JP6266420B2 - Method for purifying dimethyl sulfoxide - Google Patents
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- JP6266420B2 JP6266420B2 JP2014087919A JP2014087919A JP6266420B2 JP 6266420 B2 JP6266420 B2 JP 6266420B2 JP 2014087919 A JP2014087919 A JP 2014087919A JP 2014087919 A JP2014087919 A JP 2014087919A JP 6266420 B2 JP6266420 B2 JP 6266420B2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 title claims description 250
- 238000000034 method Methods 0.000 title claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 239000002994 raw material Substances 0.000 claims description 38
- 238000002835 absorbance Methods 0.000 claims description 18
- 239000012153 distilled water Substances 0.000 claims description 5
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 5
- 239000012498 ultrapure water Substances 0.000 claims description 5
- 230000009965 odorless effect Effects 0.000 claims description 4
- 238000004821 distillation Methods 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 101000671819 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 36 Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 102100040109 Ubiquitin carboxyl-terminal hydrolase 36 Human genes 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- -1 for example Chemical compound 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000011085 pressure filtration Methods 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、医農薬中間体の反応溶剤や合成試薬等に幅広く使用されているジメチルスルホキシドの精製方法に関し、さらに詳しくは、米国薬局方（Ｕ．Ｓ．Ｐｈａｒｍａｃｏｐｅｉａ）の規格を満たし、かつ臭気を低減した高品質のジメチルスルホキシドを経済的かつ、収率良く精製する方法に関するものである。 The present invention relates to a method for purifying dimethyl sulfoxide, which is widely used as a reaction solvent, a synthesis reagent, and the like for pharmaceutical and agrochemical intermediates. More specifically, the present invention meets US Pharmacopoeia (US) Pharmacopeia standards and has an odor. The present invention relates to a method for purifying reduced high quality dimethyl sulfoxide economically and in a high yield.
ジメチルスルホキシドは、医農薬中間体の反応溶剤や合成試薬、あるいは電子材料等の特殊洗浄剤等として工業的に幅広く使用されている。なかでも米国薬局方に指定されているジメチルスルホキシドは、工業品質のジメチルスルホキシド以上に高純度であり、かつ臭気が少ないことが必要とされている。 Dimethyl sulfoxide is widely used industrially as a reaction solvent, a synthetic reagent for medical and agrochemical intermediates, or a special detergent for electronic materials. Among them, dimethyl sulfoxide designated by the United States Pharmacopeia is required to have higher purity and less odor than industrial dimethyl sulfoxide.
従来、ジメチルスルホキシドの精製方法としては、一般工業品質のジメチルスルホキシドに活性炭を接触させ、次いで蒸留処理を行う精製方法（例えば特許文献１参照）、一般工業品質のジメチルスルホキシドに活性炭を接触させ、次いで一部のジメチルスルホキシドを凝固させて固液分離した後、ジメチルスルホキシドを再度溶解させる精製方法（例えば特許文献２参照）、特殊な専用設備で一般工業品質のジメチルスルホキシドを凝固させて固液分離した後でジメチルスルホキシドを再度溶解させる晶析方法（例えば特許文献３参照）などが知られている。 Conventionally, as a purification method of dimethyl sulfoxide, activated carbon is brought into contact with general industrial quality dimethyl sulfoxide and then subjected to distillation treatment (see, for example, Patent Document 1), activated carbon is brought into contact with general industrial quality dimethyl sulfoxide, After solidifying a part of dimethyl sulfoxide by solid-liquid separation, a purification method (see, for example, Patent Document 2) for re-dissolving dimethyl sulfoxide, solid-liquid separation was performed by coagulating general industrial quality dimethyl sulfoxide with special dedicated equipment. A crystallization method (for example, see Patent Document 3) in which dimethyl sulfoxide is dissolved again later is known.
しかしながら、特許文献１の精製方法では、臭気を除去することができない。臭気は、米国薬局方の規格には設定されていないものの、医薬用ジメチルスルホキシドに事実上求められている重要な要求品質である。 However, the purification method of Patent Document 1 cannot remove odor. Odor is an important quality requirement for pharmaceutical dimethyl sulfoxide, although it is not set in US Pharmacopoeia standards.
特許文献２の精製方法では、ジメチルスルホキシドの晶析や溶解において専用設備が必要であり不経済である。 The purification method of Patent Document 2 is uneconomical because dedicated equipment is required for crystallization and dissolution of dimethyl sulfoxide.
特許文献３の精製方法では、ジメチルスルホキシドの融点が低いため（融点１８℃）、特殊な専用設備が必要となる上、ジメチルスルホキシドの収率が１５％と低く、工業的に不利である。 In the purification method of Patent Document 3, since the melting point of dimethyl sulfoxide is low (melting point: 18 ° C.), special dedicated equipment is required and the yield of dimethyl sulfoxide is as low as 15%, which is industrially disadvantageous.
本発明の目的は、このような問題点を解消し、米国薬局方の規格を満たし、かつ臭気を低減した高品質のジメチルスルホキシドを、経済的かつ、収率良く精製する方法を提供することにある。 The object of the present invention is to provide a method for resolving such problems and purifying high-quality dimethyl sulfoxide, which satisfies the standards of the United States Pharmacopeia and has reduced odor, economically and with good yield. is there.
