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    Process for the production of secondary alcohol ether sulfates
    1.
    发明授权
    Process for the production of secondary alcohol ether sulfates 失效
    二醇醇硫酸盐生产工艺

    公开(公告)号：US3931271A

    公开(公告)日：1976-01-06

    申请号：US118549

    申请日：1971-02-24

    申请人： Horst Baumann ,  Wilfried Umbach ,  Werner Stein

    发明人： Horst Baumann ,  Wilfried Umbach ,  Werner Stein

    IPC分类号： C07C309/65 ,  C07C29/52 ,  C07C303/24 ,  C07C303/28 ,  C11D1/29 ,  C07C139/00 ,  C07C139/10 ,  C07C141/00

    CPC分类号： C07C29/52 ,  C07C303/24 ,  C11D1/29

    摘要： A process for the production of secondary alcohol ether sulfates which consists essentially of reacting adducts of secondary alkanols having from 6 to 22 carbon atoms adducted with 1 to 10 mols of an alkylene oxide selected from the group consisting of ethylene oxide and propylene oxide, said adduct having at least 1 mol of oxypropylene per mol of alcohol, with at least a molecular equivalent of a sulfating agent stronger than concentrated sulfuric acid at temperatures of from 0.degree.C to 50.degree.C and recovering said secondary alcohol ether sulfate.THE PRIOR ARTAt present secondary alcohols can be prepared from inexpensive raw materials, such as by oxidation of paraffins, substantially simpler than the preparation of primary alcohols. However, up to now the practical use of secondary alcohols is limited to non-ionic products prepared from them. Surface-active sulfates derived from secondary alcohols are used only in small amounts since the preparation of such raw materials for washing agents is very difficult, because of the instability of the secondary alkylsulfates. Primary alcohols, on the contrary, can be converted simply and with good yields into surface-active sulfates. In the sulfation of secondary alcohols, the conversion rates are low. In order to obtain somewhat usable products, expensive procedures have to be introduced, such as working with solvents and adduct formers, use of special sulfating agents, such as, for example, amidosulfonic acid, etc., as well as the addition of ethylene oxide adducts of primary alcohols. On the other hand, there is the possibility that by reaction of secondary alcohols with ethylene oxide, adducts with primary hydroxyl groups can be prepared, the sulfation products of which could be expected to have greater stability.It is, however, very difficult to prepare ethoxylates of secondary alcohols with a high conversion rate and small amounts of by-products. A higher conversion rate of the secondary alcohols with ethylene oxide can only be attained by relatively cumbersome procedures, such as, for example, a two-step ethoxylation in which in the first step an acidic catalyst is used and, after distilling off the unreacted secondary alcohol, in the second step an alkaline catalyst is utilized. However, the ethoxylated secondary alcohols obtained by this expensive procedure are also unsatisfactorily sulfated and can only be sulfated by the application of special procedures. This is difficult to explain since by the ethoxylation of secondary alcohols, adducts with primary hydroxyl groups were formed.OBJECTS OF THE INVENTIONAn object of the present invention is the development of a simple process for the production of secondary alcohol ether sulfates utilizing conventional strong sulfating agents to give products with a high degree of sulfation.Another object of the invention is the development of a process for the production of secondary alcohol ether sulfates which consists essentially of reacting adducts of secondary alkanols having from 6 to 22 carbon atoms adducted with 1 to 10 mols of an alkylene oxide selected from the group consisting of ethylene oxide and propylene oxide, said adduct having at least 1 mol of oxypropylene per mol of alcohol, with at least a molecular equivalent of a sulfating agent stronger than concentrated sulfuric acid at temperatures of from 0.degree.C to 50.degree.C and recovering said secondary alcohol ether sulfate.These and other objects of the invention will become more apparent as the description thereof proceeds.DESCRIPTION OF THE INVENTIONIt has now been surprisingly found that alkylene oxide adducts of secondary alcohols which contain at least one propylene glycol ether group can be sulfated simply with a high conversion rate. This result was the more unexpected since, as is known, on the introduction of propylene glycol ether groups by propoxylation, adducts with predominately secondary hydroxyl groups are formed. Therefore, the same difficulties in the further reaction of these adducts, especially in sulfation, would be expected as in the sulfation of secondary alcohols themselves. With this expectation, the sulfation of secondary alcohol propoxylates would appear to the expert as having little prospect of good yields.The invention relates, therefore, to a process for the preparation of surface-active ether and polyether sulfates which is characterized in that adducts of secondary alkanols having 6 to 22 carbon atoms adducted with 1 to 10 mols of alkylene oxide, possessing in the average at least 1 mol of propylene oxide per mol of alcohol, are reacted in a known manner at temperatures between 0.degree.C and 50.degree.C, particularly from 10.degree.C and 30.degree.C, with strong sulfating agents in at least stoichiometric amounts.As starting materials those adducts may be used that were obtained (1) by ethoxylation of secondary alcohols in the first step and subsequent propoxylation