CN1349981A - 2-naphtylamine-6-sulfonyl aniline and its prepn and application - Google Patents
2-naphtylamine-6-sulfonyl aniline and its prepn and application Download PDFInfo
- Publication number
- CN1349981A CN1349981A CN 01133567 CN01133567A CN1349981A CN 1349981 A CN1349981 A CN 1349981A CN 01133567 CN01133567 CN 01133567 CN 01133567 A CN01133567 A CN 01133567A CN 1349981 A CN1349981 A CN 1349981A
- Authority
- CN
- China
- Prior art keywords
- compound
- aniline
- naphtylamine
- acid
- broenner
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种名称为2－萘胺－6－磺酰苯胺的化合物、该化合物的制备方法与及其用途。它是将布龙酸与醋酐作用制得乙酰布龙酸,然后将干燥的乙酰布龙酸与氯磺酸、氯化亚砜作用,经冰析、水洗而得乙酰布龙酸的磺酰氯化合物,与苯胺反应后,经水解、中和而得到产物。此化合物可作为染料中间体,其制备方法简单,产率高,产品质量好,具有很好的出口前景。The invention discloses a compound named 2-naphthylamine-6-sulfonanilide, a preparation method of the compound and an application thereof. It is prepared by reacting blononic acid with acetic anhydride to obtain acetobronic acid, then reacting the dried acetobronic acid with chlorosulfonic acid and thionyl chloride, iced out and washed with water to obtain the sulfonyl chloride of acetobronic acid The compound, after reacting with aniline, is hydrolyzed and neutralized to obtain the product. The compound can be used as a dye intermediate, the preparation method is simple, the yield is high, the product quality is good, and it has a good export prospect.
Description
Affiliated technical field
The present invention relates to a kind of new naphthylamines sulfonanilide compounds and preparation method and purposes, specifically is exactly the compound that a kind of name is called the 2-naphtylamine-6-sulfonyl aniline, the preparation method and its usage of this compound.
Background technology
Through the retrieval of Hubei Province's Scientific And Technical Intelligence Center, there is no this compound of report both at home and abroad, there is not synthetic method yet.The amino common methods of protection is to make acetylation reagent with aceticanhydride under alkaline condition, and productive rate generally is about 85%, and the waste water of brownish black, contaminate environment are arranged.
The innovation and creation content
The object of the present invention is to provide a kind of name to be called the compound of 2-naphtylamine-6-sulfonyl aniline, the preparation method of this compound and purposes, this compound can be used as dyestuff intermediate, and its simple synthetic method is pollution-free, productive rate height, good product quality.
Concrete technical scheme is as follows:
A kind of name is called the compound of 2-naphtylamine-6-sulfonyl aniline, and its structural formula is:
The fusing point 218-220 of this compound ℃, can be used as dyestuff intermediate.
A kind of method of the 2-of preparation naphtylamine-6-sulfonyl aniline: it is with acetyl Broenner'sacid and chlorsulfonic acid, sulfur oxychloride effect, through ice analyse, wash and the sulfonyl chloride compound of acetyl Broenner'sacid, behind aniline reaction, obtain product through hydrolysis, neutralization again.The reaction formula for preparing this compound is:
According to technical scheme of the present invention, when synthetic by the acetyl Broenner'sacid: chlorsulfonic acid: the ratio of sulfur oxychloride=1: 2.8-3.1: 0.8-1.0 (weight ratio) is fed in raw material, stir down 2h at 45-50 ℃, ice is analysed, is washed then, with the gained intermediate in pH=11～12 time with the aniline effect, then at pH=14,95-98 ℃ of following hydrolysis 2h, be cooled to 50 ℃, be neutralized to neutrality with hydrochloric acid, product is separated out in cooling, filter, wash and promptly get qualified product twice.
According to technical scheme of the present invention, described acetyl Broenner'sacid is under alkaline condition, and Broenner'sacid and aceticanhydride stir 1.5h at 85-90 ℃, directly dries and gets.
In this step of acetylization reaction; the consumption of strict control water; after reaction is finished; negative pressure drying; thereby improved productive rate, avoided waste water, chlorosulphonation is crucial; feed ratio is pressed the acetyl Broenner'sacid: chlorsulfonic acid: sulfur oxychloride=1: 2.8-3.1: 0.8-1.0 (weight ratio) can reach the present invention's purpose.
