CN105646573A - Preparation method of environment-friendly aluminum dicyclopentylphosphinate flame retardant - Google Patents
Preparation method of environment-friendly aluminum dicyclopentylphosphinate flame retardant Download PDFInfo
- Publication number
- CN105646573A CN105646573A CN201610110526.4A CN201610110526A CN105646573A CN 105646573 A CN105646573 A CN 105646573A CN 201610110526 A CN201610110526 A CN 201610110526A CN 105646573 A CN105646573 A CN 105646573A
- Authority
- CN
- China
- Prior art keywords
- phosphinic acid
- alkali metal
- dicyclopentylphosphinate
- metal salt
- aluminum
- 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
- 239000003063 flame retardant Substances 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- FAQADBUCMODICN-UHFFFAOYSA-K tris(dicyclopentylphosphoryloxy)alumane Chemical compound C1CCC(C1)P(=O)(C2CCCC2)O[Al](OP(=O)(C3CCCC3)C4CCCC4)OP(=O)(C5CCCC5)C6CCCC6 FAQADBUCMODICN-UHFFFAOYSA-K 0.000 title abstract 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title abstract 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 39
- -1 alkali metal salt Chemical class 0.000 claims abstract description 31
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 27
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000003254 radicals Chemical class 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 25
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 19
- 230000007613 environmental effect Effects 0.000 claims description 11
- 150000001941 cyclopentenes Chemical class 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical group [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 4
- 229910000765 intermetallic Inorganic materials 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 238000007342 radical addition reaction Methods 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 239000001117 sulphuric acid Substances 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- GBYRUWDSIOQIAQ-UHFFFAOYSA-N dicyclopentylphosphinic acid Chemical compound C1CCCC1P(=O)(O)C1CCCC1 GBYRUWDSIOQIAQ-UHFFFAOYSA-N 0.000 abstract 8
- BINGNNPZDKBIOW-UHFFFAOYSA-N [PH2](OC1CCCC1)=O Chemical compound [PH2](OC1CCCC1)=O BINGNNPZDKBIOW-UHFFFAOYSA-N 0.000 abstract 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 1
- 239000012466 permeate Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/303—Cycloaliphatic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Fireproofing Substances (AREA)
Abstract
The invention relates to a preparation method of an environment-friendly aluminum dicyclopentylphosphinate flame retardant. The preparation method comprises steps as follows: a free radical source is added to phosphinic acid, monoalkylphosphinate or an alkali metal water solution of phosphinic acid and monoalkylphosphinate at the certain temperature under the pressure, and hypo acid free radicals are formed; the hypo acid free radicals are added to cyclopentene, and mono-cyclopentylphosphinate and dicyclopentylphosphinate or alkali metal salt of mono-cyclopentylphosphinate and dicyclopentylphosphinate are obtained; tail gas is recycled; mono-cyclopentylphosphinate or alkali metal salt of mono-cyclopentylphosphinate has a reflux reaction, and dicyclopentylphosphinate or alkali metal salt of dicyclopentylphosphinate is obtained; dicyclopentylphosphinate or alkali metal salt of dicyclopentylphosphinate permeates and is separated, and dicyclopentylphosphinate or dicyclopentylphosphinate alkali metal salt is obtained; dicyclopentylphosphinate or dicyclopentylphosphinate alkali metal salt and an aluminum compound react, and aluminum dicyclopentylphosphinate is obtained; aluminum dicyclopentylphosphinate is filtered, washed and dried in vacuum at the temperature of 130 DEG C. The preparation method has the benefits as follows: the fire retardant has more excellent temperature resistance due to the high-temperature stability of cyclopentyl.
Description
Technical field
The present invention relates to the technical field of fire-retardant FRW, the preparation method particularly relating to a kind of environmental protection bicyclopentyl phosphinic acid aluminum fire retardant.
Background technology
Along with developing rapidly of industrial economy, the macromolecular material application in the industry such as plastics, rubber and synthetic fibers are more and more extensive, but macromolecular material is generally inflammable or combustible, burning initiation fire can cause substantial amounts of life and property loss, therefore in macromolecular material, add fire retardant, make synthetic material have the characteristics such as flame retardancy, self-extinguishment and smoke elimination, be current problem demanding prompt solution.
Summary of the invention
The technical problem to be solved is: the preparation method providing a kind of environmental protection bicyclopentyl phosphinic acid aluminum fire retardant, solve common in macromolecular material add fire retardant easily environment and production cost is higher, purity is low and the problem of low conversion rate.
The present invention solves that problem set forth above be the technical scheme is that
The preparation method of a kind of environmental protection bicyclopentyl phosphinic acid aluminum fire retardant, comprises the following steps:
A. it is 70��90 DEG C and pressure is 1��3 standard atmosphere pressure in temperature, after any one in hypophosphorous acid or monoalkylphosphinic acids or its hypophosphites alkali metal is dissolved at a certain temperature in water and add radical source, thus forming the free radical of the stronger subacid of activity;
B. in the free radical addition of the subacid of gained in above-mentioned steps a) to cyclopentenes molecule, single, double cyclopenta phosphinic acid or its alkali metal salt will be obtained;
C. the tail gas recycle in above-mentioned steps b) is recycled;
D. by monocycle amyl group phosphinic acid in above-mentioned steps b) or its alkali metal salt, undertaken being obtained by reacting Bicvclopentyl phosphinic acid or its alkali metal salt by refluxing;
E. the bicyclopentyl phosphinic acid or the bicyclopentyl phosphinic acid alkali metal salt that purify are obtained by osmosis after the Bicvclopentyl phosphinic acid obtained in above-mentioned steps b), step d) or its alkali metal salt being separated;
F. the metallic compound of the bicyclopentyl phosphinic acid obtained in above-mentioned steps e) or bicyclopentyl phosphinic acid alkali metal salt and aluminum is reacted, generate bicyclopentyl phosphinic acid aluminum;
G. the bicyclopentyl phosphinic acid aluminum that obtains in above-mentioned steps f) is filtered, with hot wash, and at 130 DEG C of temperature vacuum drying.
Any one aqueous solution alkali-metal to hypophosphorous acid or monoalkylphosphinic acids or its hypophosphites is heated to 70��90 DEG C by described step a).
Described step b) is 70��90 DEG C and pressure is that 1��3 standard atmosphere pressure is progressively added dropwise to cyclopentenes, reaction backflow 7��10 hours by dosing pump in temperature.
In described step f), the pH value with sulphuric acid adjustment bicyclopentyl phosphinic acid or bicyclopentyl phosphinic acid alkali metal salt is 2.8��3.2.
In described step f), the metallic compound of aluminum is aluminum sulfate.
The beneficial effects of the present invention is: 1, the high-temperature stability of cyclopenta makes the heat resistance of this fire retardant more excellent. 2, course of reaction does not use organic solvent, more environmental protection. 3, in course of reaction the material such as unreacted cyclopentenes, monocycle amyl group phosphinic acid or its alkali metal salt can recycling, this preparation method achieves raw-material 100% and utilizes. 4, the bicyclopentyl phosphinic acid aluminum fire retardant conversion ratio that this preparation method prepares is high, purity is high, and does not produce garbage in whole technical process.
Detailed description of the invention
Embodiments of the invention are further illustrated below.
Embodiment one
It is 80 DEG C and pressure is 1 standard atmosphere pressure in temperature, to equipped with agitator, the 1L four-hole boiling flask of constant voltage air intake installation and gas circulating reflux condenser adds 40g sodium hypophosphite, the stirring that is dissolved in water is heated to 80 DEG C, cyclopentenes is dripped after sodium hypophosphite is completely dissolved, add 0.2g catalyst and 0.8g radical initiator, heating is stopped after reacting 8 hours, add the dilute sulfuric acid that mass fraction is 30% and regulate pH value to 3.0, again the aluminum sulfate solution that 125g mass fraction is 30% configured uniformly is added drop-wise in this solution at room temperature 3 hours, then it is rapidly heated to 90 DEG C and is incubated 1 hour, cooling, filter, drying obtains product 67.2g, yield is 62.6%, product is carried out phosphorus nuclear-magnetism detection, recording bicyclopentyl phosphinic acid aluminum content is 99.16%, cyclopenta phosphinic acid aluminum is 0.56%, other is 0.28%, reaction raffinate adds recycling in next reaction again, comprehensive yield reaches 100%, wherein the content of bicyclopentyl phosphinic acid aluminum reaches more than 99%.
Embodiment two
It is 75 DEG C and pressure is 2 standard atmospheres pressures in temperature, to equipped with agitator, the 1L four-hole boiling flask of constant voltage air intake installation and gas circulating reflux condenser adds 40g sodium hypophosphite, stirring is heated to 75 DEG C, cyclopentenes is dripped after sodium hypophosphite is completely dissolved, add 0.2g catalyst and 0.8g radical initiator, heating is stopped after reacting 9 hours, add the dilute sulfuric acid that mass fraction is 30% and regulate pH value to 3.0, it is that 30% aluminum sulfate solution is uniformly added drop-wise in this solution at room temperature 3 hours by the 125g mass fraction configured again, then it is rapidly heated to 90 DEG C of insulations 1 hour, cooling, filter, drying obtains product 65.8g, yield is 61.5%, product is carried out phosphorus nuclear-magnetism detection, recording bicyclopentyl phosphinic acid aluminum content is 99.54%, cyclopenta phosphinic acid aluminum is 0.33%, other is 0.13%, reaction raffinate adds recycling in next reaction again, comprehensive yield reaches 100%, wherein the content of bicyclopentyl phosphinic acid aluminum reaches more than 99%.
Having the beneficial effects that of this detailed description of the invention: 1, the high-temperature stability of cyclopenta makes the heat resistance of this fire retardant more excellent. 2, course of reaction does not use organic solvent, more environmental protection. 3, in course of reaction the material such as unreacted cyclopentenes, monocycle amyl group phosphinic acid or its alkali metal salt can recycling, this preparation method achieves raw-material 100% and utilizes. 4, the bicyclopentyl phosphinic acid aluminum fire retardant conversion ratio that this preparation method prepares is high, purity is high, and does not produce garbage in whole technical process.
Specific embodiments of the invention are not construed as limiting the invention, the analog structure of every employing present invention and change, all in protection scope of the present invention.
Claims (5)
1. the preparation method of an environmental protection bicyclopentyl phosphinic acid aluminum fire retardant, it is characterised in that comprise the following steps:
A. it is 70��90 DEG C and pressure is 1��3 standard atmosphere pressure in temperature, after any one in hypophosphorous acid or monoalkylphosphinic acids or its hypophosphites alkali metal is dissolved at a certain temperature in water and add radical source, thus forming the free radical of the stronger subacid of activity;
B. in the free radical addition of the subacid of gained in above-mentioned steps a) to cyclopentenes molecule, single, double cyclopenta phosphinic acid or its alkali metal salt will be obtained;
C. the tail gas recycle in above-mentioned steps b) is recycled;
D. by monocycle amyl group phosphinic acid in above-mentioned steps b) or its alkali metal salt, undertaken being obtained by reacting Bicvclopentyl phosphinic acid or its alkali metal salt by refluxing;
E. the bicyclopentyl phosphinic acid or the bicyclopentyl phosphinic acid alkali metal salt that purify are obtained by osmosis after the Bicvclopentyl phosphinic acid obtained in above-mentioned steps b), step d) or its alkali metal salt being separated;
F. the metallic compound of the bicyclopentyl phosphinic acid obtained in above-mentioned steps e) or bicyclopentyl phosphinic acid alkali metal salt and aluminum is reacted, generate bicyclopentyl phosphinic acid aluminum;
G. the bicyclopentyl phosphinic acid aluminum that obtains in above-mentioned steps f) is filtered, with hot wash, and at 130 DEG C of temperature vacuum drying.
2. the preparation method of a kind of environmental protection bicyclopentyl phosphinic acid aluminum fire retardant as claimed in claim 1, it is characterised in that: any one aqueous solution alkali-metal to hypophosphorous acid or monoalkylphosphinic acids or its hypophosphites is heated to 70��90 DEG C by described step a).
3. the preparation method of a kind of environmental protection bicyclopentyl phosphinic acid aluminum fire retardant as claimed in claim 1, it is characterized in that: described step b) is 70��90 DEG C and pressure is that 1��3 standard atmosphere pressure is progressively added dropwise to cyclopentenes, reaction backflow 7��10 hours by dosing pump in temperature.
4. the preparation method of a kind of environmental protection bicyclopentyl phosphinic acid aluminum fire retardant as claimed in claim 1, it is characterised in that: in described step f), the pH value with sulphuric acid adjustment bicyclopentyl phosphinic acid or bicyclopentyl phosphinic acid alkali metal salt is 2.8��3.2.
