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124-19-6

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124-19-6 Usage

Safety Profile

A severe skin irritant.Combustible liquid. Mutation data reported. When heatedto decomposition it emits acrid smoke and irritatingfumes.

Check Digit Verification of cas no

The CAS Registry Mumber 124-19-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 4 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 124-19:
(5*1)+(4*2)+(3*4)+(2*1)+(1*9)=36
36 % 10 = 6
So 124-19-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3

124-19-6 Well-known Company Product Price

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  • TCI America

  • (N0296)  Nonanal  >95.0%(GC)

  • 124-19-6

  • 25mL

  • 125.00CNY

  • Detail
  • TCI America

  • (N0296)  Nonanal  >95.0%(GC)

  • 124-19-6

  • 100mL

  • 390.00CNY

  • Detail
  • TCI America

  • (N0296)  Nonanal  >95.0%(GC)

  • 124-19-6

  • 500mL

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (A15908)  Nonanal, 97%   

  • 124-19-6

  • 100g

  • 538.0CNY

  • Detail
  • Alfa Aesar

  • (A15908)  Nonanal, 97%   

  • 124-19-6

  • 500g

  • 2385.0CNY

  • Detail

124-19-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name nonanal

1.2 Other means of identification

Product number -
Other names FEMA 2782

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:124-19-6 SDS

124-19-6Synthetic route

Methyl oleate
112-62-9

Methyl oleate

A

nonan-1-al
124-19-6

nonan-1-al

B

methyl ester of azelaic acid aldehyde
1931-63-1

methyl ester of azelaic acid aldehyde

Conditions
ConditionsYield
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;
oct-1-ene
111-66-0

oct-1-ene

carbon monoxide
201230-82-2

carbon monoxide

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With 2-pyridylpropylimine rhodium(I)chlorocarbonyl; hydrogen In toluene at 95℃; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave; chemoselective reaction;100%
With hydrogen In dichloromethane at 45℃; under 51716.2 Torr; for 16h; Autoclave; Inert atmosphere; Green chemistry; regioselective reaction;100%
With hydrogen In cyclohexane at 120℃; under 37503.8 Torr; for 4h; Autoclave;99%
C57H110O12

C57H110O12

A

nonan-1-al
124-19-6

nonan-1-al

B

C30H50O9
7328-03-2

C30H50O9

Conditions
ConditionsYield
With sodium periodate In 1,4-dioxane; water at 20℃; for 1h;A n/a
B 100%
2-octene
111-67-1

2-octene

carbon monoxide
201230-82-2

carbon monoxide

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 15001.5 Torr; for 12h; Autoclave; Green chemistry; regioselective reaction;99.5%
With hydrogen; 4,5-bis(9-dibenzo[b,d]phospholyl)-2,7-di-tert-butyl-9,9-dimethylxanthene; (2,2,6,6-tetramethyl-3,5-heptanedionate)Rh(CO)2 In toluene at 80℃; under 15001.2 Torr; for 1h; Yield given;
With hydrogen; 2,2'-bis(di(3,4,5-F-phenyl)phosphanylmethyl)-1,1'-binaphthyl; acetylacetonatodicarbonylrhodium(l) In methoxybenzene; toluene at 120℃; under 7500.6 Torr; for 16h;
nonyl alcohol
143-08-8

nonyl alcohol

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With 4-methoxy-TEMPO; sodium hypochlorite; potassium bromide In dichloromethane; water at 0℃; for 0.05h; Mechanism; Product distribution; pH = 8.6; other primary and secondary alcohols, var. temp., time, pH, and catalytic species;98%
With tert.-butylhydroperoxide In water at 60℃; for 3h;98%
With 4-methoxy-TEMPO; sodium hypochlorite; potassium bromide In dichloromethane; water at 0℃; for 0.05h; pH = 8.6;92%
2-(n-Octyl)-1,3-dithiane
39854-46-1

2-(n-Octyl)-1,3-dithiane

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With tri(p-tolyl)amine; lithium perchlorate; sodium hydrogencarbonate In water; acetonitrile at 20℃; electrolysis;97%
With periodic acid In tetrahydrofuran; diethyl ether for 0.0833333h; Ambient temperature;91%
1,2-decanediol
1119-86-4

1,2-decanediol

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In dichloromethane at 25℃; for 2.5h; Inert atmosphere;97%
With sodium periodate; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 1.5h;
With N-Bromosuccinimide; (oxybis(2,1-phenylene))bis(diphenylbismuthane); potassium carbonate In [D3]acetonitrile at 23℃; for 1h; Schlenk technique;70 %Spectr.
1-[1-(tert-butyl-dimethyl-silanyloxy)-nonyl]-1H-imidazole

1-[1-(tert-butyl-dimethyl-silanyloxy)-nonyl]-1H-imidazole

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 20℃;96%
epoxidized methyl oleate
2566-91-8

epoxidized methyl oleate

A

nonan-1-al
124-19-6

nonan-1-al

B

methyl ester of azelaic acid aldehyde
1931-63-1

methyl ester of azelaic acid aldehyde

Conditions
ConditionsYield
With periodic acid In diethyl etherA n/a
B 95%
With periodic acid for 0.05h; Product distribution; Ambient temperature;
Multi-step reaction with 2 steps
1: sulfuric acid / acetic acid; acetonitrile; water / 16 h / 20 °C
2: sodium periodate; sodium hydrogencarbonate / acetic acid; acetonitrile; water / 1.5 h / 20 °C
View Scheme
1-Decene
872-05-9

1-Decene

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With oxygen; ozone; 4-methylmorpholine N-oxide In dichloromethane at 0℃;94%
With ozone; 4-methylmorpholine N-oxide In dichloromethane at 0 - 20℃;94%
With sodium periodate; 1,4-diazobicyclo<2.2.2>octane quaternized with chloromethylated styrene-divinylbenzene copolymer*OsO4 In 1,4-dioxane; water for 0.5h; Ambient temperature;100 % Chromat.
Formic acid (E)-non-1-enyl ester
113388-45-7

