxide In chloroform; chlorobenzene at 60℃; for 6h; | ||
With tert.-butylhydroperoxide In 1,2-dichloro-ethane at 80℃; for 24h; | ||
With dihydrogen peroxide; acetic acid In neat (no solvent) at 50 - 85℃; Ionic liquid; | 2 Embodiment 2 epoxidation under same conditions (feeding ratio and temperature) and sampling analyses at distinct reaction time. Methyl oleate and acetic acid (the molar ratio of methyl oleate to acetic acid=1:0.5) are added into a reaction bottle, mixed with 8% acidic ionic liquids, and agitated and heated to 50° C. 30% hydrogen peroxide solutions (the mole of hydrogen peroxide is 1.5 times as many as that of methyl oleate) are controllably instilled in the reaction bottle within 1 hour and heated to 7085° C. for generation of raw products in 15 hours. The raw products are kept at a standing condition for separation of the aqueous phase and the oil phase. The oil phase in the upper layer is rinsed with sodium bicarbonate solutions and deioned water to derive epoxidized oleates after removal of water. It can be seen from outcomes that both productivity and selectivity of epoxidized oleates in longer reaction time are decreased. As shown in FIG. 2, productivity of epoxidized oleates is 74.5% (reaction temperature: 70° C.; best reaction time: 4 hours) and 84.8% (reaction temperature: 85° C.; best reaction time: 3 hours), respectively. | |
92 %Chromat. | With tert.-butylhydroperoxide; bis(3,5-dimethylanilinium) trimolybdate In decane at 70℃; for 24h; | 2.4. Catalytic tests General procedure: The IPH catalysts were tested for the epoxidation the olefins methyloleate (Ole), methyl linoleate (LinOle), R-(+)-limonene (Lim), and ciscyclooctene(Cy), using tert-butylhydroperoxide (tbhp) as oxidant, andα,α,α-trifluorotoluene (tft) as solvent. Hydrogen peroxide was used (forselected catalytic system) as oxidant instead of tbhp, with acetonitrile(acn) as cosolvent allowing the miscibility of the substrate and oxidant.For the reaction of Ole with tbhp, different cosolvents were tested,namely, 1.2-dichloroethane (dce), toluene (tol), and acn, besides tft.The catalytic reactions were carried out in 10 ml borosilicate reactorsequipped with a Teflon valve (for sampling) and a magnetic stirrer. Thereactor was loaded with catalyst (18 μmol Mo), co-solvent (1 ml) andolefin (1.8 mmol), and then immersed in a temperature-controlled oilbath at 55 or 70 °C, under stirring (1000 rpm), for 10 min. The oxidant(2.75 mmol for Cy, Lim and Ole, and 2.75 mmol or 4.80 mmol forMeOle reactions) was pre-heated in a separate flask for 10 min at thesame temperature, and then added to the reactor. The instant that thepre-heated oxidant was added to the reactor was taken as the initialinstant of the catalytic reaction. The reaction mixtures were analyzedusing a Varian 3900 GC equipped with a DB-5 capillary column(30m×0.25mm×0.25 μm) and a FID detector, with H2 as the carriergas, and quantifications were based on calibrations. The internal standardsused were undecane for the Cy and Lim reactions, and methyldecanoate for the Ole and LinOle reactions. The experimental range oferror was less than 6%, based on replicates carried out for selectedexperimental conditions. The material balance considering all reactionproducts quantified by GC closed in: 100% for Cy at 24 h reaction,100% for Ole at 6 h, 98% for Lime and 98% LinOle at 24 h reaction,70 °C. The reaction products were identified by GC-MS (Trace GC 000Series Thermo Quest CE Instruments GC; Thermo Scientific DSQ II),using He as the carrier gas. The product identifications were based oncommercial mass spectrometry databases (Wiley6, NIST2.0, NISTChemistry WebBook, MAINLIB), and mass spectral matching data. |
With unspecific peroxygenases from Chaetomium globosum; dihydrogen peroxide In acetone at 40℃; for 1h; Enzymatic reaction; | ||
