CN103508938A - N,n’-二(2,2,6,6-四甲基-4-哌啶基)-1,3-苯二甲酰胺的制备方法 - Google Patents
N,n’-二(2,2,6,6-四甲基-4-哌啶基)-1,3-苯二甲酰胺的制备方法 Download PDFInfo
- Publication number
- CN103508938A CN103508938A CN201310110901.1A CN201310110901A CN103508938A CN 103508938 A CN103508938 A CN 103508938A CN 201310110901 A CN201310110901 A CN 201310110901A CN 103508938 A CN103508938 A CN 103508938A
- Authority
- CN
- China
- Prior art keywords
- tetramethyl
- benzenedicarboxamide
- piperidyl
- bis
- preparation
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- OYNOCRWQLLIRON-UHFFFAOYSA-N 1-n,3-n-bis(2,2,6,6-tetramethylpiperidin-4-yl)benzene-1,3-dicarboxamide Chemical compound C1C(C)(C)NC(C)(C)CC1NC(=O)C1=CC=CC(C(=O)NC2CC(C)(C)NC(C)(C)C2)=C1 OYNOCRWQLLIRON-UHFFFAOYSA-N 0.000 title abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 48
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003960 organic solvent Substances 0.000 claims abstract description 25
- 239000012065 filter cake Substances 0.000 claims abstract description 21
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 claims abstract description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 13
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 4
- 238000001556 precipitation Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 238000005406 washing Methods 0.000 claims description 22
- 238000009413 insulation Methods 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- -1 isophthaloyl chlorine Chemical compound 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 23
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000005119 centrifugation Methods 0.000 description 14
- 239000012452 mother liquor Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000002386 leaching Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- 239000004677 Nylon Substances 0.000 description 6
- 229920001778 nylon Polymers 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- 238000007670 refining Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- RFTJIJFLPFVJKR-UHFFFAOYSA-N 2,2,5,6-tetramethylpiperidin-4-amine Chemical compound CC1NC(C)(C)CC(N)C1C RFTJIJFLPFVJKR-UHFFFAOYSA-N 0.000 description 1
- CWNZRFQFYLHOND-UHFFFAOYSA-N CN1C(CC(CC1(C)C)N)C Chemical compound CN1C(CC(CC1(C)C)N)C CWNZRFQFYLHOND-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method 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
- C07D211/06—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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201310110901.1A CN103508938B (zh) | 2013-03-30 | 2013-03-30 | N,n’-二(2,2,6,6-四甲基-4-哌啶基)-1,3-苯二甲酰胺的制备方法 |
Applications Claiming Priority (1)
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CN201310110901.1A CN103508938B (zh) | 2013-03-30 | 2013-03-30 | N,n’-二(2,2,6,6-四甲基-4-哌啶基)-1,3-苯二甲酰胺的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN103508938A true CN103508938A (zh) | 2014-01-15 |
CN103508938B CN103508938B (zh) | 2015-07-08 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104829650A (zh) * | 2015-05-15 | 2015-08-12 | 湘潭大学 | 一种具有热稳定性的受阻胺光稳定剂及其制备方法 |
CN104974075A (zh) * | 2015-08-07 | 2015-10-14 | 新秀化学(烟台)有限公司 | 一种n, n-二(2,2,6,6-四甲基-4-哌啶基) -1,3-苯二甲酰胺的制备方法 |
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 |
WO2017005413A1 (de) * | 2015-07-03 | 2017-01-12 | Clariant International Ltd | Polymeradditiv und verfahren zu seiner herstellung |
CN106905517A (zh) * | 2017-04-20 | 2017-06-30 | 福建中锦新材料有限公司 | 一种用于纺丝的聚酰胺6及其制造方法 |
US10336699B2 (en) | 2017-08-02 | 2019-07-02 | Sunshow (Yantai) Specialty Chemical Company Limited | Method for synthesizing N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,3-benzenedicarboxamide |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1000967A1 (en) * | 1998-11-16 | 2000-05-17 | Clariant Finance (BVI) Limited | Improved polyester polymers |