Formic acid (E)-non-1-enyl ester

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water for 23h; Ambient temperature;94%
oct-1-ene
111-66-0

oct-1-ene

carbon monoxide
201230-82-2

carbon monoxide

A

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With hydrogen In cyclohexane at 120℃; under 37503.8 Torr; for 3h; Autoclave;A 93%
B 7%
With hydrogen; 1-octyl-3-methyl-imidazolium bromide In water at 100℃; under 15001.5 Torr; for 3h; Product distribution; Further Variations:; Reagents; reaction time;A 91.5%
B 5.7%
With hydrogen In n-heptane; toluene at 90℃; under 37503.8 Torr; for 20h;A n/a
B 91%
2-methyl-undec-2-ene
56888-88-1

2-methyl-undec-2-ene

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With ozone In dichloromethane at -78℃;93%
With ozone In dichloromethane at -78℃;93%
2-octyl-1,3-dioxolane
5432-30-4

2-octyl-1,3-dioxolane

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With sulfuric acid for 10h; Ambient temperature;92%
With ammonium cerium(IV) nitrate In methanol; water at 20℃; for 0.166667h; Ring cleavage;91%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
oct-1-ene
111-66-0

oct-1-ene

carbon monoxide
201230-82-2

carbon monoxide

A

nonan-1-al
124-19-6

nonan-1-al

B

octane
111-65-9

octane

C

2-octene
111-67-1

2-octene

Conditions
ConditionsYield
With (acetylacetonato)dicarbonylrhodium (l); 2,2'-bis((dipyrrolylphosphinooxy)methyl)-1,1'-(±)-biphenyl; hydrogen In toluene at 80℃; under 11251.1 Torr; for 1h; Pressure; Reagent/catalyst; Temperature; regioselective reaction;A 91.9%
B n/a
C n/a
1,1-dimethoxynonane
18824-63-0

1,1-dimethoxynonane

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;91%
With guanidine hydrochloride; acetyl chloride for 3h; Ambient temperature;85%
With diphosphorus tetraiodide; propene In dichloromethane at 20℃; for 0.2h;64%
trimethylsilyloxy-nonane
18388-84-6

trimethylsilyloxy-nonane

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; HZSM-5 zeolite In water for 0.133333h; microwave irradiation;91%
With chromium(VI) oxide In pyridine; dichloromethane at 0℃; for 1h;
2-Octyl-[1,3]oxathiane

2-Octyl-[1,3]oxathiane

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With periodic acid In tetrahydrofuran; diethyl ether for 0.166667h; Ambient temperature;90%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

nonan-1-al
124-19-6

nonan-1-al

B

azelaic acid semialdehyde
2553-17-5

azelaic acid semialdehyde

Conditions
ConditionsYield
Stage #1: cis-Octadecenoic acid With ozone In dichloromethane at -78℃;
Stage #2: With dimethylsulfide In dichloromethane at 20℃; for 3h;
A n/a
B 90%
Stage #1: cis-Octadecenoic acid With ozone at 95℃;
Stage #2: With hydrogen at 30℃; under 3750.38 Torr; palladium-coated film reactor;
A n/a
B 48.7%
With 1-carboxymethyl-3-methylimidazol-3-ium hydrogen sulfate; dihydrogen peroxide at 5℃; for 5h;
Multi-step reaction with 3 steps
1: [((S,S)-N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine)FeII(OTf)2]; dihydrogen peroxide / acetonitrile / 2.5 h / 0 °C
2: sulfuric acid / acetonitrile; water / 16 h / 20 °C
3: sodium periodate; sodium hydrogencarbonate / acetonitrile; water / 1.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; potassium permanganate / water / 0.25 h / 0 - 50 °C
2: sodium periodate; tetra(n-butyl)ammonium hydrogen sulfate / water; dichloromethane / 20 °C
View Scheme
formaldehyd
50-00-0

formaldehyd

oct-1-ene
111-66-0

oct-1-ene

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In water; toluene at 90℃; for 0.5h; Microwave irradiation; Sealed vial;90%
octadec-9-enoic acid methyl ester
112-62-9

octadec-9-enoic acid methyl ester

A

nonan-1-al
124-19-6

nonan-1-al

B

methyl ester of azelaic acid aldehyde
1931-63-1

methyl ester of azelaic acid aldehyde

Conditions
ConditionsYield
With ozone; triphenylphosphine In dichloromethane at -78℃; for 24h; Inert atmosphere;A 90%
B 75%
With ozone; potassium iodide In water; tert-butyl alcohol for 1h;
Stage #1: octadec-9-enoic acid methyl ester With oxygen; ozone In neat (no solvent) at 25℃;
Stage #2: With 5%-palladium/activated carbon; hydrogen at 20℃; for 1h; Solvent; Temperature;
1-fluorononanyl trifluoromethanesulfonate

1-fluorononanyl trifluoromethanesulfonate

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With dimethyl sulfoxide at 20℃; for 17h;90%
13,14-dihydroxy-behenic acid
616-01-3

13,14-dihydroxy-behenic acid

A

nonan-1-al
124-19-6

nonan-1-al

B

13-oxotridecanoic acid
65157-88-2

13-oxotridecanoic acid

Conditions
ConditionsYield
With sodium periodate; phosphoric acid; sodium carbonateA 61.5%
B 89%
With sodium periodate; sodium hydrogencarbonate In water; acetic acid; acetonitrile at 20℃; for 24h;
nonanal semicarbazone
16742-11-3

nonanal semicarbazone

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With K-10 clay-supported Fe(NO3)3 ("clayfen" reagent) In dichloromethane for 1.16667h; Ambient temperature;89%
1-nonyne
3452-09-3

