CN101412734A - Phosphaphenanthrene-containing small molecular ester compound (ODOPB-DBC) and synthesis technique thereof - Google Patents
Phosphaphenanthrene-containing small molecular ester compound (ODOPB-DBC) and synthesis technique thereof Download PDFInfo
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- CN101412734A CN101412734A CNA200710063035XA CN200710063035A CN101412734A CN 101412734 A CN101412734 A CN 101412734A CN A200710063035X A CNA200710063035X A CN A200710063035XA CN 200710063035 A CN200710063035 A CN 200710063035A CN 101412734 A CN101412734 A CN 101412734A
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Abstract
The invention relates to a small molecule ester compound containing phosphoryl hybridizied, a derivant of the compound and a synthetic process. The compound comprises phthalic acid ODOPB diester and an alkoxy derivant (ODOPB-DBC). ODOPB-DBC is synthesized through two parts: in the first part, benzoyl chloride, an alkoxy group of the benzoyl chloride or an alkyl derivant and an ODOPB compound react and two molecules of chlorine hydride is removed to obtain an OPOPB-DBC compound; and in the second part, the OPOPB-DBC compound is subjected to precipitation and extraction in a solvent. The compound has excellent property of aggregative illumination and can carry out response arrangement on most organic gases, thereby achieving the function of gases detection; simultaneously, the solution of the compound can detect water containing heavy metal ions; therefore, the compound has application value in a chemical sensor and a metal ion detection reagent.
Description
Technical field
The present invention relates to a kind of synthetic and purifying process that contains the assorted luxuriant and rich with fragrance small molecular ester compound of phosphinylidyne.This compound comprises the derivative of dibenzoic acid ODOPB diester and alkyl and alkoxyl group.Its English name and be abbreviated as 2-(6-oxide-6H-dibenz＜c, e〉＜1,2〉oxaphos-phorin-6-yl)-and dihydroxyphenylene-dibenzenecarboxylate (ODOPB-DBC), below narration all is described this material with abbreviation ODOPB-DBC.Belong to the field of chemical synthesis.
Background technology
At present, carried out extensive studies to the synthetic of ODOPB and in the application in each field both at home and abroad, remove outside the purposes of above-mentioned introduction, ODOPB has also carried out corresponding research abroad being applied in of field such as features superpolymer, Resins, epoxy, luminescent materials, carried out preliminary research for this modified monomer in the application aspect above-mentioned, the synthesis technique of ODOPB and the application in high molecular polymer thereof have also been studied, at present, the reaction of itself and aromatic carboxylic acids being synthesized micromolecular compound does not appear in the newspapers.
ODOPB is a compound
The english abbreviation of 2-(6-oxide-6H-dibenz＜c, e〉＜1,2〉oxaphos-phorin-6-yl)-dihydroxyphenylene, below with this compound of ODOPB acute pyogenic infection of finger tip.
Summary of the invention
The present invention has synthesized the assorted luxuriant and rich with fragrance ester compound of a kind of brand-new small molecules phosphinylidyne, this compound is white or pale yellow powder, fusing point is arranged, cold crystallization temperature, second-order transition temperature, said temperature according to its different with the length of alkyl and alkoxyl group, this compound can be dissolved in chloroform, acetonitrile, methyl alcohol, multiple organic solvent such as ethanol.
The molecular formula of ODOPB-DBC
R=C
nH
2n+1Perhaps=OC
nH
2n+1Perhaps=H
n＝1-20
Present method synthetic (ODOPB-DBC) is divided into two parts and carries out first part: alkoxyl group or alkyl derivative and compound ODOPB reaction by Benzoyl chloride or Benzoyl chloride, remove bimolecular hydrogenchloride, and obtain compound OPOPB-DBC.Second section: this compound precipitated in solvent separate out extraction.
Used synthesis material phenylformic acid, alkoxybenzoic acid, alkylbenzoic acid (purity〉98%) ODOPB (purity〉98%) methyl alcohol, sherwood oil, normal hexane (purity〉99.5%) etc.
