CN107793334A - Aryl sulfonic acid ammonium salt compound, its preparation method and application - Google Patents
Aryl sulfonic acid ammonium salt compound, its preparation method and application Download PDFInfo
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- CN107793334A CN107793334A CN201710892885.4A CN201710892885A CN107793334A CN 107793334 A CN107793334 A CN 107793334A CN 201710892885 A CN201710892885 A CN 201710892885A CN 107793334 A CN107793334 A CN 107793334A
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- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
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- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- 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
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Abstract
The invention discloses a kind of aryl sulfonic acid ammonium salt compound, its preparation method and application, main process is expressed as follows：Using the aryl sulfonic acid class crude compound shown in structure formula (I) as raw material, mixed in a solvent with the organic amine shown in structure formula (II), form the aryl sulfonic acid ammonium salt shown in structure formula (III)；Aryl sulfonic acid ammonium salt shown in resulting structures formula (III) obtains the aryl sulfonic acid class compound fine work shown in structure formula (I) through alkali-soluble acid analysis or direct acid out.
Description
Technical field
The present invention relates to the preparation method of organic compound, more particularly to a kind of aryl sulfonic acid ammonium salt compound and its system
Preparation Method and application.
Background technology
Aryl sulfonic acid class compound, e.g., adjacent (, to) nitrobenzene-sulfonic acid, neighbour (, to) toluene sulfonic acide, neighbour (, to)
Aminobenzenesulfonic acid etc., it is a kind of important organic chemical industry's intermediate, is widely used in the synthesis of medicine, agricultural chemicals, dyestuff.
Research is found, conventional to produce aryl sulfonic acid class compound, can be produced some impurity, be caused aryl sulfonic acid class compound
Purity is not high (the principal product purity not post-processed typically is not more than 85%), influences further making for aryl sulfonic acid class compound
With.Such as o-nitrobenzene sulfonic acid, its preparation method can be substantially expressed as follows：Using ortho-nitrochlorobenzene as predominant starting material, with two
Vulcanized sodium is that sulfiding reagent obtains double (dinitrophenyl) disulphide, double oxidized dose of oxygen of (dinitrophenyl) disulphide
Change, the process such as hydrolysis prepares o-nitrobenzene sulfonic acid under basic conditions.Molecular weight 292,388,315 etc. and ortho-nitrophenyl sulphur can be produced
Sour polarity it is extremely close and have be not aryl sulfonic acid class compound impurity, common purification process is very difficult to remove, to using being catalyzed
The preparation process that o-nitrobenzene sulfonic acid is converted into orthanilic acid by hydrogenating reduction method is unfavorable, greatly reduces metallic catalyst
Service life and orthanilic acid quality.
The content of the invention
The purpose of the present invention is overcome the deficiencies in the prior art, there is provided a kind of aryl sulfonic acid ammonium salt compound and its preparation side
Method and application, used technical scheme are：
A kind of aryl sulfonic acid ammonium salt compound, the structural formula of compound is as follows,
Wherein, R, R1、R2、R3Separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one
Kind, R, R1、R2、R3In at least one selection nitro or halogen atom.
It is the invention also discloses the preparation method of above-mentioned aryl sulfonic acid ammonium salt compound, the step of its method：With structure
Aryl sulfonic acid class compound shown in formula (I) is raw material, is mixed in a solvent with the organic amine shown in structure formula (II), forms knot
Aryl sulfonic acid ammonium salt shown in structure formula (III), the wherein aryl sulfonic acid shown in structure formula (I) with it is organic shown in structure formula (II)
The mol ratio of amine is 1:1~1.05, the mass ratio of the aryl sulfonic acid shown in the solvent and structure formula (I) is 2~10:1,
Said process represents as follows with reaction equation,
Wherein, R, R1、R2、R3Separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one
Kind, R, R1、R2、R3In at least one selection nitro or halogen atom.
Further, the aryl sulfonic acid class compound shown in described structure formula (I) is single aryl sulfonic acid class compound
Or the mixture of several aryl sulfonic acid class compounds, described solvent are water, acetone, methanol, 1,2- dichloroethanes, toluene
One or more of mixed solvents.
