JPS63250329A - Stabilizing method - Google Patents
Stabilizing methodInfo
- Publication number
- JPS63250329A JPS63250329A JP8286587A JP8286587A JPS63250329A JP S63250329 A JPS63250329 A JP S63250329A JP 8286587 A JP8286587 A JP 8286587A JP 8286587 A JP8286587 A JP 8286587A JP S63250329 A JPS63250329 A JP S63250329A
- Authority
- JP
- Japan
- Prior art keywords
- monochloroxylene
- alpha
- stabilizer
- xylene
- hexamine
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 230000000087 stabilizing effect Effects 0.000 title claims description 4
- VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical group CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000008096 xylene Substances 0.000 claims abstract description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 9
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 9
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 239000003381 stabilizer Substances 0.000 claims abstract description 7
- 238000005660 chlorination reaction Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 238000003860 storage Methods 0.000 abstract description 3
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004677 Nylon Substances 0.000 abstract description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000004985 diamines Chemical class 0.000 abstract description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052742 iron Inorganic materials 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 229920001778 nylon Polymers 0.000 abstract description 2
- 239000012261 resinous substance Substances 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- 229910052725 zinc Inorganic materials 0.000 abstract description 2
- 239000011701 zinc Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 5
- -1 2°-dipyridine Chemical class 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical group CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UZPZYFDULMKDMB-UHFFFAOYSA-N 1,2-dichloro-3,4-dimethylbenzene Chemical group CC1=CC=C(Cl)C(Cl)=C1C UZPZYFDULMKDMB-UHFFFAOYSA-N 0.000 description 1
- WPZKRYLMVCPDJR-UHFFFAOYSA-N 1-(dichloromethyl)-2-methylbenzene Chemical group CC1=CC=CC=C1C(Cl)Cl WPZKRYLMVCPDJR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、α−モノクロロキシレンまたはα−モノクロ
ロキシレンを含有するキシレンの塩素化反応生成物の安
定化方法に関する。更に詳しくは、α−モノクロロキシ
レンまたはα−モノクロロキシレンを含有するキシレン
の塩素化反応生成物等に、安定剤としてヘキサミンを添
加する安定化方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for stabilizing α-monochloroxylene or a xylene chlorination reaction product containing α-monochloroxylene. More specifically, the present invention relates to a stabilization method in which hexamine is added as a stabilizer to α-monochloroxylene or a xylene chlorination reaction product containing α-monochloroxylene.
（従来の技術）
α−モノクロロキシレンは、合成樹脂の原料であるジグ
リコール、ナイロンの原料であるジアミン等に容易に変
換できるα、α′−ジクロロキシレンの中間原料として
有用である。しかし、α−モノクロロキシレンは放置す
れば次第に変質し、塩酸が発生し、樹脂状に変化しやす
い。この現象は、温度が高い場合、又は、鉄、亜鉛など
の金属が存在する場合に特に顕著であり、α−モノクロ
ロキシレンの製造、精製、貯蔵に問題ををしていた。(Prior Art) α-Monochloroxylene is useful as an intermediate raw material for α, α′-dichloroxylene, which can be easily converted into diglycol, which is a raw material for synthetic resins, diamine, which is a raw material for nylon, and the like. However, if α-monochloroxylene is left as it is, it will gradually change in quality, generate hydrochloric acid, and easily change into a resinous state. This phenomenon is particularly noticeable when the temperature is high or when metals such as iron and zinc are present, causing problems in the production, purification, and storage of α-monochloroxylene.
