KR100423965B1 - Production Method of Sodium 4-dodecanoyloxybenzenesulfonate - Google Patents

Production Method of Sodium 4-dodecanoyloxybenzenesulfonate Download PDF

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KR100423965B1
KR100423965B1 KR10-2001-0049724A KR20010049724A KR100423965B1 KR 100423965 B1 KR100423965 B1 KR 100423965B1 KR 20010049724 A KR20010049724 A KR 20010049724A KR 100423965 B1 KR100423965 B1 KR 100423965B1
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sodium
dodecanoyl
sulfonate
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chloride
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KR10-2001-0049724A
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KR20030015905A (en
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오상헌
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미원상사주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/58—Carboxylic acid groups or esters thereof

Abstract

본 발명은 본 발명은 산소계 표백제에 첨가되어 과산화수소와 반응하여 표백력을 증대시키는 소디움 4-도데카노일 옥시벤젠 설포네이트(DOBS)의 제조방법에 관한 것으로, 반응 완료후 생성물을 수득함에 있어서, 여과성을 개선하는 것이 목적이다.The present invention relates to a method for preparing sodium 4-dodecanoyl oxybenzene sulfonate (DOBS) which is added to an oxygen-based bleach to react with hydrogen peroxide to increase bleaching power. The purpose is to improve.

소디움 4-페놀 설포네이트(SPS)와 도데카노일 클로라이드를 반응시켜 소디움 4-도데카노일 옥시벤젠 설포네이트를 제조함에 있어서, 촉매로 트리에틸 아민을 사용하고, 헵탄 또는 톨루엔을 용매로 사용하며, 반응후 용매를 메탄올로 치환한 후 여과하는 것을 특징으로 한다. 본 발명에 의하면 분말상의 소디움 4-도데카노일 옥시벤젠 클로라이드를 얻을 수 있으며 이로써 후속공정이 유리해진다.In preparing sodium 4-dodecanoyl oxybenzene sulfonate by reacting sodium 4-phenol sulfonate (SPS) with dodecanoyl chloride, triethyl amine is used as a catalyst, heptane or toluene is used as a solvent, After the reaction is characterized in that the solvent is replaced by methanol and then filtered. According to the present invention a powdery sodium 4-dodecanoyl oxybenzene chloride can be obtained, which favors the subsequent process.

Description

소디움 4-도데카노일 옥시벤젠 설포네이트의 제조방법{Production Method of Sodium 4-dodecanoyloxybenzenesulfonate}Preparation Method of Sodium 4-dodecanoyloxybenzenesulfonate

세탁할 때 커피나 주스 등의 얼룩은 통상의 세제만으로는 완전히 제거되지 않으므로 일반적으로 표백제를 사용하여 제거하는데 표백제는 통상 기초 원료에 따라 염소계와 산소계로 분류된다.When washing, stains such as coffee or juice are not completely removed only by ordinary detergents, and are generally removed using bleach. Bleaches are generally classified into chlorine and oxygen based on basic raw materials.

가정용으로는 산소계 표백제중 과산화수소를 사용하는 과산 표백제가 주로 사용되는데 과산 표백제는 취급하기 편리하다는 장점이 있으나 비교적 고온에서 세탁해야 하는 것이 단점이다. 왜냐하면, 과산 표백제는 60℃ 이상에서 효과적인데 그 온도에서는 과산화수소가 분해되므로 결국 원하는 수준의 표백 효과를 위해서는 과량을 사용해야 하기 때문이다. 또한, 일반적으로 가정에서는 60℃ 이하의 물로 세탁하므로 과산 표백제만으로 표백하는 것은 근본적으로 한계가 있다. 따라서, 과산 표백제의 성능을 향상시키기 위하여 표백 활성제를 첨가한다.Peroxide bleach, which uses hydrogen peroxide among oxygen-based bleach, is mainly used, but peracid bleach has the advantage of being convenient to handle, but it is disadvantageous to be washed at a relatively high temperature. This is because the peracid bleach is effective at 60 ° C. or higher because hydrogen peroxide is decomposed at that temperature, so an excess amount must be used for the desired level of bleaching effect. In addition, in general, at home, washing with water of 60 ℃ or less, there is a fundamental limit to bleaching only with a peracid bleach. Therefore, a bleach activator is added to improve the performance of the peracid bleach.

그리하여, 현재까지 다양한 표백 활성제가 개발되었는데 본 발명은 표백 활성제 중 산소계 표백제에 첨가되어 과산화수소와 반응하여 표백력을 증대시키는 소디움 4-도데카노일 옥시벤젠 설포네이트(DOBS)의 제조방법, 상세하게는, 소디움 4-페놀 설포네이트(SPS)와 도데카노일 클로라이드(라우로일 클로라이드)를 반응시켜 소디움 4-도데카노일 옥시벤젠 설포네이트(DOBS)를 제조하는 방법에 관한 것이다.Thus, various bleaching activators have been developed so far. The present invention relates to a method for preparing sodium 4-dodecanoyl oxybenzene sulfonate (DOBS) which is added to an oxygen-based bleaching agent among the bleaching activators to increase bleaching power. And a method for producing sodium 4-dodecanoyl oxybenzene sulfonate (DOBS) by reacting sodium 4-phenol sulfonate (SPS) with dodecanoyl chloride (lauroyl chloride).

소디움 4-도데카노일 옥시벤젠 설포네이트(DOBS)의 제조방법으로, 일본공개특허 평8-53405에는 소디움 4-페놀 설포네이트와 도데카노일 클로라이드에 도데카노익산을 첨가하여 제조하는 방법이 개시되어 있다. 그러나, 반응 후 잔존하는 지방산의 일종인 도데카노익산으로 인해 결정화된 제품을 얻기 위한 여과공정이 어렵다는 단점이 있다.As a method for preparing sodium 4-dodecanoyl oxybenzene sulfonate (DOBS), Japanese Patent Laid-Open No. Hei 8-53405 discloses a method for producing sodium 4-phenol sulfonate and dodecanoyl chloride by adding dodecanoic acid. have. However, there is a disadvantage that the filtration process for obtaining a crystallized product is difficult due to dodecanoic acid, a kind of fatty acid remaining after the reaction.

일본공개특허 평8-217721호와 평8-217722호에는 자일렌을 용매로 사용하여 소디움 4-페놀 설포네이트와 도데카노일 클로라이드를 반응시킨 후 여과하여 헥산으로 수세하는 방법이 개시되어 있고, 일본공개특허 평8-176092에는 폴리에틸렌 글리콜을 용매로 사용하여 소디움 4-페놀 설포네이트와 도데카노일 클로라이드를 반응시켜 제조하는 방법이 개시되어 있으나 모두 여과성이 좋지 않다는 단점이 있다.Japanese Patent Application Laid-Open Nos. 8-217721 and 8-217722 disclose a method of reacting sodium 4-phenol sulfonate and dodecanoyl chloride using xylene as a solvent, followed by filtration and washing with hexane. Patent Publication No. Hei 8-176092 discloses a method of reacting sodium 4-phenol sulfonate with dodecanoyl chloride using polyethylene glycol as a solvent, but all have disadvantages of poor filterability.

본 발명의 목적은 소디움 4-페놀 설포네이트(SPS)와 도데카노일 클로라이드를 반응시켜 소디움 4-도데카노일 옥시벤젠 설포네이트를 제조할 때, 반응 완료후 생성물을 수득함에 있어서, 여과성을 개선하는 것이다.An object of the present invention is to improve the filterability in obtaining a product after completion of the reaction when preparing sodium 4-dodecanoyl oxybenzene sulfonate by reacting sodium 4-phenol sulfonate (SPS) with dodecanoyl chloride. will be.

상기 목적을 달성하기 위한 본 발명은 소디움 4-페놀 설포네이트(SPS)와 도데카노일 클로라이드를 반응시켜 소디움 4-도데카노일 옥시벤젠 설포네이트를 제조함에 있어서(하기 반응식 1), 촉매로 트리에틸 아민을 사용하고, 용매로 헵탄을 사용하며, 반응 후 용매를 메탄올로 치환한 후 여과하는 것을 특징으로 한다.In order to achieve the above object, the present invention is to prepare sodium 4-dodecanoyl oxybenzene sulfonate by reacting sodium 4-phenol sulfonate (SPS) with dodecanoyl chloride (Scheme 1). An amine is used, heptane is used as a solvent, and after the reaction, the solvent is replaced with methanol, followed by filtration.

