1-丁基-3-甲基咪唑甲磺酸 | 401788-98-5

• 物质功能分类: 化学试剂 - 有机试剂 - 离子液体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-丁基-3-甲基咪唑甲磺酸
• 中文别名: 1-丁基-3-甲基咪唑硫酸甲酯；1-正丁基-3-甲基咪唑硫酸甲酯
• 英文名称: 1-butyl-3-methylimidazolium methylsulfate
• 英文别名: 1-butyl-3-methylimidazolium methyl sulphate；1-Butyl-3-methylimidazolium methyl sulfate；1-butyl-3-methylimidazol-3-ium;methyl sulfate
• CAS: 401788-98-5
• 化学式: CH₃O₄S*C₈H₁₅N₂
• 分子量: 250.319
• InChiKey: MEMNKNZDROKJHP-UHFFFAOYSA-M

物化性质

• 熔点：
  -4°C(lit.)
• 密度：
  1.21 g/mL at 20 °C
• 稳定性/保质期：
  避免与氧化物和碱类物质接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2933290090
• 包装等级：
  II
• 危险品运输编号：
  UN 3265 8/PG 2
• 危险标志：
  GHS05
• 危险性描述：
  H314
• 危险性防范说明：
  P280,P305 + P351 + P338,P310
• 储存条件：
  保存方法：密封，存放在阴凉、通风和干燥的地方。

SDS

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Section 1: Product Identification
Chemical Name: 1-Butyl-3-methylimidazolium methanesulfonate, 98% [BMIM] [MeSO4]
CAS Registry Number: 401788-98-5
Formula: C9H18N2O4S
EINECS Number: none
Chemical Family: organic amine salt
Synonym: 3-Butyl-1-methyl-3H-imidazol-1-ium; methylsulfate

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 401788-98-5 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to eyes, skin and respiratory tract.
Primary Routes of Exposure: Ingestion, eyes, inhalation, skin contact
Eye Contact: Causes moderate to severe irritation of the eyes.
Skin Contact: Causes moderate to severe irritation of the skin
Causes irritation of the respiratory tract with burning pain in the nose and throat, coughing, and pulmonary
Inhalation:
edema.
Ingestion: May be harmful or poisonous if swallowed. Severe irritant to the gastrointestinal system
The methylsulfate fragment may act as a poisonous alkylating agent in the human body as does dimethyl
Acute Health Affects:
sulfate. Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information available on the long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: none
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit toxic organic fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a cool, dry place in a tightly sealed container.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves. Consult with glove manufacturer to determine the proper type of glove.
Ventilation: If possible, handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: If possible, handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: yellow liquid
Molecular Weight: 250.32
Melting Point: no data
Boiling Point: no data
Vapor Pressure: not applicable
Specific Gravity: no data
Odor: none
Solubility in Water: soluble

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SECTION 10: Stability and Reactivity
Stability: hygroscopic
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: contact with air and moisture
Incompatibility: strong oxidizing agents
Decomposition Products: carbon dioxide, carbon monoxide, nitrogen oxides, and organic fumes.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to federal, state, and local regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory.
SARA (Title 313): Title compound not listed.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-丁基-3-甲基咪唑甲磺酸 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-n-butyl-3-methyl-2,3-dihydro-imidazol-2-ylidene
  参考文献：
  名称：

  咪唑鎓离子液体在有机溶剂中电生成的N-杂环卡宾的稳定性和有机催化效率

  摘要：

  在有机溶剂中，通过母体1-丁基-3-甲基咪唑鎓盐BMIm-X的阴极还原，在有机溶剂中生成1-丁基-3-甲基咪唑-2-亚烷基（选择为N型杂环卡宾-NHC模型）的动力学，通过简单的伏安分析进行了研究。研究了NHC降解速率对有机催化反应效率的影响（由肉桂醛和三氟甲基苯乙酮合成γ-丁内酯）。溶剂和阴离子X的性质-对NHC的稳定性的显着效果，二（三氟甲基磺酰）亚胺阴离子为最佳长期持久的卡宾（而乙腈似乎是最糟糕的溶剂）。X的作用-已涉及到NHC和X之间的竞争-，在与BMIm +的氢键相互作用中。NHC通过氢键的稳定性越高，其降解速率越低。先前在纯BMIm-X中报道的这些氢键相互作用似乎甚至在低浓度（c <0.1 mol L -1）包含BMIm-X的有机溶剂中也有效。还指出了氮烷基取代基对NHC降解的影响（并因此对其作为有机催化剂的效率）的影响。

