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[ CAS No. 106-18-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 106-18-3
Chemical Structure| 106-18-3
Chemical Structure| 106-18-3
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Product Details of [ 106-18-3 ]

CAS No. :106-18-3 MDL No. :MFCD00042870
Formula : C16H32O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NDKYEUQMPZIGFN-UHFFFAOYSA-N
M.W : 256.42 Pubchem ID :61015
Synonyms :
Chemical Name :Butyl dodecanoate

Safety of [ 106-18-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 106-18-3 ]

* 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.

  • Downstream synthetic route of [ 106-18-3 ]

[ 106-18-3 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 542-52-9 ]
  • [ 106-18-3 ]
  • decyl-malonic acid dibutyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium n-butoxide unter gleichzeitigem Abdestillieren des entstehenden Butanols bei 40-50 mm Druck;
With potassium n-butoxide unter gleichzeitigem Abdestillieren des entstehenden Butanols bei 40-50 mm Druck;
  • 2
  • [ 106-18-3 ]
  • [ 629-25-4 ]
  • [ 824-55-5 ]
  • [ 102456-10-0 ]
  • 3
  • [ 143-07-7 ]
  • [ 71-36-3 ]
  • [ 106-18-3 ]
YieldReaction ConditionsOperation in experiment
99% at 70℃; for 24h;
98% With nano sulfated-TiO2 In neat (no solvent) at 80℃; for 1.5h;
97% With 1-(4-Nitrophenyl)-1H-imidazole-3-ium trifluoromethanesulfonate at 80℃; for 4h; Sealed tube; Green chemistry; 2.2. General procedure for the synthesis of biodiesel General procedure: A magnetic stir bar placed in a sealed tube, Free Fatty Acids (FFAs), methanol, and ionic liquids were added. The esterification was then carried out for a length of time at a specific temperature with vigorous stirring. After the reaction was completed, the residue was cooled to room temperature and kept at the same temperature until phase separation. The reaction mixture was extracted with ether and water. The upper phase (volume) mainly containing the desired ester could be isolated simply by liquid/liquid phase separation, concentrated, and column chromatography; the bottom phase ionic liquid in water from the reaction could be reused after removal of water under reduced pressure. For several experiments separated organic phase was directly concentrated and the product was confirmed by NMR spectrometry/ mass spectrometry.
95% With toluene-4-sulfonic acid; 1-octyl-3-methylimidazolium tetrafluoroborate at 80℃; for 1h;
94% In cyclohexane at 85 - 90℃; for 2.5h;
92.5% With 3H(1+)*O40SiW12(4-)*C21H22O3PS(1+) Reflux; Dean-Stark; The procedure for the esterification General procedure: Acidic pseudo-IL (0.05 g) was loaded into a 50-mL threenecked flask with a magnetic stirrer, and a reflux condenser. A Dean-Stark apparatus was used to remove the water continuously from the reaction mixture. n-Butanol (14.8 g,0.2 mol) and aliphatic acid (with -OH/-COOH molar ratio = 1.5:1) were added and reaction was carried out under reflux condition. The reaction progress was monitored by the acid-base titration. The conversion of the reaction was calculated on the acidity using the following equation: Conversion (%) = [1 - (final acidity)/(initial acidity)] × 100%. Here, the acidity from acidic pseudo-IL was excluded. For final and initial acidity, the acidity from the pseudo-IL was subtracted. The products were confirmed using GC-MS analysis. After reaction, the IL was separated from the reaction mixture by cooling the temperature, which made the catalyst recovery quite simple.
91.4% With [3-(1-methylimidazolium-3-yl)propane-1-sulfonate]3PW12O40 at 110℃; for 2h;
68% With sulfuric acid Reflux;
39.7% With sulfonic acid modified hollow 1,4-bis(hydroxymethyl)benzene-based polymer nanospheres at 30℃; for 6h;
8.1% With phosphate buffer In water at 45℃; for 18h;
With sulfuric acid
With toluene-4-sulfonic acid In various solvent(s) at 80℃; for 24h;
78 %Chromat. With trimethylcyclohexylammonium methanesulfonate; toluene-4-sulfonic acid at 60℃; for 2h; General procedure: Equimolar amounts of quaternary ammonium salt (1.5 mmol) and p-toluenesulfonic acid monohydrate (Sigma-Aldrich, 98,5+% used as received) were mixed in a screw-capped 3 ml vial. The mixture was magnetically stirred and heated to 60 °C until a clear colourless liquid was obtained (about 10 min). DES was used right after its preparation. Equimolar amounts (4.5 mmol) of acid and alcohol were added, and the resulting mixture, was heated to 60 °C (or 80 °C if specified) and magnetically stirred for the specified amount of time. Initially the reaction mixture is homogeneous and fluid, and then a heterogeneous system formed as reaction proceeded, due to insolubility of the esters produced in the DES. For the g.c. analysis further elaboration was as follows. At the end of the reaction, tbutylbenzene was added, as the internal standard, to the mixture, which was then extracted with diethyl ether. Organic layer was washed with NaHCO3, dried over Na2SO4 and analyzed by g.c.