상기 본 발명의 제조방법을 일본공개특허 평8-217721호와 비교하면, 반응시 용매로 헵탄을 사용하고 촉매로 트리에틸 아민을 사용한다는 점, 그리고 반응이 완료된 후 용매를 메탄올로 치환한 후 여과한다는 점이 특징적인 차이점이다.Comparing the preparation method of the present invention with JP-A-8-217721, heptane is used as a solvent in the reaction and triethyl amine is used as a catalyst in the reaction, and after completion of the reaction, the solvent is replaced with methanol and filtered. This is a characteristic difference.

반응물인 소디움 4-페놀 설포네이트(SPS)와 도데카노일클로라이드는 SPS:도데카노일 클로라이드의 당량비가 1:1.0 ~ 1:1.3이 되도록 하여 반응시킨다.The reactant sodium 4-phenol sulfonate (SPS) and dodecanoyl chloride are reacted so that the equivalent ratio of SPS: dodecanoyl chloride is 1: 1.0 to 1: 1.3.

촉매인 트리에틸 아민은 소디움 4-페놀 설포네이트:트리에틸 아민의 ??량비가 1:0.3 ~ 1:0.6이 되도록 사용한다.Triethyl amine is used as a catalyst such that the ratio of sodium 4-phenol sulfonate: triethyl amine is 1: 0.3 to 1: 0.6.

용매인 헵탄은 소디움 4-페놀 설포네이트(SPS) 질량의 2.5 ~ 3.5배 사용하는데, 톨루엔을 사용할 수도 있다. 생성물의 성상이 슬러리이므로 용매를 적게 사용하면 교반하기가 어려워진다.Heptane, a solvent, uses 2.5 to 3.5 times the mass of sodium 4-phenol sulfonate (SPS), but toluene may be used. Since the product properties are slurries, using less solvent makes it difficult to stir.

반응온도는 용매로 헵탄을 사용하는 경우에는 90~98℃에서 진행시키며 바람직하게는, 헵탄의 비점인 98℃에서 환류시키면서 반응시킨다. 톨루엔을 용매로 사용하는 경우에는 90~130℃에서 반응시킨다.When heptane is used as the solvent, the reaction temperature is carried out at 90 to 98 ° C. Preferably, the reaction temperature is reacted while refluxing at 98 ° C, which is the boiling point of heptane. When toluene is used as a solvent, the reaction is carried out at 90 to 130 ° C.

반응이 완료된 후에는 감압시켜 헵탄을 제거하고 메탄올을 가한다. 메탄올은 소디움 4-페놀 설포네이트(SPS) 질량의 2.0 ~ 4.0배를 사용한다.After the reaction was completed, heptane was removed under reduced pressure, and methanol was added thereto. Methanol uses 2.0 to 4.0 times the mass of sodium 4-phenol sulfonate (SPS).

상기 본 발명의 구성은 다음 실시예로부터 더욱 명확해질 것이다.The configuration of the present invention will be clearer from the following examples.

<실시예 1><Example 1>

소디움 4-페놀 설포네이트 98.08g(0.5mol)와 트리에틸 아민 25.30g(0.25mol)을 헵탄 300g에 투입하고, 질소 분위기하에서 교반하면서 도데카노일 클로라이드 109.39g(0.5mol)를 30분간에 걸쳐 적하한 후, 98℃로 승온하고 3시간 동안 환류시키면서 반응시켰다.98.08 g (0.5 mol) of sodium 4-phenol sulfonate and 25.30 g (0.25 mol) of triethyl amine were added to 300 g of heptane, and 109.39 g (0.5 mol) of dodecanoyl chloride was added dropwise over 30 minutes while stirring under a nitrogen atmosphere. After that, the mixture was heated to 98 ° C. and reacted under reflux for 3 hours.

반응물을 50℃까지 냉각시키고, 감압시켜 헵탄을 제거하였다. 이어서, 메탄올 300g을 투입하고, 25% NaOH 수용액으로 pH를 8.0으로 맞춘 후, 이를 여과하여 60℃ 오븐에서 12시간 건조시킨 결과, 순도 90%의 소디움 4-도데카노일 옥시벤젠 클로라이드 분말 151.37g이 얻어졌다.The reaction was cooled to 50 ° C. and reduced pressure to remove heptane. Subsequently, 300 g of methanol was added, the pH was adjusted to 8.0 with a 25% NaOH aqueous solution, which was filtered and dried in an oven at 60 ° C. for 12 hours. As a result, 151.37 g of sodium 4-dodecanoyl oxybenzene chloride powder having a purity of 90% was obtained. Obtained.