  DOI：

  10.1016/j.electacta.2014.11.135
• 作为产物：
  描述：

  N-丁基咪唑 、 硫酸二甲酯 以 甲苯 为溶剂， 以75%的产率得到1-丁基-3-甲基咪唑甲磺酸
  参考文献：
  名称：

  1-丁基-3-甲基咪唑硫酸甲酯的物理性质随温度的变化

  摘要：

  进行了1-丁基-3-甲基咪唑甲基硫酸甲酯的密度，声速，折射率，动态粘度和表面张力的测量，作为温度的函数。给出了离子液体的合成。离子液体的低粘度表明其在萃取过程中用作共沸混合物的分离溶剂。由密度计算出离子液体的热膨胀系数，并讨论了结果。通过与最近发表的值进行比较，分析了阳离子的烷基链长度对密度的影响。

  DOI：

  10.1021/je060313v
• 作为试剂：
  描述：

  benzylidene urea 、 乙酰乙酸乙酯 在 1-丁基-3-甲基咪唑甲磺酸 作用下， 反应 0.42h， 生成 6-甲基-2-氧代-4-苯基-1,2,3,4-四氢-5-嘧啶羧酸乙酯
  参考文献：
  名称：

  离子液体的有机催化应用：[bmim] [MeSO4]在制备二氢嘧啶酮和-硫酮的多组分反应中作为可回收的有机催化剂

  摘要：

  已经研究了基于1-丁基-3-甲基咪唑鎓的室温离子液体的有机催化潜力，该反应通过单锅多组分反应（包括醛，β-酮酸酯或β-二酮）合成二氢嘧啶酮和-硫酮，尿素或硫脲在短时间内的收率很高。研究了影响离子液体作为催化剂效率的因素，例如阴离子和咪唑鎓阳离子，特别是后者中C2取代的影响。可以回收离子液体并将其重新用于五个连续的反应，而不会显着降低催化效率。该方法用于大规模反应的适用性突出了其本体合成的潜力。 离子液体-有机催化剂-多组分反应-二氢嘧啶酮-二氢嘧啶硫酮

  DOI：

  10.1055/s-0030-1260067

文献信息

• Are Alkyl Sulfate-Based Protic and Aprotic Ionic Liquids Stable with Water and Alcohols? A Thermodynamic Approach
  作者：Johan Jacquemin、Peter Goodrich、Wei Jiang、David W. Rooney、Christopher Hardacre

  DOI：10.1021/jp312241h

  日期：2013.2.14

  transesterification reactions are observed during liquid–liquid equilibrium studies as a function of temperature for binary systems of (hydrogen sulfate-based ionic liquids + 1-butanol) and of (hydrogen sulfate-based ionic liquids + 1-octanol). Finally, this atom-efficient catalyst-free transesterification reaction between hydrogen sulfate-based ILs and alcohol was then tested to provide a novel way to synthesize

  在开发涉及这些新型材料的任何工业应用和方法之前，了解在其他分子（例如水）存在下化学稳定性随离子液体（ILs）温度变化的知识至关重要。在较大的温度范围和组成范围内，液相平衡和密度可以提供有关IL纯度和化学稳定性的基本信息。IL科学界要求从参考数据中获取准确的测量值。在这项工作中，研究了在水和各种醇（甲醇，乙醇，1-丁醇和1-辛醇）存在下，不同的基于烷基硫酸盐的离子液体的稳定性，以了解它们在高达423.15 K的温度下的稳定性。分别进行水解和酯交换反应。根据这项调查，很明显，基于硫酸甲酯和硫酸乙酯的离子液体在水的存在下不稳定，因为毫无疑问地观察到了硫酸甲酯或硫酸乙酯阴离子水解为甲醇或乙醇和氢化阴离子。这样的观察可以帮助解释不同群体在文献中发表的物理性质的差异。此外，似乎热力学平衡过程驱动了这些水解反应。换句话说，这些水解反应实际上是可逆的，从而提供了通过基于硫酸氢的IL与相应的醇（甲醇或乙醇）
• Correlation between Hydrogen Bond Basicity and Acetylene Solubility in Room Temperature Ionic Liquids
  作者：Jelliarko Palgunadi、Sung Yun Hong、Jin Kyu Lee、Hyunjoo Lee、Sang Deuk Lee、Minserk Cheong、Hoon Sik Kim

