693-89-0

Basic information

• Product Name: 1-Methylcyclopentene
• Synonyms: 1-Cyclopentene, 1-methyl;1-Methyl-1-cyclopentane;1-Methylcyclopentene-1;Cyc1opentene,l-methyl-;cyclopentene,1-methyl-;1-METHYL-1-CYCLOPENTENE;1-METHYLCYCLOPENTENE;METHYL-CYCLOPENTENE
• CAS NO: 693-89-0
• Molecular Formula: C₆H₁₀
• Molecular Weight: 82.14
• EINECS: 211-762-0
• Product Categories: Alkenes;Cyclic;Organic Building Blocks
• Mol File: 693-89-0.mol
• Article Data: 68

Chemical Properties

• Melting Point: -142°C
• Boiling Point: 75-77 °C(lit.)
• Flash Point: 1 °F
• Appearance: Clear colorless/Liquid
• Density: 0.78 g/mL at 25 °C(lit.)
• Vapor Pressure: 103mmHg at 25°C
• Refractive Index: n20/D 1.432
• Storage Temp.: Flammables area
• BRN: 1900640
• CAS DataBase Reference: 1-Methylcyclopentene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methylcyclopentene(693-89-0)
• EPA Substance Registry System: 1-Methylcyclopentene(693-89-0)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-65
• Safety Statements: 16-62-7
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• F: 10-23
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 693-89-0(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

1-Methylcyclopentene can be used as:A probe molecule in the synthesis of alkenyl carbenium ions via adsorption on zeolite Y.A model olefin compound in the kinetic study of hydrogenation of olefins using various catalytic systems.A reactant to synthesize 1,2,3-trisubstituted?benzocyclopentenes by reacting with β-disulfonyl iodonium ylides.

InChI:InChI=1/C6H10/c1-6-4-2-3-5-6/h4H,2-3,5H2,1H3

Synthetic route

methylenecyclopentane (1528-30-9) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
In liquid sulphur dioxide Ambient temperature;	99%
With bromine chloride	67 % Spectr.
With (allylsulfonyl)benzene In Cyclohexane-d12; toluene at 130℃; for 36.5h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures;	95 % Spectr.
With diphenyl disulfone In chloroform-d1 at 80℃; for 1h; Kinetics;

methyllithium (917-54-4) + cyclopentanone (120-92-3) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
Stage #1: methyllithium; cyclopentanone at -10 - 0℃; for 0.5h; Stage #2: With toluene-4-sulfonic acid In 1,2-dichloro-ethane Reflux;	96%
With acid

1-methylcyclopentanol (1462-03-9) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
	95%
With iodine; oxalic acid	87%
With iodine Erhitzen des erhaltenen Gemisches von 1-Methyl-cyclopenten und Methylencyclopentan mit Essigsaeure und wenig Toluol-4-sulfonsaeure;

methyl magnesium iodide (917-64-6) + cyclopentanone (120-92-3) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
Stage #1: methyl magnesium iodide; cyclopentanone In diethyl ether for 1h; Heating; Stage #2: With iodine In toluene for 3h; Heating;	94%
In diethyl ether for 3h; Ambient temperature;	34.8%
2) dehydration; Yield given. Multistep reaction;

methylmagnesium bromide (75-16-1) + cyclopentanone (120-92-3) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
In diethyl ether for 1h;	87%

(hex-5-enyl)magnesium bromide (30043-41-5) → 1-methylcyclopent-1-ene (693-89-0) + Bis(η5-cyclopentadienyl)(η3-hexenyl)titan, 16percent

Conditions	Yield
With isopropylmagnesium bromide; bis(cyclopentadienyl)titanium dichloride In diethyl ether at 36℃; for 5h;	A 66% B n/a

Dimethyl ether (115-10-6) + cyclopentene (142-29-0) → butene isomers; C7 isomers (dimethylcyclopentenes); C6 isomers (methylcyclopentenes); pentene isomers; mixture of + propene (187737-37-7) + ethene (74-85-1) + 1-methylcyclopent-1-ene (693-89-0) + benzene (71-43-2)

