levoglucosenone | 37112-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: levoglucosenone
• 英文别名: LGO；6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one
• CAS: 37112-31-5
• 化学式: C₆H₆O₃
• mdl: MFCD00191664
• 分子量: 126.112
• InChiKey: HITOXZPZGPXYHY-UHFFFAOYSA-N

物化性质

• 比旋光度：
  D25 -460° (c = 1.0 in CHCl3) (Halpern, 1973); D31 -514.8° (c = 0.3 in CHCl3) (Taniguchi).
• 沸点：
  113°C/3mmHg(lit.)
• 密度：
  1.329±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、乙酸乙酯（少量）
• LogP：
  -0.740 (est)
• 保留指数：
  1070.3

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P264,P270,P280,P301+P312+P330,P305+P351+P338,P337+P313,P501
• 危险性描述：
  H302,H319

SDS

Levoglucosenone Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Levoglucosenone

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Levoglucosenone
Percent: >96.0%(GC)
CAS Number: 37112-31-5
Chemical Formula: C6H6O3

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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.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Unsuitable extinguishing Solid streams of water
media:
Levoglucosenone

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: 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
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapour or mist. Wash hands and face thoroughly after
handling.
Use a ventilation, local exhaust if vapour or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Light-sensitive
Packaging material: Comply with laws.

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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.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
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
Clear
Form:
Colour: Yellow - Reddish yellow
No data available
Odour:
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: 113°C/0.4kPa
No data available
Flash point:
Flammability or explosive
limits:
Lower: No data available
No data available
Upper:
Relative density: 1.31
Solubility(ies):
[Water] No data available
Levoglucosenone

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
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: cyt-ham-lng 2 mg/L
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available
JG7020000
RTECS Number:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
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
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
Levoglucosenone

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  levoglucosenone 在 氢气 作用下， 以 水 为溶剂， 150.0 ℃ 、3.45 MPa 条件下， 反应 3.0h， 生成 1,2,5,6-四羟基己烷
  参考文献：
  名称：

  [EN] CATALYTIC PRODUCTION OF 1,2,5,6-HEXANETETROL FROM LEVOGLUCOSENONE
  [FR] PRODUCTION CATALYTIQUE DE 1,2,5,6-HEXANETÉTROL À PARTIR DE LÉVOGLUCOSÉNONE

  摘要：

  公开号：

  WO2019204753A9

文献信息

• [EN] PRODUCTION OF LEVOGLUCOSENONE<br/>[FR] PRODUCTION DE LÉVOGLUCOSÉNONE
  申请人：DU PONT

  公开号：WO2016039996A1

  公开（公告）日：2016-03-17

  Disclosed herein are processes for producing levoglucosenone. In one embodiment, the process comprises the steps: a) contacting in a continuous manner a carbohydrate source, a solvent, and an acid in a continuous liquid phase reactor under reaction conditions sufficient to form a reaction mixture comprising levoglucosenone, wherein the reaction conditions include a liquid residence time in the reactor between about 0.1 minutes and about 20 minutes; b) withdrawing a portion of the reaction mixture from the reactor to obtain a product stream comprising levoglucosenone; and c) optionally, isolating levoglucosenone from the product stream.

  本文披露了生产左旋葡萄糖酮的过程。在一种实施例中，该过程包括以下步骤：a) 在连续液相反应器中以连续方式接触碳水化合物源、溶剂和酸，在足以形成包含左旋葡萄糖酮的反应混合物的反应条件下进行反应，其中反应条件包括在反应器中的液体停留时间约为0.1分钟至约20分钟之间；b) 从反应器中提取部分反应混合物，以获得包含左旋葡萄糖酮的产品流；以及c) 可选地，从产品流中分离左旋葡萄糖酮。
• [EN] CHIRAL AUXILIARIES AND USES THEREOF<br/>[FR] AUXILIAIRES CHIRAUX ET LEURS UTILISATIONS
  申请人：UNIV OF NEW ENGLAND

  公开号：WO2019060953A1

  公开（公告）日：2019-04-04

  The present invention relates to chiral auxiliaries and the syntheses thereof and uses thereof.

