US2485185A - Nitroparawin solvent process for - Google Patents
Nitroparawin solvent process for Download PDFInfo
- Publication number
- US2485185A US2485185A US2485185DA US2485185A US 2485185 A US2485185 A US 2485185A US 2485185D A US2485185D A US 2485185DA US 2485185 A US2485185 A US 2485185A
- Authority
- US
- United States
- Prior art keywords
- limonene
- olefins
- nitrosochloride
- nitroparawin
- nitrosyl chloride
- 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 28
- 239000002904 solvent Substances 0.000 title description 20
- VPCDQGACGWYTMC-UHFFFAOYSA-N Nitrosyl chloride Chemical class ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 50
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-(4R)-Limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 26
- 150000001336 alkenes Chemical class 0.000 description 22
- 239000004157 Nitrosyl chloride Substances 0.000 description 20
- 235000019392 nitrosyl chloride Nutrition 0.000 description 20
- -1 cyclic olefins Chemical class 0.000 description 16
- 125000004432 carbon atoms Chemical group C* 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XMGQYMWWDOXHJM-UHFFFAOYSA-N (+-)-(RS)-limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229930007650 limonene Natural products 0.000 description 10
- 235000001510 limonene Nutrition 0.000 description 8
- 229940087305 limonene Drugs 0.000 description 8
- MCSAJNNLRCFZED-UHFFFAOYSA-N Nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N Nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004971 nitroalkyl group Chemical group 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- NALZTFARIYUCBY-UHFFFAOYSA-N 1-nitrobutane Chemical compound CCCC[N+]([O-])=O NALZTFARIYUCBY-UHFFFAOYSA-N 0.000 description 2
- UZONFOPDCXAZND-UHFFFAOYSA-N 1-nitroheptane Chemical compound CCCCCCC[N+]([O-])=O UZONFOPDCXAZND-UHFFFAOYSA-N 0.000 description 2
- KLGHUFNKRIWCDQ-UHFFFAOYSA-N 1-nitrooctane Chemical compound CCCCCCCC[N+]([O-])=O KLGHUFNKRIWCDQ-UHFFFAOYSA-N 0.000 description 2
- BVALZCVRLDMXOQ-UHFFFAOYSA-N 1-nitropentane Chemical compound CCCCC[N+]([O-])=O BVALZCVRLDMXOQ-UHFFFAOYSA-N 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000998 L-alanino group Chemical group [H]N([*])[C@](C([H])([H])[H])([H])C(=O)O[H] 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N Octadecene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229940058172 ethylbenzene Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 125000002298 terpene group Chemical group 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
Definitions
- This invention relates to a new and. improved process for converting olefins. to their nitrosochlorides.
- Olefins have heretoforebeen converted to. their nitrosochlorides by dissolving them in solvents such. as alcohols and. organic acids and passing nitrosyl chloride through. the solution.
- solvents such. as alcohols and. organic acids
- nitrosyl chloride through. the solution.
- the yields obtained by these prior art processes are, however, unsatisfactory, and vary widely with slight changesin the operating conditions.
- nitroparafiins as solvents for the olefins undergoing reaction.
- our in;- vention is directed to the employment oinitroparafi'ins having from one to eight, carbon" atoms as solvents in the reaction between, olefins and nitrosyl chloride.
- this invention is concerned with a process wherein olefins, particularly cyclic olefins, and preferably those of the terpene group, are dissolved in a nitroparafiin containing from one to four carbon atoms, after which nitrosyl chloride is passed through the solution.
- One of the preferred embodiments of this invention involves carrying on the foregoing reaction while maintaining the olefin-nitroparaffin solution at low temperatures, advisably below 0 C. and preferably in the neighborhood of 35" C. for those nitroparafiins which are liquid at these temperatures.
- Example 1 Over a 1 hour period, 44 g. of nitrosyl chloride was bubbled into a mixture of 100 g. of d-limonene in 200 cc. of nitromethane, maintained between C. and C. The mixture was stirred throughout the period and for an additional 0.25 hour at the above temperature. It was filtered and the precipitate washed with approximately 200 cc. of cold ether. The solid nitrosochloride weighed 64 g.. representing a 43 per cent conversion of the d-limonene.
- Example 2 Overa period of 1- hour, 20- g. ofnitrosyl chloride was bubbled into amixtureof 46g, ot'dlimonene in cc. of nitroethane, maintained between 40 C. and 50" C; The-mixture was stirred throughoutthis period and for an additional 2.5' hours while it washeld within the above temperature range. Thesolid; d-limonene' nitrosochloride was isolated by filtration; washed with 200 cc. of cold ether, andair-dried'; its weight was 26g, representing a 38 pereent'conversion of the d-limonene.
- nitromethane and nitroethane solvent theretmay be employed nitropropane, nitrobutane, nitropentane, nitroheptane, or nitrooctane, with satisfactory results.
- isomers, as well as mixtures of such solvents may be used.
- the nitro group may be substituted on any of the various possible positions in the alkane radical. It is also contemplated that higher members of the nitroalkane series may be employed, although for optimum results we prefer to use nitroalkanes having no more than eight carbon atoms in the molecule, and preferably from one to four carbon atoms.
