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UNITED STATES PATENT of FICE 2,40,149 STABLIZED 2-CHLOR-BUTENE-2 Clyde B

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UNITED STATES PATENT of FICE 2,40,149 STABLIZED 2-CHLOR-BUTENE-2 Clyde B Patented Sept. 3, 1946 2,40,149 UNITED STATES PATENT of FICE 2,40,149 STABLIZED 2-CHLOR-BUTENE-2 Clyde B. Gardenier, Belleviiie, N. J., assignor to Thomas A. Edison, Incorporated, West Orange, N.J., a corporation of New Jersey No Drawing. Application September 8, 1944, Serial No. 553,280 6 Claims. (C. 252-364) 2 This invention relates to novel compositions of pounds that may be added thereto for this pur matter and to methods for preparing the same. pose are alcohols, amines, chloroform and the More particularly this invention is directed to like. The compounds which are added either stabilized 2 chlor butene 2 and to ninethods for alone or in combination to the 2 chlor butene 2 preparing the Sane. 5 must be capable of forming a solution therewith In the production of butadiene, one of the by and may be in the liquid, Solid or gaseous state. product fractions contains 2 chlor buttene 2 in These alcohols may be primary, secondary or both the cis and trans forms, 3 chlor buttene 1, tertiary alcohols and they may be saturated or and 1 chlor butene 2 having the following ac unSaturated by having one or more acetylenic cepted formulas respectively, CH3CCI:CHCH3, () Or ethylenic linkage. These alcohols may be CH2:CHCHCCH3, and CH3CH:CHCH2Cl. This monohydric or polyhydric. The amines may be fraction containing Said compounds, is a black primary, Secondary, or tertiary amines. Among liquid when it is about two weeks old and to the Some of the specific compounds that are particu best of my knowledge has found no application larly Suitable for this purpose and may be used and consequently practically all of it is dumped either alone or in combination are methyl al as a waste product. In the course of my experi cohol, ethyl alcohol, propyl alcohol, isopropyl mentation with said fraction, I have found that alcohol, chloroform, triethanolamine, phenyl al said fraction containing said metameric CCIn pha naphthylamine, amino methyl propanol, di pounds may be treated to provide products which phenyl guanidine, triisopropanol amine, hexa either alone or combined with other products are methylene amine and 2 amino 2 methyl propane useful. diol. The ratio by Weight of the stabilizer to the According to this invention, said fraction con 2 chlor buttene 2 is dependent on the stabilizer taining said metameric compounds is treated to employed. When the amines are so employed the selectively separate the primary and secondary ratio of Stabilizer to 2 chlor butene 2 may be as halides, namely, the is chlor butene 2 and the 3 low as 1 part amine to 10,000 parts 2 chlor butene chlor butene i from the 2 chlor buttene 2. This 2 by weight. When the alcohol or chloroform separation may be accomplished by selective re is employed, the volume ratio of the alcohol or action and precipitation and the resultant or chloroform to the 2 chlor buttene 2 should be at residual 2 chlor butene 2, which is Substantially least 5 to 100. I have discovered that 2 chlor free from said primary and Secondary compounds, butene 2 may be stabilized for varying lengths I have found may be used in some fields. This of time depending on the stabilizer, or combina resultant 2 chlor butene 2 has a specific gravity tion of Stabilizers employed. below at 25 C. and a boiling range of between While one or a combination of two or more of about 60° C. to 75° C. This resultant 2 chlor said stabilizers may be added to 2 chlor butene 2 butene 2 is a mixture of 2 chlor butene 2 trans :3 5 to stabilize the same, I prefer in certain in and 2 chlor butene 2 cis. While I have found stances, to first separate the 2 chlor buttene 2 that this resultant 2 chlor buttene 2, separated trans from the cis form and to maintain the 2 from said primary and secondary halides, has chlor buttene 2 trans in the presence of the sta certain properties, I have also found that it is bilizer in the course of and after this separation not stable and after left standing under normal 40 step thus to eliminate substantially entirely any conditions of temperature and pressure for about liability of degradation of 2 chlor butene 2 trans 24 hours, the pH thereof has decreased and it has during separation and for a substantial period become darker in color. The 2 chlor butene 2 thereafter. This I accomplish by adding to 2 exists only momentarily in the pure state due to chlor butene 2 cis and trans one or more of said the fact that it undergoes degradation due to alcohols and/or chloroform and this liquid lass hydrolysis thereof