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US3534106专利译文

US3534106专利译文
US3534106专利译文

3,534,106

METHOD OF PRODUCING MERCAPTANS FROM OLEFINS AND ALCOHOL FREE HYDROGEN SULFIDE

它从生产方法和酒精自由烯烃氢硫化物

Paul F. Warner, Borger, Tex., assig丑or t~av~:llelips Petroleum Company, a corporation of Delav~

No Drawing. Filed May 2, 1967, Ser. No. 635,349

Int. CI. C07c 149/06 3,534.106 Patented Oct. 13, 1970

U.S. CI. 260-609 . 8 Claims

ABStIRACT OF rIHE DISCLOSURE

Removal of an alcohol from a gas or vapor, e.g., .methanol, from a hydrogen sulfide gas by contacting the gas with boron trifluoride. This method is particularly applicable to a method for converting a hydrogen sulfide containing gas to a mercaptan by reaction of said gas with an olefin as in the presence of a mercaptan synthesis .catalyst, e.g., an AI203 and S102 containing catalyst such as a silica-alumina catalyst or one prepared from montmorillonite. In one embodiment adding the boron trifluoride to the system at about the time catalyst activity tends to fall off and in another adding it to the hydrogen sulfide gas prior to the contact of the same with said olefin and/or said catalyst. 去除酒精从气体或蒸汽,例如,。甲醇,从硫化氢气体的气体,而且能处理硼trifluoride联系。该方法特别适用于转换方法,硫化氢含气反应气体的硫醇说与烯烃在存在一个硫醇合成。催化剂,例如,一个AI203含有催化剂和S102等催化剂或一个来制备了矽改性。在一个体现三氟化硼加入硼系统就在催化剂活性趋于脱落,在另一个增加到硫化氢气体的联系之前,也用说烯烃和/或说的催化剂。

This invention relates to the removal of an alcohol from a gas or vapor. 本发明涉及一种以去除乙醇气体或蒸气。

This invention further relates to the treatment of a hydrogen sulfide gas. It also relates to the preparation of a mercaptan from hydrogen su壕de and an olefin. Further, it relates to the treatment of a hydrogen sulfide gas to remove therefrom an alcohol which is undesirable therein,

In one of its concepts the invention proyides a method for the removal of an alcohol from a gas or vapor by contacting said gas or vapor with boron trifiuoride.

In another of its concepts, the invention provides a method for the removal of an alcohol from a hydrogen sulfide containing gas by contacting said gas with boron trifiuoride. In another of its concepts, the invention provides a method for the conversion of a hydrogen sulfide containing gas also containing an alcohol which has an adverse action upon a mercaptan synthesis catalyst by treating said gas with 'ooron trifiuoride, at least during, but preferably prior to the contact of said gas with said mercaptan synthesis catalyst and/or with an olefin or other compound which may be used.

In the synthesis of mercaptan employing a mercaptan synthesis catalyst such as Filtrol (a trademark) using a plant grade hydrogen sulfide gas resulting from the production of natural gas liquids, there will be trsually present in the gas during the winter months an alcohol, e.g., methanol, which is used to prevent freeze up in the gas gathering system. The alcohol concentrates in the amine scrubber which, as is known, is employed to remove hydrogen sulfide from the natural gas. Subsequently, when the hydrogen sulfide is stripped from the spent amine solution, the alcohol will be found in the hydrogen sulfide. Alcohol is a severe poison for mercaptan synthesis catalyst such as Filtrol catalyst or other catalysts, such as silica-alumina catalysts. Thus, at times methanol content of an incoming hydrogen sulfide stream may be as hi~ as 10 0r more weight percent and usually will be in the range of from about O.l to about l weight percent. Even at these low concentrations, a Filtrol catalyst can be used only for a short period before olefin conversion drops .to an uneconomic and the catalyst must be discarded. Thus, in thmeicyltaeeri! of mercaptans for example tert-mercaptans employing a catalyst as herein disclosed, it is desirable to effect an improvement.