With Poly(VMPS)-PW at 120℃; for 2h; Neat (no solvent);
With rod-shaped meso-porous silica immobilized Porcine pancreatic lipase In aq. phosphate buffer; hexane at 39.84℃;
With lipase B from Candida antarctica at 40℃; for 6h; Green chemistry; Enzymatic reaction;
With poly(p-styrenesulfonic acid) grafted multi-walled carbon nanotube with graphene oxide at 120℃; for 10h;
With boron trifluoride
92 %Chromat. With 3C14H32N2O6S2(2+)*2O40PW12(3-) at 110℃; for 1.5h; 2.5. Typical procedure for the [PhBs1]3-PW, [PipBs1]3-PW and[PipBs2]3-(PW)2 catalyzed esterification reaction General procedure: In a typical esterification reaction procedure, a round-bottomedflask with a water segregator was charged with acetic acid (1.80 g,30 mmol), n-butanol (2.67 g, 36 mmol), and optimized amount ofeach catalyst (0.25 g of [PhBs1]3-PW, 0.25 g of [PipBs1]3-PW and0.15 g of [PipBs2]3-(PW)2). The resulting solution was heated underreflux condition at 110 °C for 1.5 h with vigorous stirring, seeScheme 3. Then, the reaction mixture was cooled to room temperature.The top liquid layer was simply separated by decantation(or filtration) and analyzed using the gas chromatography. For otheresterification reactions, the test was carried out accordingly.Exceptionally, for esterification of acetic acid with ethanol, cyclohexane was added as the water-carrying agent.
With tetrakis(4-ethynylphenyl)methane for 24h; Reflux; 4.2.2. Esterification General procedure: 100 mg of carboxylic acid, 10 mg of catalyst and 5 mL of n-butanol were introduced into the flask (25 mL) and kept under stirring (400 rpm) under reflux for 24 h.

Reference: [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US6350896, 2002, B1 Location in patent: Example 6
[2]Hosseini-Sarvari, Mona; Sodagar, Esmat [Comptes Rendus Chimie, 2013, vol. 16, # 3, p. 229 - 238]
[3]Ho, Wen-Yueh; Lin, Wesley; Lin, Yi-Jyun; Luo, Shun-Yuan; Pantawane, Amit; Su, Po-Fang; Thul, Mayur; Tseng, Shao-An; Wu, Hsin-Ru [Catalysis Communications, 2021, vol. 149]
[4]Nguyen, Hoang-Phuong; Znifeche, Samira; Baboulene, Michel [Synthetic Communications, 2004, vol. 34, # 11, p. 2085 - 2093]
[5]Ma, Jie; Jiang, Heng; Gong, Hong [Organic Preparations and Procedures International, 2005, vol. 37, # 1, p. 87 - 92]
[6]Shi, Yingxia; Liang, Xuezheng [Chemical Papers, 2019, vol. 73, # 6, p. 1413 - 1421]
[7]Location in patent: experimental part Leng, Yan; Wang, Jun; Zhu, Dunru; Ren, Xiaoqian; Ge, Hanqing; Shen, Lei [Angewandte Chemie - International Edition, 2009, vol. 48, # 1, p. 168 - 171]
[8]Location in patent: experimental part Sarova, Devinder; Kapoor, Archana; Narang, Rakesh; Judge, Vikramjeet; Narasimhan, Balasubramanian [Medicinal Chemistry Research, 2011, vol. 20, # 6, p. 769 - 781]
[9]Kim, Il; Kim, Ji Su; Song, Wenliang; Varyambath, Anuraj; Zhang, Yu [Green Chemistry, 2020, vol. 22, # 11, p. 3572 - 3583]
[10]Omar, Ibrahim Che; Nishio, Naomichi; Nagai, Shiro [Agricultural and Biological Chemistry, 1987, vol. 51, # 8, p. 2153 - 2160]
[11]Rheinboldt; Koenig; Otten [Justus Liebigs Annalen der Chemie, 1929, vol. 473, p. 255]