Conditions	Yield
MFI280 zeolite at 400℃; under 750.075 Torr; for 20h; Product distribution / selectivity; Gas phase;	A 59.5% B 22.9% C 6% D 9.5% E 2.1%
MTT47 zeolite at 400℃; under 750.075 Torr; for 20h; Product distribution / selectivity; Gas phase;	A 52.2% B 6.7% C 1.4% D 39.3% E 0.4%

cyclohexene (110-83-8) → hexane (110-54-3) + methyl-cyclopentane (96-37-7) + 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
ultrastabilized Y zeolite at 350℃; for 0.0333333h;	A 5.6% B 57.7% C 8.3%

1,5-Hexadien (592-42-7) → (E,Z)-2,4-hexadiene (5194-50-3) + (E)-1,4-hexadiene (7319-00-8) + methylenecyclopentane (1528-30-9) + 1-methylcyclopent-1-ene (693-89-0) + Bis(η5-cyclopentadienyl)(η3-hexenyl)titan, 76 percent

Conditions	Yield
With isopropylmagnesium bromide; bis(cyclopentadienyl)titanium dichloride In diethyl ether at 20℃; for 3h; Further byproducts given. Yields of byproduct given;	A n/a B n/a C n/a D 57% E n/a

cyclohexene (110-83-8) → methylenecyclopentane (1528-30-9) + 1-methylcyclopent-1-ene (693-89-0) + 3-methyl-1-cyclopentene (1120-62-3)

Conditions	Yield
ultrastabilized Y zeolite at 450℃; for 1h;	A 1.7% B 54.4% C 9.9%

cyclohexene (110-83-8) → 1-methylcyclopent-1-ene (693-89-0) + 4-methylcyclopentene (1759-81-5) + 3-methyl-1-cyclopentene (1120-62-3)

Conditions	Yield
ultrastabilized Y zeolite at 450℃; for 1h;	A 54.4% B 4.9% C 9.9%
aluminum hydroxide contg. TiO2 and Na2O at 350℃; Kinetics;
With hydrogenchloride; water In decalin at 225℃; for 49h; Product distribution; Mechanism; in sealed tube; also with DCl/D2O, deuteration investigated; also at 175 deg C;	A 45.2 % Chromat. B n/a C n/a

cyclohexene (110-83-8) → hexane (110-54-3) + methylenecyclopentane (1528-30-9) + methyl-cyclopentane (96-37-7) + 1-methylcyclopent-1-ene (693-89-0) + 4-methylcyclopentene (1759-81-5) + 3-methyl-1-cyclopentene (1120-62-3)

Conditions	Yield
ultrastabilized pprotonic Y zeolite In gas at 350℃; for 1h; Product distribution; Kinetics; other temperatures, other products;	A 0.5% B 1.4% C 1% D 19.6% E 1.8% F 3.6%

D-sorbitol (50-70-4) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
With formaldehyd; ruthenium (III) bromide; hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide In water at 200℃; under 30003 Torr; for 8h;	13%

D-sorbitol (50-70-4) → 1-methylcyclopent-1-ene (693-89-0) + hexanoic acid (142-62-1)

Conditions	Yield
With formaldehyd; ruthenium (III) bromide; hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide In water at 200℃; under 30003 Torr; for 8h;	A 12% B 7%

quinoline (91-22-5) + 1-bromo-1-methyl-cyclopentane (19872-99-2) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
at 190 - 200℃;

methyl magnesium iodide (917-64-6) + 1-chloro-1-methylcyclopentane (6196-85-6) → 1,1-Dimethylcyclopentane (1638-26-2) + 1-methylcyclopent-1-ene (693-89-0)

1-bromo-1-methyl-cyclopentane (19872-99-2) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
With quinoline at 190 - 200℃;
With 1,3,5-triphenylverdasyl at 25℃; Rate constant; other solvents;
In ethanol at 25℃; Kinetics; Further Variations:; Solvents;

1-chloro-1-methylcyclopentane (6196-85-6) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
With water at 35℃;
With quinoline at 160 - 190℃;
With sodium hydroxide In water at 20℃; for 2h; Dehydrochlorination; elimination;
With 1,3,5-triphenylverdazyl In acetonitrile at 25℃; Kinetics; Further Variations:; Solvents; Temperatures;
With 1,3,5-triphenylverdazyl In methanol at 25℃; Kinetics; Further Variations:; Solvents;