57 %Chromat. | With tert.-butylhydroperoxide; [Mo<SUB>2</SUB>O<SUB>6</SUB>(2,2'-bipyridine)] In decane at 55℃; for 24h; Sealed tube; chemoselective reaction; | |
With formic acid; dihydrogen peroxide at 10℃; for 12h; Inert atmosphere; | 1.3; 2.3; 3.3; 4.3; 5.3; 6.3; 7.3 3) Epoxidation reaction: Take the above 2) Methyl oleate obtained reaction product was 11.86g (0.04 mol)Add to the magnetic stirrer,Condenser tube,A three-neck round bottom flask of nitrogen gas introduction tube was charged with 13.60 g (0.12 mol) of 30% hydrogen peroxide solution and 10.46 g of 88% formic acid according to methyl oleate: hydrogen peroxide: formic acid = 1:3:5 (molar ratio). (0.20 mol),Under a nitrogen atmosphere,The reaction was stirred at 10 ° C for 12 h.The obtained reaction solution was extracted with ethyl acetate.Saturated with sodium bicarbonate solution,Drying over anhydrous sodium sulfate and concentrating in vacuo to give 11.24 g of methyl 9,10-epoxystearate.The purity of the product was determined by gas chromatography to be 93%. | |
With C20H26N4*2CF3O3S(1-)*Mn(2+); dihydrogen peroxide; acetic acid In water; acetonitrile at 20℃; for 1.25h; Green chemistry; | ||
99 %Chromat. | With tert.-butylhydroperoxide In aq. phosphate buffer at 25℃; for 1h; | In the test for peroxygenase activity, defatted oat flour (2 g) or thesuitable enzyme preparation deriving from 2 g of flour was suspendedin 7 mL of 50mM potassium phosphate buffer at pH 7.5. To this suspensionmethyl oleate (13 μL, 11.4 mg, 38 μmol) and t-BuOOH (70 wt%in H2O, 13 μL, 8.5 mg, 95 μmol) were added and the reaction mixturewas maintained under vigorous stirring at 25 °C. The reaction progresswas monitored by GC analysis of aliquots (0.4 mL) of the reaction takenat regular intervals and extracted with MeOH:Et2O 1:9 v/v (0.4 mL);3 μL of the dried organic solution were injected for the GC analyses. |
With formic acid; dihydrogen peroxide In toluene at 0 - 80℃; for 8h; | Synthesis of Epoxy Methyloleate The obtained methyl oleate (MO) was epoxidized with the help of in-situ-generated performic acid using toluene as a solvent (Campanella et al., 2008). A solution of MO (5 g) in toluene (25 mL) was taken in a 25 mL two-neck roundbottomed flask kept at 0 °C. To the above solution, H2O2 (6.20 mL, 202.364 mmol) and formic acid (1.90 mL, 50.59 mmol) were added sequentially as catalyst. Initially, the reaction mixture was stirred at 0 °C as the reaction is exothermic in nature. After 15 min, the reaction mixture was stirred at 80 °C for 8 hours. After completion (as monitored by TLC), the reaction mixture was cooled to room temperature and quenched with 5 % (w/w) NaHCO3 to neutralize the acid. The organic layer (containing EMO) was extracted using ethylacetate (3 × 30 mL) from above biphasic mixture (toluene and water), collected, dried over anhydrous Na2SO4, and concentrated in vacuo; further the obtained residue was purified by flash chromatography (EtOAc/hexane 0.5: 9.5) to afford epoxy methyl oleate (~97% pure) as colorless liquid. [Rf = 0.7, EtOAc/hexane 0.5: 9.5 v/v]. | |
With dihydrogen peroxide at 50℃; for 4h; | Catalytic Oxidation and Product Analysis General procedure: Catalytic experiments were carried out in thermostaticallycontrolled glass vessels with vigorous stirring(500 rpm). Typical conditions for oxidation reactionswere the following: 0.1 M alkene, 0.1-0.2 M H2O2,10 mg of 15 wt % PW4/N-CNT, 1 mL of MeCN, and50°C. The reaction conditions were chosen based onthe results of earlier studies of heterogeneous catalystsbased on PW4 [24, 25]. Reactions started with theaddition of H2O2. The reaction products were identifiedby gas chromatography-mass spectrometry(GC-MS) and 1H NMR spectroscopy and quantitativelydetermined on a gas chromatograph usingbiphenyl as an internal standard | |
With tert.-butylhydroperoxide; MoO3*H2O*C6H6N4 at 70℃; for 24h; | ||
