壬酸 | 112-05-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 无环羧酸
• 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: 壬酸
• 中文别名: 风吕草酸；天竺葵酸；正壬酸；洋绣球酸；洋秀球酸；洋锈球酸；C9酸
• 英文名称: nonanoic acid
• 英文别名: pelargonic acid；n-nonanoic acid；C9:0
• CAS: 112-05-0
• 化学式: C₉H₁₈O₂
• mdl: MFCD00004433
• 分子量: 158.241
• InChiKey: FBUKVWPVBMHYJY-UHFFFAOYSA-N

物化性质

• 熔点：
  9 °C (lit.)
• 沸点：
  268-269 °C (lit.)
• 密度：
  0.906 g/mL at 25 °C (lit.)
• 蒸气密度：
  5.5 (vs air)
• 闪点：
  212 °F
• 溶解度：
  0.3g/l
• 介电常数：
  13.9（25℃）
• LogP：
  3.4 at 25℃
• 物理描述：
  Liquid; OtherSolid, Liquid
• 颜色/状态：
  Colorless, oily liquid at ordinary temp; crystallizes when cooled
• 气味：
  FATTY ODOR
• 味道：
  UNPLEASANT TASTE
• 蒸汽密度：
  4.41 (Air = 1)
• 蒸汽压力：
  1.65X10-3 mm Hg at 25 °C
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 粘度：
  8.08 mPa.sec at 20 °C
• 燃烧热：
  -5,456.1 kJ/mol
• 气味阈值：
  Aroma threshold values: Detection: 3 to 9 ppm.
• 折光率：
  Index of refraction: 1.4343 at 20 °C/D
• 解离常数：
  pKa = 4.95 at 25 °C
• 碰撞截面：
  143.33 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 保留指数：
  1268;1263;1263;1276;1260;1256;1269;1256;1280;1280;1260;1272;1295;1300;1302;1302;1303;1283;1255;1263;1263;1272;1244;1247;1239;1261;1256;1308;1241;1277;1300;1278;1278;1253;1280;1260;1279;1264.7;1279;1272;1276
• 稳定性/保质期：

  1. 具有腐蚀性，小鼠经口LD50为15mg/kg，静脉注射LD50为224mg/kg。操作时应穿戴防护用具。

  2. 存在于烤烟、白肋烟、香料烟的烟叶及烟气中。

  3. 自然界中也存在于香蕉、啤酒和面包中。

  4. 具有强烈的刺激性。

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

向狗体内注入含有20%三壬酸盐、0.9%氯化钠和1%大豆卵磷脂的乳液，导致壬酸的氧化。

INFUSION OF AN EMULSION CONTAINING 20% TRINONANOATE, 0.9% SODIUM CHLORIDE, & 1% SOYBEAN LECITHINS INTO DOGS RESULTED IN OXIDN OF NONANOIC ACID.

来源:Hazardous Substances Data Bank (HSDB)

代谢

壬酸被肝脏代谢产生酮体。代谢过程通过β-氧化进行，在大鼠中没有发现链延长或组织储存该酸的证据。末端丙酸残基的代谢导致葡萄糖和糖原合成增加。

NONANOIC ACID IS METABOLIZED BY THE LIVER TO PRODUCE KETONE BODIES. METABOLISM OCCURS VIA BETA-OXIDATION, AND NO EVIDENCE WAS FOUND IN RATS OF CHAIN ELONGATION OR TISSUE STORAGE OF THE ACID. METAB OF THE TERMINAL PROPIONIC ACID RESIDUE RESULTS IN INCREASED GLUCOSE AND GLYCOGEN SYNTHESIS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

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

毒理性

• 相互作用

40%丙醇中的壬酸（NON）... 通过20 MHz B扫描记录的图像分析（Dermascan C, Cortex Technology）评估皮肤反应。18名18至45岁的女性进行了24小时贴片测试，实验开始时、贴片测试后24小时和48小时进行了临床和仪器评估。为了检查可能的区域性变化... /NON/在同一前臂上应用了2次。作为对照测试，应用了盐水溶液、丙醇和3%的月桂基硫酸钠（SLS）。超声图像由一个程序处理，该程序能够根据给回波的振幅分配虚构值，选择感兴趣的振幅带，对图像进行二值转换，并计算在同一振幅范围内反射的区域扩展。超声记录通过一个振幅间隔标记真皮的 低反射部分（对应于水肿和炎症浸润），并通过一个带突出表皮的入口回声（表皮）... 评估显示，真皮的低回声区域扩展根据炎症反应的强度而增加，对所有刺激物质都适用。在SLS贴片测试点，24小时内在表皮回声的反射性明显降低，而在用NON进行的贴片测试点... 超反射像素的值有增加的趋势。在近端和远端皮肤位点记录的数据之间没有显著变化... /40%丙醇中的壬酸/