上記課題を解決する本発明のジメチルスルホキシドの精製方法は、以下のいずれかの構成からなる。
（１）純度が９９．９重量％以上であるジメチルスルホキシドを原料として用い、この原料ジメチルスルホキシド１００重量部を、２５〜１００重量部の水の存在下で活性炭と接触させ、内温１１０℃℃以下で蒸留し、精製されたジメチルスルホキシドの２７５ｎｍにおける吸光度を、０．０１〜０．０８にすることを特徴とするジメチルスルホキシドの精製方法。
（２）前記原料ジメチルスルホキシド１００重量部に対し、前記活性炭を０．１〜１０重量部接触させることを特徴とする（１）に記載のジメチルスルホキシドの精製方法。
（３）前記水がイオン交換水、蒸留水または超純水であることを特徴とする（１）または（２）に記載のジメチルスルホキシドの精製方法。
（４）前記精製されたジメチルスルホキシドの臭気強度を、以下の測定方法；
３０ｍＬサンプル瓶にジメチルスルホキシドを１５ｍＬ入れ、同じサンプルをパネラー３人以上が室温下でサンプル瓶に鼻を近づけて嗅ぎ、下記に示す０〜５の６段階の基準で判定し、全員の判定値のうち多数の値を臭気強度とする：
臭気強度０： 無臭
臭気強度１： やっと感知できるにおい
臭気強度２： 何のにおいか判る弱いにおい
臭気強度３： 楽に感知できるにおい
臭気強度４： 強いにおい
臭気強度５： 強烈なにおい
で測定したとき、臭気強度１以下にすることを特徴とする（１）〜（３）のいずれか記載のジメチルスルホキシドの精製方法。
The method for purifying dimethyl sulfoxide of the present invention that solves the above problems comprises any one of the following constitutions.
(1) Using dimethyl sulfoxide having a purity of 99.9% by weight or more as a raw material, 100 parts by weight of this raw material dimethyl sulfoxide is brought into contact with activated carbon in the presence of 25 to 100 parts by weight of water, and the internal temperature is 110 ° C. A method for purifying dimethyl sulfoxide, characterized in that the absorbance at 275 nm of dimethyl sulfoxide distilled and purified below is 0.01 to 0.08 .
(2) The method for purifying dimethyl sulfoxide according to (1) , wherein 0.1 to 10 parts by weight of the activated carbon is brought into contact with 100 parts by weight of the raw material dimethyl sulfoxide .
(3) The method for purifying dimethyl sulfoxide according to (1) or (2), wherein the water is ion-exchanged water, distilled water or ultrapure water.
(4) The following method for measuring the odor intensity of the purified dimethyl sulfoxide;
15 mL of dimethyl sulfoxide is placed in a 30 mL sample bottle, and three or more panelists sniff the nose close to the sample bottle at room temperature at the room temperature. A number of values are used as odor intensity:
Odor intensity 0: Odorless
Odor intensity 1: A smell that can finally be detected
Odor intensity 2: A weak smell that tells what smell
Odor intensity 3: odor can be detected easily
Odor intensity 4: Strong smell
Odor intensity 5: Strong smell
The method for purifying dimethyl sulfoxide according to any one of (1) to (3), wherein the odor intensity is 1 or less as measured by 1.
本発明のジメチルスルホキシドの精製方法は、米国薬局方の規格項目である吸光度を改良するとともに、事実上の要求品質として求められる臭気を大幅に改良することができる。また、ジメチルスルホキシドと蒸留分離しやすい水の存在下で活性炭と接触させるだけなので収率良く高純度のジメチルスルホキシドを取得でき、しかも特殊な専用設備が不要であるため、経済的である。 The method for purifying dimethyl sulfoxide of the present invention can improve the absorbance, which is a standard item of the United States Pharmacopeia, and can greatly improve the odor required as a practically required quality. Further, since it is simply brought into contact with activated carbon in the presence of water that can be easily separated from dimethyl sulfoxide by distillation, it is economical because high-purity dimethyl sulfoxide can be obtained with high yield and no special dedicated equipment is required.
本発明のジメチルスルホキシドの精製方法は、米国薬局方の規格を満たし、かつその臭気を低減した高品質のジメチルスルホキシドを、経済的かつ、収率良く得る精製方法である。上述した通り、一般工業品レベルのジメチルスルホキシドを通常の方法で精製したのでは、米国薬局方の規格を満たすジメチルスルホキシドが得られたとしても臭気を除去することができなったため医薬用途に使用することは困難であった。臭気を除去するためには、特許文献２および３に記載されたように、専用設備が必要であり、精製コストが高いものであった。 The method for purifying dimethyl sulfoxide according to the present invention is a method for obtaining a high-quality dimethyl sulfoxide that satisfies the specifications of the US Pharmacopoeia and has reduced odor, economically and in a high yield. As described above, when dimethyl sulfoxide at the level of general industrial products is purified by a normal method, even if dimethyl sulfoxide satisfying US Pharmacopoeia standards is obtained, the odor cannot be removed and used for pharmaceutical purposes. It was difficult. In order to remove the odor, as described in Patent Documents 2 and 3, dedicated equipment is necessary, and the purification cost is high.
