US2366126A - Production of cycloolefinic hydrocarbons and aromatic hydrocarbons - Google Patents
Production of cycloolefinic hydrocarbons and aromatic hydrocarbons Download PDFInfo
- Publication number
- US2366126A US2366126A US540008A US54000844A US2366126A US 2366126 A US2366126 A US 2366126A US 540008 A US540008 A US 540008A US 54000844 A US54000844 A US 54000844A US 2366126 A US2366126 A US 2366126A
- Authority
- US
- United States
- Prior art keywords
- hydrocarbons
- hydrocarbon
- carbon atoms
- production
- cycloolefinic
- 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
- 229930195733 hydrocarbon Natural products 0.000 title description 26
- 150000002430 hydrocarbons Chemical class 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title 1
- 239000004215 Carbon black (E152) Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- -1 cyclohexene hydrocarbon Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- TXNWMICHNKMOBR-UHFFFAOYSA-N 1,2-dimethylcyclohexene Chemical compound CC1=C(C)CCCC1 TXNWMICHNKMOBR-UHFFFAOYSA-N 0.000 description 1
- PKHOIUJRGGWFEF-UHFFFAOYSA-N 1,3,5-trimethylcyclohexene Chemical compound CC1CC(C)C=C(C)C1 PKHOIUJRGGWFEF-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
' ing cyclic hydrocarbons.
Patented Dec. 26, 1944 raonoc'non or CYCLOOLEFINIC HYDRO- CARBONS AND BONS AROMATIC HYDROCAB- Herman Pines and Vladimir N. Ipatiefl', Riverside,-Ill., assignors to Universal Oil. Products Company, Chicago, Ill.,a. corporation of Dela.-
ware
No Drawing. Application June 12, 1944,
Serial No. 540,008
8 Claims.
This invention relates to a process for produc- More specifically, the invention relates to a process for producing cycloolefins by condensing a glycol of at least 4 carbon atoms with an olefin.
An object of this invention is the condensation of an oleflnic hydrocarbon with a glycol containing at least 4 carbon atoms per molecule.
Another object of this invention is the production of a cyclohexene hydrocarbon by condensing a mono-olefinic'hydrocarbon with a gly-. col containing at least 4 carbon atoms per mole cule. I
A further object of this invention is the production of 1,3,5-trimethylcyclohexene by condensing 2-methylpentanediol-2,4 with propylene.
One specific embodiment of this invention relates to a process for producing a cyclo-olefin which comprises condensing an aliphatic monoolefin with a glycol having at least 4 carbon atoms per molecule at a temperature of from about 150 to about 400 C.
A further embodiment of this invention relates to a process which comprises condensing a mono-olefin with a cyclic glycol having at least 4 carbon atoms per molecule.
Cyclohexene and different alkyl cyclohexene hydrocarbons which are obtainable by the process of our invention may be hydrogenated to cyclohexane hydrocarbons, or be dehydrogenated to benzene and alkylated benzene hydrocarbons.
By the term condensation used in this specification and in the claims, we mean the chemical combination of a glycol of at least 4 carbon atoms with an olefin accompanied by the splitting out character of results obtained by the process of iii our invention, although the data presented are not introduced with the intention of unduly restricting the broad scope of the invention.
Ethylene, under an initial pressure of 40 atmospheres at 25 C. was introduced to a'steel autoclave of 450 cc. capacity containing 58.4 grams of 2-methylpentanediol-2,4 and heated at 200 C. The product formed in this reaction was found to consist of 40 grams of normally liquid hydrocarbons and 35 cc. (approximately 22 grams) of liquefied condensible gases. About 25 of the normally liquid hydrocarbon product boiled between 124 and 135 C. and comprised essentially dimethylcyclohexene, which by hydrogenation and subsequent dehydrogenation over platinized alumina catalyst yielded meta-xylene. About of the liquefied condensible gas was isobutylene.
The novelty and utility of the process of the present invention are evident from the preceding specification and example, although neither section is intended to limit unduly the broad scope of our invention.
We claim as our invention:
1. A process for producing a cyclo-olefinic hydrocarbon which comprises reacting a glycol having at least 4 carbon atoms per molecule and an olefinic hydrocarbon at a sufficient temperature Olefinic alcohols or partially dehydrated glycols such as 2-methylpentene-1-ol-4, are also useful' raw materials for our condensation process.
The olefins usable in our process are prefer- 4 carbon atoms per molecule at a temperature oi from about 150 to about 400 C. and at a superatmospheric pressure of from about 10 to about 100 atmospheres.
4. A process for producing a cyclo olefinic hy" drocarbon which comprises reacting more than one molecular proportion of a mono-oleflnic hydrocarbon and one molecular proportion of a glycol having at least 4 carbon atoms per mole- 7. A process for producing a benzene hydrocarbon which comprises condensing a mono-oleflnic hydrocarbon and a glycol containing at least 4 carbon atoms per molecule to produce a cyclohexene hydrocarbon, hydrogenating said cyclohexene hydrocarbon to a cyclohexane hydrocarbon, dehydrogenating the latter hydrocarbon to a benzene hydrocarbon and hydrogen, and utilizing at least a portion of said hydrogen in the hydrogenation of the cyclohexene hydrocarbon.
8. A process'for producing a benzene hydrocarbon which comprises condensing a mono-oleflnic hydrocarbon and a glycol containing at least 4 carbon atoms per molecule to produce a cyclohexene hydrocarbon and dehydrogenating said cyclohexene hydrocarbon to a benezene hydrocarbon.
HERMAN PINES.
VLADIMIR N. IPATIEFF.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US540008A US2366126A (en) | 1944-06-12 | 1944-06-12 | Production of cycloolefinic hydrocarbons and aromatic hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US540008A US2366126A (en) | 1944-06-12 | 1944-06-12 | Production of cycloolefinic hydrocarbons and aromatic hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2366126A true US2366126A (en) | 1944-12-26 |
Family
ID=24153588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US540008A Expired - Lifetime US2366126A (en) | 1944-06-12 | 1944-06-12 | Production of cycloolefinic hydrocarbons and aromatic hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2366126A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2473472A (en) * | 1946-04-15 | 1949-06-14 | Socony Vacuum Oil Co Inc | Manufacture of cyclohexene |
| US2611736A (en) * | 1948-11-16 | 1952-09-23 | Universal Oil Prod Co | Reforming process and catalyst therefor |
-
1944
- 1944-06-12 US US540008A patent/US2366126A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2473472A (en) * | 1946-04-15 | 1949-06-14 | Socony Vacuum Oil Co Inc | Manufacture of cyclohexene |
| US2611736A (en) * | 1948-11-16 | 1952-09-23 | Universal Oil Prod Co | Reforming process and catalyst therefor |
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