US3115531A - Cracking of neohexene to isoprene - Google Patents

Cracking of neohexene to isoprene Download PDF

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US3115531A
US3115531A US764876A US76487658A US3115531A US 3115531 A US3115531 A US 3115531A US 764876 A US764876 A US 764876A US 76487658 A US76487658 A US 76487658A US 3115531 A US3115531 A US 3115531A
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neohexane
isoprene
neohexene
line
cracking
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US764876A
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Colton John White
Rex E Lidov
Gerson S Schaffel
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Halcon Research and Development Corp
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Halcon International Inc
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Priority to ES0252357A priority patent/ES252357A1/en
Priority to CH7891559A priority patent/CH387614A/en
Priority to GB33348/59A priority patent/GB928932A/en
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Assigned to HALCON RESEARCH AND DEVELOPMENT CORPORATION reassignment HALCON RESEARCH AND DEVELOPMENT CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HALCON INTERNATIONAL, INC.
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    • 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

Definitions

  • This invention is concerned with the production of isoprene. More particularly, this invention is concerned with the production of isoprene from neohexane and its derivatives. More specifically, this invention is concerned with processes for the production of isoprene from neohexane comprising the steps of dehydrogenating neohexane to produce neohexene and demethylating said neohexene to yield isoprene.
  • isoprene may be prepared from aliphatic hydrocarbons in a variety of methods embracing several combinations of steps. Many of these methods require large quantities of unavailable materials and produce relatively low overall yields, thereby rendering such processes uneconomical.
  • Another difficulty encountered in the art is the large heat energy requirement in processes for the production of isoprene, particularly where the steps of dehydrogenation, cracking and distillation are necessary to obtain the desired product.
  • paraffin streams such as that produced by isomerization of light naphtha
  • Another feature of this invention is to provide a process for the production of isoprene which using neohexane as the principal feedstock, makes possible ready recovery and recycle of those portions of the feedstock which do not undergo conversion in the first stages of the process.
  • a preferred embodiment of the invention comprises, in a process for producing isoprene, the steps of dehydrogenating neohexane to form a mixture of neohexane and neohexene, separating said neohexane from said neohexene, recycling said neohexane to the dehydrogenating step, cracking said neohexene to produce a 3,115,531 Patented Dec. 24-, 1963 mixture of isoprene and other hydrocarbons, separating isoprene and said other hydrocarbons and using said hydrocarbons as a source of heat energy for the process.
  • Still another preferred embodiment comprises the steps of separating neohexane and other C hydrocarbons from a C hydrocarbon fraction, isomerizing the said separated C hydrocarbons, recycling the isomerizate to the separation step, dehydrogenating said separated neohexane to form a mixture of neohexane and neohexene, separating neohexane from said neohexene, recycling said separated neohexane to the dehydrogenating step, cracking said neohexene to produce a mixture of isoprene and other hydrocarbons, separating isoprene and said other hydrocarbons and using said hydrocarbons as a source of heat energy for the process.
  • Another preferred embodiment comprises the steps of producing neohexane from precursors of neohexane, separating said neohexane from said precursors, recycling said separated precursors to the neohexane preparation step, dehydrogenating said neohexane to form a mixture of neohexane and neohexene, separating neohexane from said neohexene and cracking said neohexene to produce a mixture of isoprene and other hydrocarbons and recovering isoprene.
  • FIGURE 1 is a schematic illustration of an embodi ment of the invention, in which isoprene is produced from gasoline.
  • FIGURE 2 is a schematic illustration of an embodiment of the invention, in which neohexane is produced from a C hydrocarbon stream.
  • FIGURE 3 is a schematic illustration of an embodiment of the invention, in which neohexane is produced from a precursor, propylene, by dimerization and hydrogenation.
  • gasoline is fed through line 10 into separator 12 and neohexane is removed as distillate through line 13.
  • the residue is withdrawn through line 11.
  • the distillate from line 13 is fed into dehydrogenator 15 and the products of the dehydrogenation are led through line 16 into separator 18.
  • Neohexene is removed from the separator and fed through line 19 into cracker 2h.
  • the unreacted neohexane is removed overhead from separator 18 and recycled through line 21 to dehydrogenator 15.
  • the neohexene is cracked in cracker 20 to form isoprene, and other hydrocarbons, such as methane and ethane.