[12]Jiang, Tao; Chang, Yanhong; Zhao, Guoying; Han, Buxing; Yang, Guanying [Synthetic Communications, 2004, vol. 34, # 2, p. 225 - 230]
[13]Location in patent: scheme or table De Santi, Valerio; Cardellini, Fabio; Brinchi, Lucia; Germani, Raimondo [Tetrahedron Letters, 2012, vol. 53, # 38, p. 5151 - 5155]
[14]Location in patent: experimental part Leng, Yan; Jiang, Pingping; Wang, Jun [Catalysis Communications, 2012, vol. 25, p. 41 - 44]
[15]Zhang, Jinyu; Zhou, Guowei; Jiang, Bin; Zhao, Minnan; Zhang, Yan [Journal of Solid State Chemistry, 2014, vol. 213, p. 210 - 217]
[16]Eby; Peretti [RSC Advances, 2015, vol. 5, # 39, p. 30425 - 30432]
[17]Bian, Gang; Jiang, Pingping; Zhang, Weijie; Jiang, Kelei; Hu, Ling; Jian, Zhang; Shen, Yirui; Zhang, Pingbo [RSC Advances, 2015, vol. 5, # 110, p. 90757 - 90765]
[18]Mannion, David T.; Furey, Ambrose; Kilcawley, Kieran N. [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 1, p. 499 - 506]
[19]Keshavarz, Mosadegh; Iravani, Nasir; Parhami, Abolfath [Journal of Molecular Structure, 2019, vol. 1189, p. 272 - 278]
[20]Sekerová, Lada; Vyskočilová, Eliška; Červený, Libor; Sedláček, Jan [Tetrahedron, 2019, vol. 75, # 20, p. 2877 - 2882]
YieldReaction ConditionsOperation in experiment
Dibutylzinn-dilaurat, Butylorthotitanat;
  • 5
  • [ 106-18-3 ]
  • [ 2372-45-4 ]
  • decyl-malonic acid dibutyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With butan-1-ol Erhitzen des Reaktionsprodukts bis auf 165grad;
  • 6
  • [ 106-18-3 ]
  • [ 112-53-8 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: butyl laurate With polyethylsiloxane at 100℃; for 24h; Stage #2: With sodium hydroxide In tetrahydrofuran for 3h; Heating;
  • 7
  • [ 112-41-4 ]
  • [ 1120-36-1 ]
  • [ 872-05-9 ]
  • [ 821-95-4 ]
  • [ 2437-56-1 ]
  • [ 13360-61-7 ]
  • [ 201230-82-2 ]
  • [ 71-36-3 ]
  • [ 10580-24-2 ]
  • [ 106-18-3 ]
  • [ 28267-31-4 ]
  • [ 110-36-1 ]
  • [ 111-06-8 ]
  • [ 35996-97-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine at 160℃; for 24h; 1.a CO2(CO)8 (260 mg) was dissolved in 1-butanol (15 ml) and pyridine (4 ml) and heated under CO (80 bar) in a 50 ml autoclave to 160° C. The olefin/paraffin mixture C10-C15 (10 ml, pre-mixed as described above) was injected using CO (100 bar) and CO was fed at this pressure for 24 h. Olefin conversion >99%.Using an Agilent Pona GC-column (50 m×0.20 mm×0.50 μsn; 40° C. for 5 minutes, 10° C./minute to 300° C., 300° C. for 20 minutes) which separates mainly on differential boiling points, the reaction mixture containing all the butyl C11-C16 esters and residual C10-C15 paraffins, was injected and the resulting GC trace provided an indication that all the C10-C15 paraffins could be separated via distillation from the C11-C16 esters, i.e. the C15 paraffin has a lower boiling point than the C11 esters (see FIG. 2).The paraffins were then removed from the reaction mixture via fractional vacuum distillation (see FIG. 3).The C11-C16 butyl esters were then converted to the corresponding alcohols using LiAlH4 as reducing agent (see FIG. 4). This is a non-catalytic alternative to ester H2/catalyst hydrogenation.
