JPS5962561A - Storage or transportation of aromatic urethane - Google Patents
Storage or transportation of aromatic urethaneInfo
- Publication number
- JPS5962561A JPS5962561A JP17422982A JP17422982A JPS5962561A JP S5962561 A JPS5962561 A JP S5962561A JP 17422982 A JP17422982 A JP 17422982A JP 17422982 A JP17422982 A JP 17422982A JP S5962561 A JPS5962561 A JP S5962561A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic urethane
- aromatic
- hydroxyl group
- organic compound
- urethane
- 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.)
- Pending
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 44
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 150000002894 organic compounds Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- -1 aromatic urethanes Chemical class 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 11
- 238000005979 thermal decomposition reaction Methods 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 8
- 241000406799 Deto Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 210000000940 dendritic epidermal T lymphocyte Anatomy 0.000 description 3
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 3
- RQHLPJYRTSWDRG-UHFFFAOYSA-N ethyl n-[(ethoxycarbonylamino)-phenylmethyl]carbamate Chemical compound CCOC(=O)NC(NC(=O)OCC)C1=CC=CC=C1 RQHLPJYRTSWDRG-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- YPAYDQZVQXAXHM-UHFFFAOYSA-N ethyl n-[2-chloro-6-(ethoxycarbonylamino)phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(Cl)=C1NC(=O)OCC YPAYDQZVQXAXHM-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は芳香族ウレタンの貯蔵又は輸送方法に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for storing or transporting aromatic urethanes.
近年、例えば、ポリウレタンの原料であるトリレンジイ
ソシアネートなどの芳香族イソシアネートを製造する方
法として、芳香族ニトロ化合物を触媒の存在下、−酸化
炭素及び水酸基を有する有機化合物と反応させて芳香族
ウレタン′ｆ：製造し、次いで、これを熱分解すること
により対応する芳香族イソシアネートを製造する方法が
Ｓ案されている。この方法において、芳香ｔ〜ルウレタ
ン熱分解は通常、例えば、／ｋＯ〜１１００′ｃに加熱
された不活性溶媒中に、芳香族ウレタンを供給して熱分
解を行ない、生成した芳香族インシアネートの蒸気を回
収することにより行なわれるり（例えば、特開昭ｊ弘−
ｇ ｇｌ、２．２２号公報参照）。この工程にて芳香族
ウレタンを連続的に供給する場合には、芳香族ウレタン
は常温では同体であり、工業的には粉体等固体の定量供
給は操作的に−１しいので、通常、芳香族ウレタンを溶
融し、この溶融液を供給する方法が考えられる。In recent years, for example, as a method for producing aromatic isocyanates such as tolylene diisocyanate, which is a raw material for polyurethane, aromatic nitro compounds are reacted with organic compounds having carbon oxide and hydroxyl groups in the presence of a catalyst to produce aromatic urethanes. Plan S has been proposed to produce a corresponding aromatic isocyanate by producing f: and then thermally decomposing it. In this method, aromatic urethane thermal decomposition is usually carried out by supplying aromatic urethane into an inert solvent heated to /kO ~ 1100'C, and then thermally decomposing the aromatic incyanate. This can be done by recovering steam (for example, as described in
g gl, see Publication No. 2.22). When aromatic urethane is continuously supplied in this process, aromatic urethane is isomerized at room temperature, and industrially, quantitative supply of solids such as powder is difficult to operate, so normally aromatic urethane is A possible method is to melt the group urethane and supply this melt.
しかしながら、芳香族ウレタンを溶融液として供給する
場合には、通常、予め溶融槽にて芳４族ウレタンを溶融
させたのち、熱分解工程へ供給することになるが、との
場合、芳香族ウレタンは相当時間、溶融槽内に滞留し溶
融保持されることとなる。芳香族ウレタンは溶融湿度付
近以上に加熱すると、芳香族ウレタンの一部が分解し、
魅に、これが構造不明の化合物に変化する傾向がある。However, when aromatic urethane is supplied as a melt, the aromatic urethane is usually melted in advance in a melting tank and then supplied to the thermal decomposition process. remains in the melting tank and remains molten for a considerable period of time. When aromatic urethane is heated above the melting humidity, part of the aromatic urethane decomposes,
Interestingly, this tends to transform into compounds of unknown structure.