  • This mixture is fed through line 22 into separator 23 where isoprene product is removed through line 27, the uncracked neohexene product is recycled through line 25 to cracker 2t) and the other hydrocarbons are removed through line 24 to be used as fuel in the process; for example, cracker 20, dehydrogenator 15, or wherever else fuel is required in the process.
  • a C paraffin stream is fed through line 39 into separator 31.
  • Neohexane is removed through line 35 and other C hydrocarbons which are separated from the stream are led through line 32 into isomerization unit 33.
  • the C hydrocarbons are isomerized and the isomerizate is recycled to separator 31 through line 34.
  • the neohexane, which is contained in the isomerizate is removed through line 35 to dehydrogenator 15 and the dehydrogenation and cracking steps are carried out as described in FIGURE 1.
  • propylene is fed through line 40 into dimerizer 41. After dimerization the products are led through line 42 into separator 46. Unreacted propylene is recycled to the dimerizer through line 44. The heavier products are removed through line 45.
  • the C olefins containing neohexene are fed through line 47 to hydrogenator 48 where they are hydrogenated and passed through line 49 into isomerizer 50.
  • the isomerization products are fed through line 57 into separator 52 and the neohexane is wremoved through line 54 to dehydrogenator and the dehydrogenation and cracking steps are carried out as described in FIGURE 1.
  • the remaining C paraffins are recycled through line 53 to the isomerizer 50.
  • Neohexane may also be produced by isome'rizing C parafiinic hydrocarbons over an aluminum chloride catalyst in the presence of HCl.
  • the isomerization is usually carried out at a temperature of about 100 C. in the presence of hydrogen at a pressure of 1000 p.s.i.g.
  • the hydrogen is employed to inhibit disproportionation and cracking.
  • Naphthenes or benzene may be used instead of hydrogen to inhibit cracking.
  • Other catalysts such as metallic oxides, for example, nickel or cobalt on silica alumina, may be utilized for isomerization at pressures of about atmospheres in the presence of hydrogen. Such reactions may be carried out at temperatures in the range of about 300-450" C.
  • Neohexane Another method of producing neohexene which may be employed is the isomerization of dimethyl butenes to neohexene.
  • Neohexane may also be produced by reacting iso-butane and ethylene.
  • neohexene is produced by reacting tertiary butyl chloride with ethylene over an aluminum chloride or ferric chloride catalyst, hydrolyzing the resulting product to the corresponding tertiary hexanol and pyrolyzing the hexanol to produce neohexene.
  • neohexene is produced directly from methyl ter-butyl carbinol by dehydration and then cracked to isoprene.
  • Example I A neohexane sample is passed over a platinum alumina catalyst at a temperature of about 600 C. at a contact time of about 2.8 seconds.
  • the product condensate is separated into neohexene, which boils at 41.2" C. and all other constituents, including mostly unreacted neohexane but some other olefins and paraffin isomers. These may be saturated with hydrogen in a separate catalytic step and recycled to the isomerizer.
  • the resulting neohexene is diluted with nitrogen at 'a nitrogen to neohexene mol ratio of 7.611 and is fed into a reactor tube having a ratio of length to diameter of about 50:1 which is packed with silicon carbide granules for approximately one-half of its length at the discharge end, at a rate of 10.7 volumes of liquid per hour per volume of reactor.
  • the cracking is carried out at a temperature of about 800 C. and there is obtained a conversion of 77.5% and a selectivity to isoprene of 4
  • Example 2 Example 1 is repeated using a chrome alumina catalyst instead of a platinum alumina catalyst. Substantially similar results are obtained.
  • the dehydrogenation step is carried out in an acidfree catalyst system at a temperature of broadly 450 to 900 C., preferably 500 to 650 C. and desirably 575 to 625 C.
  • the pressure is broadly 0.1 to 10 atmospheres, preferably 0.5 to 1.5 atmospheres and desirably close to atmospheric.
  • the contact time is broadly 0.2 to seconds, preferably 0.5 to 20 seconds, and desirably 0.8 to 10 seconds. Temperature and contact time are interdependent with short contact times preferred for high temperatures and vice versa.
  • the catalyst is platinum alumina, chromia alumina or any other suitable acid-free dehydrogenation catalyst with which undesirable structural isomerization is prevented.
  • the cracking step is carried out at a temperature of broadly 650 to 900 C., preferably 700 to 850 C. and desirably 760 to 800 C.
  • the contact time for cracking may be broadly 0.01 to 1.0 second.
  • Packing such as silicon carbide granules or any other equivalent material may be employed.
  • the diluent may be steam or nitrogen or other inert gas. Steam is preferred in commercial operations, although nitrogen is used for convenience in many laboratory experiments.
  • the pressure is broadly 0.1 to 10 atmospheres, preferably 0.5 to 1.5 and desirably close to atmospheric.
  • a process for the production of isoprene the step of cracking a feedstock concentrated in neohexene at a temperature in the range of from about 650 to 900 C. and a pressure in the range of about 0.1 to 10 atmospheres, at a contact time of about 0.01 to 1.0 second to produce a mixture of isoprene and other hydrocarbons and recovering said isoprene.

