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123-38-6 Usage

Chemical Description

Propionaldehyde is an organic compound with the formula CH3CH2CHO.

Description

Propionaldehyde is a volatile liquid substance which consists of one carbonyl group and its characteristic functional group. The main functional group is an aldehyde which classifies propionaldehyde in the carbonyls. The main trunk of this substance is a short aliphatic chain. The carbonyl group determines, to a large extent, its chemical properties and most importantly its nucleophilic property. Propionaldehyde is readily oxidized if in contact to oxygen and should therefore be stored under inert gases.

Chemical Properties

Propionaldehyde has a characteristic sharp and pungent odor similar to acetaldehyde.It undergoes reactions typical for the low molecular weight aldehydes, which, because of the terminal carbonyl group, are very reactive. Contamination or the exposure to elevated temperatures may induce a hazardous polymerization. Propionaldehyde is a colorless, flammable liquid with a suffocating fruity odor. It is used as Intermediate for the chemical industry, for example for the manufacture of pharmaceuticals, pesticides, perfumes and plastics.

Occurrence

Reported found in apple aroma and in the essential oils of camphor, Rosa centifolia, clary sage, Pinus excelsa and Pinus silverstris. Also reported found in over 100 natural products including apple, banana, sweet cherry, sour cherry, black currant grapes, melon, pineapple, strawberry, cabbage, carrot, celery, cucumber, garlic, onion, leek, potato, peas, rutabaga, tomato, Scotch spearmint oil, vinegar, bread and bread preferment, blue cheeses, cheddar cheese, Swiss cheese, butter, milk, cream, boiled egg, caviar, fatty fish, cooked turkey, beef, pork and chicken, beer, rum, cognac, whiskies, grape wines, coffee, cocoa, tea, roasted filberts and peanuts, peanut oil, potato chips, pecans, oats, honey, soybeans, Arctic bramble, beans, Bantu beer, plum brandy, cauliflower, Brussels sprouts, rice, prickly pear, peated malt, clary sage, truffle, krill, oysters, loganberry, Chinese quince and maté.

Uses

Different sources of media describe the Uses of 123-38-6 differently. You can refer to the following data:
1. Manufacture of propionic acid, polyvinyl, and other plastics; synthesis of rubber chemicals; disin- fectant; preservative.
2. Propionaldehyde is produced by the oxo reaction of ethylene with carbon monoxide and hydrogen. n-Propyl alcohol is produced by hydrogenation of propionaldehyde, and propionic acid is made by oxidation of propionaldehyde. n-Propyl alcohol is used as solvent in printing inks and as an intermediate in the preparation of agricultural chemicals. Propionic acid is used as a grain preservative as, for example, in preventing spoilage of wet corn used as animal feed. The use of propionic acid as a grain preservative is an alterna tive to drying by heating, which consumes fuel, and is considered mostly when fuel is expensive.
3. Propionaldehyde is used in the productionof propionic acid, propionic anhydride, andmany other compounds. It is formed in theoxidative deterioration of corn products, suchas corn chips. It occurs in automobile exhaustgases.

Definition

ChEBI: An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.

Preparation

Different sources of media describe the Preparation of 123-38-6 differently. You can refer to the following data:
1. By oxidation of propyl alcohol, or by dry distillation of barium propionate with calcium formate.
2. Propionaldehyde is prepared in the usual way by the oxidation of n-propyl alcohol. It can also be prepared by dehydrogenating the alcohol by passing the vapors over a heated copper or brass catalyst. This avoids the danger of further oxidation to propionic acid. The reactions of propionaldehyde are practically like those of acetaldehyde. It must be remembered that only the two alpha hydrogen atoms are active in replacement and condensation reactions.

General Description

A clear colorless liquid with an overpowering fruity-like odor. Less dense than water. Flash point 15°F. Vapors are heavier than air.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Propionaldehyde may form explosive peroxides. Reacts vigorously with oxidizing agents. Explosive in the form of vapor when exposed to heat or flame [Lewis]. Incompatible with strong bases and strong reducing agents. Vigorous polymerization reaction with methyl methacrylate. Polymerization may also occur in the presence of acids or caustics .

Hazard

Flammable, dangerous fire risk, explosive limits in air 3.0–16%. Upper respiratory tract irri- tant.

Health Hazard

Propionaldehyde is a mild irritant to humanskin and eyes. The irritation effect from40 mg was severe in rabbits’ eyes. The toxicityof this compound observed in test animalswas low. Subcutaneous administration in ratsexhibited the symptoms of general anestheticeffect, convulsion, and seizure. Inhalationtoxicity was determined to be low. A concentrationof 8000 ppm (19,000 mg/m3) inair was lethal to rats.LD50 value, oral (rats): 1400 mg/kgLD50 subcutaneous (rats): 820 mg/kg.

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic by skin contact, ingestion, and subcutaneous routes. Mddly toxic by inhalation. A skin and severe eye irritant. Flammable liquid. Dangerous fire hazard when exposed to heat or flame; reacts vigorously with oxidizers. Explosive in the form of vapor when exposed to heat or flame. Vigorous polymerization reaction with methyl methacrylate. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Potential Exposure

Used as a synthetic flavoring; as a disinfectant and preservative; to make propionic acid; in plastic and rubber manufacturing; to make alkyl resins and plasticizers.

Carcinogenicity

In a mutagenic test in V79 cells, Eder et al. observed that propionaldehyde is not mutagenic at 1 mM, but is toxic at 2mM. Similar to acrolein, Eder et al. suggested that the mutagenicity of this compound is mediated by its bifunctionality, whereas its cytotoxicity is mediated by the aldehyde function.

Shipping

UN1275 Propionaldehyde, Hazard Class: 3; Labels: 3-Flammable liquid. Propionaldehyde is readily oxidized if in contact to oxygen and should therefore be stored under inert gases.

Purification Methods

the aldehyde with CaSO4 or CaCl2, and fractionally distil it under nitrogen or in the presence of a trace of hydroquinone (to retard oxidation). Blacet and Pitts [J Am Chem Soc 74 3382 1952] repeatedly distilled the middle fraction in a vacuum until it no longer gave a solid polymer when cooled to -80o. It is stored with CaSO4. [Beilstein 1 IV 3165.]

Incompatibilities

Incompatible with strong acids; amines. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoa- cids, epoxides. Strong caustics; reducing agents can cause explosive polymerization. Can self-ignite if finely dispersed on porous or combustible material, such as fabric. Heat or UV light can cause decomposition. Aldehydes are fre- quently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are gener- ated by the combination of aldehydes with azo, diazo com- pounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (anti- oxidants) to shipments of aldehydes retards autoxidation

Waste Disposal

Propionaldehyde is destroyed by burning in achemical incinerator equipped with an afterburnerand scrubber. Permanganate oxidationis a suitable laboratory method of destruction.