  • 8
  • [ 10580-24-2 ]
  • [ 106-18-3 ]
  • [ 28267-31-4 ]
  • [ 110-36-1 ]
  • [ 111-06-8 ]
  • [ 35996-97-5 ]
  • [ 112-42-5 ]
  • [ 629-76-5 ]
  • [ 112-53-8 ]
  • [ 112-70-9 ]
  • [ 112-72-1 ]
  • [ 36653-82-4 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride 1.a CO2(CO)8 (260 mg) was dissolved in 1-butanol (15 ml) and pyridine (4 ml) and heated under CO (80 bar) in a 50 ml autoclave to 160° C. The olefin/paraffin mixture C10-C15 (10 ml, pre-mixed as described above) was injected using CO (100 bar) and CO was fed at this pressure for 24 h. Olefin conversion >99%.Using an Agilent Pona GC-column (50 m×0.20 mm×0.50 μsn; 40° C. for 5 minutes, 10° C./minute to 300° C., 300° C. for 20 minutes) which separates mainly on differential boiling points, the reaction mixture containing all the butyl C11-C16 esters and residual C10-C15 paraffins, was injected and the resulting GC trace provided an indication that all the C10-C15 paraffins could be separated via distillation from the C11-C16 esters, i.e. the C15 paraffin has a lower boiling point than the C11 esters (see FIG. 2).The paraffins were then removed from the reaction mixture via fractional vacuum distillation (see FIG. 3).The C11-C16 butyl esters were then converted to the corresponding alcohols using LiAlH4 as reducing agent (see FIG. 4). This is a non-catalytic alternative to ester H2/catalyst hydrogenation.
  • 9
  • [ 141-32-2 ]
  • [ 7003-75-0 ]
  • [ 999-55-3 ]
  • [ 106-18-3 ]
YieldReaction ConditionsOperation in experiment
45.1 %Chromat. With 15percent (w/w) Candida antarctica lipase B immobilised onto macroporous acrylic resin at 50℃; for 1h; Enzymatic reaction;
  • 10
  • [ 1956-11-2 ]
  • [ 71-36-3 ]
  • [ 106-18-3 ]
YieldReaction ConditionsOperation in experiment
With induced mycelium-bound lipase from Aspergillus niger MYA 135 In hexane; acetone at 37℃; for 1h; Enzymatic reaction;
  • 11
  • [ 2146-71-6 ]
  • [ 71-36-3 ]
  • [ 106-18-3 ]
YieldReaction ConditionsOperation in experiment
98% With carbon dioxide at 46.02℃; for 3.5h; High pressure; Supercritical conditions; Green chemistry; 2.3.3.2.4. Synthesis of laurate esters in SC-CO2 General procedure: The enzymatic synthesis of citronellyl laurate esters was carried out in 50 mL high pressure reactor vessel. The instrument was equipped with the pressure reading controller and regulator model JASCO-PU-2080-CO2 plus. At first, given amount of vinyl laurate was added followed by addition of given amount of citronellol in the 50 mL reaction vessel. Finally, the reaction was started by addition of immobilized PVA/CHI lipase and the reactor vessel was closed appropriately and assembled to SC-CO2 high pressure reactor. The liquid SC-CO2 was pumped inside the reactor vessel with a flowrate of 3.5 mL/min. The reaction was conducted at given pressure (MPa) and temperature (°C) designed by RSM software for given period. After, the completion of reaction, the SC-CO2 was slowly depressurized through a thermostat restrictor having temperature 50°C which leaves back the residual reaction mass inside the reactor by leaving CO2. The reaction mass was then analyzed using the Perkin-Elmer, Clarus-400 Gas Chromatography (GC) equipped with a flame ionizing detector (FID) and capillary column. The oven temperature of GC was kept at 90°C for 4 min and then rises at 10°C/min up to 240°C. The product formed was also confirmed by the gas-chromatography-mass spectroscopy analysis (GC-MS) by Shimadzu QP-2010 instrument.
With immobilized Candida antarctica lipase B In toluene at 60℃; for 16h; Green chemistry; Enzymatic reaction;
  • 12
  • [ 111-82-0 ]
  • [ 71-36-3 ]
  • [ 106-18-3 ]
YieldReaction ConditionsOperation in experiment
With zinc(II) acetylacetonate; lithium iodide Reflux; 13 EXAMPLE 13 [0074] Reaction of Methyl Laurate with Butanol A 500 ml flask equipped with a stirrer and distillation column was charged with 62.5 g (0.29 mol) of methyl laurate, 162 g (2.19 mol) of n-butanol, 3.8 g (15 mmol) of Zn(acac)2 and 1 g (7.5 mmol) of LiI. The mixture was heated to reflux at atmospheric pressure while methanol was removed from the upper part of the column. The temperature of the oil bath was kept at 130° C. and the reaction was continued in this manner for five hours. On completion of the reaction, excess butanol was distilled off and a clear, yellow oil was obtained. Gas-liquid chromatographic analysis showed full conversion of methyl laurate to butyl laurate.
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