1-nonyne

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With water; ruthenium-based phosphine complex In acetone at 120℃; for 26h;89%
With [CpRu(6-Ph2P-Py-2-yl)(MeCN)][PF6(1-)]; water In acetone at 70℃; for 3h;99.9 % Spectr.
With water; [cyclopentadienylruthenium(II) bis(2-diphenylphosphino-6-t-butylpyridine)(acetonitrile)]CF3SO3 In acetone at 70℃; Kinetics;
methyl 9-hydroxy-10-oxostearate
4444-91-1

methyl 9-hydroxy-10-oxostearate

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With 3-butyl-4,5-dimethylthiazol-3-ium trifluoromethanesulfonate; potassium carbonate at 180℃; under 7.50075 Torr; Inert atmosphere;88%
nonanoic acid methyl ester
1731-84-6

nonanoic acid methyl ester

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
With diisobutylaluminium hydride In dichloromethane at -78℃; for 0.5h; Inert atmosphere;88%
trans-2-Octene
13389-42-9

trans-2-Octene

carbon monoxide
201230-82-2

carbon monoxide

A

nonan-1-al
124-19-6

nonan-1-al

B

2-ethylheptanal
27649-40-7

2-ethylheptanal

Conditions
ConditionsYield
With zinc 5,10,15,20-tetraphenylporphyrin; N-ethyl-N,N-diisopropylamine; tri(pyridin-3-yl)phosphine; acetylacetonatodicarbonylrhodium(l) In toluene at 25℃; for 73h; Product distribution; Further Variations:; Catalysts; Temperatures;A 0.7%
B 87.8%
C 9.4%
D 0.5%
With 25,26,27,28-tetrakis(hydroxy)calix[4]arene; hydrogen; phosphan; acetylacetonatodicarbonylrhodium(l) In water at 140℃; under 30003 Torr; for 12h; Product distribution;
With (acetylacetonato)dicarbonylrhodium (l); rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline; hydrogen In toluene at 80℃; under 15001.5 Torr; for 90h; Reagent/catalyst; Autoclave;
trans-4-Octene
14850-23-8

trans-4-Octene

dichloromethane
75-09-2

dichloromethane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
Stage #1: trans-4-Octene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triphenylphosphine; chlorobis(ethylene)rhodium(I) dimer In dichloromethane for 0.5h;
Stage #2: dichloromethane With n-butyllithium In tetrahydrofuran at -78 - 20℃;
Stage #3: With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 0 - 20℃;
86%
cis-2-octene
7642-04-8

cis-2-octene

dichloromethane
75-09-2

dichloromethane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

nonan-1-al
124-19-6

nonan-1-al

Conditions
ConditionsYield
Stage #1: cis-2-octene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triphenylphosphine; chlorobis(ethylene)rhodium(I) dimer In dichloromethane for 0.5h;
Stage #2: dichloromethane With n-butyllithium In tetrahydrofuran at -78 - 20℃;
Stage #3: With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 0 - 20℃;
86%
nonan-1-al
124-19-6

nonan-1-al

nonyl alcohol
143-08-8

nonyl alcohol

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In methanol; diethyl ether for 4h; Reduction; Heating;100%
With hydrogenchloride; tetrahydrogenoboratebis(triphenylphosphine)copper(I) In dichloromethane94%
With hydrogenchloride; samarium In tetrahydrofuran at 20℃;94%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

nonan-1-al
124-19-6

nonan-1-al

1-Benzotriazol-1-yl-nonan-1-ol
111507-85-8

1-Benzotriazol-1-yl-nonan-1-ol

Conditions
ConditionsYield
at 25℃;100%
nonan-1-al
124-19-6

nonan-1-al

3-bromo-3,3-difluropropene
420-90-6

3-bromo-3,3-difluropropene

3,3-difluorododec-1-en-4-ol

3,3-difluorododec-1-en-4-ol

Conditions
ConditionsYield
With indium In water at 20℃; for 3h; Addition;100%
With indium In N,N-dimethyl-formamide for 3h; Ambient temperature;93%
nonan-1-al
124-19-6

nonan-1-al

N-benzyl-N-(1-octynyl)-p-toluenesulfonamide
496922-59-9

N-benzyl-N-(1-octynyl)-p-toluenesulfonamide

(E)-1-[benzyl(p-toluenesulfonyl)amino]-2-hexyl-1-undecen-3-ol

(E)-1-[benzyl(p-toluenesulfonyl)amino]-2-hexyl-1-undecen-3-ol

Conditions
ConditionsYield
Stage #1: N-benzyl-N-(1-octynyl)-p-toluenesulfonamide With titanium(IV) isopropylate; isopropylmagnesium chloride
Stage #2: nonan-1-al
Stage #3: With hydrogen cation Acid hydrolysis; Further stages.;
100%
nonan-1-al
124-19-6

nonan-1-al

diphenyl acetylene
501-65-5

diphenyl acetylene

N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide
205885-39-8

N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide

N-benzyl-N-[(1E,3E)-5-hydroxy-3,4-diphenyl-1,3-tridecadien-1-yl]-p-toluenesulfonamide

N-benzyl-N-[(1E,3E)-5-hydroxy-3,4-diphenyl-1,3-tridecadien-1-yl]-p-toluenesulfonamide

Conditions
ConditionsYield
Stage #1: diphenyl acetylene With titanium(IV) isopropylate; isopropylmagnesium bromide In diethyl ether at -78 - -50℃; for 2.5h;
Stage #2: N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide In diethyl ether at -50℃; for 4h;
Stage #3: nonan-1-al In diethyl ether at -50 - 20℃;
100%
Multistep reaction.;100%
nonan-1-al
124-19-6

nonan-1-al

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

5-hydroxy-3-oxo-tridecanoic acid methyl ester

5-hydroxy-3-oxo-tridecanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h;
Stage #3: nonan-1-al In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h;
100%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 5℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; mineral oil at 5℃; for 0.166667h;
Stage #3: nonan-1-al In tetrahydrofuran; mineral oil at 5 - 10℃; for 0.5h;
nonan-1-al
124-19-6

nonan-1-al

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-octylidene-p-toluenesulfonamide