そのため、この芳香族ウレタンを用いて熱分解反応を行
かった地合には、熱分解工程での芳香族インシアネート
の収率が低下するばかりか、溶％１１時に生成した構造
不明の化合物が熱分解工程でハルツ化し、そのため、ハ
ルツ処理が面倒となる欠点がある。Therefore, when a thermal decomposition reaction is carried out using this aromatic urethane, not only does the yield of aromatic incyanate in the thermal decomposition process decrease, but also a compound of unknown structure formed at a melting point of 11% is generated. It has the disadvantage that it becomes hartz during the pyrolysis process, which makes hartz treatment troublesome.
本発明者等は上記実情に鑑み、芳香族ウレタンを加熱溶
融した場合の安定性を改善する方法につき種々検討した
結果、ある４−！Ｆ定の化合物を存在させることにより
本発明の目的が達成されることを見い出し本発明を完成
した。In view of the above circumstances, the inventors of the present invention have conducted various studies on methods for improving the stability of aromatic urethane when melted by heating. The present invention was completed by discovering that the object of the present invention can be achieved by the presence of a compound having a constant F.
すなわち、本発明の要旨は、芳香族ウレタンの水酸基を
有する有機化合物を存在させることを特徴とする芳香族
ウレタンの貯蔵又は輸送方法に存する。That is, the gist of the present invention resides in a method for storing or transporting aromatic urethane, which is characterized in that an organic compound having a hydroxyl group of aromatic urethane is present.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
一本発明で対象とする芳香族ウレタンとしては、通常、
７価乃至３価の芳香族イソシアネートと７価乃至９価の
脂肪族、芳香族又は脂環族の水酸基を有する化合物とを
反応させて得られるつｖタン化合物であり、例えば、ジ
メチルトルエト、ジエチル−クロルベンゼン−ジカルバ
メート、エテルナフタレン−カルバメート、ジェチルア
ントラセンージヵルバメー）、メｆし７−シフエニルー
ジエテルウレタン、メチレン−ジフェニル−ジフェニル
ウレタンなどが挙ケラレ、なかでも、トリレンジイソシ
アネート又はメテレンビスフェニルイソシアネートト／
価の水酸基を有する化合物よりなる芳香族ウレタンが好
ましい。Aromatic urethanes targeted by the present invention usually include:
A tan compound obtained by reacting a heptavalent to trivalent aromatic isocyanate with a compound having a heptavalent to nonavalent aliphatic, aromatic, or alicyclic hydroxyl group, such as dimethyltoluene, Diethyl-chlorobenzene-dicarbamate, eternaphthalene-carbamate, diethyl-anthracene-dicarbamate), mef-7-siphenylene-dietherurethane, methylene-diphenyl-diphenylurethane, etc. Isocyanate or methylene bisphenyl isocyanate/
An aromatic urethane made of a compound having a valent hydroxyl group is preferred.
本発明では上述のような芳香族ウレタンを溶融状傳で４
闘又は輸送する際に、水ｒ９基を有する有機化合物を存
在させることを要件とするものである。すなわち、芳香
族ウレタンは固体状態では安定であるものの、融点付近
場−ヒの温度に加熱した場合には、熱安定性が低下する
が、これに水酸基を有する有機化合物全存在させること
により、この熱安定性が改善されるのである。通常、芳
香族ウレタンの融点はその枦鳳により異々るが、例えば
、ジエチルトルエン−ジカルバメートの場合は、約／２
Ｑ〜／７０Ｃである。In the present invention, the above-mentioned aromatic urethane is
It is a requirement that an organic compound having a water r9 group be present during fighting or transportation. In other words, although aromatic urethane is stable in the solid state, its thermal stability decreases when heated to a temperature close to its melting point. Thermal stability is improved. Usually, the melting point of aromatic urethane varies depending on its temperature, but for example, in the case of diethyltoluene-dicarbamate, it is about /2
Q~/70C.