  本发明涉及手性辅助剂及其合成和用途。
• Metal-containing zeolites as efficient catalysts for the transformation of highly valuable chiral biomass-derived products
  作者：Cecilia Paris、Manuel Moliner、Avelino Corma

  DOI：10.1039/c3gc40267c

  日期：——

  Metal-containing zeolites, especially Sn-Beta, perform as very efficient heterogeneous catalysts in the selective oxidation of levoglucosenone, which is considered as a platform chemical for the production of highly-valuable chemicals, towards the synthesis of the optically pure γ-lactone (S)-γ-hydroxymethyl-α,β-butenolide (HBO) using H2O2 as an oxidizing agent. Using Sn-Beta as a catalyst, yields up to 75% of (S)-γ-hydroxymethyl-α,β-butenolide are achieved in a “one-pot” cascade reaction. When Sn-Beta is combined with an acid resin, such as Amberlyst-15, the “two-step” process allows yields up to 90%.

  含金属的沸石，尤其是 Sn-Beta，是一种非常高效的异相催化剂，可用于选择性氧化被视为生产高价值化学品的平台化学品的左旋葡烯酮，以 H2O2 为氧化剂合成光学纯的γ-内酯 (S)-γ-羟甲基-α,β-丁烯内酯 (HBO)。使用 Sn-Beta 作为催化剂，在 "一锅式 "级联反应中，(S)-γ-羟甲基-α,β-丁烯内酯的产量可达 75%。当 Sn-Beta 与 Amberlyst-15 等酸性树脂结合使用时，"两步法 "工艺的产率可达 90%。
• PRODUCTION OF HYDROXYMETHYLFURFURAL FROM LEVOGLUCOSENONE
  申请人：E I DU PONT DE NEMOURS AND COMPANY

  公开号：US20130172580A1

  公开（公告）日：2013-07-04

  Disclosed are processes comprising contacting an aqueous reaction mixture having an initial pH between about 3 and about 6 and comprising levoglucosenone with a catalyst, and heating the reaction mixture to form a product mixture comprising 5-hydroxymethyl-2-furfural. The processes may further comprise heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a hydrogenation catalyst to form a second product mixture comprising one or more of 2,5-furandimethanol, tetrahydrofuran 2,5-dimethanol, 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol.

  本发明涉及一种工艺，包括将初始pH在大约3到大约6之间的含有levoglucosenone的水相反应混合物与催化剂接触，加热反应混合物以形成包含5-羟甲基-2-呋喃醛的产物混合物。该工艺还可以包括在氢气和加氢催化剂的存在下加热包含5-羟甲基-2-呋喃醛的产物混合物，以形成第二个产物混合物，其中包括2,5-呋喃二甲醇、四氢呋喃-2,5-二甲醇、1,2,6-己三醇、2-羟甲基四氢呋喃和1,6-己二醇中的一个或多个。
• Cathodically Promoted Stereoselective Addition of 1,3-Dinitro Compounds to Levoglucosenone
  作者：Zukhra I. Niazimbetova、Dennis H. Evans、Christopher D. Incarvito、Arnold L. Rheingold

  DOI：10.1149/1.1393449

  日期：——

  This paper reports new applications of the cathodically promoted addition of nitro compounds to the biomass-derived enone, levoglucosenone. A series of 2-substituted 1,3-dinitropropanes were found to undergo addition to levoglucosenone with generation of a tricyclic product containing a fused cyclohexane system. The reaction yields are good to excellent and are catalyzed by base (superoxide) generated

  本文报道了阴极促进硝基化合物添加到生物质衍生的烯酮左旋葡萄糖酮中的新应用。发现一系列 2-取代的 1,3-二硝基丙烷与左旋葡萄糖酮发生加成，生成含有稠合环己烷系统的三环产物。反应产率从好到极好，并由电化学产生的碱（超氧化物）催化。衍生物由具有以下 2-取代基的 1,3-二硝基丙烷制备：2-噻吩基、2-呋喃基、N-甲基-2-吡咯基、苯基、9-蒽基和二茂铁基。2-二茂铁基-1,3-二硝基丙烷衍生物的结构是通过 X 射线晶体学确定的，从而证实了所有其他产品的基于 NMR 的立体化学分配。