JPH0461870B2 - - Google Patents
Info
- Publication number
- JPH0461870B2 JPH0461870B2 JP59052263A JP5226384A JPH0461870B2 JP H0461870 B2 JPH0461870 B2 JP H0461870B2 JP 59052263 A JP59052263 A JP 59052263A JP 5226384 A JP5226384 A JP 5226384A JP H0461870 B2 JPH0461870 B2 JP H0461870B2
- Authority
- JP
- Japan
- Prior art keywords
- olefin
- chlorohydrin
- aqueous solution
- saponification
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 45
- 150000001336 alkenes Chemical class 0.000 claims description 44
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims description 31
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 238000001223 reverse osmosis Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000012528 membrane Substances 0.000 claims description 8
- 239000000920 calcium hydroxide Substances 0.000 claims description 7
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- -1 olefin chlorohydrins Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Description
【発明の詳細な説明】
本発明は、オレフインオキサイドの製造方法、
更に詳しくは、オレフインクロルヒドリンをアル
カリによりけん化反応させてオレフインオキサイ
ドを製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for producing olefin oxide,
More specifically, the present invention relates to a method for producing olefin oxide by saponifying olefin chlorohydrin with an alkali.
オレフインオキサイドは、従来、オレフインク
ロルヒドリン水溶液のアルカリによるけん化反応
により製造されているが、オレフインクロルヒド
リン水溶液は、一般に稀薄な濃度で使用されてい
る。これはオレフインクロルヒドリン製造時に副
生する多塩素化合物の副生率を抑えるために、経
済性を考慮しながらも、やむをえずとられている
工業的処置である。その濃度は、一般に３〜６重
量％程度と相当に低い。このような稀薄なオレフ
インクロルヒドリン水溶液を使用するので、けん
化時に多大の熱量が必要であり、生成したオレフ
インオキサイドが多量に存在する水と反応し、グ
リコール、グリセリン類となる副反応も促進され
る。また、けん化反応後のアルカリ塩、副生物を
含む廃液処理にも多大のエネルギーを必要とす
る。 Olefin oxide has conventionally been produced by saponifying an aqueous solution of olefin chlorohydrin with an alkali, but the aqueous solution of olefin chlorohydrin is generally used at a dilute concentration. This is an unavoidable industrial measure taken in consideration of economic efficiency in order to suppress the by-product rate of polychlorine compounds produced during the production of olefin chlorohydrin. Its concentration is generally quite low, about 3 to 6% by weight. Since such a dilute aqueous solution of olefin chlorohydrin is used, a large amount of heat is required during saponification, and the produced olefin oxide reacts with a large amount of water, promoting side reactions to form glycols and glycerins. Ru. In addition, a large amount of energy is required to treat waste liquid containing alkali salts and byproducts after the saponification reaction.
従来技術のこれら問題を解決するために高濃度
オレフインクロルヒドリン水溶液の製造方法およ
び、それを使用する方法の研究が数多くなされて
いる。これらの方法では、主として従来のオレフ
インクロルヒドリン製造工程からの稀薄水溶液を
蒸留、抽出、抽出蒸留などで濃縮している。しか
し、これらの方法で問題となるのは、オレフイン
クロルヒドリンを濃縮する際に水蒸気、抽出溶剤
などを多量に使用しなければならないことであ
る。例えば、一般に、従来技術でのオレフインク
ロルヒドリンの経済濃度は３〜６重量％程度とさ
れており、このような稀薄なオレフインクロルヒ
ドリン水溶液から高濃度オレフインクロルヒドリ
ン水溶液を得るための通常の方法としては蒸留法
がある。蒸留法で問題となるのは、ボトム中のオ
レフインクロルヒドリンの回収である。すなわ
ち、稀薄なオレフインクロルヒドリン水溶液から
オレフインクロルヒドリンを濃縮してボトム中の
オレフインクロルヒドリン濃度を低くしようとす
るには、多量の水蒸気を使用して、多段の蒸留塔
が必要である。結局、蒸留法は使用蒸気量が多
く、設備費の高いことが問題である。また、溶剤
抽出によりオレフインクロルヒドリンを取り出す
方法もあるが、稀薄で親水性のオレフインクロル
ヒドリンを水中から抽出するには蒸留法以上の設
備と大容量の抽出溶剤の回収等が必要であり、実
際的でない。 In order to solve these problems of the prior art, many studies have been conducted on methods for producing highly concentrated olefin chlorohydrin aqueous solutions and methods for using the same. In these methods, a dilute aqueous solution mainly obtained from the conventional olefin chlorohydrin production process is concentrated by distillation, extraction, extractive distillation, or the like. However, a problem with these methods is that a large amount of steam, extraction solvent, etc. must be used when concentrating olefin chlorohydrin. For example, in general, the economic concentration of olefin chlorohydrin in the prior art is about 3 to 6% by weight, and the conventional method for obtaining a highly concentrated olefin chlorohydrin aqueous solution from such a dilute olefin chlorohydrin aqueous solution is One method is the distillation method. The problem with the distillation method is the recovery of olefin chlorohydrin from the bottom. That is, in order to condense olefin chlorohydrin from a dilute aqueous solution of olefin chlorohydrin and lower the concentration of olefin chlorohydrin in the bottom, a large amount of water vapor is used and a multi-stage distillation column is required. . Ultimately, the problem with the distillation method is that it uses a large amount of steam and the equipment cost is high. There is also a method of extracting olefin chlorohydrin by solvent extraction, but extracting dilute and hydrophilic olefin chlorohydrin from water requires equipment beyond the distillation method and recovery of a large volume of extraction solvent. , impractical.
