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3. Acyl chloride is an important carboxylic acid derivative, which has important applications in organic synthesis, drug synthesis, etc. It mainly includes hydrolysis, alcoholysis, ammonolysis, reaction with organic metal reagent, primary reaction α Hydrogen halogenation and other reactions acyl chloride splashing acylation reagent limit structure resonance hybrid species resonance effect stability enhancement carbonyl carbon and free group bond resonance effect species stability effect depends on the bond original orbital cross cover acyl chloride is affected by species resonance energy species resonance need carbon 2p orbital and chlorine 3P orbital cross cover two kinds of orbital same cross cover CL structure (Ⅱ) contribution acyl chloride is stabilized e to resonance effect Acyl chloride splashing acylation reagent some carboxylic acids can carry out or non slow reaction. Carboxylic acid can proce acyl chloride to improve the reactivity yield. At present, SOCl2, phosphorus trichloride, phosphorus pentachloride and triphosgene are used to prepare acyl chloride. In this paper, 1 dichlorosulfoxide 1.1 dichlorosulfoxide acyl chloride can be prepared by using fatty acids (including saturated fatty acids), aromatic acids, organic sulfonic acids (amino acids, halogenated acids, etc.) as catalyst N, N-dimethylformamide (DMF), N, Generally, N-dimethylaniline pyridine reacts with catalyst first, and then reacts with carboxylic acid. Acyl chloride (1) trimethylacetic acid lactam reacts with thionyl chloride. The yield of trimethylacetyl chloride is 96% (CH3) 3ccooh → (SOCl2 lactam) → (CH3) 3cocl (2) (m) benzenedicarboxylic acid thionyl chloride. Two kinds of procts are mainly used for organic synthesis, and plasticizers are widely used at present Diisooctyl phthalate (DOTP) diisooctyl phthalate raw material (3) o-chlorobenzoic acid thionyl chloride reaction o-chlorobenzoyl chloride this proct is mainly used for organic synthesis and pharmaceutical dyestuff synthesis (4) butyl (heptyl, octyl, decanoic) acid thionyl chloride reaction to prepare butyl (heptyl, octyl, decanoic) acid Four procts are used in the synthesis of pharmaceutical intermediates CH3 (CH2) ncooh → (SOCl2) → CH3 (CH2) ncocln = 4-20 (5) stearic acid chlorinated sulfoxide to proce stearic acid chloride. They are used in the synthesis of skincare procts bisstearic acid kojic acid ester to prepare papermaking instrial sizing agent - AKD (6) organic sulfonic acid catalyst. The sulfonyl chloride is prepared by the reaction with thionyl chloride Sulfonic acid sodium reacts directly with thionyl chloride sulfonyl chloride 1.2 advantages and disadvantages of preparing acyl chloride by thionyl chloride; In addition, the proction cost of sulfoxide chloride is high and the corrosion of equipment is serious. 2. The reaction of phosphorus trichloride (1) propionic acid and phosphorus trichloride is propionyl chloride. The reaction formula is ch3ch2cooh → (PCl3) → ch3ch2cocl. Propionyl ammonia is mainly used in combination with anticonvulsant drugs such as Metoprol, cholesterol, etc (2) reaction of lauric acid with phosphorus trichloride lauroyl chloride reaction: 3c11h23cooh + PCl3 → 3c11h23cocl + h3po3 this proct is used for the synthesis of sodium dodecyl lauroyl amino acid acetals (3) reaction of oleic acid with phosphorus trichloride to proce oleoyl chloride reaction: CH3 (CH2) 7 (CH2) 7coohpcl3ch3 (CH2) 7 (CH2) 7cocl & gt; C=C=C< Hhnaohhh this proct is mainly used in the detergent LS (c25h40nnao5s) 204 for the preparation of organic compounds. It is used to prepare acyl chloride from phosphorus trichloride. It is suitable for the preparation of low boiling point acyl chloride reaction. Phosphite is easy to volatilize and evaporate acyl chloride 3. Phosphorus pentachloride (1) oxalic acid reaction to prepare oxalyl chloride reaction: coohpcl5cocl ∣ →∣ + 2pocl3 + hclcoohcocl. The pharmaceutical surface of this proct is used as antibiotic raw material and used as methacryloyl isocyanate (2) succinic acid reacts with phosphorus pentachloride to form succinyl chloride: ch2coohpcl5ch2cocl ∣ →∣ + POCl3 + h2och2coohch2cocl this proct is used for synthesis of antiepileptic and antispasmodic drugs succinylcholine chloride resin intermediate phosphorus pentachloride is suitable for preparation of high boiling point acyl chloride, POCl3 evaporated, 4 triphosgene triphosgene, high melting point, low volatility and low toxicity, even if boiling point Only a small amount of instrial toxic substances need to be treated and participate in the chemical reaction, with high selectivity and high yield. It is safe and convenient to use, and easy to transport and store medicines, pesticides It is widely used in the synthesis of related chemical procts that phosgene or biphosgene is completely replaced by high-quality materials in mechanochemical instry. 4.1 ring the application, 5 carboxylic acids are chlorinated with triphosgene (1) c6h5-ch2cooh + 1 / 3btc → (dmf60 ℃) → c6h5-ch2cocl + CO2 + HCl in 71% yield (2) ch3-c6h4-cooh + 1 / 3btc → (dmfch2cl2) → ch3-c6h4 + cocl4.2- 5-chloroformyloxy-isopeptidyl chloride (CFIC) was prepared by triphosgene reaction with hydroxyisophthalic acid composite catalyst. The yield of CFIC was 42.3%, which was 9.7% and 27.7% higher than that of DuPont hydraulics patent, The yield of 3-dichloroquinoline-6-carboxyacyl chloride is 80%. 5 kinds of oxalyl chloride are used for acylation of acids and amines to prepare pesticides, fungicides, pharmaceutical antineoplastic agents, X-ray contrast agents, etc The transportation and storage of phosgene are dangerous. The transportation and storage of phosgene are safer than phosgene. It is a kind of highly toxic and pungent liquid It is still dangerous to store. 6.3 the reaction of carbohydrates with CCl4 often requires the preparation of acyl chloride. The yield of acyl chloride is usually low in the traditional way. However, the preparation of acyl chloride with CCl4 triphenylphosphine system has a good yield. The reaction mechanism is: (C6H5) 3P + CCl4 → (C6H5) 3 + pccl3cl - Ⅰ + rcooh → rcoo + P (C6H5) 3 + hccl3 Ⅱ → rcocl + (C6H5) 3PO Comparison of the use efficiency of acid sensitive compounds in acid substances such as SO2 6.4 Hexachloroacetone Although the preparation of acyl chloride has been widely used, it plays a decisive role in the development of synthesis.
is there any by-proct of acyl chloride made from acid in esterification
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