CN102391124A - 一种光稳定剂3,5-二叔丁基-4-羟基苯甲酸正十六酯的制备方法 - Google Patents
一种光稳定剂3,5-二叔丁基-4-羟基苯甲酸正十六酯的制备方法 Download PDFInfo
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- CN102391124A CN102391124A CN2011103076189A CN201110307618A CN102391124A CN 102391124 A CN102391124 A CN 102391124A CN 2011103076189 A CN2011103076189 A CN 2011103076189A CN 201110307618 A CN201110307618 A CN 201110307618A CN 102391124 A CN102391124 A CN 102391124A
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- Prior art keywords
- tert
- butyl
- hydroxybenzoic acid
- positive
- hexadecyl ester
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- 238000000034 method Methods 0.000 title abstract description 12
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 title abstract 4
- 239000004611 light stabiliser Substances 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 claims abstract description 24
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000035484 reaction time Effects 0.000 claims abstract description 11
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 47
- -1 hexadecyl ester Chemical class 0.000 claims description 35
- 125000002252 acyl group Chemical group 0.000 claims description 24
- 239000012320 chlorinating reagent Substances 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000005292 vacuum distillation Methods 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 229910019213 POCl3 Inorganic materials 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 description 10
- 238000010792 warming Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN 201110307618 CN102391124B (zh) | 2011-10-12 | 2011-10-12 | 一种光稳定剂3,5-二叔丁基-4-羟基苯甲酸正十六酯的制备方法 |
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CN 201110307618 CN102391124B (zh) | 2011-10-12 | 2011-10-12 | 一种光稳定剂3,5-二叔丁基-4-羟基苯甲酸正十六酯的制备方法 |
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CN102391124A true CN102391124A (zh) | 2012-03-28 |
CN102391124B CN102391124B (zh) | 2013-10-16 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659600A (zh) * | 2012-05-14 | 2012-09-12 | 南通惠康国际企业有限公司 | 一种光稳定剂3,5-二叔丁基-4-羟基苯甲酸2,6-二叔丁基苯酯的制备方法 |
CN103819399A (zh) * | 2013-12-27 | 2014-05-28 | 青岛首和金海制药有限公司 | 一种生产高纯度甘露六烟酯的方法 |
CN105481759A (zh) * | 2016-01-19 | 2016-04-13 | 如东金康泰化学有限公司 | 一种光稳定剂n,n,-双-(2,2,6,6-四甲基-4-哌啶基)间苯二甲酰胺的合成方法 |
CN105541613A (zh) * | 2015-12-31 | 2016-05-04 | 浙江师范大学 | 3,5-二叔丁基-4-羟基苯甲酸正十六烷基酯的制备方法 |
CN110862318A (zh) * | 2019-10-24 | 2020-03-06 | 甘肃省化工研究院有限责任公司 | 一种叔丁基取代羟基苯甲酸酯的制备方法 |
CN114230460A (zh) * | 2021-12-31 | 2022-03-25 | 江苏极易新材料有限公司 | 一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法 |
CN116217397A (zh) * | 2022-12-28 | 2023-06-06 | 甘肃省化工研究院有限责任公司 | 一种提高苯甲酸酯类紫外线吸收剂透过率的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3681431A (en) * | 1970-02-06 | 1972-08-01 | Ciba Geigy Corp | N-OCTADECYL 3,5-DI-t-BUTYL-4-HYDROXYBENZOATE |
US4128726A (en) * | 1977-12-22 | 1978-12-05 | American Cyanamid Company | Process for the preparation of aryl esters of 3,5-di-t-butyl-4-hydroxybenzoic acid |
US4528395A (en) * | 1983-08-15 | 1985-07-09 | American Cyanamid Co. | Process for esterifying 3,5-di-tert-butyl-4-hydroxybenzoic acid |
WO2006054446A1 (ja) * | 2004-11-22 | 2006-05-26 | Adeka Corporation | ヒドロキシベンゾエート化合物の製造方法 |
-
2011
- 2011-10-12 CN CN 201110307618 patent/CN102391124B/zh not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3681431A (en) * | 1970-02-06 | 1972-08-01 | Ciba Geigy Corp | N-OCTADECYL 3,5-DI-t-BUTYL-4-HYDROXYBENZOATE |
US4128726A (en) * | 1977-12-22 | 1978-12-05 | American Cyanamid Company | Process for the preparation of aryl esters of 3,5-di-t-butyl-4-hydroxybenzoic acid |
US4528395A (en) * | 1983-08-15 | 1985-07-09 | American Cyanamid Co. | Process for esterifying 3,5-di-tert-butyl-4-hydroxybenzoic acid |
WO2006054446A1 (ja) * | 2004-11-22 | 2006-05-26 | Adeka Corporation | ヒドロキシベンゾエート化合物の製造方法 |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659600A (zh) * | 2012-05-14 | 2012-09-12 | 南通惠康国际企业有限公司 | 一种光稳定剂3,5-二叔丁基-4-羟基苯甲酸2,6-二叔丁基苯酯的制备方法 |
CN103819399A (zh) * | 2013-12-27 | 2014-05-28 | 青岛首和金海制药有限公司 | 一种生产高纯度甘露六烟酯的方法 |
CN105541613A (zh) * | 2015-12-31 | 2016-05-04 | 浙江师范大学 | 3,5-二叔丁基-4-羟基苯甲酸正十六烷基酯的制备方法 |
CN105481759A (zh) * | 2016-01-19 | 2016-04-13 | 如东金康泰化学有限公司 | 一种光稳定剂n,n,-双-(2,2,6,6-四甲基-4-哌啶基)间苯二甲酰胺的合成方法 |
CN105481759B (zh) * | 2016-01-19 | 2018-09-14 | 如东金康泰化学有限公司 | 一种光稳定剂n,n,-双-(2,2,6,6-四甲基-4-哌啶基)间苯二甲酰胺的合成方法 |
CN110862318A (zh) * | 2019-10-24 | 2020-03-06 | 甘肃省化工研究院有限责任公司 | 一种叔丁基取代羟基苯甲酸酯的制备方法 |
CN110862318B (zh) * | 2019-10-24 | 2022-05-13 | 甘肃省化工研究院有限责任公司 | 一种叔丁基取代羟基苯甲酸酯的制备方法 |
CN114230460A (zh) * | 2021-12-31 | 2022-03-25 | 江苏极易新材料有限公司 | 一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法 |
WO2023123569A1 (zh) * | 2021-12-31 | 2023-07-06 | 江苏极易新材料有限公司 | 一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法 |
CN116217397A (zh) * | 2022-12-28 | 2023-06-06 | 甘肃省化工研究院有限责任公司 | 一种提高苯甲酸酯类紫外线吸收剂透过率的方法 |
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