I have now found that the addition of an amount of gas, preferably approximately equal in weight to the methanol content, will form a complex with the methanol in the gas and that this complex is in its own right suit able for synthesis of mercaptans. Thus, instead of poisoning the Filtrol catalyst, or other catalyst, the methanolboron trifluoride complex serves to enhance the catalytic ability of the Filtrol. Indeed, where catalytic activity of the catalyst has substantially declined due to the presence of alcohol in the hydrogen sulfide gas, it is possible, upon the addition of boron trifluoride thereto, to substantially regain a high conversion rate. Thus, it is possible to add the boron trifluoride to the hydrogen sulfide gas or to a mixture of it with one or more olefins prior to contact of the gas or gases with the mercaptan synthesis catalyst or to add the boron trifluoride directly to the catalyst containing zone.

It is an object of this invention to sequester or to remove an alcohol from a gas or vapor containing the same. It is another object of this invention to sequester or to remove an alcohol from a hydrogen sulfide containing gas. It is another object of this invention to prevent the poisoning of a mercaptan synthesis catalyst by alcohol contained in a hydrogen sulfide gas which is

passed to said catalyst to there react with an olefin to form a mercaptan. It is another object of this invention to provide

a method for increasing or enhancing the efficiency of a mercaptan synthesis catalyst. It is a further object of this invention to revitalize a mercaptan synthesis catalyst which has been poisoned by an alcohol. Other concepts and objects of this invention are apparent from a study of this disclosure and the appended claims.

According to the present invention, an alcohol such as methanol is removed from a gas or vapor containing the same, e.g., hydrogen sulfide containing gas by contacting said gas with boron trifiuoride.

The alcoholis usually one employed to prevent freeze up of gas and gas gathering systems, e.g., a primary alcohol such as methanol. The alcohol will, of course, be one which will react with boron trifiuoride to form a complex. When methanol is involved, the complex is in its own right a catalyst as earlier noted.

Also according to the invention there is provided a method for the synthesis of a mercaptan from a hydrogen sulfide containing gas and an olefin, the gas containing art alcohol which poisons the catalyst, the method comprising the step of adding to the system, preferably to the hydrogen sulfide gas as it enters the system, boron trifiuoride, preferably in an amount approximately equal to its alcohol content.

In the synthesis of the invention in one embodiment thereof, a C12-C14 fraction derived from the catalytic polymerization of C3 and lC4 0lefins can be passed in admixture with the desired molar proportion of hydrogen sulfide into contact with the catalyst under conditions substantially as follows: pressures ranging from about 100 t0 1500 pounds gauge; temperatures from about atmospheric to about 3000 F. or higher. Among catalysts which can be here employed are those comprising a silica-metal oxide gel such as silica-alumina and with this catalyst a fiow rate of from about l to about 10 liquid volumes of olefin per volume of catalyst per hour usually can or will be i'mployed.

The temperature within the catalyst ibed is chosen to conform with the catalyst activity, feed composition, operating pressure and the reaction time best suited to secure optimum conversion of the olefin to mercaptan, thus temperatures are usually maintained within the range of from about 37.8℃. to about 204.4℃., a some what more preferred range of from about 93.3℃t0 148.9℃. being preferred. Higher temperatUres can be employed in special cases but in general higher temperatures tend to reduce selectivity of the reaction. In the conversion of C12 and higher olefins to the corresponding mercaptans, o a temperature range of from about 225 to about 2750F. with an active catalyst as disclosed herein is usually preferred.

Generally, catalysts which can be employed are disclosed and described in U.S. 2,426,646, issued Sept.2, 1947, Walter A. Scbulze. The disclosure of said patent is incorporated herein by reference. However, the metal there selected from Group III-B according to the Handbook of Chemistry and Physics, Chemical Rubber Company, 45th edition (1964) page B-2, would be selected from Group III-A. Similarly, the salts selected from Group III-B would be selected from Group III-A, and the salts of metals from Group IV-A would be selected from Group IV-B, Further, the metal oxide such as alumina would be not in excess of about 45 percent by weight and generally and more preferably would be between about l-25 percent by wejoht on_ a dry basis. Further, the term "Filtrol catalyst" as employed herein is inclusive of the group of acid-activated adsorption contact catalyst made from relatrvely pure crystals of montmorillonite (Mg, Ca)O-Al203-5Si02-nH20. Such catalyst may be used either with liquids or with gases in either pellet or powder form.

