CN1070187C - Process for prepn. of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-S-triazine - Google Patents
Process for prepn. of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-S-triazine Download PDFInfo
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- CN1070187C CN1070187C CN96121532A CN96121532A CN1070187C CN 1070187 C CN1070187 C CN 1070187C CN 96121532 A CN96121532 A CN 96121532A CN 96121532 A CN96121532 A CN 96121532A CN 1070187 C CN1070187 C CN 1070187C
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- 238000000034 method Methods 0.000 title claims description 33
- FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 title abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 25
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002841 Lewis acid Substances 0.000 claims abstract description 10
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003849 aromatic solvent Substances 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 238000002955 isolation Methods 0.000 abstract 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 229960001755 resorcinol Drugs 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 1
- -1 4-xylyl Chemical group 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a preparation of 2-(2,4-dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-s-triazine of formula comprises (a) reacting cyanuric chloride with 1,3-xylene at 0-110 degrees C in the presence of 2.3-3.0 mole Lewis acid/mole and inert chlorinated aromatic solvent(s) by adding 2.1-2.5 mole; and then (b) reacting (IV), without isolation, with 0.5-1.0 mole resorcinol/mole at 0-100 DEG C.
Description
The present invention relates to prepare 2-(2, the 4-dihydroxy phenyl)-4 new easy the thereby more economical method of 6-two (2, the 4-xylyl)-s-triazine by cyanuryl chloride.
By cyanuryl chloride and 1,3-dimethylbenzene reacts under the Friedel-Crafts condition and prepares 2-chloro-4, and (2, the 4-3,5-dimethylphenyl)-the s-triazine is known to 6-two, for example sees DE-A-1 169 947 and Helv.Chim.Acta 5,1589 (1972).But, also can use suitable Grignard reagent to obtain this product, for example see Helv.Chim.Acta 33,1365 (1950) and US-A 4092466.
2-chloro-4,6-two (2, the 4-3,5-dimethylphenyl)-s-triazine (it is purified by recrystallization method in advance) the further reaction with Resorcinol is described among the US-A-3244708.
But, direct and two equivalents 1 of cyanuryl chloride, the shortcoming of 3-dimethylbenzene reaction is also to form list and trisubstitution product in addition.Particularly, list-xylyl derivative is undesirable because in subsequently and reaction Resorcinol it can cause forming corresponding two-resorcinol compound.When using ultraviolet ray (UV) absorption agent that is made by formula I compound in various polymkeric substance, two-resorcinol compound can cause flavescence, for example in some paint.Formerly have in the technological method,, avoid forming this pair-resorcinol compound (Helv.Chim.Acta 5,1575 (1972)) through circuitous dichloro-alkoxyl group-s-triazine route.
Have found that now, can as described belowly prepare 2-(2, the 4-dihydroxy phenyl)-4,6-two (2, the 4-3,5-dimethylphenyl)-and the s-triazine: in so-called single still method, in the presence of Lewis acid and inertia chlorinated aromatic hydrocarbons solvent, make cyanuryl chloride and 1, the reaction of 3-dimethylbenzene, the chloro-s-triazine intermediate that does not separate formation is subsequently with resorcin reaction; In the method, beat all is in first reactions steps, under the situation that does not increase by three replacement by products, not form the two chloro-s-triaizine compounds that single aryl replaces basically.
In addition, can also eliminate uncontrollable thermopositive reaction (when adding raw material and catalyzer at the same time this phenomenon can take place) with above-mentioned reaction method, thereby operate safer referring to DE-A-1169947 or BP 884802.
As solvent, both not only used formula III compound itself, do not use dithiocarbonic anhydride (Helv.Chim.Acta 55,1589 (1972)), and reaction mixture does not become solid-state (DE-A-1169947) yet yet.