5. the preparation method of a kind of environmental protection bicyclopentyl phosphinic acid aluminum fire retardant as claimed in claim 1, it is characterised in that: in described step f), the metallic compound of aluminum is aluminum sulfate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610110526.4A CN105646573A (en) | 2016-02-29 | 2016-02-29 | Preparation method of environment-friendly aluminum dicyclopentylphosphinate flame retardant |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610110526.4A CN105646573A (en) | 2016-02-29 | 2016-02-29 | Preparation method of environment-friendly aluminum dicyclopentylphosphinate flame retardant |
Publications (1)
Publication Number | Publication Date |
---|---|
CN105646573A true CN105646573A (en) | 2016-06-08 |
Family
ID=56492823
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610110526.4A Pending CN105646573A (en) | 2016-02-29 | 2016-02-29 | Preparation method of environment-friendly aluminum dicyclopentylphosphinate flame retardant |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105646573A (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103073574A (en) * | 2012-09-19 | 2013-05-01 | 广州金凯新材料有限公司 | Preparation method of dialkyl phosphinic acid and salt thereof |
CN103172670A (en) * | 2013-03-04 | 2013-06-26 | 广州金凯新材料有限公司 | Monoalkyl/dialkyl phosphinate and preparation method thereof |
CN104693237A (en) * | 2015-03-26 | 2015-06-10 | 洪湖市一泰科技有限公司 | Preparing method for dialkyl phosphinate salt |
-
2016
- 2016-02-29 CN CN201610110526.4A patent/CN105646573A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103073574A (en) * | 2012-09-19 | 2013-05-01 | 广州金凯新材料有限公司 | Preparation method of dialkyl phosphinic acid and salt thereof |
CN103172670A (en) * | 2013-03-04 | 2013-06-26 | 广州金凯新材料有限公司 | Monoalkyl/dialkyl phosphinate and preparation method thereof |
CN104693237A (en) * | 2015-03-26 | 2015-06-10 | 洪湖市一泰科技有限公司 | Preparing method for dialkyl phosphinate salt |
Non-Patent Citations (1)
Title |
---|
王颖等: "二环烷基次膦酸的合成与表征", 《化学试剂》 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104370743B (en) | The preparation method of plasticizer triethylene glycol two tricaprylates | |
CN111440357A (en) | All-bio-based flame retardant, flame-retardant P L A composite material and preparation method thereof | |
CN110643018B (en) | Bio-based flame-retardant epoxy resin containing nitrogen and phosphorus structures and preparation method thereof | |
CN103435653B (en) | A kind of preparation method of hexaphenoxycyclotriphosphazene | |
CN103183704B (en) | A kind of preparation method of three (tribromoneoamyl alcohol base) phosphoric acid ester | |
CN109053389B (en) | Synthetic method of 2,4, 6-tribromophenyl allyl ether | |
CN105646573A (en) | Preparation method of environment-friendly aluminum dicyclopentylphosphinate flame retardant | |
CN105482096B (en) | A kind of reactive phosphorus flame retardant and preparation method thereof | |
CN107501526B (en) | DOPO type epoxy resin curing agent and preparation method thereof | |
CN103121887A (en) | Preparation method of 1,3-indandione compounds | |
CN102936302A (en) | Preparation method of chlorinated polyvinyl chloride resin | |
CN105523982A (en) | Method for preparing tert-butyl hydroperoxide | |
CN109575076B (en) | Preparation of phosphorus-containing bismaleimide and application of phosphorus-containing bismaleimide in flame-retardant epoxy resin | |
CN103739624B (en) | The synthetic method of aluminum diethylphosphinate | |
CN111423673A (en) | Heat-resistant and high-temperature-resistant PVC (polyvinyl chloride) power tube and preparation method thereof | |
CN105622610A (en) | Method for preparing xanthine compound | |
CN112661721A (en) | New process for synthesizing 2-mercaptobenzothiazole zinc salt by solvent method | |
CN110835422A (en) | Carbazole type phosphate flame retardant and preparation method thereof | |
CN112778356B (en) | One-pot synthesis process of tri (tribromoneopentyl) phosphate flame retardant | |
CN115124425B (en) | 3, 5-dibromo-4-hydroxybenzoic acid dimer, synthesis method and application thereof | |
CN113292597B (en) | Method for preparing triethyl phosphate compound by recovering sodium diethylphosphate and ethyl chloride | |
CN114621088B (en) | Preparation method of diethyl terephthalamide | |
CN107417533B (en) | Dimethyl isophthalate and process for producing the same | |
CN108383870B (en) | Glufosinate-ammonium salt intermediate and synthetic method of glufosinate-ammonium salt | |
CN110590540A (en) | Flame retardant 2, 5-dibromo terephthalic acid and production process thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160608 |
|
RJ01 | Rejection of invention patent application after publication |