Check Digit Verification of cas no

The CAS Registry Mumber 123-38-6 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 3 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 123-38:
(5*1)+(4*2)+(3*3)+(2*3)+(1*8)=36
36 % 10 = 6
So 123-38-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H6O/c1-2-3-4/h3H,2H2,1H3

123-38-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A16146)  Propionaldehyde, 97%   

  • 123-38-6

  • 500ml

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (A16146)  Propionaldehyde, 97%   

  • 123-38-6

  • 1000ml

  • 307.0CNY

  • Detail
  • Alfa Aesar

  • (A16146)  Propionaldehyde, 97%   

  • 123-38-6

  • 5000ml

  • 1233.0CNY

  • Detail
  • Sigma-Aldrich

  • (538124)  Propionaldehyde  reagent grade, 97%

  • 123-38-6

  • 538124-250ML

  • 837.72CNY

  • Detail
  • Sigma-Aldrich

  • (538124)  Propionaldehyde  reagent grade, 97%

  • 123-38-6

  • 538124-1L

  • 1,692.99CNY

  • Detail

123-38-6SDS

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 propanal

1.2 Other means of identification

Product number -
Other names Propionaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Propionaldehyde is used in the manufacture of plastics, in the synthesis of rubber chemicals, and as a disinfectant and preservative.
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:123-38-6 SDS

123-38-6Synthetic route

allyl alcohol
107-18-6

allyl alcohol

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
(sulphos)Rh(CO)2 In octane; water at 100℃; for 1h; Product distribution; Further Variations:; Solvents; autoclave;100%
With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); silver(I) 4-methylbenzenesulfonate In toluene at 60℃; for 6h; Inert atmosphere;100%
With [Ru(η3:η3-C10H16)Cl2(benzimidazole)] In glycerol at 75℃; for 12h; Sealed tube; Inert atmosphere; Green chemistry;99%
acrolein
107-02-8

acrolein

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With hydrogen; palladium(II) complex of ferrocenylamine sulfide (2) In acetone under 4137.2 Torr; for 1h; or with catalyst 3, 2 h;100%
With hydrogen; Ni/AlPO4-SiO2; nickel In methanol at 47.9℃; for 0.666667h;100%
With 2%Pd/Al2O3; hydrogen; palladium In water at 150℃; under 3750.38 Torr;85%
hydrogen
1333-74-0

hydrogen

acrolein
107-02-8

acrolein

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With C61H62ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 8h; Reagent/catalyst; Time;100%
propan-1-ol
71-23-8

propan-1-ol

A

propionaldehyde
123-38-6

propionaldehyde

B

propionic acid
802294-64-0

propionic acid

Conditions
ConditionsYield
With potassium hydroxide at 50℃; electrolysis;A n/a
B 99%
With C30H24N2O7W; dihydrogen peroxide In water; acetonitrile for 12h; Reflux;A 64%
B 23%
palladium at 50℃; for 4h; electrooxydation on Pt-Rh-electrode;A 19.5%
B 17%
ethene
74-85-1

ethene

carbon monoxide
201230-82-2

carbon monoxide

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
propylamine; di(rhodium)tetracarbonyl dichloride In ethanol at 110℃; under 50 Torr; for 1h;99%
With ; hydrogen In N,N-dimethyl-formamide at 100℃; under 42753.4 Torr; for 4.5h; Product distribution; other alkene; selectivity of the hydroformylation;74%
With hydrogen; silica gel; palladium var. Pd dispersion;
4-(1-propenyloxymethyl)-1,3-dioxalan-2-one

4-(1-propenyloxymethyl)-1,3-dioxalan-2-one

A

4-hydroxymethyl-1,3-dioxolan-2-one
931-40-8

4-hydroxymethyl-1,3-dioxolan-2-one

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With water; dichloro bis(acetonitrile) palladium(II) at 40℃; for 2h;A 99%
B n/a
propan-1-ol
71-23-8

propan-1-ol

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With tetrahexylammonium tetrakis(diperoxomolybdo)phosphate In chloroform at 40℃; for 48h;98%
With C19H20N3O2Ru(2+)*2F6P(1-) In aq. buffer at 24.84℃; for 1h; pH=1.8; Thermodynamic data; Activation energy; Reagent/catalyst;95%
With cetyltrimethylammonium bromochromate In dichloromethane for 2h; Heating;92%
1-Chloropropane
540-54-5

1-Chloropropane

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With C30H38Cl2Ir2N4 In dimethyl sulfoxide at 50℃; for 5h;95%
With oxygen; kieselguhr; copper(l) chloride In dichloromethane for 1.5h; Oxidation; Heating;91%
propan-1-ol
71-23-8

propan-1-ol

[closo-3,3-(triphenylphosphine)2-3-HSO4-3,1,2-RhC2B9H11] tetrahydrofuran solvate
82807-94-1

[closo-3,3-(triphenylphosphine)2-3-HSO4-3,1,2-RhC2B9H11] tetrahydrofuran solvate

A

closo-3,3-(PPh3)2-3-H-3,1,2-RhC2B9H11
53687-46-0

closo-3,3-(PPh3)2-3-H-3,1,2-RhC2B9H11

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
In propan-1-ol byproducts: H2SO4; under Ar, Rh complex suspended in 1-propanol, suspn. heated to 50°C in water bath for 10 min; ppt. filtered off, washed three times with ethanol and twice with diethyl ether, air-dried;A 94%
B n/a
vinyl benzoate
583-04-0

vinyl benzoate

A

propionaldehyde
123-38-6

propionaldehyde

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; diethylene glycol dimethyl ether; 1,6-bis(diphenylphosphino)hexane; water In 1,2-dimethoxyethane; dichloromethane at 20 - 85℃; for 0.666667h; Inert atmosphere;A 89 %Chromat.
B 94%
n-propyl nitrite
543-67-9

n-propyl nitrite

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With dimethyl sulfoxide at 70℃; for 6h;92.21%
With boron trifluoride diethyl etherate In diethyl ether for 4h; Ambient temperature;91%
at 130 - 150℃;
trans-n-PrOIr(CO)(PPh3)2
94070-39-0

trans-n-PrOIr(CO)(PPh3)2

A

carbonylhydridotris(triphenylphosphine)iridium(I)
33541-67-2

carbonylhydridotris(triphenylphosphine)iridium(I)

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With triphenylphosphine In toluene soln. of Ir complex and PPh3 (.approx. 2-3 equiv.) in toluene allowed to stir at 70°C for several hours; org. products detected by gas chromy.;A n/a
B 92%
2-methylpropenal
78-85-3

2-methylpropenal

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
Stage #1: 2-methylpropenal With morpholine; TEMPOL In water for 0.5h;
Stage #2: With formaldehyd In water at 20 - 70℃; for 1.08h; Reagent/catalyst;
90.8%
1,1-diacetoxy-1-ethyl methane
33931-80-5

1,1-diacetoxy-1-ethyl methane

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With caro's acid; silica gel In dichloromethane for 5h; Heating;90%
With N-sulfonic acid poly(4-vinylpyridinium) chloride In methanol at 20℃; for 0.416667h;90%
With N-Bromosuccinimide; water; silica gel at 20℃; for 0.05h; neat (no solvent); chemoselective reaction;87%
diethyl(2,2'-bipyridyl)nickel(II)
15218-76-5

diethyl(2,2'-bipyridyl)nickel(II)

A

Ni(CO)2(2,2'-bipyridine)
14917-14-7

Ni(CO)2(2,2'-bipyridine)