N-octylidene-p-toluenesulfonamide

Conditions
ConditionsYield
With anthranilic acid In dichloromethane at 60℃; for 24h; Molecular sieve;100%
nonan-1-al
124-19-6

nonan-1-al

(3S)-5,7-dimethoxy-4-methyl-3-(1-oxopropyl)phthalide

(3S)-5,7-dimethoxy-4-methyl-3-(1-oxopropyl)phthalide

(3R)-3-(1-hydroxynonyl)-5,7-dimethoxy-4-methyl-3-propionylphthalide

(3R)-3-(1-hydroxynonyl)-5,7-dimethoxy-4-methyl-3-propionylphthalide

Conditions
ConditionsYield
Stage #1: (3S)-5,7-dimethoxy-4-methyl-3-(1-oxopropyl)phthalide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: nonan-1-al In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
100%
nonan-1-al
124-19-6

nonan-1-al

nonanoic acid
112-05-0

nonanoic acid

Conditions
ConditionsYield
With Oxone In N,N-dimethyl-formamide at 20℃; for 3h;99%
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In water; acetone at 22℃; for 1.5h; Oxidation;86%
With NAD; Geotrichum candidum aldehyde dehydrogenase In aq. buffer at 40℃; for 3h; pH=7.2; Green chemistry; Enzymatic reaction;43%
nonan-1-al
124-19-6

nonan-1-al

Methyl phenyl sulfone
3112-85-4

Methyl phenyl sulfone

(S)-1-Benzenesulfonyl-decan-2-ol
86653-09-0

(S)-1-Benzenesulfonyl-decan-2-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran99%
nonan-1-al
124-19-6

nonan-1-al

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

undec-1-en-3-ol
35329-42-1

undec-1-en-3-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere;99%
With magnesium bromide diethyl etherate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;90%
In tetrahydrofuran 1.) RT, overnight, 2.) reflux, 6 h;84%
nonan-1-al
124-19-6

nonan-1-al

3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one
50603-71-9

3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one

methyl 3-heptylazulene-1-carboxylate

methyl 3-heptylazulene-1-carboxylate

Conditions
ConditionsYield
With morpholine In ethanol for 4h; Heating;99%
nonan-1-al
124-19-6

nonan-1-al

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(+/-)-1-trimethylsilyl-1-undecyn-3-ol
74794-25-5, 132958-42-0, 61077-68-7

(+/-)-1-trimethylsilyl-1-undecyn-3-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -75 - -10℃; for 0.5h; Inert atmosphere;
Stage #2: nonan-1-al In tetrahydrofuran; hexane at -78 - 20℃; for 1h;
99%
With ethylmagnesium bromide In tetrahydrofuran for 2h; Heating;74%
With n-butyllithium In tetrahydrofuran; hexane 1.) -85 deg C, 15 min, 2.) -85 deg C to 0 deg C, 2 h;
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: nonan-1-al In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
nonan-1-al
124-19-6

nonan-1-al

4-<11C>cyanobutylidene(triphenyl)phosphorane
159085-03-7

4-<11C>cyanobutylidene(triphenyl)phosphorane

C13(11)CH25N

C13(11)CH25N

Conditions
ConditionsYield
With 1,2-dichloro-benzene at 140 - 170℃; for 0.166667h;99%
nonan-1-al
124-19-6

nonan-1-al

allyltributylstanane
24850-33-7

allyltributylstanane

Conditions
ConditionsYield
With 4-nitro-benzoic acid In acetonitrile at 25℃; for 10h;99%
With cerium(III) chloride; sodium iodide In acetonitrile at 20℃; for 22h;91%
With aluminum oxide; cerium(III) chloride; sodium iodide at 50℃; for 18h;85%
nonan-1-al
124-19-6

nonan-1-al

methyl 9-hydroxy-10-oxostearate
4444-91-1

methyl 9-hydroxy-10-oxostearate

Conditions
ConditionsYield
With 1,3-dimethylbenzimidazolium Iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 3h; Heating;99%
With C15H22N3O2(1+)*Cl(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0℃; for 5h; Inert atmosphere;79%
With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine In ethanol at 80℃; for 4h;73%
nonan-1-al
124-19-6

nonan-1-al

1-Bromo-2-butyne
3355-28-0

1-Bromo-2-butyne

3-Methyl-dodeca-1,2-dien-4-ol
78808-47-6

3-Methyl-dodeca-1,2-dien-4-ol

Conditions
ConditionsYield
indium In water Ambient temperature;99%
With gallium; indium In tetrahydrofuran at 25℃; for 1h;75%
nonan-1-al
124-19-6

nonan-1-al

diallylmercury
2097-71-4

diallylmercury

Conditions
ConditionsYield
In water Ambient temperature;99%
nonan-1-al
124-19-6

nonan-1-al

hydrogen cyanide
74-90-8

hydrogen cyanide

2-amino-6-methylphenol
17672-22-9

2-amino-6-methylphenol

1-(2-hydroxy-6-methylphenyl)amino-3-methylbutane-1-carbonitrile
220184-55-4

1-(2-hydroxy-6-methylphenyl)amino-3-methylbutane-1-carbonitrile

Conditions
ConditionsYield
((R)-3,3'-dibromo-1,1'-bi-2-naphtholato){Zr(CN)(N-methylimidazole)((R)-6,6'-dibromo-1,1'-bi-2-naphtholato)}2 In dichloromethane at -45℃; 5 mol % catalyst;99%
((R)-3,3'-dibromo-1,1'-bi-2-naphtholato){Zr(CN)(N-methylimidazole)((R)-6,6'-dibromo-1,1'-bi-2-naphtholato)}2 In dichloromethane at -45℃; 5 mol % catalyst;94%
nitrostyrene
5153-67-3