The olefins or olefinic material suited to the practice of the present invention generally may be defined as those materials which have been used to produce :mercaptans. Presently preferred are those olefins or materials which contain olefins having the formula

in which Ri, R2, R3 and R4 represent the same or different alkyl, hydrogen or an aryl or heterocyclic radical.The olefin will be seletced to produce a mercaptan having up to approximately 20 carbon atoms.

The invention is now particularly adapted to the production of tert-dodecyl mercaptan using for example a propylene tetramer product which can be obtained substantially as disclosed in my Pat. 2,592,089, issued Apr. 8, 1952, the disclosure of which is incorporated herein by reference. When butylenes are contained in the propylene cbarging stock, the tetramer product will contain other than 12 carbon atoms as is known.

Generally the reaction of the irrvention is exemplified by the following equation in which the R's are as earlier stated.

Triisobutylene can be reacted with H2S to produce tert-dodecyl mercaptan. U.S. Pat. 3,137,735, issued June 16, 1964, Paul F. Warner and Richard D. Franz, describes and claims a process for preparing a mercaptan from isobutylene and H2S employing a catalyst system consisting essentially of BF3-H3P04-ROH. The catalyst consists essentially of a liquid complex of an oxygen- containing acid of phosphorous, an alcohol of l t0 5 carbon atoms, and BF3. The catalyst is prepared by mixing the acid and the alcohol and adding BF3 to the mixture as further described in said patent, the disclosure of which is also incorporated herein by reference. Other patents which are of interest and related to the preparation of mercaptans by reaction of hydrogen sulfide and an olefin or olefin-containing material are 2,434,510, John F. Olin and John L. Eaton, issued Jan. 13, 1948; 2,502,596, Walter A. Schulze, issued Apr. 4, 1950; and 3,166,598, Ralph C. Cole, issued Jan. 19, 1965. The disclosures of these patents are also incorporated herein by reference.

The following examples are given by way of further illustrating this invention, it being understood that the several conc,epts thereof are not necessarily only in the l:lse of the specific materials specifically mentioned here-in nr in the examples, but rather as stated herein.

EXAMPLE I

Filtrol Grade 71 (16-200 mesh) catalyst was placed Jnto a stainless steel pipe equipped with a jacket and a thermal well. The jacket was filled with water and it was mair.tained heated to its boiling point electrically. Prior.fto this, the catalyst had been heated at 4000 F. in a stream of dry air to activate the same in place. The H2S-tetramer-methanol mixture in a weight ratio of 10.33/32.69/0.2 respectively was passed through the catalyst at 800 p.s.i.g. at about 2 volumes per volume per hour. Effiuent samples were analyzed at intervals and the operation was continued until the mercaptan content had dropped to below 60 weight percent. At this juncture, a small stainless steel bomb containing 71.9 grams of BF3 and 15.9 grams of nitrogen gas (1450 p.s.i.g.) was attached to the feed inlet to the catalyst case. At intervals a small amount of BF3-N2 mixture was added to the feed. There was obtained a dramatic increase in conversion which was maintained throughout the period of BF3 addition. Indeed, conversion which had fallen from about 89 weight percent to about 56 weight percent very sharply rose upon addition of the BF3 within a matter of 3 t0 4 volumes per volume of catalyst to approximately 94, and then thereafter averaged well above 80 percent conversion to Sulfole (a trademark for tert-dodecyl mercaptan as prepared from propylene tetramer).

Total crude product made during the BF3 addition was 4500 ml. with 61 grams BF3 added.