B

3,4-hexanedione
4437-51-8

3,4-hexanedione

C

ethene
74-85-1

ethene

D

propionaldehyde
123-38-6

propionaldehyde

E

pentan-3-one
96-22-0

pentan-3-one

Conditions
ConditionsYield
With carbon monoxide In tetrahydrofuran THF, room temp., 0.1 h;A 50%
B 0%
C 0%
D 0%
E 90%
ethylpentacarbonylrhenium
75149-83-6

ethylpentacarbonylrhenium

[D3]acetonitrile
2206-26-0

[D3]acetonitrile

A

Os(CO)4(Re(CO)4(C(2)H3CN))2
98688-87-0

Os(CO)4(Re(CO)4(C(2)H3CN))2

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
In [D3]acetonitrile under N2 flow, EtRe(CO)5 in CD3CN was added via syringe to an NMR tube,the contents were frozen and degassed, H2Os(CO)4 (2 equiv) was added byvac. transfer, reaction was complete in 8 h at 62°C; monitored by (1)H NMR, solvent was removed in vacuo, residue taken up in CH2Cl2, addn. of hexane; organometallic product (presumably Re2Os(CO)12(CD3CN)2) was not obtained pure;A n/a
B 89%
phenyl butyl ketone
1009-14-9

phenyl butyl ketone

A

propionaldehyde
123-38-6

propionaldehyde

B

butyraldehyde
123-72-8

butyraldehyde

C

propionic acid
802294-64-0

propionic acid

D

benzoic acid
65-85-0

benzoic acid

E

butyric acid
107-92-6

butyric acid

Conditions
ConditionsYield
With 5% active carbon-supported ruthenium; water; oxygen; calcium oxide at 100℃; for 12h; Reagent/catalyst; Time;A n/a
B n/a
C n/a
D 89%
E n/a
hydridopentacarbonylrhenium(I)
16457-30-0

hydridopentacarbonylrhenium(I)

ethylpentacarbonylrhenium
75149-83-6

ethylpentacarbonylrhenium

[D3]acetonitrile
2206-26-0

[D3]acetonitrile

A

Re2(CO)9(C(2)H3CN)
98688-84-7

Re2(CO)9(C(2)H3CN)

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
In [D3]acetonitrile under N2 flow EtRe(CO)5 in CD3CN was added via syringe to an NMR tube, the contents were frozen and degassed, and HRe(CO)5 (1:1 ratio) was added via vac. transfer, the tube was sealed and heated (60°C) for 27h; monitored by (1)H NMR, Re2(CO)9(CD3CN) was isolated by preparative layer chromy.; elem. anal., yield of EtCHO was detd. by the integration of the corresponding peak in the (1)H NMR spectrum;A 70%
B 88%
2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)propenal
149935-82-0

2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)propenal

acrolein
107-02-8

acrolein

A

2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)propanal
178745-31-8

2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)propanal

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
Pd on carbonA 87%
B n/a
(C4H9)3SnOCH2CH(CH3)Br

(C4H9)3SnOCH2CH(CH3)Br

A

tributyltin bromide
1461-23-0

tributyltin bromide

B

propionaldehyde
123-38-6

propionaldehyde

C

methyloxirane
75-56-9, 16033-71-9

methyloxirane

Conditions
ConditionsYield
80% decompn. of the crude compound at 150°C (0.5 h);A n/a
B 13%
C 87%
propionic acid
802294-64-0

propionic acid

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With (CH3)2NCH2NpSiH2Ph at 150 - 170℃;85%
Stage #1: propionic acid With 4-methyl-morpholine; 1,3,5-Triazine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride hydrate In tetrahydrofuran; water at 25℃; for 1h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; water at 25℃; under 760.051 Torr; for 19h;
49%
With calcium carbonate at 450 - 500℃;
Trifluoro-methanesulfonate14-(2-hydroxy-propyl)-7-phenyl-5,6,8,9-tetrahydro-dibenzo[c,h]acridinium;
80253-84-5

Trifluoro-methanesulfonate14-(2-hydroxy-propyl)-7-phenyl-5,6,8,9-tetrahydro-dibenzo[c,h]acridinium;

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With 2,4,6-triphenylpyridine at 190℃; under 15 Torr;85%
propylamine
107-10-8

propylamine

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With potassium permanganate; iron(II) sulfate In dichloromethane for 5h; Heating;84%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;80%
With N-Bromosuccinimide; perchloric acid; iridium(III) chloride; mercury(II) diacetate at 35℃; for 72h; Rate constant; Thermodynamic data; energy data: E(act); effect of conc. of reactants;
C13H12N2O
1266113-09-0

C13H12N2O

n-propyl halide

n-propyl halide

A

N-phenylbenzamidine
1527-91-9

N-phenylbenzamidine

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
Stage #1: C13H12N2O; n-propyl halide In diethyl ether at 20℃; Inert atmosphere;
Stage #2: With sodium carbonate In diethyl ether at 20℃; Inert atmosphere;
A n/a
B 84%
hexane-3,4-diol
922-17-8

hexane-3,4-diol

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With sodium hypochlorite In acetonitrile at 20℃; for 0.25h;83%
trans-propenylamine N,N-disiliciee
78108-64-2

trans-propenylamine N,N-disiliciee

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With hydrogenchloride82%
n-propyl halide

n-propyl halide

A

N1,N1-dimethyl-N2-phenylformamidine
1783-25-1

N1,N1-dimethyl-N2-phenylformamidine

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
Stage #1: C9H12N2O; n-propyl halide In diethyl ether at 20℃; Inert atmosphere;
Stage #2: With sodium carbonate In diethyl ether at 20℃; Inert atmosphere;
A n/a
B 82%
propylene glycol
57-55-6

propylene glycol

A

2-ethyl-4-methyl-1,3-dioxolane
4359-46-0

2-ethyl-4-methyl-1,3-dioxolane

B

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With tungsten trioxide on silica; hydrogen In water at 250℃; for 5h; Concentration; Temperature; Inert atmosphere;A 31.7%
B 81.3%
With sulfuric acid In water at 130℃; Thermodynamic data; Kinetics; Activation energy; Further Variations:; Temperatures; reagent concentration; Dehydration; acetalization;
With ferrierite(20) at 300℃; chemoselective reaction;
propylamine
107-10-8

propylamine

propionaldehyde
123-38-6

propionaldehyde

N-propylidenepropylamine
7707-70-2

N-propylidenepropylamine

Conditions
ConditionsYield
In toluene for 1h; Ambient temperature;100%
With potassium hydroxide 1.) 5-8 deg C, 2 h, 2.) room temperature, 30 min;62%
Stage #1: propylamine; propionaldehyde at 0℃; for 1.5h; Inert atmosphere;
Stage #2: With potassium hydroxide at -18℃; for 24h; Inert atmosphere;
29%
1,2-dimethoxybenzene
91-16-7

