CN113993838A - 二乙氨基羟基苯甲酰基苯甲酸己酯的制造方法 - Google Patents
二乙氨基羟基苯甲酰基苯甲酸己酯的制造方法 Download PDFInfo
- Publication number
- CN113993838A CN113993838A CN202080042581.9A CN202080042581A CN113993838A CN 113993838 A CN113993838 A CN 113993838A CN 202080042581 A CN202080042581 A CN 202080042581A CN 113993838 A CN113993838 A CN 113993838A
- Authority
- CN
- China
- Prior art keywords
- chemical formula
- hexyl benzoate
- diethylamino hydroxybenzoyl
- hydroxybenzoyl hexyl
- diethylamino
- 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
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- 229960001630 diethylamino hydroxybenzoyl hexyl benzoate Drugs 0.000 title claims abstract description 52
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 52
- FDATWRLUYRHCJE-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O FDATWRLUYRHCJE-UHFFFAOYSA-N 0.000 title claims abstract 10
- 239000002245 particle Substances 0.000 claims abstract description 37
- 239000000126 substance Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- -1 chloro, bromo, iodo, methanesulfonyl Chemical group 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- OHXXFKGUPZOOFC-UHFFFAOYSA-N 2-benzoyl-4-(diethylamino)-3-hydroxybenzoic acid Chemical compound CCN(CC)C1=CC=C(C(O)=O)C(C(=O)C=2C=CC=CC=2)=C1O OHXXFKGUPZOOFC-UHFFFAOYSA-N 0.000 claims description 3
- FQZUJLKQOVWKRT-UHFFFAOYSA-N hexyl hydrogen sulfite Chemical compound CCCCCCOS(O)=O FQZUJLKQOVWKRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- OOHTWBUKWQKKEE-UHFFFAOYSA-N [6-(diethylamino)-6-hydroxy-7-oxo-7-phenylheptyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)C(O)(N(CC)CC)CCCCCOC(=O)C1=CC=CC=C1 OOHTWBUKWQKKEE-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 14
- 239000003610 charcoal Substances 0.000 description 12
- 239000005711 Benzoic acid Substances 0.000 description 11
- 235000010233 benzoic acid Nutrition 0.000 description 11
- 239000008213 purified water Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002981 blocking agent Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012754 barrier agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 2
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- QUJIVWINNPEYAS-UHFFFAOYSA-N dihexyl sulfate Chemical compound CCCCCCOS(=O)(=O)OCCCCCC QUJIVWINNPEYAS-UHFFFAOYSA-N 0.000 description 2
- BXVQCOZKKYBAQR-UHFFFAOYSA-N dihexyl sulfite Chemical compound CCCCCCOS(=O)OCCCCCC BXVQCOZKKYBAQR-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- URIRDRHUUFRHAS-UHFFFAOYSA-N hexyl methanesulfonate Chemical compound CCCCCCOS(C)(=O)=O URIRDRHUUFRHAS-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 230000009759 skin aging Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- ZMJOVJSTYLQINE-UHFFFAOYSA-N Dichloroacetylene Chemical compound ClC#CCl ZMJOVJSTYLQINE-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010053615 Thermal burn Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- IVQOVYWBHRSGJI-UHFFFAOYSA-N hexyl 4-methylbenzenesulfonate Chemical compound CCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 IVQOVYWBHRSGJI-UHFFFAOYSA-N 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 231100000405 induce cancer Toxicity 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/34—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having amino groups and esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20190126502 | 2019-10-11 | ||
| KR10-2019-0126502 | 2019-10-11 | ||
| KR10-2019-0161828 | 2019-12-06 | ||
| KR1020190161828A KR102179649B1 (ko) | 2019-10-11 | 2019-12-06 | 디에틸아미노하이드록시벤조일헥실벤조에이트의 제조 방법 |
| PCT/KR2020/002959 WO2021071033A1 (ko) | 2019-10-11 | 2020-03-02 | 디에틸아미노하이드록시벤조일헥실벤조에이트의 제조 방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113993838A true CN113993838A (zh) | 2022-01-28 |
Family