Filtrol等级71(16 - 200目)催化剂被放置一个不锈钢管Jnto配备一个夹克和热好。这件夹克满是水,这是mair。它获得了电加热到沸点。优先。不过,被加热的催化剂在4000f。在流干燥的空气激活相同的地方。H2S-tetramer-methanol 的混合液体倒入一个重量比10.33 /(32.69/0.2)是通过催化剂在800 p.s.i.g.上下卷单位体积大约每小时。 Effiuent 样品进行了分析和手术间隔一直持续到硫醇含量降到60重量%。在这个节骨眼上,一个小的不锈钢炸弹含71.9克的方法和15.9克的氮气(1450 p.s.i.g。)是附属于饲料进口催化剂的情况。每隔一段时间少量的BF3-N2混合添加到饲料。有了一个戏剧性的增长是在转换期间始终方法的补充。事实上,转换掉下来,大约89质量百分数56个,质量百分数严厉升起来,加入方法在大约3每单位体积的催化剂4卷大约94,然后此后平均80%以上Sulfole转换(商标tert-dodecyl硫醇丙二tetramer作好一切准备。

EXAMPLE II

Two other samples of Filtrol catalyst (Grades 25 and 62) were tried. The Grade 25 was screened t0 10-20mesh size. Results were quite similar to those shown in Example I. Conversion jumped from 63 percent t0 85-90 weight percent and was maintained at this high level for the next 24 volumes over the catalyst.其他两个样品的Filtrol催化剂(等级25和62年,试过了。25被筛选了每等级10-20mesh大小。结果很相似,即转换例所示每的63%跃升至85 - 90质量百分数和维持在高水平未来24卷的催化剂。

In Examples I and II, in the catalyst bed as there used, some plugging was experienced and for this reason the runs were discontinued. However, the beneficial effect of the introduction of BF3 according to the invention was clearly demonstrated.例如I及II型,在催化剂床在使用,但一些堵的经历,因为这个原因,拉稀有疑义。然而,有益的效果引进的方法根据发明清晰展示

EXAMPLE III

A further run was :made using Houdry Type M-46,6-48 mesh, silica-alumina catalyst (10% Al203; 90u/oS102).

Procedure and conditions were as in Examples I and IL The poisoning effect of the methanol was such that an original conversion of about 97 percent to Sulfole very sharply dropped within about 4-5 volumes to approximately 32 weight percent, but upon addition of BF3 rose within a low of approximately 2-3 volumes to an average of approximately 80 volume percent. The run was continued until about 27 volumes had been passed through the catalyst; 21 volumes 3,700 ml. of effluent was made during the period of BF3 addition. BF3 phis nitrogen added was 0.046 lb. (21 grams) of which half was estimated to be BF3. Thus, about 2500 grams of tertdodecyl mercaptan product was made with consumption of only 11 grams of BF3. After this run the catalyst bed was inspected. No sign of plugging or caking was found. This example in addition to showing elimmation of whatever plugging problem occurred in the earlier examples also shows that not withstanding the considerable effect of methanol upon the silica-alumina catalyst, the BF3 addition brought the conversion up to a very high level veryquickly. In view of the fact that no plugging occurs with the silica-alumina type catalyst, this catalyst is now believed to be suited to the best mode of operating the :invention and is pointed out to be such to satisfy the patent law and pfactice requirements.

进一步的运行是:使用M-46 Houdry类型,6-48网、矽催化剂(10%;90μ/ oS102 Al203)。程序和条件的例子我和他在甲醇中毒的影响是如此的原作转换的97%下降Sulfole严厉在大约4 - 5卷大约32质量百分数,但经添加方法的低点上涨在2 ~ 3卷到平均大约80体积百分比。这份合约延续至约27卷已经通过催化剂;21卷及废水ml.了3700年期间的方法的补充。phis氮添加方法是0.046磅。(21克)的估计方法的一半。因此,2500克tertdodecyl硫醇的消费产品是只有11克的方法。运行后的催化剂床是检查。没有迹象表明结块堵塞或被发现。这个例子显示elimmation除了堵塞问题,无论发生在早先的例子还表明,不承受的巨大影响甲醇催化剂在矽,除了转换方法带来了veryquickly到了很高的水平。

针对事实上没有堵塞发生的类型与矽催化剂,该催化剂现在被认为是适合学生学习的最佳模式的操作:发明并指出,是这样的,以满足专利法和pfactice要求。

While the invention has been described in connection with a now preferred embodiment, it will be evident to. one skilled in the art in possession of this clisclosure, having studied the same, tbat an alcohol can be removedfrom a gas by contacting the same with boron trifiuoride.虽然这项发明被认为在优选的连接在一个现在,它将会很明显。本领域普通技术人员拥有这clisclosure,在研究了一样,tbat酒精可以removedfrom气体通过联系与硼trifiuoride相同。

Alcohols which may be found in gases arb those which are substantially vaporhed or otherwise carried in the gas containing stream, such as, for example, methanol, etbanol, propanol and butanols.可以发现在醇气体arb那些大幅vaporhed 或其他包含了气体流,,例如甲醇、etbanol、丙醇及butanols。

Further, a person skilled in the art will appreciate that this invention can be applied to whatever gases or vapors may contain an alcohol. Upon formation of the BF3alcohol reaction product, this product can be treated to recover a pure alcohol therefrom and the boronduoride thus released can be reused

进一步的,一个人擅长艺术将欣赏那本发明可用于任何气体或蒸气可含有酒精。在BF3alcohol反应形成的产品,本产品可以治疗恢复一个纯酒精所得,从而释放的boronduoride可被重复利用。

Reasonable variation and modification are possible in the scope of the foregoing disclosure of the invention, the essence of which is that there have been set forth a method for sequestering alcohol from a gas or vapor, e.g., methanol, in a hydrogen sulfide gas by contacting said gas with boron trifiuoride, a method for enhancing production of mercaptan from a hydrogen sulfide gas containing an alcohol, e.g., methanol, employing a mercaptan synthesis catalyst which is pofsoned by said alcohol by treating said gas in the system with boron trifiuoride or as now preferred admixing boron trifluoride with said gas before it contacts the catalyst, substantially as described herein.

合理的变化和修改的范围可能在上述披露的发明,它的核心是有提出了一个方法从一个酒精储存气体或蒸汽,例如,甲醇,在硫化氢气体接触说气trifiuoride硼的方法,提高生产从硫化氢气体硫醇含有酒精,如甲醇、雇用硫醇合成催化剂是由说pofsoned酒精气处理系统中说trifiuoride或硼以及现在与硼trifluoride优先之前说气体接触的催化剂,实质上是描述。

I claim:我主张

1.A method for the production of a mercaptan from an olefin and a hydrogen sulfide gas containing a low boiling alcohol employing a solid mercaptan synthesis catalyst, the efficiency of which is substantially impaired by said alcohol, which comprises treating said hydrogen sulfide gas by contacting said gas with boron trifiuoride to sequester the alcohol.

方法制作硫醇烯烃和从硫化氢气体含低沸点固体酒精使用硫醇合成催化剂,效率大幅度的受说酒精,包括处理硫化氢气体通过联系说,说trifiuoride隔离气体的硼酒精。

2. A method according to claim l wherein the low boiling alcohol is methanol.

方法根据权利要求我在酒精低沸点甲醇。

3.A method according to claim l wherein the hydrogen sulfide is reacted with a compound according to the equ ationin which

Ri, R2, etc., represent the same or different alkyl, hydrogen or an aryl or radical, and in which SH is the sulfhydryl radical.

方法根据权利要求我在硫化氢是一个复合反应,根据航天ationin这国际扶轮,R2等等,代表相同或不同的烷基、氢或芳或根本,承宪的共价键激进的。

4. A method according to claim l wherein the boron trifiuoride is added to the hydrogen sulfide gas prior to contacting said gas with said olefin.方法根据权利要求我其中硼trifiuoride被添加到硫化氢气体接触前说汽油烯烃说。

5. A method according to claim 4 wherein said gas and said olefin are contacted with said solid mercaptan synthesis catalyst after the addition of the boron trifiuoride.

根据权利要求4的一种方法,其中所述气体和说接触与说烯烃合成催化剂固体硫醇后加入硼trifiuoride。

6.A method according to claim l wherein the catalyst is an Al203 and Si02 containing catalyst.

