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
- 238000004519 manufacturing process Methods 0.000 title description 6
- YOJKKXRJMXIKSR-UHFFFAOYSA-N 1-nitro-2-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1 YOJKKXRJMXIKSR-UHFFFAOYSA-N 0.000 title description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 125000006267 biphenyl group Chemical group 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 229950005499 carbon tetrachloride Drugs 0.000 description 5
- 238000006396 nitration reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- 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.
Landscapes
- 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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