ID=69154356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080042581.9A Pending CN113993838A (zh) | 2019-10-11 | 2020-03-02 | 二乙氨基羟基苯甲酰基苯甲酸己酯的制造方法 |
Country Status (6)
| Country | Link |
|---|---|
| JP (3) | JP7195351B2 (ja) |
| KR (3) | KR102179649B1 (ja) |
| CN (1) | CN113993838A (ja) |
| DE (1) | DE112020004927T5 (ja) |
| TW (1) | TW202122369A (ja) |
| WO (1) | WO2021071033A1 (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010615A (zh) * | 2022-07-14 | 2022-09-06 | 四川沃肯精细化工有限公司 | 一种二乙氨基羟苯甲酰基苯甲酸正己酯的制备方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102179649B1 (ko) * | 2019-10-11 | 2020-11-18 | (주)에이에스텍 | 디에틸아미노하이드록시벤조일헥실벤조에이트의 제조 방법 |
| KR20220147622A (ko) * | 2020-02-27 | 2022-11-03 | 바스프 에스이 | 2-(4'-디에틸아미노-2'-히드록시벤조일)벤조산 헥실 에스테르를 단리시키는 방법 |
| CN112479890B (zh) * | 2020-11-27 | 2023-09-26 | 苏州亚科科技股份有限公司 | 一种硝基化合物的制备方法 |
| CN116096701A (zh) * | 2020-12-18 | 2023-05-09 | 巴斯夫欧洲公司 | 用于获得结晶二乙氨基羟基苯甲酰苯甲酸己酯的方法 |
| CN112679393A (zh) * | 2020-12-31 | 2021-04-20 | 江苏科本药业有限公司 | 索非布韦杂质的制备方法 |
| CN114149339B (zh) * | 2021-12-28 | 2023-01-31 | 黄冈美丰化工科技有限公司 | 一种紫外线吸收剂、组合物、化妆品及配制化妆品的工艺 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4935543A (en) * | 1988-05-20 | 1990-06-19 | Takeda Chemical Industries, Ltd. | Physiologically active substance tan-931, its derivatives, their production and use |
| CN1653035A (zh) * | 2002-05-15 | 2005-08-10 | 巴斯福股份公司 | 制备2－(4－n,n－二烷基氨基－2－羟基苯甲酰基)苯甲酸酯的方法 |
| CN101675029A (zh) * | 2007-05-02 | 2010-03-17 | 巴斯夫欧洲公司 | 2-(4-n,n-二乙基氨基-2-羟基苯甲酰基)苯甲酸正己基酯的结晶方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0733709A (ja) * | 1993-07-27 | 1995-02-03 | Tanabe Seiyaku Co Ltd | シュウ酸モノエステル化合物の製法 |
| KR100236388B1 (ko) * | 1995-11-28 | 1999-12-15 | 성재갑 | 신규한 고분자 자외선 차단제 및 그 제조방법 |
| DE19917906A1 (de) | 1999-04-20 | 2000-10-26 | Basf Ag | Verwendung von aminosubstituierten Hydroxybenzophenonen als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
| DE10011317A1 (de) | 2000-03-10 | 2001-09-13 | Basf Ag | Verwendung von aminosubstituierten Hydroxybenzophenonen als Lichtschutzmittel und Stabilisatoren für nicht lenbendes organisches Material |
| DE10342861A1 (de) | 2003-09-15 | 2005-04-21 | Basf Ag | Pulverförmiger Zubereitungen, enthaltend eine Mischung von 2,4,6-Trianilino-p-(carbo-2'-ethylhexyl-1'-oxi)-1,3,5-triazin und Diethylamino-hydroxybenzoyl-hexyl-benzoat |
| CA2725199A1 (en) * | 2008-05-21 | 2009-11-26 | The Regents Of The University Of Colorado | Ionic liquids and methods for using the same |
| JP4299878B1 (ja) | 2008-10-06 | 2009-07-22 | 株式会社パラエルモサ | 化粧料 |
| CN102665652B (zh) | 2009-12-24 | 2014-07-16 | 花王株式会社 | 水凝胶颗粒 |
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| TWI724049B (zh) * | 2015-11-04 | 2021-04-11 | 日商大塚製藥股份有限公司 | 碘美醇的創新製備法及結晶化法 |
| KR102179649B1 (ko) * | 2019-10-11 | 2020-11-18 | (주)에이에스텍 | 디에틸아미노하이드록시벤조일헥실벤조에이트의 제조 방법 |
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- 2020-03-02 JP JP2020573548A patent/JP7195351B2/ja active Active
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115010615A (zh) * | 2022-07-14 | 2022-09-06 | 四川沃肯精细化工有限公司 | 一种二乙氨基羟苯甲酰基苯甲酸正己酯的制备方法 |
| CN115010615B (zh) * | 2022-07-14 | 2023-12-08 | 四川沃肯精细化工有限公司 | 一种二乙氨基羟苯甲酰基苯甲酸正己酯的制备方法 |
Also Published As
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| JP2022188148A (ja) | 2022-12-20 |
| WO2021071033A1 (ko) | 2021-04-15 |
| KR102179649B1 (ko) | 2020-11-18 |
| JP2022188149A (ja) | 2022-12-20 |
| WO2021071033A9 (ko) | 2021-10-14 |
| KR20200002720A (ko) | 2020-01-08 |
| KR102439837B1 (ko) | 2022-09-05 |
| JP2021533088A (ja) | 2021-12-02 |
| KR20210071804A (ko) | 2021-06-16 |
| TW202122369A (zh) | 2021-06-16 |
| KR102357197B1 (ko) | 2022-02-03 |
| KR20210142575A (ko) | 2021-11-25 |
| JP7195351B2 (ja) | 2022-12-23 |
| DE112020004927T5 (de) | 2022-06-23 |
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