壬二酸二甲酯 | 1732-10-1

• 物质功能分类: 催化剂及助剂 - 塑料橡胶助剂 - 增塑剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 壬二酸二甲酯
• 中文别名: 二甲基壬二酸酯；杜鹃花酸二甲酯；二甲基杜鹃花酸酯；壬二酸二甲基酯
• 英文名称: Dimethyl azelate
• 英文别名: dimethyl nonanedioate；nonanedioic acid dimethyl ester；azelaic acid dimethyl ester；dimethyl nonandioate；nonanedioic acid, 1,9-dimethyl ester；methyl azelate
• CAS: 1732-10-1
• 化学式: C₁₁H₂₀O₄
• mdl: MFCD00025898
• 分子量: 216.277
• InChiKey: DRUKNYVQGHETPO-UHFFFAOYSA-N

物化性质

• 熔点：
  18 °C
• 沸点：
  156 °C/20 mmHg (lit.)
• 密度：
  1.007 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• LogP：
  2.5-2.86 at 25℃
• 保留指数：
  1511;1510;1485;1519;1511;1511;1512;1512;1513;1512;1510;1519;1515.1;1481.7;266.6;266.6
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• TSCA：
  Yes
• 安全说明：
  S23,S24/25
• 危险品运输编号：
  NONH for all modes of transport
• WGK Germany：
  1
• 海关编码：
  2917139000
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥的地方。

SDS

Dimethyl Azelate Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: Dimethyl Azelate

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
None
Pictograms or hazard symbols
Signal word No signal word
None
Hazard statement
Precautionary statements None

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): Dimethyl Azelate
Percent: >98.0%(GC)
CAS Number: 1732-10-1
Synonyms: Azelaic Acid Dimethyl Ester , Dimethyl Nonanedioate , Nonanedioic Acid Dimethyl
Ester
Chemical Formula: C11H20O4

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Extinguishing media not to Solid streams of water
be used:
Dimethyl Azelate

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Section 5. FIRE-FIGHTING MEASURES
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapor or mist. Wash hands and face thoroughly after handling.
Use a ventilation, local exhaust if vapor or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Keep container tightly closed. Store in a cool and dark place.
Storage conditions:
Store away from incompatible materials such as oxidizing agents.
Law is followed.
Packaging material:

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: clear
Color: Colorless - Pale yellow
Odor: No data available
pH: No data available
Melting point/freezing point:18 °C
Boiling Point/Range: 140 °C
Flash Point: No data available
Explosive limits
Lower: No data available
Upper: No data available
Density: 1.01
Solubility: No data available

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
No special reactivity has been reported.
Reactivity:
Incompartible materials: oxidizing agents
Dimethyl Azelate

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Section 10. STABILITY AND REACTIVITY
Hazardous Decomposition Carbon monoxide, Carbon dioxide
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobillity in soil
log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not Listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.
Dimethyl Azelate

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

壬二酸二甲酯主要用于有机合成或航空领域，如涡轮发动机润滑油、精密仪器仪表用油以及汽车发动机机油等。

反应信息

• 作为反应物：
  描述：

  壬二酸二甲酯 生成 2-氧代环辛烷-1-羧酸甲酯
  参考文献：
  名称：

  Mass spectra of aliphatic dicarboxylic acids and their dimethyl esters: Cyclic structures for the [M − H2O]+˙ ions from the diacids and [M − MeOH]+˙ ions from the dimethyl esters

  摘要：

  AbstractMethyl 2‐oxocycIoalkane carboxylate structures are proposed lor the [M − MeOH]+˙ ions from dimethyl adipate, pimelate, suberate and azelate. This proposal is based on a comparison of the metastable ion mass spectra and the kinetic energy releases for the major fragmentation reaction of these species with the same data for the molecular ions of authentic cyclic β‐keto esters. The mass spectra of α,α,α′,α′‐d4‐pimelic acid and its dimethyl ester indicate that the α‐hydrogens are involved only to a minor extent in the formation of [M − ROH]+˙ and [M − 2ROH]+˙ ions, while these α‐hydrogens are involved almost exclusively in the loss of ROH from the [M − RO˙]+ ions (R = H or CH3). The molecules XCO(CH2)7COOMe (X = OH, Cl) form abundant ions in their mass spectra with the same structure as the [M − 2MeOH]+˙ ions from dimethyl azelate.

