CN100406430C - Method for preparing Meldrum's base [4,4'-methanodi-(N,N-dimethylaniline)] - Google Patents
Method for preparing Meldrum's base [4,4'-methanodi-(N,N-dimethylaniline)] Download PDFInfo
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- CN100406430C CN100406430C CNB2006100534466A CN200610053446A CN100406430C CN 100406430 C CN100406430 C CN 100406430C CN B2006100534466 A CNB2006100534466 A CN B2006100534466A CN 200610053446 A CN200610053446 A CN 200610053446A CN 100406430 C CN100406430 C CN 100406430C
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- accelerine
- base
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- dimethylaniline
- hydrochloride
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
the invention discloses a preparing method of 4,4'-methano-2(N, N-dimethylaniline), which comprises the following steps: aerating HCl in the N, N-dimethylaniline; stirring continuously at 0 deg.c to prepare N, N-dimethylaniline hydrochlorate; 2) putting N, N-dimethylaniline and carbon tetrachloride in the ion liquid to react to produce hydrochlorate of Mie alkaline under 85-95 deg.c; neutralizing through alkaline; extracting through chloroform; decompressing to distill to obtain the product.
Description
Technical field
The present invention relates to the method for a kind of preparation tetra-base [4,4 '-methylene radical two (N, accelerine)], belong to the organic compound preparing technical field.
Background technology
Compound with arylamine structure has important use in dyestuffs industries and medicine are synthetic.This compounds has been widely used in many clothes, the synthetic aspect of some medicines of dye well of aspects such as daily necessities.
The method of existing preparation tetra-base [4,4 '-methylene radical two (N, accelerine)] adopts carbon tetrabromide and N mostly, and accelerine carries out in acetonitrile, and carbon tetrabromide is more expensive, and acetonitrile has very big toxicity, should not use in actual production.
Summary of the invention
The purpose of this invention is to provide the method that a kind of high yield, environmental friendliness and technology simply prepare tetra-base [4,4 '-methylene radical two (N, accelerine)].
The method of preparation tetra-base of the present invention [4,4 '-methylene radical two (N, accelerine)], its step is as follows:
1. the method for preparation tetra-base [4,4 '-methylene radical two (N, accelerine)], its step is as follows:
1) freshly prepd HCl gas is fed N, in the accelerine,, constantly under the intense stirring condition, make ionic liquid N, the accelerine hydrochloride at 0 ℃;
2) in ionic liquid, drop into N, accelerine and tetracol phenixin, ionic liquid, N, the mol ratio of accelerine and tetracol phenixin is 1: 1: 1～2, reacts 18～32 hours under 85～95 ℃ of temperature. generate the hydrochloride of tetra-base, neutralize with alkali, use chloroform extraction, underpressure distillation gets tetra-base [4,4 '-methylene radical two (N, accelerine)].
Its chemical equation is as follows:
The present invention has the following advantages:
1, with tetracol phenixin as reaction raw materials, environmental friendliness, cheap and easy to get, be applicable to prepared in laboratory and industrial-scale production.
2, ionic liquid N, accelerine hydrochloride are again good solvents as catalyzer simultaneously, and be non-volatile in reaction, do not lose, and can be recycled, and reactive activity does not change, and can really realize cleaner production.
3, technology is simple, and the reaction times is short, and reaction only needs underpressure distillation can obtain high-quality product.Productive rate can reach 40～60%.
Specific embodiments
Embodiment 1
(1) freshly prepd HCl gas is fed N, among the accelerine 315.48g (2.59mol),, constantly under the intense stirring condition, make ionic liquid N, accelerine hydrochloride 2.59mol at 0 ℃;
(2) in ionic liquid, drop into N, accelerine 315.48g (2.59mol) and tetracol phenixin 797.5g (5.18mol), ionic liquid and N, the mol ratio of accelerine and tetracol phenixin is 1: 1: 2, reaction is 24 hours under 90 ℃ of temperature, reacted the hydrochloride of back generation tetra-base, with in 40% the sodium hydroxide solution and after, use chloroform extraction, remove other components by underpressure distillation, tetra-base [4,4 '-methylene radical two (N, accelerine)] 109.4g (0.43mol).Productive rate 50%.