Skin reactions to 40% nonanoic acid in propanol (NON) ... were evaluated by image analysis of 20 MHz B scan recordings (Dermascan C, Cortex Technology). 18 women, aged 18 to 45, were patch tested with 24-hr application time, and clinical and instrumental evaluations were performed at the beginning of the experiment, and 24 and 48 hr after patch testing. To check possible regional variations ... /NON/ was applied 2 x on the same forearm. As control tests, saline solution, propanol and sodium lauryl sulfate (SLS) 3% were applied. Echographic images were processed by a program enabling numerical representation of picture data, based on attribution of fictional values to the echoes' amplitudes, selection of amplitude bands of interest, binary transformation of the image, and calculation of the extension of areas reflecting within the same amplitude range. Sonographic recordings were evaluated by an amplitude interval marking hyporeflecting parts of the dermis (corresponding to edema and inflammatory infiltration), and by a band highlighting the entrance echo (epidermis) ... Evaluations showed that extension of the hypoechogenic area of the dermis increases according to intensity of inflammatory reaction for all irritant substances. A clear decrease in reflectivity of the epidermis echo at 24 hr was visible at SLS patch test test sites, whereas at patch test sites performed with NON ... there was a trend towards an increase in values of hyperreflecting pixels. No significant variations between data recorded at proximal compared to distal skin sites were observed ... /40% Nonanoic acid in propanol/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 紧急急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练进行操作。根据需要进行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或将其置于左侧（如果可能的话，头部向下），以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /有机酸及相关化合物/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，辅助呼吸。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的呕吐反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。活性炭无效……。不要尝试中和，因为可能会发生放热反应。在去污后，用干燥、无菌的敷料覆盖皮肤烧伤……。/有机酸及其相关化合物/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。在上呼吸道阻塞的最初迹象出现时，可能需要尽早进行插管。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β受体激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注5%葡萄糖水（D5W）/SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%盐水（NS）或乳酸钠林格液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。如果病人在正常血容量时低血压，考虑使用血管加压药。注意观察液体过载的迹象……。使用丙美卡因盐酸协助眼部冲洗……。/有机酸及相关化合物/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S28,S28A,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  1
• 海关编码：
  2915900090
• 危险品运输编号：
  UN 3265 8/PG 3
• 危险类别：
  8
• RTECS号：
  RA6650000
• 包装等级：
  III
• 危险标志：
  GHS05
• 危险性描述：
  H314
• 危险性防范说明：
  P280,P303 + P361 + P353,P304 + P340 + P310,P305 + P351 + P338
• 储存条件：
  1. 储存于阴凉、通风的库房。远离火种和热源，避免阳光直射，并保持容器密封。应与氧化剂和酸类分开存放，切忌混储。配备相应品种和数量的消防器材。储区应备有泄漏应急处理设备和合适的收容材料。 2. 工业品可用塑料桶包装，每桶25kg；分析试剂则用玻璃瓶装，每瓶500g。按一般化学品的要求进行储存和运输。

SDS

Name:	n-Nonanoic acid 97% Material Safety Data Sheet
Synonym:	Pelargonic Acid
CAS:	112-05-0

Section 1 - Chemical Product MSDS Name:n-Nonanoic acid 97% Material Safety Data Sheet
Synonym:Pelargonic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
112-05-0	n-Nonanoic acid	97%	203-931-2

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns. Causes redness and pain.
Skin:
Causes skin burns. Causes redness and pain.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively.

