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106-89-8

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106-89-8 Usage

General Description

1-Chloro-2,3-epoxypropane, also known as glycidyl chloride, is an organic compound with the chemical formula C3H5ClO. It is a colorless liquid with a sharp, irritating odor and is commonly used in the synthesis of various organic compounds. It is also used as a reagent in organic reactions and as a precursor in the production of polymers and plastics. 1-Chloro-2,3-epoxypropane is highly reactive and can polymerize in the presence of impurities, making it important to handle with caution. The compound is considered toxic and is harmful if swallowed, inhaled, or in contact with skin. It is also a potential carcinogen and should be handled and disposed of with care to prevent harm to human health and the environment.

Check Digit Verification of cas no

The CAS Registry Mumber 106-89-8 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, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 106-89:
(5*1)+(4*0)+(3*6)+(2*8)+(1*9)=48
48 % 10 = 8
So 106-89-8 is a valid CAS Registry Number.
InChI:InChI=1/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2

106-89-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A15823)  (±)-Epichlorohydrin, 99%   

  • 106-89-8

  • 100g

  • 201.0CNY

  • Detail
  • Alfa Aesar

  • (A15823)  (±)-Epichlorohydrin, 99%   

  • 106-89-8

  • 500g

  • 257.0CNY

  • Detail
  • Alfa Aesar

  • (A15823)  (±)-Epichlorohydrin, 99%   

  • 106-89-8

  • 2500g

  • 685.0CNY

  • Detail
  • Sigma-Aldrich

  • (02578)  (±)-Epichlorohydrin  analytical standard

  • 106-89-8

  • 02578-1ML

  • 386.10CNY

  • Detail
  • Sigma-Aldrich

  • (45340)  (±)-Epichlorohydrin  purum, ≥99% (GC)

  • 106-89-8

  • 45340-500ML-F

  • 237.51CNY

  • Detail
  • Sigma-Aldrich

  • (45340)  (±)-Epichlorohydrin  purum, ≥99% (GC)

  • 106-89-8

  • 45340-1L-F

  • 601.38CNY

  • Detail
  • Sigma-Aldrich

  • (45340)  (±)-Epichlorohydrin  purum, ≥99% (GC)

  • 106-89-8

  • 45340-2.5L-F

  • 1,193.40CNY

  • Detail

106-89-8Synthetic route

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With Cumene hydroperoxide at 60 - 120℃; under 7500.75 Torr; Temperature; Pressure;99%
With Cumene hydroperoxide at 60 - 120℃; under 7500.75 Torr; Temperature; Pressure;98%
With 1-phenylethyl hydroperoxide In ethylbenzene at 30 - 50℃; under 750.075 Torr; Pressure; Temperature; Reagent/catalyst;98%
1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With resin IRA-440 In dichloromethane for 24h; Ambient temperature;98%
With strong basic ion-exchange resin IRA 440 In dichloromethane for 24h; Product distribution; Ambient temperature; other basic ion-exchange resins; other glycerol dihalohydrins; other solvents and time;98%
With calcium hydroxide inactive form;
(C4H9)3SnOCH(CH2Cl)2
35952-61-5

(C4H9)3SnOCH(CH2Cl)2

A

tributyltin chloride
1461-22-9

tributyltin chloride

B

chloroacetone
78-95-5

chloroacetone

C

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
63% decompn. at 210°C (1 h);A n/a
B 5%
C 95%
γ,γ-dichloropropanol
83682-72-8

γ,γ-dichloropropanol

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With sodium hydroxide at 20℃; Temperature;94.1%
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

A

1-chloro-3-methoxypropan-2-ol
4151-97-7

1-chloro-3-methoxypropan-2-ol

B

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

C

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With dihydrogen peroxide; TS-1 In methanol; water; 1,2-dichloro-benzene at 25 - 40℃; for 1h; Product distribution / selectivity;A n/a
B n/a
C 94%
2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With water; sodium hydroxide at 50℃; for 0.00833333h; Time; Temperature; Concentration;92.4%
With potassium hydroxide
oxiranyl-methanol
556-52-5

oxiranyl-methanol

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 0 - 20℃; Inert atmosphere;85%
1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

A

chloroacetone
78-95-5

chloroacetone

B

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With HT4-c823 In water at 149.84℃; under 750.075 Torr; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature; Flow reactor; chemoselective reaction;A 18.9%
B 80.5%
(R,S)-2-hydroxy-3-chloropropyl p-toluenesulfonate
102129-99-7

(R,S)-2-hydroxy-3-chloropropyl p-toluenesulfonate

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With sodium ethane-1,2-diolate In ethylene glycol at 20℃; for 0.25h;79%
(+/-)-1-Acetoxy-2,3-dichloropropane
589-96-8