<실시예 2><Example 2>

소디움 4-페놀 설포네이트 98.08g(0.5mol)와 트리에틸 아민 25.30g(0.25mol)을 헵탄 300g에 투입하고, 질소 분위기하에서 교반하면서 도데카노일 클로라이드 142.20g(0.65mol)를 30분간에 걸쳐 적하한 후, 98℃로 승온하고 3시간 동안 환류시키면서 반응시켰다.98.08 g (0.5 mol) of sodium 4-phenol sulfonate and 25.30 g (0.25 mol) of triethylamine were added to 300 g of heptane, and 142.20 g (0.65 mol) of dodecanoyl chloride was added dropwise over 30 minutes while stirring under a nitrogen atmosphere. After that, the mixture was heated to 98 ° C. and reacted under reflux for 3 hours.

반응물을 50℃까지 냉각시키고, 감압시켜 헵탄을 제거하였다. 이어서, 메탄올 300g을 투입하고, 25% NaOH 수용액으로 pH를 8.0으로 맞춘 후, 이를 여과하여 60℃ 오븐에서 12시간 건조시킨 결과, 90% 순도의 소디움 4-도데카노일 옥시벤젠 클로라이드 분말 170.29g이 얻어졌다.The reaction was cooled to 50 ° C. and reduced pressure to remove heptane. Subsequently, 300 g of methanol was added, the pH was adjusted to 8.0 with a 25% NaOH aqueous solution, and the resultant was filtered and dried in an oven at 60 ° C. for 12 hours. As a result, 170.29 g of sodium 4-dodecanoyl oxybenzene chloride powder having 90% purity was Obtained.

<비교예 1>Comparative Example 1

일본공개특허 평8-217722호에 기재된 방법에 따라 제조하였다.It manufactured according to the method of Unexamined-Japanese-Patent No. 8-217722.

소디움 4-페놀 설포네이트 196g(1mol), 도데카노일 클로라이드 263g(1.2mol)을 자일렌 400g에 투입하고, 질소 분위기하에서 120℃로 승온한 후 2시간 동안 반응시켰다. 생성물을 감압여과하고자 하였으나 여과되지 않았고, 10시간 동안 방치한 후 헥산으로 세척하고 다시 시도하였으나 마찬가지로 여과되지 않았다.196 g (1 mol) of sodium 4-phenol sulfonate and 263 g (1.2 mol) of dodecanoyl chloride were added to 400 g of xylene, and the reaction mixture was heated to 120 ° C. under nitrogen atmosphere for 2 hours. The product was to be filtered under reduced pressure but was not filtered, left for 10 hours, washed with hexane and tried again but not filtered as well.

문헌상으로는 최대 96%의 수율로 소디움 4-도데카노일 옥시벤젠 클로라이드를 얻을 수 있었다고 기재되어 있으나 여과되지 않아 수율을 측정할 수 없었다.The literature states that sodium 4-dodecanoyl oxybenzene chloride could be obtained with a yield of up to 96%, but the yield could not be determined because it was not filtered.

본 발명에 의하면 소디움 4-도데카노일 옥시벤젠 클로라이드의 여과성이 향상되어 분말상의 소디움 4-도데카노일 옥시벤젠 클로라이드를 얻을 수 있으며 후속공정이 유리해진다.According to the present invention, the filterability of sodium 4-dodecanoyl oxybenzene chloride is improved to obtain powdery sodium 4-dodecanoyl oxybenzene chloride, and the subsequent process is advantageous.

Claims (7)