nitrostyrene

nonan-1-al
124-19-6

nonan-1-al

(R)-2-((S)-2-nitro-1-phenylethyl)nonanal

(R)-2-((S)-2-nitro-1-phenylethyl)nonanal

Conditions
ConditionsYield
With N,N-dimethylbenzylamine prolinol trimethylsilyl ether; benzoic acid In water at 20℃; for 22h; Michael addition; optical yield given as %ee; enantioselective reaction;99%
With N,N-dimethylbenzylamine prolinol trimethylsilyl ether; C15H19N2O2(1+)*F6P(1-) In water at 20℃; for 20h; Michael condensation; optical yield given as %ee; enantioselective reaction;98%
Stage #1: nonan-1-al With C16H27N5OSi; sodium hydrogencarbonate In sodium chloride at 20℃; for 0.166667h; Michael addition;
Stage #2: nitrostyrene In sodium chloride at 20℃; for 48h; Michael addition; optical yield given as %ee; diastereoselective reaction;
59%
nonan-1-al
124-19-6

nonan-1-al

nitromethane
75-52-5

nitromethane

(R)-(-)-1-nitro-2-decanol

(R)-(-)-1-nitro-2-decanol

Conditions
ConditionsYield
With C36H44N4O4S2; copper(I) bromide In methanol at 20℃; for 36h; Henry reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
With C13H24Cl2CuN2; triethylamine In tetrahydrofuran; nitromethane at -20℃; for 49h; Henry Nitro Aldol Condensation; enantioselective reaction;98%
With (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride In di-isopropyl ether at 0℃; for 20h; Henry reaction; optical yield given as %ee; enantioselective reaction;75%
With C19H17N; copper(l) chloride In 1,2-dichloro-ethane at 0℃; for 48h; Henry reaction; optical yield given as %ee; enantioselective reaction;72%
nonan-1-al
124-19-6

nonan-1-al

N-(1,1-diphenyl-3-butenyl)amine
356762-89-5

N-(1,1-diphenyl-3-butenyl)amine

1,1-diphenyl-N-(undec-1-en-4-yl)methanimine

1,1-diphenyl-N-(undec-1-en-4-yl)methanimine

Conditions
ConditionsYield
at 20℃; for 6h; Aza-Cope Rearrangement; Molecular sieve;99%
furan
110-00-9

furan

nonan-1-al
124-19-6

nonan-1-al

<1(R,S),5(R,S)>-6(R,S)-n-octyl-2,7-dioxabicyclo<3.2.0>hept-3-ene
92622-43-0

<1(R,S),5(R,S)>-6(R,S)-n-octyl-2,7-dioxabicyclo<3.2.0>hept-3-ene

Conditions
ConditionsYield
at -20℃; for 9.5h; Irradiation;98.6%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

nonan-1-al
124-19-6

nonan-1-al

1-(benzotriazol-1-yl)-1-chlorononane
111120-68-4

1-(benzotriazol-1-yl)-1-chlorononane

Conditions
ConditionsYield
With thionyl chloride In chloroform for 0.5h; Heating;98%
nonan-1-al
124-19-6

nonan-1-al

1,3-butanediol
24621-61-2

1,3-butanediol

(2R,4S)-4-methyl-2-octyl-1,3-dioxane
90457-76-4

(2R,4S)-4-methyl-2-octyl-1,3-dioxane

Conditions
ConditionsYield
98%

124-19-6Relevant articles and documents

Hydroformylation of internal olefins to linear aldehydes with novel rhodium catalysts

Van Der Veen, Lars A.,Kamer, Paul C.J.,Van Leeuwen, Piet W. N. M.

, p. 336 - 338 (1999)

Unprecedented high activities and selectivities were observed in the hydroformylation of internal octenes to linear products using rhodium catalysts with rigid diphosphane ligands. Dibenzophosphole 1 and a phenoxaphosphane analogue with bite angles of 120 and 119°, respectively, are suited for this.

Efficient hydroformylation in dense carbon dioxide using phosphorus ligands without perfluoroalkyl substituents

Koeken, Ard C. J.,Benes, Nieck E.,Van Den Broeke, Leo J. P.,Keurentjes, Jos T. F.

, p. 1442 - 1450 (2009)

Rhodium catalysts modified with triphenylphosphine, triphenyl phosphite, and tris(2,4-ditrrt-butylphenyl) phosphite have been evaluated for their performance in the hydroformylation of 1octene using carbon dioxide as the solvent. It is demonstrated that these catalysts are very efficient for the hydroformylation in carbon dioxide, although they are not designed for use in this medium. In particular, the catalyst prepared in situ from dicarbonyl(2,4-pentanedione)rhodium(I) and tris(2,4-di-tert-butyl-phenyl) phosphite gave rise to an initial turnover frequency in excess of 3x 10 4 molaldehyde molRh h-1. Such a reaction rate is unprecedented for hydroformylation in supercritical carbon dioxide-rich reaction mixtures.

Hsing,Chang

, p. 3589 (1939)

A facile method for promoting activities of ordered mesoporous silica-anchored Rh-P complex catalysts in 1-octene hydroformylation

Zhou, Wei,He, Dehua

, p. 1146 - 1154 (2009)

This work deals with the promotion of immobilized Rh catalyst activities in olefin hydroformylation by lengthening the alkyl spacers and choosing an active Rh precursor. The flexibility of long chain alkyls was used to free the motion of the anchored Rh c

-

Goosen,Laue

, p. 383 (1969)

-

Room-temperature production of bio-based aldehydes from vegetable oil-derived epoxide: via H2WO4?Al-MCM-41 as recyclable catalyst

Peng, Libo,Xie, Qinglong,Nie, Yong,Liu, Xuejun,Lu, Meizhen,Ji, Jianbing

, p. 23061 - 23070 (2019)

The oxidative cleavage of vegetable oils and their derivatives to produce bio-based aldehydes is a potentially useful process, although the aldehyde products are readily oxidized to carboxylic acids and thus seldom obtained in high yields. The present study developed a room-temperature method for the synthesis of bio-aldehydes via the oxidative cleavage of vegetable oil-derived epoxides, using H2WO4 as the catalyst, H2O2 as the oxidant, and t-BuOH as the solvent. Reactions were carried out at temperatures ranging from 25 to 35 °C for 3.5-10.5 h, and provided >99% conversion and >90% aldehyde yield. In particular, an approximately 97% yield was obtained at 25 °C after 10.5 h. As the reaction proceeded, the H2WO4 dissolved to form a W-containing anion. Several mesoporous Al-MCM-41 materials having different Si/Al ratios were hydrothermally synthesized and used as adsorbents to recover the catalyst by adsorbing these anions. The adsorption capacity of the Al-MCM-41 was found to increase with decreases in the Si/Al ratio. The Al-MCM-41 had little effect on the oxidative cleavage reaction at 25 °C, and thus could be directly added to the reaction system. The excellent anion adsorption performance of the Al-MCM-41 greatly improved the reusability of the H2WO4 catalyst. When using the Al-MCM-41 with the best adsorption performance, there was no significant decrease in the activity of the catalyst following five reuses.

