CN104031006B - 一种β-哌啶基醇的合成方法 - Google Patents

一种β-哌啶基醇的合成方法 Download PDF

Info

Publication number
CN104031006B
CN104031006B CN201410205313.0A CN201410205313A CN104031006B CN 104031006 B CN104031006 B CN 104031006B CN 201410205313 A CN201410205313 A CN 201410205313A CN 104031006 B CN104031006 B CN 104031006B
Authority
CN
China
Prior art keywords
epoxyalkane
reaction
zinc chloride
piperidines
piperidyl alcohol
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.)
Active
Application number
CN201410205313.0A
Other languages
English (en)
Other versions
CN104031006A (zh
Inventor
陈政
刘琳
吕国安
谭平平
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shandong Lanmeng Anti Corrosion Technology Co ltd
Original Assignee
Shandong Blue Union Anti-Corrosion Polytron Technologies Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shandong Blue Union Anti-Corrosion Polytron Technologies Inc filed Critical Shandong Blue Union Anti-Corrosion Polytron Technologies Inc
Priority to CN201410205313.0A priority Critical patent/CN104031006B/zh
Publication of CN104031006A publication Critical patent/CN104031006A/zh
Application granted granted Critical
Publication of CN104031006B publication Critical patent/CN104031006B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/02—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in air or gases by adding vapour phase inhibitors

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

本发明公开了一种β‑哌啶基醇的合成方法，采用哌啶和环氧烷烃进行反应，通过添加催化剂氯化锌控制环氧烷烃的开环，使反应容易进行；合成物具有多活性吸附中心，能够改善阳极极化性能，抑制腐蚀作用，属于阳极型缓蚀剂。

Description

一种β - 哌啶基醇的合成方法
技术领域
本发明涉及防锈添加剂合成技术领域，尤指一种β-哌啶基醇的合成方法。
背景技术
气相防锈是应用气相缓蚀剂技术进行腐蚀防护的一门科学，气相缓蚀剂在常温能够持续缓慢的气化、挥发出来的缓蚀气体吸附在裸露的金属表面，形成一个到两个分子厚的稳定保护膜，该保护膜能有效的防止氧气、湿气等环境气氛对金属的腐蚀，由于气相缓蚀剂是持续挥发，能够在密闭空间始终处于“饱和”状态，因而可达到长期、稳定、优良的防锈效果。目前气相防锈产品存在的主要应用形态有：将气相缓蚀剂粉末直接用雾化方式喷在金属件表面后密封；用气相防锈液喷淋、涂刷或浸泡后晾干、密封；用气相防锈纸、气相防锈膜/袋包装后金属件后密封；将气相缓蚀剂制成片状、锭状、丸状，用挂袋的方式放置在容器或塑料袋中； 将经气相缓蚀剂处理过的缓冲或衬垫材料与金属件放在一起后密封；将气相缓蚀剂混入树脂中，制成各种适合需要的包装容器，将金属件置于其中密封。中国气相防锈技术与先进国家相比，还存在着产品品种少、应用覆盖面不广的问题，因此，应加大推广先进技术，同时加强气相防锈剂的研究开发。
发明内容
本发明的目的在于提供一种β-哌啶基醇的合成方法。
本发明的技术解决方案是：以甲苯为溶剂，氯化锌为催化剂，哌啶（Ⅱ）与环氧烷烃（Ⅰ）进行加热回流反应，生成一种β-哌啶基醇，反应完成后，减压蒸馏除去溶剂和未反应物，纯化产物，得无色液体，具体包含以下步骤：
1)．以甲苯为溶剂，氯化锌为催化剂，搅拌条件下，向哌啶（Ⅱ）中缓慢加入环氧烷烃（Ⅰ），在90℃～100℃回流反应8～10小时，生成β-哌啶基醇（Ⅲ），反应完成后，减压蒸馏除去溶剂和未反应物，其主要化学反应为：
2)．产物经凝胶色谱柱经行纯化，用体积比为的40﹕60的丙酮-乙酸乙酯进行洗脱2～3次，得无色液体β-哌啶基醇。
其中，式中R为氢或碳原子数为1～3的烷基，优选氢和甲基。
进一步的是，所述的哌啶、环氧烷烃和氯化锌的摩尔比为1﹕0.9～1.0﹕0.15～0.2。
所述的甲苯，其用量为哌啶用量的2～3倍。
本发明一种二环己胺基-2-丁醇的合成方法，其特点和优点是：采用哌啶和环氧烷烃进行反应，通过添加催化剂氯化锌控制环氧烷烃的开环，使反应容易进行；合成物具有多活性吸附中心，能够改善阳极极化性能，抑制腐蚀作用，属于阳极型缓蚀剂。
具体实施方式
实施例1
在装有搅拌装置、回流冷凝装置和温度计的四口瓶中，加入85克甲苯，加入9.5克氯化锌和34克哌啶，搅拌条件下，缓慢加入20.9克环氧丙烷，在90℃～95℃回流反应9小时，生成β-哌啶基醇，反应完成后，减压蒸馏除去溶剂和未反应物，产物经凝胶色谱柱经行纯化，用体积比为的40﹕60的丙酮-乙酸乙酯进行洗脱2次，得无色液体β-哌啶基醇。
实施例2
在装有搅拌装置、回流冷凝装置和温度计的四口瓶中，加入74克甲苯，加入9克氯化锌和37克哌啶，搅拌条件下，缓慢加入29.8克环氧丁烷，在95℃～100℃回流反应10小时，生成β-哌啶基醇，反应完成后，减压蒸馏除去溶剂和未反应物，产物经凝胶色谱柱经行纯化，用体积比为的40﹕60的丙酮-乙酸乙酯进行洗脱2次，得无色液体β-哌啶基醇。
实施例3
在装有搅拌装置、回流冷凝装置和温度计的四口瓶中，加入93克甲苯，加入9.9克氯化锌和31克哌啶，搅拌条件下，缓慢加入21克环氧丙烷，在90℃～100℃回流反应8小时，生成β-哌啶基醇，反应完成后，减压蒸馏除去溶剂和未反应物，产物经凝胶色谱柱经行纯化，用体积比为的40﹕60的丙酮-乙酸乙酯进行洗脱3次，得无色液体β-哌啶基醇。
以上所述，实施方式仅仅是对本发明的优选实施方式进行描述，并非对本发明的范围进行限定，在不脱离本发明技术的精神的前提下，本领域工程技术人员对本发明的技术方案作出的各种变形和改进，均应落入本发明的权利要求书确定的保护范围内。

