制备乙酰苯胺-Preparation of Acetanilide

EXPERIMENT D-18 Preparation of Acetanilide
Introduction
The acylation of an amine is a Lewis-type acid base reaction in which the basic amino group makes a nucleophilic attack upon a carbonyl carbon atom that is the acidic center.The reaction ,in general,proceeds most rapidly with acid chlorides,slower with acid anhydrides,and so slowly with acids themselves that an elevated temperature is required.In the commercial manufacture of acetanilide,for example,a mixture of aniline is boiled for 6 to 8 hours.A warm solution of acetic and acetic anhydrides reacts with amino compounds at a rate that is often suitable for laboratory purposes,and this alternative has been selected for today's experiment. Experimental
Into a 100 mL flask introduce 9 mL(0.1 mol)of aniline,15 mL glacial acetic acid,and 15 mL acetic anhydride.Note that heat is evolved owing to the reaction of acetic anhydride with aniline.Attach the flask to a reflux condenser and heat the solution to boil for 10 minutes.At the end of the time,cool the flask somewhat under the water faucet and pour its contents into a beaker containing about 50 mL water and 40~50g ice.Stir the mixture well and collect the crystal of acetanilide upon a Buchner funnel.
Rinse the crystal on the filter with a little cold water and transfer them to a 600 mL beaker for recrystallisation.Add 200 mL water and heat the mixture until the water is boiling.If all of the acetanilide does not dissolve,add another 50 mL water and again heat to boil.(Note 1).Remove the beaker from the flame,allow the contents to
cool for a moment,and add 1~2 grams of decolorizing carbon(Note 2).Again heat the solution to boil,stir well,and filter through a funnel fitted with a hot water. Note 1:The solubility of acetanilide is 5.55 percent at 100°C;3.45 per cent at 80°C;0.84 percent at 50°C;0.45 percent at 20°C.
Note 2:The addition of finely divided carbon (to other substance,for that matter)to the solution at the boiling point often causes the solution to boil over.
Chill the filter in ice,collect the crystal of Buchner funnel,and press out as much water as possible.Shut off the suction pump and stir the crystal on the filter with 5 mL cold ethanol.Suck the alcohol through the filter,again shut off the pump and stir the crystals gently with 10 mL ether.Draw the ether through the filter and spread the crystals on a sheet of paper to dry in the air. As an alternative procedure to rinsing with alcol and ether,the moist acetanilide may be dried in an oven at 50~60°C.Yield 8~10g m.p 113~115°C
Questions
May acetanilide be considered to be the N-phenyl derivative of acetamide? Can acetamide be made by heating ammonium acetate? Can acetamide be made by heating ammonium acetate? Can acetamide be made by heating phenyl ammonium acetate?
What is the commercial method for the manufacture of acetanilide?
实验d 18制备乙酰苯胺
介绍
这个反应是路易斯酸的亲核加成反应。

反应中,一般来说和乙酰氯化物反应最快,与酸酐反应较慢,和乙酸反应更慢。

所以加热是必需的。

在商业生产中，苯胺与乙酸加热6到8个小时。

由于乙酰氯和酸酐与苯胺的反应速度,为了适合实验室的目的,乙酸作为今天的实验的选择。

实验
向100毫升烧瓶加入9毫升(0.1摩尔)苯胺、15毫升冰醋酸和15毫升醋酐。

注意,乙酸酐与苯胺的反应温度。

加热沸腾后回流10分钟。

最后，倒入含约50毫升的水和40 ~ 50 g冰的烧杯中。

搅拌抽滤。

冷水冲洗晶体并转移到600 mL烧杯中重结晶。

加入200毫升水,加热混合物直到沸腾。

如果不溶解,再加另一个50毫升的水加热沸腾。

(注1)移除加热烧杯的火焰,可以冷却,并添加1 ~ 2克的活性碳(注2)再次加热溶液煮沸,用热水搅拌和过滤。

注1:乙酰苯胺的溶解度在100°C是5.55%;3.45%在80°C;0.84%在50°C;0.45%在20°C。

注2:过滤碳(忽视其他杂质),以解决到达沸点后常常引起的爆沸问题。

用冰水将滤液冷却。

关闭泵，并压干。

用5毫升冷乙醇洗涤。

抽干乙醇后,再关闭泵,轻轻搅拌晶体与10毫升醚。

将产物转移到纸上在空气中干燥。

也可以将潮湿晶体在烤箱50 ~ 60°C烘干。

产物约8 ~ 10 g熔点113 ~ 115°C
问题
1、乙酰苯胺可以看作是乙酰胺的苯基衍生物吗?可以由加热醋酸铵制得乙酰胺吗可以由加热乙酰苯胺的方法制乙酰胺吗?
2、工业方法怎么制造乙酰苯胺吗?。