本発明で用いる水酸基を有する化合物としては、通常、
脂肪族、芳香族又は脂環ｊ疾の７価乃至弘価のアルコー
ル又はフェノールが挙げられ、具体的には例えば、メタ
ノール、エタノール、プロパツール、ブタノール、ニー
エチルヘキサ／ −ル、 オクタツール、エチレンクリ
コール、／、４’−ブタンジオール、グリセリン、フェ
ノール、コツ６−ジーｔｅｒｔ−ブチル−ｔ−メチルフ
ェノール、ドデシルフェノール、カテコール、ビスフェ
ノールＡ１ ビスフェノールＳ１ベンジルアルコール、
シクロヘキサノール、メチルシクロヘキザノールなどが
用いられる。このアルコール又はフェノールは例えば、
ノ・ロゲン原子、スルホン酸基、シアン基、ニトロ基、
アルコキシ基などの芳香夜ウレタン及びイソシアネート
に対して不活＝ｌ′Ａニな置換基で俗換されていてもよ
い。これらの化合物の中で、特に、炭素数／〜５の脂肪
族７価アルコール、又は炭素数ｔ〜４０の７価フェノー
ル類を用いるのが好ましく、また、対象とする芳香族ウ
レタンを形成する水酸基を有する有（浅化合物と同一の
化合物を用いるのが好ましい。The compound having a hydroxyl group used in the present invention is usually
Examples include aliphatic, aromatic, or alicyclic heptavalent or polyhydric alcohols or phenols, such as methanol, ethanol, propatool, butanol, ethylhexyl, octatool, and ethylene. glycol, 4'-butanediol, glycerin, phenol, 6-di-tert-butyl-t-methylphenol, dodecylphenol, catechol, bisphenol A1 bisphenol S1 benzyl alcohol,
Cyclohexanol, methylcyclohexanol, etc. are used. This alcohol or phenol can be e.g.
Norogen atom, sulfonic acid group, cyan group, nitro group,
The aromatic urethanes and isocyanates may be substituted with inert substituents such as alkoxy groups. Among these compounds, it is particularly preferable to use aliphatic heptahydric alcohols having 5 carbon atoms or heptahydric phenols having t to 40 carbon atoms, and hydroxyl groups forming the target aromatic urethane. It is preferable to use the same compound as the shallow compound.
水酸基を有する有機化合物の存在量は芳香族ウレタンに
対し、０．０７モル倍以上、好ましくは０．７モル倍以
上、更に好ましくは０．３〜１０モル倍である。この存
在量かあ′！！シ少ない場合には、芳香族ウレタンの熱
安定性を十分に改善することはできず、丑だ、あまり多
い場合には、効果に変りはないが後工程での水酸基を有
する有機化合物の回収が面倒とがるので好寸しくない。The amount of the organic compound having a hydroxyl group is 0.07 mole or more, preferably 0.7 mole or more, and more preferably 0.3 to 10 mole times, relative to the aromatic urethane. This amount exists! ! If the amount is too small, the thermal stability of the aromatic urethane cannot be improved sufficiently, and if it is too large, the effect will be the same, but the recovery of organic compounds with hydroxyl groups in the subsequent process will be difficult. It's a hassle, so it's not a good fit.
本発明では′１８融状態の芳香族ウレタン中に所定量の
水酸基を有する有機化合物を存在させる必要がある一ｈ
−１芳香塵芳香タウレタン基を有する有機化合Ｉ吻との
）μ択の仕方によっては、水酸基を有する有機化合物の
沸点が芳香族ウレタンの重点よりも佃い場合がある。例
え―、芳香族ウレタンとしてジエチルトルエン−ジカル
バメートを用い、一方、水酸基を有する有機化合物とし
てエタノールを用いる場合には、ジエチルトルエン−ジ
カルバメートの昂中府は約／ユ０〜／７０Ｃであるのに
対し、エタノールの沸点は７ｇ口と低い。このような場
合には、本発明では芳香族ウレタンの貯蔵又は輸送を水
酸基を有する有機化合物が液相を保持できる加圧下で実
施することが必要である。In the present invention, it is necessary to have a predetermined amount of an organic compound having a hydroxyl group present in the aromatic urethane in the molten state.
-1 Aromatic dust An organic compound having an aromatic taurethane group Depending on the selection method, the boiling point of the organic compound having a hydroxyl group may be lower than that of the aromatic urethane group. For example, when diethyltoluene-dicarbamate is used as the aromatic urethane and ethanol is used as the organic compound having a hydroxyl group, the concentration of diethyltoluene-dicarbamate is approximately 0 to 70C. On the other hand, the boiling point of ethanol is as low as 7 grams. In such a case, in the present invention, it is necessary to store or transport the aromatic urethane under pressure that allows the organic compound having a hydroxyl group to maintain a liquid phase.