ここで、米国薬局方（Ｕ．Ｓ．Ｐｈａｒｍａｃｏｐｅｉａ ＵＳＰ３６、ＮＦ３１、３２６９ページ）では品質規格のひとつに２７５ｎｍの吸光度など、また、欧州薬局方（Ｅｕｒｏｐｅａｎ Ｐｈａｒｍａｃｏｐｅｉａ ７．０）においても２７５ｎｍの吸光度などが設定されている。一般工業品と薬局方品では２７５ｎｍの吸光度の差が最も大きいため、本明細書では、薬局方規格の代表値として２７５ｎｍの吸光度でジメチルスルホキシド品質を評価する。吸光度の測定は、紫外吸光光度計を使用し、幅１ｃｍのセルを使用し、水をブランクとする。ジメチルスルホキシドは事前に窒素バブリングを３０分間実施した後１０分以内に測定する。 Here, in the US Pharmacopoeia (US Pharmacopia USP36, NF31, p. 3269), one of the quality standards is 275 nm absorbance, and in the European Pharmacopoeia (European Pharmacopia 7.0), 275 nm absorbance is also set. Has been. Since the difference in absorbance at 275 nm is the largest between a general industrial product and a pharmacopoeia product, in this specification, the dimethyl sulfoxide quality is evaluated based on the absorbance at 275 nm as a representative value of the pharmacopoeia standard. The absorbance is measured using an ultraviolet absorptiometer, using a cell having a width of 1 cm, and using water as a blank. Dimethyl sulfoxide is measured within 10 minutes after 30 minutes of prior nitrogen bubbling.
また、ジメチルスルホキシドの臭気は、悪臭防止法等の臭気判定方法として使用されている６段階臭気強度表示法を用いる。この臭気強度表示法は、においの強さを下記に示す０〜５の６段階の判定基準で評価する方法であり、この方法に基づき応じてジメチルスルホキシドの臭気レベルを評価することができる。
臭気強度０： 無臭
臭気強度１： やっと感知できるにおい
臭気強度２： 何のにおいか判る弱いにおい
臭気強度３： 楽に感知できるにおい
臭気強度４： 強いにおい
臭気強度５： 強烈なにおい
Moreover, the odor of dimethyl sulfoxide uses the 6-step odor intensity display method currently used as odor determination methods, such as the malodor prevention method. This odor intensity display method is a method of evaluating the odor intensity by the following 6-step criteria of 0 to 5, and the odor level of dimethyl sulfoxide can be evaluated based on this method.
Odor intensity 0: Odorless Odor intensity 1: A smell that can be finally detected Odor intensity 2: A weak smell that can be detected by any smell Odor intensity 3: A smell that can be easily detected Odor intensity 4: Strong smell Odor intensity 5: Intense smell
ジメチルスルホキシドのにおいの嗅ぎ方としては、３０ｍＬサンプル瓶にジメチルスルホキシドを１５ｍＬ入れ、室温下でサンプル瓶に鼻を近づけ、同じサンプルをパネラー３人以上で嗅ぎ、全員の判定値のうち多数の値をサンプルの臭気強度とする。 To smell dimethyl sulfoxide, put 15 mL of dimethyl sulfoxide into a 30 mL sample bottle, bring the nose close to the sample bottle at room temperature, sniff the same sample with more than 3 panelists, The odor intensity of the sample.
本発明のジメチルスルホキシドの精製方法が処理対象にするジメチルスルホキシド（以下、「原料ジメチルスルホキシド」という。）は、一般工業品レベルのジメチルスルホキシドであり、原料ジメチルスルホキシドの純度は、９９．９重量％以上、好ましくは９９．９〜１００．０重量％である。このような純度の原料ジメチルスルホキシドを使用することにより、不純物の含有量が少なく米国薬局方の規格を満たし、かつ臭気がない高品質のジメチルスルホキシドを得ることができる。なお本明細書において、ジメチルスルホキシドの純度は、米国薬局方（Ｕ．Ｓ．Ｐｈａｒｍａｃｏｐｅｉａ ＵＳＰ３６、ＮＦ３１、３２６９ページ）に基づく方法でガスクロマトグラフにより測定するものとする。なお原料ジメチルスルホキシドには、ジメチルスルホキシドと蒸留で分離可能であれば、ジメチルスルホキシド以外の化合物を含んでいてもよい。 Dimethylsulfoxide method for purifying dimethyl sulfoxide present invention is to be processed (hereinafter, referred to as "raw material dimethyl sulfoxide.") Is Ri Oh dimethylsulfoxide general industrial products level, purity of the raw materials dimethyl sulfoxide, 99.9 wt% or more, good Mashiku the Ru 99.9 to 100.0% by weight der. By using the raw material dimethyl sulfoxide having such a purity, it is possible to obtain a high-quality dimethyl sulfoxide having a low impurity content and satisfying the standards of the US Pharmacopoeia and having no odor. In the present specification, the purity of dimethyl sulfoxide is measured by gas chromatography using a method based on the United States Pharmacopeia (US Pharmacopia USP36, NF31, p. 3269). The raw material dimethyl sulfoxide may contain a compound other than dimethyl sulfoxide as long as it can be separated from dimethyl sulfoxide by distillation.
本発明のジメチルスルホキシドの精製方法は、原料ジメチルスルホキシド１００重量部を、２５〜１００重量部の水の存在下で活性炭に接触させる。水が存在することにより、原料ジメチルスルホキシド中に微量含まれる不純物を除去しやすくなり、とりわけ臭気を大幅に低減することができる。水を原料ジメチルスルホキシドに添加しない場合や、水以外の溶媒を添加した場合には、ジメチルスルホキシドの吸光度を小さくすることおよび臭気を低減することができない。 In the method for purifying dimethyl sulfoxide of the present invention, 100 parts by weight of raw material dimethyl sulfoxide is brought into contact with activated carbon in the presence of 25 to 100 parts by weight of water. The presence of water makes it easy to remove impurities contained in a trace amount in the raw material dimethyl sulfoxide, and in particular, the odor can be greatly reduced. When water is not added to the raw material dimethyl sulfoxide, or when a solvent other than water is added, the absorbance of dimethyl sulfoxide cannot be reduced and the odor cannot be reduced.