Description

Dec. 24, 1963 J. w. COLTON ETAL 3,115,531
CRACKING OF NEOHEXENE TO ISOPRENE Filed Oct. 2, 195a HYDROCARBONS TO USE AS FUEL IN m; PROCESS- r- GASOLINE FRACTION ISOPRENE -2 ,/a r2/ ,20 I 3 I /e SEPARATOR osuvonm SEPARATOR. omcxsn. SEPARATOR SENATOR 112 NEOHEXANE' TO DEHYDROGENATOR. I5 32 a HYDROCARBON SEPARATOR ISOMERJZER PARAFFINS 30 L? 52 rezonzxm: TO [44 DEHYDROGENATOR. I5
47 HYDRO GENATOR. 54 [4/ 46 49: 8 1 SEPARATOR I [so 1:..E PROPYLENE SEPAR- 40 DIMERIZER OR F IZER Kw INVENTORS 42 4 57 JOHN WHITE COLTON- 1 REXEL/DOV GERSON S. SCH/1F United States Patent 3,115,531 CRACKING 0F NEOHEXENE T0 ISOPRENE John White Colton, Pelham Manor, Rex E. Lidov, Great Neck, and Gerson S. Schaifel, Old Westbury, N.Y.,
assignors to Halcon International, Inc., a corporation of Delaware Filed (let. 2, 1958, Ser. No. 764,876 1 Claim. ((31. 260-680) This invention is concerned with the production of isoprene. More particularly, this invention is concerned with the production of isoprene from neohexane and its derivatives. More specifically, this invention is concerned with processes for the production of isoprene from neohexane comprising the steps of dehydrogenating neohexane to produce neohexene and demethylating said neohexene to yield isoprene.
It is known in the art that isoprene may be prepared from aliphatic hydrocarbons in a variety of methods embracing several combinations of steps. Many of these methods require large quantities of unavailable materials and produce relatively low overall yields, thereby rendering such processes uneconomical.
Another difficulty encountered in the art is the large heat energy requirement in processes for the production of isoprene, particularly where the steps of dehydrogenation, cracking and distillation are necessary to obtain the desired product.
It is a feature of the present invention to produce isoprene from materials available in abundant supply, such as from C hydrocarbon fractions which may be readily separated to yield precursors of isoprene.
It is another feature of the present invention to utilize paraffin streams, such as that produced by isomerization of light naphtha, as a source of neohexane. Mixtures of isomeric parafiins, from which neohexane may be obtained by distillation, are frequently produced for the manufacture of high octane gasoline, and are available at low cost and in abundant supply, so that gasoline may be utilized as a starting material for the production of isoprene, thereby providing an economical method for producing isoprene.
It is another feature of the invention to utilize the hydrocarbons which are formed as by-product in the production of isoprene, as a source of heat energy for the process, thereby providing an economical method for obtaining fuel and minimizing power and utility costs for such processes.
It will be realized that another feature of this invention is to provide a process for the production of isoprene which using neohexane as the principal feedstock, makes possible ready recovery and recycle of those portions of the feedstock which do not undergo conversion in the first stages of the process.
It is still another feature of the present invention to produce isoprene in good yields from neohexane, taking advantage of the unique structure of neohexane, which forms only one olefin, neohexene, upon dehydrogenation.
It is another feature of this invention to provide a novel method by which neohexane may be dehydro genated to produce neohexene which, upon cracking, yields isoprene.
It is a further feature of this invention to provide a novel method by which neohexene may be thermally cracked to produce isoprene.
A preferred embodiment of the invention comprises, in a process for producing isoprene, the steps of dehydrogenating neohexane to form a mixture of neohexane and neohexene, separating said neohexane from said neohexene, recycling said neohexane to the dehydrogenating step, cracking said neohexene to produce a 3,115,531 Patented Dec. 24-, 1963 mixture of isoprene and other hydrocarbons, separating isoprene and said other hydrocarbons and using said hydrocarbons as a source of heat energy for the process.
Still another preferred embodiment comprises the steps of separating neohexane and other C hydrocarbons from a C hydrocarbon fraction, isomerizing the said separated C hydrocarbons, recycling the isomerizate to the separation step, dehydrogenating said separated neohexane to form a mixture of neohexane and neohexene, separating neohexane from said neohexene, recycling said separated neohexane to the dehydrogenating step, cracking said neohexene to produce a mixture of isoprene and other hydrocarbons, separating isoprene and said other hydrocarbons and using said hydrocarbons as a source of heat energy for the process.
Another preferred embodiment comprises the steps of producing neohexane from precursors of neohexane, separating said neohexane from said precursors, recycling said separated precursors to the neohexane preparation step, dehydrogenating said neohexane to form a mixture of neohexane and neohexene, separating neohexane from said neohexene and cracking said neohexene to produce a mixture of isoprene and other hydrocarbons and recovering isoprene.
Other objectives of this invention will become apparent from the description thereof which follows:
FIGURE 1 is a schematic illustration of an embodi ment of the invention, in which isoprene is produced from gasoline.
FIGURE 2 is a schematic illustration of an embodiment of the invention, in which neohexane is produced from a C hydrocarbon stream.
FIGURE 3 is a schematic illustration of an embodiment of the invention, in which neohexane is produced from a precursor, propylene, by dimerization and hydrogenation.
Referring to FIGURE 1, gasoline is fed through line 10 into separator 12 and neohexane is removed as distillate through line 13. The residue is withdrawn through line 11. The distillate from line 13 is fed into dehydrogenator 15 and the products of the dehydrogenation are led through line 16 into separator 18. Neohexene is removed from the separator and fed through line 19 into cracker 2h. The unreacted neohexane is removed overhead from separator 18 and recycled through line 21 to dehydrogenator 15. The neohexene is cracked in cracker 20 to form isoprene, and other hydrocarbons, such as methane and ethane. This mixture is fed through line 22 into separator 23 where isoprene product is removed through line 27, the uncracked neohexene product is recycled through line 25 to cracker 2t) and the other hydrocarbons are removed through line 24 to be used as fuel in the process; for example, cracker 20, dehydrogenator 15, or wherever else fuel is required in the process.