方法根据权利要求我其中催化剂是一种Si02 Al203和含催化剂。

7. A method according to claim 6 wherein the catalyst is an acid activated adsorption contact catalyst made from montmorillonite.方法根据权利要求6所述催化剂是一种酸催化剂活性吸附接触由改性。

8. A method for the production of tert-dodecyl mercaptan using an alcohol contaminated hydrogen sulfide gas in the presence of

a solid mercaptan synthesis catalyst which comprises passing propylene tetramer, feed gas and boron trifiuoride in an amount effective to sequester a substantial proportion of the contaminating alcoholinto contact with said catalyst under mercaptan synthesizing conditions of operation.

一个方法tert-dodecyl硫醇的生产使用酒精硫化氢气体的污染存在一个坚实的硫醇合成催化剂包括通过丙烯tetramer、饲料气体和硼trifiuoride金额有效隔离的相当一部分比例alcoholinto污染接触条件下硫醇催化合成说操作

References Cited参考文献

UNITED STATES PATENTS

2,481,583 9/1949 Fenn et al. ______~__ 260-609

2,498,872 2/1950 Bell et al. __________ 260-609

2,610,981' 9/1952 Short ______________ 260-609

3,005,030 10/1961 Robinson ___________ 260-609

3,006,966 t0/1961 Doumani ___________ 260-609

3,032,592 5/1962, Frantz and Glass ____ 260-609

3,035,097 5/1962 Deger et al. _________ 260-609

3,051,758 8/1962 Frantz and Warner __ 260-609

3,053,902 9/1962 Doumani ___________ 260-609

3,083,231 3/1963 Ray ____~—~__…—一_ 260-609

OTHER REFERENCES

Olah: "Friedel Crafts and Related Reactions" (1963), pp. 687-688.

CHARLES B. PARKER, Primary Examiner

D, R. PHILLIPS, Assistant Examiner

U.S. Cl. X.R.

专利常用英文

专利常用英文 专利文献翻译技巧专文献既是技术文件又是法律文件,它有一些惯用的词语,下面作一简要介绍。 一、专利惯用的词组Appl.No.(Application Number)申请号Ser.No.(Serisl Number)申请书,登记号Int.Cl.3 (International Patent Classification,3 rd Edition)国际专利分类表(第三版)Abstract of the disclosure发明摘要Preferred embodiments最佳实施方案Cross-Sheet 5 第5页(图共5页)Sheet 3 of 4第3页(图共4页) 二、常用的句子 1.Reference is made to our copending application No.25838/78 filed 31 st May 1978.请参阅我们在1978年5月31日登记的与此有关的申请书,其申请号为25838/78。说明:make reference to:参考,提及。Copending:与此有关的,尚待批准的。 2.The present application is a continuation-in-part of U.S.patent applications Ser.No.626245, filed Mar.27, 1967,now abandoned and Ser.No.767046,filed Sept.26,1968, now patent No.3619220.本专利申请书是下列两件美国专利申请书的继续。其中第一件于1967年3月27日提出申请,申请号626245,现已放弃。第二件于1968年9月26日提出申请,申请号767046,专利号3619220。说明:continuation-in-part:指的是接续专利。Ser.No.:流水号,档案号,申请号,登记号。申请专利时,专利局进行登记,编一个流水号,习惯称为申请号。经审查批准后,再编一个专利号。 3.The invention described herein may be manufactured, used, and licensed by or for the Government for governmental purposes without the payment to us of any royalty thereon.本发明若为政府公务需要而由政府或为政府制造、使用、并发给执照,均可不支付专利使用费。说明:by or for the Government: the Government 为介词by和for两者共同的宾语。royalty: 专利使用费。Thereon(=on that)关于该发明。 4.The embodiments of the invention to be described permit the production of capacitors of good electrical characteristics, without the need for using noble metal electrodes.本发明所描述的介质材料能够生产电性能良好的电容器,而无需要使用贵金属电极。 5.What is claimed is...本专利权项范围是…… 说明:What is claimed:主句从句。申请人提出专利权范围的句型还有:What I(we)claim is..., I(We)claim...等,都可译为"本

专利翻译常见词汇列表

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