With dihydrogen peroxide; <i>tert</i>-butyl alcohol at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 82% 2: 14% | With R Amano K lipase; 1-butyl-3-methylimidazolium hexafluorophosphate; dihydrogen peroxide at 30℃; for 5h; Enzymatic reaction; | |
1: 24% 2: 60% | With Amano A. lipase; 1-n-butyl-3-methylimidazolium tetrafluoroborate; dihydrogen peroxide at 30℃; for 3h; Enzymatic reaction; | |
1: 42% 2: 25% | With tert.-butylhydroperoxide; MoO<SUB>3</SUB>(2-(2-pyridyl)benzimidazole) at 70℃; for 24h; Inert atmosphere; Schlenk technique; |
With dihydrogen peroxide In water at 65℃; for 3h; | 1.a; 2.a There were introduced into a reactor:1000 g of crude methyl oleate (methyl esters from sunflower oil with an extremely high content of oleic acid: 92% methyl oleate; 1% methyl linoleate; 4% methyl palmitate; 3% methyl stearate)1O g of tungstic acid5O g of crude methyl dihydroxy stearate (the intermediate obtained at the end of step (a) coming from a preceding reaction, the so-called «reaction foot»).The temperature was increased to 65°C, and 250 cc of 49.9% H2O2 solution were added in 3 h. In the course of the reaction, nitrogen was made to flow to distil a part of the water produced in the process. Approximately 70 cc of water were distilled in the course of the 3 h. Once addition of H2O2 had been completed, approximately 7 g of sodium bicarbonate dissolved in 100 cc water were added to convert tungstic acid into tungstate, which is more soluble in water, and the aqueous phase was separated when hot (at approximately 600C) from the organic phase. Approximately 15O g of aqueous solution containing the catalyst were thus separated, and approximately 1150-1200 g of oily phase were obtained. Of this oily phase 50 g were set aside as "reaction foot" for the subsequent reaction. The oily phase contained 75-80% of methyl dihydroxystearate, a small amount Of H2O2 (1- 2%), palmitate and stearate, which do not participate in the reaction, methyl 9,10- epoxystearate, which is an intermediate of reaction, pelargonic acid and monomethyl azelate, which already start to form in this reaction step, and acetals that derive from secondary reactions.; Example 2; Step (a);There were introduced into a reactor: 1000 g of crude methyl oleate (methyl esters from sunflower oil with high content of oleic acid: 84% methyl oleate; 9% methyl linoleate; 4% methyl palmitate; 3% methyl stearate)1O g of tungstic acid5O g of crude methyl dihydroxy stearate (the intermediate obtained at the end of step (a) coming from a preceding reaction, the so-called «reaction foot»)The temperature was increased to 60-620C, and 250 cc of 49.9% H2O2 solution were added in 3 h. The reaction was carried out as described in the example 1.After salification of tungstic acid with a sodium bicarbonate solution, the aqueous phase, containing tungstate, was separated, while the organic phase (approximately 115O g of oily phase), containing 70-75% of methyl dihydroxystearate, was ready for the subsequent oxidative step. | |
With formic acid; dihydrogen peroxide | ||
1: 65 %Chromat. 2: 18 %Chromat. | With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; water; dihydrogen peroxide In <i>tert</i>-butyl alcohol at 40℃; for 16h; | |
With formic acid; dihydrogen peroxide In toluene at 21℃; for 24h; | ||
Stage #1: Methyl oleate With [MoO3(1,2,4-triazole)0.5] In water; acetonitrile at 70℃; for 0.166667h; Stage #2: With dihydrogen peroxide In water; acetonitrile at 70℃; for 24h; | 2.5. Catalytic tests General procedure: Catalytic reactions were carried out at 70 C in 5 mL borosilicatereactors equipped with valves for sampling and a PTFE magneticstirring bar. Typically, an amount of hybrid compound equivalentto 18 lmol of Mo or W, 1.8 mmol of substrate (1.2 M), and 1 mLof cosolvent (CH3CN) was added to the reactor, which was thenimmersed in a temperature-controlled oil bath. After stirring(1000 rpm) for 10 min, oxidant (2.75 mmol) was added, and thereaction time was counted from this instant. | |