of the reaction mixtures, or (2) by reaction of secondary alcohols with ethylene oxide/propylene oxide mixtures, or (3) by the ethoxylation of reaction mixtures of secondary alcohols with propylene oxide, or (4) by pure propoxylation of secondary alcohols. The preferred starting materials are the adducts of propylene oxide to secondary alcohols or secondary alkanol propoxylates having 6 to 22 carbon atoms in the alkanol and 1 to 10 oxypropylene units.The mixed alkoxylates to be used contain preferably 1 to 4, particularly 2 to 3, oxyethylene groups. Of particular advantage among the pure propylene oxide adducts are those substance mixtures which were obtained by reaction of 1.5 to 5 mols of propylene oxide with 1 mol of secondary alcohol.The starting materials can be obtained by conventional alkoxylation methods. The alkoxylation can be carried out both anionically, in the presence of alkaline alkoxylation catalysts, such as alkali metal hydroxides or alkali metal alcoholates, particularly sodium, potassium and lithium lower alkanolates, and cationically in the presence of acidic catalysts, such as BF.sub.3, or in the presence of the tertiary oxonium salts described as alkoxylation catalysts in Belgian Pat. No. 715,048.If mixed adducts are used which have been obtained by propoxylation of ethylene oxide adducts of secondary alcohols as starting materials, such mixed adducts are preferred in which the alkoxylation in the first step was carried out by a cationic catalyst and in the second step with an anionic catalyst.Among the mixed adducts which are obtained by simultaneous addition of ethylene oxide and propylene oxide, or by propoxylation in the first step and ethoxylation in the second step, as well as in the pure propoxylation products, these are preferably prepared by reaction with an anionic catalyst.The secondary alcohols utilized to prepare the alkoxylation mixtures can be either compounds of uniform chain length or mixtures of homologs. Of particular economic advantage are those alcohol mixtures which have been obtained by the oxidation of paraffins in the presence of boron compounds, such as, for example, boric acid, boron trioxide, borates, boric acid esters, as well as other known reagents for the formation of secondary alcohols, such as arsenic acid, arsenic acid esters, arsenic trioxide, and others.The alkoxylation mixtures utilizable for the subsequent sulfation can be used as crude products, that is, without intervening purification or processing operations. This is of essential importance for the technical execution of the process. These crude alkoxylation mixtures contain, therefore, in addition to the desired alkylene oxide adducts of secondary alcohols, as secondary constituents, the corresponding alkylene and/or polyalkylene glycols as well as, possibly, non-reacted secondary alcohol. The sulfation of the alkoxylate mixture is preferably carried out in the temperature range of from 10.degree.C to 30.degree.C.By "strong sulfating agents" are meant those which are stronger than concentrated sulfuric acid, for example, SO.sub.3 or SO.sub.3 /air mixtures, oleum, chlorosulfonic acid, and the like. The addition of adduct formers for the sulfating agent or the presence of solvents are not required in the process. The preferred sulfating agent is chlorosulfonic acid. The mol ratio between the alkoxylate and the sulfating agent is advantageously chosen in the range of from 1:1.0 to 1:1.2, particularly in the range of from 1:1.02 to 1:1.1.The sulfation reaction can be carried out continuously or discontinuously. The reaction times lie between fractions of seconds to about 20 minutes, depending upon the sulfating agent and/or sulfating apparatus used. Particularly short reaction times are attained if the reaction is carried out with very strong sulfating agents, such as SO.sub.3 /air mixtures, in modern short-time sulfation reactors which operate by the split-ring or falling film principle.The products of the process have a substantially higher degree of sulfation than the products obtained by the sulfation of technical ethylene oxide adducts of secondary alcohols. They have, without further processing, very good surface-active properties and are superior, particularly in regard to their wetting action, to the known commercial sulfated adducts of ethylene oxide to primary alcohols.The advantages attainable with the invention consist primarily in that as a raw material source for surface-active, water-soluble sulfates, secondary alcohols have been made available. Particularly those secondary alcohols which are easily obtainable by paraffin oxidation in the presence of the above-named oxidation catalysts to produce secondary alcohols with statistically distributed hydroxyl groups. These alcohols are converted by alkoxylation to the substances suitable for sulfation. Thus, these petrochemical raw materials can form the basis for the desired surface-active substances. Anionic active derivatives of secondary alcohols were up to now technically not producible by a simple way although secondary alcohols have been produced for some time on a large scale. The use of secondary alcohols was, therefore, until now limited to the production of non-ionic substances.A further advantage of the process according to the invention can be seen in that the necessary alkoxylation may be carried out without a large expense in regard to catalysts and/or equipment.The following examples are illustrative of the invention without being deemed limitative in any respect.

