CN115477607A - 一种光稳定剂中间体及其制备方法 - Google Patents
一种光稳定剂中间体及其制备方法 Download PDFInfo
- Publication number
- CN115477607A CN115477607A CN202211261555.2A CN202211261555A CN115477607A CN 115477607 A CN115477607 A CN 115477607A CN 202211261555 A CN202211261555 A CN 202211261555A CN 115477607 A CN115477607 A CN 115477607A
- Authority
- CN
- China
- Prior art keywords
- light stabilizer
- stabilizer intermediate
- reaction
- preparation
- crude product
- 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
- 239000004611 light stabiliser Substances 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000012043 crude product Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 15
- GDJQNGMJGMABLV-UHFFFAOYSA-N 1,3,3,4-tetramethylpiperidin-2-one Chemical compound CC1CCN(C)C(=O)C1(C)C GDJQNGMJGMABLV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- 239000012065 filter cake Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
- 230000003321 amplification Effects 0.000 abstract description 2
- 239000012267 brine Substances 0.000 abstract description 2
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229940027987 antiseptic and disinfectant phenol and derivative Drugs 0.000 description 6
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
Abstract
本发明公开了一种光稳定剂中间体及其制备方法;制备:S1、将四甲基哌啶酮、对甲苯磺酸以及原料A溶于有机溶剂中,获得混合物;S2、对所述混合物进行加热反应;S3、反应后冷却,然后向体系中加入碱液,搅拌,过滤,获得粗品;S4、将所述的粗品重结晶,获得光稳定剂中间体。本发明提出的光稳定剂中间体的制备方法,其产物收率相较于现有的制备工艺得到了大幅提升,反应时间缩短,反应操作简便,同时有效的减少了大量浓盐酸的使用,减少了大量废盐水的产生,更绿色环保,更易放大生产。
Description
技术领域
本发明涉及有机合成技术领域,具体涉及一种光稳定剂中间体及其制备方法。
背景技术
4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物中含有四甲基哌啶的受阻胺的特殊结构,其结构为光稳定剂(光老化剂)的主要作用结构。所以4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物是光稳定剂(4-(4'-羟基苯基)-2,2,6,6-四甲基哌啶及其衍生物)的重要中间体。Jerzy Zakrzewski在2010年发现了一种新型的具有活性官能团的氮氧化物,其可用于修饰具有生物活性的合成或天然分子或大分子,4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物也是其中最重要的中间体;4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物现有文献报道的合成方法是:将四甲基哌啶酮、苯酚在浓盐酸中在70℃下反应10小时后用苯进行沉化,再进行碱洗得粗品;然后将粗品进行脱氯化氢操作后,再进行重结晶制得产品,其产物收率在52%左右。
然而,现有的这种制备方法存在反应时间较长,产物收率较低等缺陷,同时该方法还使用了大量的浓盐酸、苯等,因而导致该方法不易放大生产、并且容易产生大量的高盐废水,不环保。
发明内容
本发明的目的在于:针对现有4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物制备工艺中存在的反应时间长、产物收率低、该方法不适用于大规模生产以及针对该方法不环保、容易产生大量高盐废水等等问题,而提出了一种制备光稳定剂中间体(4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基))的新方法,本发明提出的这种方法是一种简便的制备方法,能有效解决上述背景技术工艺中存在的诸多问题。