原料ジメチルスルホキシドに添加する水としては、一般的に入手可能な水であれば良く、例えば水道水、工業用水、純水、スチーム凝縮水、蒸留水、イオン交換水、超純水等を例示することができる。好ましくはＪＩＳ−Ｋ０５５７におけるＡ４相当の水であるとよい。ＪＩＳ−Ｋ０５５７ Ａ４相当の水としては、蒸留水、イオン交換水、超純水を例示することができる。 The water added to the raw material dimethyl sulfoxide may be water that is generally available. Examples thereof include tap water, industrial water, pure water, steam condensed water, distilled water, ion-exchanged water, and ultrapure water. be able to. Preferably it is water corresponding to A4 in JIS-K0557. Examples of water corresponding to JIS-K0557 A4 include distilled water, ion exchange water, and ultrapure water.
原料ジメチルスルホキシドへの水の混合量は、原料ジメチルスルホキシド１００重量部に対し２５重量部以上、好ましくは３０重量部以上にする。水の混合量が、２５重量部より少ないと臭気改善効果を十分に得ることができない。水の混合量の上限は、原料ジメチルスルホキシド１００重量部に対し１００重量部にする。１００重量部を超える水を添加すると精製の生産性が悪化し、工業的に不利である。水の混合量は、２５〜１００重量部にする。 Mixing amount of water to the raw material dimethyl sulfoxide starting material dimethyl sulfoxide 100 parts by weight versus 2 5 parts by weight or more, good Mashiku is more than 30 parts by weight. If the amount of water mixed is less than 25 parts by weight, the effect of improving odor cannot be obtained sufficiently. The upper limit of the mixing amount of water is paired with 1 00 parts by weight to 100 parts by weight of the raw material dimethyl sulfoxide. If more than 100 parts by weight of water is added, purification productivity deteriorates, which is industrially disadvantageous. Mixing amount of water, you 2 5-100 parts by weight.
本発明では、原料ジメチルスルホキシドを水の存在下で活性炭と接触させることにより、原料ジメチルスルホキシド中の微量不純物を活性炭に吸着させることができる。なお、原料ジメチルスルホキシドを活性炭以外の吸着剤、例えばイオン交換樹脂、酸性白土、モレキュラーシーブ等に、水の存在下で接触させたとしてもジメチルスルホキシドの吸光度を小さくすることおよび臭気を低減することが容易ではない。 In this invention, the trace amount impurity in raw material dimethyl sulfoxide can be made to adsorb | suck to activated carbon by making raw material dimethyl sulfoxide contact with activated carbon in presence of water. Even if the raw material dimethyl sulfoxide is brought into contact with an adsorbent other than activated carbon, for example, ion exchange resin, acid clay, molecular sieve, etc. in the presence of water, the absorbance of dimethyl sulfoxide can be reduced and the odor can be reduced. It's not easy.
本発明において、使用する活性炭は、特に制限されるものではなく、粉末炭、粒状炭、繊維状炭のいずれでも良い。好ましくは粉末活性炭がよい。また活性炭の賦活方法は、主に薬品賦活法と水蒸気賦活法の２種類があり、好ましくは水蒸気賦活した活性炭がよい。薬品賦活した活性炭は、賦活時の薬品等がわずかに残存しており、薬品等の影響で満足な精製効果が得られない虞がある。 In the present invention, the activated carbon to be used is not particularly limited, and may be powdered coal, granular coal, or fibrous coal. Powdered activated carbon is preferable. There are mainly two types of activated carbon activation methods, a chemical activation method and a water vapor activation method, preferably water vapor activated activated carbon. The activated carbon activated by the chemical has a slight amount of chemical remaining at the time of activation, and there is a possibility that a satisfactory purification effect cannot be obtained due to the influence of the chemical or the like.
接触させる活性炭は、事前に水で洗浄してもよい。洗浄に使用する水は好ましくは中性、またはアルカリ性がよい。アルカリ性水溶液を用いる場合、アルカリ成分はアルカリ金属およびアルカリ土類金属の水酸化物、炭酸塩、重炭酸塩がよく、例えば水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を例示することができ、なかでも水酸化ナトリウム、水酸化カリウムが好ましい。 Activated carbon to be contacted may be washed with water in advance. The water used for washing is preferably neutral or alkaline. When an alkaline aqueous solution is used, the alkali component is preferably an alkali metal or alkaline earth metal hydroxide, carbonate or bicarbonate, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, carbonate. Examples thereof include potassium hydrogen, among which sodium hydroxide and potassium hydroxide are preferable.