The invention also discloses application of the above-mentioned aryl sulfonic acid ammonium salt compound in refined aryl sulfonic acid class compound, bag
Include following steps：
The first step, aryl sulfonic acid ammonium salt shown in structure formula (III), inorganic base and water hybrid reaction obtained into structural formula (IV
Or IV') shown in aryl sulfonic acid inorganic metal salt, mole of aryl sulfonic acid ammonium salt shown in described inorganic base and structure formula (III)
Than 1.0~3.0:1, described water is 3~6 with aryl sulfonic acid ammonium salt mass ratio shown in structure formula (III):1；
After the organic base separation to dissociate in second step, the mixture for obtaining the first step, remaining aqueous phase is adjusted to PH=with acid
1~3, post processing, obtain the aryl sulfonic acid ammonium salt compound fine work shown in structure formula (I)；
Said process represents as follows with structural formula：
Wherein, R, R1、R2、R3Separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one
Kind, R, R1、R2、R3In at least one selection nitro or halogen atom.
Further, described inorganic base be the hydroxide of alkali metal, one kind of the carbonated of alkali metal, it is described
Acid is hydrochloric acid, one kind of sulfuric acid, and described post processing includes separation of solid and liquid, drying.
The invention also discloses another kind of the above-mentioned aryl sulfonic acid ammonium salt compound in refined aryl sulfonic acid class compound
Method, its step are：By aryl sulfonic acid ammonium salt shown in structure formula (III) and water hybrid reaction, inorganic acid is added to system PH=1
~3, post processing, obtain the aryl sulfonic acid ammonium salt compound fine work shown in structure formula (I)；
Said process represents as follows with structural formula：
Wherein, R, R1、R2、R3Separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one
Kind, R, R1、R2、R3In at least one selection nitro or halogen atom.
Further, the mass ratio of described water and aryl sulfonic acid ammonium salt shown in structure formula (III) is 3~6:1, it is described
Inorganic acid is hydrochloric acid, one kind of sulfuric acid.
A kind of aryl sulfonic acid ammonium salt compound disclosed by the invention and preparation method and application, by structure formula (I)
Shown aryl sulfonic acid class crude compound is converted into the aryl sulfonic acid ammonium salt compound shown in structure formula (II), then by alkali
The method of molten acid out or direct acid out obtains the aryl sulfonic acid class compound fine work shown in structure formula (I), effectively easily removes
Objectionable impurities in aryl sulfonic acid class crude compound, aryl sulfonic acid class compound purity by 87~88% improve to 99.5% with
On, after recycled, aryl sulfonic acid class compound loss late is only 2.5 ‰.
Embodiment
The following examples further illustrate some features of the present invention, but the present invention applies for the content of protection
Do not limited with scope by following embodiments.
Embodiment 1
By the o-nitrobenzene sulfonic acid crude product of 2000 kilograms of active constituent contents 87% and 10000 kilograms of acetone, 1551 kilograms
Dicyclohexylamine mixes, and obtains 3840 kilograms of o-nitrobenzene sulfonic acid dicyclohexyl ammonium salts.
The structural formula of gained o-nitrobenzene sulfonic acid dicyclohexyl ammonium salt is such as：
Hydrogen nuclear magnetic resonance modal data, 1HNMR (500MHz, CDCl3)：8.55 (d, 1H), 8.10 (d, 1H), 8.02 (dd,
1H), 7.73 (dd, 1H), 7.01 (s, 2H), 3.55 (m, 2H), 2.57 (m, 8H), 1.45~1.55 (m, 12H).
Molecular formula：C18H28N2O5S
Molecular weight：384.1720
Solubility：Water is dissolved in, is slightly soluble in ethanol, insoluble in petroleum ether
Said compound classification：Salt
3840 kilograms of o-nitrobenzene sulfonic acid dicyclohexyl ammonium salts are mixed with 11520 kg of water, 800 kilograms of sodium hydroxides,
Stratification removes organic phase, and aqueous phase is acidified to PH=1.0 through hydrochloric acid, obtains the ortho-nitrophenyl of 1653 kilograms of purity 99.8%
Sulfonic acid fine work.