本発明を適用Ｉ−得る工程としては、例えば、芳香族ウ
レタンの溶融槽及び該溶融槽から熱分解槽に至る間の貯
槽又は輸送配管などである。The process to which the present invention is applied includes, for example, an aromatic urethane melting tank and a storage tank or transportation piping between the melting tank and the thermal decomposition tank.
べた、芳香族ウレタンへの水酸基を有する有機化合物の
添加は通常、芳香族ウレタンの溶融前に所定量の水酸基
を有する化合物を添加することにより行なわれる。Generally, the addition of an organic compound having a hydroxyl group to an aromatic urethane is carried out by adding a predetermined amount of the compound having a hydroxyl group before melting the aromatic urethane.
本発明の方法により安定化された芳香族ウレタンを用い
て熱分解する場合には、通常、熱分解槽内に仕込壕れた
所定温度の不活性溶媒中に、不活性溶媒を含有する溶融
状態の芳香族ウレタンを連続的に供給することにより行
々われる。In the case of thermal decomposition using the aromatic urethane stabilized by the method of the present invention, a molten state containing an inert solvent is usually placed in an inert solvent at a predetermined temperature charged in a thermal decomposition tank. This is done by continuously supplying aromatic urethane.
そして、例えば、一つ・の実施態様によれば、分解で生
成した芳香族インシアネート及び水酸基ケ有する有機化
合物の蒸気を上部の気相部より回収し、これを所定温度
で順次、凝縮することにより芳香族イソシアネートを単
離する。一方、芳香族ウレタンとともに供給された水酸
基を有する有機化合物Ｆｉ、熱分解によシ生成した水酸
基を有する有機化合物とともに回収することができる。For example, according to one embodiment, the aromatic incyanate produced by decomposition and the vapor of the organic compound having a hydroxyl group are recovered from the upper gas phase and sequentially condensed at a predetermined temperature. The aromatic isocyanate is isolated by. On the other hand, it can be recovered together with the organic compound Fi having a hydroxyl group supplied with the aromatic urethane and the organic compound having a hydroxyl group produced by thermal decomposition.
熱分解処理は通常、／左θ〜ｌ／、ＯＯＣの温度で常圧
〜Ｏ１θ／ ｔｏｒｒの減圧下で実施されるっ以上、本
発明によれば、芳香族ウレタンを特に、溶融状態で保持
して貯蔵又は輸送する際の芳香族ウレタンの分解及び構
造不明物への変化を抑制することができるので、熱分解
工程におけ為芳香族イソシアネートの回収率を同士させ
ることができ、また、熱分解時に生成するハルツ骨ヲ減
少することもできる。Thermal decomposition treatment is usually carried out at a temperature of /left θ~l/, OOC and under a reduced pressure of normal pressure to O1θ/torr.According to the present invention, the aromatic urethane is particularly maintained in a molten state. It is possible to suppress the decomposition of aromatic urethane and its change into substances of unknown structure during storage or transportation, so the recovery rate of aromatic isocyanate in the thermal decomposition process can be made equal to that of the aromatic isocyanate. It can also reduce the amount of Harz bone that is produced.
次に、本発明を実施例にょシ更に詳細に説明するが、本
発明はその要旨をル曳乏−ない限り以下の実施例に限定
されるものでけ々い。Next, the present invention will be described in more detail with reference to Examples, but the present invention is limited to the following Examples unless the gist thereof is omitted.
実施例／〜グ及び比較例／
温１ノ＞−訓節器を有する攪拌機付密閉容器に、ジエチ
ルトルエンージヵルバメ−１−（，２，ＩＩ−一体ｇｏ
部と、２ 、４一体２０部の混合物）（以下、ＤＥＴＣ
と言う）りｏｙを仕込み、これに第１表に示す割合のエ
タノール（試薬７級）す・加工、均一混合したのち、気
相部を窒素ガスで置換し、１０ｋｙ／ｃｙｆｔの加圧と
し、次いで、／グｏｃに昇温し混合物を溶融させ、同温
度で攪拌下、３コ時間、加熱保持することにより熱安定
性テストを行々つた。Examples / ~ and Comparative Examples / Diethyltoluene-dicarbamate-1-(,2,II-integrated go
(hereinafter referred to as DETC)
After processing and uniformly mixing ethanol (reagent grade 7) in the proportion shown in Table 1, the gas phase was replaced with nitrogen gas, and the pressure was increased to 10 ky/cyft. Next, the mixture was melted by raising the temperature to 0.5 °C, and a thermal stability test was conducted by heating and maintaining the mixture at the same temperature for 3 hours while stirring.