Therefore, the invention provides 2-shown in a kind of preparation formula I (2, the 4-dihydroxy phenyl)-4, the method for 6-two (2, the 4-3,5-dimethylphenyl)-s-triazine
This method comprises:
A) at 0-110 ℃, in the presence of Lewis acid and at least a inertia chlorinated aromatic hydrocarbons solvent,, make shown in cyanuryl chloride shown in the formula II and the formula III 1 by in 5-30 hour, adding compound shown in the formula III, 3-dimethylbenzene reacts
Obtain compound shown in the formula IV
Wherein, with respect to every mole cyanuryl chloride, lewis acidic consumption is 2.3-3.0mol, 1, and the consumption of 3-dimethylbenzene is 2.1-2.5mol; Then
B) do not separate the formula IV compound that obtains, make itself and Resorcinol 0-100 ℃ of reaction, obtain compound shown in the formula I, wherein, with respect to every mole of cyanuryl chloride, the consumption of Resorcinol is 0.5-1.0mol.
In the step a) of this method, compound shown in the formula III preferably divides 2 batches of addings.Generally speaking, at first add 0.5-1.1mol, add 2.0-1.0mol formula III compound then.Temperature when adding the 1st batch is 60-110 ℃, particularly 75-95 ℃, and the temperature when adding the 2nd batch is 20-50 ℃, particularly 30-40 ℃.In a preferred embodiment, at first 60-110 ℃, in 2-12 hour endo form II compound, add the formula III compound of 0.5-1.0mol, then 20-50 ℃, in 5-15 hour, be metered into the 2nd batch of formula III compound of 2.0-1.0mol.Be generally less than at two batches of cooling stagess between reinforced and equal 3 hours, for example 0.1-3 hour, particularly 0.5-2.5 hour.
In a particularly preferred embodiment, in the step a) of this method, at first 83-87 ℃, in 3.5-4.5 hour, add 0.85-1.0mol formula III compound, then this mixture is cooled to 33-37 ℃, counted 1.4-1.6 hour, afterwards 33-37 ℃, in 5.5-6.5 hour, add 1.45-1.3mol formula III compound.
In step a), use aromatic solvent or mixture, for example one, two or trichlorobenzene or its mixture, particularly chlorobenzene or dichlorobenzene, as 1, the 2-dichlorobenzene.
In step b), can use the solvent different with step a).The suitable solvent for example is oil of mirbane, methyl-phenoxide, chlorobenzene and 1,2-dichlorobenzene or their mixture.
If in step b), use the solvent that is different from the step a), can partially or completely remove the solvent in the 1st step, for example distillation is removed.
But, preferably also use the chlorinated aromatic hydrocarbons solvent in the step b), particularly with step a) in identical solvent.
In step a), known in the art for the reaction of Friedel-Crafts reaction in employed Lewis acid preferably aluminum chloride or aluminum bromide, preferred especially aluminum chloride.Used Lewis acid is preferably substantially anhydrous.
Lewis acidic consumption is preferably 2.4-2.6mol with respect to every mole of cyanuryl chloride.
Need not be separated in the formula IV compound that forms in the step a), can directly carry out step b), that is, not need in the methods of the invention the product of step a) is carried out aftertreatment, because in step a), do not form list-xylyl compound basically.Three-xylyl compound of higher percent, therefore can reclaim in filtrate because this compound is stayed in the solution when separating final product not influence of further reaction.
In step b), preferably use the Resorcinol of 0.7-0.8 mole with respect to every mole of cyanuryl chloride, and preferably during reaction temperature rise to 80 ℃ continuously from 35 ℃.
Available ordinary method is separated final product.Preferably, at first with the Lewis acid hydrolysis.For example, if use the chlorinated aromatic hydrocarbons solvent,, can obtain the crystal of compound shown in the accepted way of doing sth I by slowly adding non-polar solvent and crystal seed.Temperature in the time of can reducing crystallization, and preferably with suction method the product that obtains is separated.
Separated products can be washed at filter from solvent, and is dry then, and drying is preferably carried out in 65-70 ℃, vacuum.
