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甲缩醛
甲缩醛 · 二甲醇缩甲 · 甲醛缩二醇 · 二甲氧甲烷 · 甲撑二甲醚 · 二甲醇縮甲醛 · 二甲醇缩甲醛 · 二甲氧基甲烷
标识与物理属性
| CAS No. | 109-87-5 |
|---|---|
| 分子式 | C3H8O2 |
| 平均分子量 | 76.09 g/mol |
| 单同位素质量 | 76.0524295 g/mol |
| SMILES | COCOC |
| InChIKey | NKDDWNXOKDWJAK-UHFFFAOYSA-N |
| PubChem CID | 8020 |
| ChEMBL | CHEMBL15537 |
| ChEBI | CHEBI:48341 |
| EC No. | 203-714-2 |
| DTXSID | DTXSID1025564 |
| 中文名 | 甲缩醛 |
化学与物理性质
| XLogP | 0.2 |
|---|---|
| 极性表面积 | 18.5 |
| 氢键供体 | 0 |
| 氢键受体 | 2 |
| 可旋转键 | 2 |
| 重原子 | 5 |
| 形式电荷 | 0 |
| 复杂度 | 12.4 |
| 物质类别 | Other Classes -> AcetalsFlammable agents - 3rd degreeVolatile Organic Compound (VOC) |
| 化妆品 | Solvent |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（油水分配系数） | log Kow= 0.00.18 |
| 气味 | CHLOROFORM ODORChloroform-like odor.Mild, etherealchloroform-like. |
| 味道 | PUNGENT TASTE |
| 密度 | 0.861 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8593 @ 20 °C/4 °C0.86 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.70.8593 @ 20°C0.860 g/mL at 20 °C(lit.) |
| 食用香料 | EU Flavoring substances |
| Color/Form | COLORLESS, CLEAR LIQUIDColorless solid. |
| 溶解性 | 33 % (NIOSH, 2024)MISCIBLE WITH ALCOHOL, ETHER, OILSSOL IN 3 PARTS WATERSOL IN ALL ACETONE, AND BENZENEWater solubility: 330,000 mg/lSolubility in water, g/100ml at 20 °C: 28.5 (good)33%32.3 g/100 mL (16°C)32.3 g/100 mL (16 ºC) |
| 闪点 | 0 °F (USCG, 1999)-32 °C-26 °F (-32 °C) (OPEN CUP)-31 °C c.c.-26 °F (open cup)(oc) -26 °F-18 °C |
| 沸点 | 108 °F at 760 mmHg (USCG, 1999)41.6 °C @ 760 MM HG42 °C111 °F42 °C @760 [mm Hg]41-43 °C |
| 熔点 | -105 °C |
| 蒸气密度 | 2.6 (vs air) |
| 蒸气压 | 6.38 psi ( 20 °C) |
| 折射率 | n20/D 1.354 |
| 储存条件 | Store at <= 20°C. |
| 形态 | Liquid |
| pKa（酸度系数） | 3.1[at 20 ℃] |
| 颜色 | Clear colorless |
| pH | pH (12.5vol % , 25℃) : 4.5～6.6 |
| 爆炸极限 | 1.6-17.6%(V) |
| 比热容 | Cp(liquid): 2.13 J/(g·K), at 25℃ |
| 敏感性 | Moisture Sensitive |
| Merck | 14,6012 |
| BRN | 1697025 |
| 亨利常数 | (x 10-4 atmm3/mol): 1.73 at 25 °C (Hine and Mookerjee, 1975) |
| 暴露限值 | ACGIH:TLV-TWA 1000 ppm (3110 mg/m3)OSHA:PEL-TWA 1000 ppm (3100 mg/m3)NIOSH:REL-TWA 1000 ppm |
| 介电常数 | 2.7(20℃) |
| 稳定性 | Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point and wide explosive limits. Incompatible with strong oxidizing agents, strong acids. May form explosive peroxides upon exposure to air. |
| 化妆品成分功效 | SOLVENT |
| InChI | 1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3 |
| InChIKey | NKDDWNXOKDWJAK-UHFFFAOYSA-N |
| SMILES | COCOC |
| LogP（油水分配系数） | 0 |
| CAS 数据库 | 109-87-5(CAS DataBase Reference) |
| NIST化学物质信息 | Methane, dimethoxy-(109-87-5) |
| EPA化学物质信息 | Dimethoxymethane (109-87-5) |
化学性质
无色澄清易挥发可燃液体，有氯仿气味和刺激味。 溶于3倍的水[20℃时水中溶解度32%（重量）]。与多数有机溶剂混溶。
安全与法规
| GHS 分类 | This chemical does not meet GHS hazard criteria for 1.2% (5 of 433) of reports.DangerH225 (98.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 433 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 法规信息 | Chemical: Methane, dimethoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Methane, dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, dimethoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 27-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5159Methane, dimethoxy-: HSNO Approval: HSR001047 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 运输标签（DOT） | Flammable Liquid |