  DOI：

  10.1002/oms.1210231009
• 作为产物：
  描述：

  油酸 在 potassium permanganate 、 硫酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 11.0h， 生成 壬二酸二甲酯
  参考文献：
  名称：

  由油酸合成支链生物润滑油基础油。

  摘要：

  合成润滑剂（聚α-烯烃，PAO）的成熟制造是通过石化乙烯的低聚，聚合和加氢反应进行的。在这项工作中，我们利用廉价的生物来源油酸作为原料，通过全碳链合成而无碳损失地合成了rot型C 45生物润滑油基础油。它包含多个级联化学过程：将油酸氧化为壬二酸（进一步酯化为壬二酸二甲酯）和壬酸（均为C 9链）。然后将后者选择性地氢化成壬醇，并溴化成溴格里雅试剂。下一步，通过亲核加成（NPA）过量的C 9形成C 45生物润滑油基础油。溴化格氏试剂与壬二酸二甲酯，然后进行加氢脱氧。所制备的生物润滑油基础油的具体性能几乎与商用润滑油PAO6（ExxonMobil）的性能相同。该工艺为生产增值生物润滑油基础油提供了一条新的有希望的途径。

  DOI：

  10.1002/cssc.202001551
• 作为试剂：
  描述：

  3,4,5,6-Tetra-O-acetyl-2-desoxy-D-arabino-hexonsaeuremethylester 在 氢氧化钾 、 壬二酸二甲酯 、 氢溴酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 2,3,4,5-Tetra-O-acetyl-1-deoxyarabitol
  参考文献：
  名称：

  Harenbrock, Michael; Matzeit, Agnes; Schaefer, Hans J., Liebigs Annalen, 1996, # 1, p. 55 - 62

  摘要：

  DOI：

文献信息

• [EN] BORON-CONTAINING RHO KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA RHO KINASE CONTENANT DU BORE
  申请人：PERCIPIAD INC

  公开号：WO2021011873A1

  公开（公告）日：2021-01-21

  The present invention provides boron-containing isoquinoline compounds as protein kinase-modulating compounds. These compounds are useful as neuroprotective and neuro-regenerative agents for the amelioration of glaucoma and other ocular neuropathies.

  本发明提供了含硼的异喹啉化合物作为蛋白激酶调节化合物。这些化合物可用作神经保护和神经再生剂，用于改善青光眼和其他眼神经病变。
• Process for preparing a carboxylic acid from a diol or from an epoxide by oxidative cleavage
  申请人：SOCIETE INTEROLEAGINEUSE D'ASSISTANCE ET DE DEVELOPPEMENT (S.I.A.)

  公开号：US09359280B2

  公开（公告）日：2016-06-07

  A process for preparing a carboxylic acid, by oxidative cleavage of at least one vicinal diol, or an epoxide, wherein the reaction is carried out in the presence of a catalyst and of an oxidizing agent and in the absence of solvent.

  通过氧化裂解至少一个邻二醇或环氧化物来制备羧酸的过程，其中反应在催化剂和氧化剂的存在下，在无溶剂的情况下进行。
• Ruthenium catalysed oxidation without CCl4 of oleic acid, other monoenic fatty acids and alkenes
  作者：François Zimmermann、Eric Meux、Jean-Luc Mieloszynski、Jean-Marie Lecuire、Nicolas Oget

  DOI：10.1016/j.tetlet.2005.03.052

  日期：2005.5

  Ruthenium catalysed oxidation of alkenes and monoenic fatty acids is reported. The study of the influence of cosolvents (H2O/MeCN/X) shows that toxic CCl4 initially used in the Sharpless system (H2O/MeCN/CCl4) can be avoided and demonstrates that the oxidative cleavage of CC bond could be accomplished in good yields with H2O/MeCN/AcOEt solvent system in a ratio 3/2/2, respectively.