The hydrogen nuclear magnetic resonance modal data of gained o-nitrobenzene sulfonic acid fine work, 1HNMR (500MHz, CDCl3)： 8.51(d,
1H), 8.09 (d, 1H), 8.00 (dd, 1H), 7.76 (dd, 1H), 1.97 (br, 1H).
Embodiment 2
Obtained through embodiment 1 3840 kilograms of 2- chlorobenzenesulfonic acid dicyclohexyl ammonium salts are mixed with 11520 kg of water, use salt
Acid is acidified to system PH=1.0, obtains the 2- chlorobenzenesulfonic acid fine work of 1608 kilograms of purity 99.9%.
Embodiment 3
The acidity obtained by obtained through embodiment 1 3840 kilograms of 3- chlorobenzenesulfonic acid dicyclohexyl ammonium salts and through embodiment 2
Mother liquid coming mixes, and hydrochloric acid regulation PH=1.0, obtains the 3- chlorobenzenesulfonic acid fine work of 1688 kilograms of purity 99.7%.
Embodiment 4
By the p-nitrophenyl sulfonic acid crude product of 2000 kilograms of active constituent contents 88% and 10000 kilograms of methanol, 1551 kilograms
Dicyclohexylamine mixes, and obtains 3840 kilograms of p-nitrophenyl sulfonic acid dicyclohexyl ammonium salts.
The structural formula of gained p-nitrophenyl sulfonic acid dicyclohexyl ammonium salt is such as：
Hydrogen nuclear magnetic resonance modal data, 1HNMR (500MHz, CDCl3)：8.40 (d, 2H), 8.10 (d, 2H), 7.00 (s,
2H), 3.53 (m, 2H), 2.00~2.30 (m, 8H), 1.40~1.6 (m, 12H).
Molecular formula：C18H28N2O5S
Molecular weight：384.1720
Solubility：Water is dissolved in, is slightly soluble in ethanol, insoluble in petroleum ether
Said compound classification：Salt
3840 kilograms of p-nitrophenyl sulfonic acid dicyclohexyl ammonium salts are mixed with 11520 kg of water, 1380 kilograms of potassium carbonate, it is quiet
Put layering and remove organic phase, aqueous phase is acidified to PH=1.0 through hydrochloric acid, obtains the p-nitrophenyl sulfonic acid of 1653 kilograms of purity 99.8%
Fine work.
Gained p-nitrophenyl sulfonic acid fine work hydrogen nuclear magnetic resonance modal data, 1HNMR (500MHz, CDCl3)：8.38 (d, 2H),
8.10 (d, 2H), 2.00 (br, 1H).
Embodiment 5
By the p-methyl benzenesulfonic acid crude product of 2000 kilograms of active constituent contents 88% and 20000 kilograms of 1,2- dichloroethanes,
1085 kilograms of triethylamine mixing, obtain 2681.7 kilograms of p-methyl benzenesulfonic acid triethylamine salts.
The structural formula of gained p-methyl benzenesulfonic acid triethylamine salt is such as：
Hydrogen nuclear magnetic resonance modal data, 1HNMR (500MHz, CDCl3)：7.77 (d, 2H), 7.39 (d, 2H), 7.02 (s,
1H), 3.26 (q, 6H), 1.57 (t, 9H), 2.37 (s, 3H).
Molecular formula：C13H23NO3S
Molecular weight：273.1398
Solubility：Water is dissolved in, is slightly soluble in ethanol, insoluble in petroleum ether
Said compound classification：Salt
2681.7 kilograms of p-methyl benzenesulfonic acid triethylamine salts are mixed with 10727 kg of water, sulfuric acid is acidified to system PH=
3, obtain the p-methyl benzenesulfonic acid fine work of 1584 kilograms of purity 99.8%.
The hydrogen nuclear magnetic resonance modal data of gained p-methyl benzenesulfonic acid fine work, 1HNMR (500MHz, CDCl3)：7.74 (d,
2H), 7.41 (d, 2H), 2.35 (s, 3H), 2.01 (br, 1H).
