CN1044901C - Technology for producing ultraviolet absorbent in single process - Google Patents
Technology for producing ultraviolet absorbent in single process Download PDFInfo
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- CN1044901C CN1044901C CN94106768A CN94106768A CN1044901C CN 1044901 C CN1044901 C CN 1044901C CN 94106768 A CN94106768 A CN 94106768A CN 94106768 A CN94106768 A CN 94106768A CN 1044901 C CN1044901 C CN 1044901C
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/008—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with tri- or tetrahalomethyl compounds
Abstract
The present invention relates to a technology for producing an ultraviolet absorbent UV-531 in a single process. Resorcine and n-octyl alcohol are used as raw materials, the present invention is characterized in that trichlorotoluene is also adopted as a raw material, and according to the procedures of the raw materials, a condensation reaction, water washing, secondary crystallization and the finished product 531, the three raw materials are added into a reaction kettle; temperature is increased to 70 DEG C to 90 DEG C, tri-n-butylamine is added as a catalyst; the temperature is continuously increased to 135 DEG C to 145 DEG C, and thiourea dioxide and potassium iodide are added as catalysts; the temperature is increased to 150 DEG C to 170 DEG C and maintained for 10 to 18 hours, and after the whole condensation reaction is finished, the product UV-531 is produced. The chemical reaction principle of the product UV-531 is disclosed in the specifications.
Description
The invention belongs to preparation method's (comprising temperature control and prescription and catalyzer) of ultraviolet absorbent UV-531.
The chemical name of UV-531: Octabenzone (2-HYDROXYL-4-N-OCTOXYLBENZOPHENONE), molecular formula C
21H
28O
3Structural formula:
This product can strong absorption 240～340 be received the micron ultraviolet ray.It and synthetic materials intermiscibility are good, and volatility is little, and resistance to draw, anti-fibering all are better than other benzophenone class UV light absorber.And with thermo-stabilizer, oxidation inhibitor etc. good synergistic is arranged, to the color of each colour product do not have influence, nontoxic, be dissolved in organism such as benzene, ethanol, Virahol, water insoluble, of many uses.
Ultraviolet absorbent UV-531 is widely used in the synthetic materialss such as various plastics, synthon, rubber resin, synthetic glass, coating and petroleum products, particularly to indispensable photostabilizer in polypropylene, polyvinyl chloride, synthetic rubber, unsaturated polyester, ABS resin, Resins, epoxy, resol, paraffin, makeup and food, the plastics, the plastic industry of China is annual to be needed from external import more than 1000 tons.UV-531 is that the U.S. was developed in the seventies initial stage and goes into operation in 68 years, Japan, Belgium produce the UV-531 product at late nineteen seventies in succession, and Long March chemical plant, China Nanjing is stopped production because of the three-step approach cost is too high after American Cyanamid Co.'s introduction three-step approach is produced 10 tons of pilot production lines per year in the eighties by the Ministry of Chemical Industry mid-term.
Traditional three-step production process, promptly respectively with synthetic UV-0 intermediates such as Resorcinols, with synthetic chloro octanes such as n-Octanols, and then generate UV-531 with the reaction of UV-O intermediate and chloro octane, solvent and catalyzer etc. all need be made with extra care, be separated, reclaim to each step operation, this synthetic route is long, and equipment is many, the energy consumption cost height.
The object of the present invention is to provide a kind of preparation method of new UV light absorber Octabenzone, it is short that it has synthetic route, the advantage that facility investment is few, energy consumption cost is low.
The preparation method of UV light absorber Octabenzone of the present invention, with Resorcinol and n-Octanol is raw material, it is characterized in that also adopting the raw material trichlorotoluene zotrichloride, three kinds of raw materials are added in the reactor, be warming up to 70 ℃～90 ℃, add the catalyzer Tributylamine, continue to be warmed up to 100 ℃～130 ℃ insulations 3～5 hours, be warmed up to 135 ℃～145 ℃ then and add catalyzer thiourea peroxide, potassiumiodide, be warmed up to 150 ℃～170 ℃ insulations 10～18 hours again, condensation reaction finishes and generates the UV-531 product, and its chemical principle is:
The kind of raw materials used in the above-mentioned production technique, catalyzer and the temperature and the soaking time that add catalyzer for twice are vital, and it concerns that can this condensation reaction carry out feasible and smoothly, must strictly observe.
Above-mentioned ultraviolet absorbent UV-531 one-step method production process, the part by weight of its raw material and catalyst levels should be controlled in the following scope (unit: part) and make it yield and reach more than 60% (yield=Resorcinol weight and make 531 weight)
Resorcinol 60-100 n-Octanol 140-257
Trichlorotoluene zotrichloride 93-157 Tributylamine 2.9-11.4
Potassiumiodide 2.9-11.4 thiourea peroxide 1.4-11.4
Ultraviolet absorbent in single process preparation method of the present invention because three kinds of raw materials and catalyzer all add in the reactor, therefore only uses the equipment of traditional three-step approach 1/3, significantly reduced facility investment, to build the factory that produces 20 tons per year is example, and three-step approach needs 1,800,000 yuan of facility investments, and single stage method only is 600,000 yuan, and factory building takes up an area of only about 1/3, the operational path of single stage method is short in addition, and simple to operate, energy consumption cost is low, product cost is low, 20,000 yuan per ton.
Accompanying drawing is a process flow diagram of the present invention.
Below the present invention will be further described with embodiment.