With tert.-butylhydroperoxide; [Mo2O6((S)-4-(1-phenylpropyl)-1,2,4-triazole)2]*H2O In decane at 70℃; for 24h; | ||
With 3C41H72N2(2+)*2O24PW4(3-); dihydrogen peroxide In methanol; water at 60℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13%Chromat. | With 5% Ru/SiO2; oxygen; at 80 - 150℃; for 12h; | Example 1 [0105] This example presents a comparison of various catalysts consisting of a metal deposited on a silicon media. All catalysts were prepared using ionic exchange starting from a colloidal silica stabilized with ammonium ions and metal chloride corresponding to the active species. These items were tested in regards to the functionalization reaction of methyl oleate by hydroxycitronellal which lead to the synthesis of 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate and of 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate as illustrated in Diagram 2. [0106] The reaction was carried out in a 100 ml glass reactor with mechanical agitation. Twenty-five grams (25.0 g) of methyl ester of sunflower oil HTO (high oleic content-purity: 85% methyl oleate) as well as 13.0 g of hydroxycitronellal (FCC Grade: Purity?95%-Sigma-Aldrich, Ref. W258318) were introduced into the reactor. The solid catalyst of the metal type supported on silica contains 5% by weight of the quantity of methyl oleate engaged, i.e. 250 mg. The environment was heated to 80 C. with continuous air bubbling. The air flow was controlled by a ball flow meter at 70 ml/min. After 7 hours of reaction time, the air flow was stopped and the reaction medium was raised to 150 C. These parameters were maintained for 5 additional hours. Samples of the reaction medium were taken at regular intervals in order to determine the status of the reaction. The reagent conversion rates and the yield rates of the desired products after 7 and 12 hours of reaction time are shown in Table 1: [TABLE-US-00001] Conversion Function- into alized Conversion hydroxy- Epoxide products Type of Reaction into methyl citronellala yield yield catalyst time (hr.) oleate (%) (%) (%) (%) no catalyst 7 37 70 27 11 12 46 92 9 24 Ru/SiO2 7 75 95 52 24 12 80 100 13 39 Co/SiO2 7 76 100 31 19 12 77 100 16 29 Zn/SiO2 7 66 99 30 20 12 69 100 10 27 Ni/SiO2 7 51 90 34 15 12 59 98 13 25 Cr/SiO2 7 49 89 31 15 12 56 97 13 25 Cu/SiO2 7 34 90 24 16 12 38 97 11 22 Rh/SiO2 7 34 86 18 17 12 40 96 8 26 [0107] The composition of the reaction medium was determined by gas phase chromatographic analysis. The Agilent Technologies 6870N chromatograph is equipped with a capillary column (SGE-BPX-70-length: 30 m, inside diameter: 0.25 mm, film thickness: 0.25 mum), of a split/splitless injector and a flame ionization detector (temperature of the injector and the detector: 280 C.). The temperature program of the furnace was as follows: 80 C. (0 min.)-13 C./min.-180 C. (6 min.)-13 C./min.-220 C. (6 min.)-17 C./min.-250 C. (10 min.). [0108] The hold time for the various products under the conditions described above are as follows: dodecane (2.9 min.); hydroxycitronellal (8.9 min.); methyl oleate (12.6 min.); methyl trans-9,10epoxy-stearate (18.9 min.); methyl cis-9,10-epoxy-stearate (19.2 min). [0109] The conversion of reagents at time t is expressed as follows: (number of initial moles of reagent-number of moles of reagent at time t)/number of initial moles of reagent*100. [0110] The epoxide yield at time t was calculated as follows: number of moles of epoxide at time t/(number of initial moles of methyl oleate*relative response coefficient of 9,10-epoxystearate in relation to methyl oleate)*100. [0111] The functionalized products, i.e. the methyl octadecanoate 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy) and the methyl octadecanoate 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy), were analyzed by steric exclusion chromatography. [0112] The Waters Alliance 2695 chromatograph is equipped with a refraction index detector (RI 410) and with two different columns (Styrage-HR 0.5 and Styragel-HR 1). The temperature of the furnace containing the columns is set at 30 C. and tetrahydrofurane (THF) is used as an eluent at a flow rate of 0.8 ml/min. [0113] Under these conditions, the hold times were as follows: products with high molecular weight (>1000 uma; 15.1 min); functionalized products (16.2 min.); methyl oleate and methyl 9,10-epoxy-stearate (18.1 min.); hydroxycitronellal (19.0 min.). [0114] The functionalized products yield is the relative surface area of the chromatographic peak expressed as a percentage of the total of all peaks. |
52%Chromat. | With 5% Ru/SiO2; oxygen; at 80℃; for 7h; | Example 1 [0105] This example presents a comparison of various catalysts consisting of a metal deposited on a silicon media. All catalysts were prepared using ionic exchange starting from a colloidal silica stabilized with ammonium ions and metal chloride corresponding to the active species. These items were tested in regards to the functionalization reaction of methyl oleate by hydroxycitronellal which lead to the synthesis of 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate and of 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate as illustrated in Diagram 2. [0106] The reaction was carried out in a 100 ml glass reactor with mechanical agitation. Twenty-five grams (25.0 g) of methyl ester of sunflower oil HTO (high oleic content-purity: 85% methyl oleate) as well as 13.0 g of hydroxycitronellal (FCC Grade: Purity?95%-Sigma-Aldrich, Ref. W258318) were introduced into the reactor. The solid catalyst of the metal type supported on silica contains 5% by weight of the quantity of methyl oleate engaged, i.e. 250 mg. The environment was heated to 80 C. with continuous air bubbling. The air flow was controlled by a ball flow meter at 70 ml/min. After 7 hours of reaction time, the air flow was stopped and the reaction medium was raised to 150 C. These parameters were maintained for 5 additional hours. Samples of the reaction medium were taken at regular intervals in order to determine the status of the reaction. The reagent conversion rates and the yield rates of the desired products after 7 and 12 hours of reaction time are shown in Table 1: [TABLE-US-00001] Conversion Function- into alized Conversion hydroxy- Epoxide products Type of Reaction into methyl citronellala yield yield catalyst time (hr.) oleate (%) (%) (%) (%) no catalyst 7 37 70 27 11 12 46 92 9 24 Ru/SiO2 7 75 95 52 24 12 80 100 13 39 Co/SiO2 7 76 100 31 19 12 77 100 16 29 Zn/SiO2 7 66 99 30 20 12 69 100 10 27 Ni/SiO2 7 51 90 34 15 12 59 98 13 25 Cr/SiO2 7 49 89 31 15 12 56 97 13 25 Cu/SiO2 7 34 90 24 16 12 38 97 11 22 Rh/SiO2 7 34 86 18 17 12 40 96 8 26 [0107] The composition of the reaction medium was determined by gas phase chromatographic analysis. The Agilent Technologies 6870N chromatograph is equipped with a capillary column (SGE-BPX-70-length: 30 m, inside diameter: 0.25 mm, film thickness: 0.25 mum), of a split/splitless injector and a flame ionization detector (temperature of the injector and the detector: 280 C.). The temperature program of the furnace was as follows: 80 C. (0 min.)-13 C./min.-180 C. (6 min.)-13 C./min.-220 C. (6 min.)-17 C./min.