1,2-dimethoxybenzene

propionaldehyde
123-38-6

propionaldehyde

9,10-diethyl-2,3,6,7-tetramethoxy-anthracene
140648-13-1

9,10-diethyl-2,3,6,7-tetramethoxy-anthracene

Conditions
ConditionsYield
With sulfuric acid; acetonitrile for 0.5h;100%
With sulfuric acid at 5 - 10℃;98%
With sulfuric acid In water at -10℃; for 2h;46%
propionaldehyde
123-38-6

propionaldehyde

propan-1-ol
71-23-8

propan-1-ol

Conditions
ConditionsYield
With hydrogen; mer-Os(PPh3)3HBr(CO) at 150℃; under 22800 Torr; for 1.66667h; Product distribution;100%
With hydrogen; mer-Os(PPh3)3HBr(CO) In toluene at 150℃; under 22800 Torr; for 1.7h;100%
With hydrogen In water at 60℃; under 15001.5 Torr; for 8h; Reagent/catalyst; Autoclave;100%
propionaldehyde
123-38-6

propionaldehyde

(E)-2-methylpent-2-enal
623-36-9

(E)-2-methylpent-2-enal

Conditions
ConditionsYield
With sodium hydroxide In water at 50℃; for 1h;100%
Stage #1: propionaldehyde With pyrrolidine In hexane at 20℃; for 48h;
Stage #2: With hydrogenchloride In hexane; water at 20℃; for 4h; stereoselective reaction;
95%
With pyrrolidine; benzoic acid In pentane at 10℃; for 48h;90%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

propionaldehyde
123-38-6

propionaldehyde

2-<(trimethylsilyl)oxy>butanenitrile
24731-32-6

2-<(trimethylsilyl)oxy>butanenitrile

Conditions
ConditionsYield
With trans-{(iBu)2ATIGeiPr}2Pt(CN)2 In chloroform-d1 at 50℃; for 2h; Catalytic behavior; Schlenk technique; Glovebox;100%
With C29H38AlN4O2(1+)*CF3O3S(1-) at 20℃; for 0.0833333h; Catalytic behavior; Inert atmosphere; Schlenk technique;99%
With C11H8N3O8S(3-)*Fe(3+)*6H2O In methanol at 20℃; for 4h;98.1%
propionaldehyde
123-38-6

propionaldehyde

cyclohexene
110-83-8

cyclohexene

cyclohexyl ethyl ketone
1123-86-0

cyclohexyl ethyl ketone

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
at 27℃; for 22h; (γ-irradiation);
Irradiation;
propionaldehyde
123-38-6

propionaldehyde

2-chloropropanal
683-50-1

2-chloropropanal

Conditions
ConditionsYield
With N-chloro-succinimide; rac-Pro-OH In chloroform at 0 - 20℃;100%
With chlorine In dichloromethane; N,N-dimethyl-formamide at 10℃; for 4h; Reagent/catalyst; Inert atmosphere;87.5%
With sulfuryl dichloride In dichloromethane at -10℃; Reflux; Inert atmosphere;66%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

propionaldehyde
123-38-6

propionaldehyde

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
93498-07-8

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

propionaldehyde
123-38-6

propionaldehyde

1-Benzotriazol-1-yl-propan-1-ol
111507-79-0

1-Benzotriazol-1-yl-propan-1-ol

Conditions
ConditionsYield
at 25℃;100%
3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

propionaldehyde
123-38-6

propionaldehyde

1-ethyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol
14092-31-0

1-ethyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol

Conditions
ConditionsYield
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: propionaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;
100%
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With copper(l) iodide; ethylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 4h; Metallation;
Stage #2: propionaldehyde In tetrahydrofuran at -10 - 20℃; for 14h; Grignard reaction;
86%
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: propionaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
80%
(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

propionaldehyde
123-38-6

propionaldehyde

cyclooctyl-1 propanone-1
85359-51-9

cyclooctyl-1 propanone-1

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

propionaldehyde
123-38-6

propionaldehyde

(methyl-2' cyclohexyl)-1 propanone-1
85995-78-4

(methyl-2' cyclohexyl)-1 propanone-1

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
(S)-1-amino-2-(methoxymethyl)pyrrolidine
59983-39-0

(S)-1-amino-2-(methoxymethyl)pyrrolidine

propionaldehyde
123-38-6

propionaldehyde

[(S)-2-methoxymethylpyrrolidin-1-yl]-N-propylideneamine
70113-32-5

[(S)-2-methoxymethylpyrrolidin-1-yl]-N-propylideneamine

Conditions
ConditionsYield
In diethyl ether at 20℃;100%
With magnesium sulfate In dichloromethane at 20℃; for 12h;89%
With 4 A molecular sieve In dichloromethane79%
(S)-1-amino-2-(methoxymethyl)pyrrolidine
59983-39-0

(S)-1-amino-2-(methoxymethyl)pyrrolidine

propionaldehyde
123-38-6

propionaldehyde

N-[(S)-2-methoxymethylpyrrolidin-1-yl]propan-1-imine
72203-94-2

N-[(S)-2-methoxymethylpyrrolidin-1-yl]propan-1-imine

Conditions
ConditionsYield
at 20℃; for 16h;100%
at 20℃;100%
In dichloromethane at 20℃; for 20h;98%
propionaldehyde
123-38-6

propionaldehyde

ethyl(p-menthene-1-yl-6) cetone
31375-17-4

ethyl(p-menthene-1-yl-6) cetone

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
1-methylcyclopent-1-ene
693-89-0

1-methylcyclopent-1-ene

propionaldehyde
123-38-6

propionaldehyde

(methyl-2' cyclopentyl)-1 propanone-1
81977-75-5

(methyl-2' cyclopentyl)-1 propanone-1

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
Cycloheptene
628-92-2

Cycloheptene

propionaldehyde
123-38-6

propionaldehyde

cycloheptyl-1 propanone-1
89932-42-3

cycloheptyl-1 propanone-1

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
1-methylcycloheptene
1453-25-4

1-methylcycloheptene

propionaldehyde
123-38-6

propionaldehyde

(methyl-2' cycloheptyl)-1 propanone-1
89932-43-4

(methyl-2' cycloheptyl)-1 propanone-1

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
1-methylcyclooctene
15840-64-9

1-methylcyclooctene

propionaldehyde
123-38-6

propionaldehyde

(methyl-2' cyclooctyl)-1 propanone-1
89932-44-5

(methyl-2' cyclooctyl)-1 propanone-1

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
Chlorodifluoromethyl n-hexyl ketone
86340-68-3

Chlorodifluoromethyl n-hexyl ketone

propionaldehyde
123-38-6

propionaldehyde

4,4-difluoro-3-hydroxy-5-undecanone
127894-36-4

4,4-difluoro-3-hydroxy-5-undecanone

Conditions
ConditionsYield
With copper(l) chloride; zinc In tetrahydrofuran for 4h; Heating;100%
Lithium; 4,6-dimethoxy-benzofuran-3-olate

Lithium; 4,6-dimethoxy-benzofuran-3-olate

propionaldehyde
123-38-6

propionaldehyde

2-(1-Hydroxy-propyl)-4,6-dimethoxy-benzofuran-3-one
131403-04-8

2-(1-Hydroxy-propyl)-4,6-dimethoxy-benzofuran-3-one

Conditions
ConditionsYield
at -78℃; for 0.166667h;100%
C6H6O2(2-)*2Li(1+)
142252-83-3

C6H6O2(2-)*2Li(1+)

propionaldehyde
123-38-6

propionaldehyde

2-(1-hydroxypropyl)hexa-3,5-dienoic acid

2-(1-hydroxypropyl)hexa-3,5-dienoic acid

Conditions
ConditionsYield
In tetrahydrofuran Product distribution; Mechanism; regioselectivity of addition; 1.) -70 deg C, 30 min; 2.) 30 deg C, 2 h; further aldehyde, ketones and usaturated ketones;100%
In tetrahydrofuran 1.) -70 deg C, 30 min; 2.) 30 deg C, 2 h;100%
2-<<1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl>thio>-4-(trifluoromethyl)-4,5,5,5-tetrafluoro-1-pentene-1,3-dione
75790-42-0