    摘要翻译： 一种生产仲醇醚硫酸盐的方法，其主要包括与6至22个碳原子的仲烷醇的加合物加成1至10摩尔选自环氧乙烷和环氧丙烷的环氧烷烃，所述加合物 每摩尔醇具有至少1摩尔氧化丙烯，至少在0℃至50℃的温度下至少分子当量的硫酸化剂比浓硫酸更强，并回收所述仲醇醚硫酸盐。

    Preparation of light-colored, wash active .alpha.-sulfofatty acid
    2.
    发明授权
    Preparation of light-colored, wash active .alpha.-sulfofatty acid 失效
    制备浅色，洗涤活性α-磺基脂肪酸

    公开(公告)号：US4671900A

    公开(公告)日：1987-06-09

    申请号：US288769

    申请日：1981-07-31

    申请人： Karl Schmid ,  Werner Stein ,  Horst Baumann

    发明人： Karl Schmid ,  Werner Stein ,  Horst Baumann

    IPC分类号： C07C67/00 ,  C07C301/00 ,  C07C303/06 ,  C07C303/42 ,  C07C303/44 ,  C07C309/09 ,  C07C309/17 ,  C07C309/58 ,  C07C309/62 ,  C11C3/00 ,  C11D1/28 ,  C07C143/90

    CPC分类号： C07C303/42 ,  C11C3/00 ,  C11D1/28

    摘要： This invention is directed to the preparation of .alpha.-sulfofatty acid esters. More particularly, this invention is directed to a process for the simplified preparation of light-colored, wash-active esters of .alpha.-sulfofatty acids with monovalent C.sub.1 to C.sub.8 alcohols or their salts from fats and oils of vegetable and/or animal origin comprising re-esterification with the monovalent alcohols or saponification and esterification with the monovalent alcohols, separation of the fatty acid ester formed, hydrogenation of the fatty acid ester, sulfonation, and bleaching, wherein a fatty acid ester fraction from which accompanying fatty acid glycerides have been removed to the extent of about 1 percent by weight or less, based upon the weight of the material to be sulfonated, is introduced into the sulfonation stage.

    摘要翻译： 本发明涉及α-磺基脂肪酸酯的制备。 更具体地，本发明涉及一种简单制备α-磺基脂肪酸的浅色洗涤活性酯与一价C1至C8醇或其植物和/或动物来源的脂肪和油的盐的方法，其包括re 用单价醇进行酯化反应或用单价醇皂化和酯化，形成脂肪酸酯的分离，脂肪酸酯的氢化，磺化和漂白，其中伴随的脂肪酸甘油酯已被除去的脂肪酸酯部分 基于待磺化材料的重量约1重量％或更少的程度引入磺化阶段。

    Sulfonated lubricating agents for leather and furs and process
    3.
    发明授权
    Sulfonated lubricating agents for leather and furs and process 失效
    用于皮革和毛皮的磺化润滑剂和工艺

    公开(公告)号：US3988247A

    公开(公告)日：1976-10-26

    申请号：US391201

    申请日：1973-08-24

    申请人： Gerhard Dieckelmann ,  Jurgen Plapper ,  Horst Baumann ,  Werner Stein

    发明人： Gerhard Dieckelmann ,  Jurgen Plapper ,  Horst Baumann ,  Werner Stein

    IPC分类号： C14C9/00 ,  C14C9/02

    CPC分类号： C14C9/02 ,  C07C309/00

    摘要： Process and agent for fatting or lubrication of leather and furs based on the salts of sulfonated chlorinated products of higher fatty acids or of esters of higher fatty acids, said fatty acids having from 8 to 24 carbon atoms, especially natural fats and oils or tallow fatty acid methyl ester, having a chlorine content of 20% to 45% by weight and essentially free of olefinic double bonds and having an SO.sub.3 content of from 40 to 150 mol percent based on the chlorinated product, which agent and the leather and furs so treated are extraordinarily resistant to the effect of light, to oxidation and to acids.