Mediated electrolysis of vicinal diols by neocuproine palladium catalysts

Lybaert,Tehrani, K. Abbaspour,De Wael

, p. 685 - 691 (2017)

Synthetic electrochemistry agrees well with the principles of sustainable chemistry, therefore it is considered as a more environmentally friendly approach than some current synthetic methods. Here, we present a new strategy for the chemoselective oxidation of vicinal diols, viz. the integration of neocuproine palladium catalysts and electrosynthesis. Benzoquinones are used as an effective mediator as the reduced species (hydroquinones) can be easily reoxidized at relative low potentials at an electrode surface. NeocuproinePd(OAc)2 efficiently works as a catalyst in an electrolysis reaction for vicinal diols at room temperature. This is a remarkable observation given the fact that aerobic oxidation reactions of alcohols typically need a more complex catalyst, i.e. [neocuproinePdOAc]2[OTf]2. In this article we describe the optimization of the electrolysis conditions for the neocuproinePd(OAc)2 catalyst to selectively oxidize diols. The suggested approach leads to conversion of alcohols with high yields and provides an interesting alternative to perform oxidation reactions under mild conditions by the aid of electrochemistry.

Reactivity of platinum stanna-closo-dodecaborate complexes: First hydroformylation studies

Wesemann, Lars,Hagen, Siegbert,Marx, Thiemo,Pantenburg, Ingo,Nobis, Markus,Driessen-Hoelscher, Birgit

, p. 2261 - 2265 (2002)

The synthesis and characterization of two (dppp)Pt complexes with the stannaborate ligand SnB11H11 is described. In the case of the salt [Bu3MeN]2[(dppp)Pt (SnB11H11)2] the struc

Highly regioselective and active Rh-2,2′-bis(dipyrrolylphosphinooxy)- 1,1′-(±)-binaphthyl catalyst for hydroformylation of 2-octene

Liu, Wenjing,Yuan, Maolin,Fu, Haiyan,Chen, Hua,Li, Ruixiang,Li, Xianjun

, p. 596 - 597 (2009)

Rhodium catalyst bearing 2,2′-bis(dipyrrolyphosphinooxy)-1,1′- (±)-binaphthyl (ligand 1) shows high regioselectivity and activity for the hydroformylation of 2-octene. The introduction of a pyrrolyl group in the ligand greatly improves the yield of the linear aldehyde. The regioselectivity is up to 97.5% under mild conditions (100 °C, 0.7 MPa H2/CO). Copyright

Heterometallic catalysts. Cobalt carbonyl derivatives of lanthanides in catalysis of octene-1 hydroformylation

Beletskaya, I.P.,Magomedov, G.K.-I.,Voskoboinikov, A.Z.

, p. 289 - 295 (1990)

The results of an investigation involving the catalysis of octene-1 hydroformylation with heterobimetallic catalysts, cobalt carbonyl derivatives of lanthanides, are reported.

Realistic energy surfaces for real-world systems: An IMOMO CCSD(T):DFT scheme for rhodium-catalyzed hydroformylation with the 6-dppon ligand

Gellrich, Urs,Himmel, Daniel,Meuwly, Markus,Breit, Bernhard

, p. 16272 - 16281 (2013)

The hydroformylation of terminal alkenes is one of the most important homogeneously catalyzed processes in industry, and the atomistic understanding of this reaction has attracted enormous interest in the past. Herein, the whole catalytic cycle for rhodium-catalyzed hydroformylation with the 6-diphenylphosphinopyridine-(2H)-1-one (6-DPPon) ligand 1 was studied. This catalytic transformation is challenging to describe computationally, since two requirements must be met: 1) changes in the hydrogen-bond network must be modeled accurately and 2) bond-formation/bond-breaking processes in the coordination sphere of the rhodium center must be calculated accurately. Depending on the functionals used (BP86, B3LYP), the results were found to differ strongly. Therefore, the complete cycle was calculated by using highly accurate CCSD(T) computations for a PH3 model ligand. By applying an integrated molecular orbital plus molecular orbital (IMOMO) method consisting of CCSD(T) as high level and DFT as low-level method, excellent agreement between the two functionals was achieved. To further test the reliability of the calculations, the energetic-span model was used to compare experimentally derived and computed activation barriers. The accuracy of the new IMOMO method apparently makes it possible to predict the catalytic potential of real-world systems. Copyright

Amphiphilic Resin-Supported Rhodium-Phosphine Catalysts for C-C Bond Forming Reactions in Water

Uozumi, Yasuhiro,Nakazono, Maki

, p. 274 - 277 (2002)

Amphiphilic resin-supported rhodium-phosphine complexes were prepared on polystyrene-poly(ethylene glycol) graft co-polymer (1% DVB cross-linked) beads. The immobilized rhodium complexes exhibited high catalytic activity in water to promote hydroformylation of 1-alkenes, [2+2+2] cyclotrimerization of internal alkynes forming benzene rings, and 1,4-addition of arylboronic acids.