(+/-)-1-Acetoxy-2,3-dichloropropane

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With calcium hydroxide 1.) H2O, r.t., 1 h, 2.) hexane, 6 h;77%
glycerol
56-81-5

glycerol

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
Stage #1: glycerol With hydrogenchloride; Adipic acid In water at 120℃; for 8h;
Stage #2: With calcium hydroxide
67.5%
With phosphorus trichloride
With hydrogenchloride anschl. mit Aetzkali;
1-bromo-3-chloro-propan-2-ol
4540-44-7

1-bromo-3-chloro-propan-2-ol

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With sodium ethane-1,2-diolate In ethylene glycol at 20℃; for 0.25h;58%
With potassium hydroxide levorotatory form;
2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

A

(2R)-3-chloro-1,2-propanediol
57090-45-6

(2R)-3-chloro-1,2-propanediol

B

(S)-3-chloropropan-1,2-diol
60827-45-4

(S)-3-chloropropan-1,2-diol

C

(S)-1,3-dichloro-1-propanol

(S)-1,3-dichloro-1-propanol

D

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With epoxide hydrolase from Agrobacterium radiobacter AD1; halohydrin dehalogenase from Agrobacterium radiobacter AD1; Tris-SO4 buffer In water at 30℃; for 20h; pH=7.5; kinetic resolution; Further byproducts given;A n/a
B n/a
C 49.5%
D n/a
dihydrogen peroxide
7722-84-1

dihydrogen peroxide

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

A

water
7732-18-5

water

B

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With titanium-containing zeolite In methanol at 35℃; Mechanism; Solvent;A n/a
B 29.8%
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

A

benzaldehyde
100-52-7

benzaldehyde

B

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With molybdenum blue; dihydrogen peroxide; bis(tri-n-butyltin)oxide In chloroform at 25℃; for 10h;A 1%
B 48 % Turnov.
1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

A

glycerol
56-81-5

glycerol

B

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With potassium hydroxide
1,3-dichloro-2-acetoxypropane
3674-10-0

1,3-dichloro-2-acetoxypropane

A

acetyl chloride
75-36-5

acetyl chloride

B

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
beim Stehenlassen;
peracetic acid
79-21-0

peracetic acid

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With catalysts
(+-)-2,3-dichloro-propan-1-ol

(+-)-2,3-dichloro-propan-1-ol

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
With calcium hydroxide
With sodium hydroxide Herstellung eines mit Chlor-36 markierten Praeparats;
1-bromo-3-chloro-propan-2-ol
4540-44-7

1-bromo-3-chloro-propan-2-ol

potash

potash

A

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

B

epichlorohydrin
106-89-8

epichlorohydrin

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

KOH

KOH

epichlorohydrin
106-89-8

epichlorohydrin

2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

potash

potash

epichlorohydrin
106-89-8

epichlorohydrin

2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

water
7732-18-5

water

sodium hydroxide

sodium hydroxide

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
at 0℃;
at 0℃; Geschwindigkeit;
at 25℃; Geschwindigkeit;
1-chloro-3-iodopropan-2-ol
26484-95-7

1-chloro-3-iodopropan-2-ol

KOH-solution

KOH-solution

A

hydrogen iodide
10034-85-2

hydrogen iodide

B

epichlorohydrin
106-89-8

epichlorohydrin

diethyl ether
60-29-7

diethyl ether

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

water
7732-18-5

water

sodium amalgam

sodium amalgam

A

allyl alcohol
107-18-6

allyl alcohol

B

epichlorohydrin
106-89-8

epichlorohydrin

diethyl ether
60-29-7

diethyl ether

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

sodium

sodium

A

propene
187737-37-7

propene

B

allyl alcohol
107-18-6

allyl alcohol

C

epichlorohydrin
106-89-8

epichlorohydrin

ethanol
64-17-5

ethanol

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

powdered NaOH

powdered NaOH

A

1,3-diethoxy-isopropanol
4043-59-8

1,3-diethoxy-isopropanol

B

epichlorohydrin
106-89-8

epichlorohydrin

C

glycidethyl ether

glycidethyl ether

3-hydroxy-benzoic acid-(2-chloro-1-chloromethyl-ethyl ester)

3-hydroxy-benzoic acid-(2-chloro-1-chloromethyl-ethyl ester)

potash

potash

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
at 100℃;
morpholine
110-91-8

morpholine

epichlorohydrin
106-89-8

epichlorohydrin

1-chloro-3-(4-morpholinyl)-2-propanol
40893-69-4

1-chloro-3-(4-morpholinyl)-2-propanol

Conditions
ConditionsYield
In ethanol for 24h; Heating;100%
With zinc(II) chloride In water at 60℃; for 8h; regioselective reaction;96%
In water at 0 - 5℃; for 4h;92%
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