| 火灾危害 | FLAMMABLE. Irritating gases may be produced when heated. Containers may explode in fire. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Irritating formaldehyde gas may be present in smoke. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Heating will cause rise in pressure with risk of bursting. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with strong oxidizing agents or strong bases. |
| 火灾可能性 | DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OXIDIZERS |
| 健康危害 | VAPOR: Irritating to eyes, nose and throat. Harmful if inhaled. LIQUID: Irritating to skin and eyes. Harmful if swallowed. (USCG, 1999)· Inhalation or contact with material may irritate or burn skin and eyes. |
| 危害概述 | Animal inhalation studies: anesthesia and damage to the liver and other organs[ACGIH] A skin, eye, and respiratory tract irritantInhalation of high concentrations can cause CNS depression[ICSC] |
| 运输编号与指南（DOT） | 1234 127 |
| 反应性基团 | Acetals, Ketals, Hemiacetals, and Hemiketals |
| 联合国分类 | UN Hazard Class: 3UN Pack Group: II |
| TSCA 要求 | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Methane, dimethoxy- is included on this list. |
| Reactivity Alerts | Highly Flammable |
| OSHA Standards | 8 hr Time-Weighted avg: 1,000 ppm (3,100 mg/cu m) |
| 消防 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Use water spray, dry powder, carbon dioxide, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water. |
| 急救措施 | Fresh air, rest. Refer for medical attention.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Refer for medical attention . |
| 泄漏应急措施 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 急救 | Excerpt from NIOSH Pocket Guide for Methylal:General First Aid:(General first aid procedures) |
| 安全储存 | Fireproof. Separated from strong oxidants and strong bases. Cool. Keep in the dark. Well closed. Store only if stabilized. Store in an area without drain or sewer access. |
| 暴露控制与个人防护 | · Wear positive pressure self-contained breathing apparatus (SCBA).500.0 [ppm] |
| 灭火程序 | TO FIGHT FIRE: FOAM, CARBON DIOXIDE, DRY CHEMICAL ...Water may be ineffective. Alcohol foam. |
| 清理方法 | 1. REMOVE ALL IGNITION SOURCES. 2. VENTILATE AREA OF SPILL OR LEAK. 3. FOR SMALL QUANTITIES, ABSORB ON PAPER TOWELS. EVAPORATE IN SAFE PLACE (SUCH AS FUME HOOD). ALLOW SUFFICIENT TIME TO COMPLETELY CLEAR HOOD DUCTWORK. BURN PAPER IN SUITABLE LOCATION AWAY FROM COMBUSTIBLE MATERIALS. 3. LARGE QUANTITIES CAN BE COLLECTED, DISSOLVED IN ALC OF GREATER MOLECULAR WT THAN BUTYL ALC, & ATOMIZED IN SUITABLE COMBUSTION CHAMBER. METHYLAL SHOULD NOT BE ALLOWED TO ENTER CONFINED SPACE, SUCH AS SEWER, BECAUSE OF THE POSSIBILITY OF AN EXPLOSION. |
| 非火灾泄漏应对 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| 处置方法 | ... MAY BE DISPOSED OF BY DISSOLVING IN ALCOHOL OF GREATER MOLECULAR WEIGHT THAN BUTYL ALCOHOL & ATOMIZING IN SUITABLE COMBUSTION CHAMBER. |