Synthesis technique
The first step: this step synthesizes and comprises two kinds of technologies; technology a: (or have alkyl, alkoxyl group by sulfur oxychloride (technical grade) and phenylformic acid; the alkyl wherein and the scope of alkoxyl group comprise methane to the straight chain of eicosyl and comprise the alkyl and the alkoxyl group of side chain) in molar ratio 1:1 in the 1:10 scope, feed intake; in 20-75 ℃ of scope, carry out acylation reaction; react and obtained corresponding acyl chlorides in 10-24 hour; when acyl chlorides above-mentioned and ODOPB were reacted, molar ratio was at 2:1 to 10:1.React in organic solvent, organic solvent can be toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, tetrahydrofuran (THF), acetonitrile, ethylene dichloride, DMF, DMSO equal solvent.Temperature of reaction is carried out between 60-250 ℃, reacts 1 hour-20 hours ODOPB-DBC and generates, and changes down step process over to and extracts.Technology b: the building-up reactions of the compound ODOPB-DBC compound of the application's requirement can be in mass polymerization, react under solvent-free condition, the ratio of two reactants is that to be 3:1 feed intake in the scope of 10:1 the molar ratio of acyl chlorides and ODOPB reacts under stirring.Temperature of reaction is carried out between 60-250 ℃, and the reaction times carried out back ODOPB-DBC and generates in 30 minutes-20 hours, changes down the step extraction over to.
Second step: pour into to precipitate in sherwood oil, hexane, the hexanaphthene equal solvent after the solution reaction thing reduced to room temperature 20-50 ℃ and separate out, adopt cloth formula funnel to carry out suction filtration then, and wash with sherwood oil or hexane or hexanaphthene.After 50-130 ℃ of oven dry, obtain DOPB-DPBC white solid powder, more than 95%, purity is respectively more than 99% the productive rate of two technologies respectively.With its pentane aminobenzoic acid ODOPB diester is example, and its nuclear magnetic spectrum is seen accompanying drawing 2.
This kind compound has excellent gathering emitting characteristics, and can respond arrangement to most of organic gass, thereby reach the effect that detects this gas, the solution of this material can detect the water that contains heavy metal ion simultaneously, so this compound can have using value aspect chemical sensor, the metal ion detection reagent.
Description of drawings
Fig. 1 is the reactional equation of ODOPB-DBC synthesis technique
Fig. 2 diamyl alkoxybenzoic acid ODOPB ester nuclear-magnetism figure
Embodiment:
Embodiment 3 is with Benzoyl chloride (1.40,0.01mol) and ODOPB (1g, 0.003mol) add in the 150ml four-hole boiling flask, add toluene 50ml, add the backflow prolong, magnetic agitation is heated to 110 ℃, reacts 20 hours, reaction finishes to pour in the 100ml sherwood oil under the stirring of back, and the adularescent precipitation is separated out.And wash with the 100ml sherwood oil, filtering-depositing was 120 ℃ of dryings 4 hours.Product dibenzoic acid ODOPB ester 1.55g, productive rate 97.5%, purity 98%.
Embodiment 4 second alkoxyl group Benzoyl chlorides (3.7,0.02mol) and ODOPB (1g, 0.003mol) put into the four-hole boiling flask that adds 150ml, add dimethylbenzene 50ml, add the backflow prolong, be heated to 140 ℃ under the magnetic agitation, reacted 15 hours, reaction finishes postcooling to room temperature, pours in the 200ml sherwood oil and separates out white precipitate under the stirring.Filtering-depositing was 120 ℃ of dryings 4 hours.Get product diethyl alkoxybenzoic acid ODOPB ester 1.8g, productive rate 96.7%, purity 99.0%.
Embodiment alkoxyl group Benzoyl chloride in 5 last of the ten Heavenly stems (2.97g, 0.01mol) and ODOPB (1g, 0.003mol), toluene 50ml adds in the four-hole boiling flask of 150ml, be heated to 110 ℃, reacted 12 hours, reaction finishes postcooling to 50 ℃, stirs to pour in the 100ml sherwood oil adularescent down into and precipitate and separate out.And wash with the 100ml hexanaphthene, filtering-depositing was 120 ℃ of dryings 4 hours.Product didecyl alkoxybenzoic acid ODOPB ester 2.45g, productive rate 96.7%, purity 98.5%.
Embodiment 6 ethyl group Benzoyl chlorides (1.685,0.01mol) and ODOPB (1g, 0.003mol), orthodichlorobenzene 40ml adds in the 150ml four-hole boiling flask, be heated to 110 ℃ under stirring, reacted 20 hours, reaction finishes postcooling to room temperature, pours in the 200ml sherwood oil under stirring and separates out.And wash with the 100ml sherwood oil, filtering-depositing was 120 ℃ of dryings 4 hours.Product diethylbenzene formic acid ODOPB ester 1.68g, productive rate 95%, purity 99.2%.