このテスト後、密閉容器を放圧し、内容物を室温捷で冷
却したのち、この内容物を液体クロマトグラフィーによ
り分析し、ＤＥＴＣ！の減少率を求めるとともに、減少
したＤＥＴＯよシ生成したモノ又はジインシアネートの
量及び構造不明物の債を対応する仕込みＤＥＴＯに対す
るモル係として求め、その結果を第１表に示す。After this test, the airtight container was depressurized and the contents were cooled at room temperature.The contents were analyzed by liquid chromatography and DETC! In addition to determining the reduction rate of DETO, the amount of mono- or di-incyanate produced by the decreased DETO and the amount of unidentified substances were determined as molar ratios to the corresponding charged DETO, and the results are shown in Table 1.
第１表
実施例Ｓ−６
実施例／の方法において、エタノールの代りに、第２表
に示す水や基を有する有機化合物をＤＥＴＣに対し、２
モル倍添加し、実施例／と全く同様のテストを行なった
結果を第２表に示す。Table 1 Example S-6 In the method of Example//, instead of ethanol, an organic compound having water or a group shown in Table 2 was added to DETC for 2
Table 2 shows the results of a test conducted in exactly the same manner as in Example 2 with the addition of twice the molar amount.
第２表 出 願 人 三菱化成工業株式会社 代 理 人 弁理士 長谷用 −（ほか７名）Table 2 Sender: Mitsubishi Chemical Industries, Ltd. Representative Patent Attorney Hase - (7 others)
Claims (3)
貯蔵又ｄ、輸送する際に、芳香族ウレタンに対して、ρ
、θ１モル倍以−ヒの水酸基を有する有機化合物を存在
させることを層像とする芳香族ウレタンの貯蔵又は輸送
方法。(1) Melting aromatic urethane: When storing or transporting aromatic urethane by heating it,
, a method for storing or transporting aromatic urethane in which an organic compound having a hydroxyl group of at least 1 mole of θ is present.
族アルコールであることを特徴とする特許請求の範囲第
（１）項記載の方法。(2) The method according to claim (1), wherein the organic compound having a hydroxyl group is a fatty auxiliary alcohol having a carbon number of /~S.
形成する水酸基を有する有機化合物と同一化合物である
ことを特徴とする特許請求の範囲第（］）項又は第（２
）項記載の方法。(3) The organic compound having a hydroxyl group is the same as the organic compound having a hydroxyl group that forms the aromatic urethane.
) Method described in section.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17422982A JPS5962561A (en) | 1982-10-04 | 1982-10-04 | Storage or transportation of aromatic urethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17422982A JPS5962561A (en) | 1982-10-04 | 1982-10-04 | Storage or transportation of aromatic urethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5962561A true JPS5962561A (en) | 1984-04-10 |
Family
ID=15974976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17422982A Pending JPS5962561A (en) | 1982-10-04 | 1982-10-04 | Storage or transportation of aromatic urethane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5962561A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150259279A1 (en) * | 2007-03-30 | 2015-09-17 | Asahi Kasei Chemicals Corporation | Isocyanate Production Process Using Composition Containing Carbamic Acid Ester and Aromatic Hydroxy Compound, and Composition for Transfer and Storage of Carbamic Acid Ester |
-
1982
- 1982-10-04 JP JP17422982A patent/JPS5962561A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150259279A1 (en) * | 2007-03-30 | 2015-09-17 | Asahi Kasei Chemicals Corporation | Isocyanate Production Process Using Composition Containing Carbamic Acid Ester and Aromatic Hydroxy Compound, and Composition for Transfer and Storage of Carbamic Acid Ester |
| US9637445B2 (en) * | 2007-03-30 | 2017-05-02 | Asahi Kasei Chemicals Corporation | Isocyanate production process using composition containing carbamic acid ester and aromatic hydroxy compound, and composition for transfer and storage of carbamic acid ester |
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