原料ジメチルスルホキシドに接触させる活性炭の量は、原料ジメチルスルホキシド１００重量部に対し、好ましくは０．１重量部以上、より好ましくは０．５重量部以上である。活性炭の添加量が０．１重量部より少ないと蒸留して取得したジメチルスルホキシドの臭気改善効果と吸光度改善効果が低下する。また、活性炭の添加量の上限は、好ましくは２０．０重量部、より好ましくは１０．０重量部、さらに好ましくは５．０重量部である。活性炭の添加量が２０．０重量部を超えると流動性とろ過性が悪化し、工業的に不利である。 The amount of activated carbon brought into contact with the raw material dimethyl sulfoxide is preferably 0.1 parts by weight or more, more preferably 0.5 parts by weight or more with respect to 100 parts by weight of the raw material dimethyl sulfoxide. If the amount of the activated carbon added is less than 0.1 parts by weight, the odor improving effect and the absorbance improving effect of dimethyl sulfoxide obtained by distillation are reduced. Moreover, the upper limit of the addition amount of activated carbon becomes like this. Preferably it is 20.0 weight part, More preferably, it is 10.0 weight part, More preferably, it is 5.0 weight part. When the addition amount of activated carbon exceeds 20.0 parts by weight, fluidity and filterability are deteriorated, which is industrially disadvantageous.
原料ジメチルスルホキシドを水の存在下で活性炭と接触させる方法は、通常用いられる方法で行うことができる。活性炭の全量を原料ジメチルスルホキシドと水の混合液に一度に添加してもよいし、逐次、分割して添加してもよい。また混合液を適宜攪拌しながら活性炭を添加してもよい。さらに原料ジメチルスルホキシドに水を添加し混合液を調製した後、直ちに活性炭を添加してもよいし、時間をおいてから活性炭を添加してもよい。また、原料ジメチルスルホキシドに、水および活性炭を同時に添加してもよいし、水に原料ジメチルスルホキシドおよび活性炭を同時に添加してもよい。また、活性炭を充填したカラムに原料ジメチルスルホキシドと水の混合液を通液してもよい。 The method of bringing the raw material dimethyl sulfoxide into contact with activated carbon in the presence of water can be carried out by a commonly used method. The total amount of activated carbon may be added to the raw material dimethyl sulfoxide and water mixed solution at once, or may be added in divided portions sequentially. Moreover, you may add activated carbon, stirring a liquid mixture suitably. Further, after preparing water by adding water to the raw material dimethyl sulfoxide, activated carbon may be added immediately, or activated carbon may be added after a period of time. Moreover, water and activated carbon may be added simultaneously to the raw material dimethyl sulfoxide, or the raw material dimethyl sulfoxide and activated carbon may be added simultaneously to the water. Further, a mixed solution of raw material dimethyl sulfoxide and water may be passed through a column filled with activated carbon.
原料ジメチルスルホキシドおよび水の混合液と活性炭を接触させる温度は、特に制限されるものではないが、好ましくは８０℃以下、より好ましくは０〜４０℃にするとよい。８０℃より高い温度で接触させると活性炭への不純物吸着能力が低下し、吸光度および臭気の改善効果が低下する。０℃よりも低い温度で接触させる場合には、原料ジメチルスルホキシドおよび水を含む混合液を調製した後、混合液を冷却する必要があるため、経済的に非効率である。 The temperature at which the mixed solution of the raw material dimethyl sulfoxide and water and the activated carbon are brought into contact with each other is not particularly limited, but is preferably 80 ° C. or lower, more preferably 0 to 40 ° C. When contact is made at a temperature higher than 80 ° C., the ability to adsorb impurities on the activated carbon decreases, and the effect of improving absorbance and odor decreases. When contacting at a temperature lower than 0 ° C., it is economically inefficient because it is necessary to cool the mixed solution after preparing the mixed solution containing the raw material dimethyl sulfoxide and water.
また原料ジメチルスルホキシドを水の存在下で活性炭と接触させる時間は、特に制限されるものではないが、好ましくは１０分以上、より好ましくは３０分以上であるとよい。このような時間で原料ジメチルスルホキシドを活性炭と接触させることにより、臭気改善効果および吸光度改善効果を確実に得ることができる。また、原料ジメチルスルホキシド、水および活性炭を含む混合液を攪拌することにより、原料ジメチルスルホキシドを活性炭に効率的に接触させることができる。 The time for bringing the raw material dimethyl sulfoxide into contact with the activated carbon in the presence of water is not particularly limited, but is preferably 10 minutes or more, more preferably 30 minutes or more. By bringing the raw material dimethyl sulfoxide into contact with the activated carbon for such a time, an odor improving effect and an absorbance improving effect can be reliably obtained. Moreover, the raw material dimethyl sulfoxide can be efficiently brought into contact with the activated carbon by stirring the mixed solution containing the raw material dimethyl sulfoxide, water, and activated carbon.
本発明では、原料ジメチルスルホキシドを水の存在下で活性炭と接触させる工程の後、活性炭を固液分離し、ジメチルスルホキシドおよび水を含む混合液を蒸留することにより水を除去してジメチルスルホキシドを精製することができる。 In the present invention, after the step of bringing the raw material dimethyl sulfoxide into contact with activated carbon in the presence of water, the activated carbon is subjected to solid-liquid separation, and the mixed solution containing dimethyl sulfoxide and water is distilled to remove water and purify dimethyl sulfoxide. can do.
活性炭の固液分離は、通常行われる方法を用いることができ、例えば加圧ろ過、減圧ろ過、デカンテーション、遠心分離等を例示することができ、なかでも加圧ろ過が好ましい。ろ過に用いるフィルターは、活性炭を分離することができるものであれば特に制限されることはない。 For the solid-liquid separation of the activated carbon, a commonly performed method can be used. For example, pressure filtration, vacuum filtration, decantation, centrifugation and the like can be exemplified, and pressure filtration is particularly preferable. The filter used for filtration is not particularly limited as long as it can separate activated carbon.
