CN101987821A - Method for preparing diallyl phthalate by using phydroxybenzene methyl ether as polymerization inhibitor - Google Patents
Method for preparing diallyl phthalate by using phydroxybenzene methyl ether as polymerization inhibitor Download PDFInfo
- Publication number
- CN101987821A CN101987821A CN2009103052863A CN200910305286A CN101987821A CN 101987821 A CN101987821 A CN 101987821A CN 2009103052863 A CN2009103052863 A CN 2009103052863A CN 200910305286 A CN200910305286 A CN 200910305286A CN 101987821 A CN101987821 A CN 101987821A
- Authority
- CN
- China
- Prior art keywords
- mehq
- phthalic acid
- diallyl ester
- stopper
- hour
- 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.)
- Pending
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention belongs to a method for preparing diallyl phthalate by using phydroxybenzene methyl ether as a polymerization inhibitor. The method comprises the following steps of: (1) salifying, namely adding phthalic anhydride and 40 percent sodium hydroxide solution into a reaction kettle, stirring and heating, refluxing for 1 hour, and cooling and filtering to obtain sodium phthalate; (2) esterifying, namely putting the sodium phthalate, a solvent, a catalyst and the phydroxybenzene methyl ether into the reaction kettle, heating to between 45 and 60 DEG C, dripping chloropropene, continuously keeping the temperature of between 45 and 60 DEG C and reacting for 1 hour, and cooling and filtering to obtain mixed solution; (3) neutralizing and washing; and (4) distilling, namely distilling an organic layer under reduced pressure to obtain distillate distilled at the temperature of between 160 and 170 DEG C and the vacuum degree of 4 to 6mmHg, namely a diallyl phthalate finished product. The method for preparing the diallyl phthalate by using the phydroxybenzene methyl ether as the polymerization inhibitor has the advantages of simple operation steps, high production efficiency, high stability and low raw material cost.
Description
Technical field
The invention belongs to field of fine chemical, especially a kind of method of utilizing MEHQ to prepare Phthalic acid, diallyl ester for stopper.
Background technology
Phthalic acid, diallyl ester is that petrochemical industry produces new variety, is widely used as linking agent, the properties-correcting agent of unsaturated polyester resin, the toughener of celluosic resin, and it has good thermotolerance, electrical property, ageing resistance etc.Phthalic acid, diallyl ester monomer and many monomers and unsaturated polymer copolymerization are to improve various performances.Can also be used to directly making watering casting and insulating varnish etc.At present among the preparation technology of Phthalic acid, diallyl ester, the used easy oxidation of stopper cuprous chloride, the easy moisture absorption and see that light decomposes easily, and also along with expanding economy, the cost of making the starting material copper of cuprous chloride rises very fast.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, provide a kind of manufacturing process steps simple, the MEHQ of utilizing that production efficiency is higher, stability is better, material cost is lower prepares the method for Phthalic acid, diallyl ester for stopper
The present invention is achieved through the following technical solutions:
A kind of MEHQ of utilizing the steps include: for stopper prepares the method for Phthalic acid, diallyl ester
(1) salify: phthalic anhydride and 40% sodium hydroxide solution are added fully stirring in the reactor,, refluxed 1 hour, be cooled to normal temperature with cold water and leach solid, obtain sodium phthalate with being steam heated to 100-110 ℃;
(2) esterification: sodium phthalate, solvent, catalyzer and MEHQ are put into reactor, feed steam to the reactor interlayer, temperature is controlled at 45-60 ℃, drip chloro propylene, added at 4-5 hour, continue to keep 45-60 ℃ of reaction after 1 hour, be cooled to normal temperature, filter and obtain mixed solution with cold water;
(3) neutralization, washing:, leave standstill with behind twice of the clear water cleaning mixture again to PH=8.3-8.7 with 5% sodium carbonate solution cleaning mixture three times, tell top organic layer;
(4) distillation: organic layer is imported the underpressure distillation still, remain under the 4-6mmHg vacuum tightness, obtain the fraction that steams under 160-170 ℃, be the Phthalic acid, diallyl ester finished product.
And described solvent is a dimethylbenzene.
And described catalyzer is a kind of in tosic acid or the Phenylsulfonic acid.
And the mol ratio of described phthalic anhydride, sodium hydroxide, solvent, propenyl chloride is: 0.8-1.2: 2.0-2.2: 2.5-3.5: 2.0-2.2.
And the mass ratio of described catalyzer and MEHQ is: 2.6-3.2: 0.8-1.2.
Advantage of the present invention and beneficial effect are:
1, utilize MEHQ to prepare for stopper that phthalic anhydride and liquid caustic soda reaction generate the phthalic acid sodium salt in the method for Phthalic acid, diallyl ester, under catalyzer, stopper effect, obtain crude product with propenyl chloride again in 40-60 O-C normal pressure esterification, neutralization after filtration,, washing, underpressure distillation obtain the Phthalic acid, diallyl ester finished product, the product purity that this kind method obtains is higher, good stability can reduce the pollution to environment.
2, manufacturing process steps of the present invention is simple, and production efficiency is higher, stability is better, material cost is lower, is to utilize MEHQ to prepare the method for Phthalic acid, diallyl ester for stopper.
Embodiment
The present invention is described in further detail by following examples.Need to prove: following embodiment is illustrative, is not determinate, can not limit protection scope of the present invention with following embodiment.
Embodiment 1
A kind of MEHQ of utilizing the steps include: for stopper prepares the method for Phthalic acid, diallyl ester
(1), salify: 1.1mol phthalic anhydride and 2.2mol40% sodium hydroxide solution are added fully stirring in the reactor,, refluxed 1 hour, be cooled to normal temperature with cold water and leach solid, obtain sodium phthalate with being steam heated to 105 ℃;
(2), esterification: will go up the sodium phthalate, 2.8mol dimethylbenzene, 3g tosic acid and the 1.2g MEHQ that obtain of step and put into reactor, feed steam to the reactor interlayer, make system temperature at 50 ℃, drip the 2.2mol propenyl chloride, added at 4.5 hours, continue to keep 50 ℃ of reactions after 1 hour, be cooled to normal temperature, filter and obtain mixed solution with cold water;
(3), neutralization, washing:, leave standstill with behind twice of the clear water cleaning mixture again to PH=8.5 with 5% sodium carbonate solution cleaning mixture three times, tell top organic layer;
(4), distillation: organic layer is imported the underpressure distillation still, open vacuum pump, the maintenance system is obtained the fraction that steams under 164 ℃ under 5mmHg vacuum tightness, be the Phthalic acid, diallyl ester finished product.
Embodiment 2
A kind of MEHQ of utilizing the steps include: for stopper prepares the method for Phthalic acid, diallyl ester
(1), salify: 1.0mol phthalic anhydride and 2.0mol40% sodium hydroxide solution are added fully stirring in the reactor,, refluxed 1 hour, be cooled to normal temperature with cold water and leach solid, obtain sodium phthalate with being steam heated to 102 ℃;
(2), esterification: will go up the sodium phthalate, 3.2mol dimethylbenzene, 2.8g tosic acid and the 0.8g MEHQ that obtain of step and put into reactor, feed steam to the reactor interlayer, make system temperature at 50 ℃, drip the 2.0mol propenyl chloride, added at 4.5 hours, continue to keep 50 ℃ of reactions after 1 hour, be cooled to normal temperature, filter and obtain mixed solution with cold water;
(3), neutralization, washing:, leave standstill with behind twice of the clear water cleaning mixture again to PH=8.7 with 5% sodium carbonate solution cleaning mixture three times, tell top organic layer;
(4), distillation: organic layer is imported the underpressure distillation still, open vacuum pump, the maintenance system is obtained the fraction that steams under 163 ℃ under 4.5mmHg vacuum tightness, be the Phthalic acid, diallyl ester finished product.
Embodiment 3
A kind of MEHQ of utilizing the steps include: for stopper prepares the method for Phthalic acid, diallyl ester
(1), salify: 0.8mol phthalic anhydride and 2.1mol40% sodium hydroxide solution are added fully stirring in the reactor,, refluxed 1 hour, be cooled to normal temperature with cold water and leach solid, obtain sodium phthalate with being steam heated to 106 ℃;
(2), esterification: will go up the sodium phthalate, 2.8mol dimethylbenzene, 3g Phenylsulfonic acid and the 1.0g MEHQ that obtain of step and put into reactor, feed steam to the reactor interlayer, make system temperature at 50 ℃, drip the 2.2mol propenyl chloride, added at 4.95 hours, continue to keep 48 ℃ of reactions after 1 hour, be cooled to normal temperature, filter and obtain mixed solution with cold water;
(3), neutralization, washing:, leave standstill with behind twice of the clear water cleaning mixture again to PH=8.5 with 5% sodium carbonate solution cleaning mixture three times, tell top organic layer;
(4), distillation: organic layer is imported the underpressure distillation still, open vacuum pump, the maintenance system is obtained the fraction that steams under 165 ℃ under 5mmHg vacuum tightness, be the Phthalic acid, diallyl ester finished product.
Claims (5)
1. one kind is utilized MEHQ to prepare the method for Phthalic acid, diallyl ester for stopper, and it is characterized in that: this preparation method's step is:
(1) salify: phthalic anhydride and 40% sodium hydroxide solution are added fully stirring in the reactor,, refluxed 1 hour, be cooled to normal temperature with cold water and leach solid, obtain sodium phthalate with being steam heated to 100-110 ℃;
(2) esterification: sodium phthalate, solvent, catalyzer and MEHQ are put into reactor, feed steam to the reactor interlayer, temperature is controlled at 45-60 ℃, drip chloro propylene, added at 4-5 hour, continue to keep 45-60 ℃ of reaction after 1 hour, be cooled to normal temperature, filter and obtain mixed solution with cold water;
(3) neutralization, washing:, leave standstill with behind twice of the clear water cleaning mixture again to PH=8.3-8.7 with 5% sodium carbonate solution cleaning mixture three times, tell top organic layer;
(4) distillation: organic layer is imported the underpressure distillation still, remain under the 4-6mmHg vacuum tightness, obtain the fraction that steams under 160-170 ℃, be the Phthalic acid, diallyl ester finished product.
2. the MEHQ of utilizing according to claim 1 prepares the method for Phthalic acid, diallyl ester for stopper, and it is characterized in that: described solvent is a dimethylbenzene.
3. the MEHQ of utilizing according to claim 1 is characterized in that for stopper prepares the method for Phthalic acid, diallyl ester: described catalyzer is a kind of in tosic acid or the Phenylsulfonic acid.
4. the MEHQ of utilizing according to claim 1 prepares the method for Phthalic acid, diallyl ester for stopper, and it is characterized in that: the mol ratio of described phthalic anhydride, sodium hydroxide, solvent, propenyl chloride is: 0.8-1.2: 2.0-2.2: 2.5-3.5: 2.0-2.2.
5. the MEHQ of utilizing according to claim 1 prepares the method for Phthalic acid, diallyl ester for stopper, and it is characterized in that: the mass ratio of described catalyzer and MEHQ is: 2.6-3.2: 0.8-1.2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009103052863A CN101987821A (en) | 2009-08-06 | 2009-08-06 | Method for preparing diallyl phthalate by using phydroxybenzene methyl ether as polymerization inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009103052863A CN101987821A (en) | 2009-08-06 | 2009-08-06 | Method for preparing diallyl phthalate by using phydroxybenzene methyl ether as polymerization inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101987821A true CN101987821A (en) | 2011-03-23 |
Family
ID=43744636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009103052863A Pending CN101987821A (en) | 2009-08-06 | 2009-08-06 | Method for preparing diallyl phthalate by using phydroxybenzene methyl ether as polymerization inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101987821A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734589A (en) * | 2019-01-24 | 2019-05-10 | 江苏扬农化工集团有限公司 | A kind of method for improving of epoxychloropropane tail gas safe |
-
2009
- 2009-08-06 CN CN2009103052863A patent/CN101987821A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734589A (en) * | 2019-01-24 | 2019-05-10 | 江苏扬农化工集团有限公司 | A kind of method for improving of epoxychloropropane tail gas safe |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20100042579A (en) | Method of preparing of 60% or more cis-di(c4-c20)alkyl cyclohexane-1,4-dicarboxylate | |
| CN101948387A (en) | Preparation technology of methyl benzoate | |
| CN112264090A (en) | Double-acid type ionic liquid catalyst and preparation method and application thereof | |
| CN101376631B (en) | Environment-protective preparation method of diglycol ethylene dibenzoate plasticiser | |
| CN107814939B (en) | Method for synthesizing poly (ethylene glycol methyl phosphonate) by metal oxide catalysis | |
| CN110845424B (en) | Preparation method of 5-acetoacetylaminobenzimidazolone | |
| CN114560770A (en) | Method for preparing ethyl sorbate by catalysis of supported p-toluenesulfonic acid | |
| CN110483268A (en) | A kind of method that heteropoly acid catalysis microcrystalline cellulose prepares levulic acid | |
| CN105085980A (en) | Synthesis of citric acid ether ester plasticizer | |
| CN102557946A (en) | Method for catalyzing to synthesize propyl gallate by acidic ionic liquid | |
| CN101987821A (en) | Method for preparing diallyl phthalate by using phydroxybenzene methyl ether as polymerization inhibitor | |
| CN105601496B (en) | A kind of preparation method of 3,4 dimethoxy benzenpropanoic acid | |
| CN102675112B (en) | Synthetic method of diphenyl iso-phthalate | |
| CN102503779A (en) | Preparation method of 3, 4, 5-trifluoromethylphenol | |
| CN102503823A (en) | Synthesis process for fatty acyl citrate compound | |
| CN107952479B (en) | Functionalized polyacid ionic liquid catalyst, preparation method and method for catalyzing direct esterification of cyclohexene by functionalized polyacid ionic liquid catalyst | |
| CN106220837A (en) | A kind of preparation method of high-purity light stabilizer 622 | |
| CN103232325B (en) | A kind of method being prepared hexalin by tetrahydrobenzene | |
| CN112679342A (en) | Preparation method of trans, trans-4, 4' -dicyclohexyl dicarboxylic acid | |
| CN101723832A (en) | Method for compounding allyl amyl glycolate | |
| CN111153794A (en) | Method for synthesizing ethyl palmitate by using dodecyl trimethyl ammonium chloride-based eutectic solvent catalyst | |
| CN1253131A (en) | Process for preparing multiring or fused-ring binary carboxylate by heteropoly acid catalysis | |
| CN109400468B (en) | Preparation method of L-dibenzoyl dimethyl tartrate | |
| CN102766051A (en) | Method for preparing benzyl benzoate by oxidizing dibenzyl ether | |
| CN102976939A (en) | Preparation method of propionate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20110323 |