US1065182A - Producing isoprene. - Google Patents
Producing isoprene. Download PDFInfo
- Publication number
- US1065182A US1065182A US64598211A US1911645982A US1065182A US 1065182 A US1065182 A US 1065182A US 64598211 A US64598211 A US 64598211A US 1911645982 A US1911645982 A US 1911645982A US 1065182 A US1065182 A US 1065182A
- Authority
- US
- United States
- Prior art keywords
- isoprene
- producing isoprene
- dipentene
- temperature
- wire
- 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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title description 18
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000003800 Staudinger reaction Methods 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 125000000396 limonene group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- Y10S585/947—Terpene manufacture or recovery
Definitions
- HERMANN' A. STAUDINGER, OF KARLSRUHE, GERMANY, ASSIGN'OR TO BADISCHE ANILIN & SODA FABRIK, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, A COR- PORATION.
- isoprene can be obtained in very good yield from dipentene by heating vaporized dipentene in a state of attenua-- tion, such attenuation being effected by the addition of indifferent gas, or gases, such for instance as nitrogen, or by reducing the pressure in any suitable manner.
- indifferent gas or gases, such for instance as nitrogen
- the vapor be not left too long in contact With the source of heat, but that it be removed as soon as possible from the zone of high temperature.
- a wire heated to redness by means of an electric current is a suitable means for obtaining the necessary temperature. When the vapors are only heated to a dull red heat, less gaseous product is obtained, but the decomposition of the dipentene proceeds slowly. If the temperature,
- dipentene employed for the purpose of my invention can beobtained from turpentine by chemical means, or it can be produced synthetically, or the forms of dipentene which occur in nature, such for instance as limonene, can be em ployed.
- the following example will serve to iJlusfrom 60 to 70 grams per hour, over a platinum wire 3 meters .in length and 0.5 millimeter in diameter, using a current of 400 volt-amperes.
- the temperature varies between 500 and 700 C.
- the rate at which the dipentine is passed over the Wire will vary according to the conditions employed, for instance it is dependent in particular on the diameter and the length of the wire.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES PATENT OFFICE.
HERMANN' A. STAUDINGER, OF KARLSRUHE, GERMANY, ASSIGN'OR TO BADISCHE ANILIN & SODA FABRIK, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, A COR- PORATION.
PRODUCING ISOPRENE.
1 065,182 Specification of Letters Patent.
No Drawing.
To all whom it may concern:
Be it known that I, HERMANN A. F. STAUD- INGER, subject of the Grand Duke of Baden, residing at 'Karlsruhe, Germany, have invented new and useful Improvements in Producing Isoprene, of which the following is a specification.
I have found that isoprene can be obtained in very good yield from dipentene by heating vaporized dipentene in a state of attenua-- tion, such attenuation being effected by the addition of indifferent gas, or gases, such for instance as nitrogen, or by reducing the pressure in any suitable manner. In order to obtain good yields it is desirable that the vapor be not left too long in contact With the source of heat, but that it be removed as soon as possible from the zone of high temperature. A wire heated to redness by means of an electric current is a suitable means for obtaining the necessary temperature. When the vapors are only heated to a dull red heat, less gaseous product is obtained, but the decomposition of the dipentene proceeds slowly. If the temperature,
however, be -raised considerably, a good yield of isoprene is obtained more quickly, but
the quantity of gaseous by-product is also slightly increased. The dipentene employed for the purpose of my invention can beobtained from turpentine by chemical means, or it can be produced synthetically, or the forms of dipentene which occur in nature, such for instance as limonene, can be em ployed.
Application filed August 25, 1911.
Serial No. 645,982.
Patented June 17, 1913.
The following example will serve to iJlusfrom 60 to 70 grams per hour, over a platinum wire 3 meters .in length and 0.5 millimeter in diameter, using a current of 400 volt-amperes. The temperature varies between 500 and 700 C. Pass the gases through a vessel cooled with solid carbon dioxid and isolate the isoprene by fractional distillation of the liquid obtained. The rate at which the dipentine is passed over the Wire will vary according to the conditions employed, for instance it is dependent in particular on the diameter and the length of the wire.
According to this invention yields of fifty per cent. or more of isoprene can be obtained.
Now what I claim is 1. The process of producing isoprene by heating vaporized dipentene in a state of attenuation at a temperature above 350 C.
2. The process of producing isoprene by heating vaporized dipentene under reduced pressure at a temperature above 350 C.
In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.
HERMANN A. F. STAUDINGER.
Witnesses:
" J. Auto. LLOYD,
' JOSEPH Fnrrrnn.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64598211A US1065182A (en) | 1911-08-25 | 1911-08-25 | Producing isoprene. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64598211A US1065182A (en) | 1911-08-25 | 1911-08-25 | Producing isoprene. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1065182A true US1065182A (en) | 1913-06-17 |
Family
ID=3133425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US64598211A Expired - Lifetime US1065182A (en) | 1911-08-25 | 1911-08-25 | Producing isoprene. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1065182A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423179A (en) * | 1942-09-07 | 1947-07-01 | Union Oil Co | Recovery of dienes by polymerization and depolymerization |
| US2508922A (en) * | 1948-05-17 | 1950-05-23 | Shell Dev | Separation of dienes |
| US2543005A (en) * | 1947-03-18 | 1951-02-27 | Socony Vacuum Oil Co Inc | Method for conducting hightemperature conversions |
-
1911
- 1911-08-25 US US64598211A patent/US1065182A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423179A (en) * | 1942-09-07 | 1947-07-01 | Union Oil Co | Recovery of dienes by polymerization and depolymerization |
| US2543005A (en) * | 1947-03-18 | 1951-02-27 | Socony Vacuum Oil Co Inc | Method for conducting hightemperature conversions |
| US2508922A (en) * | 1948-05-17 | 1950-05-23 | Shell Dev | Separation of dienes |
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