Embodiment 2
(1) at 0 ℃, constantly under the intense stirring condition, freshly prepd HCl gas is fed N, among the accelerine 315.48g (2.59mol), make ionic liquid N, the accelerine hydrochloride;
(2) in ionic liquid, drop into N, accelerine 315.48g (2.59mol) and tetracol phenixin 398.25g (2.59mol), ionic liquid and N, the mol ratio of accelerine and tetracol phenixin is 1: 1: 1, reaction is 24 hours under 90 ℃ of temperature, reacted the back and generated the hydrochloride of tetra-base, with in 40% the sodium hydroxide solution and after, use chloroform extraction, remove other components by underpressure distillation, tetra-base [4,4 '-methylene radical two (N, accelerine)] 87.884g.Productive rate 40%.
Embodiment 3
(1) at 0 ℃, constantly under the intense stirring condition, freshly prepd HCl gas is fed N, among the accelerine 315.48g (2.59mol), make ionic liquid N, the accelerine hydrochloride;
(2) in ionic liquid, drop into N, accelerine 315.48g (2.59mol) and tetracol phenixin 598.125g (3.885mol), ionic liquid and N, the mol ratio of accelerine and tetracol phenixin is 1: 1: 1.5, reaction is 32 hours under 95 ℃ of temperature, reacted the back and generated the hydrochloride of tetra-base, with in 40% the sodium hydroxide solution and after, use chloroform extraction, remove other components by underpressure distillation, tetra-base [4,4 '-methylene radical two (N, accelerine)] 125.86g.Productive rate 58%.
Claims (1)
- Preparation tetra-base 4,4 '-method of methylene radical two (N, accelerine), its step is as follows:1) freshly prepd HCl gas is fed N, in the accelerine,, constantly under the intense stirring condition, make N, the accelerine hydrochloride at 0 ℃;2), drop into N in the accelerine hydrochloride, accelerine and tetracol phenixin to N, N, accelerine hydrochloride, N, the mol ratio of accelerine and tetracol phenixin is 1: 1: 1～2, under 85～95 ℃ of temperature, reacted 18～32 hours, generate the hydrochloride of tetra-base,, use chloroform extraction with the alkali neutralization, underpressure distillation, tetra-base 4,4 '-methylene radical two (N, accelerine).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100534466A CN100406430C (en) | 2006-09-18 | 2006-09-18 | Method for preparing Meldrum's base [4,4'-methanodi-(N,N-dimethylaniline)] |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100534466A CN100406430C (en) | 2006-09-18 | 2006-09-18 | Method for preparing Meldrum's base [4,4'-methanodi-(N,N-dimethylaniline)] |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1923796A CN1923796A (en) | 2007-03-07 |
| CN100406430C true CN100406430C (en) | 2008-07-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB2006100534466A Expired - Fee Related CN100406430C (en) | 2006-09-18 | 2006-09-18 | Method for preparing Meldrum's base [4,4'-methanodi-(N,N-dimethylaniline)] |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1035660A (en) * | 1988-03-10 | 1989-09-20 | 化学工业部沈阳化工研究院 | 2, the preparation and the application thereof of 6-dimethyl benzene hydrazine derivative |
-
2006
- 2006-09-18 CN CNB2006100534466A patent/CN100406430C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1035660A (en) * | 1988-03-10 | 1989-09-20 | 化学工业部沈阳化工研究院 | 2, the preparation and the application thereof of 6-dimethyl benzene hydrazine derivative |
Non-Patent Citations (6)
| Title |
|---|
| 4,4′-四甲二氨基二苯甲烷的合成. 林吉文，魏春红.应用化学，第6期. 1987 |
| 4,4′-四甲二氨基二苯甲烷的合成. 林吉文，魏春红.应用化学，第6期. 1987 * |
| Novel reaction of dimethylaniline with tetrabromomethaneproducing 4,4'-methylenebis(N,N-dimethylaniline).. Matsubara, Yoshio.Synthetic Communications,Vol.33 No.11. 2003 |
| Novel reaction of dimethylaniline with tetrabromomethaneproducing 4,4'-methylenebis(N,N-dimethylaniline).. Matsubara, Yoshio.Synthetic Communications,Vol.33 No.11. 2003 * |
| 高纯度4,4’-N,N’-二甲氨基二苯甲烷的合成. 苏广武，李梅香，罗先金.染料工业，第5期. 2000 |
| 高纯度4,4’-N,N’-二甲氨基二苯甲烷的合成. 苏广武，李梅香，罗先金.染料工业，第5期. 2000 * |
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| CN1923796A (en) | 2007-03-07 |
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