Selectivity of rhodium-catalyzed hydroformylation of 1-octene during batch and semi-batch reaction using trifluoromethyl-substituted ligands

Koeken, Ard C. J.,Van Vliet, Michiel C. A.,Van Den Broeke, Leo J. P.,Deelman, Berth-Jan,Keurentjes, Jos T. F.

, p. 179 - 188 (2008)

The regioselectivity of catalysts generated in situ from dicarbonyl rhodium(I)(2,4-pentanedione) and trifluoromethyl-substituted triphenylphosphine ligands has been evaluated during the hydroformylation of 1-octene. The influence of batch or semi-batch operation, the solvent, and the number of trifluoromethyl substituents has been investigated. During batch operation in a supercritical carbon dioxide (CO2)-rich system the differential n:iso ratio increases from approximately 4 to a value of 12-16 at about 90-95% conversion for the catalyst based on bis[3,5-bis(trifluoromethyl)phenyl] phenylphosphine. For semi-batch conditions using hexane a constant n:iso ratio is obtained over a broad conversion range. Batch hydroformylation in neat 1-octene is faster than in a supercritical CO2-rich, one-phase system, with a similar overall selectivity as observed in the supercritical case. The results provide further directions for the development of ligands that are especially designed for the separation of homogeneous catalysts in continuously operated hydroformylation in ScCO2.

Cobalt N-heterocyclic carbene alkyl and acyl compounds: Synthesis, molecular structure and reactivity

Llewellyn, Simon A.,Green, Malcolm L. H.,Cowley, Andrew R.

, p. 4164 - 4168 (2006)

The N-heterocyclic-carbene containing cobalt carbonyl compound [Co(IMes)(CO)3(Me)] (IMes = 1,3-bis(2,4,6-trimethylphenyl)-imidazol- 2-ylidene), 1, has been synthesised by tertiary phosphine displacement from [Co(PPh3)(CO)3(Me)]. Subsequent carbonylation afforded the acyl derivative [Co(IMes)(CO)3(COMe)], 2. Similarly, the compound [Co(IMes)(CO)3(COEt)], 3, has been synthesised. The compounds 2 and 3 have been shown to react with dihydrogen to form the cobalt hydride compound [Co(IMes)(CO)3(H)], 4. The molecular structures of compounds 1 and 2 have been determined. The Royal Society of Chemistry 2006.

Rhodium(I) Ferrocenylcarbene Complexes: Synthesis, Structural Determination, Electrochemistry, and Application as Hydroformylation Catalyst Precursors

Ramollo, G. Kabelo,López-Gómez, María J.,Liles, David C.,Matsinha, Leah C.,Smith, Gregory S.,Bezuidenhout, Daniela I.

, p. 5745 - 5753 (2015)

New examples of the rare class of rhodium(I) ferrocenyl Fischer carbene complexes 1-8, [Rh(LL)Cl{C(XR)Fc}] [LL = cod, (CO)2, (CO, PR3) (R = Ph, Cy or OPh), and (CO, AsPh3); XR = OEt or NHnPr] were prepared, and the electronic effects of coligands and alkoxy vs aminocarbene substituents were investigated by spectroscopic and electrochemical methods. The molecular structures of complexes 1, 2, and 4-6 were confirmed by single-crystal X-ray diffraction. The use of the complexes 1-8 as homogeneous catalysts for the hydroformylation of 1-octene was demonstrated, and the influence of the carbene substituents and coligands on the activity and regioselectivity of the catalysts evaluated. Finally, the stability of the Rh-Ccarbene bond of complex 1 under hydroformylation conditions was confirmed with 13C NMR experiments.

Linear amphiphilic TEMPO-grafted poly(ether sulfone) as polymeric interfacial catalyst: Synthesis, self-assembly behavior, and application

Chen, Liang,Tang, Jun,Zhang, Qi,Wang, Jianli

, p. 134 - 139 (2016)

In this study, we report the development of a novel recyclable polymer-supported interfacial catalyst for Montanari oxidation. The catalyst was prepared by immobilization of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) on poly(ether sulfone) (PES) bridged by imidazole groups and characterized by 1H nuclear magnetic resonance (NMR) spectroscopy, Fourier transform infrared (FTIR) spectroscopy, elemental analysis, contact angle measurement, and transmission electron microscopy (TEM). This well-designed polymer was self-assembled into nanoaggregates in CH2Cl2. It was then used as Pickering emulsifier in Montanari oxidation system (NaClO/NaBr/immobilized TEMPO) for selective oxidation of different alcohols, which exhibited higher activity due to the enhanced mass transfer through microreactor mechanism. Moreover, this polymeric interfacial catalyst was pH-sensitive and could be easily recycled by adding small amount of acid, and subsequent cycles of alcohol oxidation showed no loss on either conversion or selectivity. This study represents an innovative approach for developing polymeric interfacial catalyst.

Reaction Activity and Selectivity as a Function of Solution Ionic Strength in Oct-1-ene Hydroformylation with Sulfonated Phosphines

Ding, Hao,Hanson, Brian E.

, p. 2747 - 2748 (1994)

Salt concentration has a considerable influence on the activity and selectivity of water-soluble hydroformylation catalysts derived from Rh(acac)(CO)2 and the sulfonated phosphine, P3; addition of Na2SO4 or Na2HPO4 to the catalysts enhances the both the rate and selectivity of the hydroformylation reaction.

High pressure infrared and nuclear magnetic resonance studies of the rhodium-sulfoxantphos catalysed hydroformylation of 1-octene in ionic liquids

Silva, Silvana M.,Bronger, Raymond P. J.,Freixa, Zoraida,Dupont, Jairton,Van Leeuwen, Piet W. N. M.

, p. 1294 - 1296 (2003)

The rhodium-sulfoxantphos catalysed hydroformylation of 1-octene in 1-n-butyl-3-methylimidazoliuni hexafluorophosphate (BMI·PF6) as a room temperature ionic liquid was monitored in situ by high pressure IR (HP-IR) and NMR (HP-NMR). Similar ee (bis-equatorial) and ea (equatorial-apical) (diphosphine)Rh(CO)2H catalytic species, as observed in organic solvents, are formed in the BMI·PF6 ionic liquid. The ratio of the ee and ea isomers is influenced by both the temperature and syngas pressure. An increase in hydrogen partial pressure has no effect on the activity of the system during the reaction performed in BMI:PF6, while some hydroformylation systems using xanthene backbone ligands in conventional organic solvents can be sensitive to hydrogen partial pressure.