1-chloro-1-methylcyclopentane (6196-85-6) → 1-methylcyclopent-1-ene (693-89-0) + 1-methylcyclopentanol (1462-03-9)

Conditions	Yield
With water In ethanol at 30℃; Rate constant; solvolysis reaction;
With calcium hydroxide; water at 35℃;

1-methylcyclopentyl acetate (26600-59-9) → methylenecyclopentane (1528-30-9) + 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
at 450℃;

1-methylcyclopentyl acetate (26600-59-9) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
at 450℃;

3-methylcyclopentanol (18729-48-1) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
With sulfuric acid

1-chloro-2-methyl-cyclopentane (53501-51-2) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
With quinoline at 160 - 190℃;

cyclopentylmethyl acetate (26600-49-7) → methylenecyclopentane (1528-30-9) + 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
at 450 - 570℃;

1-methyl-cyclopentanecarboxylic acid phenyl ester (859181-91-2) → 1-methylcyclopent-1-ene (693-89-0) + phenol (108-95-2)

Conditions	Yield
at 390℃; im Rohr;

1-methylcyclopentanol (1462-03-9) + oxalic acid (144-62-7) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
at 90 - 120℃;

cyclobutylmethylcarbinol (7515-29-9) + oxalic acid (144-62-7) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit Chinolin auf 190-200grad;

1-methylcyclopentanol (1462-03-9) + toluene-4-sulfonic acid (104-15-4) → 1-methylcyclopent-1-ene (693-89-0)

methyl cyclohexane (82166-21-0) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
With chromium (III)-oxide-aluminium oxide contacts at 550℃;

cyclohexene (110-83-8) → 1-methylcyclopent-1-ene (693-89-0)

Conditions	Yield
at 200 - 300℃; Leiten ueber zuvor mit Phosphorsaeure behandeltes Kieselgur;
at 400 - 500℃; Leiten ueber γ-Aluminiumoxyd;

1-methylcyclopent-1-ene (693-89-0) + propionaldehyde (123-38-6) → (methyl-2' cyclopentyl)-1 propanone-1 (81977-75-5)

Conditions	Yield
With dibenzoyl peroxide at 90℃; for 10h;	100%

1-methylcyclopent-1-ene (693-89-0) → 1,2-epoxy-1-methylcyclopentane (16240-42-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 5 - 20℃; Inert atmosphere;	99%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 24℃; for 4h;	84%
With gallium oxide; dihydrogen peroxide; acetonitrile at 89.84℃; for 4h; Sealed tube;	53%

1-methylcyclopent-1-ene (693-89-0) + trifluoromethylpyruvate → (R)-methyl 2-(cyclopentenylmethyl)-3,3,3-trifluoro-2-hydroxypropanoate (1198746-23-4)

Conditions	Yield
With 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine; indium(III) chloride; silver hexafluoroantimonate In 1,2-dichloro-ethane at 20℃; Ionic liquid; Molecular sieve; optical yield given as %ee; enantioselective reaction;	98%

glyoxylic acid ethyl ester (924-44-7) + 1-methylcyclopent-1-ene (693-89-0) → ethyl (R)-3-(cyclopent-1-en-1-yl)-2-hydroxypropanoate (208242-85-7)

Conditions	Yield
With 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine; silver hexafluoroantimonate; indium(III) chloride In 1,2-dichloro-ethane at 20℃; for 16h; Molecular sieve; Inert atmosphere; stereoselective reaction;	98%

1,1-Diphenylmethanol (91-01-0) + 1-methylcyclopent-1-ene (693-89-0) → ((2-methylcyclopent-1-enyl)methylene)dibenzene (1352552-71-6)

Conditions	Yield
With trifluorormethanesulfonic acid In ethylene dibromide at 60℃; Air atmosphere; regioselective reaction;	96%
With N-octadecyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate In dichloromethane at 80℃; for 6h;	92%

1-methylcyclopent-1-ene (693-89-0) + 2-Iodo-2-cyanopent-4-ynenitrile (130575-06-3) → trans-Propargyl-(2-iodo-2-methylcyclopentyl)-malononitrile (141517-23-9)