これらの欠点を改善するため、例えば、特開昭
56−113773号ではオレフインクロルヒドリン水溶
液を蒸留濃縮することによつて得られたオレフイ
ンクロルヒドリンを水蒸気または不活性ガス含有
水蒸気を同伴したガス状で棚段塔、充填塔などを
使用する塔式けん化工程へ装入し、石灰乳、カ性
ソーダ水溶液などのようなアルカリ液と向流接触
させて、けん化反応を行なうことから成るオレフ
インオキサイドの製造方法が提案されている。し
かし、この方法でも数％のオレフインクロルヒド
リン水溶液を数十％まで蒸留濃縮するには多大の
エネルギーを必要とする。 In order to improve these shortcomings, for example,
In No. 56-113773, olefin chlorohydrin obtained by distilling and concentrating an aqueous solution of olefin chlorohydrin is converted into a gaseous state accompanied by steam or steam containing an inert gas, using a plate column, a packed column, etc. A method for producing olefin oxide has been proposed, which comprises charging the olefin oxide to a saponification process and bringing it into countercurrent contact with an alkaline solution such as milk of lime or an aqueous caustic soda solution to carry out the saponification reaction. However, even with this method, a large amount of energy is required to distill and concentrate a few percent olefin chlorohydrin aqueous solution to several tens of percent.
本発明者らは、従来法のこのような欠点を改善
しうる方法を種々検討した結果、稀薄オレフイン
クロルヒドリン水溶液を一般の逆浸透膜を使用す
ることにより容易に高濃度に濃縮しうることを見
出し、本発明に到つた。 The present inventors have investigated various ways to improve these drawbacks of conventional methods, and have found that a dilute olefin chlorohydrin aqueous solution can be easily concentrated to a high concentration by using a general reverse osmosis membrane. They discovered this and arrived at the present invention.
すなわち、本発明はオレフインクロルヒドリン
水溶液をけん化してオレフインオキサイドを製造
するに際し、オレフインクロルヒドリンを逆浸透
膜により５重量％以上に濃縮してのち、石灰乳に
よりけん化することを特徴とするオレフインオキ
サイドの製造方法である。 That is, the present invention is characterized in that when saponifying an aqueous solution of olefin chlorohydrin to produce olefin oxide, the olefin chlorohydrin is concentrated to 5% by weight or more using a reverse osmosis membrane, and then saponified with milk of lime. This is a method for producing olefin oxide.
本発明の方法のように逆浸透膜で濃縮すると、
この分離技術が被処理液に凝縮剤を加えたり、熱
を加えたりすることなく、唯圧力を加えるだけで
分離する方法であるので、分離されたそれぞれの
成分は変性したり、変質したりした余分な不純物
の混入がない。 When concentrated using a reverse osmosis membrane as in the method of the present invention,
This separation technology does not add a condensing agent or heat to the liquid to be treated, and only applies pressure, so each separated component is free from denaturation or deterioration. No extra impurities mixed in.
また、この濃縮法は省エネルギ化、クローズド
化にも都合のよい分離技術であり、本発明の方法
は工業的方法として優れたものである。 Moreover, this concentration method is a separation technique that is convenient for energy saving and closed system, and the method of the present invention is excellent as an industrial method.