epichlorohydrin
106-89-8

epichlorohydrin

ethyl 4-(glycidyloxy)benzoate
50625-94-0

ethyl 4-(glycidyloxy)benzoate

Conditions
ConditionsYield
With sodium carbonate; N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;100%
With potassium carbonate In acetone for 20h; Heating;
With potassium carbonate In butanone Heating;
With potassium carbonate In acetone; toluene13.5 gm (61%)
With sodium hydroxide
acetic acid
64-19-7

acetic acid

epichlorohydrin
106-89-8

epichlorohydrin

3-chloro-2-hydroxy-1-propyl acetate
24573-30-6

3-chloro-2-hydroxy-1-propyl acetate

Conditions
ConditionsYield
With iron(III) chloride at 20 - 70℃; for 24.1667h;100%
With tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate for 0.666667h; Heating;99%
With cerium(IV) triflate at 80℃; for 0.0833333h;93%
epichlorohydrin
106-89-8

epichlorohydrin

phenol
108-95-2

phenol

Phenyl glycidyl ether
122-60-1

Phenyl glycidyl ether

Conditions
ConditionsYield
Stage #1: phenol With sodium hydroxide In water at 25℃; for 0.666667h;
Stage #2: epichlorohydrin In water at 30 - 35℃; for 16h;
100%
With n-Bu4NOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h;91%
With n-BuNOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h; other aryl alcohols, var. phase transfer catalysts, var. reaction time;91%
epichlorohydrin
106-89-8

epichlorohydrin

1-bromo-3-chloro-propan-2-ol
4540-44-7

1-bromo-3-chloro-propan-2-ol

Conditions
ConditionsYield
With hydrogen bromide at -60℃; for 16h;100%
With dimethylbromosulphonium bromide In acetonitrile at 20℃; for 0.333333h;98%
With ammonium cerium(IV) nitrate; tetrabutylammomium bromide In tert-butyl alcohol for 1.5h; Ambient temperature;96%
epichlorohydrin
106-89-8

epichlorohydrin

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane for 12h; Ambient temperature;100%
With hydrogenchloride In water100%
With chloro-trimethyl-silane; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 1h; ring opening reaction;99%
epichlorohydrin
106-89-8

epichlorohydrin

bis(3-chloro-2-hydroxypropyl)sulfide
19030-86-5

bis(3-chloro-2-hydroxypropyl)sulfide

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogen sulfide monohydrate; sodium hydroxide In methanol; water at 6℃;100%
With hydrogen sulfide; tetrabutylammomium bromide In toluene at 20 - 25℃; Solvent; Temperature; Reagent/catalyst;96%
With hydrogen sulfide
diisopropylamine
108-18-9

diisopropylamine

epichlorohydrin
106-89-8

epichlorohydrin

1-Chlor-2-hydroxy-3-diisopropylamino-methyl-propan
55211-97-7

1-Chlor-2-hydroxy-3-diisopropylamino-methyl-propan

Conditions
ConditionsYield
In ethanol for 24h; Heating;100%
In water
aniline
62-53-3

aniline

epichlorohydrin
106-89-8

epichlorohydrin

N-(3-chloro-2-hydroxypropyl)aniline
76226-32-9, 15949-12-9

N-(3-chloro-2-hydroxypropyl)aniline

Conditions
ConditionsYield
With lithium bromide at 20℃; for 5h;100%
With Ni2+-metallodendrimer grafted on mesoporous polymethacrylate based Sepabeads EB-EP-400 In neat (no solvent) at 20℃; for 0.5h; Reagent/catalyst; Solvent; Green chemistry; regioselective reaction;97%
With BiCl6(3-)*2C4H10N2*ClH*3H(1+)*H2O at 20℃; for 0.116667h; Neat (no solvent); regioselective reaction;96%
pyrrolidine
123-75-1

pyrrolidine

epichlorohydrin
106-89-8

epichlorohydrin

1-chloro-3-(1-pyrrolidinyl)-2-propanol
58759-70-9

1-chloro-3-(1-pyrrolidinyl)-2-propanol

Conditions
ConditionsYield
In ethanol for 24h; Heating;100%
In ethanol at 20℃; under 2585.81 Torr; for 0.0166667h; microwave irradiation;65%
(2-hydroxyethyl)(methyl)amine
109-83-1

(2-hydroxyethyl)(methyl)amine

epichlorohydrin
106-89-8

epichlorohydrin

1-Chlor-2-hydroxy-3-(N-methyl-N-2-hydroxyethyl)-amino-propan
63125-83-7

1-Chlor-2-hydroxy-3-(N-methyl-N-2-hydroxyethyl)-amino-propan

Conditions
ConditionsYield
at 40 - 70℃;100%
In water at 13 - 34℃; for 1.41667h;
In isopropyl alcohol
1H-indol-4-ol
2380-94-1

1H-indol-4-ol

epichlorohydrin
106-89-8

epichlorohydrin

4-(oxiranylmethoxy)-1H-indole
35308-87-3

4-(oxiranylmethoxy)-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h;100%
Stage #1: 1H-indol-4-ol; epichlorohydrin With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h;
Stage #2: With ammonium chloride In water
99%
With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h;99%
4-phenyl-Δ2-1,2,4-triazoline-5-thione
5373-72-8