为解决上述问题,本发明是通过如下技术方案实现的:
一种光稳定剂中间体的制备方法,其特征在于,该方法包括如下步骤:
S1、将四甲基哌啶酮、对甲苯磺酸以及原料A溶于有机溶剂中,获得混合物;其中:所述的原料A具有式(1)所示的结构通式:式中:R1、R2分别选自以下基团:氢、碳原子数为1-11的烷基、卤素、取代苯基、取代萘基、取代杂环中的一种或两种;
S2、对所述混合物进行加热反应;
S3、反应后冷却,然后向体系中加入碱液,搅拌,过滤,获得粗品;
进一步的,一种光稳定剂中间体的制备方法:步骤S1中所述四甲基哌啶酮、对甲苯磺酸以及原料A之间的摩尔比为1:(2-4):(0.1-0.2);所述的四甲基哌啶酮与所述有机溶剂的摩尔体积比为0.5-1.5mol/L。
进一步的,一种光稳定剂中间体的制备方法:步骤S1中所述的有机溶剂为甲苯。
进一步的,一种光稳定剂中间体的制备方法:步骤S1中取代基团为氢、氟、氯、溴、碘、甲基、甲氧基中的一种或二种以上。
进一步的,一种光稳定剂中间体的制备方法:步骤S2、将所述混合物在搅拌条件下进行加热反应;其中加热温度为110-130℃,反应时间为4-6小时。
进一步的,一种光稳定剂中间体的制备方法:步骤S3、反应后冷却至室温,然后向体系中加入碱液,搅拌0.5-2小时,然后过滤,获得的滤饼为粗品;其中所述的碱液与所述有机溶剂的体积比为1:(1-3)。
进一步的,一种光稳定剂中间体的制备方法:步骤S3中所述的碱液为质量分数10-30wt%的碳酸钠溶液。
进一步的,一种光稳定剂中间体的制备方法:步骤S4中获得的光稳定剂中间体为粉末状。
一种光稳定剂中间体,其特征在于,采用上述的制备方法制得。
提供一种光稳定剂中间体的一种用途:可将上述的制备方法制得的光稳定剂中间体用于制备光稳定剂,且所述的光稳定剂为4-(4'-羟基苯基)-2,2,6,6-四甲基哌啶及其衍生物。
具体的,本发明制备的光稳定剂中间体为4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物,其具有式(2)所示的结构通式,4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物中含有四甲基哌啶的受阻胺的特殊结构,其结构为光稳定剂的主要作用结构,所以4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚及衍生物是光稳定剂4-(4'-羟基苯基)-2,2,6,6-四甲基哌啶的重要中间体。
本发明的有益效果:
本发明使用四甲基哌啶酮、苯酚或其衍生物、对甲苯磺酸(TsOH)作为原料,甲苯作为反应溶剂,在110-130℃下反应4-6小时后冷却至室温加入溶液中搅拌后粗品析出,抽滤后进行结晶制备产物,其收率能达到79.5%左右。本发明提出的制备方法,其产物收率相较于现有的工艺(现有工艺产物收率在52%左右)得到了大幅提升,反应时间缩短,反应操作简便,同时有效的减少了大量浓盐酸的使用,减少了大量废盐水的产生,更绿色环保,更易放大生产。
具体实施方式
下面将结合具体实施例,对本发明的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明的一部分实施例,而不是全部的实施例。以下对至少一个示例性实施例的描述实际上仅仅是说明性的,决不作为对本发明及其应用或使用的任何限制。基于本发明中的实施例,本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
一种光稳定剂中间体的制备方法,其特征在于,该方法包括如下步骤:
S1、在500毫升的三口烧瓶中加入200毫升的甲苯,然后将0.2mol的四甲基哌啶酮、0.02mol的对甲苯磺酸(TsOH)以及0.6mol的苯酚(原料A)溶于甲苯中,获得混合物;其中:所述的原料A具有式(1)所示的结构通式:式中:R1、R2均为氢;
S2、将所得混合物在搅拌条件下加热至120℃,反应6小时;
S3、反应后冷却至室温,然后向反应体系中加入100毫升质量分数20wt%的碳酸钠溶液,搅拌1小时,然后过滤,滤饼即为产物粗品;S4、将所得的粗品重结晶,获得约36.4g的光稳定剂中间体;所得的光稳定剂中间体为4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚白色粉末,其具有式(2)所示的结构通式:式中:R1、R2均为氢。
产物收率为79.36%,熔点为190.2-191.6℃,HPLC纯度为98.3%。1H NMR(300MHz,DMSO-d6):δ9.37(s,1H,OH),7.26–7.12(m,2H,ArH),6.78–6.63(m,2H,ArH),5.85(s,1H,(CH3)2CCH=),2.10(d,J=0.9Hz,2H,CH2),1.48–1.20(m,1H,NH),1.13(d,J=15.9Hz,12H,4×CH3)。ESI-MS m/z:实测值:232.15[M+1]+;计算值:232.16[C15H21NO+1]+.
