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106-22-9

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106-22-9 Usage

Description

Citronellol is a kind of natural occurring acyclic monoterpenoid which can be found in citronella oils such as Cymbopogon nardus ((+)-citronellol) and rose oils and Pelargonium geraniums ((-)-citronellol). In addition to be extracted from natural oils, it can also be manufactured by the hydrogenation of geraniol or nerol. It is mainly used in perfumes and insects repellents as well as being used as a mite attractant. It should be noted that it is an excellent mosquito repellent at short distances. Combination with beta-cyclodextrin can make it has an average duration time of 1.5 hour against the mosquitoes. It can also be used for the manufacture of rose oxide. One of its most common applications is for adding floral and citrus notes to perfumes, soaps and cosmetics.

Chemical Properties

Different sources of media describe the Chemical Properties of 106-22-9 differently. You can refer to the following data:
1. colourless liquid with a characteristic, rose-like, smell
2. Citronellol has a characteristic rose-like odor. Because odor plays such an important part in selecting this material, there may be special grades of citronellol that do not meet the Essential Oil Association specification. These limits have been broadened enough to include best qualities of commercial citronellol and chemically pure citronellol. l-Citronellol has a sweet, peach-like flavor; d-citronellol has a bitter taste.

Occurrence

l-Citronellol has been found in the plants of the Rosaceae family; d- and dl-citronellol have been identified in Verbenaceae, Labiatae, Rutaceae, Geraniaceae and others; citronellol has been reported in about 70 essential oils and in the oil of Rosa bourbonia; the Bulgarian rose oil has been reported to contain more than 50% l-citronellol, whereas East African geranium contains more than 80% of the d-isomer; the natural product is always optically active. Reported found in guava fruit, orange, bilberry, blackcurrant, nutmeg, ginger, corn mint oil (Mentha arvensis L. var. piperascens), mustard, pennyroyal oil (Mentha pulegium L.), hop oil, tea, coriander seed, cardamom, beer, rum, and apple juice.

Uses

Different sources of media describe the Uses of 106-22-9 differently. You can refer to the following data:
1. Perfumery, flavoring agent.
2. citronellol is a constituent of plant essential oils. Found abundantly in eucalyptus oil. It is used for masking odor or providing a fragrance component to a cosmetic product.
3. rac-Citronellol is a monoterpene found in the essential oil of various plants with antihypertensive properties. It possesses hypotensive actions due to its vasodilator abilities and is a phytochemical used in perfumes and insect repellents.

Preparation

By reduction of citronellal or geraniol or by fractional distillation of such essential oils as geranium and citronella (Bedoukian, 1967).

Definition

ChEBI: A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.

Aroma threshold values

Detection at 11 ppb to 2.2 ppm; l-form, 40 ppb

Taste threshold values

Taste characteristics at 20 ppm: floral, rose, sweet and green with fruity citrus nuances.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 2260, 1995 DOI: 10.1021/jo00112a056Synthesis, p. 391, 1976Tetrahedron Letters, 30, p. 5677, 1989 DOI: 10.1016/S0040-4039(00)76168-5

General Description

Citronellol is a volatile monoterpenic primary alcohol mainly found in the essential oil of plants such as Pelargonium graveolens, Cymbopogon winterianus and Rosa damascena. It is also one of the glycosidically bound aroma compounds in ginger.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, skin contact, and intramuscular routes. A severe skin irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALCOHOLS.

Synthesis

It is generally accepted to distinguish rhodinol as the product isolated from geranium consisting of a mixture of l-citronellol and geraniol, whereas the name l-citronellol should be used to indicate the corresponding synthetic product with the highest level of purity; dl-citronellol can be prepared by catalytic hydrogenation of geraniol or by oxidation of allo-cyrnene; l-citronellol is prepared from (+) d-pinene via (+) cis-pinene to (+) 2,6-dimethyl-2,7-octadiene and, finally, isolating l-citronellol by hydrolysis of the aluminum-organo compound.

Purification Methods

Purify them bydistillation through a cannon packed (Ni) column and the main cut collected at 84o/14mm and redistilled. Also purify via the benzoate. [IR: Eschenazi J Org Chem 26 3072 1961, Naves Bull Soc Chim Fr 505 1951, Beilstein 1 IV 2188.]

References

https://eic.rsc.org/magnificent-molecules/citronellol/2000020.article https://en.wikipedia.org/wiki/Citronellol

Check Digit Verification of cas no

The CAS Registry Mumber 106-22-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 106-22:
(5*1)+(4*0)+(3*6)+(2*2)+(1*2)=29
29 % 10 = 9
So 106-22-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1

106-22-9 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0370)  β-Citronellol  >92.0%(GC)

  • 106-22-9

  • 25mL

  • 130.00CNY

  • Detail
  • TCI America

  • (C0370)  β-Citronellol  >92.0%(GC)

  • 106-22-9

  • 100mL

  • 320.00CNY

  • Detail
  • TCI America

  • (C0370)  β-Citronellol  >92.0%(GC)

  • 106-22-9

  • 500mL

  • 835.00CNY

  • Detail
  • Alfa Aesar

  • (A19016)  Citronellol, 95%   

  • 106-22-9

  • 100g

  • 209.0CNY

  • Detail
  • Alfa Aesar

  • (A19016)  Citronellol, 95%   

  • 106-22-9

  • 500g

  • 580.0CNY

  • Detail
  • Sigma-Aldrich

  • (51381)  (±)-β-Citronellol  analytical standard

  • 106-22-9

  • 51381-1ML

  • 3,141.45CNY

  • Detail

106-22-9SDS

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 citronellol

1.2 Other means of identification

Product number -
Other names Citronellol

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:106-22-9 SDS

106-22-9Synthetic route

3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran at 20℃; Reduction;100%
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 0.75h;100%
With trimethylamine-N-oxide; sodium formate; C34H44FeN4O4(2+)*2I(1-) In water at 80℃; for 24h; Inert atmosphere; Schlenk technique;99%
Geraniol
106-24-1