with the consequent production is then subjected to distillation and the fraction of HCl and other degradation productS. of the distillate boiling within about 59 C. and In the course of my experimentations with 2 64 C. and preferably within about 61° C. and 62 chlor buttene 2, I have discovered that the stability C. is separated and collected. These distillates I of 2 chlor buttene 2 either in the trans or cis form have found to be stable for at least 72 hours and or a mixture thereof in said different forms Inay the 2 chlor butene 2 therein is substantially con be considerably improved. I have found that 2 pletely in the trans form and will remain for at chloributene 2 may be maintained substantially least 72 hours in that form free from degrada free from degradation products thereof for con tion products as evidenced by lack of any change siderable periods of time. Among the many con 55 of color or pH in that period. While the quantity 2,407,149 3 4. by volume of said alcohols or chloroform in said mass being distilled may vary, it should be at Table II least 5% by Volume of the mass and its maximum Parts (volume) limit may be of any desired value depending 2 chlor butene 2-------------------------- 00 upon the end product desired. When one of said Isopropyl alcohol---------------------- 5 to 25 alcohols or chloroform is used alone with said 2 chlor butene 2 to separate the trans from the cis Table III as above set forth, I have found that the stabil Parts (volume) ity of the 2 chlor buttene 2 in the distillate is lin 2 chlor butene 2-------------------------- 1.00 ited in time and that the time of stability may 10 Chloroform------------------------ 10 to 1000 be greatly increased by adding thereto a quantity Isopropyl alcohol at least 5% to the combined of an amine which is soluble therein and exam volumes of 2 chlor butene 2 and chloroform, ples of which have been heretofore set forth. the upper limit being dependent upon the dilu The quantity of said amine added to said distill tion with isopropyl alcohol desired late may be as low as 1 part by Weight of the 5 Instead of employing isopropyl alcohol, any of amine to 10,000 parts by weight of the distillate, the other alcohols and preferably methyl, ethyl and of Course it may be much higher if desired. or propyl alcohol may be substituted therefor in By adding Such small amounts of one or more Tables II and III and the proportions are main Said amines to said distillates, the time of stabil tained as set forth in said tables. However, I ity of the 2 chlor butene 2 trans therein may be 20 prefer to employ isopropyl alcohol as the alcohol. Considerably increased. When one or more of While the products of Tables I and II are stable the alcohols and chloroform are employed to for a period of at least a week, the products of gether With the 2 chlor butene 2, I have found Table III are stable for months and apparently that the resulting distillate is stable for a longer for an indefinite period of time without adversely period of time than the distillate containing no 25 affecting the anesthetic properties thereof. chloroform. In accordance with my novel method, the In the practice of this invention; I prefer that aforementioned by-product fraction containing the ratio of the 2 chlor butene 2, whether in the the metameric compounds 2 chlor butene 2 in trans or cis form or as a mixture of the trans and both the trans and cis forms, 3 chlor buttene 1 cis forms, to the chloroform whether used alone 30 and 1 chlor buttene 2 may be employed as the or in combination with one or more of the alco starting raw material. To said by-product frac hols and preferably methyl, ethyl, propyl and tion is added a quantity of an alcoholic Solution isopropyl alcohol, be between about 10 to 1 and 1 of sodium or potassium hydroxide. I prefer to to 10 parts by volume and to the alcohol whether employ sodium hydroxide and the quantity there Used alone or in combination with the chloro 35 of in ethyl alcohol is between 25% to 50% form be no greater than about 20 to 1, with the in excess of that required to react with all of the lower limit being any desirable amount depend primary and secondary halides present in said ing upon the dilution required with the alcohol. fraction. Upon the addition of said alcoholic so This invention accordingly comprises the sev lution of sodium hydroxide to said fraction, there eral steps and relation of one or more of such 40 is a reaction between the Sodium hydroxide and steps with respect to each of the others, and com the primary halide whereupon the sodium de positions of matter possessing the characteristics, rivative of the primary halide precipitates out.
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