Referring to FIGURE 2, a C paraffin stream is fed through line 39 into separator 31. Neohexane is removed through line 35 and other C hydrocarbons which are separated from the stream are led through line 32 into isomerization unit 33. The C hydrocarbons are isomerized and the isomerizate is recycled to separator 31 through line 34. The neohexane, which is contained in the isomerizate is removed through line 35 to dehydrogenator 15 and the dehydrogenation and cracking steps are carried out as described in FIGURE 1.
Referring to FIGURE 3, propylene is fed through line 40 into dimerizer 41. After dimerization the products are led through line 42 into separator 46. Unreacted propylene is recycled to the dimerizer through line 44. The heavier products are removed through line 45. The C olefins containing neohexene are fed through line 47 to hydrogenator 48 where they are hydrogenated and passed through line 49 into isomerizer 50. The isomerization products are fed through line 57 into separator 52 and the neohexane is wremoved through line 54 to dehydrogenator and the dehydrogenation and cracking steps are carried out as described in FIGURE 1. The remaining C paraffins are recycled through line 53 to the isomerizer 50.
Neohexane may also be produced by isome'rizing C parafiinic hydrocarbons over an aluminum chloride catalyst in the presence of HCl. The isomerization is usually carried out at a temperature of about 100 C. in the presence of hydrogen at a pressure of 1000 p.s.i.g. The hydrogen is employed to inhibit disproportionation and cracking. Naphthenes or benzene may be used instead of hydrogen to inhibit cracking. Other catalysts, such as metallic oxides, for example, nickel or cobalt on silica alumina, may be utilized for isomerization at pressures of about atmospheres in the presence of hydrogen. Such reactions may be carried out at temperatures in the range of about 300-450" C.
Another method of producing neohexene which may be employed is the isomerization of dimethyl butenes to neohexene. Neohexane may also be produced by reacting iso-butane and ethylene.
In still another method, neohexene is produced by reacting tertiary butyl chloride with ethylene over an aluminum chloride or ferric chloride catalyst, hydrolyzing the resulting product to the corresponding tertiary hexanol and pyrolyzing the hexanol to produce neohexene.
In another embodiment of the invention, neohexene is produced directly from methyl ter-butyl carbinol by dehydration and then cracked to isoprene.
Other methods of producing isoprene from neohexane precursors utilizing the teaching of the present invention will become apparent as a result of these disclosures and it is intended that the invention embrace the formation of neohexane from other such precursors, that is, substances which precede formation of neohexane.
The invention is illustrated by but not restricted to the following embodiments.
As used herein parts and percentages are by weight, unless otherwise specified.
Example I A neohexane sample is passed over a platinum alumina catalyst at a temperature of about 600 C. at a contact time of about 2.8 seconds.
The product condensate is separated into neohexene, which boils at 41.2" C. and all other constituents, including mostly unreacted neohexane but some other olefins and paraffin isomers. These may be saturated with hydrogen in a separate catalytic step and recycled to the isomerizer.
The resulting neohexene is diluted with nitrogen at 'a nitrogen to neohexene mol ratio of 7.611 and is fed into a reactor tube having a ratio of length to diameter of about 50:1 which is packed with silicon carbide granules for approximately one-half of its length at the discharge end, at a rate of 10.7 volumes of liquid per hour per volume of reactor. The cracking is carried out at a temperature of about 800 C. and there is obtained a conversion of 77.5% and a selectivity to isoprene of 4 Example 2 Example 1 is repeated using a chrome alumina catalyst instead of a platinum alumina catalyst. Substantially similar results are obtained.
The dehydrogenation step is carried out in an acidfree catalyst system at a temperature of broadly 450 to 900 C., preferably 500 to 650 C. and desirably 575 to 625 C. The pressure is broadly 0.1 to 10 atmospheres, preferably 0.5 to 1.5 atmospheres and desirably close to atmospheric. The contact time is broadly 0.2 to seconds, preferably 0.5 to 20 seconds, and desirably 0.8 to 10 seconds. Temperature and contact time are interdependent with short contact times preferred for high temperatures and vice versa. The catalyst is platinum alumina, chromia alumina or any other suitable acid-free dehydrogenation catalyst with which undesirable structural isomerization is prevented.
The cracking step is carried out at a temperature of broadly 650 to 900 C., preferably 700 to 850 C. and desirably 760 to 800 C. The contact time for cracking may be broadly 0.01 to 1.0 second. Packing such as silicon carbide granules or any other equivalent material may be employed. The diluent may be steam or nitrogen or other inert gas. Steam is preferred in commercial operations, although nitrogen is used for convenience in many laboratory experiments. The pressure is broadly 0.1 to 10 atmospheres, preferably 0.5 to 1.5 and desirably close to atmospheric.
In view of the foregoing disclosures, variations and modifications thereof will be apparent to anyone skilled in the art, and it is intended to include within the invention all such variations and modifications except as do not come within the scope of the appended claim.
What is claimed is:
In a process for the production of isoprene, the step of cracking a feedstock concentrated in neohexene at a temperature in the range of from about 650 to 900 C. and a pressure in the range of about 0.1 to 10 atmospheres, at a contact time of about 0.01 to 1.0 second to produce a mixture of isoprene and other hydrocarbons and recovering said isoprene.
References Cited in the file of this patent UNITED STATES PATENTS 2,162,011 Guinot June 13, 1939 2,184,235 Groll et al Dec. 19, 1939 2,217,252 Hoog Oct. 8, 1940 2,339,560 De Simo et al. Jan. 18, 1944 2,391,158 Hepp Dec. 18, 1945 2,396,416 Frey Mar. 12, 1946 2,404,056 Gorin et al. July 16, 1946 2,406,688 Horton Aug. 27, 1946 2,417,872 Hill et al. Mar. 25, 1947 2,438,315 Frey Mar. 23, 1948 2,900,429 Heinemann et al. Aug. 18, 1959 OTHER REFERENCES vol.
US764876A 1958-10-02 1958-10-02 Cracking of neohexene to isoprene Expired - Lifetime US3115531A (en)