| 泄漏处置 | Consult an expert! Personal protection: filter respirator for organic vapours of low boiling point adapted to the airborne concentration of the substance. Remove all ignition sources. Cover the spilled material with sand or other non-combustible material. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature supports the wearing of contact lenses in industrial environments, as part of a program to protect the eye against chemical compounds and minerals causing eye irritation. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases contact lenses should not be worn.SAFE-HANDLING PRECAUTIONS SHOULD INCL USE OF ADEQUATE VENTILATION TO BE CERTAIN THAT AVG CONCN ARE WELL BELOW 1000 PPM, & AVOIDANCE OF EXCESSIVE OR PROLONGED SKIN CONTACT. METHYLAL SHOULD BE HANDLED WITH DUE REGARD FOR ITS FLAMMABLE PROPERTIES.To prevent injury from occurring as a result of contact with an aldehyde in the form of liquid or vapor, the process in which the substance is present should, if possible be conducted in enclosed plant. If openings are necessary for the purposes of manipulation, vapor should be prevented from escaping into the workroom by the application of exhaust ventilation to the plant or enclosure. When the process cannot be enclosed, exhaust ventilation hoods should be fitted to trap and extract escaping vapor before it can diffuse into the workroom atmosphere. /Aldehydes and ketals/The worker should immediately wash the skin when it becomes contaminated.Work clothing that becomes wet should be immediately removed due to its flammability hazard. |
| 体内负荷 | In the EPA National Human Adipose Survey for fiscal year 1982, 46 composite samples categorized broadly by region and age group were analyzed for pollutants(1). Methylal was identified in one sample from the northeast US in the >45 age group. |
| 靶器官 | Eyes, skin, respiratory system, central nervous system |
| 环境归趋 | TERRESTRIAL FATE: If released on land, methylal would volatilize rapidly due to its high vapor pressure and Henry's Law constant and low adsorptivity to soil. It would also exhibit high mobility in soil. The importance of biodegradation in soil is unknown. (SRC)AQUATIC FATE: If released to water, methylal will be primarily lost through volatilization. Its half-life in a model river is estimated from a calculated Henry's Law constant to be 7.2 hr(1-3). Adsorption to sediment and particulate matter in the water column, and bioconcentration should not be important. The importance of biodegradation in water is unknown. Hydrolysis is fairly slow(SRC).ATMOSPHERIC FATE: The atmosphere is the sink for methylal. In the atmosphere, methylal will degrade by reaction with photochemically-produced hydroxyl radicals. The half-life for this reaction is estimated to be 2.3 days(1). Methylal is highly soluble in water, 2.44X10+5 ppm(2), and would be washed out by rain. However, methylal thus remove would be recycled back into the atmosphere. (SRC) |
| 不良影响 | Neurotoxin - Acute solvent syndrome |
| 暴露途径 | The substance can be absorbed into the body by inhalation of its vapour.inhalation, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Dizziness. Drowsiness. Headache. Sore throat. Unconsciousness.Dry skin.Redness. Pain.Abdominal pain. Nausea. Vomiting. Further see Inhalation.irritation eyes, skin, upper respiratory systemanesthesia |