従来より本問題点を解決すべく、アミン類を添加する安
定化方法が検討されている０例えば、特開昭４８−６６
５７５号には、塩素化キシレンまたはトルエンを蒸留す
る方法において、トリエチルアミン、メチルジエチルア
ミン、トリプロピルアミン、トリブチルアミン、アニリ
ン、モノおよびジアルキルアニリン、ベンジルアミン、
２．２°−ジピリジン等のアミン、アミノカルボン酸の
アルカリ金属塩（ヒドロキシカルボン酸のアルカリ金属
塩または縮合リン酸のアルカリ金属塩の存在下において
行う事を特徴とする方法が提案されているが、上記の化
合物では効果的に充分ではなく、未だ有効な安走化方法
がないのが現状である。In order to solve this problem, stabilization methods by adding amines have been studied. For example, JP-A-48-66
No. 575 discloses a method for distilling chlorinated xylene or toluene, including triethylamine, methyldiethylamine, tripropylamine, tributylamine, aniline, mono- and dialkylaniline, benzylamine,
2. A method has been proposed in which the reaction is carried out in the presence of an amine such as 2°-dipyridine, an alkali metal salt of an aminocarboxylic acid (an alkali metal salt of a hydroxycarboxylic acid or an alkali metal salt of a condensed phosphoric acid). However, the above-mentioned compounds are not effective enough, and there is currently no effective method for achieving safety.
（発明が解決しようとする問題点）
本発明の目的は、上記問題点であるα−モノクロロキシ
レンの変質を防ぐ安定化方法を提供する事にある。(Problems to be Solved by the Invention) An object of the present invention is to provide a stabilization method that prevents the deterioration of α-monochloroxylene, which is the problem described above.
（問題点を解決する為の手段及び作用）本発明者らは、
上記目的を達成するため鋭意検討した結果、全く意外に
も、アミン類の中で特にヘキサミンが優れた安定性効果
を有する事を見出し、本発明を完成するに至った。(Means and effects for solving the problem) The present inventors
As a result of intensive studies to achieve the above object, it was completely unexpectedly discovered that among amines, hexamine in particular has an excellent stability effect, leading to the completion of the present invention.
即ち、本発明は、α−モノクロロキシレンまたはα−モ
ノクロロキシレンを含有するキシレンの塩素化反応生成
物に対し、安定剤としてヘキサミンを０．００１〜１０
．０重量％添加する事を特徴とする該物質の安定化方法
である。That is, in the present invention, 0.001 to 10% of hexamine is added as a stabilizer to α-monochloroxylene or a xylene chlorination reaction product containing α-monochloroxylene.
．． This is a method for stabilizing the substance, characterized by adding 0% by weight.
以下本発明を更に詳細に説明する。The present invention will be explained in more detail below.
本発明でいうα−モノクロロキシレンとは、α−モノク
ロローｐ−キシレン、α−モノクロローｍ−キシレンま
たはα−モノクロロー０−キシレンである。The α-monochloroxylene referred to in the present invention is α-monochloro p-xylene, α-monochloro m-xylene or α-monochloro 0-xylene.
α−モノクロロキシレンを含有するキシレン塩素化反応
生成物とは、α−モノクロロキシレンと、ｐ−キシレン
、ｍ−キシレンもしくは０−キシレンの側鎖メチル基が
塩素化されてなるα、α−ジクロロキシレン、α、α°
−ジクロロキシレン、もしくはα、α、α゛−トリクロ
ロキシレン及び更に塩素化されてなる高度の塩素化物等
の側鎖塩素化物と及び、キシレンと及び、キシレンもし
くはその側鎖塩素化物の芳香核が直接塩素化された核塩
素化物等とからなる混合物質、または、回分１留もしく
は連続蒸留により該混合物質を蒸留して得られる留出物
である。The xylene chlorination reaction product containing α-monochloroxylene refers to α-monochloroxylene and α,α-dichloroxylene obtained by chlorinating the side chain methyl group of p-xylene, m-xylene, or 0-xylene. , α, α°
- Side chain chlorinated products such as dichloroxylene or α, α, α゛-trichloroxylene and further chlorinated highly chlorinated products, and xylene and the aromatic nucleus of xylene or its side chain chlorinated product It is a mixed substance consisting of a chlorinated nuclear chloride, etc., or a distillate obtained by distilling the mixed substance by batchwise distillation or continuous distillation.
