US1010050A - Process of producing double olefins. - Google Patents
Process of producing double olefins. Download PDFInfo
- 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
Links
- 238000000034 method Methods 0.000 title description 13
- 150000001336 alkenes Chemical class 0.000 title description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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.
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)
| 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 |
-
1911
- 1911-01-21 US US60389211A patent/US1010050A/en not_active Expired - Lifetime
Cited By (1)
| 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 |
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