| Effluent Concentrations | In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, methylal was identified in discharges of the following industrial category (positive occurrencesmedian concn in ppb): leather tanning (11637.5), plastics and synthetics (330.8), organic chemicals (645.6), publicly owned treatment works (35.0)(1). The highest effluent concn was 1637 ppb in the leather tanning industry(1). Detected in effluent concentrates from the advanced treatment plant in Orange County, CA, but not in that of five other communities(2). |
| ICSC Environmental Data | Environmental effects of the substance have been adequately investigated, but no significant effects have been found. |
| Soil Adsorption/Mobility | The Koc for methylal estimated from its water solubility, 2.44X10+5 ppm(1), by a recommended regression equation is 5(2). Therefore methylal would be very mobile in soil(3). |
| Human Toxicity Excerpts | ... PROPERTIES OF SIMPLE UNSUBSTITUTED ACETALS ARE CHARACTERIZED BY ETHER-LIKE ANESTHETIC ACTION, & BY RELATIVELY LOW DEGREE OF PRIMARY IRRITATION COMPARED TO PARENT ALDEHYDE. /ACETALS/INHALATION CAUSES IRRITATION OF RESP SYSTEM & DEPRESSION OF CNS. LIQ CAUSES IRRITATION OF EYES & WILL IRRITATE SKIN IF ALLOWED TO REMAIN. |
| Artificial Pollution Sources | Methylal used as a solvent and reagent in organic synthesis(2) may be released to the environment in waste water and as fugitive emissions relating to its manufacture and use. Mean vapor emission rates of methylal measured at two locations at an industrial waste water treatment facility in December were 28.6 and 14.7 mg/min sq-m, at which time the ambient and liquid surface temperatures were 6 and 15 °C, respectively(1).METHYLAL WAS ONE OF THE COMPONENTS IN WASTE WATER FROM A UREA-FORMALDEHYDE GLUE PLANT. |
| Environmental Biodegradation | A reduction in BOD in 8 hr was obtained in one study in which well acclimated sewage seed was incubated with 333 ppm of methylal(1). However this reduction was small compared with the theoretical oxygen demand and toxicity resulted in an initial increase in BOD. |
| F | 21 |
| 水危害等级（WGK） | 1 |
| TSCA 清单状态 | TSCA listed |
| 毒性 | LD50 orally in Rabbit: 6653 mg/kg |
| RTECS 号 | PA8750000 |
| 包装类别 | II |
| 危险类别 | 3Flam. Liq. 2 |
| 储存类别 | 3 - Flammable liquids |
| 安全说明（S） | 16-26-33-7/9-37/39 |
| 海关编码 | 2911 00 00 |
| 自燃温度 | 459 °F |
| 危险品标志 | F,Xi |
| 危险类别码（R） | 11-19-36-36/37/38 |
| 毒害物质数据 | 109-87-5(Hazardous Substances Data) |
| 职业暴露等级（OEB） | A |
| 职业暴露限值（OEL） | TWA: 1000 ppm (3100 mg/m3) |
| 运输编号（UN） | UN 1234 |
| 立即危及生命和健康浓度 | 2,200 ppm [10% LEL] |
急性毒性
吸入-大鼠 LC50: 47 克/立方米; 吸入-小鼠 LC50: 57 克/立方米/7小时
刺激数据
眼睛-兔 0.1 毫升 中度
职业标准
TLV-TWA 3100毫克/立方米; STEL 3900毫克/立方米
爆炸物危险特性
与空气混合形成爆炸性混合物
可燃性危险特性
; 火场释放辛辣刺激烟雾
储运特性
库房通风低温干燥; 与氧化剂, 酸类分开储运存放
灭火剂
干粉, 泡沫, 二氧化碳, 1211
用途与应用
用途
二甲醇缩甲醛主要用于生产阴离子效换树脂，也作溶剂和特种燃料。其溶解能力比乙醚、丙酮强，和甲醇和共沸混合物能溶解含氮量高的硝化纤维素。但由于其蒸气有较强麻醉性，不宜作一般溶剂使用，通常作特殊声合的溶剂。还用于香料制造、生产人造树脂，用作格利雅反应和雷帕（合成）反应的反应介质。
用途
用于生产阳离子交换树脂和溶剂等
用途
用作溶剂、分析试剂 溶解特性，与醇醚丙酮等混溶，能溶解大多数树脂，溶解能力较强。是卤代烃和DMF较好的替代品。16度时在水中溶解32.3%因此可用在开发的水性涂料和胶粘剂。应用：已经在气雾剂、涂料、合成皮革、汽车上光剂、皮革上光剂、UV上光剂、磨光油、覆膜胶、万能胶、喷胶、空气清新剂、天那水中得到广泛的应用。
制备与合成方法
生产方法
在浓硫酸催化下，甲醇和甲醛在合成塔中反应。生成的甲缩醛从塔丁馏出，塔丁温度控制在41.5-42℃，从产物中分离未反应的甲醇供循环使用，得含量为85%以上的二甲醇缩甲醛。每吨产品消耗甲醇1100kg，37%的甲醛1300kg。产品二甲醇缩甲醛中的杂质主要是甲醇和甲醛，当要求较高纯度时，可用碱性过氧化氢氧化除去甲醛，加金属钠蒸馏可除去甲醇。