4-phenyl-Δ2-1,2,4-triazoline-5-thione

epichlorohydrin
106-89-8

epichlorohydrin

4-phenyl-3-(1-chloro-2-hydroxypropylthio)-1,2,4-triazole
134619-57-1

4-phenyl-3-(1-chloro-2-hydroxypropylthio)-1,2,4-triazole

Conditions
ConditionsYield
In ethanol at 20℃; for 5h;100%
1-octadecanol
112-92-5

1-octadecanol

epichlorohydrin
106-89-8

epichlorohydrin

octadecyl glycidyl ether
16245-97-9

octadecyl glycidyl ether

Conditions
ConditionsYield
With sodium hydroxide; Aliquat 336 In cyclohexane Heating;100%
With sodium hydroxide; Aliquat 336 In cyclohexane Heating;99%
With sodium hydroxide; Aliquat 336 In cyclohexane for 4h; Heating;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

epichlorohydrin
106-89-8

epichlorohydrin

4-chloro-3-trimethylsiloxybutyronitrile
81091-27-2

4-chloro-3-trimethylsiloxybutyronitrile

Conditions
ConditionsYield
With erbium(III) triflate at 0 - 20℃; for 0.166667h; regioselective reaction;100%
ytterbium cyanide In tetrahydrofuran at 25℃; for 0.3h;91%
carbon dioxide
124-38-9

carbon dioxide

epichlorohydrin
106-89-8

epichlorohydrin

4-chloromethyl-[1,3]dioxolan-2-one
2463-45-8

4-chloromethyl-[1,3]dioxolan-2-one

Conditions
ConditionsYield
With dmap; CrTTPCl at 60℃; under 37751.8 - 40337.5 Torr; for 18h;100%
With triphenylphosphine; phenol at 120℃; under 30002.4 Torr; for 14h;100%
With triethylamine; binaphthyldiamino Zn(II) salen-type compex In dichloromethane at 100℃; under 25858.1 Torr;100%
Cyclododecylamine
1502-03-0

Cyclododecylamine

epichlorohydrin
106-89-8

epichlorohydrin

1-Chloro-3-cyclododecylamino-propan-2-ol

1-Chloro-3-cyclododecylamino-propan-2-ol

Conditions
ConditionsYield
In ethanol for 24h; Heating;100%
isoselenocyanatotrimethylsilane
16966-40-8

isoselenocyanatotrimethylsilane

epichlorohydrin
106-89-8

epichlorohydrin

3-Chloro-2-trimethylsiloxypropyl selenocyanate
128256-05-3

3-Chloro-2-trimethylsiloxypropyl selenocyanate

Conditions
ConditionsYield
potassium selenocyanate In hexane at 40℃; for 24h;100%
cyclooctylamine
5452-37-9

cyclooctylamine

epichlorohydrin
106-89-8

epichlorohydrin

1-Chloro-3-cyclooctylamino-propan-2-ol

1-Chloro-3-cyclooctylamino-propan-2-ol

Conditions
ConditionsYield
In ethanol for 24h; Heating;100%
pyridinium perchlorate
15598-34-2

pyridinium perchlorate

epichlorohydrin
106-89-8

epichlorohydrin

1-(2-hydroxy-3-chloropropyl)pyridinium perchlorate

1-(2-hydroxy-3-chloropropyl)pyridinium perchlorate

Conditions
ConditionsYield
With pyridine In ethanol for 3h; Product distribution; Heating; further cycloimmonium salts;100%
With pyridine In ethanol for 3h; Heating;100%
4-methylpyridinium perchlorate
52827-74-4

4-methylpyridinium perchlorate

epichlorohydrin
106-89-8

epichlorohydrin

1-(2-hydroxy-3-chloropropyl)-4-methylpyridinium perchlorate

1-(2-hydroxy-3-chloropropyl)-4-methylpyridinium perchlorate

Conditions
ConditionsYield
With picoline for 1h; Heating;100%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

epichlorohydrin
106-89-8

epichlorohydrin

1,3-dichloro-2-propyl cinnamate
157140-94-8

1,3-dichloro-2-propyl cinnamate

Conditions
ConditionsYield
With yttrium(III) chloride In dichloromethane for 36h; Ambient temperature;100%
N-(1-chlorohexafluoro-1-methylethyl)benzenesulfinimidoyl chloride
85095-40-5

N-(1-chlorohexafluoro-1-methylethyl)benzenesulfinimidoyl chloride

epichlorohydrin
106-89-8

epichlorohydrin

C12H10Cl3F6NOS
91363-16-5

C12H10Cl3F6NOS

Conditions
ConditionsYield
In tetrachloromethane at 25℃; for 48h;100%
N-(2-chlorohexafluoroisopropyl)-p-toluenesulfinimidoyl chloride
85095-41-6