ヘキサミンの添加量は、α−モノクロロキシレンのさら
される条件に応じて変動しうるが、０．００１重量％以
上、１０重量％以下、更に好ましくはｏ、ｏｏｓ重量％
以上、５重量％以下である。The amount of hexamine added may vary depending on the conditions to which α-monochloroxylene is exposed, but is 0.001% by weight or more and 10% by weight or less, more preferably o, oos% by weight.
The content is 5% by weight or less.
０．００１重量％未満の場合は効果的に充分ではなく、
１４１％を超えても効果的には変わらない。If it is less than 0.001% by weight, it is not effectively sufficient,
Even if it exceeds 141%, there is no effective change.
本発明は通常は常圧で実施されるが、減圧条件下、加圧
条件下でも、効果はかわらない、また通常は２６０°Ｃ
以下の温度で実施される。Although the present invention is usually carried out at normal pressure, the effect remains the same even under reduced pressure or pressurized conditions, and it is usually carried out at 260°C.
It is carried out at the following temperatures:
また本発明の安定剤は、撹拌条件下でも、撹拌を行わな
くても充分に大きな効果を発揮する。Further, the stabilizer of the present invention exhibits a sufficiently large effect even under stirring conditions or without stirring.
（実施例） 以下実施例により本発明を説明する。(Example) The present invention will be explained below with reference to Examples.
実施例１〜９、比較例１〜４
１００ｍ１のガラス製フラスコに表１に示すα−モノク
ロロキシレン含有液５０ｇ及び添加物を入れ、表１に示
す条件で保温後、生成した塩酸を定量し、安定性の比較
を行った。結果を表１に示す。Examples 1 to 9, Comparative Examples 1 to 4 50 g of the α-monochloroxylene-containing liquid and additives shown in Table 1 were placed in a 100 ml glass flask, and after keeping warm under the conditions shown in Table 1, the generated hydrochloric acid was quantified, We compared the stability. The results are shown in Table 1.
実施例１０
１０１Ｏ０の５Ｏ５−３０４製のフラスコに、α−モノ
クロローｐ−キシレンを ５０ｇ入れ、ヘキサミンを０
．１重量％添加し、１００℃で４８時間保温後、実施例
１と同様に、生成した塩酸を定量したところ、５．３
Ｘ １０−’ モル／ｈｒであった。Example 10 Into a 10100 5O5-304 flask, 50g of α-monochloro-p-xylene was added, and 0.0 g of hexamine was added.
．． After adding 1% by weight and keeping it warm at 100°C for 48 hours, the amount of hydrochloric acid produced was quantified in the same manner as in Example 1, and it was found to be 5.3
X 10-' mol/hr.
比較例５
実施例１０と同様なフラスコに、α−モノクロローｐ−
キシレンを ５０ｇ入れ、添加剤を添加することなく、
１００°Ｃで０．５時間保温したところ、急激に塩酸を
発生し、樹脂状物質が生成した。塩酸発生量は０．２８
モル／ｈｒであった。Comparative Example 5 In a flask similar to Example 10, α-monochloro p-
Add 50g of xylene and add no additives.
When kept at 100°C for 0.5 hours, hydrochloric acid was rapidly generated and a resinous substance was formed. The amount of hydrochloric acid generated is 0.28
It was mol/hr.
（発明の効果）
本発明は、α−モノクロロキシレンの変質をほぼ完璧に
防ぐ優れた方法であり、α−モノクロロキシレンの製造
、精製、貯蔵に非常に有効であるとともに、ヘキサミン
は廉価であることから、コスト的にも有利である。(Effects of the Invention) The present invention is an excellent method for almost completely preventing the deterioration of α-monochloroxylene, and is very effective in the production, purification, and storage of α-monochloroxylene, and hexamine is inexpensive. Therefore, it is advantageous in terms of cost.
