US1010050A - Process of producing double olefins. - Google Patents

Process of producing double olefins. Download PDF

Info

Publication number
US1010050A
US1010050A US60389211A US1911603892A US1010050A US 1010050 A US1010050 A US 1010050A US 60389211 A US60389211 A US 60389211A US 1911603892 A US1911603892 A US 1911603892A US 1010050 A US1010050 A US 1010050A
Authority
US
United States
Prior art keywords
olefins
producing double
producing
double
heating above
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 - Lifetime
Application number
US60389211A
Inventor
Fritz Hofmann
Ludwig Tank
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Farbenfabriken Vorm Friedr Bayer and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Farbenfabriken Vorm Friedr Bayer and Co filed Critical Farbenfabriken Vorm Friedr Bayer and Co
Priority to US60389211A priority Critical patent/US1010050A/en
Priority to US620428A priority patent/US1010405A/en
Application granted granted Critical
Publication of US1010050A publication Critical patent/US1010050A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/94—Opening of hydrocarbon ring

Definitions

  • double olefins like 10 erythrene and its homologues can readily be obtained by'heating above 500 C. cyclohexanols. Agents promoting the decomposition can be added. This process proceeds e. 9. according to the following equation:
  • Example 2 500 parts of ortho-methylcyclohexanol are converted intogas form in' a porcelain tube which is heated at 500- 40 600 C. and is filled with iron filings,a slight evolution of gas takes place.
  • the cooled receiver contains hydrocarbons from which isoprene can be isolated by distillation.
  • Example 3 On replacing in Example 1 Specification of Letters Patent.

Description

- -mvirnn STATES PATENT OFFTQ FEITZ HOFMATTN AND LUDWIG TANK, OF ELBERFELD, GERMANY, ASSIGNORS T FARBENFABRIKEN VORM. FRIEDR. BAYER 8: 10., OF ELBERFELD, GERMANY, A
CORPORATION OF GERMANY.
PROCESS OF PRODUCING DOUBLE OLEFINS.
' i No Drawing.
To all whom it may concern:
Be it known that we, Fnrrz HOFMANN and LUDWIG TAN a, doctors of philosophy, chemists,.citizcns of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvements in Processes for Producing Double Olefins, of which the following is a specification.
It has been found that double olefins, like 10 erythrene and its homologues can readily be obtained by'heating above 500 C. cyclohexanols. Agents promoting the decomposition can be added. This process proceeds e. 9. according to the following equation:
CH-OH place immediately with a lively evolution of gas. v Water, cyclohexen'e and cyclohexanone and also a' small quantity of unchanged cyclohexanol distil over. The gases are then fixed by bromin or are directly condensed.
' Erythrene. is .thusobtained with a' good yield.
Example 2: 500 parts of ortho-methylcyclohexanol are converted intogas form in' a porcelain tube which is heated at 500- 40 600 C. and is filled with iron filings,a slight evolution of gas takes place. The cooled receiver contains hydrocarbons from which isoprene can be isolated by distillation.
Example 3: On replacing in Example 1 Specification of Letters Patent.
Application filed January 21, 1911. Serial No. 603,892.
Patented Nov. 28, 1911.
the cyclohexanolby oxymethylcyclohexane' 5 of the formula: v
, on con OH: I on, on,
CH2 v the process takes place in an analogous manner. Isoprene is obtained with a good yield. In this case the iron tube is filled with native aluminium sesquioxid.
Instead of the cyclohexane derivatives mentioned in the above examples other of these compounds can be used. I
We claim 1. The process for producing olefins with two double bonds, which process consists in heating above 500 C. cyclohexanols, substantially as described. v
2. The process for producing olefins with two double bonds, which process consists in heating above 500 C. cycloheiganols with the addition of an agent promoting the decomposition, substantially as described.
3. The process for producing isoprene, which process consists in heating above 500 C. methylcyclohexanol, substantially as described.
4. The process for producing isoprene, 75 which process consists in heating above 500 C. ,methylcyclohexanol with the addition of aii-agent promoting the decomposition; substantiallyas described. In testimony whereof we have hereunto so set our-hands in the presence of two subscribingwitnesses.
'- FRITZ HOFMANN. [L. s.] LUDWIG TANK. [n.5,]
Witnesses:
j WALTER OONNEGUT, ALFRED HENKEL.
US60389211A 1911-01-21 1911-01-21 Process of producing double olefins. Expired - Lifetime US1010050A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US60389211A US1010050A (en) 1911-01-21 1911-01-21 Process of producing double olefins.
US620428A US1010405A (en) 1911-01-21 1911-04-11 Process of producing erythrene.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US60389211A US1010050A (en) 1911-01-21 1911-01-21 Process of producing double olefins.

Publications (1)

Publication Number Publication Date
US1010050A true US1010050A (en) 1911-11-28

Family

ID=3078360

Family Applications (1)

Application Number Title Priority Date Filing Date
US60389211A Expired - Lifetime US1010050A (en) 1911-01-21 1911-01-21 Process of producing double olefins.

Country Status (1)

Country Link
US (1) US1010050A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2542487A (en) * 1947-10-17 1951-02-20 Standard Oil Dev Co Production of olefins from oxides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2542487A (en) * 1947-10-17 1951-02-20 Standard Oil Dev Co Production of olefins from oxides

Similar Documents

Publication Publication Date Title
Simmons et al. A new synthesis of cyclopropanes1
La Rochelle et al. Preparation and chemistry of vinyl sulfonium ylides. New synthetic intermediates
Baldwin et al. Rearrangement of strained dipolar species. I. Episulfoxides. Demonstration of the existence of thiosulfoxylates
Kopecky et al. Preparation of dipivaloylmethane
US1841768A (en) Chlorinated and brominated ethine carbinols
Pickard et al. Ketimines. I. Alkyl-Aryl Type1
US3769330A (en) 2-butyl-1-alkynyl-cycloalkan-1-ols and derivatives thereof
US1010050A (en) Process of producing double olefins.
US2382085A (en) Synthesis of vitamin a
US2183574A (en) Preparation of unsaturated cyclic
Sasaki et al. Chrysanthemic acid. VIII. Syntheses of 1-vinyl-2-isobutenyl-and 1, 2-diisobutenyl-3, 3-dimethylcyclopropanes. Their thermal behavior in comparison with cis-2, 2-dimethyl-3-isobutenylcyclopropyl isocyanate and cis-2, 2-dimethyl-3-isobutenylcyclopropanecarboxaldehyde
US2727900A (en) New classes of cyclopropanes and processes of preparing them
FOSTER et al. Organomercury Chemistry. Decomposition of Alkenylmercury Compounds
US2766304A (en) Process for preparing azulenes
US2501200A (en) Process for production of menthane aldehyde
US3963782A (en) 5-Acetyl-1,2,6-trimethyltricyclo[5,3,2,02,7 ]dodeca-5-ene
US1094223A (en) Process for producing isoprene.
Johnson et al. Pyrolysis of alkyl sulfide tosylhydrazone salts. Search for R2S-4 participation in carbene reactions. Pyrolysis of sodium toluenesulfinate
Campbell et al. Allylic Rearrangements. XXIII. The Reaction of the Sodium Derivative of Allylbenzene with Carbonyl Compounds
US1308356A (en) of wilmington
US2531512A (en) Process for making sorbic acid esters
Kutney et al. The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues
US1102655A (en) Producing iso-olefins.
Gates et al. Dehydration of 5-hydroxytetrahydro-exo-dicyclopentadiene with acid
Shackelford et al. Synthesis of 1, 3, 5-Hexatriene