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Showing posts with label africa. Show all posts
Showing posts with label africa. Show all posts

Tuesday 21 July 2015

Adamantanylideneadamantane


Adamantanylideneadamantane [30541-56-1]

94
NameAdamantanylideneadamantane
Synonyms
Name in Chemical AbstractsTricyclo[3.3.1.1(3,7)]decane, tricyclo[3.3.1.1(3,7)]decylidene-
CAS No30541-56-1
EINECS No
Molecular formulaC20H28
Molecular mass268.45
SMILES codeC1(=C6C4CC5CC(C4)CC6C5)C2CC3CC(C2)CC1C3
2-Adamantanone
TiCl4 / Zn / THF
reacts to

Adamantanylideneadamantane ; Side reactions

1H-NMR

1H NMR
1H-NMR: crude product
500 MHz, CDCl3
delta [ppm]mult.atomsassignment
1.63-1.69m8 HCH2
1.79-1.86m12 HCH2
1.90m4 H5-H, 5'-H, 7-H, 7'-H
2.88m4 H1-H, 1'-H, 3-H, 3'-H
7.26

CHCl3





1H NMR
1H-NMR: Adamantanylideneadamantane
500 MHz, CDCl3
delta [ppm]mult.atomsassignment
1.63-1.69m8 HCH2
1.79-1.86m12 HCH2
1.90m4 H5-H, 5'-H, 7-H, 7'-H
2.88m4 H1-H, 1'-H, 3-H, 3'-H
7.26

CHCl3




Synthesis of adamantylideneadamantane from adamantanone

Reaction type: McMurry reaction, reductive coupling, alkenesynthesis
Substance classes: ketone, alkene
Techniques: working with cover gas, adding dropwise with a piston-operated pipette, adding dropwise with an addition funnel, stirring with magnetic stir bar, heating under reflux, shaking out, extracting, Abfiltrieren, evaporating with rotary evaporator, recrystallizing, use of an ice cooling bath, heating with oil bath
Degree of difficulty: Difficult
http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/3012_en.pdf


Operating scheme

Operating scheme

0.1 mol 2-Adamantanone
Educts
Amount Risk Safety
2-Adamantanone

15.0 g R no data S 24/25
Reagents
Amount Risk Safety
Titanium tetrachloride
C C
20.3 g R 14-34 S 1/2-7/8-26-36/37/39-45
Zinc powder
F F N N
14.3 g R 15-17-50/53 S 2-43-46-60-61
Solvents
Amount Risk Safety
Tetrahydrofuran
F F Xi Xi
430 mL R 11-19-36/37 S 2-16-29-33
Cyclohexane
F F Xn Xn N N
~250 mL R 11-38-50/53-65-67 S 2-9-16-33-60-61-62
Ethanol
F F

R 11 S 2-7-16
Others
Amount Risk Safety
Potassium carbonate
Xn Xn
~21 g R 22-36/37/38 S 22-26-37/39
Sodium sulfate
Xi Xi
~5 g R 36/37/38 S 26-36


0.1 mol 2-Adamantanone
Products
Amount Risk Safety
Adamantanylideneadamantane

11.4 g R no data S no data
Byproducts
Amount Risk Safety
2-Adamantanol


R no data S 24/25

Waste Disposal
evaporated solvent mixture organic solvents, halogen free
aqueous phase after shaking out solvent water mixtures, containing halogens
sodium sulfate solid waste, free from mercury

0.1 mol 2-Adamantanone
three-necked flask 1000 mL three-necked flask 1000 mL
heatable magnetic stirrer with magnetic stir bar heatable magnetic stirrer with magnetic stir bar
internal thermometer internal thermometer
suction filter suction filter
suction flask suction flask
bubble counter bubble counter
piston-operated pipette piston-operated pipette
protective gas piping protective gas piping
addition funnel with pressure balance addition funnel with pressure balance
separating funnel separating funnel
rotary evaporator rotary evaporator
ice bath ice bath
oil bath oil bath


0.1 mol 2-Adamantanone
Atom economy
48.3 %
Yield
85 %
Target product mass
11.4 g
Sum of input masses
430 g
Mass efficiency
26 mg/g
Mass index
38 g input / g product
E factor
37 g waste / g product

Chromatogram

crude product chromatogram
GC: crude product
columnSE-54, L= 25 m, ID 0.32 mm, DF 0.25 µm (Macherey & Nagel)
inletGerstel KAS, injector: 250°C, split injection 1:20, 0.1 µL
carrier gasN2, pre-column pressure 62 kPa, 1.04 mL/min
oven100 °C (1 min), 10 °C/min --> 250 °C (30 min)
detectorFID, 275 °C
integrationpercent concentration calculated from relative peak area

pure product chromatogram
GC: pure product
columnSE-54, L= 25 m, ID 0.32 mm, DF 0.25 µm (Macherey & Nagel)
inletGerstel KAS, injector: 250°C, split injection 1:20, 0.1 µL
carrier gasN2, pre-column pressure 62 kPa, 1.04 mL/min
oven100 °C (1 min), 10 °C/min --> 250 °C (30 min)
detectorFID, 275 °C
integrationpercent concentration calculated from relative peak area

13C-NMR

13C NMR
13C-NMR: crude product
125 MHz, CDCl3
delta [ppm]assignment
28.6C5, C5', C7, C7'
31.9C1, C1', C-3, C3'
37.3C6, C6'
39.6C4, C4', C8, C8', C9, C9', C10, C10'
133.1C2, C2'
76.5-77.5CDCl3



13C NMR
13C-NMR: Adamantanylideneadamantane
125 MHz, CDCl3
delta [ppm]assignment
28.6C5, C5', C7, C7'
31.9C1, C1', C-3, C3'
37.3C6, C6'
39.6C4, C4', C8, C8', C9, C9', C10, C10'
133.1C2, C2'
76.5-77.5CDCl3












IR

IR
IR: crude product
[KBr, T%, cm-1]
[cm-1]assignment
2966, 2916aliph. C-H valence
2848aliph. C-H valence



IR
IR: Adamantanylideneadamantane
[KBr, T%, cm-1]
[cm-1]assignment
2966, 2916aliph. C-H valence
2848aliph. C-H valence





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कि औरों का भला हो जाये।




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