本発明の方法に使用される逆浸透膜は、特に限
定されることはない。また分離装置はいかなる型
式のものであつても良く、例えば平膜型、スパイ
ラル型、チユーブラー型、フオローフアイバー型
の各種装置が適用できる。 The reverse osmosis membrane used in the method of the present invention is not particularly limited. Further, the separation device may be of any type, such as a flat membrane type, a spiral type, a tubular type, and a fiber optic type.
本発明の方法に使用するオレフインクロルヒド
リン水溶液は、水中において塩素とオレフインを
反応させて得られるものをそのまま使用できる
が、必要により炭酸カルシウムのような不溶性炭
酸塩を添加して共存する酸を中和後に濃縮するこ
とが望ましい。 The olefin chlorohydrin aqueous solution used in the method of the present invention can be obtained by reacting chlorine and olefin in water and can be used as it is, but if necessary, an insoluble carbonate such as calcium carbonate may be added to remove the coexisting acid. It is desirable to concentrate after neutralization.
このようなオレフインクロルヒドリン水溶液
を、前記各種の逆浸透膜の分離装置で、少なくと
も５％以上に濃縮する。また透過液は、ほとんど
不純物を含んでおらず再利用可能である。 Such an aqueous olefin chlorohydrin solution is concentrated to at least 5% using the various types of reverse osmosis membrane separators described above. Furthermore, the permeate contains almost no impurities and can be reused.
つぎに、濃縮したオレフインクロルヒドリン水
溶液を石灰乳によりけん化反応を行なう。 Next, the concentrated olefin chlorohydrin aqueous solution is subjected to a saponification reaction using milk of lime.
濃縮されたオレフインクロルヒドリン水溶液の
石灰乳によるけん化は各種の方法で行なうことが
できる。 Saponification of a concentrated aqueous olefin chlorohydrin solution using milk of lime can be carried out by various methods.
本発明の方法によりプロピレンクロルヒドリ
ン、ジクロルプロパノールのようなオレフインク
ロルヒドリンから、プロピレンオキサイド、エピ
クロルヒドリンのような対応するオレフインオキ
サイドを製造することができる。 By the method of the present invention, corresponding olefin oxides such as propylene oxide and epichlorohydrin can be produced from olefin chlorohydrins such as propylene chlorohydrin and dichloropropanol.
本発明の方法によれば、従来法に比べ著しい使
用蒸気量の削減、けん化収率の向上、けん化設備
の小型化、さらにけん化廃液量も大幅に減少す
る。またけん化によつて得られる副生塩も高濃度
のものが得られるため、副生塩の商品化が容易と
なる。 According to the method of the present invention, compared to conventional methods, the amount of steam used is significantly reduced, the saponification yield is improved, the saponification equipment is made smaller, and the amount of saponification waste liquid is also significantly reduced. Moreover, since the by-product salt obtained by saponification can be obtained in a high concentration, commercialization of the by-product salt becomes easy.
以下、本発明を実施例および比較例により更に
具体的に説明する。 Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
実施例 １
4.0重量パーセントのプロピレンクロルヒドリ
ン水溶液を第１図に示す逆浸透装置２で濃縮分離
した後、けん化装置３によりプロピレンオキサイ
ドを製造した。Example 1 A 4.0 weight percent propylene chlorohydrin aqueous solution was concentrated and separated using a reverse osmosis device 2 shown in FIG. 1, and then propylene oxide was produced using a saponification device 3.
4.0重量％のプロピレンクロルヒドリン水溶液
80Kg／hrを導管１より30℃、40Kg／cm2Ｇで逆浸透
装置２へ装入した。 4.0% by weight propylene chlorohydrin aqueous solution
80 kg/hr was charged into reverse osmosis device 2 from conduit 1 at 30° C. and 40 kg/cm 2 G.
逆浸透装置はDDS−HF−40型を、逆浸透膜
は、DDS−HR−95を使用した。 The reverse osmosis device used was DDS-HF-40 type, and the reverse osmosis membrane used was DDS-HR-95.
導管４を通してプロピレンクロルヒドリン21.0
重量％、塩化カルシウム12.4重量％を含む濃縮液
15.15Kg／hrが得られた。 Propylene chlorohydrin 21.0 through conduit 4
% by weight, concentrate containing 12.4% by weight of calcium chloride
15.15Kg/hr was obtained.