本発明において、固液分離されたジメチルスルホキシドおよび水を含む混合液の蒸留としては、例えば高圧蒸留、低圧蒸留、減圧蒸留、分子蒸留、単蒸留、精留、連続蒸留、回分蒸留等を例示することができ、なかでも減圧での精留が好ましい。 In the present invention, examples of the distillation of the mixed liquid containing dimethyl sulfoxide and water separated by solid-liquid include high pressure distillation, low pressure distillation, vacuum distillation, molecular distillation, simple distillation, rectification, continuous distillation, batch distillation and the like. In particular, rectification under reduced pressure is preferred.
本発明において、ジメチルスルホキシドおよび水を含む混合液を蒸留する際の内温は、１１０℃以下である。内温１１０℃以下で蒸留することにより、ジメチルスルホキシドが分解するのを抑制し、かつ分解に起因する臭気の発生を防ぐことができる。 In the present invention, the inner temperature at the time of distilling the mixture containing dimethyl sulfoxide and water, is 1 10 ° C. or less. By distilling at an internal temperature of 110 ° C. or lower, it is possible to suppress decomposition of dimethyl sulfoxide and to prevent generation of odor due to decomposition.
また、ジメチルスルホキシドを減圧で蒸留するときの圧力は、好ましくは１４．２ｋＰａ以下、より好ましくは６．７ｋＰａ以下である。減圧して蒸留することにより、ジメチルスルホキシドの分解を抑制し、臭気の増加を抑制することができる。 Moreover, the pressure when distilling dimethyl sulfoxide under reduced pressure is preferably 14.2 kPa or less, more preferably 6.7 kPa or less. By distilling under reduced pressure, decomposition of dimethyl sulfoxide can be suppressed and increase in odor can be suppressed.
以下、実施例により本発明を具体的に説明するが、本発明はこれら実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to these Examples.
本実施例において、原料ジメチルスルホキシドの化学純度、精製処理によって得られたジメチルスルホキシド（以下、「精製ジメチルスルホキシド」という。）および原料ジメチルスルホキシドの吸光度および臭気強度は、以下の方法で測定した。 In this example, the chemical purity of raw dimethyl sulfoxide, the absorbance and odor intensity of dimethyl sulfoxide obtained by purification (hereinafter referred to as “purified dimethyl sulfoxide”) and raw dimethyl sulfoxide were measured by the following methods.
（原料ジメチルスルホキシドの純度の測定方法）
以下の条件のガスクロマトグラフ（島津社製ＧＣ−２０１０）により、原料ジメチルスルホキシドの化学純度を測定した。
分析装置 ：ＧＣ
キャリアガス ：ヘリウム （カラム流量１．７ｍＬ／分）
分析カラム ：ＲＥＳＴＥＫ社製Ｒｘｔ−１ （１５ｍ×０．３２ｍｍ×３μｍ）
カラム温度 ：１００℃（１５分）→（１０℃／分）→１７０℃（２０分）
注入口温度 ：２１０℃
注入量 ：１μＬ
検出器 ：ＦＩＤ
検出器温度 ：２２０℃
(Method for measuring purity of raw material dimethyl sulfoxide)
The chemical purity of the raw material dimethyl sulfoxide was measured by a gas chromatograph (GC-2010 manufactured by Shimadzu Corporation) under the following conditions.
Analyzer: GC
Carrier gas: Helium (column flow rate 1.7 mL / min)
Analysis column: Rxt-1 (15 m × 0.32 mm × 3 μm) manufactured by RESTEK
Column temperature: 100 ° C. (15 minutes) → (10 ° C./minute)→170° C. (20 minutes)
Inlet temperature: 210 ° C
Injection volume: 1 μL
Detector: FID
Detector temperature: 220 ° C
（精製ジメチルスルホキシドおよび原料ジメチルスルホキシドの吸光度の測定方法）
ジメチルスルホキシドを事前に窒素バブリングを３０分間実施し、その後１０分以内に、紫外吸光光度計（島津社製ＵＶ−１８００）を使用し、以下の条件で２７５ｎｍの吸光度を測定した。
分析装置 ：紫外吸光光度計
セル ：石英、幅１ｃｍ
ブランク ：水
(Measurement method of absorbance of purified dimethyl sulfoxide and raw material dimethyl sulfoxide)
Nitrogen bubbling of dimethyl sulfoxide was performed in advance for 30 minutes, and then within 10 minutes, an ultraviolet absorptiometer (UV-1800 manufactured by Shimadzu Corporation) was used, and absorbance at 275 nm was measured under the following conditions.
Analyzer: UV absorption photometer Cell: Quartz, width 1cm
Blank: Water
（精製ジメチルスルホキシドおよび原料ジメチルスルホキシドの臭気強度の測定方法）
ジメチルスルホキシドの臭気を、下記に示す６段階の臭気強度表示法に基づき３人のパネラーが官能評価した。３０ｍＬサンプル瓶に、ジメチルスルホキシドを１５ｍＬ入れサンプルとした。パネラー３人が同じサンプルの臭気を、室温下でサンプル瓶に鼻を近づけて嗅ぎ、下記に示す０〜５の６段階の基準で判定し、３人の判定値のうち多数の値をサンプルの臭気強度とした。
臭気強度０： 無臭
臭気強度１： やっと感知できるにおい
臭気強度２： 何のにおいか判る弱いにおい
臭気強度３： 楽に感知できるにおい
臭気強度４： 強いにおい
臭気強度５： 強烈なにおい
(Measurement method of odor intensity of purified dimethyl sulfoxide and raw material dimethyl sulfoxide)
The odor of dimethyl sulfoxide was sensorially evaluated by three panelists based on the following six-step odor intensity display method. A sample of 15 mL of dimethyl sulfoxide was placed in a 30 mL sample bottle. Three panelists sniff the odor of the same sample with the nose close to the sample bottle at room temperature, and judged on the basis of 6 levels of 0 to 5 shown below. Odor intensity was set.
