US1980537A - Manufacture of 2-nitrodiphenyl - Google Patents
Manufacture of 2-nitrodiphenyl Download PDFInfo
- Publication number
- US1980537A US1980537A US703677A US70367733A US1980537A US 1980537 A US1980537 A US 1980537A US 703677 A US703677 A US 703677A US 70367733 A US70367733 A US 70367733A US 1980537 A US1980537 A US 1980537A
- Authority
- US
- United States
- Prior art keywords
- nitrodiphenyl
- manufacture
- nitric acid
- diphenyl
- nitration
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
Definitions
- My present invention relates to an improved process for manufacturing Z-nitrodiphenyl.
- the object is achieved by nitrating with strong nitric acid the diphenyl dissolved in carbon tetrachloride.
- the carbon tetrachloride layer is separated from the acid, washed with water until neutral and filtered from a small quantity of 4.4-dinitrcdiphenyl.
- the 2-derivative distils at 178 and 179 C. and the -derivative between 190 and 200 C.
- the distillation residue contains essentially 2,4-dinitrodipheny1 of melting point 93 C.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Nov. 13, 1934 MANUFACTURE OF Z-NITRODIPHENYL No Drawing. Application December 22, 1933, Serial No. 703,677. In Germany December 24,
2 Claims.
My present invention relates to an improved process for manufacturing Z-nitrodiphenyl.
The manufacture of mono-nitrodiphenyl, the parent material for making mono-aminodi phenyl, is described in various literature. In an article by L. R. Jenkins and others (Industrial Engineering Chemistry, vol. 22, page 31 /34=) there is a useful summary of this literature. The nitration is conducted with strong nitric acid, a mixture of glacial acetic acid and nitric acid or the so-called mixed acid. In all cases the reaction produces i-nitrodiphenyl in by far preponderating proportions and only a small proportion of Z-nitrodiphenyl. The statement of Fortinski (J. Russ, Phys. Ch. Ges, 44, 781-87) that he obtained from 180 grams of diphenyl 105 grams of i-nitrodiphenyl and 110 grams of Z-nitrodiphenyl by nitration with a mixture of glacial acetic acid and nitric acid, that is to say a yield of about 45 and 47 per cent. respectively, has been rejected by de Crauw (Rec. trav. chim. 50 (1931) page 753 and following).
It is the object of the present invention to conduct the mono-nitration of diphenyl in such a manner that, in contrast with past experience, there is a satisfactory production of 2-nitrodiphenyl, since it is this body which has technical interest as being the material from which 2- aminodiphenyl, the intermediate product of the manufacture of dyes, is made.
The object is achieved by nitrating with strong nitric acid the diphenyl dissolved in carbon tetrachloride.
For example, to a solution of 1000 parts by weight of diphenyl in 3000 parts of carbon tetrachloride there is run, while strongly stirring, 1600 parts of nitric acid of 1.45 specific gravity in the course of 2 hours, the temperature being kept,
rice
by cooling, at about 18 C. The mixture is then heated to boiling in a reflux apparatus for 20 hours.
After it has cooled, the carbon tetrachloride layer is separated from the acid, washed with water until neutral and filtered from a small quantity of 4.4-dinitrcdiphenyl.
The carphenyl.
In the vacuum (13 mm.) the 2-derivative distils at 178 and 179 C. and the -derivative between 190 and 200 C. The distillation residue contains essentially 2,4-dinitrodipheny1 of melting point 93 C.
A similar effect is obtained when using chloroform as a solvent in which the nitration of diphenyl is carried out with strong nitric acid. With the aid of this chlorinated hydrocarbon nitration occurs very smoothly, whereat only mononitro derivatives are formed and orthonitrodiphenyl likewise is obtained with a satisfactory yield.
What I claim is:
1. The process which comprises nitrating diphenyl with strong nitric acid in the presence of a solvent of the group consisting of carbon tetrachloride and chloroform.
2. The process which comprises nitrating diphenyl with strong nitric acid in the presence of carbontetrachloride.
HANS LANGE.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1980537X | 1932-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1980537A true US1980537A (en) | 1934-11-13 |
Family
ID=7857255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US703677A Expired - Lifetime US1980537A (en) | 1932-12-24 | 1933-12-22 | Manufacture of 2-nitrodiphenyl |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1980537A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435544A (en) * | 1940-12-05 | 1948-02-03 | Autoxygen Inc | Method of nitrating organic compounds |
| US2448823A (en) * | 1944-03-11 | 1948-09-07 | Sun Chemical Corp | Tribiphenylmethane dyestuff and pigment dyestuffs and process for making the same |
-
1933
- 1933-12-22 US US703677A patent/US1980537A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435544A (en) * | 1940-12-05 | 1948-02-03 | Autoxygen Inc | Method of nitrating organic compounds |
| US2448823A (en) * | 1944-03-11 | 1948-09-07 | Sun Chemical Corp | Tribiphenylmethane dyestuff and pigment dyestuffs and process for making the same |
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