上述实施例1的合成过程如下所示:
实施例2
一种光稳定剂中间体的制备方法,其特征在于,该方法包括如下步骤:
S1、在500毫升的三口烧瓶中加入200毫升的甲苯,然后将0.2mol的四甲基哌啶酮、0.02mol的对甲苯磺酸(TsOH)以及0.6mol的邻甲酚(原料A)溶于甲苯中,获得混合物;;
S2、将所得混合物在搅拌条件下加热至120℃,反应6小时;
S3、反应后冷却至室温,然后向反应体系中加入100毫升质量分数20wt%的碳酸钠溶液,搅拌1小时,然后过滤,滤饼即为产物粗品;
S4、将所得的粗品重结晶,获得约35.8g的光稳定剂中间体;所得的光稳定剂中间体为2-甲基-4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚白色粉末,其产物收率约为73.1%。
实施例3
一种光稳定剂中间体的制备方法,其特征在于,该方法包括如下步骤:
S1、在500毫升的三口烧瓶中加入200毫升的甲苯,然后将0.2mol的四甲基哌啶酮、0.02mol的对甲苯磺酸(TsOH)以及0.6mol的2-氯苯(原料A)溶于甲苯中,获得混合物;;
S2、将所得混合物在搅拌条件下加热至120℃,反应6小时;
S3、反应后冷却至室温,然后向反应体系中加入100毫升质量分数20wt%的碳酸钠溶液,搅拌1小时,然后过滤,滤饼即为产物粗品;
S4、将所得的粗品重结晶,获得约37.2g的光稳定剂中间体;所得的光稳定剂中间体为2-氯基-4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚淡黄色粉末,其产物收率约为70.1%。
实施例1-3的区别在于:原料A的不同,其余制备条件相同。
实施例4
一种光稳定剂中间体的制备方法,其特征在于,该方法包括如下步骤:
S1、在500毫升的三口烧瓶中加入200毫升的甲苯,然后将0.2mol的四甲基哌啶酮、0.03mol的对甲苯磺酸(TsOH)以及0.4mol的苯酚(原料A)溶于甲苯中,获得混合物;
S2、将所得混合物在搅拌条件下加热至110℃,反应5小时;
S3、反应后冷却至室温,然后向反应体系中加入100毫升质量分数30wt%的碳酸钠溶液,搅拌2小时,然后过滤,滤饼即为产物粗品;
S4、将所得的粗品重结晶,获得光稳定剂中间体;所得的光稳定剂中间体为4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚白色粉末。
实施例5
一种光稳定剂中间体的制备方法,其特征在于,该方法包括如下步骤:
S1、在500毫升的三口烧瓶中加入200毫升的甲苯,然后将0.2mol的四甲基哌啶酮、0.04mol的对甲苯磺酸(TsOH)以及0.8mol的苯酚(原料A)溶于甲苯中,获得混合物;
S2、将所得混合物在搅拌条件下加热至130℃,反应4小时;
S3、反应后冷却至室温,然后向反应体系中加入100毫升质量分数25wt%的碳酸钠溶液,搅拌0.5小时,然后过滤,滤饼为产物粗品;
S4、将所得的粗品重结晶,获得光稳定剂中间体;所得的光稳定剂中间体为4-(1,2,3,6-四氢-2,2,6,6-四甲基-4-哌啶基)-苯酚白色粉末。
由上述的实施例可以看出本发明提供的方法其产物收率要明显高于现有的合成工艺,同时在本发明的方法中不需要使用浓盐酸,在其生产过程中不会产生大量的高盐废水,绿色环保。
上述为本发明的较佳实施例仅用于解释本发明,并不用于限定本发明。凡由本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之中。
Claims (9)
2.根据权利要求1所述的一种光稳定剂中间体的制备方法,其特征在于,步骤S1中所述四甲基哌啶酮、对甲苯磺酸以及原料A之间的摩尔比为1:(2-4):(0.1-0.2);所述的四甲基哌啶酮与所述有机溶剂的摩尔体积比为0.5-1.5mol/L。
3.根据权利要求1所述的一种光稳定剂中间体的制备方法,其特征在于,步骤S1中所述的有机溶剂为甲苯。
4.根据权利要求1所述的一种光稳定剂中间体的制备方法,其特征在于,步骤S1中取代基团为氢、氟、氯、溴、碘、甲基、甲氧基中的一种或二种以上。
5.根据权利要求1所述的一种光稳定剂中间体的制备方法,其特征在于,步骤S2、将所述混合物在搅拌条件下进行加热反应;其中加热温度为110-130℃,反应时间为4-6小时。
6.根据权利要求1所述的一种光稳定剂中间体的制备方法,其特征在于,步骤S3、反应后冷却至室温,然后向体系中加入碱液,搅拌0.5-2小时,然后过滤,获得的滤饼为粗品;其中所述的碱液与所述有机溶剂的体积比为1:(1-3)。
7.根据权利要求1或6所述的一种光稳定剂中间体的制备方法,其特征在于,步骤S3中所述的碱液为质量分数10-30wt%的碳酸钠溶液。
8.根据权利要求1所述的一种光稳定剂中间体的制备方法,其特征在于,步骤S4中获得的光稳定剂中间体为粉末状。
9.一种光稳定剂中间体,其特征在于,采用权利要求1-8任一项所述的制备方法制得。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211261555.2A CN115477607A (zh) | 2022-10-14 | 2022-10-14 | 一种光稳定剂中间体及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211261555.2A CN115477607A (zh) | 2022-10-14 | 2022-10-14 | 一种光稳定剂中间体及其制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN115477607A true CN115477607A (zh) | 2022-12-16 |
Family