Embodiment 6
Done using 2681.7 kilograms of p-nitrophenyl sulfonic acid triethylamine salts caused by the method for embodiment 4 as raw material, acid mother liquid water
Bottom water, system PH=3 is acidified to sulfuric acid, is repeated 10 times, its result is as shown in the table：
Claims (7)
1. a kind of aryl sulfonic acid ammonium salt compound, it is characterised in that the structural formula of compound is as follows,
Wherein, R, R1, R2, R3 separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one kind, R,
At least one selection nitro or halogen atom in R1, R2, R3.
2. the preparation method of a kind of aryl sulfonic acid ammonium salt compound, it is characterised in that：
Using the aryl sulfonic acid class compound shown in structure formula (I) as raw material, in a solvent with structure formula (II) shown in organic amine
Mixing, form the aryl sulfonic acid ammonium salt shown in structure formula (III), aryl sulfonic acid and structural formula wherein shown in structure formula (I)
(II) mol ratio of the organic amine shown in is 1:1~1.05, the mass ratio of the solvent and the aryl sulfonic acid shown in structure formula (I)
For 2~10:1,
Said process represents as follows with reaction equation,
Wherein, R, R1、R2、R3Separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one kind, R,
R1、R2、R3In at least one selection nitro or halogen atom.
3. the preparation method of a kind of aryl sulfonic acid ammonium salt compound as claimed in claim 2, it is characterised in that described structure
Aryl sulfonic acid class compound shown in formula (I) is the mixing of single aryl sulfonic acid class compound or several aryl sulfonic acid class compounds
Thing, described solvent are water, acetone, methanol, 1,2- dichloroethanes, one or more of mixed solvents of toluene.
4. a kind of aryl sulfonic acid ammonium salt compound described in any one of claims 1 to 3 is in refined aryl sulfonic acid class compound
Application, it is characterised in that：
The first step, aryl sulfonic acid ammonium salt shown in structure formula (III), inorganic base and water hybrid reaction obtained into structural formula (IV or
IV' aryl sulfonic acid inorganic metal salt shown in), the mol ratio of described inorganic base and aryl sulfonic acid ammonium salt shown in structure formula (III)
1.0~3.0:1, described water is 3~6 with aryl sulfonic acid ammonium salt mass ratio shown in structure formula (III):1；
After the organic base separation to dissociate in second step, the mixture for obtaining the first step, remaining aqueous phase is adjusted to PH=1~3 with acid,
Post processing, obtains the aryl sulfonic acid ammonium salt compound fine work shown in structure formula (I)；
Said process represents as follows with structural formula：
Wherein, R, R1、R2、R3Separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one kind, R,
R1、R2、R3In at least one selection nitro or halogen atom.
5. application of a kind of aryl sulfonic acid ammonium salt compound as claimed in claim 4 in refined aryl sulfonic acid class compound,
Characterized in that, described inorganic base is the hydroxide of alkali metal, one kind of the carbonated of alkali metal, described acid is salt
Acid, one kind of sulfuric acid, described post processing include separation of solid and liquid, drying.
6. a kind of aryl sulfonic acid ammonium salt compound described in any one of claims 1 to 3 is in refined aryl sulfonic acid class compound
Application, it is characterised in that by aryl sulfonic acid ammonium salt shown in structure formula (III) and water hybrid reaction, add inorganic acid to system
PH=1~3, post processing, obtain the aryl sulfonic acid ammonium salt compound fine work shown in structure formula (I)；
Said process represents as follows with structural formula：
Wherein, R, R1、R2、R3Separately selected from hydrogen, nitro, halogen atom, 1~6 carbon atom alkyl in one kind, R,
R1、R2、R3In at least one selection nitro or halogen atom.
7. application of a kind of aryl sulfonic acid ammonium salt compound as claimed in claim 6 in refined aryl sulfonic acid class compound, its
It is characterised by, the mass ratio of described water and aryl sulfonic acid ammonium salt shown in structure formula (III) is 3~6:1, described inorganic acid is
One kind of hydrochloric acid, sulfuric acid.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108276314A (en) * | 2018-03-27 | 2018-07-13 | 九江善水科技股份有限公司 | A kind of naphthalene ammonium salt compound and the preparation method and application thereof |
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| CN108276314A (en) * | 2018-03-27 | 2018-07-13 | 九江善水科技股份有限公司 | A kind of naphthalene ammonium salt compound and the preparation method and application thereof |
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