    摘要翻译： 基于高级脂肪酸的磺化氯化产物或高级脂肪酸的酯的脂肪酸，具有8至24个碳原子的脂肪酸，特别是天然脂肪和油或牛油脂肪的皮革和毛皮的脂肪化或润滑的方法和试剂 酸性甲酯，其氯含量为20重量％至45重量％，基本上不含烯属双键，并且基于氯化产物，SO 3含量为40至150摩尔％，该试剂和皮革和毛皮如此处理 对光，氧化和酸的作用非常有抵抗力。

    Continuous process for bleaching acid alpha-sulfo-fatty acid esters
    4.
    发明授权
    Continuous process for bleaching acid alpha-sulfo-fatty acid esters 失效
    用于漂白酸性α-磺基脂肪酸酯的连续方法

    公开(公告)号：US4080372A

    公开(公告)日：1978-03-21

    申请号：US748096

    申请日：1976-12-06

    申请人： Werner Stein ,  Horst Baumann ,  Hans Josef Rommerskirchen

    发明人： Werner Stein ,  Horst Baumann ,  Hans Josef Rommerskirchen

    IPC分类号： C07C309/30 ,  C07C20060101 ,  C07C67/00 ,  C07C301/00 ,  C07C303/42 ,  C07C303/44 ,  C07C309/17 ,  C07C309/58 ,  C11D1/28 ,  C07C143/90

    CPC分类号： C07C303/42

    摘要： A continuous process for the bleaching of acid .alpha.-sulfo-fatty acid esters of predominantly C.sub.16-24 fatty acids comprising continuously adding the hydrogen peroxide bleach in aqueous solution as well as from 2% to 50% by weight, based on the sulfonated esters, of a C.sub.6-18 alkylbenzene sulfonic acid, to said raw, acid .alpha.-sulfo-fatty acid esters at a temperature of 40.degree. to 65.degree. C, continuously passing said mixture through a confined zone of dimensions sufficient to give a proper bleach retention time and continuously recovering bleached .alpha.-sulfo-fatty acid esters.

    摘要翻译： 用于漂白主要为C 16-24脂肪酸的酸性α-磺基脂肪酸酯的连续方法包括基于磺化酯连续地加入过氧化氢漂白剂在水溶液中，以及2重量％至50重量％ 的C 6-18烷基苯磺酸，在40℃至65℃的温度下，将所述生的酸式α-磺基脂肪酸酯连续地通过所述混合物通过足够的适当的漂白保留时间的限定区域 并连续回收漂白的α-磺基脂肪酸酯。

    Quaternary ammonium compounds, their production and use in fabric aftertreatment preparations
    7.
    发明授权
    Quaternary ammonium compounds, their production and use in fabric aftertreatment preparations 失效
    季铵化合物，其生产和用于织物后处理制剂

    公开(公告)号：US4923642A

    公开(公告)日：1990-05-08

    申请号：US121267

    申请日：1987-11-16

    申请人： Horst Rutzen ,  Horst Baumann ,  Bert Gruber

    发明人： Horst Rutzen ,  Horst Baumann ,  Bert Gruber

    IPC分类号： D06M13/46 ,  C07C219/06 ,  C11D1/62 ,  D06M13/02 ,  D06M13/322 ,  D06M13/463

    CPC分类号： C11D1/62 ,  D06M13/463 ,  D06M2200/50

    摘要： Quaternary ammonium compounds containing one or two long-chain ester or amide radicals of etherified hydroxycarboxylic acids and, for the remainder, short-chain radicals, which are liquid to pasty substances that may readily be dissolved or dispersed in water or alcohol/water mixtures. They may be used in dilute or concentrated, storable form for softening fabrics without the absorbency of the treated fabrics being adversely affected. The quaternary ammonium compounds are obtained by reaction of epoxyfatty acid esters with amines and subsequent quaternization.

    摘要翻译： 含有一个或两个醚化羟基羧酸的长链酯或酰胺基团的季铵化合物，以及其余的短链基团，其是易于溶解或分散在水或醇/水混合物中的液态至糊状物质。 它们可以以稀释或浓缩，可储存的形式用于软化织物，而不会对被处理织物的吸收性受到不利影响。 季铵化合物通过环氧脂肪酸酯与胺的反应和随后的季铵化反应获得。

    Aqueous anionic surfactant concentrates containing viscosity reducing agents
    8.
    发明授权
    Aqueous anionic surfactant concentrates containing viscosity reducing agents 失效
    含有降粘剂的水性阴离子表面活性剂浓缩物