N-(2-chlorohexafluoroisopropyl)-p-toluenesulfinimidoyl chloride

epichlorohydrin
106-89-8

epichlorohydrin

C13H12Cl3F6NOS
91363-17-6

C13H12Cl3F6NOS

Conditions
ConditionsYield
In tetrachloromethane at 25℃; for 48h;100%
N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

epichlorohydrin
106-89-8

epichlorohydrin

1-Chloro-3-dicyclohexylamino-propan-2-ol
150389-77-8

1-Chloro-3-dicyclohexylamino-propan-2-ol

Conditions
ConditionsYield
In ethanol for 24h; Heating;100%
(2-trimethylsilylprop-2-en-1-yl)tributylstannane
151073-99-3

(2-trimethylsilylprop-2-en-1-yl)tributylstannane

epichlorohydrin
106-89-8

epichlorohydrin

1-Chloro-5-(trimethylsilyl)-5-hexen-2-ol

1-Chloro-5-(trimethylsilyl)-5-hexen-2-ol

Conditions
ConditionsYield
With ethylaluminum dichloride In dichloromethane at -78℃; for 19h;100%
2-Allylphenol
1745-81-9

2-Allylphenol

epichlorohydrin
106-89-8

epichlorohydrin

1-(2-allyl-phenoxy)-3-chloro-propan-2-ol
49716-04-3

1-(2-allyl-phenoxy)-3-chloro-propan-2-ol

Conditions
ConditionsYield
With pyridine In chloroform; water; phenol100%
With piperidine Heating;
epichlorohydrin
106-89-8

epichlorohydrin

p-cyclohexylphenol
1131-60-8

p-cyclohexylphenol

2-[(4-cyclohexylphenoxy)methyl]oxirane
67006-99-9

2-[(4-cyclohexylphenoxy)methyl]oxirane

Conditions
ConditionsYield
With sodium hydroxide for 1h; Reflux;100%
With sodium In isopropyl alcohol 1.) 10 min., reflux, 2.) 16 h., room temp.;
epichlorohydrin
106-89-8

epichlorohydrin

bis(2-bromo-2-chloropropyl)(2-bromo-3-chloropropyl)phosphonate
36636-44-9

bis(2-bromo-2-chloropropyl)(2-bromo-3-chloropropyl)phosphonate

Conditions
ConditionsYield
With phosphorus tribromide at 0 - 40℃;100%
epichlorohydrin
106-89-8

epichlorohydrin

phenol
108-95-2

phenol

(R)-1-chloro-3-phenoxy-2-propanol
140630-45-1

(R)-1-chloro-3-phenoxy-2-propanol

Conditions
ConditionsYield
With chiral oligo-(salen)Co(OTs) complexes; lutidinium p-toluene sulfonate In acetonitrile at 4℃; for 4h;100%
With (R,R)-(salen)Co(H2O); 3 A molecular sieve In various solvent(s) at -15℃;97%
With C57H68N4O8(2-)*Co(3+)*C7H7O3S(1-); C56H66N2O6(2-)*Co(3+)*C7H7O3S(1-) In tetrachloromethane at 4 - 20℃; for 6h; stereoselective reaction;95%
With Co(salen) macrocycles 1(OTs) In tert-butyl methyl ether at 20℃; for 9h; optical yield given as %ee; enantioselective reaction;91%
With Co(salen) macrocycles 1(OTs) In tert-butyl methyl ether at 20℃; Kinetics; enantioselective reaction;

106-89-8Relevant articles and documents

Mechanism of olefin epoxidation in the presence of a titanium-containing zeolite

Danov,Krasnov,Sulimov,Ovcharova

, p. 1809 - 1812 (2013)

The effect of the nature of a solvent on the liquid-phase epoxidation of olefins with an aqueous solution of hydrogen peroxide over a titanium-containing zeolite is studied. Butanol-1, butanol-2, propanol-1, isopropanol, methanol, ethanol, water, acetone, methyl ethyl ketone, isobutanol, and tert-butanol are examined as solvents. A mechanism of olefin epoxidation with hydrogen peroxide in an alcohol medium over a titanium-containing zeolite is proposed. Epoxidation reactions involving hydrogen peroxide and different olefins are studied experimentally.

Continuous flow upgrading of glycerol toward oxiranes and active pharmaceutical ingredients thereof

Morodo, Romain,Gérardy, Romaric,Petit, Guillaume,Monbaliu, Jean-Christophe M.