- the conditions of reaction set forth in the foregoing examples may be varied considerably without departing from the scope of this invention.
- the relative amount of the reactants may be varied substantially and the temperature and time of reaction may likewise be varied considerably.
- it is preferred to use temperatures below 10 C. and preferably in the neighborhood of 35 C. for those nitroparafiins which are liquid at these temperatures. which the olefin-nitroalkane solution is maintained at these temperatures may be varied considerably in accordance with well-known refrigeration technique.
- the manner in This invention is applicable to the conversion of olefins generally to their orresponding nitrosochlorides by treatment with nitrosyl chloride.
- the olefins may be either cyclic or acyclic in nature.
- a representative group of cyclic olefins is, for example, cyclohexene, methyl cyolohexene, 8,9-dihydrolimonene, l-limonene, dipentene, ocpinene, fl-pinene, and the like.
- a representative group of acyclic olefins is, for example, octane-1, octene-2, styrene, stilbene, hexadecene, octadecene, and the like.
- mixtures of one or more olefins may be treated in accordance with this invention. This is particularly desirable in the case of those olefins which are difiicult to separate from their homologs, wherein the employment of a mixture substantially reduces the cost of the operation.
- this invention broadly contemplates the treatment of cyclic and acyclic olefins, it is to be understood that it is particularly adapted to the conversion of cyclic olefins, especially those of the terpene class, to their corresponding nitrosochlorides.
- the preferred embodiment of this invention is the treatment of limonene, preferably d-limonene.
- a process which comprises dissolving an olefin having at least six carbon atoms in a nitroparafiin having from one to eight carbon atoms, passing nitrosyl chloride therethrough at a temperature below 0 C., and thereafter separating the resulting nitrosochloride therefrom.
- a process which comprises dissolving a terpene olefin in a nitroparafiin having from one to eight carbon'atoms, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting nitrosochloride therefrom.
- a process which comprises dissolving limonene in a nitroparafiin having from one to four carbon atoms, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting limonene nitrosochloride therefrom.
- a process which comprises dissolving d-limonene in nitromethane, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting d-limonene nitrosochloride therefrom.
- a process which comprises dissolving d-limonene in nitroethane, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting d-limonene nitrosochloride therefrom.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fire-Extinguishing Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Oct. 18, 1949 NITROPA-HAFFI'N SOLVENT PROGESS-FOR- MAKING; OLEFI-N: NITROSOGHEORIDES Carl Bordenca and Wilbur, A... Lazier, Birmingham, Ala... assignors to Food Machinery and Chemical Corporation, a corporation of'Delaware NoDnawing. ApplicationrMarch 25,1947, SeriaLNo. 73, 7,102
5 Claims. 1
This invention, relates to a new and. improved process for converting olefins. to their nitrosochlorides.
Olefins have heretoforebeen converted to. their nitrosochlorides by dissolving them in solvents such. as alcohols and. organic acids and passing nitrosyl chloride through. the solution. The yields obtained by these prior art processes are, however, unsatisfactory, and vary widely with slight changesin the operating conditions.
It, is anobject of this. invention to convert olefins to their nitrosochlorides by a new and improved process which produces high yields of the desired end product. A further object is to produce these compounds by a process which may be controlled readily and which is simple and economical. Additional objects; willobecome apparent from a consideration of the following description and claims.
These objects are attained in accordance with our present invention, which involves the use of nitroparafiins as solvents for the olefins undergoing reaction. In. a more restricted; sense our in;- vention is directed to the employment oinitroparafi'ins having from one to eight, carbon" atoms as solvents in the reaction between, olefins and nitrosyl chloride. Infa still; more limited sense this invention is concerned with a process wherein olefins, particularly cyclic olefins, and preferably those of the terpene group, are dissolved in a nitroparafiin containing from one to four carbon atoms, after which nitrosyl chloride is passed through the solution. One of the preferred embodiments of this invention involves carrying on the foregoing reaction while maintaining the olefin-nitroparaffin solution at low temperatures, advisably below 0 C. and preferably in the neighborhood of 35" C. for those nitroparafiins which are liquid at these temperatures.
The invention may be more readily understood by a consideration of the following illustrative examples:
Example 1 Over a 1 hour period, 44 g. of nitrosyl chloride was bubbled into a mixture of 100 g. of d-limonene in 200 cc. of nitromethane, maintained between C. and C. The mixture was stirred throughout the period and for an additional 0.25 hour at the above temperature. It was filtered and the precipitate washed with approximately 200 cc. of cold ether. The solid nitrosochloride weighed 64 g.. representing a 43 per cent conversion of the d-limonene.
It is to be noted that when the same procedure was followed and a temperature range of +5 C.
2 to +7 C; was employed; only 52g. of'd-limonene nitrosochloride was obtained, representing a- 35 per cent conversion of 'the limonene.