Claims (6)
1. one kind contains assorted luxuriant and rich with fragrance small molecular ester compound (ODOPB-DBC) of phosphinylidyne and synthesis technique thereof, it is characterized in that:
The molecular formula of this compound is:
R=C
nH
2n+1Perhaps=OC
nH
2n+1Perhaps=H
n＝1-20
2. a kind of assorted luxuriant and rich with fragrance small molecular ester compound (ODOPB-DBC) of phosphinylidyne that contains according to claim 1, it is characterized in that: this compound is white or pale yellow powder, fusing point is arranged, cold crystallization temperature, second-order transition temperature, said temperature according to its different with the length of alkyl and alkoxyl group, this compound can be dissolved in chloroform, acetonitrile, methyl alcohol, multiple organic solvent such as ethanol.
3. synthesis technique that contains the assorted luxuriant and rich with fragrance small molecular ester compound (ODOPB-DBC) of phosphinylidyne, its adopt phenylformic acid, alkoxybenzoic acid, alkylbenzoic acid, ODOPB, for raw material synthetic, and employing methyl alcohol, sherwood oil, normal hexane extraction; It is characterized in that this technology was divided into for two steps and carries out the first step: alkoxyl group by Benzoyl chloride or Benzoyl chloride or alkyl derivative and compound ODOPB reaction remove bimolecular hydrogenchloride, acquisition compound OPOPB-DBC; Second goes on foot: this compound is precipitated in solvent separate out extraction.
4. a kind of synthesis technique that contains the assorted luxuriant and rich with fragrance small molecular ester compound (ODOPB-DBC) of phosphinylidyne according to claim 3, it is characterized in that: synthesis technique adopts by sulfur oxychloride and phenylformic acid, or have an alkyl, alkoxyl group, the alkyl wherein and the scope of alkoxyl group comprise the straight chain and the alkyl and the alkoxyl group that comprise side chain of methane to eicosyl, 1:1 feeds intake in the 1:10 scope in molar ratio, in 20-75 ℃ of scope, carry out acylation reaction, react and obtained corresponding acyl chlorides in 10-24 hour, when acyl chlorides above-mentioned and ODOPB were reacted, molar ratio was at 2:1 to 10:1; React in organic solvent, organic solvent can be toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, tetrahydrofuran (THF), acetonitrile, ethylene dichloride, DMF, DMSO equal solvent, and temperature of reaction is carried out between 60-250 ℃, reacts 1 hour-20 hours.
5. a kind of synthesis technique that contains the assorted luxuriant and rich with fragrance small molecular ester compound (ODOPB-DBC) of phosphinylidyne according to claim 3, it is characterized in that: the building-up reactions of compound ODOPB-DBC can be in mass polymerization, react under solvent-free condition, the ratio of two reactants is that to be 3:1 feed intake in the scope of 10:1 the molar ratio of acyl chlorides and ODOPB reacts under stirring; Temperature of reaction is carried out between 60-250 ℃, and the reaction times carried out in 30 minutes-20 hours.
6. a kind of synthesis technique that contains the assorted luxuriant and rich with fragrance small molecular ester compound (ODOPB-DBC) of phosphinylidyne according to claim 3, it is characterized in that: reactant is reduced to pour into to precipitate in sherwood oil, hexane, the hexanaphthene equal solvent after the room temperature separate out, carry out suction filtration then, and wash with sherwood oil or hexane or hexanaphthene, 50-130 ℃ of oven dry.
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| CNA200710063035XA CN101412734A (en) | 2007-01-25 | 2007-01-25 | Phosphaphenanthrene-containing small molecular ester compound (ODOPB-DBC) and synthesis technique thereof |
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| CNA200710063035XA CN101412734A (en) | 2007-01-25 | 2007-01-25 | Phosphaphenanthrene-containing small molecular ester compound (ODOPB-DBC) and synthesis technique thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070770A (en) * | 2010-11-23 | 2011-05-25 | 沈阳化工大学 | Phosphorous epoxy resin curing agent and preparation method thereof |
| CN108641294A (en) * | 2018-05-08 | 2018-10-12 | 北京工商大学 | A kind of fire retarding epoxide resin based on the biradical compound of phospho hetero phenanthrene borate |
-
2007
- 2007-01-25 CN CNA200710063035XA patent/CN101412734A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070770A (en) * | 2010-11-23 | 2011-05-25 | 沈阳化工大学 | Phosphorous epoxy resin curing agent and preparation method thereof |
| CN102070770B (en) * | 2010-11-23 | 2012-11-28 | 沈阳化工大学 | Phosphorous epoxy resin curing agent and preparation method thereof |
| CN108641294A (en) * | 2018-05-08 | 2018-10-12 | 北京工商大学 | A kind of fire retarding epoxide resin based on the biradical compound of phospho hetero phenanthrene borate |
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Open date: 20090422 |