, p. 4422 - 4433 (2019)

A robust continuous flow procedure for the transformation of bio-based glycerol into high value-added oxiranes (epichlorohydrin and glycidol) is presented. The flow procedure features a central hydrochlorination/dechlorination sequence and provides economically and environmentally favorable conditions involving an organocatalyst and aqueous solutions of hydrochloric acid and sodium hydroxide. Pimelic acid (10 mol%) shows an exceptional catalytic activity (>99% conversion of glycerol, a high selectivity toward 1,3-dichloro-2-propanol and 81% cumulated yield toward intermediate chlorohydrins) for the hydrochlorination of glycerol (140 °C) with 36 wt% aqueous HCl. These conditions are validated on a sample of crude bio-based glycerol. The dechlorination step is effective (quantitative conversion based on glycerol) with concentrated aqueous sodium hydroxide (20 °C) and can be directly concatenated to the hydrochlorination step, hence providing a ca. 2:3 separable mixture of glycidol and epichlorohydrin (74% cumulated yield). An in-line membrane separation unit is included downstream, providing usable streams of epichlorohydrin (in MTBE, with an optional concentrator) and glycidol (in water). The scalability of the dechlorination step is then assessed in a commercial pilot-scale continuous flow reactor. Next, bio-based epichlorohydrin is further utilized for the continuous flow preparation of β-amino alcohol active pharmaceutical ingredients including propranolol (hypertension, WHO essential), naftopidil (prostatic hyperplasia) and alprenolol (angina pectoris) within a concatenable two-step procedure using a FDA class 3 solvent (DMSO). This work provides the first example of direct upgrading of bio-based glycerol into high value-added pharmaceuticals under continuous flow conditions.

Controlling the Morphology and Titanium Coordination States of TS-1 Zeolites by Crystal Growth Modifier

Chang, Xinyu,Chen, Ziyi,Hu, Dianwen,Jia, Mingjun,Li, Yingying,Song, Xiaojing,Yang, Xiaotong,Yu, Jihong,Zhang, Hao,Zhang, Peng,Zhang, Qiang,Zhang, Tianjun

, p. 13201 - 13210 (2020)

Developing an effective strategy to synthesize perfect titanosilicate TS-1 zeolite crystals with desirable morphologies, enriched isolated framework Ti species, and thus enhanced catalytic oxidation properties is a pervasive challenge in zeolite crystal engineering. We here used an amino acid l-carnitine as a crystal growth modifier and ethanol as a cosolvent to regulate the morphologies and the Ti coordination states of TS-1 zeolites. During the hydrothermal crystallization process, the introduced l-carnitine can not only tailor the anisotropic growth rates of zeolite crystals but also induce the formation of uniformly distributed framework Ti species through building a suitable chemical interaction with the Ti precursor species. Condition optimizations could afford the generation of perfect hexagonal plate TS-1 crystals and elongated platelet TS-1 crystals enriched in tetrahedral framework Ti sites (TiO4) or mononuclear octahedrally coordinated Ti species (TiO6). Both samples showed significant improvement in catalytic activity for the H2O2-mediated epoxidation of alkenes. In particular, the elongated platelet TS-1 enriched in "TiO6"species afforded the highest activity in 1-hexene epoxidation, with a turnover frequency (TOF) of up to 131 h-1, which is approximately twice as high as that of the conventional TS-1 zeolite (TOF: 65 h-1) and even higher than those of the literature-reported TiO6-containting TS-1 catalysts derived from the hydrothermal post-treatment of TS-1 zeolites. This work demonstrates that the morphologies and the titanium coordination states of TS-1 zeolites can be effectively tuned by directly introducing suitable crystal growth modifiers, thus providing new opportunities for developing highly efficient titanosilicate zeolite catalysts for important catalytic applications.

A New, Effective Catalytic System for Epoxidation of Olefins by Hydrogen Peroxide under Phase-Transfer Conditions

Venturello, Carlo,Alneri, Enzo,Ricci, Marco

, p. 3831 - 3833 (1983)

-

Converting wastes into added value products: From glycerol to glycerol carbonate, glycidol and epichlorohydrin using environmentally friendly synthetic routes

Dibenedetto, Angela,Angelini, Antonella,Aresta, Michele,Ethiraj, Jayashree,Fragale, Carlo,Nocito, Francesco

, p. 1308 - 1313 (2011)

Glycerol carbonate, synthesised via a non-phosgene route using glycerol and CO2 or urea in presence of a heterogeneous catalyst, was efficiently converted into a series of derivatives through the functionalization of the -OH moiety, using high yield, high selectivity synthetic routes not affecting the carbonate functionality. So, for example, glycerol carbonate was converted into epichlorohydrin, a product that has a large industrial application, under very mild conditions, using a two-step reaction with a 98% yield and 100% selectivity. The high yield and mild reaction conditions (very often close to the ambient conditions) make the environmentally friendly synthetic approach described in this work of potential applicative interest. All compounds prepared were fully characterized.

