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United States Patent Office Patented M... 23, 1943 2,314,454. UNITED STATES PATENT OFFICE . 2,814,454 PRODUCTION orv Es'rEn's or HALOGEN awonons , I ' Friedrich Manchen and Willi Schmidt, Ludwigs haien-on-the-Rhine, Germany, assignors, by mesne assignments, to General Aniline & Film Corporation, New York, N. Y., 'a corporation of Delaware No Drawing. Application August 9, I939, Serial No. 289,174. In Germany August 19, 1938 7 Claims. (Cl. 260-463) The present invention relates to esters of halo ' also iodine, the reaction may readily be initiated gen alcohols and a process of producing same. and accelerated. , We have found that esters of halogen alcohols / The reaction in the liquid phase may also be are obtained in a simple manner by causing cyclic rendered continuous by allowing appropriate ethers of the dihydro and tetrahydrofurane series amounts of the initial materials to ?ow together to react with carboxylic acid halides including and then allowing the mixture to ?ow through a phosgene. tube system, for example, which is kept at the Cyclic ethers suitable as initial materials are in necessary temperature. particular tetrahydrofurane itself and dihydro ' The'process may also be carried out in the gas furane itself and their derivatives, as for example 10 .phase, when starting from acid halides, which ‘are 2.3-dichlortetrahydrofurane, and also their hom stable above their boiling point. In this case also ologues, as for example mono- and dl-alkylated ' it is possible to work with the aid of catalysts cli-hydrofuranes and tetraalkylated tetrahydro and/or in the presence of diluents. It is also iuranes, such as 2.5-dimethyltetrahydrofurane, possible to work under increased or reduced pres 2.2.5.5-tetramethyltetrahydrofurane, and also 15 sure. tetrahydroiurfuryl alcohol or oxetone. Among The compounds prepared according to this in carboxylic acid halides there may be mentioned vention may be used as solvents or as plasticizers acetyl chloride, acetyl bromide, acetyl iodide, for organic ?lm-forming materials. chloracetyl chloride, butyric acid chloride, lauric ,The following examples will further illustrate acid chloride, oleic acid chloride, benzoyl chloride 20 how this invention may be carried out in practice or phenylacetic acid chloride, and also the chlo but the invention is not restricted to these ex rides of polybasic carboxylic acids, such as suc amples. I The parts are by weight. cinic acid chloride or phthalyl chloride, and also Example 1 phosgene. 144 parts of tetrahydrofurane, to which a little The reaction proceeds, for example when start 25 ing from tetrahydrofurane and acetyl chloride, zinc chips or zinc dust has been added, are placed according to the following equation: in a ?ask provided with a re?ux condenser and then 158 parts of acetyl chloride are allowed to ?ow in slowly at room temperature. The reaction commences vigorously immediately. The tem 30 perature at ?rst rises slowly to 80° C. and towards the end of the reaction rapidly to 150° C. After C H: cooling, the reaction mixture is washed with dilute Dihydrofurane and acetylchloride react accord soda solution in order to remove small amounts ing to the following equation: ' of acetic acid formed; dried and distilled. There 35 are thus obtained :300 parts of 4-chlor-butyl acetate, boiling point from 92° to 94° C. at 22 millimeters (mercury gauge). The yield amounts to 99 per cent of the theoretical yield. 1 The reaction may also be carried out without C It 40 catalyst. In this case the mixture of the com Depending on the reactivity of the initial ma ponents is heated for,5 hours to 150°v C. in a terials, the reaction sets in more or less rapidly pressure vessel. By working up there is obtained and readily when the reactants are brought to 4-chlorbutyl acetate in an 85 per cent yield. gether in the liquid state. For example if tetra hydrofurane be mixed with acetyl chloride, the 45 ) Example 2 ~ reaction commences at room temperature with 432 parts of tetrahydrofurane are heated to the formation of 4-chlor-butyl acetate. Other about 100° C. Some magnesium chips are then carboxylic acid chlorides, as for example chlo- ‘ introduced and 420 parts of benzoyl chloride are rides of aromatic carboxylic acids. such as ben allowed to ?ow in. The reaction commences zoyl chloride, react less rapidly so that in this 50 slowly after a few minutes and then proceeds case the mixture of the initial materials is pref rapidly. When it is completed, the excess of erably heated. The reaction is often attended by tetrahydrofurane is distilled oil‘, the product great evolution of heat. In this case a diluent ' washed with sodium carbonate and .distilled. which does not impair the reaction, as for ex 4-chlorbutyl benzoate having a boiling point of ample aliphatic and aromatic hydrocarbons, may ' from 176° to 178° C. at 20 millimeters (mercury be used or an excess, of one of the initial ma gauge) is thus obtained in a 90 per cent yield. terials may be used. By adding catalysts, as for Example 3 example substances capable of promoting the splitting o? of hydrogen halide, such as zinc or 200 parts. of normal-butyric acid chloride are magnesium, zinc chloride, aluminium chloride or allowed to ?ow slowly into 140 parts 01' tetra 2 2,814,454 hydrofurane to which 1 part or anhydrous zinc Example 8 \ chloride has been added. The mixture heats up The vapors of 72 parts of tetrahydroiurane and slowly until at the end of thereaction it has at 80 parts of acetyl chloride are led through a tube tained a temperature of 150° C. By distillation, ?lled with glass beads and small pieces of metallic 4-chlorbutyl butyrate having a boiling point of zinc, 4-chlorbuty1 acetate is obtained in almost from 116° to 118° _C. at 21 millimeters (mercury a quantitative yield. gauge) is obtained in an 8'7 per cent yield. Instead of the said ?lling for the tube, there ' Example 4 may be used aluminium grit or metallic Raschig rings with or without admixture with indifferent A little anhydrous aluminium chloride is added 10 to 90 parts of 2.3-dichlortetrahydrofurane and ?llers, as for example glass rings or pumice. then 40 parts of acetyl chloride are slowly added. Example 9 By working up as described above, 2.3.4-trichlor Phosgene'is led at room temperature into 360 butyl acetate having a boiling point of from 154° parts of tetrahydrofurane to which a little zinc to 158° C. is obtained in a good yield. 15 has been added until further reaction cannot be Example 5 observed. At the end of the reaction the tempera ture of the reaction mixture is 60° C. The neutral 160 parts of acetyl chloride are allowed to ?ow carbonic acid ester of 4-chlorbutanol is obtained slowly into a solution of 140 parts or dihydro in a good yield. ‘ furane in 100 parts of benzene to which a small 20 What we claim is: amount of iodine has been added. By working 1. A process for the production of esters of halo up, 4-chlor-2.3-butenyl acetate having a boiling gen-alcohols which consists in bringing into con point 01' from 93° to 94° C. at 24 millimeters tact at reaction temperature a cyclic ether 01' the (mercury, gauge) is obtained in a good yield. dihydro- and tetrahydrofurane series with a car Example 6 25 boxylic acid halide. 2. A process for the production of esters of A little zinc is added to a mixture of 144 parts chlor-alcohols which consists in bringing into of tetrahydrofurane and 200 parts oi.’ toluene contact in the liquid phase at reaction tempera and then 203 parts 01' phthalylchloride are al ture a cyclic ether of the dihydro- and tetra lowed to run in. By working up the reaction mix ture, phthalic acid-4-chlorbutyl ester is obtained 30 hydrofurane series with a carboxylic acid chloride. - in a '75 per cent yield. 3. A process for the production of esters of Example 7 chlor-alcohols which consists in bring into con tact in the liquid phase at reaction temperature 157 parts of acetyl chloride are gradually added 35 a cyclic ether of the dihydro- and tetrahydro to a solution of 102 parts of tetrahydrofurfuryl furane series with acetyl chloride. ' alcohol in 200 parts of benzene. When the 4. A process for the production of esters of originally very vigorous reaction has moderated, a chlor-alcohols which consists in bringing into little zinc dust is added. When the reaction is contact in theliquid phase at reaction tempera completed, the reaction mixture is worked up in 40 ture tetrahydrofurane with acetyl chloride. the above-mentioned manner and an oily liquid 5. A process for the production of esters of boiling at from 158° to 160°‘ C. under a pressure halogen-alcohols which consists in bringing into of 26 millimeters (mercury gauge) and having contact in the liquid phase tetrahydrofurane with the composition -C9H15O4Cl is- obtained. The phosgene. compound probably corresponds to the con- I 6. A process for the production of esters of stitution: _ chlor-alcohols which consists in bringing into Cl.OHICH2CE2CH.CH2-0.CO-CHB contact in the liquid phase tetrahydrofurane with a carboxylic acid chloride. 0.00.011. 7. A process for the production of esters of - I 50 halogen-alcohols which consists in bringing a or cyclic ether of the dihydro- and tetrahydroiurane series into contact with phosgene at reaction CHaC0.0.CH:CH:CH:CH.CH:.O.C O.CH2 temperature. 1 FRIEDRICH MANCHEN. II 55 m SCHMDDT. .
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