GB708564A - Process for the manufacture of solutions of 2-aminonaphthalene in organic solvents - Google Patents
Process for the manufacture of solutions of 2-aminonaphthalene in organic solventsInfo
- Publication number
- GB708564A GB708564A GB28933/51A GB2893351A GB708564A GB 708564 A GB708564 A GB 708564A GB 28933/51 A GB28933/51 A GB 28933/51A GB 2893351 A GB2893351 A GB 2893351A GB 708564 A GB708564 A GB 708564A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphuric acid
- aminonaphthalene
- boiling
- concentration
- organic solvents
- 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
Links
- 239000003960 organic solvent Substances 0.000 title abstract 5
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 235000011149 sulphuric acid Nutrition 0.000 abstract 4
- 239000001117 sulphuric acid Substances 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Solutions of beta-naphthylamine in organic solvents are prepared by heating 2-amino-naphthalene-1-sulphonic acid in the presence of an organic solvent with less than one molecular proportion of aqueous sulphuric acid at a temperature of 110-135 DEG C. and converting the resulting sulphate of 2-aminonaphthalene to the free base. The organic solvent and the concentration of the sulphuric acid are preferably chosen so that the boiling-point of the mixture is above 110 DEG C., but they may also be such that the boiling-point is below 110 DEG C., in which case it is necessary to work at above atmospheric pressure. Suitably the reaction is initiated with 0.25-0.5 molecular proportions of aqueous sulphuric acid which is maintained at a concentration below 80 per cent throughout the hydrolysis. Sulphuric acid is formed during the reaction and it is therefore necessary to add water if the concentration is to be kept constant, which may be arranged by hydrolysing in a circulatory distillation apparatus to allow addition or removal of water to keep the boiling temperature constantly between 120 DEG and 130 DEG C. The 2-aminonaphthalene-sulphate is converted to the base in situ by adding a solution or suspension of an alkali metal or alkaline earth metal hydroxide or carbonate. The aqueous layer is separated from the product and the remaining water removed by azeotropic distillation. Examples are given in which the specified organic solvents are chlorobenzene, o-dichlorobenzene and toluene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH708564X | 1950-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB708564A true GB708564A (en) | 1954-05-05 |
Family
ID=4530577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28933/51A Expired GB708564A (en) | 1950-12-15 | 1951-12-10 | Process for the manufacture of solutions of 2-aminonaphthalene in organic solvents |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB708564A (en) |
-
1951
- 1951-12-10 GB GB28933/51A patent/GB708564A/en not_active Expired
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