Example 2 Overa period of 1- hour, 20- g. ofnitrosyl chloride was bubbled into amixtureof 46g, ot'dlimonene in cc. of nitroethane, maintained between 40 C. and 50" C; The-mixture was stirred throughoutthis period and for an additional 2.5' hours while it washeld within the above temperature range. Thesolid; d-limonene' nitrosochloride was isolated by filtration; washed with 200 cc. of cold ether, andair-dried'; its weight was 26g, representing a 38 pereent'conversion of the d-limonene.
Whereas; in the above examples it has been shown that conversion of d-limonene to its nitrosochloride is obtained in certain solvents, it should be noted that at temperatures of 0 C. or below the reaction apparently does not occur in carbon tetrachloride, carbon disulfide, ethyl acetate, benzene, and ether in the absence of high- 1y polar substances. In methyl, ethyl, and butyl alcohols conversions under 25 per cent have been obtained.
In the above examples in place of thenitromethane and nitroethane solvent theretmay be employed nitropropane, nitrobutane, nitropentane, nitroheptane, or nitrooctane, with satisfactory results. Likewise, isomers, as well as mixtures of such solvents, may be used. In the same manner the nitro group may be substituted on any of the various possible positions in the alkane radical. It is also contemplated that higher members of the nitroalkane series may be employed, although for optimum results we prefer to use nitroalkanes having no more than eight carbon atoms in the molecule, and preferably from one to four carbon atoms.
It is to be understood that the conditions of reaction set forth in the foregoing examples may be varied considerably without departing from the scope of this invention. For example, the relative amount of the reactants may be varied substantially and the temperature and time of reaction may likewise be varied considerably. As a general rule, it is preferred to use temperatures below 10 C. and preferably in the neighborhood of 35 C. for those nitroparafiins which are liquid at these temperatures. which the olefin-nitroalkane solution is maintained at these temperatures may be varied considerably in accordance with well-known refrigeration technique.
The manner in This invention is applicable to the conversion of olefins generally to their orresponding nitrosochlorides by treatment with nitrosyl chloride. The olefins may be either cyclic or acyclic in nature. A representative group of cyclic olefins is, for example, cyclohexene, methyl cyolohexene, 8,9-dihydrolimonene, l-limonene, dipentene, ocpinene, fl-pinene, and the like. A representative group of acyclic olefins is, for example, octane-1, octene-2, styrene, stilbene, hexadecene, octadecene, and the like.
It is to be understood that mixtures of one or more olefins may be treated in accordance with this invention. This is particularly desirable in the case of those olefins which are difiicult to separate from their homologs, wherein the employment of a mixture substantially reduces the cost of the operation.
While this invention broadly contemplates the treatment of cyclic and acyclic olefins, it is to be understood that it is particularly adapted to the conversion of cyclic olefins, especially those of the terpene class, to their corresponding nitrosochlorides. The preferred embodiment of this invention, as is evident from the above examples, is the treatment of limonene, preferably d-limonene.
By means of the present invention a simple and economical process for the production of nitrosochlorides is rendered available. This is an important reaction, but heretofore, so far as we are aware, the yields, and therefore the expense of the operation, was unsatisfactory. We have now found that this difliculty is in large measure attributable to the use of an inefficient solvent system. The solvent system of our invention, particularly in conjunction with the employment of low temperatures, avoids these and other disadvantages inherent in the prior art.
As many apparently widely different embodiments of this invention may be made without departing from the spirit and scope hereof, it is to be understood that the invention is not limited to the specific embodiments hereof except as defined in the appended claims.
We claim:
1. A process which comprises dissolving an olefin having at least six carbon atoms in a nitroparafiin having from one to eight carbon atoms, passing nitrosyl chloride therethrough at a temperature below 0 C., and thereafter separating the resulting nitrosochloride therefrom.
2. A process which comprises dissolving a terpene olefin in a nitroparafiin having from one to eight carbon'atoms, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting nitrosochloride therefrom.
3. A process which comprises dissolving limonene in a nitroparafiin having from one to four carbon atoms, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting limonene nitrosochloride therefrom.
4. A process which comprises dissolving d-limonene in nitromethane, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting d-limonene nitrosochloride therefrom.
5. A process which comprises dissolving d-limonene in nitroethane, maintaining the solution at a temperature below 10 C., passing nitrosyl chloride therethrough, and thereafter separating the resulting d-limonene nitrosochloride therefrom.
CARL BORDENCA. WILBUR A. LAZIER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Name Date Beckham Mar. 18, 1947 OTHER REFERENCES Number
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2485185A true US2485185A (en) | 1949-10-18 |
Family
ID=3436671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2485185D Expired - Lifetime US2485185A (en) | Nitroparawin solvent process for |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2485185A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3076038A (en) * | 1959-06-11 | 1963-01-29 | Studiengesellschaft Kohle Mbh | Process for the production of cyclododecadiene-mononitrosochlorides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417675A (en) * | 1947-03-18 | Crystalline olefin-nitrosyl chlo |
-
0
- US US2485185D patent/US2485185A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417675A (en) * | 1947-03-18 | Crystalline olefin-nitrosyl chlo |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3076038A (en) * | 1959-06-11 | 1963-01-29 | Studiengesellschaft Kohle Mbh | Process for the production of cyclododecadiene-mononitrosochlorides |
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