Synthesis of 1,3-dichloropropanol from glycerol using muriatic acid as chlorinating agent

Herliati,Yunus, Robiah,Rashid, Umer,Abidin, Zurina Zainal,Ahamad, Intan Salwani

, p. 2907 - 2912 (2014)

Today, one of the problems associated with biodiesel production is the availability of high amount of glycerol byproduct. Among the various possibilities, technology to convert glycerol to dichloropropanol has diverted our attention. Dichloropropanol an important raw material for epichlorohydrin production was successfully synthesized via hydrochlorination reaction of glycerol with aqueous hydrogen chloride to produce 1,3-dichloropropanol. Experimental study was carried out under temperatures ranged; 80 to 120 °C, reactant molar ratio; 1:16 to 1:32 and various carboxylic acid catalysts. The optimal reaction conditions were: temperature, 110 °C; reactant molar ratio glycerol to HCl, 1:24; catalyst, malonic acid; and time duration, 3 h.

Highly efficient and selective production of epichlorohydrin through epoxidation of allyl chloride with hydrogen peroxide over Ti-MWW catalysts

Wang, Lingling,Liu, Yueming,Xie, Wei,Zhang, Haijiao,Wu, Haihong,Jiang, Yongwen,He, Mingyuan,Wu, Peng

, p. 205 - 214 (2007)

The catalytic properties of Ti-MWW in the epoxidation of allyl chloride (ALC) with hydrogen peroxide to epichlorohydrin (ECH) were studied by comparing these properties with those of TS-1, Ti-MOR, and Ti-Beta. Issues concerning the stability and reuse of Ti-MWW were also considered. The investigation on various reaction parameters showed that Ti-MWW is an active and selective catalyst for ALC epoxidation. Ti-MWW prefers aprotic solvents, such as acetonitrile and acetone, over protic alcohols, which is favorable for suppressing the formation of solvolysis byproducts. ALC conversion and ECH selectivity were both as high as 99% on Ti-MWW. 3-Chloro-1,2-propanediol and other heavy byproducts with high boiling points had a negative effect on ALC conversion for both TS-1 and Ti-MWW. A novel secondary synthesis caused a structural rearrangement of the Ti-MWW framework and then improved its stability.

Enhanced catalytic activity of titanosilicates controlled by hydrogen-bonding interactions

Deng, Xiujuan,Zhang, Shuo,Wang, Binshen,Wang, Yuning,Wu, Haihong,Liu, Yueming,He, Mingyuan

, p. 7504 - 7506 (2013)

A typical volcano-shaped curve has been found in heterogeneous catalytic systems containing titanosilicates for the first time. A new reactive intermediate with double H-bonds is proposed. Systematic results clearly evidence another H-bond formed between the high-electronegativity atom of the H-bond acceptor and the Hend atom of Ti-Oα-O β-Hend.

Solvent effect on epoxidation of allyl chloride with hydrogen peroxide on titanium-containing silicalite

Danov,Sulimov,Sulimova

, p. 1963 - 1966 (2008)

The solvent effect on liquid-phase epoxidation of allyl chloride with an aqueous solution of hydrogen peroxide on TS-1 titanium-containing silicalite was examined. 1-Butanol, 2-butanol, 1-propanol, isopropanol, methanol, ethanol, water, acetone, methyl ethyl ketone, and 1-pentanol were tested as solvents.

Synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate in high concentration using a novel halohydrin dehalogenase HHDH-PL from Parvibaculum lavamentivorans DS-1

Wan, Nan-Wei,Liu, Zhi-Qiang,Huang, Kai,Shen, Zhen-Yang,Xue, Feng,Zheng, Yu-Guo,Shen, Yin-Chu

, p. 64027 - 64031 (2014)

We identified and characterized a novel halohydrin dehalogenase HHDH-PL from Parvibaculum lavamentivorans DS-1. Study of substrate specificity indicated that HHDH-PL possessed a high activity toward ethyl (S)-4-chloro-3-hydroxybutanoate ((S)-CHBE). After optimizations of the pH and temperature, whole cell catalysis of HHDH-PL was applied to the synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate (HN) at 200 g L-1 of (S)-CHBE, which gave 95% conversion and 85% yield in 14 h.

Synthesis and enzymatic resolution of racemic 2,3-epoxy propyl esters obtained from glycerol

Araujo, Yara Jaqueline Kerber,Avvari, Naga Prasad,Paiva, Derisvaldo Rosa,De Lima, Dênis Pires,Beatriz, Adilson

, p. 1696 - 1698 (2015)

A method is described for the synthesis of (±)-2,3-epoxy propyl esters from glycerol, involving reaction of epichlorohydrin with sodium or potassium salts of carboxylic acids in the presence of TBAB as catalyst, with moderate to excellent yields. Kinetic resolution of glycidyl butyrate by lipase of Thermomyces lanuginosa has been achieved with remarkable enantiomeric excess (ee >99%) using 1,4-dioxane as a co-solvent in pure buffer solution (30 and 50 °C, pH = 7.0).