導管５より得られる透過液中のプロピレンクロ
ルヒドリンは0.1重量％以下であり、塩化カルシ
ウムも微量であつた。導管４を通して濃縮液を洩
れ棚段式けん化塔３へ供給した。けん化塔は直径
40mm、13段のシーブトレイ式棚段塔で、上から４
段目に導管４より70℃、21.0重量％のプロピレン
クロルヒドリン水溶液を15.15Kg／hrで、また導
管６を経て最上段に70℃、15重量％の石灰乳を
10.03Kg／hrで供給し、塔底より3.3Kg／cm2Ｇの水
蒸気4.0Kg／hrを導入してけん化反応を行なつた。 The permeate obtained from conduit 5 contained less than 0.1% by weight of propylene chlorohydrin, and also contained a trace amount of calcium chloride. The concentrated liquid leaked through the conduit 4 and was supplied to the plated saponification tower 3. The diameter of the saponification tower
40mm, 13-tier sieve tray type plate tower, 4 from the top
A 21.0% by weight propylene chlorohydrin aqueous solution was added at 15.15 kg/hr from conduit 4 at 70°C, and milk of lime at 70°C and 15% by weight was added to the top stage via conduit 6.
The saponification reaction was carried out by supplying water at a rate of 10.03 Kg/hr and introducing 4.0 Kg/hr of steam at 3.3 Kg/cm 2 G from the bottom of the column.
塔頂からプロピレンオキサイドを含む水蒸気を
凝縮器で液化し、導管７より取り出し、一部反応
塔上部に還流した。 Steam containing propylene oxide from the top of the tower was liquefied in a condenser, taken out through conduit 7, and partially refluxed to the upper part of the reaction tower.
けん化廃水量は26.5Kg／hrであり、プロピレン
グリコール900ppm、塩化カルシウム14.1重量％
であつた。またけん化時のプロピレンオキサイド
収率は99.0％であつた。 Saponification wastewater amount is 26.5Kg/hr, propylene glycol 900ppm, calcium chloride 14.1% by weight
It was hot. Furthermore, the propylene oxide yield during saponification was 99.0%.
比較例 １
4.0重量％のプロピレンクロルヒドリン水溶液
を第２図に示す型式の直径100mm、11段のシーブ
トレイ式棚段塔１１で蒸留した。Comparative Example 1 A 4.0% by weight aqueous propylene chlorohydrin solution was distilled in a 11-stage sieve tray plate column 11 with a diameter of 100 mm as shown in FIG.
4.0重量％のプロピレンクロルヒドリン水溶液
を導管１により80℃、80Kg／hrで塔頂から３段目
に装入し、塔底から導管９により16Kg／hrの水蒸
気を吹込んだ。塔頂よりプロピレンクロルヒドリ
ン21.4重量％を含む14.80Kg／hrの水蒸気混合ガ
スを得た。塔底液は導管１０より取り出され、プ
ロピレクロルヒドリン200ppm、副生プロピレン
グリコールを20ppm含んでいた。プロピレンクロ
ルヒドリン回収率は99.0％であつた。 A 4.0% by weight propylene chlorohydrin aqueous solution was charged into the third stage from the top of the column at 80° C. through conduit 1 at 80 kg/hr, and steam was blown at 16 kg/hr from the bottom of the column through conduit 9. A steam mixed gas containing 21.4% by weight of propylene chlorohydrin at a rate of 14.80 kg/hr was obtained from the top of the column. The bottom liquid was taken out through conduit 10 and contained 200 ppm of propylechlorohydrin and 20 ppm of by-product propylene glycol. The propylene chlorohydrin recovery rate was 99.0%.
以下、実施例１に準じてけん化反応を行ない、
実施例１と同様の結果を得た。 Hereinafter, a saponification reaction was carried out according to Example 1,
The same results as in Example 1 were obtained.