Conditions	Yield
In benzene at 80℃; for 24h;	95%

methylthiol (74-93-1) + 1-methylcyclopent-1-ene (693-89-0) + diborane (19287-45-7) → bis(trans-2-methylcyclopentyl)(methylthio)borane

Conditions	Yield
With air In tetrahydrofuran byproducts: methylcyclopentane; N2-atmosphere; treatment of B2H6 with olefin, addn. of MeSH (stirring), injecting small amt. of air (in two steps during 2 h), stirring for 12 h; evapn. of volatiles (reduced pressure), fractional distn. (reduced pressure);	95%

1-methylcyclopent-1-ene (693-89-0) + Benzylidenemalononitrile (2700-22-3) → C16H16N2

Conditions	Yield
With 9-(2-mesityl)-10-methylacridinium perchlorate In 1,2-dichloro-ethane at 20℃; Irradiation; Green chemistry; regioselective reaction;	94%

carbon monoxide (201230-82-2) + 1-methylcyclopent-1-ene (693-89-0) → trans-2-Methylcyclopentanecarbaldehyde (20106-44-9)

Conditions	Yield
With dicarbonylacetylacetonato rhodium (I); C37H50NO4P; hydrogen In toluene at 100℃; under 15001.5 Torr; for 12h; Autoclave; regioselective reaction;	92%

1-methylcyclopent-1-ene (693-89-0) + 1,3-Dimethoxybenzene (151-10-0) → 2,4-dimethoxy-1-(1-methylcyclopentyl)benzene (1258741-73-9)

Conditions	Yield
With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V) In dichloromethane at 20℃; for 1h;	91%

trichloro-acetyl bromide (34069-94-8) + 1-methylcyclopent-1-ene (693-89-0) → 7,7-dichloro-1-methylbicyclo[3.2.0]heptan-6-one (51284-43-6)

Conditions	Yield
With zinc In diethyl ether Heating;	90%

1-methylcyclopent-1-ene (693-89-0) + 5-cyano-1H-pyrazole-4-carboxylic acid, ethyl ester (119741-57-0) → 5-cyano-1-(1-methylcyclopentyl)-1H-pyrazole-4-carboxylic acid, ethyl ester (119741-58-1)

Conditions	Yield
With sulfuric acid In dichloromethane; acetonitrile for 2h; Ambient temperature;	90%

1-methylcyclopent-1-ene (693-89-0) + trichloroacetonitrile (545-06-2) → 2,2,2-Trichloro-1-(2-methyl-cyclopent-2-enyl)-ethanone (97963-20-7)

Conditions	Yield
With boron trifluoride; water In dichloromethane at -78℃;	90%

1-methylcyclopent-1-ene (693-89-0) + [Chloro-(3,4-dichloro-phenylsulfanyl)-methyl]-trimethyl-silane (114124-63-9) → 1,2-Dichloro-4-[2-methyl-cyclopent-(E)-ylidenemethylsulfanyl]-benzene

Conditions	Yield
With tin(IV) chloride In dichloromethane at -20℃; for 0.5h;	90%

1-methylcyclopent-1-ene (693-89-0) → (1S,2S)-trans-2-methylcyclopentanol (39947-48-3)

Conditions	Yield
With (R,R)-C6H12BH2(1-)*Li(1+)*OEt2; methyl iodide In diethyl ether for 9.5h; Ambient temperature;	89%

potassium iodomethyltrifluoroborate + 1-methylcyclopent-1-ene (693-89-0) → 1-methylbicyclo[3.1.0]hexane

Conditions	Yield
With dichlorobis(tri-O-tolylphosphine)palladium; potassium carbonate In N,N-dimethyl acetamide; ethylene glycol at 75℃; for 22h; Schlenk technique; Inert atmosphere; Sealed tube;	88%

1-methylcyclopent-1-ene (693-89-0) → 5-oxohexanal (505-03-3)

Conditions	Yield
Stage #1: 1-methylcyclopent-1-ene With ozone In dichloromethane at -78℃; Stage #2: With triphenylphosphine In dichloromethane at -78 - 20℃; for 10h;	87%
Stage #1: 1-methylcyclopent-1-ene With ozone In dichloromethane at -78 - 20℃; Stage #2: With dimethylsulfide In dichloromethane at 20℃; for 5h; Stage #3: With triphenylphosphine In dichloromethane at 20℃; for 5h; Further stages.;	87%
Stage #1: 1-methylcyclopent-1-ene With osmium(VIII) oxide; 4-methylmorpholine N-oxide; tert-butyl alcohol In acetone at 20℃; for 4h; Stage #2: With sodium periodate In water at 20℃; for 1h;	85%

1-methylcyclopent-1-ene (693-89-0) + phenol (108-95-2) → 4-(1-methylcyclopentan-1-yl)phenol (1562-25-0)

Conditions	Yield
With zeolite-P at 80℃; for 3h;	86.4%
cationite KU-23 at 80℃; for 5h; Product distribution; other alkyl- and alkenylcyclenes; var. temp. and time;
cationite KU-23 at 80℃; for 5h;

diiodomethane (75-11-6) + 1-methylcyclopent-1-ene (693-89-0) → 1-methylbicyclo[3.1.0]hexane (4625-24-5)

Conditions	Yield
With diethylzinc In cyclohexane for 120h; Ambient temperature;	86%
With iodine; copper; zinc In diethyl ether

methanol (67-56-1) + 1-methylcyclopent-1-ene (693-89-0) → 1,1-dimethoxy-5-oxo-hexane (36727-63-6)

Conditions	Yield
With Lindlar's catalyst; ozone-containing oxygen; ammonium chloride; sodium methylate 1) -75 Deg C, 2) room temperature, 3) 48 h.;	86%
With dimethylsulfide; ozone 1.) methylene chloride, -78 deg C, 2.) room temperature, 3 h; Multistep reaction;

1-methylcyclopent-1-ene (693-89-0) + 4-nitrosonitrobenzene (4485-08-9) → N-[2-methyl-2-cyclopentenyl]-N-4-nitrophenyl hydroxylamine + N-[2-methenylcyclopentyl]-N-4-nitrophenyl hydroxylamine

Conditions	Yield
In dichloromethane at 0℃; for 24h; Title compound not separated from byproducts.;	A 85% B 15%

{IrH2(acetone)2(PPh3)2}SbF6 (110077-68-4, 89509-77-3) + 1-methylcyclopent-1-ene (693-89-0) → hydrido(η-methylcyclopentadienyl)bis(triphenylphosphine)iridium(III) hexafluoroantimonate (106864-47-5)

Conditions	Yield
In 1,2-dichloro-benzene refluxed for 6 h under inert atmosphere; cooled, evapd., residue recrystd. from CH2Cl2-Et2O;	85%

bis[bis(pentamethylcyclopentadienyl)(μ-hydride)yttrium] + 1-methylcyclopent-1-ene (693-89-0) → (C5(CH3)5)Y(η(3)-C5H6CH3) (500569-41-5)

Conditions	Yield
In further solvent(s) under inert atm. using Schlenk techniques; 1-methylcyclopentene added to((C5Me5)YH)2 dissolved in C6D11CD3 at -196°C; mixt. warmed to 0. degree.C; monitored by NMR (about 4 h);	85%

isocyanate de chlorosulfonyle (1189-71-5) + 1-methylcyclopent-1-ene (693-89-0) → cis-5-methyl-6-azabicyclo[3.2.0]heptan-7-one

Conditions	Yield
In diethyl ether for 8h; Cycloaddition; Heating;	84.7%

methanol (67-56-1) + 1-methylcyclopent-1-ene (693-89-0) → 7-Methoxy-7-methyl-1,2-dioxepan-3-ol (159335-79-2) + cis/trans-7-methoxy-3-methyl-1,2-dioxepane-3-ol + 1-hydroperoxy-1-methoxy-5-oxo-hexane (116972-39-5)

Conditions	Yield
With ozone at -78℃; Yields of byproduct given;	A 84% B n/a C n/a
With ozone at -78℃; Yield given. Title compound not separated from byproducts;	A 84% B n/a C n/a

