CAS name: 1-Naphthalenecarboxylic acid, 8-amino- Beil. 14.
Use: dye intermediate. There are 12 production and business units registered on LookChem.com.
BIOS 1152, 121. (= Film PB 81027). 1-Amino-8-naphthoic acid. Translated from German by the British, without specifying the source of the information.
The reaction formula is as follows:
Materials: Naphthostyril [ 130-00-7] is online. Hydrochloric acid 700 kg. Brine as necessary.
Procedure: Operation steps:
The batch (naphthostyril) is then blown onto 1000 l. cold water, and cooled to 20 – 25℃. Hydrochloric acid is then added in sufficient quantity to make it nearly neutral (300 l.).
It is then blown via screening press into a stirred vessel containing 1600 kg. ice and 400 l. hydrochloric acid. The temperature must not rise above 10℃. Then further acid is added to make the batch acid to methyl orange.
The precipitated aminonaphthoic acid is filtered on a nutsche and washed free from acid with brine.
Yield = 700 – 800 kg. paste. ≈145 kg. dry (M.W. 187) = 91.9 % theory.
FIAT 1313,II, 91-2. (= film PB 85172). 1-Carboxy-8-amino naphthalene. Translated from German by the British, no source of information stated.
The melt (naphthostyril) is transferred to a 5500 liter, cast iron, jacketed kettle, in which has been previously placed 1000 liters of water and after being well mixed, the charge is cooled by means of the jacket to 20 – 25℃.
350 kilograms of hydrochloric acid (31.5%) are then added slowly under the surface of the slurry, by means of a rubber lined pipe dipping below the surface of the charge.
This acid is added to cut down the bulk of alkalinity of the charge. , which should still be alkaline at the end of the addition. The volume of the charge at this point should be about 2500 liters.
The temperature is now adjusted to 25℃ and a sample sent to the laboratory, after which the charge is blown into a 6000 liter acid proof brick lined tank in which has previously been placed 1600 kilograms of ice and 560 kilograms of hydrochloric acid (31.5%).
Under these conditions with the temperature kept below 10℃, sulfur dioxide gas is evolved and foaming takes place and the 1-carboxy-8-amino naphthalene is precipitated.
The addition of hydrochloric acid is continued in small portions until a permanent acid reaction is obtained on Congo Red paper, avoiding, however, any large excess of acid. The slurry is then allowed to agitate for one hour and is filtered on a porous stone nutsch of three square meters filter atea.
The nutsch layer is washed with 200 liters of 50Be’ salt solution, through the kettle, then with two portions of 400 liters each of 50Be’ salt solution, being careful to avoid cracks in the layer.
The nutsch cake, which is nearly white in color, is sucked down well on the nutsch, and no color of sulfur dioxide should be apparent at this point.
Yield = 700 – 800 kilograms of paste = 172 kilograms dry equivalent (100% Mol. Wt.) = 93% of theory.
Hosoda Yui “Theoretical Manufacturing Dye Chemistry”. The technical report will be published soon. 1957. P. 729. 1-Carboxy-8-aminonaphthalene (8-Amino-1-naphthoic acid).
Naphthostyril に5.5 m3 のcast iron kettle water 1 tに加えジャケットで20 – 250 に热しHCl 359 kgを加えてアルカリのmost ををneutralized after , 6 m3 of acid-resistant tile making 1.6 t of ice in the open tank, 560 kg of hydrochloric acid, the SO2 content below 100 is discharged, and the acidic acid is precipitated. コンゴ- After acidic acidification for 1 hour, 3 m3 stone was filtered, NaCl 50Be’ solution was 200 l, and the kettle was washed with 400 l of ずつつ2 and backwashed. 172 kg (700 – 800 kg in mud form), yield 93%. (Translated from FIAT 1313).
PB 25627, 2257-2263. 1- Aminonaphthalene-8-carboxylic acid. Original German production process, September 1938. Not transcribed.
Shanghai Organic Chemical Industry Company “Dye Production Process Compilation”. 1976. P. 417-423. Production process of reduced ash BG, including 8-amino-1-naphthoic acid.
Naphthyllactam��Hydrolysis: Add a batch of naphthalene lactimide filter cake and 366 kg of liquid caustic soda (30%) into the pot, and adjust the volume to 1,100 liters. Heat to 95 – 100°C and keep warm for 2 hours. Cool to 50°C and filter to obtain 1,8-aminonaphthoic acid sodium salt 120 – 130 kg. (Note: The product is sodium salt. I have not found its CAS number yet. Its acid CAS number is [129-02-2]).
(Russian) A.B. Eлььцова “Laboratory Synthesis Methods of Dyes and Intermediates”. 1985. §2.3 Reduction of bright orange KX, including synthesis of 8-amino-1-naphthoic acid.
Place a 100 ml three-necked flask equipped with a stirrer, thermometer and reflux condenser. Place it in an electric heating oil bath, add 10 ml of water, and add the naphtholactam reaction material from the autoclave that has been heated to 50°C at a time with stirring. Heat it to 98-100°C, stir and keep warm for 3 hours.
Fix the 200 ml beaker with stirring in the collar, add 20 ml of cold water, add hot hydrolyzate under stirring, cool to 20 – 25°C, add concentrated hydrochloric acid (about 6 ml) to make it neutral to a wide range of test paper, then cool the material with ice salt water to -5 – -8°C , then acidify it with hydrochloric acid to a pH of 4-3 on a wide range of test paper, filter out the purity, wash the filter cake with 100 ml of 10% salt solution until it is neutral, drain it, and place the material in a petri dish and dry it in a 60°C oven.
Amount obtained: 5.6 grams, the product is light yellow needle-shaped body. (My translation is for reference only!)
“Organic Chemical Raw Materials and Intermediates Fact Sheet. Published by Liaoning Petrochemical Technology Information Station. in 1989. P. 604. 1,8-Aminonaphthoic acid.
[Preparation method] Hydrolysis of naphthalene lactimide.
Hou Leshan edited “China Fine Chemical Products Collection – 10,396 kinds of raw materials and intermediates” 》. year 2006. P. 48. 1-amino-8-naphthoic acid; 8-amino-1-naphthoic acid.
Published by China Chemical Information Center and National Fine Chemical Raw Materials and Intermediates Industry Collaboration Group. “Copyright. No reproduction without permission.”
Zhang Shusheng “Fine Chemical Intermediates and Product Production Process”. Published by Shenyang Institute. year 2006. P. 553. 1-Aminonaphthalene-8-carboxylic acid.
Hydrolysis of naphtholactam: put 300 L of water in a 2000 L hydrolysis pot and stir Add naphtholactam filter cake and 180 kg of 100% sodium hydroxide, and add water until the total volume is 1500 L. Raise the temperature to 110 – 120°C, keep stirring for 2 hours, cool to 30°C, add 300 kg of hydrochloric acid in a thin stream to neutralize, and obtain 1-aminonaphthalene-8-carboxylic acid.
(Note: No source!).
He Yanbin is the editor-in-chief of “Encyclopedia of Dyes Varieties”. Published by Shenyang Publishing House. 2018. P. 1943. Chinese name: 8-amino-1-naphthoic acid.
[Synthesizable dyes] C.I. Vat Orange 3; C.I. Vat Orange 9; C.I. Pigment Red 168.
Note: The information on hand is limited, so I can only copy it here!
Chen Zhongyuan Wednesday, December 30, 2020.
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