2-<<1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl>thio>-4-(trifluoromethyl)-4,5,5,5-tetrafluoro-1-pentene-1,3-dione

propionaldehyde
123-38-6

propionaldehyde

2-Ethyl-6-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethylsulfanyl)-[1,3]dioxin-4-one
75782-04-6

2-Ethyl-6-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethylsulfanyl)-[1,3]dioxin-4-one

Conditions
ConditionsYield
100%
100%
propionaldehyde
123-38-6

propionaldehyde

benzil
134-81-6

benzil

2,3-dihydroxy-1,2-diphenyl-1-pentanone

2,3-dihydroxy-1,2-diphenyl-1-pentanone

Conditions
ConditionsYield
With titanium(III) chloride In acetone at 0℃; for 1h;100%
propionaldehyde
123-38-6

propionaldehyde

cyclopentene
142-29-0

cyclopentene

1-cyclopentyl-1-propanone
6635-67-2

1-cyclopentyl-1-propanone

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
propionaldehyde
123-38-6

propionaldehyde

diphenylphosphane
829-85-6

diphenylphosphane

Ph2PCH(OH)Et

Ph2PCH(OH)Et

Conditions
ConditionsYield
at 20℃; neat (no solvent);100%
at -20℃; for 0.25h;92%
propionaldehyde
123-38-6

propionaldehyde

((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-((S)-1-phenyl-ethyl)-amine
175443-13-7

((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-((S)-1-phenyl-ethyl)-amine

((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-((S)-1-phenyl-ethyl)-propyl-amine
175443-11-5

((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-((S)-1-phenyl-ethyl)-propyl-amine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane100%

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123-38-6Relevant articles and documents

Kinetic study of the oxidation of propan-1-ol by alkaline hexacyanoferrate(III) catalyzed by ruthenium trichloride

Mucientes,Poblete,Rodriguez,Santiago

, p. 662 - 668 (1997)

The oxidation kinetics of propan-1-ol by alkaline hexacyanoferrate(III) catalyzed by ruthenium trichloride were studied spectrophotometrically. The initial rate method was used for kinetic analysis. The reaction rate shows a fractional order in [oxidant] and [substrate] and a first-order dependence on [RuCl3]. The dependence on [OH-] is complicated. A reaction mechanism involving two active catalytic species is proposed. Each one of these species forms an intermediate complex with the substrate. The attack of these complexes by hexacyanoferrate(III) in rate-determining step produces a radical species which is further oxidized in the subsequent step.

-

Goetz,Orchin

, p. 1549 (1963)

-

Formation of C3H6 from the Reaction C3H7 + O2 and C2H3Cl from C2H4Cl + O2 at 297 K

Kaiser, E. W.,Wallington, T. J.

, p. 18770 - 18774 (1996)

The generation of conjugate olefins from the reactions of propyl (reaction 1) or chloroethyl (reaction 2) radicals with O2 has been investigated as a function of total pressure (0.4-700 Torr) at 297 +/- 2 K.The experiments were carried out by UV irradiation of mixtures of propane (or ethyl chloride), Cl2, and O2 to generate alkyl radicals.Propylene from reaction 1 was measured by FTIR spectroscopy, while vinyl chloride from reaction 2 was monitored by both FTIR and gas chromatographic analysis.At pressures where the formation of propylperoxy radicals is near the high-pressure limit, the propylene yield from reaction 1 was inversely dependent on total pressure (YC3H6 P-0.68+/-0.03), proving that it is formed via rearrangement of an excited propylperoxy adduct that can also be stabilized by collision.The vinyl chloride yield decreased from 0.3 + /- 0.1 percent at 1 Torr to 0.1 percent at 10 Torr.Because the formation of chloroethylperoxy radicals is in the fall-off region over this pressure range, the vinyl chloride yield cannot be ascribed unambiguously to an addition-elimination process.The propylene yield from reaction 1 is 2-4 times smaller than the ethylene yield from C2H5 + O2 over the pressure range 0.4-100 Torr, while the vinyl chloride yield from reaction 2 is 40 times smaller between 1 and 10 Torr.This is consistent with more efficient stabilization of the excited propylperoxy relative to the ethylperoxy adduct caused by the presence of additional vibrational modes.The markedly smaller ambient temperature vinyl chloride yield from reaction 2 may result from a combination of more efficient stabilization resulting from the lower frequency of the C-Cl bond and reduction of the C-H bond reactivity upon Cl substitution.

A sensitive cataluminescence-based sensor using a SrCO3/graphene composite for n-propanol

Zhang, Qianchun,Meng, Feifei,Zha, Lin,Wang, Xingyi,Zhang, Guoyi

, p. 57482 - 57489 (2015)

In this paper, we developed a cataluminescence-based sensor using SrCO3/graphene for sensitive and selective detection of n-propanol. The composite was characterized by X-ray diffraction, transmission electron microscopy, Fourier transform infrared spectroscopy, and gas adsorption. The sensor was coupled with a miniature vaporizing device to detect n-propanol in liquid samples. The experimental results revealed that the SrCO3/graphene sensor exhibited a sensitivity for n-propanol 5.8 times higher than that of pure SrCO3, indicating that the sensitivity of the SrCO3/graphene sensor was increased by adding graphene to SrCO3. The linear range of the sensor was 0.2 to 32 mg L-1 (r = 0.9987) with a limit of detection of 0.08 mg L-1. The sensor showed a rapid response of 2 s and a recovery time of 20 s, respectively. The sensor was used to analyze samples spiked with known concentrations of n-propanol. The concentrations of n-propanol in all samples were well quantified with satisfactory recoveries, indicating that the SrCO3/graphene sensor is a promising candidate for fast, sensitive, selective detection of n-propanol. We also discuss the possible mechanism based on the reaction products.

Hydrolysis of Aldal Acetals

Su Min Oon,Kubler, Donald G.

, p. 1166 - 1171 (1982)

Eleven aldal acetals were synthesized, and the kinetics of their hydrolyses in water and in water-acetonitrile were studied as model systems for the hydrolysis of sucrose. α,α'-Diethoxypropyl ether (an aldal acetal) hydrolyzes in water without hemiacetal buildup.The reaction is not subject to general acid catalysis and the value of kD3O(+)/kH3O(+) = 2.44, both results being characteristic of an A1 mechanism.The energy of activation for the hydrolysis of α,α'-diethoxydipropyl ether was 84.98 kJ mol -1 in water and showed no temperature dependency over the range of 15 - 35 deg C.The structural effects for the hydrolysis of aldal acetals parallel those for acetal hydrolysis.

Linnemann

, p. 61 (1878)

Dehydration of 1,2-propanediol to propionaldehyde over zeolite catalysts

Zhang, Dazhi,Barri, Sami A.I.,Chadwick, David

, p. 148 - 155 (2011)

Dehydration of 1,2-propanediol has been investigated over a range of zeolite catalysts with different pore structures and acidity. The reaction forms part of a two-step process for the conversion of glycerol to propionaldehyde. The effects of reaction temperature, concentration, space velocity, and SiO 2/Al2O3 ratio have been studied. The medium pore size, unidirectional channel zeolites ZSM-23 and Theta-1 showed high activity and selectivity to propionaldehyde (exceeding 90 wt% at 300-350 °C). Selectivity to the intermolecular dehydration product 2-ethyl-4-methyl-1,3-dioxolane was high at lower temperatures for all the zeolites, but decreased to a low value at higher temperatures and lower GHSV. The results are discussed in relation to the reaction mechanism and zeolite structures. Significant deactivation was observed for higher 1,2-propanediol partial pressures, which was partially mitigated by the addition of steam.

Hydroformylation of Ethylene Catalysed by Ruthenium Complexes Supported on Zeolite

Jackson, Peter F.,Johnson, Brian F. G.,Lewis, Jack,Ganzerla, Renso,Lenarda, Maurizo,Graziani, Mauro

, p. C1 - C4 (1980)

Hydroformylation of ethylene is catalysed by zeolite-supported ruthenium compounds and gives propan-1-al and propan-1-ol as major products.

Highly selective supramolecular catalyzed allylic alcohol isomerization

Leung, Dennis H.,Bergman, Robert G.,Raymond, Kenneth N.

, p. 2746 - 2747 (2007)

A supramolecular tetrahedral assembly Na12[Ga4L6] (L = 1,5-bis-catecholamide naphthalene) has been found to selectively encapsulate monocationic rhodium complexes of the appropriate size and shape. Encapsulation within the chiral environment of the host directly affects the symmetry of the rhodium guest and can be well characterized by NMR spectroscopy. The rhodium complexes were found to be catalytically active for the isomerization of allylic alcohols. Investigations into the catalytic activity of the encapsulated rhodium guests have shown that the constrained cavity of the host exerts a strong influence on the reactivity at the metal center. The supramolecular host prevents substrates of the wrong size and shape from entering the host cavity and reacting with the encapsulated metal center, while substrates of the correct dimensions are allowed ready access. These results suggest that the metal center remains in the active site of the host while reactants and products freely and rapidly access the host cavity. Copyright

Simple Enols. 4. Generation of Some New Simple Enols in Solution and the Kinetics and Mechanism of Their Ketonization

Capon, Brian,Siddhanta, Arup K.,Zucco, Cesar

, p. 3580 - 3584 (1985)

The simple enols -2-hydroxypropene, -3-chloro-2-hydroxypropene, 2,2-dichlorovinyl alcohol, and hydroxypropadiene have been generated from reactive precursors in solution and characterized by NMR spectroscopy.The kinetics of ketonization of 3-chloro-2-hydroxypropene, hydroxypropadiene, and of the previously described (Z)-prop-1-en-1-ol and 2-methylprop-1-en-1-ol were studied by UV spectrophotometry at 15 deg C.It was found that k0 varied with pH according to the equation k0 = kH2O + (kH+10-pH) + (kHO-KW)/10-pH and values of kH2O, kH+, and kHO- were evaluated for these four enols.Solvent isotope effects, kH+/kD+, were determined and the acid-catalyzed ketonization of 3-chloro-2-hydroxypropene and 2-methylprop-1-en-1-ol were studied in water-Me2SO4 mixtures.The kinetics of the acid-catalyzed hydrolyses of the methyl enol ethers that correspond to these enols were also investigated.It is concluded that the kinetic results were best explained by concerted mechanism for the hydronium ion catalyzed and spontaneous ketonization and by a stepwise mechanism for the hydroxide ion catalyzed ketonization.

Single Turnover Epoxidation of Propylene by α-Complexes (FeIII-O?)α on the Surface of FeZSM-5 Zeolite

Panov, Gennady I.,Starokon, Eugeny V.,Parfenov, Mikhail V.,Pirutko, Larisa V.

, p. 3875 - 3879 (2016)

Single turnover epoxidation of propylene by α-complexes (FeIII-O?)α on the surface of FeZSM-5 zeolite was studied in the temperature range from +25 °C to -60 °C. After extraction, the reaction products were identified by gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR). The reaction C3H6 + (FeIII-O?)α was shown to proceed in a similar way as the oxidation of propylene by the enzyme methane mono-oxygenase sMMO, i.e., via the addition of active oxygen over C=C bonds to yield propylene oxide, not affecting a weakly bound allylic hydrogen. This result, together with the previous results on the hydroxylation of methane and other hydrocarbons, shows the (FeIII-O?)α to be the unique functional model of compound Q, the key intermediate of sMMO. In another aspect, the results relate to the low selectivity problem of the silver catalyst in propylene epoxidation and raise doubts about the presently accepted mechanism explaining an adverse effect of allylic hydrogen.

Measurement of Rates and Equilibria for Keto-Enol Tautomerism of Aldehydes Using Horseradish Peroxidase Compound I

Bohne, Cornelia,MacDonald, I. David,Dunford, H. Brian

, p. 7867 - 7868 (1986)

-

Promoting effect of Al on tethered ligand-modified Rh/SiO2 catalysts for ethylene hydroformylation

Liu, Jia,Yan, Li,Ding, Yunjie,Jiang, Miao,Dong, Wenda,Song, Xiangen,Liu, Tao,Zhu, Hejun

, p. 127 - 132 (2015)

A Rh/SiO2 catalyst with excellent activity and stability for ethylene hydroformylation was developed by modifying with tethered diphenylphosphinopropyl and doped with an Al promoter. The catalyst was characterized by means of N2 adsorption/desorption isotherms, transmission electron microscope, NH3 temperature programmed desorption, Fourier transform infrared spectroscopy and solid-state nuclear magnetic resonance. Experimental results showed that the existence of the Al promoter inhibited the growth of Rh particles, increased the number of exposed Rh atoms, changed the acidity of the catalyst surface, promoted in situ formation of active species that were similar to their corresponding homogeneous counterparts, and enhanced electron density of the P atom in the phosphine ligand.

Direct formation of propanol from a dilute ethylene feed via reductive-hydroformylation using homogeneous rhodium catalysts at low feed pressures

Rodriguez, Brandon A.,Tenn III, William J.

, p. 161 - 163 (2012)

This work details a system for the direct production of propanol from a dilute ethylene stream by reductive hydroformylation catalyzed by soluble rhodium complexes coordinated to tri-aryl or tri-alkyl phosphines. Typically, in commercial production, normal alcohols are produced from primary olefins via a two step process consisting of hydroformylation of the olefins to aldehydes, followed by subsequent hydrogenation of the aldehydes to the corresponding alcohols. This work describes a method to produce propanol directly from dilute ethylene feeds. In addition, the partial pressures of the syngas used in these experiments are significantly lower (approximately an order of magnitude) than reported for nearly all of the other rhodium catalyzed reductive- hydroformylation systems (0.7-70 atm vs. ~20-700 atm).

Selective oxidation of propylene to propylene oxide or propionaldehyde over au supported on titanosilicates in the presence of H2 and O2

Uphade,Tsubota, Susumu,Hayashi, Toshio,Haruta, Masatake

, p. 1277 - 1278 (1998)

Gas phase selective oxidation of propylene to propylene oxide (PO) or propionaldehyde (PA) in the presence of H2 and O2 has been carried out with a propylene conversion in the range of 0.5-3.7% over gold deposited on titanosilicates

Solvent effects in acid-catalyzed biomass conversion reactions

Mellmer, Max A.,Sener, Canan,Gallo, Jean Marcel R.,Luterbacher, Jeremy S.,Alonso, David Martin,Dumesic, James A.

, p. 11872 - 11875 (2014)

Reaction kinetics were studied to quantify the effects of polar aprotic organic solvents on the acid-catalyzed conversion of xylose into furfural. A solvent of particular importance is g-valerolactone (GVL), which leads to significant increases in reaction rates compared to water in addition to increased product selectivity. GVL has similar effects on the kinetics for the dehydration of 1,2-propanediol to propanal and for the hydrolysis of cellobiose to glucose. Based on results obtained for homogeneous Bronsted acid catalysts that span a range of pKa values, we suggest that an aprotic organic solvent affects the reaction kinetics by changing the stabilization of the acidic proton relative to the protonated transition state. This same behavior is displayed by strong solid Bronsted acid catalysts, such as H-mordenite and H-beta.

Fast Generation and Stabilization of 2-Methylprop-1-en-1-ol with ClO4

Park, Jeonghan,Chin, Chong Shik

, p. 1213 - 1214 (1987)

2-Methylprop-1-en-1-ol is rapidly generated and stabilized during the isomerization of 2-methylprop-2-en-1-ol to 2-methylpropanal with ClO4.

Kinetics and mechanism of oxidation of some aliphatic esters by sodium n-bromo-p-toluenesulfonamide

Rangappa,Mythily,Mahadevappa,Gowda

, p. 97 - 105 (1993)

The kinetics of oxidation of methyl, ethyl, n-propyl, isopropyl, and n-butyl acetates to acetic acid and the corresponding aldehyde by the title oxidant in aqueous HCl medium at 40°C has been studied. The reaction shows first-order with respect to [oxidant] and fractional orders in [H+] and [ester]. An isokinetic relationship was observed with β = 374 K indicating enthalpy as the rate controlling factor. Attempts have been made to arrive at a linear free energy relationship through the Taft treatment. Electron releasing groups in the ester moiety increase the rate with ρ = -9.88. A two-pathway mechanism, consistent with the obs d kinetic data, has been proposed.

Homogeneous Catalysis of the Reppe Reaction with Iron Pentacarbonyl: The Production of Propionaldehyde and 1-Propanol from Ethylene

Massoudi, R.,Kim, J. H.,King, R. B.,King, Allen D.

, p. 7428 - 7433 (1987)

The Reppe hydroformylation of ethylene to produce propionaldehyde and 1-propanol in basic solutions containing Fe(CO)5 as a catalyst has been studied under carefully controlled conditions at temperatures ranging from 110 to 140 deg C.Propionaldehyde is the principal product formed when NaOH is used as the base.The rate of reaction is found to increase with ethylene concentration and is second order with respect to Fe(CO)5.The reaction is inhibited by CO.The increase in reaction rate with temperature corresponds to an activation energy of 31 kcal/mol.Infrared spectra indicate that HFe(CO)4- and Fe(CO)5 are present in the solution phase under reaction conditions.The experimental results are shown to be consistent with a mechanism in which the rate-determining step involves a binuclear iron carbonyl derivative.The substitution of (C2H5)3N for NaOH facilitates the reduction of propionaldehyde to form 1-propanol but results in a slower rate for the overall reaction.

Direct synthesis of isobutyraldehyde from methanol and ethanol on Cu-Mg/Ti-SBA-15 catalysts: The role of Ti

Zhang, Junfeng,Zhang, Meng,Wang, Xiaoxing,Zhang, Qingde,Song, Faen,Tan, Yisheng,Han, Yizhuo

, p. 9639 - 9648 (2017)

Herein, Cu-Mg/Ti-SBA-15 catalysts were prepared through the modification of Cu and Mg to mesoporous Ti-SBA-15 zeolites with different Ti/Si ratios and used for the synthesis of isobutyraldehyde (IBA) from methanol and ethanol. The catalysts were characterized via various techniques including XRF, XRD, TEM, N2 sorption, CO2-TPD, FT-IR, and XPS. With an increase in Ti content, CuO was well dispersed accordingly, and the amounts and strength of the basic sites were reduced. However, an excess introduction of Ti led to the accumulation of single TiO2 crystals, inducing a decrease in the surface area and a deviation from the regular pattern such that the binding energies of Cu 2p, Mg 2p, and Si 2p shifted to lower values. This precisely affected the catalytic behaviors of the prepared catalysts synergistically. The catalyst stability was improved with the increasing Ti content accordingly, and over the catalyst with a Ti/Si ratio = 4/15, the IBA selectivity, after 24 h reaction, could still reach 25%, which was the best durability ever reported for IBA synthesis from methanol and ethanol. The catalytic performance test conducted using a regenerated catalyst and IR measurement of the spent catalyst indicated that carbon deposition on the catalyst surface could be depressed to some extent with the increasing Ti content.

FTIR studies of iron-carbonyl intermediates in allylic alcohol photoisomerization

Chong, Thiam Seong,Tan, Sze Tat,Fan, Wai Yip

, p. 5128 - 5133 (2006)

The 532 or 355 nm laser-induced photoisomerization of allylic alcohols to aldehydes catalyzed by [Fe3(CO)12] or [Fe(CO) 4PPh3] in hexane was investigated. The Fourier transform infrared (FTIR) absorption spectra of iron-carbonyl intermediate species such as [Fe(CO)5], [Fe(CO)4(RC3H4OH)], and more importantly the π-allyl iron-carbonyl hydride species [FeH(CO) 3(R-C3H3OH)] (R = H, Me, Ph) were recorded during the catalytic process using [Fe3(CO)12] as the catalytic precursor. When [Fe(CO)4PPh3] was photolyzed with 355 nm, [FeH(CO)3(R-C3H3OH)] was also generated indicating the common occurrence of the species in these two systems. The π-allyl hydride species is long believed to be a key intermediates and its detection here lends support to the π-allyl mechanism of the photoisomerization of allyl alcohols.

Kinetic and mechanistic studies of some aliphatic amines' oxidation by sodium N-bromo-p-toluenesulfonamide in hydrochloric acid medium

Ananda,Jagadeesha,Puttaswamy,Venkatesha,Vinod,Made Gowda

, p. 776 - 783 (2000)

Oxidations of n-propyl, n-butyl, isobutyl, and isoamyl amines by bromamine-T (BAT) in HCl medium have been kinetically studied at 30°C. The reaction rate shows a first-order dependence on [BAT], a fractional-order dependence on [amine], and an inverse fractional-order dependence on [HCl]. The additions of halide ions and the reduction product of BAT, p-toluenesulfonamide, have no effect on the reaction rate. The variation of ionic strength of the medium has no influence on the reaction. Activation parameters have been evaluated from the Arrhenius and Eyring plots. Mechanisms consistent with the preceding kinetic data have been proposed. The protonation constant of monobromamine-T has been evaluated to be 48 ± 1. A Taft linear free-energy relationship is observed for the reaction with ρ* = -12.6, indicating that the electron-donating groups enhance the reaction rate. An isokinetic relationship is observed with β = 350 K, indicating that enthalpy factors control the reaction rate.

ON HYDROGEN ACTIVATION IN THE HYDROFORMYLATION OF OLEFINS WITH Rh4(CO)12 OR Co2(CO)8 AS CATALYST PRECURSORS

Pino, Piero,Oldani, Felix,Consiglio, Giambattista

, p. 491 - 498 (1983)

In the hydroformylation of ethylene with approximately equimolar H2/D2 mixtures and Rh4(CO)12 or Co2(CO)8 as the catalyst precursor about 50percent of propionaldehyde-d1 was formed.The propionaldehyde-d0/d2 ratio was ca. 3 for rhodium and ca. 2.6 for the cobalt catalyst.On the basis of the results and assuming that there is no rapid M(H)2/M(D)2 scrambling, activation of hydrogen through M(H)2 or M(H)2 (olefin) complexes can be excluded.

A Striking Effect of H2S Treatment of Catalyst on the Improvement of Acetic Acid Selectivity in High Pressure CO Hydrogenation over Rh-Ir-Mn-Li/SiO2

Nakajo, Tetsuo,Arakawa, Hironori,Sano, Ken-ichi,Matsuhira, Shinya

, p. 593 - 596 (1987)

A selective synthesis of acetic acid from syngas was investigated.Acetic acid was produced with nearly 70percent selectivity in carbon efficiency over H2S-modified Rh-Ir-Mn-Li/SiO2 catalyst at the expense of the activity.The role of H2S modification was also studied.

EFFECTS OF VARIOUS PRETREATMENTS OF THE Rh-Y ZEOLITE ON THE CATALYTIC ACTIVITY FOR ETHYLENE HYDROFORMYLATION UNDER ATMOSPHERIC PRESSURE

Takahashi, Nobuo,Hasegawa, Shuichi,Hanada, Norio,Kobayashi, Masayoshi

, p. 945 - 948 (1983)

The active species for ethylene hydroformylation formed in the Y zeolite are extremely stable under the reaction conditions and the steady activity lasts more than one month.The catalytic activity is remarkably affected by the pretreatment of the catalyst; the He-H2 pretreatment at 338-453 K enhances the activity while the He-CO or He-CO-C2H4 pretreatment at 400 K reduces it.

Enhancing the activity, selectivity, and recyclability of Rh/PPh3 system-catalyzed hydroformylation reactions through the development of a PPh3-derived quasi-porous organic cage as a ligand

Wang, Wenlong,Li, Cunyao,Zhang, Heng,Zhang, Jiangwei,Lu, Lanlu,Jiang, Zheng,Cui, Lifeng,Liu, Hongguang,Yan, Li,Ding, Yunjie

, p. 1216 - 1226 (2021/03/06)

In contrast to heterogeneous network frameworks (e.g., covalent organic frameworks and metal-organic frameworks) and porous organic polymers, porous organic cages (POCs) are soluble molecules in common organic solvents that provide significant potential for homogeneous catalysis. Herein, we report a triphenylphosphine-derived quasi-porous organic cage (denoted as POC-DICP) as an efficient organic molecular cage ligand for Rh/PPh3 system-catalyzed homogeneous hydroformylation reactions. POC-DICP not only displays enhanced hydroformylation selectivity (aldehyde selectivity as high as 97% and a linear-to-branch ratio as high as 1.89) but can also be recovered and reused via a simple precipitation method in homogeneous reaction systems. We speculate that the reason for the high activity and good selectivity is the favorable geometry (cone angle = 123.88°) and electronic effect (P site is relatively electron-deficient) of POC-DICP, which were also demonstrated by density functional theory calculations and X-ray absorption fine-structure characterization.

Green, homogeneous oxidation of alcohols by dimeric copper(II) complexes

Maurya, Abhishek,Haldar, Chanchal

, p. 885 - 904 (2020/12/18)

Three pyrazole derivatives, 3,5-dimethyl-1H-pyrazole (DMPz) (I), 3-methyl-5-phenyl-1H-pyrazole (MPPz) (II), and 3,5-diphenyl-1H-pyrazole (DPPz) (III), were prepared via reacting semicarbazide hydrochloride with the acetylacetone, 1-phenylbutane-1,3-dione, and 1,3-diphenylpropane-1,3-dione, respectively. Complexes 1–3 were isolated by reacting CuCl2·2H2O with I–III, respectively, and characterized by CHNS elemental analyses, FT-IR, UV-Vis, 1H and 13C NMR, EPR spectra, and TGA/DTA. Molecular structures of the pyrazole derivatives I–III and copper(II) complexes 2 and 3 were studied through single-crystal XRD analysis to confirm their molecular structures. Overlapping of hyperfine splitting in the EPR spectra of the dimeric copper(II) complexes 1–3 indicates that both copper centers do not possess the same electronic environment in solution. The copper(II) complexes are dimeric in solid state as well as in solution and catalyze the oxidation of various primary and secondary alcohols selectively. Catalysts 1–3 show more than 92% product selectivity toward ketones during the oxidation of secondary alcohols. Surprisingly primary alcohols, which are relatively difficult to oxidize, produce carboxylic acid as a major product (48%–90% selectivity) irrespective of catalytic systems. The selectivity for carboxylic acid rises with decreasing the carbon chain length of the alcohols. An eco-friendly and affordable catalytic system for oxidation of alcohols is developed by the utilization of H2O2, a green oxidant, and water, a clean and greener solvent, which is a notable aspect of the study.

Dual utility of a single diphosphine-ruthenium complex: A precursor for new complexes and, a pre-catalyst for transfer-hydrogenation and Oppenauer oxidation

Mukherjee, Aparajita,Bhattacharya, Samaresh

, p. 15617 - 15631 (2021/05/19)

The diphosphine-ruthenium complex, [Ru(dppbz)(CO)2Cl2] (dppbz = 1,2-bis(diphenylphosphino)benzene), where the two carbonyls are mutually cis and the two chlorides are trans, has been found to serve as an efficient precursor for the synthesis of new complexes. In [Ru(dppbz)(CO)2Cl2] one of the two carbonyls undergoes facile displacement by neutral monodentate ligands (L) to afford complexes of the type [Ru(dppbz)(CO)(L)Cl2] (L = acetonitrile, 4-picoline and dimethyl sulfoxide). Both the carbonyls in [Ru(dppbz)(CO)2Cl2] are displaced on reaction with another equivalent of dppbz to afford [Ru(dppbz)2Cl2]. The two carbonyls and the two chlorides in [Ru(dppbz)(CO)2Cl2] could be displaced together by chelating mono-anionic bidentate ligands, viz. anions derived from 8-hydroxyquinoline (Hq) and 2-picolinic acid (Hpic) via loss of a proton, to afford the mixed-tris complexes [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], respectively. The molecular structures of four selected complexes, viz. [Ru(dppbz)(CO)(dmso)Cl2], [Ru(dppbz)2Cl2], [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], have been determined by X-ray crystallography. In dichloromethane solution, all the complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows redox responses within 0.71 to -1.24 V vs. SCE. [Ru(dppbz)(CO)2Cl2] has been found to serve as an excellent pre-catalyst for catalytic transfer-hydrogenation and Oppenauer oxidation.

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