Odor intensity 0: Odorless Odor intensity 1: A smell that can be finally detected Odor intensity 2: A weak smell that can be detected by any smell Odor intensity 3: A smell that can be easily detected Odor intensity 4: Strong smell Odor intensity 5: Intense smell
（実施例１）
１１０ｍＬサンプル瓶に純度９９．９重量％の一般工業品質のジメチルスルホキシド（２７５ｎｍにおける吸光度が０．２２、臭気強度が３）５０ｇとＪＩＳ−Ｋ０５５７のＡ４相当のイオン交換水５０ｇ（１００重量部／ジメチルスルホキシド１００重量部）、粉末活性炭（日本エンバイロケミカルズ社製）０．５ｇ（１．０重量部／ジメチルスルホキシド１００重量部）を仕込み、室温下で１時間撹拌した。この混合液を０．４５μｍのフィルターに通液し活性炭を除去した。得られたろ液を、２００ｍＬ丸底フラスコに移し、丸底フラスコの口にラシヒリング（長さ５ｍｍ、内径３ｍｍ、外径５ｍｍ）を１０ｃｍ充填した直径３ｃｍ、高さ１５ｃｍの精留管を設置し、６．７ｋＰａで減圧蒸留した。丸底フラスコの内温４５℃から加熱を開始し、温度が１０７℃に到達した時点で受器を交換し、４０ｇの精製ジメチルスルホキシドを得た。この時の蒸留収率は８０％であった。得られた精製ジメチルスルホキシドの２７５ｎｍにおける吸光度は０．０８であり、臭気強度は１であった。これらの結果を表１にまとめて示す。なお表中、水および活性炭の添加量の単位は、ジメチルスルホキシドを１００重量部としたときの重量部として記載する。
Example 1
In a 110 mL sample bottle, 50 g of general industrial quality dimethyl sulfoxide having a purity of 99.9 wt% (absorbance at 275 nm is 0.22 and odor intensity is 3) and 50 g of ion-exchanged water equivalent to JIS-K0557 A4 (100 parts by weight / dimethyl) 100 parts by weight of sulfoxide) and 0.5 g (1.0 part by weight / 100 parts by weight of dimethylsulfoxide) of powdered activated carbon (manufactured by Nippon Envirochemicals) were charged and stirred at room temperature for 1 hour. This mixed solution was passed through a 0.45 μm filter to remove activated carbon. The obtained filtrate was transferred to a 200 mL round bottom flask, and a rectifying tube having a diameter of 3 cm and a height of 15 cm in which a Raschig ring (length 5 mm, inner diameter 3 mm, outer diameter 5 mm) was filled 10 cm in the mouth of the round bottom flask was installed. Distilled under reduced pressure at 6.7 kPa. Heating was started from the internal temperature of 45 ° C. of the round bottom flask, and when the temperature reached 107 ° C., the receiver was exchanged to obtain 40 g of purified dimethyl sulfoxide. The distillation yield at this time was 80%. The obtained purified dimethyl sulfoxide had an absorbance at 275 nm of 0.08 and an odor intensity of 1. These results are summarized in Table 1. In the table, the unit of addition amount of water and activated carbon is described as parts by weight with 100 parts by weight of dimethyl sulfoxide.
（実施例２〜５）
水の添加量または活性炭の添加量を、表１に記載するように変更したことを除き、実施例１と同様の精製操作を行った。実施例２，３，４および５の蒸留収率は、８１％，７９％，８０％および７９％であった。得られた精製ジメチルスルホキシドの品質を、表１に記載する。
(Examples 2 to 5)
The same purification operation as in Example 1 was performed except that the addition amount of water or the addition amount of activated carbon was changed as described in Table 1. The distillation yields of Examples 2, 3, 4 and 5 were 81%, 79%, 80% and 79%. The quality of the purified dimethyl sulfoxide obtained is listed in Table 1.
（実施例６〜７）
実施例１において、添加する水の種類を、ＪＩＳ−Ｋ０５５７のＡ４相当の蒸留水または超純水に変更したことを除き、実施例１と同様の精製操作を行った。実施例６および７の蒸留収率は、８０％および８１％であった。得られた精製ジメチルスルホキシドの品質を、表１に記載する。
(Examples 6 to 7)
In Example 1, the same purification operation as in Example 1 was performed, except that the kind of water to be added was changed to distilled water or ultrapure water corresponding to A4 of JIS-K0557. The distillation yields of Examples 6 and 7 were 80% and 81%. The quality of the purified dimethyl sulfoxide obtained is listed in Table 1.