소디움 4-페놀 설포네이트(SPS)와 도데카노일 클로라이드를 반응시켜 소디움 4-도데카노일 옥시벤젠 설포네이트를 제조함에 있어서, 촉매로 트리에틸 아민을 사용하고, 헵탄을 용매로 사용하며, 반응후 용매를 메탄올로 치환한 후 여과하는 것을 특징으로 하는 소디움 4-도데카노일 옥시벤젠 설포네이트의 제조방법.In preparing sodium 4-dodecanoyl oxybenzene sulfonate by reacting sodium 4-phenol sulfonate (SPS) with dodecanoyl chloride, triethyl amine is used as a catalyst and heptane is used as a solvent. A method for producing sodium 4-dodecanoyl oxybenzene sulfonate, wherein the solvent is replaced with methanol and then filtered. 제1항에 있어서, 용매로 톨루엔을 사용하는 것을 특징으로 하는 소디움 4-도데카노일 옥시벤젠 설포네이트의 제조방법.The method for producing sodium 4-dodecanoyl oxybenzene sulfonate according to claim 1, wherein toluene is used as a solvent. 제1항에 있어서, 반응물인 소디움 4-페놀 설포네이트(SPS)와 도데카노일클로라이드를 SPS:도데카노일 클로라이드의 당량비가 1:1.0 ~ 1:1.3이 되도록 반응시키는 것을 특징으로 하는 소디움 4-도데카노일 옥시벤젠 설포네이트의 제조방법.The sodium 4-phenol sulfonate (SPS) and dodecanoyl chloride as reactants according to claim 1, wherein the equivalent ratio of SPS: dodecanoyl chloride is 1: 1.0 to 1: 1.3. Process for preparing dodecanoyl oxybenzene sulfonate. 제1항에 있어서, 촉매인 트리에틸 아민을 소디움 4-페놀 설포네이트(SPS):트리에틸 아민의 ??량비가 1:0.3 ~ 1:0.6이 되도록 사용하는 것을 특징으로 하는 소디움 4-도데카노일 옥시벤젠 설포네이트의 제조방법.2. Sodium 4-dodecano, according to claim 1, wherein triethyl amine, which is a catalyst, is used in such a manner that the ratio of sodium 4-phenol sulfonate (SPS): triethyl amine is 1: 0.3 to 1: 0.6. Process for the preparation of one oxybenzene sulfonate. 제1항에 있어서, 용매인 헵탄을 소디움 페놀 설포네이트(SPS) 질량의 2.5 ~ 3.5배를 사용하는 것을 특징으로 하는 소디움 4-도데카노일 옥시벤젠 설포네이트의제조방법.The method for producing sodium 4-dodecanoyl oxybenzene sulfonate according to claim 1, wherein heptane as a solvent is used at 2.5 to 3.5 times the mass of sodium phenol sulfonate (SPS). 제1항에 있어서, 반응온도가 90~98℃인 것을 특징으로 하는 소디움 4-도데카노일 옥시벤젠 설포네이트의 제조방법.The method for producing sodium 4-dodecanoyl oxybenzene sulfonate according to claim 1, wherein the reaction temperature is 90 to 98 ° C. 제2항에 있어서, 반응온도가 90~130℃인 것을 특징으로 하는 소디움 4-도데카노일 옥시벤젠 설포네이트의 제조방법.The method for producing sodium 4-dodecanoyl oxybenzene sulfonate according to claim 2, wherein the reaction temperature is 90 to 130 ° C.
KR10-2001-0049724A 2001-08-18 2001-08-18 Production Method of Sodium 4-dodecanoyloxybenzenesulfonate KR100423965B1 (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0148148A2 (en) * 1983-12-27 1985-07-10 Monsanto Company Production of sodium alkanoyloxybenzene sulfonate
EP0164786A2 (en) * 1984-06-08 1985-12-18 Shell Internationale Researchmaatschappij B.V. A process for the preparation of p-isononanoyloxybenzenenesulphonate
EP0220826A1 (en) * 1985-09-28 1987-05-06 Interox Chemicals Limited Preparation of sulphophenyl esters
US4666636A (en) * 1985-10-28 1987-05-19 Monsanto Company Production of sodium phenol sulfonate
US5069828A (en) * 1989-06-06 1991-12-03 E. I. Du Pont De Nemours And Company Process for preparing benzenesulfonate salts

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0148148A2 (en) * 1983-12-27 1985-07-10 Monsanto Company Production of sodium alkanoyloxybenzene sulfonate
EP0164786A2 (en) * 1984-06-08 1985-12-18 Shell Internationale Researchmaatschappij B.V. A process for the preparation of p-isononanoyloxybenzenenesulphonate
EP0220826A1 (en) * 1985-09-28 1987-05-06 Interox Chemicals Limited Preparation of sulphophenyl esters
US4666636A (en) * 1985-10-28 1987-05-19 Monsanto Company Production of sodium phenol sulfonate
US5069828A (en) * 1989-06-06 1991-12-03 E. I. Du Pont De Nemours And Company Process for preparing benzenesulfonate salts

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