比較例 ２
4.0重量％のプロピレンクロルヒドリン水溶液
を第３図に示す型式の、直径70mm、13段の洩れ棚
段式けん化塔３でけん化反応を行なつた。導管１
を経て塔頂より４段目に70℃、4.0重量％のプロ
ピレンクロルヒドリン水溶液を80Kg／hrで、導管
６より最上段に70℃、15重量％の石灰乳10.03
Kg／hrを供給し、塔底に3.3Kg／cm2Ｇの水蒸気
10.0Kg／hrを吹き込んでけん化反応を行なつた。
塔頂よりプロピレンオキサイドを含む水蒸気を凝
縮器で液化し、７より取り出し、一部反応塔上部
に還流した。Comparative Example 2 A 4.0% by weight propylene chlorohydrin aqueous solution was subjected to a saponification reaction in a leaking plate type saponification tower 3 having a diameter of 70 mm and 13 stages as shown in FIG. conduit 1
70℃, 4.0% by weight propylene chlorohydrin aqueous solution is added at 80kg/hr to the fourth stage from the top of the column, and 70℃, 15% by weight milk of lime 10.03 to the top stage from conduit 6.
Kg/hr and 3.3Kg/cm 2 G of steam at the bottom of the tower.
The saponification reaction was carried out by blowing 10.0 Kg/hr.
Steam containing propylene oxide from the top of the column was liquefied in a condenser, taken out from 7, and partially refluxed to the upper part of the reaction column.
この際、けん化廃水量は94Kg／hrであり、プロ
ピレングリコール500ppm、塩化カルシウム4.0重
量％であつた。 At this time, the amount of saponified wastewater was 94 kg/hr, and the content was 500 ppm of propylene glycol and 4.0% by weight of calcium chloride.
またプロピレンオキサイド収率は98.0％であつ
た。 Moreover, the propylene oxide yield was 98.0%.
第１図は、実施例１の反応を実施するのに用い
た反応装置のフローシートを、第２図は比較例１
の反応を実施するのに用いた反応装置のフローシ
ートを、また第３図は比較例２を実施するのに用
いた反応装置のフローシートを示す。
図中、１はオレフインクロルヒドリンの導入ラ
イン、２は逆浸透装置、３はけん化装置、４はオ
レフインクロルヒドリン濃縮液の導入ライン、５
は透過液の排出ライン、６は石灰乳導入ライン、
７はオレフインオキサイドの取り出しライン、８
は還流ライン、９は塔底液の排出ライン、１０は
水蒸気ラインを示す。
Figure 1 shows the flow sheet of the reactor used to carry out the reaction of Example 1, and Figure 2 shows the flow sheet of the reaction apparatus used in Comparative Example 1.
FIG. 3 shows a flow sheet of the reactor used to carry out the reaction of Comparative Example 2. In the figure, 1 is an introduction line for olefin chlorohydrin, 2 is a reverse osmosis device, 3 is a saponification device, 4 is an introduction line for olefin chlorohydrin concentrate, and 5
is the permeate discharge line, 6 is the lime milk introduction line,
7 is the olefin oxide take-out line, 8
9 indicates a reflux line, 9 indicates a bottom liquid discharge line, and 10 indicates a steam line.
Claims (1)
てオレフインオキサイドを製造するに際し、オレ
フインクロルヒドリンを逆浸透膜により５重量％
以上に濃縮した後、石灰乳によりけん化すること
を特徴とするオレフインオキサイドの製造方法。1. When saponifying an aqueous solution of olefin chlorohydrin to produce olefin oxide, 5% by weight of olefin chlorohydrin is added using a reverse osmosis membrane.
A method for producing olefin oxide, which comprises concentrating as described above and then saponifying it with milk of lime.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59052263A JPS60197665A (en) | 1984-03-21 | 1984-03-21 | Production of olefin oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59052263A JPS60197665A (en) | 1984-03-21 | 1984-03-21 | Production of olefin oxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60197665A JPS60197665A (en) | 1985-10-07 |
| JPH0461870B2 true JPH0461870B2 (en) | 1992-10-02 |
Family
ID=12909877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59052263A Granted JPS60197665A (en) | 1984-03-21 | 1984-03-21 | Production of olefin oxide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60197665A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1021417A (en) * | 1963-11-08 | 1966-03-02 | Huels Chemische Werke Ag | Process for preparing epichlorohydrin |
| JPS57174105A (en) * | 1981-04-17 | 1982-10-26 | Sumitomo Chem Co Ltd | Concentrating method for aqueous solution of organic substance |
-
1984
- 1984-03-21 JP JP59052263A patent/JPS60197665A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1021417A (en) * | 1963-11-08 | 1966-03-02 | Huels Chemische Werke Ag | Process for preparing epichlorohydrin |
| JPS57174105A (en) * | 1981-04-17 | 1982-10-26 | Sumitomo Chem Co Ltd | Concentrating method for aqueous solution of organic substance |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60197665A (en) | 1985-10-07 |
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