Geraniol

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 12h;100%
With hydrogen; polymer-supported rhodium catalyst In dichloromethane under 1551.49 Torr; for 10h; Hydrogenation;96%
With 1,1'-bis(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; Butane-1,4-diol; potassium tert-butylate at 110℃; for 24h; Inert atmosphere;71%
Nerol
106-25-2

Nerol

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 12h;100%
With dichloro(η3:η2:η3-dodeca-2,6,10-triene-1,12-diyl)ruthenium(IV); caesium carbonate; isopropyl alcohol at 82℃; for 23h; Inert atmosphere; chemoselective reaction;95 %Chromat.
1-(benzyloxy)-3,7-dimethyloct-6-ene
96154-40-4

1-(benzyloxy)-3,7-dimethyloct-6-ene

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With hydrogen; benzyl bromide; Pd<*>MCM-48 In methanol under 760.051 Torr; for 0.5h;99%
With aluminium trichloride; N,N-dimethyl-aniline In dichloromethane for 1.5h; Ambient temperature;98%
With naphthalene; lithium In tetrahydrofuran; methanol at -78℃; for 40h;89%
methyl 3,7-dimethyloct-6-enoate
2270-60-2

methyl 3,7-dimethyloct-6-enoate

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With [RuCl2((E)-N-(2-(diphenylphosphino)benzyl)-1-(6-((diphenylphosphino)methyl)pyridin-2-yl)methanimine)]; hydrogen; sodium ethanolate at 80℃; under 37503.8 Torr; for 5h; Autoclave;98%
With lithium aluminium tetrahydride Yield given;
1-(3,7-Dimethyl-oct-6-enyloxymethoxy)-4-methoxy-benzene

1-(3,7-Dimethyl-oct-6-enyloxymethoxy)-4-methoxy-benzene

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 0.5h; Product distribution;98%
2-(3,7-dimethyloct-6-enyloxy)-tetrahydro-2H-pyran
90243-41-7

2-(3,7-dimethyloct-6-enyloxy)-tetrahydro-2H-pyran

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With SA-3 silica-alumina gel In methanol at 120℃; for 2.16667h;98%
With SA-3 silica-alumina gel In methanol at 120℃; for 2.16667h; Product distribution; other ethers, var. silica-alumina gels, temp. and time;98%
With copper dichloride In methanol at 20℃; Hydrolysis;90%
With CuCl2*2H2O In methanol at 20℃; for 1.25h;90%
With boron trifluoride diethyl etherate; sodium cyanoborohydride In tetrahydrofuran for 3h; Ambient temperature;80%
Acetaldehyde ethyl 3,7-dimethyl-6-octenyl acetal

Acetaldehyde ethyl 3,7-dimethyl-6-octenyl acetal

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With SA-3 silica-alumina gel In methanol at 120℃; for 1.33333h;98%
8-(1-Methoxy-ethoxy)-2,6-dimethyl-oct-2-ene

8-(1-Methoxy-ethoxy)-2,6-dimethyl-oct-2-ene

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With dibromotriphenylphosphorane In dichloromethane at -50℃; for 2h;97%
(3,7-dimethyloct-6-enyloxy)trimethylsilane
18419-09-5

(3,7-dimethyloct-6-enyloxy)trimethylsilane

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With SA-3 silica-alumina gel In methanol for 1.16667h; Ambient temperature;97%
With 18-crown-6 ether In ethanol; water at 45℃; for 3h; Green chemistry;91%
3,7-dimethyl-1-(1-methyl-1-methoxyethoxy)-6-octene

3,7-dimethyl-1-(1-methyl-1-methoxyethoxy)-6-octene

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With SA-2 silica-alumina gel In methanol for 3.16667h; Ambient temperature;97%
cis-3,7-dimethyl-2,6-octadienal
106-26-3

cis-3,7-dimethyl-2,6-octadienal

A

Citronellol
106-22-9

Citronellol

B

3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

Conditions
ConditionsYield
With acetylacetonato(1,5-cyclooctadiene)rhodium(I); hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 25℃; under 750.075 Torr; for 0.5h; Catalytic behavior; Temperature; Pressure; Autoclave; chemoselective reaction;A 3%
B 97%
With acetylacetonatodicarbonylrhodium(l); hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In neat (no solvent) at 60℃; under 30003 Torr; for 10h; Temperature; Pressure; Autoclave;A 88 %Spectr.
B 12 %Spectr.
8-(2-methoxy-ethoxymethoxy)-2,6-dimethyl-oct-2-ene

8-(2-methoxy-ethoxymethoxy)-2,6-dimethyl-oct-2-ene

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With cerium(III) chloride In acetonitrile for 1h; Heating;96%
(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With LaNi5 hydride In tetrahydrofuran; methanol for 12h; Ambient temperature;95%
With LaNi5 hydride In tetrahydrofuran; methanol 1) 0 deg C, 6 h, 2) r.t., 12 h;95%
With hydrido(triphenylphosphine)copper(I) hexamer In tetrahydrofuran for 24h; Ambient temperature;90%
(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