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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. Will burn if involved in a fire. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Use only in a chemical fume hood. Discard contaminated shoes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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.
Exposure Limits CAS# 112-05-0: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Clear liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 254 deg C
Freezing/Melting Point: 12.5 deg C
Autoignition Temperature: Not available.
Flash Point: 114 deg C ( 237.20 deg F)
Explosion Limits, lower: 1.20
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 0.3g/l
Specific Gravity/Density: 0.900
Molecular Formula: C9H18O2
Molecular Weight: 158.1248

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
None reported.
Incompatibilities with Other Materials:
Bases, oxidizing agents, reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 112-05-0: RA6650000 LD50/LC50:
CAS# 112-05-0: Draize test, rabbit, eye: 91 mg Severe; Draize test, rabbit, eye: 100 uL Mild; Draize test, rabbit, skin: 500 mg/24H Moderate; Oral, mouse: LD50 = >5 gm/kg; Oral, rat: LD50 = >5 gm/kg; Skin, rat: LD50 = >2 gm/kg.
Carcinogenicity:
n-Nonanoic acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3265
Packing Group: III
IMO
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 112-05-0: No information available.
Canada
CAS# 112-05-0 is listed on Canada's DSL List.
CAS# 112-05-0 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 112-05-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

性质

壬酸在常温常压下为无色透明的液体状，是一种具有一定极性和酸性的有机化合物。它具有一系列特征性的物理化学性质，这些性质决定了它在制备香料、涂料、塑料和橡胶等许多领域中的广泛应用。此外，壬酸还可以被还原成庚烷。与醇类反应时，它可以生成相应的酯。

含量分析

准确称取约1.0g试样，放入装有75～100ml水的250ml三角烧瓶中，加入酚酞指示剂，用0.5mol/L氢氧化钠溶液滴定至出现粉红色并维持15s。每毫升0.5mol/L氢氧化钠溶液相当于79.12mg壬酸。

毒性

壬酸具有腐蚀性。小鼠经口LD₅₀为15mg/kg，静脉注射LD₅₀为224mg/kg。操作人员应穿戴防护用具。

使用限量

• FEMA(mg/kg)：软饮料1.8；冷饮7.8；糖果6.6；焙烤食品13；起酥油10。
• 适度为限（FDA§172.515，2000）。

食品添加剂最大允许使用量与最大允许残留量标准

添加剂中文名称	允许使用该种添加剂的食品中文名称	添加剂功能	最大允许使用量（g/kg）	最大允许残留量（g/kg）
壬酸	食品	食品用香料	用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量

化学性质

壬酸是一种无色油状液体，工业品可能呈淡黄色。它具有微弱特殊气味，并且不溶于水，但可溶于乙醇、乙醚和氯仿。

用途

• 壬酸用作油漆干燥剂、增塑剂及合成润滑剂等。
• 根据GB 2760-96规定，壬酸是允许使用的食用香料，主要用来配制椰子和浆果类香精。
• 它也是有机合成原料。通过氧化可制成壬二酸；经氨化氢化得到壬胺；加压氢化可生成壬醇。此外，壬酸还用于生产壬酸酯类增塑剂，并且用作油漆干燥剂。
• 壬酸可用作洗涤剂漂白活化剂的中间体，也可用于生产作为纤维和喷气涡轮机润滑剂的多元醇酯。

生产方法

天然存在的壬酸（游离或酯化状态）存在于玫瑰、香叶、鸢尾、酒花、薰衣草等精油中。工业上由1-辛烯或油酸氧化制得。

1. 油酸经硝酸或臭氧氧化；
2. 以1-辛烯和合成气为原料，经过羰基化制得壬醛，然后通过空气氧化得到壬酸。实验室制备时，可以将重蒸过的丙二酸二乙酯加入丁醇钠中，在80-90℃下加热，随后加入溴庚烷进行反应，并在石蕊呈中性后加入氢氧化钾溶液，加热回流4-5小时。皂化完成后通过水蒸汽蒸馏得到壬酸。
3. 将浓盐酸加入残液中回流1小时后冷却分出油层并加热至180℃，当停止放出二氧化碳时，反应物中的油状物即为粗品壬酸。减压蒸馏，收集140-142℃（1.6kPa）的馏分得到成品壬酸，收率约70%。
4. 也可以通过由壬醇或壬醛氧化获得，或者经甲基壬酮氧化而得。油酸也可经臭氧氧化制备。

以上方法中任一一种都能有效合成出所需的壬酸产品。