β-Cyclodextrin-Modified Diphosphanes as Ligands for Supramolecular Rhodium Catalysts

Reetz, Manfred T.,Waldvogel, Siegfried R.

, p. 865 - 867 (1997)

-

Continuous, selective hydroformylation in supercritical carbon dioxide using an immobilised homogeneous catalyst

Meehan,Sandee,Reek,Kamer,Van Leeuwen,Poliakoff

, p. 1497 - 1498 (2000)

A continuous process for the selective hydroformylation of higher olefins in supercritical carbon dioxide (scCO2) is presented; the catalyst shows high selectivity and activity over several hours and no decrease in performance was observed over several days.

Silica gel supported ferric nitrate: A convenient oxidizing reagent

Khadilkar, Bhushan,Borkar, Shobha

, p. 207 - 212 (1998)

A silica gel supported ferric nitrate was prepared by co-grinding Fe(NO3)3.9H2O with silica gel in appropriate amounts. The reagent was used in equimolar quantity to oxidize various alcohols to corresponding aldehydes with complete selectivity. Similarly it successfully oxidizes various Hantzsch-type 1,4-dihydropyridines.

-

Narasaka et al.

, p. 3724 (1972)

-

Continuous flow homogeneous catalysis using supercritical fluids

Webb, Paul B.,Cole-Hamilton, David J.

, p. 612 - 613 (2004)

The continuous flow hydroformylation of 1-octene catalysed by Rh/[RMIM][Ph2PC6H4SO3] (R = 1-propyl, 1-pentyl or 1-octyl) dissolved only in the steady state reaction mixture and using scCO2 as a transport vector for both substrates and products gives rates up to 160-240 catalyst turnovers h-1 with low rhodium leaching over a 12 h period at a total pressure of 125-140 bar.

Mechanistic insights into a supramolecular self-assembling catalyst system: Evidence for hydrogen bonding during rhodium-catalyzed hydroformylation

Gellrich, Urs,Seiche, Wolfgang,Keller, Manfred,Breit, Bernhard

, p. 11033 - 11038 (2012)

The structural integrity and flexibility provided by intermolecular hydrogen bonds leads to the outstanding properties of the 6- diphenylphosphinopyridin-(2H)-1-one ligand (see scheme) in the rhodium-catalyzed hydroformylation of terminal alkenes, as demonstrated by the combination of spectroscopic methods and DFT computations. Hydrogen bonds were also detected in a competent intermediate of the catalytic cycle. Copyright

Preparation of Polymer Supported Phosphine Ligands by Metal Catalyzed Living Radical Copolymerization and Their Application to Hydroformylation Catalysis

Cardozo, Andres F.,Manoury, Eric,Julcour, Carine,Blanco, Jean-Francois,Delmas, Henri,Gayet, Florence,Poli, Rinaldo

, p. 1161 - 1169 (2013)

A series of well-defined polystyrene-supported tertiary phosphine ligands were prepared by copper-catalyzed atom transfer radical polymerization (ATRP), involving direct copolymerization of styrene and 4-diphenylphosphinostyrene (or 4-styryldiphenylphosphine, SDPP). Copolymerization of the two monomers at different molar ratios showed a decreasing level of control as the SDPP molar fraction (fSDPP) increased. A satisfactory level of control was achieved for fSDPP≤0.25 such that there was a constant concentration of growing living chains , and linear Mn growth with conversion and low dispersity. Copper-free polymers with different chain lengths were prepared and tested as polymeric ligands in the rhodium-catalyzed hydroformylation of 1-octene. The polymeric ligands yielded higher linear/branched selectivity and lower activity relative to PPh3 at the same P/Rh ratio. The selectivity increased slightly as a function of the polymer chain length.

Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water

Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David

, (2021/11/30)

Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.

Bio-derived nanosilica-anchored Cu(II)-organoselenium complex as an efficient retrievable catalyst for alcohol oxidation

Gogoi, Rajjyoti,Borah, Geetika

, (2021/09/13)

A new copper(II) complex supported onto rice-husk-derived nanosilica was prepared from 2,6-bis((phenylselanyl)methyl)pyridine, salicylaldehyde and copper acetate monohydrate, Cu(OAc)2·H2O. The as-synthesized complex Cu(II)SeNSe@imine-nanoSiO2 (Complex I) was extensively characterized with FT-IR, powder XRD, SEM-EDX, solid-state UV-Vis, ESR, XPS, TGA and BET surface area analysis. The catalytic activity of the complex was explored for alcohol oxidation reactions using H2O2 as oxidant and acetonitrile as solvent. For comparison, we have also prepared an analogous homogeneous catalyst (Complex II) and characterized it with FT-IR, UV-Vis, LC-MS and ESR analyses. Its catalytic activity was also screened to the same reaction. The immobilized catalyst showed better efficiency with 75%–95% isolated yield compared with the homogeneous one for alcohol oxidation with at least five times recyclability without profound loss in activity.

ALDEHYDE GENERATION VIA ALKENE HYDROFORMYLATION

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Paragraph 0035; 0079-0081, (2021/09/26)

Aldehyde generation includes providing a first input stream, a second input, and an alkene substrate to a reactor system. The first input stream includes a catalyst, a ligand, and an organic solvent. The second input stream includes a mixture of carbon monoxide (CO) and hydrogen gas (H2). The alkene substrate is in either gaseous form or liquid form, the liquid form of the alkene substrate being provided with the first input stream, the gaseous form of the alkene substrate being provided with the second input stream. The reactor system includes a first reactor and a second reactor, where the second reactor is gas permeable and positioned within the first reactor.

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