A

Citronellol
106-22-9

Citronellol

B

3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

Conditions
ConditionsYield
With hydrogen; Ni0.88Cr0.12 In cyclohexane at 79.9℃; under 7575.6 Torr; Product distribution; other catalysts, hydrogenation rates, selectivity of catalysts;A n/a
B 92%
With hydrogen; Ni-Gr2 In methanol at 45℃; under 22800 Torr; for 18h;A 68%
B 26%
With hydrogen; sodium carbonate; chromium(III) oxide; nickel In water; isopropyl alcohol at 120℃; under 30400 Torr; Product distribution; other temperature, other solvent, other pressure, other catalysts;A 0.6 % Chromat.
B 97.5 % Chromat.
tert-butyl((3,7-dimethyloct-6-en-1-yl)oxy)dimethylsilane
87921-26-4

tert-butyl((3,7-dimethyloct-6-en-1-yl)oxy)dimethylsilane

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With 2,5-bis(perfluorobutyl)-1,4-benzoquinone In water; acetonitrile at 20℃; for 6h;92%
With oxone In methanol at 20℃; for 15h;80%
With bismuth(III) chloride; sodium iodide In acetonitrile at 20℃; for 1.5h;76%
3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

aniline
62-53-3

aniline

A

Citronellol
106-22-9

Citronellol

B

N-(3,7-dimethyloct-6-en-1-yl)aniline
31043-21-7

N-(3,7-dimethyloct-6-en-1-yl)aniline

Conditions
ConditionsYield
Stage #1: 3,7-dimethyl-oct-6-enal; aniline at 25℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate; boric acid at 25℃; for 0.333333h;
A n/a
B 92%
3,7-dimethyl-1-[tris(trimethylsilyl)silyl]-6-octen-1-ol

3,7-dimethyl-1-[tris(trimethylsilyl)silyl]-6-octen-1-ol

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
In methanol; dichloromethane desilylation; Photolysis;91%
C23H32OSi

C23H32OSi

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With 18-crown-6 ether In ethanol; water at 45℃; for 2.5h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry;91%
8-iodo-3,7-dimethyloct-6-en-1-ol acetate

8-iodo-3,7-dimethyloct-6-en-1-ol acetate

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at -20℃;90%
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With Ba(BH2S3)2 In tetrahydrofuran at 20℃; for 2.5h;90%
With hydrogen In isopropyl alcohol at 70℃; under 56255.6 Torr; for 2h; Reagent/catalyst; Autoclave; Glovebox;
(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

A

Citronellol
106-22-9

Citronellol

B

tetrahydrogeraniol
106-21-8, 59204-02-3

tetrahydrogeraniol

menthol
15356-70-4

menthol

Conditions
ConditionsYield
With hydrogen In tert-butyl alcohol at 80℃; under 1500.15 - 15001.5 Torr; for 8h; Autoclave; diastereoselective reaction;A n/a
B n/a
C 89%
(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

A

Citronellol
106-22-9

Citronellol

B

geraniol
624-15-7

geraniol

Conditions
ConditionsYield
With hydrogen; silver In tetrahydrofuran at 150℃; under 11251.1 Torr; for 72h;A 10%
B 88%
With sodium cyanoborohydride at 20℃; for 0.05h;A 46%
B 54%
With (triphenylphosphine)copper(I) hydride hexamer; hydrogen; Dimethyl(phenyl)phosphine In tert-butyl alcohol; benzene at 20℃; under 25857.4 Torr; for 15h; Hydrogenation; Title compound not separated from byproducts;
3,7-dimethyl-3,6-octadienal
1754-00-3, 55722-59-3

3,7-dimethyl-3,6-octadienal

A

Citronellol
106-22-9

Citronellol

B

geraniol
624-15-7

geraniol

Conditions
ConditionsYield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; sodium formate In water at 80℃; for 0.5h; Schlenk technique; chemoselective reaction;A 88%
B n/a
allyl 3,7-dimethyloct-6-en-1-yl ether

allyl 3,7-dimethyloct-6-en-1-yl ether

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With samarium diiodide; water; isopropylamine In tetrahydrofuran at 20℃; for 0.0833333h;87%
With naphthalene; lithium In tetrahydrofuran; methanol at -78℃; for 40h;86%
Conditions
ConditionsYield
With hydrogen In tert-butyl alcohol at 80℃; under 7500.75 Torr; for 8h; Autoclave; diastereoselective reaction;A n/a
B n/a
C 87%
D n/a
(+/-)-citronellyl tosylate
41144-01-8

(+/-)-citronellyl tosylate

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 10h; Electrolysis; Green chemistry;87%
3,7-dimethyl-1-acetoxy-6-p-toluenesulfonyloxy octane
110109-86-9

3,7-dimethyl-1-acetoxy-6-p-toluenesulfonyloxy octane

A

Citronellol
106-22-9

Citronellol

B

tetrahydrogeraniol
106-21-8, 59204-02-3

tetrahydrogeraniol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran 1.) -10 deg C 2.) RT;A 6%
B 82%
3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

A

Citronellol
106-22-9

Citronellol

B

(3,7-dimethyloctyl)amine
13887-74-6, 90544-01-7

(3,7-dimethyloctyl)amine

C

3,7-dimethyl-6-octenylamine
53339-59-6

3,7-dimethyl-6-octenylamine

D

3,3',7,7'-tetramethyldi-6-octenylamine
24381-83-7

3,3',7,7'-tetramethyldi-6-octenylamine

E

(E)-N-(3,7-dimethyloct-6-en-1-ylidene)-3,7-dimethyloct-6-en-1-amine

(E)-N-(3,7-dimethyloct-6-en-1-ylidene)-3,7-dimethyloct-6-en-1-amine

F

3,7-dimethyloct-6-en-1-imine

3,7-dimethyloct-6-en-1-imine

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; ammonium hydroxide; 1-methyl-3-decylimidazolium bromide In toluene at 130℃; under 45004.5 Torr; for 6h; Reagent/catalyst; Autoclave;A 8%
B 1%
C 81%
D n/a
E n/a
F 8%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; ammonium hydroxide; 1-octyl-3-methyl-imidazolium bromide In toluene at 130℃; under 45004.5 Torr; for 6h; Autoclave;A 20%
B 2%
C 41%
D n/a
E n/a
F 21%
allyl citronellyl carbonate

allyl citronellyl carbonate

Citronellol
106-22-9

Citronellol

Conditions
ConditionsYield
With palladium diacetate; sodium azide; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 25℃; for 1h;80%
Citronellol
106-22-9