  DOI：10.1021/jp108351f

  日期：2011.2.10

  temperature ionic liquids (RTILs) are proposed as the alternative solvents for the acetylene separation in ethylene generated from the naphtha cracking process. The solubility behavior of acetylene in RTILs was examined using a linear solvation energy relationship based on Kamlet−Taft solvent parameters including the hydrogen-bond acidity or donor ability (α), the hydrogen-bond basicity or acceptor ability

  有人提出室温离子液体（RTILs）作为石脑油裂解过程中产生的乙烯中乙炔分离的替代溶剂。基于线性溶剂化能量关系，基于Kamlet-Taft溶剂参数，包括氢键酸度或给体能力（α），氢键碱度或受体能力（β）和极性，对乙炔在RTIL中的溶解行为进行了研究/极化率（π*）。发现乙炔的溶解度与β值线性相关，并且几乎与α或π*无关。乙炔在RTIL中的溶解度随阴离子氢键受体（HBA）能力的增加而增加，但几乎不受阳离子性质的影响。量子力学计算表明，乙炔的酸性质子与RTIL阴离子上的碱性氧原子特异性形成氢键。另一方面，尽管CH-π相互作用是合理的，但所有优化的结构都表明阳离子上的酸性质子并不专门与乙炔的π云缔合。热力学分析与所提出的相关性非常吻合：RTIL的β值越高，RTIL中乙炔吸收的焓就越负。
• PROCESS OF FORMING A PYRROLE COMPOUND
  申请人：Zhong Guofu

  公开号：US20110124881A1

  公开（公告）日：2011-05-26

  Disclosed is a process of forming a pyrrole compound. The process comprises contacting an α-carbonyl oxime compound 1 and an α,β-unsaturated aldehyde 2 R 1 and R 2 in compound 1 are independently selected from the group consisting of H, a silyl-group, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group, and an arylalicyclic group. The aliphatic, alicyclic, aromatic, arylaliphatic, and arylalicyclic groups comprise 0 to about 3 heteroatoms selected from the group N, O, S, Se and Si. R 3 in aldehyde 2 is selected from the group consisting of H, a silyl-group, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group, and an arylalicyclic group. The aliphatic, alicyclic, aromatic, arylaliphatic, and arylalicyclic groups comprise 0 to about 3 heteroatoms selected from the group N, O, S, Se and Si. The α-carbonyl oxime compound 1 an the α,β-unsaturated aldehyde 2 are contacted in a suitable solvent in the presence of a secondary amine. The compounds are contacted for a sufficient period of time to allow the formation of an N-hydroxypyrrole compound 3

  揭示了一种形成吡咯化合物的过程。该过程包括将α-羰基肟化合物1与α，β-不饱和醛2接触。化合物1中的R1和R2分别独立地选自H、硅基团、脂肪基、脂环基、芳香基、芳基脂肪基和芳基脂环基组成的群。脂肪、脂环、芳香、芳基脂肪基和芳基脂环基包括0到约3个来自N、O、S、Se和Si组成的杂原子。醛2中的R3选自H、硅基团、脂肪基、脂环基、芳香基、芳基脂肪基和芳基脂环基组成的群。脂肪、脂环、芳香、芳基脂肪基和芳基脂环基包括0到约3个来自N、O、S、Se和Si组成的杂原子。在适当的溶剂中，在次胺的存在下，将α-羰基肟化合物1和α，β-不饱和醛2接触。这些化合物接触一段足够的时间以允许形成N-羟基吡咯化合物3。
• Treatment of biomass to dissolve lignin with ionic liquid composition
  申请人：Brandt Agnieszka

  公开号：US09765478B2

  公开（公告）日：2017-09-19

  The present invention relates to a method for treating a lignocellulose biomass in order to dissolve the lignin therein, while the cellulose does not dissolve. The cellulose pulp obtained can be used to produce glucose. In addition the lignin can be isolated for subsequent use in the renewable chemical industry as a source for aromatic platform chemicals.

  本发明涉及一种处理木质纤维素生物质的方法，以溶解其中的木质素，而纤维素不溶解。所得的纤维素浆料可用于生产葡萄糖。此外，木质素可以被分离出来，用于可再生化工行业中作为芳香平台化学品的来源。
• A quick, simple, robust method to measure the acidity of ionic liquids
  作者：John Gräsvik、Jason P. Hallett、Trang Quynh To、Tom Welton

  DOI：10.1039/c4cc02816c

  日期：——

  Introduced here is a quick, simple, robust method to measure acidity in ionic liquid (IL) systems by the use of the NMR-probe mesityl oxide.

  这里介绍了一种快速、简单、稳健的方法，通过使用NMR探针间甲酮来测量离子液体(IL)系统中的酸度。