CN1671664A (zh) * | 2002-08-19 | 2005-09-21 | 科莱恩有限公司 | 聚合物用稳定剂的制备方法 |
CN1675300A (zh) * | 2002-08-07 | 2005-09-28 | 西巴特殊化学品控股有限公司 | 用于聚丙烯的β-成核剂、光稳定剂 |
CN102516157A (zh) * | 2011-12-07 | 2012-06-27 | 浙江大学 | 一种受阻酚/受阻胺分子内复合型抗氧剂的合成方法 |
-
2013
- 2013-03-30 CN CN201310110901.1A patent/CN103508938B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1000967A1 (en) * | 1998-11-16 | 2000-05-17 | Clariant Finance (BVI) Limited | Improved polyester polymers |
CN1675300A (zh) * | 2002-08-07 | 2005-09-28 | 西巴特殊化学品控股有限公司 | 用于聚丙烯的β-成核剂、光稳定剂 |
CN1671664A (zh) * | 2002-08-19 | 2005-09-21 | 科莱恩有限公司 | 聚合物用稳定剂的制备方法 |
CN102516157A (zh) * | 2011-12-07 | 2012-06-27 | 浙江大学 | 一种受阻酚/受阻胺分子内复合型抗氧剂的合成方法 |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104829650A (zh) * | 2015-05-15 | 2015-08-12 | 湘潭大学 | 一种具有热稳定性的受阻胺光稳定剂及其制备方法 |
WO2017005413A1 (de) * | 2015-07-03 | 2017-01-12 | Clariant International Ltd | Polymeradditiv und verfahren zu seiner herstellung |
CN107820488A (zh) * | 2015-07-03 | 2018-03-20 | 科莱恩塑料和涂料有限公司 | 聚合物添加剂及其制备方法 |
US10745353B2 (en) | 2015-07-03 | 2020-08-18 | Clariant Plastics & Coatings Ltd | Polymer additive and a method for the production thereof |
CN107820488B (zh) * | 2015-07-03 | 2021-07-02 | 科莱恩塑料和涂料有限公司 | 聚合物添加剂及其制备方法 |
CN104974075A (zh) * | 2015-08-07 | 2015-10-14 | 新秀化学(烟台)有限公司 | 一种n, n-二(2,2,6,6-四甲基-4-哌啶基) -1,3-苯二甲酰胺的制备方法 |
WO2017024608A1 (zh) * | 2015-08-07 | 2017-02-16 | 新秀化学(烟台)有限公司 | 一种尼龙耐候助剂的制备方法 |
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 |
CN106905517A (zh) * | 2017-04-20 | 2017-06-30 | 福建中锦新材料有限公司 | 一种用于纺丝的聚酰胺6及其制造方法 |
US10336699B2 (en) | 2017-08-02 | 2019-07-02 | Sunshow (Yantai) Specialty Chemical Company Limited | Method for synthesizing N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,3-benzenedicarboxamide |
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Publication number | Publication date |
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CN103508938B (zh) | 2015-07-08 |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
C56 | Change in the name or address of the patentee | ||
CP03 | Change of name, title or address |
Address after: 264006, No. 3-5, Yantai District, Yantai Development Zone, Shandong, Hengshan Road, 5 Patentee after: Yantai Rui long new materials Co.,Ltd. Address before: 264006 No. 58 Haibin Road, Yantai Development Zone, Shandong, Yantai, China Patentee before: YANTAI RUILONG CHEMICAL TECHNOLOGY Co.,Ltd. |
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Effective date of registration: 20160311 Address after: 264006 No. 7, No. 9, North Beijing Road, Yantai economic and Technological Development Zone, Shandong, Yantai, 3 Patentee after: SUNSHOW (YANTAI) SPECIALTY CHEMICAL Co.,Ltd. Address before: No. 3-5, Hengshan Road District, Yantai Development Zone, Shandong, Yantai, China Patentee before: Yantai Rui long new materials Co.,Ltd. |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-phthalamide Effective date of registration: 20170111 Granted publication date: 20150708 Pledgee: Yantai Yinqiao financing Company limited by guarantee Pledgor: SUNSHOW (YANTAI) SPECIALTY CHEMICAL Co.,Ltd. Registration number: 2017370000001 |
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Date of cancellation: 20180118 Granted publication date: 20150708 Pledgee: Yantai Yinqiao financing Company limited by guarantee Pledgor: SUNSHOW (YANTAI) SPECIALTY CHEMICAL Co.,Ltd. Registration number: 2017370000001 |
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Effective date of registration: 20200715 Address after: 124000 West C14, South GONGMAO Road, Shuangtaizi District, Panjin City, Liaoning Province Patentee after: Panjin Xinxiu New Material Co.,Ltd. Address before: No.3, No.7, No.9, Beijing North Road, Yantai Economic and Technological Development Zone Patentee before: SUNSHOW (YANTAI) SPECIALTY CHEMICAL Co.,Ltd. |