Citronellol

citronellylbromide
4895-14-1

citronellylbromide

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 2h;100%
With 1H-imidazole; iodine In dichloromethane at 20℃; for 0.75h;93%
With pyridine; bromine; triphenylphosphine In tetrachloromethane; N,N-dimethyl-formamide at 45℃;89%
Citronellol
106-22-9

Citronellol

benzyl bromide
100-39-0

benzyl bromide

1-(benzyloxy)-3,7-dimethyloct-6-ene
96154-40-4

1-(benzyloxy)-3,7-dimethyloct-6-ene

Conditions
ConditionsYield
Stage #1: Citronellol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: benzyl bromide With sodium iodide In tetrahydrofuran for 5h; Heating;
100%
Stage #1: Citronellol With sodium hydride In tetrahydrofuran; hexane for 2h; Heating;
Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; hexane for 18h; Heating; Further stages.;
58%
With sodium hydride 1.) dimethoxyethane, room temperature, 2 h, 2.) room temperature, 40 h; Yield given. Multistep reaction;
Citronellol
106-22-9

Citronellol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(+/-)-citronellyl tosylate
41144-01-8

(+/-)-citronellyl tosylate

Conditions
ConditionsYield
With pyridine at 0 - 5℃; for 1h;100%
With potassium hydroxide; potassium carbonate for 0.05h;93%
With pyridine In chloroform for 0.5h; sonication;92%
Citronellol
106-22-9

Citronellol

acetic anhydride
108-24-7

acetic anhydride

citronellyl-acetate
150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;100%
With C12H8N2*2CH4O3S at 60℃; for 3h;99%
With iodine at 25℃; for 0.0166667h;98%
Citronellol
106-22-9

Citronellol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl((3,7-dimethyloct-6-en-1-yl)oxy)dimethylsilane
87921-26-4

tert-butyl((3,7-dimethyloct-6-en-1-yl)oxy)dimethylsilane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;100%
With dmap; triethylamine96%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 16h;90%
Citronellol
106-22-9

Citronellol

dec-9-enoic acid
14436-32-9

dec-9-enoic acid

dec-9-enoate 3,7-dimethyl-oct-6-en-1-yl

dec-9-enoate 3,7-dimethyl-oct-6-en-1-yl

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 22h; Inert atmosphere;88%
Citronellol
106-22-9

Citronellol

butyric acid
107-92-6

butyric acid

3,7-dimethyl-6-octenyl butyrate
141-16-2

3,7-dimethyl-6-octenyl butyrate

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.9%
In n-heptane at 40℃; for 24h; lipozyme IM 20 (immobilized Mucor miehi lipase);94.66%
In water at 30℃; for 18h; lipase from Aspergillus niger; Yield given;
Citronellol
106-22-9

Citronellol

propionic acid
802294-64-0

propionic acid

3,7-dimethyl-6-octen-1-ol propanoate
141-14-0

3,7-dimethyl-6-octen-1-ol propanoate

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.9%
In water at 30℃; for 18h; lipase from Aspergillus niger; Yield given;
Citronellol
106-22-9

Citronellol

valeric acid
109-52-4

valeric acid

β-citronellyl valerate

β-citronellyl valerate

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.9%
In water at 30℃; for 18h; lipase from Aspergillus niger; Yield given;
Citronellol
106-22-9

Citronellol

acetic acid
64-19-7

acetic acid

citronellyl-acetate
150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;99.9%
With cetyltrimethylammonium chloride; potassium hexacyanoferrate(III) at 80℃; for 1h;90%
With molecular sieve at 120℃; for 8h;
Citronellol
106-22-9

Citronellol

acryloyl chloride
814-68-6

acryloyl chloride

3,7-dimethyloct-6-en-1-yl acrylate
45160-93-8

3,7-dimethyloct-6-en-1-yl acrylate

Conditions
ConditionsYield
With triethylamine at 20℃;99.5%
With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;64%
Citronellol
106-22-9

Citronellol

tetrahydrogeraniol
106-21-8, 59204-02-3

tetrahydrogeraniol

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In ethyl acetate99%
With hydrogen; palladium on activated charcoal In ethyl acetate at 80℃; under 2585.81 Torr; for 0.0833333h; microwave irradiation;99%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 50h;93%
Citronellol
106-22-9

Citronellol

3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

Conditions
ConditionsYield
With pyridine chromium peroxide In dichloromethane for 1.25h; Product distribution; Ambient temperature; effect of various chromium(VI) based oxidants;99%
With pyridine chromium peroxide In dichloromethane for 1.25h; Ambient temperature;99%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 3-[4'-(diacetoxyiodo)phenoxy]-1-propyl-N,N,N-trimethylammonium 4-methylbenzenesulfonate In dichloromethane at 20℃; for 2h;99%
Citronellol
106-22-9

Citronellol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(±)-3,7-dimethyloct-6-en-1-yl methanesulfonate
42602-37-9

(±)-3,7-dimethyloct-6-en-1-yl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;99%
With triethylamine In dichloromethane at 0 - 20℃; for 24.3h;97%
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;94%
Citronellol
106-22-9

Citronellol

6,7-epoxycitronellol
1564-98-3

6,7-epoxycitronellol

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane Epoxidation;98%
With oxygen; cobalt(II) acetate; isobutyraldehyde In dichloromethane at 20℃; for 5h;98%
With (NMe4)(Co-ortho-phenylenebis(N'-methyloxamidate)*2H2O*CH3CN; oxygen; pivalaldehyde In fluorobenzene for 2.5h; Ambient temperature;95%
Citronellol
106-22-9

Citronellol

acetyl chloride
75-36-5

acetyl chloride

citronellyl-acetate
150-84-5

citronellyl-acetate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In toluene for 1h;98%
Citronellol
106-22-9

Citronellol

1,2-dibromomethane
74-95-3

1,2-dibromomethane

5-(2,2-dimethylcyclopropyl)-3-methylpentan-1-ol
321858-86-0

5-(2,2-dimethylcyclopropyl)-3-methylpentan-1-ol

Conditions
ConditionsYield
Stage #1: Citronellol; 1,2-dibromomethane With triisobutylaluminum at 10 - 20℃; for 0.25h;
Stage #2: With iron(III) chloride; triisobutylaluminum at 25℃; for 3h; regioselective reaction;
98%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Citronellol
106-22-9

Citronellol

(3,7-dimethyloct-6-enyloxy)trimethylsilane
18419-09-5

(3,7-dimethyloct-6-enyloxy)trimethylsilane

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane at 25℃; Inert atmosphere;98%
Citronellol
106-22-9

Citronellol

Tosyl isocyanate
4083-64-1

Tosyl isocyanate

C18H27NO4S

C18H27NO4S

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Inert atmosphere;98%

106-22-9Relevant articles and documents

Electrochemical hydrogenation of citral 1. The role of the copper cathode in the electroreduction of citral

Korotyaeva, L. M.,Rubinskaya, T. Ya.,Gultyai, V. P.

, p. 1830 - 1834 (1993)

Alcohols (citronellol and isomeric nerol and geraniol) are the main products of the electroreduction of citral at the copper cathode in the presence in the AcOH in a water-DMF medium.It has been suggested that under the conditions of the electrolysis at the hydrogen reduction potential (E = -1.2 V) electroreduction of citral occurs according to the electrochemical hydrogenation mechanism.The total yield of the alcohols and the selectivity of the process depend on the preliminary treatment of the cathode.The electroreduction of citral at a mechanically cleaned cathode gives alcohols in 54percent total yield, and unsaturated alcohols are the prevailing products.Preliminary annealing of the cathode results in an increase in the total yield of alcohols in the electrolysis to 86percent and in the predominant formation of citronellol. - Key words: copper cathode, citral, citronellol, electrochemical hydrogenation, electroreduction, recrystallization.

Chemoselective Hydrogenation of Aldehydes under Mild, Base-Free Conditions: Manganese Outperforms Rhenium

Glatz, Mathias,St?ger, Berthold,Himmelbauer, Daniel,Veiros, Luis F.,Kirchner, Karl

, p. 4009 - 4016 (2018)

Several hydride Mn(I) and Re(I) PNP pincer complexes were applied as catalysts for the homogeneous chemoselective hydrogenation of aldehydes. Among these, [Mn(PNP-iPr)(CO)2(H)] was found to be one of the most efficient base metal catalysts for this process and represents a rare example which permits the selective hydrogenation of aldehydes in the presence of ketones and other reducible functionalities, such as C=C double bonds, esters, or nitriles. The reaction proceeds at room temperature under base-free conditions with catalyst loadings between 0.1 and 0.05 mol% and a hydrogen pressure of 50 bar (reaching TONs of up to 2000). A mechanism which involves an outer-sphere hydride transfer and reversible PNP ligand deprotonation/protonation is proposed. Analogous isoelectronic and isostructural Re(I) complexes were only poorly active.

Hydrogenation of alkenes with rhodium nanoparticles supported on SBA-15

Bhorali, Nayanmoni,Ganguli, Jatindra Nath

, p. 276 - 281 (2013)

Rhodium nanoparticles were prepared by chemical reduction of RhCl 3·3H2O in presence of polyvinyl pyrrolidone and then immobilized on SBA-15 by impregnation. The catalyst was used for hydrogenation of unsaturated hydrocarbons at room temperature. The progress of the reaction was monitored by GC-MS and 100 % conversion was achieved in all cases.

Reduction of carbonyl compounds by using polymethylhydrosiloxane: Reactivity and selectivity

Kobayashi, Yuichi,Takahisa, Eisuke,Nakano, Miwa,Watatani, Kengo

, p. 1627 - 1634 (1997)

Reduction of aldehydes and ketones with PMHS [Me3SiO-(SiMe(H)O)(n)-SiMe3] proceeded smoothly in the presence of Bu4NF at -70°C or 0°C within 60 min in THF. High stereo- and chemoselectivities as well as functional group tolerance of this system are also presented.

Hydrogenation of aldehydes and ketones to corresponding alcohols with methylamine borane in neat water

Duan, Yifan,Bai, Ruijiao,Tian, Jun,Chen, Ligong,Yan, Xilong

, p. 2555 - 2564 (2014)

GRAPHICAL ABSTRACT Chemoselective hydrogenation of various aldehydes and ketones with methylamine borane (MeAB) in neat water was investigated. MeAB is suitable for green organic reactions, for MeAB is a nontoxic, environmentally benign, and easily handled reagent. Aldehydes were selectively and rapidly hydrogenated in excellent yields (86-97%) for 30 min, but hydrogenation of aromatic ketones needed over 20 h at room temperature because of their poor water solubility and steric hindrance. Thus we investigated polyethylene glycol (PEG400) and acidic cation-exchange D072 resin as catalysts to accelerate the hydrogenation reaction of aromatic ketones and achieved excellent yields within several hours. PEG 400 and D072 resin are both suitable for green organic reactions. The D072 resin was reused up to four times without any significance loss in activity.

Neilan,J.P. et al.

, p. 3455 - 3460 (1976)

Liquid-phase citral hydrogenation over SiO2-supported Group VIII metals

Singh, Utpal K.,Vannice, M. Albert

, p. 73 - 84 (2001)

Citral hydrogenation was studied over SiO2-supported Group VIII metals at 300 K and 1 atm in the absence of all transport limitations as verified by the Madon-Boudart test and the Weisz-Prater criterion. The initial turnover frequency (TOF) for

Transfer of Hydrogen from Alcohols. Catalysis by Compounds of Tin

Wuest, James D.,Zacharie, Boulos

, p. 166 - 168 (1984)

-

Hydrogenation of citral using monometallic Pt and bimetallic Pt-Ru catalysts on a mesoporous support in supercritical carbon dioxide medium

Chatterjee,Zhao,Ikushima

, p. 459 - 466 (2004)

Supercritical carbon dioxide was shown to be a suitable reaction medium for the highly efficient hydrogenation of citral using monometallic Pt and bimetallic Pt-Ru supported on a mesoporous material, MCM-48, as catalyst. A remarkable change in the product distribution was observed after the addition of Ru to the monometallic Pt catalyst in supercritical carbon dioxide. The monometallic Pt catalyst was found to be highly selective to the unsaturated alcohol (geraniol + nerol) at a temperature of 323 K within 2 h whereas the bimetallic catalyst becomes selective to the partially saturated aldehyde (citronellal) under the same reaction conditions. Phase behavior plays an important role in the product distribution. Highest conversion and high selectivity to citronellal were achieved in the homogeneous phase for the Pt-Ru catalyst while on the other hand the unsaturated alcohol (geraniol + nerol) was produced in the heterogeneous phase for the monometallic Pt catalyst. An XPS study offers strong evidence of the electronic modification of Pt after the addition of Ru in the bimetallic catalyst. The change in product distribution on the Pt-Ru bimetallic catalyst may be explained by the appreciable interaction between the medium and the metal particles promoted by the presence of metallic Ru.

Biomass- And calcium carbide-based recyclable polymers

Metlyaeva, Svetlana A.,Rodygin, Konstantin S.,Lotsman, Kristina A.,Samoylenko, Dmitriy E.,Ananikov, Valentine P.

, p. 2487 - 2495 (2021)

Biomass is a renewable source of valuable feedstock for the chemical industry of the future. A promising approach to the utilization of valuable components of biomass is the synthesis of monomers and polymers, if the overall technology is designed for a clean cycle without pollution of the environment with newly created polymers. In this work, we have developed a methodology for the recycling of polymers based on biomass and calcium carbide. First, we modified a series of biomass-derived terpene alcohols with calcium carbide followed by polymerization of the isolated vinyl ethers. Then, to study the recycling potential, the obtained polymers were subjected to pyrolysis at moderate temperatures (200-450 °C). The pyrolysis products were analyzed using TGA-MS, GC-MS, and NMR, and it was found that the polymers can be transformed quite easily. The products of the pyrolysis consisted of the starting terpenols, as well as the corresponding non-toxic ketones or aldehydes: up to 87% of the starting alcohol or up to 100% of the total sum of alcohol + aldehyde or alcohol + ketone (GC-yields). Then, the reaction mixture was hydrogenated and resulted in the formation of starting alcohol only. According to the studied pathway of polymers re-building, a terpene fragment attached to the main polyethylene chain through an oxygen atom promotes the transformation of the obtained polymers. Thus, the products of pyrolysis are environmentally friendly and can be reused in the further synthesis of monomers. The developed system has shown a unique assembling/disassembling ability and advances the concept of reusable bio-derived high value-added materials.

Chemoselective Pt-catalysts supported on carbon-TiO2 composites for the direct hydrogenation of citral to unsaturated alcohols

Bailón-García, Esther,Carrasco-Marín, Francisco,Pérez-Cadenas, Agustín F.,Maldonado-Hódar, Francisco J.

, p. 701 - 711 (2016)

A series of carbon xerogels-TiO2 composites with different TiO2 contents were prepared, exhaustively characterized and used as a Pt-support to develop selective hydrogenation catalysts. The carbon phase in the composite hinders the TiO2 crystal growth and the transformation to rutile during thermal treatments. Textural, chemical and catalytic properties are determined by the TiO2 content, with an optimum around 40 wt.% of TiO2 content. The mesoporosity of the supports, the Pt-dispersion and Pt-support interactions are favoured in this sense. During the H2-pretreatment, the Pt and TiO2 phases were simultaneously reduced and the formation of oxygen vacancies leads to the mobility of Pt-species inside the TiO2 structure, avoiding sintering in surface and strongly improving both catalytic activity and selectivity. The catalytic performance was discussed on the basis of the sample characteristics. Unsaturated alcohols were obtained as main reaction products in all cases, being the only product in the case of the optimized catalyst.