Formula I compound itself can make organic materials Photostabilised; In addition, hydrogen atom on-hydroxy functional group right by replacing, it also can be used for preparing 2-(2-hydroxyl-4-alkoxyl phenyl)-4, and 6-two (2, the 4-3,5-dimethylphenyl)-and the s-compound in triazine class, this compounds is known as the photostabilizer of organic materials, particularly synthetic polymer.This type of application example that is similar to the compound of formula I compound for example can be referring to US-A-3268474.
The present invention also provides the method for compound shown in a kind of intermediate formula IV for preparing in the aforesaid method
Wherein, at 0-110 ℃, in the presence of Lewis acid and at least a inertia chlorinated aromatic hydrocarbons solvent, by added compound shown in the formula III in 5-30 hour, make shown in cyanuryl chloride shown in the formula II and the formula III 1,3-dimethylbenzene reacts
Obtain compound shown in the formula IV, wherein, with respect to every mole cyanuryl chloride, lewis acidic consumption is 2.3-3.0mol, 1, and the consumption of 3-dimethylbenzene is 2.1-2.5mol; And with the formula IV compound separation that obtains.
The reaction conditions of this method and preferred embodiment are corresponding to the step a) in the single still method of the invention described above.With compound shown in the ordinary method separate type IV known in the art, for example boil off solvent, add suitable solvent and make product crystallization etc.
The following example is used for further illustrating the present invention.Except as otherwise noted, all percentage number averages by weight.
Embodiment
2-(2, the 4-dihydroxy phenyl)-4, the preparation of 6-two (2, the 4-3,5-dimethylphenyl)-s-triazine
Step a)
Stir (about 200rpm) down,, add 200g (1.50mol) aluminum chloride in the 110.7g in the 2-dichlorobenzene (0.60mol) cyanuryl chloride to being dissolved in 360g 1.In 30 minutes, will be somebody's turn to do the suspension that easily stirs then and be heated to 84-86 ℃, and under this temperature, keep 15 minutes.Under the stirring of about 200rpm, in 84-86 ℃, 4 hours, be metered into 67.9ml (58.6g, 0.55mol) m-xylene (heat release! ), then, in 1.5 hours, this suspension as far as possible constant speed is cooled to 34-36 ℃.In 6 hours, 34-36 ℃ adds another batch 101.8ml (87.95g, 0.83mol) m-xylene (heat release! ).Before reinforced the end, discharge small amount of H Cl gas, use NaOH (40%) its neutralization.After dimethylbenzene adds, with this dark brown reaction mixture that easily stirs 34-36 ℃ of restir 15 minutes.
Step b)
Be metered into 9.9g (0.09mol) Resorcinol in 1 hour in above-mentioned reaction soln, temperature still remains 34-36 ℃.Added the 9.9g Resorcinol equally in 1 hour again, temperature rises to 48 ℃ from 35 ℃ around here.In 48 ℃, 3 hours, add 29.7g Resorcinol (0.45mol) again.
In 3 hours, reaction mixture is heated to 79-81 ℃ then, and under this temperature restir 1 hour.The HCl gas that discharges during entire reaction neutralizes with 40% NaOH solution.
As described belowly carry out aftertreatment:
In 10-15 minute, under the stirring of 300-350rpm, above-mentioned warm reaction soln is added in the mixture of 750g water under the room temperature and 750g methyl iso-butyl ketone (MIBK) or methylethylketone.At 68-70 ℃ product is stirred extraction 10 minutes.After the phase-splitting, remove lower floor's water, the upper organic phase 3% salt acid treatment of 375g.With this mixture 68-70 ℃ of restir 10 minutes.Remove lower floor's water after the phase-splitting.
Boil off solvent from organic phase, the temperature in when beginning distillation is that about 104 ℃, pressure are normal pressure, and temperature is that about 130 ℃, pressure are the 150-155 millibar during end.Add 400g 1 in distillation residue, the 2-dichlorobenzene makes temperature be not less than 120 ℃.In 1 hour, be metered into 580g heptane isomers mixture then, make to keep tangible reflux state always.After adding the 200g heptane, in this solution, add crystal seed (the 1g 2-in the 20g heptane (2, the 4-dihydroxy phenyl)-4,6-two (2, the 4-3,5-dimethylphenyl)-s-triazine) continuously.After being metered into about 50% heptane, product begins to crystallize at leisure the fine acicular crystal.After heptane adds, with the thickness that obtains but the suspension that easily stirs refluxes again (110-112 ℃) 1 hour.
After this suspension was cooled to 20-22 ℃, suction filtration was at first used 500g 1,2-dichlorobenzene/heptane (1: 1), used the 400g methanol wash then, with damp product (about 300g) 65-70 ℃ of vacuum-drying.
Output: 146.5g (about 98.5% (LC))=144.3g (100%) is 60.5% based on the productive rate of cyanuryl chloride.
Claims (13)
1. 2-(2, the 4-dihydroxy phenyl)-4 shown in the preparation formula I, the method for 6-two (2, the 4-3,5-dimethylphenyl)-s-triazine
This method comprises:
A) at 0-110 ℃, in the presence of Lewis acid and at least a inertia chlorinated aromatic hydrocarbons solvent,, make shown in cyanuryl chloride shown in the formula II and the formula III 1 by in 5-30 hour, adding compound shown in the formula III, 3-dimethylbenzene reacts
Obtain compound shown in the formula IV
Wherein, with respect to every mole cyanuryl chloride, lewis acidic consumption is 2.3-3.0mol, 1, and the consumption of 3-dimethylbenzene is 2.1-2.5mol; Then
B) do not separate the formula IV compound that obtains, make itself and Resorcinol 0-100 ℃ of reaction, obtain compound shown in the formula I, wherein, with respect to every mole cyanuryl chloride, the consumption of Resorcinol is 0.5-1.0mol.
2. according to the process of claim 1 wherein, in step a), compound shown in the formula III divides 2 batches of addings.
3. according to the method for claim 2, wherein, at first add the 0.5-1.1 mole, add compound shown in the formula III of 2.0-1.0 mole then.
4. according to the method for claim 2, wherein, the temperature when adding the 1st batch is 60-110 ℃, and the temperature when adding the 2nd batch is 20-50 ℃.
5. according to the method for claim 1, wherein, in step a), in 60-110 ℃, 2-12 hour, add compound shown in the formula III of 0.5-1.1 mole, in 0-3 hour, this mixture is cooled to 20-50 ℃ then, in 20-50 ℃, 5-15 hour, adds compound shown in the 2.0-1.0 mole formula III afterwards.
6. according to the method for claim 1, wherein, in step a), in 83-87 ℃, 3.5-4.5 hour, add compound shown in the formula III of 0.85-1.0 mole, in 1.4-1.6 hour, this mixture is cooled to 33-37 ℃ then, in 33-37 ℃, 5.5-6.5 hour, adds compound shown in the 1.45-1.3 mole formula III afterwards.
7. according to the process of claim 1 wherein, at step a) and b) in use identical chlorinated aromatic hydrocarbons solvent.
8. according to the method for claim 7, wherein, at step a) and b) in use chlorobenzene or dichlorobenzene.
9. according to the process of claim 1 wherein, in step a), with respect to every mole of cyanuryl chloride, lewis acidic consumption is the 2.4-2.6 mole.
10. according to the method for claim 9, wherein, described Lewis acid is aluminum chloride or alchlor.
11. according to the method for claim 10, wherein, described Lewis acid is an aluminum chloride.
12. according to the process of claim 1 wherein, in step b), with respect to every mole of cyanuryl chloride, the consumption of Resorcinol is the 0.7-0.8 mole.
13. according to the process of claim 1 wherein, the temperature in step b) is 35-80 ℃.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH354195 | 1995-12-14 | ||
| CH3541/95 | 1995-12-14 | ||
| CH3541/1995 | 1995-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1161331A CN1161331A (en) | 1997-10-08 |
| CN1070187C true CN1070187C (en) | 2001-08-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96121532A Expired - Fee Related CN1070187C (en) | 1995-12-14 | 1996-12-12 | Process for prepn. of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-S-triazine |
Country Status (7)
| Country | Link |
|---|---|
| KR (1) | KR100484265B1 (en) |
| CN (1) | CN1070187C (en) |
| AT (1) | ATE213732T1 (en) |
| AU (1) | AU725423B2 (en) |
| BR (1) | BR9605986A (en) |
| DE (1) | DE59608792D1 (en) |
| TW (1) | TW366340B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI259182B (en) * | 1998-11-17 | 2006-08-01 | Cytec Tech Corp | Process for preparing triazines using a combination of Lewis acids with reaction promoters |
| CN118561772B (en) * | 2024-07-31 | 2024-11-15 | 山东法恩新材料科技有限公司 | One-pot synthesis of bis-resorcinol methoxyphenyl triazine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1169947B (en) * | 1958-12-24 | 1964-05-14 | Ciba Geigy | Process for the preparation of 2- (2 ', 4'-dimethylphenyl) -4, 6-dichloro-1, 3, 5-triazine or 2, 4-di- (2', 4'-dimethylphenyl) -6-chloro- 1, 3, 5-triazine |
| US3244708A (en) * | 1963-02-07 | 1966-04-05 | Ciba Ltd | Hydroxyphenyl-1, 3, 5-triazines |
| US3268474A (en) * | 1961-03-06 | 1966-08-23 | American Cyanamid Co | Polymers stabilized with orthohydroxyaryl-s-triazines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4092466A (en) * | 1976-07-19 | 1978-05-30 | Nasa | Heat resistant polymers of oxidized styrylphosphine |
-
1996
- 1996-12-03 AT AT96810845T patent/ATE213732T1/en not_active IP Right Cessation
- 1996-12-03 DE DE59608792T patent/DE59608792D1/en not_active Expired - Fee Related
- 1996-12-04 TW TW085114935A patent/TW366340B/en active
- 1996-12-06 AU AU74217/96A patent/AU725423B2/en not_active Ceased
- 1996-12-12 CN CN96121532A patent/CN1070187C/en not_active Expired - Fee Related
- 1996-12-13 KR KR1019960067059A patent/KR100484265B1/en not_active IP Right Cessation
- 1996-12-13 BR BR9605986A patent/BR9605986A/en not_active IP Right Cessation
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1169947B (en) * | 1958-12-24 | 1964-05-14 | Ciba Geigy | Process for the preparation of 2- (2 ', 4'-dimethylphenyl) -4, 6-dichloro-1, 3, 5-triazine or 2, 4-di- (2', 4'-dimethylphenyl) -6-chloro- 1, 3, 5-triazine |
| US3268474A (en) * | 1961-03-06 | 1966-08-23 | American Cyanamid Co | Polymers stabilized with orthohydroxyaryl-s-triazines |
| US3244708A (en) * | 1963-02-07 | 1966-04-05 | Ciba Ltd | Hydroxyphenyl-1, 3, 5-triazines |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59608792D1 (en) | 2002-04-04 |
| MX9606261A (en) | 1997-10-31 |
| TW366340B (en) | 1999-08-11 |
| KR100484265B1 (en) | 2005-08-10 |
| KR970042521A (en) | 1997-07-24 |
| BR9605986A (en) | 1998-09-01 |
| AU725423B2 (en) | 2000-10-12 |
| CN1161331A (en) | 1997-10-08 |
| AU7421796A (en) | 1997-06-19 |
| ATE213732T1 (en) | 2002-03-15 |
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