Claims (1)

1.一种β-哌啶基醇的合成方法，其特征是：具体包含以下步骤：
1)．以甲苯为溶剂，氯化锌为催化剂，搅拌条件下，向哌啶（Ⅱ）中缓慢加入环氧烷烃（Ⅰ），在90℃～100℃回流反应8～10小时，生成β-哌啶基醇（Ⅲ），反应完成后，减压蒸馏除去溶剂和未反应物，其主要化学反应为：
式中R为氢或碳原子数为1～3的烷基；
2)．产物经凝胶色谱柱经行纯化，用体积比为的40﹕60的丙酮-乙酸乙酯进行洗脱2～3次，得无色液体β-哌啶基醇；
其中，所述的哌啶、环氧烷烃和氯化锌的摩尔比为1﹕0.9～1.0﹕0.15～0.2。
CN201410205313.0A 2014-05-16 2014-05-16 一种β-哌啶基醇的合成方法 Active CN104031006B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410205313.0A CN104031006B (zh) 2014-05-16 2014-05-16 一种β-哌啶基醇的合成方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201410205313.0A CN104031006B (zh) 2014-05-16 2014-05-16 一种β-哌啶基醇的合成方法

Publications (2)

Publication Number Publication Date
CN104031006A CN104031006A (zh) 2014-09-10
CN104031006B true CN104031006B (zh) 2017-02-08

Family

ID=51462027

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410205313.0A Active CN104031006B (zh) 2014-05-16 2014-05-16 一种β-哌啶基醇的合成方法

Country Status (1)

Country Link
CN (1) CN104031006B (zh)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102459173A (zh) * 2009-06-08 2012-05-16 巴斯夫欧洲公司 位阻胺稳定剂
CN102516095A (zh) * 2011-11-18 2012-06-27 江苏博特新材料有限公司 含多元氨基醇类化合物、其制备方法及应用

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102459173A (zh) * 2009-06-08 2012-05-16 巴斯夫欧洲公司 位阻胺稳定剂
CN102516095A (zh) * 2011-11-18 2012-06-27 江苏博特新材料有限公司 含多元氨基醇类化合物、其制备方法及应用