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US764876A US3115531A (en) 1958-10-02 1958-10-02 Cracking of neohexene to isoprene
ES0252357A ES252357A1 (en) 1958-10-02 1959-09-29 Cracking of neohexene to isoprene
CH7891559A CH387614A (en) 1958-10-02 1959-10-01 Isoprene preparation process
GB33348/59A GB928932A (en) 1958-10-02 1959-10-01 Production of isoprene
NL6700037A NL6700037A (en) 1958-10-02 1967-01-03

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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

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US2184235A (en) * 1937-12-06 1939-12-19 Shell Dev Catalytic dehydrogenation of organic compounds
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US2396416A (en) * 1942-02-16 1946-03-12 Phillips Petroleum Co Diolefin preparation
US2404056A (en) * 1944-10-12 1946-07-16 Socony Vacuum Oil Co Inc Manufacture of isoprene
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
US2900429A (en) * 1957-04-05 1959-08-18 Houdry Process Corp Preparation of isoprene

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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
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US2404056A (en) * 1944-10-12 1946-07-16 Socony Vacuum Oil Co Inc Manufacture of isoprene
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Cited By (2)

* Cited by examiner, † Cited by third party
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

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Publication number Publication date
CH387614A (en) 1965-02-15
ES252357A1 (en) 1960-01-01
GB928932A (en) 1963-06-19
NL6700037A (en) 1967-03-28

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