Transfer hydrogenation of carbonyl compounds catalyzed by ruthenium nanoparticles stabilized on nanocrystalline magnesium oxide by ionic liquids

Lakshmi Kantam,Sudarshan Reddy,Pal, Ujjwal,Sreedhar,Bhargava

, p. 2231 - 2235 (2008)

Transfer hydrogenation of various carbonyl compounds was achieved in excellent yields by ruthenium nanoparticles stabilized on the nanocrystalline magnesium oxide by the incorporation of choline hydroxide, a basic ionic liquid. The procedure is simple, efficient and the catalyst can be recycled five times.

Electrochemical hydrogenation of citral 4. * Role of the acid component in electrochemical hydrogenation

Korotayeva,Rubinskaya,Gultyai

, p. 459 - 462 (1997)

The effect of the nature and concentration of the acid component on the yield and ratio of the products of electrocatalytic hydrogenation of citral was studied. The use of weak organic acids (e.g., AcOH) in amounts that are stoichiometric for hydrogenation of conjugated double bonds was shown to be advantageous.

Selective Hydrogenation of Citral on Pt-Containing Catalysts at Room Temperature and Atmospheric Pressure

Vikanova,Redina

, p. 2566 - 2569 (2019)

Abstract: It is shown that the 1% Pt/CeO2–ZrO2 (1% Pt/CZ) catalytic system allows selective hydrogenation of citral with a 94% conversion and a selectivity towards unsaturated alcohols of 59% at room temperature and atmospheric pressure. The effect of addition of alkali to the reaction mixture on the yield of the target products is studied, and the optimum conditions of the reaction are determined.

Electrochemical hydrogenation of citral 2. The effect of the components of the medium on the process of electrochemical reduction at a copper cathode

Rubinskaya, T. Ya.,Korotayeva, L. M.,Gul'tyai, V. P.

, p. 1835 - 1838 (1993)

The factors (concentration of citral, composition of the solvent, AcOH : citral ratio) affecting electrochemical hydrogenation of citral at an annealed copper cathode have been determined.The highest total yield (94percent) of the alcohols (nerol, geraniol, citranellol) with a considerable predominance of the latter is achieved at 40percent DMF in water, citral concentration 0.02 M, and AcOH : citral ratio = 10 : 1.The transition to purely organic or purely aqueous media leads to a decrease in both the total yield of the alcohols and the selectivity of the process. - Key words: copper cathode, citral, citronellol, electrochemical hydrogenation.

Highly Efficient and Selective Hydrogenation of Aldehydes: A Well-Defined Fe(II) Catalyst Exhibits Noble-Metal Activity

Gorgas, Nikolaus,St?ger, Berthold,Veiros, Luis F.,Kirchner, Karl

, p. 2664 - 2672 (2016)

The synthesis and application of [Fe(PNPMe-iPr)(CO)(H)(Br)] and [Fe(PNPMe-iPr)(H)2(CO)] as catalysts for the homogeneous hydrogenation of aldehydes is described. These systems were found to be among the most efficient catalysts for this process reported to date and constitute rare examples of a catalytic process which allows selective reduction of aldehydes in the presence of ketones and other reducible functionalities. In some cases, TONs and TOFs of up to 80000 and 20000 h-1, respectively, were reached. On the basis of stoichiometric experiments and computational studies, a mechanism which proceeds via a trans-dihydride intermediate is proposed. The structure of the hydride complexes was also confirmed by X-ray crystallography.

An efficient reduction system - NiCl2·6H2O-Zn/DMF-H2O for conversion of aldehydes to alcohols

Baruah, Robindra N.

, p. 5417 - 5418 (1992)

Aldehydes were efficiently converted to the corresponding alcohols at room temperature, with NiCl2·6H2O-Zn/DMF-H2O system.

Tuning selectivity in terpene chemistry: Selective hydrogenation versus cascade reactions over copper catalysts

Zaccheria,Ravasio,Fusi,Rodondi,Psaro

, p. 1267 - 1272 (2005)

The selectivity of Cu/Al2O3 under very mild catalytic hydrogenation conditions can be tuned only by switching the solvent. Geraniol can be converted in a one-pot one-step process into a mixture of citronellol and menthol in hydrocarbon solvents or reduced to citronellol with 98% selectivity in 2-propanol without any additive. Both reactions can be applied to essential oils or synthetic mixtures containing geraniol, citronellal and nerol.

Magnetic nickel ferrite nanoparticles as highly durable catalysts for catalytic transfer hydrogenation of bio-based aldehydes

He, Jian,Yang, Song,Riisager, Anders

, p. 790 - 797 (2018)

Magnetic nickel ferrite (NiFe2O4) nanoparticles were exploited as stable and easily separable heterogeneous catalysts for catalytic transfer hydrogenation (CTH) of furfural to furfuryl alcohol with 2-propanol as both the hydrogen source and the solvent providing 94% product yield at 180 °C after 6 h of reaction. The magnetic properties of the catalysts provided facile recovery using an external magnet after reaction allowing it to be reused in five reaction cycles without loss of catalytic performance. Importantly, the NiFe2O4 nanoparticles were also applicable to CTH of other alkenyl/allyl/aromatic aldehydes affording over 94% selectivity towards the targeted alcohol products, thus being attractive as highly universal catalysts for CTH of aldehydes.