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Regioselective Ring Opening in Epoxides Under the Action of Amines in Water Medium;A.G. Talybov, et al;《Russian Journal of General Chemistry》;20101231;第80卷(第9期);第1820页，第1821页第2栏第2、4段 *
Zinc-catalyzed aminolysis of epoxides;L. Durán Pachón et al.;《Tetrahedron Letters》;20031231;第44卷;第6025-6027页 *

Also Published As

Publication number Publication date
CN104031006A (zh) 2014-09-10

Similar Documents

Publication Publication Date Title
Sohrin et al. Control of Ligand Field Strength through Intra-and Interligand Contact. Octahedral Iron (II) Poly (pyrazolyl) borate Complexes
CN103408454A (zh) 一种酰肼类化合物的制备方法
IL275283B1 (en) A process for the production of layers containing metal
CN104031006B (zh) 一种β-哌啶基醇的合成方法
Penger et al. Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines
CN106008401A (zh) 一种n-甲酰胺类化合物的制备方法
AU2021217956A1 (en) Antimicrobial compounds and compositions
CN106832317A (zh) 一类四氮唑多孔配合物及其制备方法
Zhang et al. Synthesis and biological of novel myricetin derivatives containing 1, 3, 4-oxadiazoles
KR20150116430A (ko) 직접적인 액체 주입을 위한 ２족 이미다졸레이트 포뮬레이션
CN108059600A (zh) 一种四（二甲氨基）钛的精制方法
JP2016037654A (ja) 膜形成材料および膜形成方法
CN104045570B (zh) 一种n,n-二环己基胺-2-丁醇的合成方法
WO2022196341A1 (ja) 吸湿材および装置
US8318974B2 (en) Drying agent and method for forming the same
Tella et al. Solvent‐free Synthesis, Characterization and Solvent‐Vapor Interaction of Zinc (II) and Copper (II) Coordination Polymers containing Nitrogen‐donor Ligands
CN102432434B (zh) 一种3-甲基-3-丁烯-1-醇的合成方法
JP2016074929A (ja) 有機ルテニウム化合物からなる化学蒸着用原料及び該化学蒸着用原料を用いた化学蒸着法
CN105622471B (zh) 一种蛋氨酸衍生物缓蚀剂的制备方法
Corbett Evidence on the Nature of Bismuth (I) Chloride Formed by Solution of Bismuth in Bismuth (III) Chloride
CN106565514A (zh) 一种用四甲基氢氧化铵催化合成β‑羟烷基酰胺工艺方法
CN104151269B (zh) 一种n,n-二(哌啶甲基)-环己胺的合成方法
Sauvé et al. Carboxyl-modified amino acids and peptides: II) A convenient route for the synthesis of difunctionalized enamines from thioamides via thioiminium salts
CN104030933A (zh) 一种β-异烷醇基氨基戊酸环己胺的合成方法
JP4904029B2 (ja) ボラジン化合物の保存方法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C41 Transfer of patent application or patent right or utility model
CB03 Change of inventor or designer information

Inventor after: Chen Zheng

Inventor after: Liu Lin

Inventor after: Lv Guoan

Inventor after: Tan Pingping

Inventor before: Jian Dong Xie

Inventor before: Liu Fangxu

COR Change of bibliographic data
TA01 Transfer of patent application right

Effective date of registration: 20161011

Address after: 264006 Shandong Province, Yantai City Development Zone Branch and three branch Yongjiang Yongjiang interchange

Applicant after: SHANDONG LANMENG ANTI-CORROSION TECHNOLOGY CO.,LTD.

Address before: 264760, Yantai City, Yantai province high tech Zone, No. 101, aerospace Road, university students park C-109

Applicant before: YANTAI HENGDIKE ENERGY TECHNOLOGY Co.,Ltd.

C14 Grant of patent or utility model
GR01 Patent grant
PE01 Entry into force of the registration of the contract for pledge of patent right

Denomination of invention: one kind b- Synthesis of piperidyl alcohol

Effective date of registration: 20221208

Granted publication date: 20170208

Pledgee: Yantai Rural Commercial Bank Co.,Ltd. Zhifu District Hongkou sub branch

Pledgor: SHANDONG LANMENG ANTI-CORROSION TECHNOLOGY CO.,LTD.

Registration number: Y2022980025659

PE01 Entry into force of the registration of the contract for pledge of patent right