Upstream product

• 1462-03-9 1-methylcyclopentanol 
• 859181-91-2 1-methyl-cyclopentanecarboxylic acid phenyl ester 
• 104-15-4 toluene-4-sulfonic acid 
• 110-83-8 cyclohexene 
• 108-93-0 cyclohexanol 
• 16240-42-9 1,2-epoxy-1-methylcyclopentane 
• 1165952-91-9 cyclohexa-1,3-diene 
• 592-41-6 1-hexene 
• 6196-85-6 1-chloro-1-methylcyclopentane 
• 7732-18-5 water 
• 96-37-7 methyl-cyclopentane 
• 71-43-2 benzene 
• 1165952-92-0 cyclohexa-1,4-diene 
• 30043-41-5 (hex-5-enyl)magnesium bromide 

Downstream Products

• 54850-17-8 4-Methyl-2-(1-methyl-cyclopentyl)-phenol 
• 1638-93-3 (+/-)-trans-2-methyl-cyclopentanethiol 
• 1638-94-4 (+/-)-cis-2-methyl-cyclopentanethiol 
• 16240-42-9 1,2-epoxy-1-methylcyclopentane 
• 1120-72-5 2-Methylcyclopentanone 
• 505-03-3 5-oxohexanal 
• 110-15-6 succinic acid 
• 96-37-7 methyl-cyclopentane 
• 1638-95-5 1-Methyl-cyclopentanthiol 
• 25144-04-1 trans-2-methylcyclopentanol 
• 3128-06-1 5-ketohexanoic acid 
• 65400-15-9 3a-methyl-3-phenyl-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole 
• 110434-51-0 cis-1-methyl-2-(phenylthio)cyclopentane 
• 1528-30-9 methylenecyclopentane 

Relevant articles and documents

Preparation of methylcyclopentane-1-d1

The title compound has been prepared in 70% yield by the reaction between 1-chloro-1-methylcyclopentane and deuterotributylstannane, without solvent. Small amounts (0.7-3.5%) of unreacted starting material remained after the reaction and were removed by solvolytic HCl elimination with water or aqueous sodium hydroxide, followed by oxidation with potassium permanganate or bromine addition at low temperature, which form products of low volatility. Small amounts of a by-product, deuterobutane, resulting from the cleavage of the carbon-tin bond in the reactant were also observed in the product.

METHOD FOR THE HYDRODEOXYGENATION OF OXYGENATED COMPOUNDS TO UNSATURATED PRODUCTS

The invention relates to methods of hydrodeoxygenation of oxygenated compounds into compounds with unsaturated carbon-carbon bonds, comprising the steps of: a) providing a reaction mixture comprising, an oxygenated compound containing one or more of a hydroxyl, keto or aldehyde group, an ionic liquid, a homogeneous metal catalyst, and carbon monoxide or a carbon monoxide releasing compound, b) reacting said reaction mixture under a H2 atmosphere at acidic conditions at a temperature between 180 and 250 °C and a pressure between 10 and 200 bar.

A method of preparing methyl pentene

Provided is a preparation method for methyl cyclopentene from methyl cyclopentadiene through continuous hydrogenation. The preparation method comprises steps: first, methyl cyclopentadiene, a solvent and hydrogen are mixed and subjected to a hydrogenation reaction through fixed bed catalyst bed layers continuously, the material weight ratio of methyl cyclopentadiene to the solvent is 1:(5-10), the mol ratio of methyl cyclopentadiene to hydrogen is 1: (2.0-4.0), and the catalyst employs Pd as an active component and has a content of 0.3-1.0wt%; second, the hydrogenation products are then subjected to removal of weight, removal of methyl cyclopentane and dehydrogenation to obtain methyl cyclopentene with a purity of being more than 99%, and the overall yield of methyl cyclopentene is more than 90%. The preparation method is advantageous in that the preparation method employs hydrogenation reaction by-product methyl cyclopentane as a reaction solvent, improves the separation and refining processes of methyl cyclopentene combined with hydrogenation product material composition, and ensures that the separation and refining processes of hydrogenation products are simplified and the yield of methyl cyclopentene is raised in the premise of good hydrogenation reaction effects.