Direct synthesis of hybrid layered double hydroxide-carbon composites supported Pd nanocatalysts efficient in selective hydrogenation of citral

Han, Ruirui,Nan, Chunshi,Yang, Lan,Fan, Guoli,Li, Feng

, p. 33199 - 33207 (2015)

This present study reports a facile one-pot strategy for the direct synthesis of hybrid layered double hydroxide (LDH)-carbon composites supported palladium nanocatalysts by the in situ reduction of PdCl42--intercalated MgAl-LDH combined with amorphous carbon under mild hydrothermal conditions. The results demonstrated that most of the Pd(II) species intercalated in the interlameller space of MgAl-LDH could be reduced in situ to metallic Pd0 species, and simultaneously, the hybrid structure of the LDH-C composites facilitated the formation of uniform Pd nanoparticles with small diameter, as well as the strong metal-support interactions. Furthermore, with the decreasing proportion of the LDH component in LDH-C composites, the average diameter of Pd nanoparticles decreased progressively and the metal-support interactions were weakened. The as-formed supported Pd nanocatalyst with Pd loading of 5.5 wt% was found to show a superior catalytic activity in the liquid-phase selective hydrogenation of citral than other supported Pd nanocatalysts, while the one with the Pd loading of 2.7 wt% yielded a much higher yield of citronellal (~80.0%) at 100% conversion. The catalytic performance of Pd nanocatalysts was proposed to be mainly related to both the metal-support interactions and the compositions of hybrid LDH-C composite supports.

Highly efficient Meerwein-Ponndorf-Verley reductions over a robust zirconium-organoboronic acid hybrid

Song, Jinliang,Hua, Manli,Huang, Xin,Visa, Aurelia,Wu, Tianbin,Fan, Honglei,Hou, Minqiang,Zhang, Zhaofu,Han, Buxing

, p. 1259 - 1265 (2021)

The Meerwein-Ponndorf-Verley (MPV) reaction is an attractive approach to selectively reduce carbonyl groups, and the design of advanced catalysts is the key for these kinds of interesting reactions. Herein, we fabricated a novel zirconium organoborate using 1,4-benzenediboronic acid (BDB) as the precursor for MPV reduction. The prepared Zr-BDB had excellent catalytic performance for the MPV reduction of various biomass-derived carbonyl compounds (i.e., levulinate esters, aldehydes and ketones). More importantly, the number of borate groups on the ligands significantly affected the catalytic activity of the Zr-organic ligand hybrids, owing to the activation role of borate groups on hydroxyl groups in the hydrogen source. Detailed investigations revealed that the excellent performance of Zr-BDB was contributed by the synergetic effect of Zr4+and borate. Notably, this is the first work to enhance the activity of Zr-based catalysts in MPV reactions using borate groups.

Triphenylphosphine Dibromide: Effective and Selective Reagent for the Cleavage of Acetals

Wagner, Alain,Heitz, Marie-Paule,Mioskowski, Charles

, p. 1619 - 1620 (1989)

Triphenylphosphine dibromide (PPh3Br2) is a mild and highly effective reagent for hydrolysis of various acetals in dichloromethane at low temperature.

-

Rennie,Cooke,Finlayson

, p. 348 (1920)

-

SELECTIVE REDUCTION OF ALDEHYDES

Sorrell, Thomas N.,Pearlman, Paul S.

, p. 3963 - 3964 (1980)

Tetraethylammonium borohydride performs the selective reduction of aldehydes under mild conditions.

On-the-fly Catalyst Accretion and Screening in Chemoselective Flow Hydrogenation

Giziński, Damian,B?achucki, Wojciech,?r?bowata, Anna,Zienkiewicz-Machnik, Ma?gorzata,Goszewska, Ilona,Matus, Krzysztof,Lisovytskiy, Dmytro,Pisarek, Marcin,Szlachetko, Jakub,Sá, Jacinto

, p. 3641 - 3646 (2018)

Herein, it is reported an on-the-fly accretion/reaction protocol to evaluate the structure-performance relationship in the chemoselective flow citral hydrogenation over Ni-based catalysts. Based on the methodology one was able to determine Ni nanoparticles ideal average size (ca. 9 nm), in a rapid and facile manner. The methodology offers a simple workflow, cost-effective and adaptable strategy for process intensification and optimization.

Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

Er?nen, Kari,M?ki-Arvela, P?ivi,Martinez-Klimov, Mark,Muller, Joseph,Murzin, Dmitry Yu.,Peurla, Markus,Simakova, Irina,Vajglova, Zuzana

, (2022/04/03)

One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

Deep eutectic solvents as H2-sources for Ru(II)-catalyzed transfer hydrogenation of carbonyl compounds under mild conditions

Cavallo, Marzia,Arnodo, Davide,Mannu, Alberto,Blangetti, Marco,Prandi, Cristina,Baratta, Walter,Baldino, Salvatore

supporting information, (2021/02/22)

The employment of easily affordable ruthenium(II)-complexes as pre-catalysts in the transfer hydrogenation of carbonyl compounds in deep eutectic media is described for the first time. The eutectic mixture tetrabutylammonium bromide/formic acid = 1/1 (TBABr/HCOOH = 1/1) acts both as reaction medium and hydrogen source. The addition of a base is required for the process to occur. An extensive optimization of the reaction conditions has been carried out, in terms of catalyst loading, type of complexes, H2-donors, reaction temperature and time. The combination of the dimeric complex [RuCl(p-cymene)-μ-Cl]2 (0.01–0.05 eq.) and the ligand dppf (1,1′-ferrocenediyl-bis(diphenylphosphine)ferrocene) in 1/1 molar ratio has proven to be a suitable catalytic system for the reduction of several and diverse aldehydes and ketones to their corresponding alcohols under mild conditions (40–60 °C) in air, showing from moderate to excellent tolerability towards different functional groups (halogen, cyano, nitro, phenol). The reduction of imine compounds to their corresponding amine derivatives was also studied. In addition, the comparison between the results obtained in TBABr/HCOOH and in organic solvents suggests a non-innocent effect of the DES medium during the process.

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