EPOXIDIZATION OF ALLYL CHLORIDE BY COMBINED OXIDATION WITH ETHYLBENZENE ON LAYERED COMPOUNDS OF GRAPHITE WITH TRANSITION-METAL CHLORIDES

Kovtyukhova, N. I.,Belousov, V. M.,Novikov, Yu. N.,Vol'pin, M. E.

, p. 1566 - 1570 (1983)

-

Physicochemical relationships of the synthesis of epoxy compounds

Sulimov,Danov,Ovcharova,Ovcharov,Flid

, p. 89 - 96 (2015)

Quantitative information on the effect of process parameters on the main relationships of the liquid-phase epoxidation of propylene, allyl chloride, and allyl alcohol with hydrogen peroxide in an organic solvent in the presence of powdered titanium silicalite in a batch reactor was obtained and summarized for the first time. The influence of the solvent amount, reactant ratio, and temperature was examined, and the area of the process parameters ensuring high yields of the epoxy compounds (propylene oxide, epichlorohydrin, and glycidol) was localized.

Fully utilizing seeds solution for solvent-free synthesized nanosized TS-1 zeolites with efficient epoxidation of chloropropene

Chai, Yongming,Li, Bin,Li, Yichuan,Liu, Hanfang,Liu, Jia,Liu, Yanru,Ran, Saisai,Wang, Fupeng,Wang, Lei,Wang, Yu,Xie, Huijie,Ye, Tiantian

, (2021/12/27)

Nanosized titanium silicalite-1 (TS-1) demonstrates excellent catalytic ability in the selective catalytic oxidation reaction. However, their synthesis process is usually complicated with low yield under hydrothermal conditions, which is not in line with the concept of green chemistry. Herein, via fully utilizing untreated seeds solution, we report firstly an entirely green strategy for solvent-free synthesizing anatase-free nanosized TS-1 zeolite. The success lies in the fully utilization of seeds solution which is composed of supersaturated structure directing agent (TPAOH), unreacted silica source, water and formed MFI seeds (silicalite-1) without external purification. In the followed solvent-free synthesis of final nanosized TS-1 product, no additional TPAOH is added, which greatly reduces the synthesis cost and synthetic procedure and maintains a high product yield. The obtained nanosized TS-1 zeolite without anatase phase has high crystallinity, large specific surface area. More importantly, the nanosized TS-1 (Si/Ti ?= ?77) catalysts exhibit excellent catalytic ability for the epoxidation of chloropropene with 40.0% conversion and 97.6% selectivity. This sustainable and green synthesis method opens up a new way to regulate nanosized zeolite.

Selective synthesis of epichlorohydrin: Via liquid-phase allyl chloride epoxidation over a modified Ti-MWW zeolite in a continuous slurry bed reactor

Ding, Luoyi,Yin, Jinpeng,Tong, Wen,Peng, Rusi,Jiang, Jingang,Xu, Hao,Wu, Peng

, p. 331 - 342 (2021/01/11)

The epoxidation of allyl chloride (ALC) to epichlorohydrin (ECH) with H2O2 using a piperidine (PI)-modified Ti-MWW catalyst (Ti-MWW-PI) in a continuous slurry reactor was investigated to develop an efficient reaction system for the corresponding industrial process. The reaction parameters, including solvent, reaction temperature, t-butanol/ALC mass ratio, ALC/H2O2 molar ratio, weight hourly space velocity of H2O2, and the addition amount of ammonia, were studied in detail to pursue high H2O2 conversion and ECH selectivity. A long catalytic lifetime of 244 h was achieved at high H2O2 conversion (>97.0%) and ECH selectivity (>99.8%) under optimized reaction conditions. The crystallinity was well maintained for the deactivated Ti-MWW-PI catalyst, which was regenerated by a combination of calcination and piperidine treatment. This journal is

A method for efficient preparation of epichlorohydrin by biomass glycerol

-

Paragraph 0040-0041; 0051-0052; 0062-0063; 0073, (2022/01/10)

The present invention discloses a method for efficiently preparing epichlorohydrin by biomass glycerol, comprising the following steps: 1) the mass ratio of 1: 0.06 ~ 0.08 of biomass glycerol and a composite catalyst poured into the reactor, and then using an ultrasonic probe to extend into the reactor, 2) step 1) after the end of the reaction, the resulting material is cooled to room temperature and transferred to the reaction vessel, maintaining a temperature of 15 ~ 30 ° C, and then adding an alkaline cyclizer for the reaction; 3) after the completion of the reaction to filter the resulting solids, The filtrate is a solution of epichlorohydrin oxide; the glycerol of the present invention can be completely converted, the intermediate product dichloropropanol yield is high, and the selectivity of collecting 1,3-dichloropropanol is improved, which accelerates the reaction rate; and the process can be co-produced with biodiesel and chlor-alkali industry, and the industrialization prospect is good.

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