ID=84395960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211261555.2A Pending CN115477607A (zh) | 2022-10-14 | 2022-10-14 | 一种光稳定剂中间体及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115477607A (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3847930A (en) * | 1971-11-30 | 1974-11-12 | Ciba Geigy Corp | Hydroxyaryl-tetramenthyl-dehydropiperidines |
WO2004006923A1 (en) * | 2002-07-12 | 2004-01-22 | Glaxo Group Limited | Aryl piperidine derivatives as inducers of ldl-receptor expression for the treatment of hypercholesterolemia |
CN104447792A (zh) * | 2007-03-09 | 2015-03-25 | 赛诺菲-安万特股份有限公司 | 取代的二氢和四氢噁唑并嘧啶酮及其制备和用途 |
-
2022
- 2022-10-14 CN CN202211261555.2A patent/CN115477607A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3847930A (en) * | 1971-11-30 | 1974-11-12 | Ciba Geigy Corp | Hydroxyaryl-tetramenthyl-dehydropiperidines |
US4038280A (en) * | 1971-11-30 | 1977-07-26 | Ciba-Geigy Corporation | Hydroxyaryl-tetramethyl-piperidines |
WO2004006923A1 (en) * | 2002-07-12 | 2004-01-22 | Glaxo Group Limited | Aryl piperidine derivatives as inducers of ldl-receptor expression for the treatment of hypercholesterolemia |
CN104447792A (zh) * | 2007-03-09 | 2015-03-25 | 赛诺菲-安万特股份有限公司 | 取代的二氢和四氢噁唑并嘧啶酮及其制备和用途 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101993407B (zh) | 用于制备西洛多辛的吲哚啉化合物及其制备方法 | |
US9499507B2 (en) | Method for preparing 5-amino-benzoyl-benzofuran derivatives | |
CN103108869A (zh) | 制备氨基苯甲酰基苯并呋喃衍生物的方法 | |
CN109516998B (zh) | 一种巴洛沙韦中间体的合成方法 | |
RU2394026C2 (ru) | Способ оптического разделения амлодипина | |
WO2016016196A1 (en) | Novel chiral resolution of 4-aryl-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylic acid esters | |
CN115477607A (zh) | 一种光稳定剂中间体及其制备方法 | |
CZ20002665A3 (cs) | Způsob výroby /-/cis-3-hydroxy-1-methyl-4-/2,4,6-trimethoxyfenyl/-piperidinu | |
KR20090066910A (ko) | L-3-o-치환-아스코르브산의 개선된 제조방법 | |
CN113480521B (zh) | 一种苯磺酸贝他斯汀全合成方法 | |
KR100374767B1 (ko) | 개선된 암로디핀의 제조 방법 | |
CN111018782B (zh) | 9-氨基吖啶及其衍生物的制备方法 | |
CN114685376A (zh) | 嘧菌酯中间体的制备方法 | |
CN111848423B (zh) | 3-氧代环丁基氨基甲酸叔丁酯的制备方法 | |
WO2011116491A1 (zh) | 制备二苯乙醇酸去甲托品酯和其盐的方法及其中所用的中间体 | |
CN116444514A (zh) | 一种阿哌沙班乙酯化物的制备方法 | |
KR20090064456A (ko) | 트리플루오로에톡시톨루엔의 제조방법 | |
US4980505A (en) | Organic synthesis | |
CN111233864B (zh) | 一种工业化生产多索茶碱的方法 | |
CN111944199B (zh) | 一种光稳定剂及制备方法 | |
CN108658952B (zh) | 维拉佐酮盐酸盐iv型结晶的制备方法 | |
KR20040044636A (ko) | 에틸 4-(1-이미다졸일메틸)신나메이트의 정제방법 | |
EP2234975B1 (en) | Process for producing pipecolic-2-acid-2 ',6'-xylidide useful as an intermediate for the preparation of local anesthetics | |
US5247082A (en) | Imine compounds and their production | |
CN117777122A (zh) | 一种砜吡草唑的合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |