3,3',4,4'-二苯甲酮四甲酸二酐 | 2421-28-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酐的卤化、磺化、硝化或硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,3',4,4'-二苯甲酮四甲酸二酐
• 中文别名: 3,3',4,4'-二苯酮四酸二酐；3,3',4,4'-二苯酮四羧酸二酐；3,3'4,4'-二苯甲酮四羧酸二酐；酮酐(BTDA)；4,4'-羰基二邻苯二甲酸酐；3,3",4,4"-二苯甲酮四甲酸二酐；BTDA；5,5'-羰基双-1,3-异苯并呋喃二酮；3,3',4,4'-二苯酮四甲酸二酐；酮酐；3,3',4,4'-苯甲基酚四碳氧酐；3,3',4,4'-苯甲酮四羧酸酐；3,3',4,4'-二苯甲酮四羧酸二酐
• 英文名称: dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid
• 英文别名: 3,3',4,4'-benzophenonetetracarboxylic dianhydride；benzophenone-3,3′,4,4′-tetracarboxylic dianhydride；4,4'-carbonyldiphthalic anhydride；5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione
• CAS: 2421-28-5
• 化学式: C₁₇H₆O₇
• mdl: MFCD00005923
• 分子量: 322.23
• InChiKey: VQVIHDPBMFABCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  218-222 °C (lit.)
• 沸点：
  320°C 5mm
• 密度：
  1,57 g/cm3
• 蒸气密度：
  1.4 (vs air)
• 闪点：
  324 °C
• 溶解度：
  DMF：0.1 g/mL，透明
• 最大波长(λmax)：
  580nm(CH3CN)(lit.)
• LogP：
  3.3 at 25℃
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物及水分直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

ADMET

毒理性

• 副作用

皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S25
• 危险类别码：
  R36/37
• WGK Germany：
  1
• 海关编码：
  29183000
• 危险标志：
  GHS07
• 危险性描述：
  H319,H335
• 危险性防范说明：
  P305 + P351 + P338
• 储存条件：
  将容器密封后，放入一个密闭的储存容器中，并存放在阴凉、干燥的地方。

SDS

Name:	3 3 4 4 -Benzophenonetetracarboxylic dianhydride 96% Material Safety Data Sheet
Synonym:	4,4'-Carbonyldiphthalic anhydride, BTD
CAS:	2421-28-5

Section 1 - Chemical Product MSDS Name:3 3 4 4 -Benzophenonetetracarboxylic dianhydride 96% Material Safety Data Sheet
Synonym:4,4'-Carbonyldiphthalic anhydride, BTD

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2421-28-5	3,3',4,4'-Benzophenonetetracarboxylic	96.0	219-348-1

Hazard Symbols: XI
Risk Phrases: 36/37

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes and respiratory system.The toxicological properties of this material have not been fully investigated.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.
Antidote: None reported.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Do NOT use water directly on fire. Use foam, dry chemical, or carbon dioxide. Do NOT get water inside containers.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Do not allow contact with water. Wash clothing before reuse. Keep from contact with moist air and steam.
Storage:
Store in a tightly closed container. Store protected from moisture.
Store under nitrogen. Store in a cool, dry area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant a respirator's use. Follow the OSHA respirator regulations found in 29CFR 1910.134 or European Standard EN 149. Always use a NIOSH or European Standard EN 149 approved respirator when necessary.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Appearance: light yellow powder
Odor: Odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 215 - 217 deg C
Autoignition Temperature: Not available.
Flash Point: 300 deg C ( 572.00 deg F)
Explosion Limits, lower: 4.20 vol %
Explosion Limits, upper: 16.00 vol %
Decomposition Temperature: 300 deg C
Solubility in water: reacts
Specific Gravity/Density:
Molecular Formula: C17H6O7
Molecular Weight: 322.22

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures. May decompose on exposure to moist air or water.
Conditions to Avoid:
Incompatible materials, dust generation, moisture, excess heat, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids, strong bases, moisture.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2421-28-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,3',4,4'-Benzophenonetetracarboxylic dianhydride - Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37 Irritating to eyes and respiratory system.
Safety Phrases:
S 25 Avoid contact with eyes.
WGK (Water Danger/Protection)
CAS# 2421-28-5: No information available.
United Kingdom Occupational Exposure Limits
Canada
CAS# 2421-28-5 is listed on Canada's DSL List.
CAS# 2421-28-5 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
US FEDERAL
TSCA
CAS# 2421-28-5 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

二苯甲酮-3,3',4,4'-四羧酸二酐（BTDA）在工业领域用作中间体和缩聚剂，以制造塑料产品或精细化学品。由于 BTDA 仅在封闭的工业环境中进行生产和处理，因此消费者面临的风险非常小。有关其环境影响、生态毒理学及毒理学信息的数据基于研究以及对其危险特性的可靠评估。

理化性质

BTDA 是一种棕褐色结晶粉末，熔点为 218.67°C，在 360°C 时分解。该物质具有极高的自燃温度，并且没有观察到可燃性。其密度为 1.5452 g/ml，蒸气压为 6.53E-011 Pa。BTDA 微溶于水，log Pow 值为 3.3。

应用

BTDA 主要用作制造塑料产品或精细化学品的中间体，在工业部门中发挥着重要作用。

健康危害

通过口服、吸入或皮肤接触途径，BTDA 没有急性毒性。该物质会刺激眼睛和呼吸道，并对皮肤具有敏感性。然而，BTDA 不会导致突变。其使用包括在封闭系统中的操作以及批量过程中的混合与转移等。

用途

BTDA 用作聚合单体，用于合成耐高温高分子材料。

反应信息

• 作为反应物：
  描述：

  3,3',4,4'-二苯甲酮四甲酸二酐 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 为溶剂， 以8%的产率得到
  参考文献：
  名称：

  N-羟基邻苯二甲酰亚胺衍生物在 Fmoc 固相肽合成过程中检测胺的构效关系研究

  摘要：

  以前，我们开发了一种检测未保护氨基的方法，该方法基于它们与N-羟基邻苯二甲酰亚胺 (NHPI) 的可逆反应形成深色产物，这在进行固相肽合成时非常有用。在这里，我们描述了 NHPI 衍生物的构效关系研究，以使用分光光度计确定最适合该方法的衍生物来估计化学产率。我们发现，如果衍生物的结构包含 NHPI 框架，则衍生物与未受保护的氨基反应产生的产物只有强烈的颜色。我们还制备了五种肽，包括含有N-甲基和 D-氨基酸，以及 Pro 残基，使用我们的可逆检测方法检测未保护的氨基。还通过 NHPI ( 1 ) 和二异丙胺复合物的结构分析研究了检测反应的机理，并得出结论需要在N-羟基和胺之间形成盐。

  DOI：

  10.1021/acs.joc.2c01342
• 作为产物：
  描述：

  邻二甲苯 在 aluminum (III) chloride 、 potassium permanganate 、 水 、 sodium hydroxide 作用下， 以 吡啶 、 二苯醚 、 水 为溶剂， 反应 3.0h， 生成 3,3',4,4'-二苯甲酮四甲酸二酐
  参考文献：
  名称：

  Development and Optimization of Producing 3,3',4,4'-Benzophenonetetracarboxylic Dianhydride

  摘要：

  本文包括一系列实验，旨在开发生产 3,3',4,4'-二苯甲酮四甲酸二酐的实验室方法，并选择最佳条件，以获得最大产量。3,3',4, 4'-二苯甲酮四甲酸二酐用于制备具有高热稳定性、耐化学性以及高强度和高杨氏模量的聚酰亚胺。二苯甲酮四甲酸二酐采用多步路线制备：邻二甲苯经Friedel-Crafts烷基化得到3,3',4,4'-四甲基二苯甲酮，然后液相氧化为二苯甲酮四甲酸并脱水。

  DOI：

  10.13005/ojc/320627
• 作为试剂：
  描述：

  cis-1,2-diphenylcyclopropane 在 3,3',4,4'-二苯甲酮四甲酸二酐 作用下， 以 氯仿 为溶剂， 生成 1,2-二苯基环丙烷
  参考文献：
  名称：

  Bond-Coupled Electron Transfer Processes:  A New Strategy for High-Efficiency Photoinduced Electron Transfer Reactions

  摘要：

  DOI：

  10.1021/ja962291a

文献信息

• Para—or meso-functionalized aromatic ketone compounds, preparation methods thereof, and photopolymerization initiators comprising the same
  申请人：Zhang Yongbo

  公开号：US08742175B2

  公开（公告）日：2014-06-03

  The present invention discloses novel aromatic ketone compounds with functional substitution groups at para- or meta positions which can be used as photo-initiators or effective components of photo-initiator mixtures for the photopolymerizations of ethylenically unsaturated systems. The preparation of these compounds is also disclosed.

