GB928932A - Production of isoprene - Google Patents
Production of isopreneInfo
- Publication number
- GB928932A GB928932A GB33348/59A GB3334859A GB928932A GB 928932 A GB928932 A GB 928932A GB 33348/59 A GB33348/59 A GB 33348/59A GB 3334859 A GB3334859 A GB 3334859A GB 928932 A GB928932 A GB 928932A
- Authority
- GB
- United Kingdom
- Prior art keywords
- neohexene
- butyl
- neohexane
- isomerization
- atmospheres
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title abstract 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 abstract 4
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 abstract 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical group CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract 2
- 238000006317 isomerization reaction Methods 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 abstract 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical class CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 239000001282 iso-butane Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical class CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 abstract 1
- 238000000197 pyrolysis Methods 0.000 abstract 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910010271 silicon carbide Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/173—Alkadienes with five carbon atoms
- C07C11/18—Isoprene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
- C07C4/04—Thermal processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/10—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from acyclic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3332—Catalytic processes with metal oxides or metal sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3335—Catalytic processes with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3335—Catalytic processes with metals
- C07C5/3337—Catalytic processes with metals of the platinum group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Isoprene is obtained by cracking neohexene. The reaction is effected at 650 DEG -900 DEG C. and 0,1-10 atmospheres for 0,01-1 second, preferably in the presence of silicon carbide. Unconverted neohexene is recycled. Neohexene may be obtained by dehydrogenating neohexane over an acid-free catalyst, e.g. platinum on chromia on alumina, at 450 DEG -900 DEG C. and 0,1-10 atmospheres for 0,2-100 seconds. Alternatively neohexene is obtained by isomerizing dimethylbutenes, by the dehydration of methyl tert. butyl carbinol or the pyrolysis of the tertiary hexanol obtained from hydrolysing the reaction product from tert. butyl, butyl chloride and ethylene over aluminium chloride or ferric chloride. Neohexane is obtained from C6 petroleum feeds preferably with isomerization of the residue, or by the isomerization of hydrogenated propylene dimer or by reacting isobutane and ethylene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US764876A US3115531A (en) | 1958-10-02 | 1958-10-02 | Cracking of neohexene to isoprene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB928932A true GB928932A (en) | 1963-06-19 |
Family
ID=25072043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33348/59A Expired GB928932A (en) | 1958-10-02 | 1959-10-01 | Production of isoprene |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3115531A (en) |
| CH (1) | CH387614A (en) |
| ES (1) | ES252357A1 (en) |
| GB (1) | GB928932A (en) |
| NL (1) | NL6700037A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3209048A (en) * | 1961-01-11 | 1965-09-28 | Sinclair Research Inc | Production of isoprene |
| US3274287A (en) * | 1964-04-21 | 1966-09-20 | Monsanto Co | Hydrocarbon conversion process and catalyst |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2162011A (en) * | 1934-12-27 | 1939-06-13 | Melle Usines Sa | Dehydrogenation of saturated hydrocarbons |
| US2217252A (en) * | 1937-08-14 | 1940-10-08 | Shell Dev | Process for isomerization of olefin hydrocarbons |
| US2184235A (en) * | 1937-12-06 | 1939-12-19 | Shell Dev | Catalytic dehydrogenation of organic compounds |
| US2339560A (en) * | 1941-05-27 | 1944-01-18 | Shell Dev | Production of dienes |
| US2391158A (en) * | 1942-02-16 | 1945-12-18 | Phillips Petroleum Co | Manufacture of diolefins |
| US2396416A (en) * | 1942-02-16 | 1946-03-12 | Phillips Petroleum Co | Diolefin preparation |
| US2406688A (en) * | 1942-12-03 | 1946-08-27 | Socony Vacuum Oil Co Inc | Process for producing olefinic hydrocarbons |
| US2417872A (en) * | 1942-12-19 | 1947-03-25 | Standard Oil Dev Co | Process for preparing a dimethyl butene from propylene |
| US2438315A (en) * | 1944-01-03 | 1948-03-23 | Phillips Petroleum Co | Dehydrogenation of 2, 3-dimethyl-butane |
| US2404056A (en) * | 1944-10-12 | 1946-07-16 | Socony Vacuum Oil Co Inc | Manufacture of isoprene |
| US2900429A (en) * | 1957-04-05 | 1959-08-18 | Houdry Process Corp | Preparation of isoprene |
-
1958
- 1958-10-02 US US764876A patent/US3115531A/en not_active Expired - Lifetime
-
1959
- 1959-09-29 ES ES0252357A patent/ES252357A1/en not_active Expired
- 1959-10-01 CH CH7891559A patent/CH387614A/en unknown
- 1959-10-01 GB GB33348/59A patent/GB928932A/en not_active Expired
-
1967
- 1967-01-03 NL NL6700037A patent/NL6700037A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3115531A (en) | 1963-12-24 |
| NL6700037A (en) | 1967-03-28 |
| CH387614A (en) | 1965-02-15 |
| ES252357A1 (en) | 1960-01-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB928932A (en) | Production of isoprene | |
| GB1122056A (en) | A process for isomerizing terminal olefins | |
| GB1016016A (en) | Process for the manufacture of hexafluoropropene | |
| GB993035A (en) | Production of 2-methyl-2-pentene and catalyst therefor | |
| GB1028572A (en) | Improvements relating to chlorine-containing catalysts | |
| GB1178735A (en) | Catalytic Conversion of Tetralin, Indan and other Materials | |
| GB921254A (en) | Improvements in and relating to fluorination | |
| GB1122702A (en) | Hydrogenolysis process | |
| US2671120A (en) | Noncatalytic isomerization of aromatic compounds | |
| GB571736A (en) | Dehydrogenation of butenes to butadiene | |
| GB966785A (en) | Isomerisation process | |
| US2438315A (en) | Dehydrogenation of 2, 3-dimethyl-butane | |
| GB1008964A (en) | Isomerisation of olefins | |
| GB1315067A (en) | Process for converting ethylene to normal alpha olefins | |
| GB831249A (en) | Improvements in or relating to the production of isoprene and other olefines | |
| US3388183A (en) | Olefin pyrolysis process promoted with mixtures of bromine and aromatic hydrocarbons | |
| GB1049422A (en) | Olefin disproportionation and dehydrogenation | |
| GB807603A (en) | A process for the preparation of mono-vinylaryl hydrocarbons | |
| US2431763A (en) | Manufacture of polycyclic hydrocarbons | |
| GB829611A (en) | Preparation of isoprene | |
| NL7105545A (en) | High porosity dehydrogenation catalyst | |
| GB675836A (en) | A process for the isomerisation of xylenes and the resulting xylenes | |
| GB992115A (en) | Dehydrogenation process | |
| KR930000442A (en) | Process for isomerizing linear olefins to isoolefins | |
| GB1006049A (en) | Conversion of olefins |