    公开(公告)号：US4532076A

    公开(公告)日：1985-07-30

    申请号：US543672

    申请日：1983-10-19

    申请人： Karl Schmid ,  Horst Baumann ,  Hans J. Rommerskirchen

    发明人： Karl Schmid ,  Horst Baumann ,  Hans J. Rommerskirchen

    IPC分类号： C09K3/00 ,  C11D1/12 ,  C11D1/28 ,  C11D3/20 ,  C11D3/24 ,  C11D3/26 ,  C11D3/33 ,  C11D3/34 ,  G05D24/00

    CPC分类号： C11D3/2093 ,  C11D1/12 ,  C11D1/28 ,  C11D3/2068 ,  C11D3/2075 ,  C11D3/2082 ,  C11D3/33 ,  Y10S516/03 ,  Y10S516/04

    摘要： An aqueous anionic surfactant concentrate containing certain low molecular weight organic compounds as viscosity regulators and a method of regulating the viscosity of highly viscous concentrates, e.g. .alpha.-sulfo fatty acid ester surfactants in concentrations about 30% by weight. The viscosity regulators are selected from:(a) a C.sub.1 -C.sub.6 -alkyl monocarboxylic acid substituted in the .alpha.-position by a halogen, cyano or sulfo group, a salt thereof, or an ester thereof with a C.sub.1 -C.sub.6 -alkanol,(b) a C.sub.1 -C.sub.6 -alkylene dicarboxylic acid substituted in the .alpha.-position by a halogen, cyano or sulfo group, a salt thereof, or an ester thereof with a C.sub.1 -C.sub.6 -alkanol,(c) nitrilotriacetic acid and its salts,(d) an ether alcohol containing from 2 to 4 alkylene glycol units and 1 alkoxy group,(e) and mixtures thereof.

    摘要翻译： 含有某些低分子量有机化合物作为粘度调节剂的水性阴离子表面活性剂浓缩剂和调节高粘度浓缩物的粘度的方法， 浓度为约30重量％的α-磺基脂肪酸酯表面活性剂。 粘度调节剂选自：（a）在α-位上被卤素，氰基或磺基取代的C 1 -C 6烷基单羧酸，其盐或其与C 1 -C 6烷醇的酯（ b）在α-位上被卤素，氰基或磺基取代的C1-C6-亚烷基二羧酸，其盐或其与C1-C6-链烷醇的酯，（c）次氮基三乙酸及其盐， （d）含有2至4个亚烷基二醇单元和1个烷氧基的醚醇，（e）及其混合物。

    Dishwashing compositions containing higher 1,2-alkanediol ether monosulfates
    9.
    发明授权
    Dishwashing compositions containing higher 1,2-alkanediol ether monosulfates 失效
    含有较高1,2-链烷二醇醚单硫酸盐的洗碗组合物

    公开(公告)号：US3936317A

    公开(公告)日：1976-02-03

    申请号：US551710

    申请日：1975-02-21

    申请人： Hans-Jurgen Lehmann ,  Martin Bischoff ,  Horst Baumann ,  Peter Krings

    发明人： Hans-Jurgen Lehmann ,  Martin Bischoff ,  Horst Baumann ,  Peter Krings

    IPC分类号： C11D1/12 ,  C11D1/14 ,  C11D1/22 ,  C11D1/28 ,  C11D1/29 ,  C11D1/37 ,  C11D17/00 ,  C11D1/16 ,  C11D17/08

    CPC分类号： C11D1/12 ,  C11D1/37 ,  C11D1/123 ,  C11D1/143 ,  C11D1/22 ,  C11D1/28 ,  C11D1/29

    摘要： A dishwashing and cleansing agent composition for manual dishwashing based upon anionic surface-active surfactants consists essentially of (A) from 20% to 90% by weight of a higher sulfonate or sulfate of the group of the alkyl sulfonates, olefin sulfonates, .alpha.-sulfofatty acid alkyl esters, dialkyl sulfosuccinic esters, alkylbenzene sulfonates and alkyl sulfates, each having 8 to 20 carbon atoms in the hydrophobic moiety, and (B) from 10% to 80% by weight of a mono- or polyglycol ether sulfate of a higher 1,2-alkanediol having 10 to 22 carbon atoms; as well as a dishwashing concentrate containing this composition and a method of using this composition.

    摘要翻译： 用于基于阴离子表面活性表面活性剂的手动餐具洗涤的洗碗和清洁剂组合物基本上由（A）20重量％至90重量％的烷基磺酸盐，烯烃磺酸盐，α-磺基磺酸盐的较高磺酸盐或硫酸盐 酸性烷基酯，二烷基磺基琥珀酸酯，烷基苯磺酸盐和烷基硫酸盐，每个在疏水部分中具有8至20个碳原子，和（B）10％至80％重量的1或1％的单 - 或聚乙二醇醚硫酸盐 具有10-22个碳原子的2-链烷二醇; 以及含有该组合物的洗碟浓缩物和使用该组合物的方法。