  本发明公开了新颖的芳香酮化合物，其在对位或间位具有功能性取代基，可用作乙烯基不饱和体系光聚合的光引发剂或光引发剂混合物的有效成分。这些化合物的制备方法也一并公开。
• Brønsted Base-Assisted Boronic Acid Catalysis for the Dehydrative Intramolecular Condensation of Dicarboxylic Acids
  作者：Akira Sakakura、Takuro Ohkubo、Risa Yamashita、Matsujiro Akakura、Kazuaki Ishihara

  DOI：10.1021/ol102926n

  日期：2011.3.4

  base-assisted boronic acid catalysis for the dehydrative self-condensation of carboxylic acids is described. Arylboronic acid bearing bulky (N,N-dialkylamino)methyl groups at the 2,6-positions can catalyze the intramolecular dehydrative condensation of di- and tetracarboxylic acids. This is the first successful method for the catalytic dehydrative self-condensation of carboxylic acids.

  描述了布朗斯台德碱辅助硼酸催化羧酸的脱水自缩合反应。在2，6-位带有大的（N，N-二烷基氨基）甲基的芳基硼酸可以催化二羧酸和四羧酸的分子内脱水缩合。这是羧酸催化脱水自缩合的第一个成功方法。
• A novel one-pot isocyanide-based four-component reaction: synthesis of highly functionalized 1H-pyrazolo[1,2-b]phthalazine-1,2-dicarboxylates and 1H-pyrazolo[1,2-a]pyridazine-1,2-dicarboxylates
  作者：Sajjad Keshipour、Salman Shojaei、Ahmad Shaabani

  DOI：10.1016/j.tet.2012.05.078

  日期：2012.8

  A new protocol has been developed for the efficient synthesis of structurally diverse 1H-pyrazolo[1,2-b]phthalazine-1,2-dicarboxylates and 1H-pyrazolo[1,2-a]pyridazine-1,2-dicarboxylates via a four-component reaction of hydrazine hydrate, dialkyl acetylenedicarboxylates, isocyanides and various cyclic anhydrides such as succinic anhydride, maleic anhydride and phthalic anhydride in ethanol/acetone

  为有效合成结构上不同的1 H-吡唑并[ 1,2- b ]邻苯二甲酰基-1,2-二羧酸酯和1 H-吡唑并[ 1,2- a ]哒嗪-1,2-二羧酸酯已开发出新的方案通过水合肼，乙炔二羧酸二烷基酯，异氰酸酯和各种环酐（如琥珀酸酐，马来酸酐和邻苯二甲酸酐）在室温下于乙醇/丙酮（1：1）中以良好至中等的收率进行四组分反应。
• METHOD FOR PRODUCING CARBOXYLIC ANHYDRIDE AND ARYLBORONIC ACID COMPOUND
  申请人：Ishihara Kazuaki

  公开号：US20110319620A1

  公开（公告）日：2011-12-29

  When phthalic acid is heated in heptane under azeotropic reflux conditions in the presence of a catalytic amount of an arylboronic acid compound (such as 2,6-(diisopropylaminomethyl)phenylboronic acid or 2,6-bis(diisopropylaminomethyl)phenylboronic acid), phthalic anhydride is obtained in high yield.

  当邻苯二甲酸在庚烷中，在存在催化量的芳基硼酸化合物（如2,6-(二异丙氨基甲基)苯硼酸或2,6-双(二异丙氨基甲基)苯硼酸）的条件下，进行共沸回流加热时，可以获得高产率的邻苯二甲酸酐。
• （メタ）アクリルイミド化合物およびそれを用いたインク
  申请人：ＪＮＣ株式会社

  公开号：JP2017202987A

  公开（公告）日：2017-11-16

  【課題】 加熱処理を、省略あるいはより低温かつ短時間で行うことができ、耐熱性および絶縁性に優れたポリイミド膜を形成することができる新規化合物の提供。【解決手段】 式（１）で表される（メタ）アクリルイミド化合物（Ａ）。【化１】［式（１）中、Ｘは炭素数２〜１００の四価の有機基であり、複数あるＹはそれぞれ独立に炭素数１〜１００の二価の有機基であり、複数あるＺはそれぞれ独立に炭素数１〜２０のアルキレン基であり、複数あるＲはそれぞれ独立に水素またはメチルである。］【選択図】無し

  提供一种新型化合物，可以在省略或更低温且更短时间内进行热处理，形成具有优异耐热性和绝缘性能的聚酰亚胺膜。该化合物由式（1）表示为（亚）丙烯酰亚胺化合物（A）。 【化1】[在式（1）中，X是碳数为2〜100的四价有机基，多个Y分别独立地是碳数为1〜100的二价有机基，多个Z分别独立地是碳数为1〜20的亚烷基，多个R分别独立地是氢或甲基。] 【选择图】无

表征谱图