Adopt technical scheme of the present invention, do not have brownish black waste water in this step of acetylization reaction, avoided environmental pollution, productive rate is near 100%, and can satisfy the specification of quality of subsequent reactions, greatly reduces production cost, improved economic benefit; In chlorosulfonation, strict control acetyl Broenner'sacid: chlorsulfonic acid: the ratio of sulfur oxychloride, its quality product reaches export requirement.
The fusing point 218-220 of compound of the present invention ℃, product is analyzed through HPLC, and content is greater than 98%, and total recovery 94% has good application prospects and prospect of export.
Embodiment
Embodiment 1
Add 100mL water, NaOH7g, Broenner'sacid 30g, aceticanhydride 16g in there-necked flask, 85-90 ℃ is stirred 1.5h down, and drying under reduced pressure gets the acetyl Broenner'sacid.
Add chlorsulfonic acid 31g, exsiccant acetyl Broenner'sacid 10.5g, sulfur oxychloride 9g in another there-necked flask, 45-50 ℃ is stirred 2h down, and pour into then ice in the frozen water that 120g ice adds 130g water and analyse, filtration, product washs to pH=4-5 with frozen water.
Wet the said products is packed in the there-necked flask, add entry 70mL, transfer pH=12, add the new aniline that steams of 7g with 50%NaOH, 20-25 ℃ is reacted 2h down, constantly adds alkali and keeps pH=12, adds 50%NaOH 14g then, 95-98 ℃ of hydrolysis 2h cools to 50 ℃, transfers pH=7 with 36% hydrochloric acid.Product is separated out in cooling, filters, and washes twice and gets qualified product, and overall yield 94% is analyzed content＞98% through PHLC.
Embodiment 2
In the 250ml there-necked flask, add entry 35ml, sodium hydroxide 2.2g adds Broenner'sacid 10g after the stirring and dissolving, aceticanhydride 5.5g is warmed up to 70 ℃ of dissolvings, and 80～90 ℃ of stirring reactions 1 hour incline to vaporizer, dry to constant weight under the infrared lamp, get acetyl Broenner'sacid 12.70g, productive rate 98.6%.
In the 100ml there-necked flask, add chlorsulfonic acid 28g (be reflected in the Fume Hoods and carry out), stir and add exsiccant acetyl Broenner'sacid 10g down, 0.5 add chlorination sulfoxide 8g after hour again, 45 ℃ ± 2 times stirring reactions 1.5 hours, then under agitation in impouring 120g ice and the 120g water, separate out the bright yellow product, negative pressure filtration, frozen water are washed till pH=5～6.
Above-mentioned wet product is placed the 250ml there-necked flask, add entry 60ml, stir into pasty state, the solution that drips NaOH30% drips the new aniline 6.5g that steams to pH=11～12 o'clock, at room temperature stirs after adding 1.5 hours, the pH value can constantly descend, and should replenish NaOH in good time, to keep pH=11～12, add 30%NaOH20g then, 93～100 ℃ of stirring reactions 2 hours cool to 40 ℃, HCl with 18% transfers pH6～7, and product, filtration under diminished pressure are separated out in cooling, washing twice, total recovery about 94%.High pressure liquid chromatographic analysis: content 98%.
Claims (3)
1. a name is called the compound of 2-naphtylamine-6-sulfonyl aniline, and its structural formula is:
2. the described compound 2-of claim 1 naphtylamine-6-sulfonyl aniline is as dyestuff intermediate.
3. method for preparing the described compound 2-of claim 1 naphtylamine-6-sulfonyl aniline, it is characterized in that: with exsiccant acetyl Broenner'sacid and chlorsulfonic acid, sulfur oxychloride by 1: the weight ratio of 2.8-3.1: 0.8-10 feeds intake, at 45-50 ℃ of stirring reaction, ice is analysed, is washed then, the sulfonyl chloride compound of gained acetyl Broenner'sacid promptly obtains product through hydrolysis, neutralization in pH=11～12 time and aniline reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB01133567XA CN1142137C (en) | 2001-10-19 | 2001-10-19 | 2-naphthylamine-6-sulfonanilide and its preparation method and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB01133567XA CN1142137C (en) | 2001-10-19 | 2001-10-19 | 2-naphthylamine-6-sulfonanilide and its preparation method and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1349981A true CN1349981A (en) | 2002-05-22 |
| CN1142137C CN1142137C (en) | 2004-03-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB01133567XA Expired - Fee Related CN1142137C (en) | 2001-10-19 | 2001-10-19 | 2-naphthylamine-6-sulfonanilide and its preparation method and use |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1142137C (en) |
-
2001
- 2001-10-19 CN CNB01133567XA patent/CN1142137C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1142137C (en) | 2004-03-17 |
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