Claims (1)
シレンを含有するキシレンの塩素化反応生成物に対し、
安定剤としてヘキサミンを０．００１〜１０．０重量％
添加する事を特徴とする該物質の安定化方法。(1) For α-monochloroxylene or xylene chlorination reaction products containing α-monochloroxylene,
0.001-10.0% by weight of hexamine as a stabilizer
A method for stabilizing the substance, characterized by adding the substance.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8286587A JPS63250329A (en) | 1987-04-06 | 1987-04-06 | Stabilizing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8286587A JPS63250329A (en) | 1987-04-06 | 1987-04-06 | Stabilizing method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63250329A true JPS63250329A (en) | 1988-10-18 |
Family
ID=13786220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8286587A Pending JPS63250329A (en) | 1987-04-06 | 1987-04-06 | Stabilizing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63250329A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0347141A (en) * | 1989-04-07 | 1991-02-28 | Mitsui Toatsu Chem Inc | Preparation of aromatic compound having chlorinated side chain and stabilization thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4840734A (en) * | 1971-10-07 | 1973-06-15 | ||
| JPS4866575A (en) * | 1971-12-14 | 1973-09-12 | ||
| JPS4936215A (en) * | 1972-08-02 | 1974-04-04 | ||
| JPS5714540A (en) * | 1980-06-27 | 1982-01-25 | Ihara Chem Ind Co Ltd | Stabilization of aromatic compound bearing halogenated side chains |
-
1987
- 1987-04-06 JP JP8286587A patent/JPS63250329A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4840734A (en) * | 1971-10-07 | 1973-06-15 | ||
| JPS4866575A (en) * | 1971-12-14 | 1973-09-12 | ||
| JPS4936215A (en) * | 1972-08-02 | 1974-04-04 | ||
| JPS5714540A (en) * | 1980-06-27 | 1982-01-25 | Ihara Chem Ind Co Ltd | Stabilization of aromatic compound bearing halogenated side chains |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0347141A (en) * | 1989-04-07 | 1991-02-28 | Mitsui Toatsu Chem Inc | Preparation of aromatic compound having chlorinated side chain and stabilization thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2159441C (en) | Process for storage and transport of toluenediamine | |
| JPS63250329A (en) | Stabilizing method | |
| JP4537021B2 (en) | Preparation of colorless dibenzylamine | |
| US5136086A (en) | Preparation process of aliphatic isocyanate | |
| US2758131A (en) | Stabilization of unsaturated nitriles | |
| JP3122220B2 (en) | Method for producing p-dichlorobenzene | |
| US5118832A (en) | Process for the preparation of alkyl 3-chloroanthranilates | |
| US2784219A (en) | Stabilization of unsaturated nitriles | |
| US5080767A (en) | Process for preparing aromatic compounds having chlorinated side chains and method for stabilizing monochloro-side chain aromatic compounds | |
| JPH06135931A (en) | Maleimide composition improved in storage stability | |
| JPH0441441A (en) | Purification of cyclohexane, cyclohexene and benzene | |
| JPS59112947A (en) | Manufacture of 4-nitrodiphenylamine | |
| JPH07316130A (en) | Stabilization of n-vinylpyrrolidone | |
| FI75843B (en) | CATALYTIC COMPONENT FOR POLYMERING CATALYST AV ALFAOLEFINER OCH FOERFARANDE FOER DERAS FRAMSTAELLNING. | |
| US2850522A (en) | Stabilization of unsaturated nitriles | |
| US5087714A (en) | Method of preventing discoloration of vinylacetoxysilanes | |
| US3873589A (en) | Isocyanate purification process | |
| US2912437A (en) | Process for the production of aromatic homocyclic or heterocyclic di-and polycarboxylic acids | |
| JPH09316042A (en) | Stabilization of n-vinylcarboxylic acid amide | |
| US2758130A (en) | Stabilization of unsaturated nitriles | |
| JPS63250330A (en) | Stabilizing method | |
| JPS5965046A (en) | Stabilization of dichlorobutene | |
| AU604695B2 (en) | Synthesis of high purity 5-chloroisophthaloyl chloride | |
| US3114763A (en) | Organo-substituted monofluoromalononitriles and their preparation | |
| JP3584611B2 (en) | Method for preserving and purifying N-vinylcarboxylic acid amide |