  据报道，钌催化烯烃和单烯脂肪酸的氧化。对助溶剂（H 2 O / MeCN / X）影响的研究表明，可以避免最初在Sharpless系统中使用的有毒CCl 4（H 2 O / MeCN / CCl 4），并且证明了CC键的氧化裂解可以用比例为3/2/2的H 2 O / MeCN / AcOEt溶剂体系可实现高收率。
• A general platinum-catalyzed alkoxycarbonylation of olefins
  作者：Ji Yang、Jiawang Liu、Yao Ge、Weiheng Huang、Carolin Schneider、Ricarda Dühren、Robert Franke、Helfried Neumann、Ralf Jackstell、Matthias Beller

  DOI：10.1039/d0cc00650e

  日期：——

  Hydroxy- and alkoxycarbonylation reactions constitute important industrial processes in homogeneous catalysis. Nowadays, palladium complexes constitute state-of-the-art catalysts for these transformations. Herein, we report the first efficient platinum-catalysed alkoxycarbonylations of olefins including sterically hindered and functionalized ones. This atom-efficient catalytic transformation provides

  羟基和烷氧羰基化反应在均相催化中构成重要的工业过程。如今，钯配合物构成了这些转化的最新催化剂。本文中，我们报道了第一个有效的铂催化烯烃的烷氧基羰基化反应，包括空间受阻和官能化的烯烃。这种原子效率高的催化转化可直接获得各种有价值的酯，收率好至极好，而且通常具有很高的选择性。在动力学实验中，比较了基于Pd和Pt的催化剂的活性。即使在低催化剂负载下，Pt仍显示出高催化活性。
• METHOD FOR PREPARING CARBOXYLIC ACIDS BY OXIDATIVE CLEAVAGE OF A VICINAL DIOL
  申请人：Lemaire Marc

  公开号：US20130131379A1

  公开（公告）日：2013-05-23

  The present invention relates to a method for preparing carboxylic acids, in particular mono- and dicarboxylic acids, by oxidative cleavage of a vicinal diol. According to the invention, said method consists of reacting a vicinal diol of formula I: where: p is an integer comprised between 1 and 6; R1 and R2 are, separately: an alkyl or hydroxyl group having 1 to 12 carbon atoms; a —(CH 2 ) n —C0 2 M group where n, which can be identical or different in R1 and R2, is an integer comprised between 1 and 11 and M is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or an alkaline cation; or R1 and R2 jointly form an alkylene —(CH 2 )m- group where m is an integer comprised between 2 and 10, preferably between 2 and 6; with industrial-grade sodium hypochlorite (or bleach), in the absence of an organic solvent and without adding a catalyst, preferably at room temperature. The invention can be used for recycling natural vegetable oils.

  本发明涉及一种制备羧酸的方法，特别是通过对邻二醇进行氧化裂解制备单羧酸和二羧酸。 根据本发明，所述方法包括将式I的邻二醇进行反应： 其中： p是介于1和6之间的整数； R1和R2分别是： 具有1至12个碳原子的烷基或羟基基团； 一个—(CH 2 ) n —C0 2 M基团，其中n在R1和R2中可以相同也可以不同，是介于1和11之间的整数，M是氢原子或具有1至4个碳原子的烷基基团或碱性阳离子； 或者R1和R2共同形成一个亚烷基—(CH 2 )m-基团，其中m是介于2和10之间的整数，优选在2和6之间； 使用工业级次氯酸钠（或漂白剂），在无机溶剂的情况下且不添加催化剂的情况下，最好在室温下进行。该发明可用于回收天然植物油。

表征谱图