The preparation method of UV light absorber Octabenzone, raw material has three kinds---and Resorcinol, n-Octanol, trichlorotoluene zotrichloride, three kinds of raw materials and catalyzer be synthetic UV-531 product in same reactor, and chemical reaction is as follows:
Embodiment:
At first 100 parts of Resorcinols, 210 parts of n-Octanols, 125 parts of disposable putting in the condensation reaction still shown in the drawings of trichlorotoluene zotrichloride are reacted (claiming again to treat different things alike), in one hour, be warming up to 70 ℃～90 ℃ and add 7 parts of catalyzer Tributylamines, continue to be warmed up to 100 ℃～130 ℃, be incubated 3～5 hours, add 7 parts of two kinds of catalyzer potassiumiodides, 6.5 parts of thiourea peroxides simultaneously, be warmed up to 150 ℃～170 ℃ insulations 10～18 hours then in 4 hours, last whole condensation reaction just finishes.Generated the UV-531 product this moment, then by washing, primary crystallization, secondary crystal, drying, packing warehouse-in.The share of catalyst material all can guarantee yield more than 60% in above-mentioned scope, existing raw material and catalyst consumption and yield are exemplified below:
Example 1 example 2 examples 3
Resorcinol 100 100 100
N-Octanol 140 180 257
Trichlorotoluene zotrichloride 93 135 157
Tributylamine 2.9 5 11.4
Potassiumiodide 2.9 6 11.4
Thiourea peroxide 1.4 6.5 11.4
Finished product 531 70 100 70
Yield 70% 100% 70%
Preparation method of the present invention adopts advanced one-step synthesis process, i.e. resorcinol, n-octyl alcohol and three There is next time synthetic UV-531 product in chlorotoluene at catalyst, and technology is simple, be easy to control, cost is low, Equipment investment is compared with traditional three-steps process only has 1/3, thereby has economized out the synthetic and refining of two intermediates Separate, its product quality meets Japanese rice field Co., Ltd. and Long March chemical plant, Nanjing ultraviolet absorbent UV-531 Company standard. The three wastes are littler than traditional three-steps process in addition.
Claims (2)
1, the preparation method of UV light absorber Octabenzone, with Resorcinol and n-Octanol is raw material, it is characterized in that adopting the raw material trichlorotoluene zotrichloride, three kinds of raw materials are added in the reactor, be warming up to 70 ℃～90 ℃, add the catalyzer Tributylamine, continue to be warmed up to 135 ℃～145 ℃ and add catalyzer thiourea peroxide, potassiumiodide, be warmed up to 150 ℃～170 ℃ insulations 10～18 hours again, condensation reaction finishes and generates the UV-531 product, and its chemical principle is:
The part by weight of raw material and catalyzer is as follows: (unit serving)
Resorcinol 60-100 n-Octanol 140-257
Trichlorotoluene zotrichloride 93-157 Tributylamine 2.9-11.4
Potassiumiodide 2.9-11.4 thiourea peroxide 1.4-11.4
2, preparation method as claimed in claim 1, it is characterized in that adding thiourea peroxide, potassiumiodide after, in 4 hours, be warmed up to 150 ℃～170 ℃ the insulation 10～18 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94106768A CN1044901C (en) | 1994-06-21 | 1994-06-21 | Technology for producing ultraviolet absorbent in single process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94106768A CN1044901C (en) | 1994-06-21 | 1994-06-21 | Technology for producing ultraviolet absorbent in single process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1118777A CN1118777A (en) | 1996-03-20 |
| CN1044901C true CN1044901C (en) | 1999-09-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94106768A Expired - Fee Related CN1044901C (en) | 1994-06-21 | 1994-06-21 | Technology for producing ultraviolet absorbent in single process |
Country Status (1)
| Country | Link |
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| CN (1) | CN1044901C (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101456802B (en) * | 2008-12-03 | 2011-08-24 | 荆门市美丰化工有限公司 | Process for producing ultraviolet absorbent UV-531 by one-step method |
| CN103319935A (en) * | 2013-06-26 | 2013-09-25 | 关锦池 | Hydroxyalkyl amide curing agent composition used for powder coating |
| CN103342634A (en) * | 2013-07-15 | 2013-10-09 | 黑龙江大学 | Synthesis method of 4, 4'-dihydroxy benzophenone |
| CN109456233A (en) * | 2018-10-23 | 2019-03-12 | 襄阳金达成精细化工有限公司 | A kind of preparation method of ultraviolet absorbing agent UV-284 |
| CN109406472B (en) * | 2018-10-29 | 2021-08-24 | 太原师范学院 | Fluorescent carbon nanoparticles and detection of Ni2+Method for ionic and glycine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352921A (en) * | 1963-09-20 | 1967-11-14 | Ici Ltd | Process for making 2-hydroxy-4 or 5-alkylbenzophenones using sodium iodide |
| US3396186A (en) * | 1965-05-25 | 1968-08-06 | Universal Oil Prod Co | Boron acid ester of phenone |
| US4302606A (en) * | 1980-05-23 | 1981-11-24 | Gaf Corporation | 2-Hydroxy,alkoxy,methylolbenzophenone intermediate compounds for the manufacture of improved copolymerizable ultraviolet light absorber compounds |
-
1994
- 1994-06-21 CN CN94106768A patent/CN1044901C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352921A (en) * | 1963-09-20 | 1967-11-14 | Ici Ltd | Process for making 2-hydroxy-4 or 5-alkylbenzophenones using sodium iodide |
| US3396186A (en) * | 1965-05-25 | 1968-08-06 | Universal Oil Prod Co | Boron acid ester of phenone |
| US4302606A (en) * | 1980-05-23 | 1981-11-24 | Gaf Corporation | 2-Hydroxy,alkoxy,methylolbenzophenone intermediate compounds for the manufacture of improved copolymerizable ultraviolet light absorber compounds |
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| Publication number | Publication date |
|---|---|
| CN1118777A (en) | 1996-03-20 |
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