-250 C. (10 min.). [0108] The hold time for the various products under the conditions described above are as follows: dodecane (2.9 min.); hydroxycitronellal (8.9 min.); methyl oleate (12.6 min.); methyl trans-9,10epoxy-stearate (18.9 min.); methyl cis-9,10-epoxy-stearate (19.2 min). [0109] The conversion of reagents at time t is expressed as follows: (number of initial moles of reagent-number of moles of reagent at time t)/number of initial moles of reagent*100. [0110] The epoxide yield at time t was calculated as follows: number of moles of epoxide at time t/(number of initial moles of methyl oleate*relative response coefficient of 9,10-epoxystearate in relation to methyl oleate)*100. [0111] The functionalized products, i.e. the methyl octadecanoate 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy) and the methyl octadecanoate 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy), were analyzed by steric exclusion chromatography. [0112] The Waters Alliance 2695 chromatograph is equipped with a refraction index detector (RI 410) and with two different columns (Styrage-HR 0.5 and Styragel-HR 1). The temperature of the furnace containing the columns is set at 30 C. and tetrahydrofurane (THF) is used as an eluent at a flow rate of 0.8 ml/min. [0113] Under these conditions, the hold times were as follows: products with high molecular weight (>1000 uma; 15.1 min); functionalized products (16.2 min.); methyl oleate and methyl 9,10-epoxy-stearate (18.1 min.); hydroxycitronellal (19.0 min.). [0114] The functionalized products yield is the relative surface area of the chromatographic peak expressed as a percentage of the total of all peaks. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium(IV) oxide at 120℃; for 72h; | 1 Synthesis of Phosphorous Containing Compounds General procedure: In a small dried reaction vial, 625 mg of EMO was added to 650 mg bis-2-ethylhexyl phosphate or 450 mg of dibutyl phosphate. Separate reactions were conducted with and without catalyst. In the reactions where catalyst was used, it was added at this time. The reaction was capped and a conical magnetic stirbar matched to the reaction vial was used. The reaction was heated to the reaction temperature, 95, 120, or 140° C., and the reaction allowed to proceed for 24-72 hours. The reaction was filtered using a syringe filter and further analysis was performed. Reactions of twice this scale were also performed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert.-butylhydroperoxide; C36H56ClMnN2O2P2(2+)*2Cl(1-) In water; toluene at 26℃; for 4h; Sealed tube; | 10 Example 10 200 mg of methyl oleate (MO) was taken along with 1 ml of toluene in a 10 ml glass tube. 5 mg (2.5 wt.% w.r.t. LA) of C-7 and 280 of TBHP (70 wt.% in water) were added to the tube. The glass tube was then sealed well with a rubber septum and carbon dioxide (C02) gas was bubbled in the system continuously using a needle. The contents in the glass tube were stirred well for 4 h at 26 °C. The remaining procedure was followed as given in Example 1. The conversion of MO was 32% and the selectivity of epoxides/cyclic carbonates was 24/76% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(II) bis(tetrafluoroborate); at 50 - 70.1℃; for 2h; | This example shows a procedure for making the etherified product of <strong>[77-93-0]triethyl citrate</strong> and epoxidized methyl oleate. (0078) 20.03 g (0.0641 mol) of epoxidized methyl oleate was mixed in a reactor with 15.00 g (0.0543 mol) of <strong>[77-93-0]triethyl citrate</strong> and heated to 50 C. 0.44 g of copper (II) tetrafluoroborate was dissolved into 3.00 g (0.0109 mol) of <strong>[77-93-0]triethyl citrate</strong> and added to the reactor. The reaction was immediately exothermic and reached a maximum temperature of 70.1 C. The reaction was analyzed after 1 hour by proton NMR and shown to be nearly complete. The reaction was stopped after 2 hours of total reaction time. |
Tags: 2566-91-8 synthesis path| 2566-91-8 SDS| 2566-91-8 COA| 2566-91-8 purity| 2566-91-8 application| 2566-91-8 NMR| 2566-91-8 COA| 2566-91-8 structure
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H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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