（比較例１〜３）
比較例１，２は、表２に記載するように水の添加量を変更したことを除き、実施例１と同様の操作を行った。また比較例３は、水の代わりにメタノール（ナカライテスク社製特級）を添加したことを除き、実施例１と同様の操作を行った。比較例１，２および３の蒸留収率は、８５％，９５％および９５％であった。得られたジメチルスルホキシドの品質は表２の通りである。
(Comparative Examples 1-3)
In Comparative Examples 1 and 2, the same operation as in Example 1 was performed except that the amount of water added was changed as described in Table 2. Moreover, the comparative example 3 performed operation similar to Example 1 except having added methanol (special grade by Nacalai Tesque) instead of water. The distillation yields of Comparative Examples 1, 2, and 3 were 85%, 95%, and 95%. Table 2 shows the quality of the obtained dimethyl sulfoxide.
（比較例４）
純度９９．９重量％の工業品ジメチルスルホキシド５０ｇとＪＩＳ−Ｋ０５５７のＡ４相当のイオン交換水５０ｇ（１００重量部／ジメチルスルホキシド１００重量部）の混合液を調製した。ロートの足にウォセップ（東レ社製高性能油吸着材）５ｇを詰め、そこへ得られた混合液を３時間かけて通液させた。その混合液を用いて実施例１と同様の蒸留操作を行った。この時の蒸留収率は８０％であった。得られたジメチルスルホキシドの品質は表２の通りである。
(Comparative Example 4)
A mixed solution of 50 g of industrial dimethyl sulfoxide having a purity of 99.9% by weight and 50 g of ion-exchanged water corresponding to A4 of JIS-K0557 (100 parts by weight / 100 parts by weight of dimethyl sulfoxide) was prepared. The foot of the funnel was filled with 5 g of Wasep (a high performance oil adsorbent manufactured by Toray Industries, Inc.), and the resulting mixed liquid was allowed to flow there over 3 hours. Distillation operation similar to Example 1 was performed using the liquid mixture. The distillation yield at this time was 80%. Table 2 shows the quality of the obtained dimethyl sulfoxide.
（比較例５、６）
陽イオン交換樹脂または陰イオン交換樹脂からなるイオン交換樹脂（ピュロライト社製）３０ｍＬをカラムに充填した。陽イオン交換樹脂の場合は５％ＨＣｌ水溶液、陰イオン交換樹脂の場合は５％ＮａＯＨ水溶液を５００ｍＬカラム底部より通液した後、イオン交換水で中性になるまでそれぞれ洗浄した。実施例１において、粉末活性炭０．５ｇを上記で洗浄したイオン交換樹脂５ｇに変更したこと以外は、実施例１と同様の操作を行った。比較例５および６における蒸留収率は、いずれも７９％であった。得られたジメチルスルホキシドの品質は表２の通りである。
(Comparative Examples 5 and 6)
A column was packed with 30 mL of an ion exchange resin (manufactured by Purolite) consisting of a cation exchange resin or anion exchange resin. In the case of a cation exchange resin, a 5% HCl aqueous solution was passed through from the bottom of a 500 mL column in the case of an anion exchange resin, and then washed with ion exchange water until neutrality. In Example 1, the same operation as in Example 1 was performed except that 0.5 g of powdered activated carbon was changed to 5 g of the ion exchange resin washed above. The distillation yields in Comparative Examples 5 and 6 were both 79%. Table 2 shows the quality of the obtained dimethyl sulfoxide.
（比較例７）
実施例１において、粉末活性炭０．５ｇの代わりに乾燥させたモレキュラーシーブ４Ａ（ナカライテスク社製）５ｇに変更したこと以外は実施例１と同様の操作を行った。この時の蒸留収率は８０％であった。得られたジメチルスルホキシドの品質は表２の通りである。
(Comparative Example 7)
In Example 1, the same operation as Example 1 was performed except having changed to 5 g of dried molecular sieve 4A (manufactured by Nacalai Tesque) instead of 0.5 g of powdered activated carbon. The distillation yield at this time was 80%. Table 2 shows the quality of the obtained dimethyl sulfoxide.
（比較例８）
実施例１において、蒸留温度を５５〜１３５℃に変更したこと以外は同様の操作を行った。この時の蒸留収率は８０％であった。得られたジメチルスルホキシドの品質は表２の通りである。
(Comparative Example 8)
In Example 1, the same operation was performed except that the distillation temperature was changed to 55 to 135 ° C. The distillation yield at this time was 80%. Table 2 shows the quality of the obtained dimethyl sulfoxide.
Claims (4)
３０ｍＬサンプル瓶にジメチルスルホキシドを１５ｍＬ入れ、同じサンプルをパネラー３人以上が室温下でサンプル瓶に鼻を近づけて嗅ぎ、下記に示す０〜５の６段階の基準で判定し、全員の判定値のうち多数の値を臭気強度とする：15 mL of dimethyl sulfoxide is placed in a 30 mL sample bottle, and three or more panelists sniff the nose close to the sample bottle at room temperature at the room temperature. A number of values are used as odor intensity:
臭気強度０： 無臭Odor intensity 0: Odorless
臭気強度１： やっと感知できるにおいOdor intensity 1: A smell that can finally be detected
臭気強度２： 何のにおいか判る弱いにおいOdor intensity 2: A weak smell that tells what smell
臭気強度３： 楽に感知できるにおいOdor intensity 3: odor can be detected easily
臭気強度４： 強いにおいOdor intensity 4: Strong smell
臭気強度５： 強烈なにおいOdor intensity 5: Strong smell
で測定したとき、臭気強度１以下にすることを特徴とする請求項１〜３のいずれか記載のジメチルスルホキシドの精製方法。The method for purifying dimethyl sulfoxide according to any one of claims 1 to 3, wherein the odor intensity is 1 or less when measured by the method.
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