JPS63284223A - Manufacture of oxyalkylene ether - Google Patents
Manufacture of oxyalkylene etherInfo
- Publication number
- JPS63284223A JPS63284223A JP11928987A JP11928987A JPS63284223A JP S63284223 A JPS63284223 A JP S63284223A JP 11928987 A JP11928987 A JP 11928987A JP 11928987 A JP11928987 A JP 11928987A JP S63284223 A JPS63284223 A JP S63284223A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- adduct
- alkylene oxide
- oxyalkylene
- alkaline
- 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
- -1 oxyalkylene ether Chemical compound 0.000 title claims abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 13
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims abstract 3
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 125000005702 oxyalkylene group Chemical group 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- 238000007259 addition reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はオキシアルキレンエーテルの製造法さらに詳し
くはハロゲン化ジフェノール類のオキシアルキレンエー
テルの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for producing oxyalkylene ethers, and more particularly to a method for producing oxyalkylene ethers of halogenated diphenols.
従来ハロゲン化ジフェノール類のオキシアルキレンエー
テルの製造法としてはテトラブロモビスフェノールＡに
アルカリ触媒を使用してアルキレンオキナートを付加さ
せる方法がある。Conventional methods for producing oxyalkylene ethers of halogenated diphenols include adding alkylene ochinate to tetrabromobisphenol A using an alkali catalyst.
しかしこの方法では淡色のものが得られない。 However, this method does not produce light colors.
Ｃ問題点を解決するための手段〕
本発明者らは淡色なハロゲン化ジフェノール類のオキシ
アルキレンエーテルの得られる製造法について鋭意検討
を行った結果、本発明に到達した。Means for Solving Problem C] The present inventors conducted intensive studies on a method for producing a light-colored oxyalkylene ether of halogenated diphenols, and as a result, they arrived at the present invention.
すなわち本発明はハロゲン化ジフェノール類に無触媒で
アルキレンオキシドを付加させて得られる生成物に、ア
ルカリ性触媒又は酸性触媒の存在下アルキレンオキシド
を付加させることにより淡色なハロゲン化ジフェノール
類のオキシアルキレンエーテルを得ることを特徴とする
オキシアルキレンエーテルの製造法である。In other words, the present invention produces light-colored oxyalkylenes of halogenated diphenols by adding alkylene oxide to halogenated diphenols in the presence of an alkaline or acidic catalyst to the product obtained by adding alkylene oxide to halogenated diphenols without a catalyst. This is a method for producing oxyalkylene ether, which is characterized by obtaining an ether.
ハロゲン化ジフェノール類に無触媒でフルキレンオキシ
ドＣ以下ＡＯと略す）を付加させて得られる生成物にお
いて、ハロゲン化ジフェノール類としては一般式
％式％
（式中％−Ａはアルキレン基、ＳＯ，、硫黄原子、又は
酸素原子、Ｘはハロゲン原子、ｍｎは１〜４の整数であ
る。）で示される化合物があげられる。In the product obtained by adding fullkylene oxide C (hereinafter abbreviated as AO) to halogenated diphenols without a catalyst, the halogenated diphenols have the general formula % formula % (where %-A is an alkylene group, SO, sulfur atom, or oxygen atom, X is a halogen atom, mn is an integer from 1 to 4).
一般式（１）において、Ａのアルキレン基としてはＣＨ
３
Ｘのハロゲン原子としては塩素原子、臭素原子、弗素原
子などがあげられ、好ましくは塩素原子および臭素原子
、特に好ましくは臭素原子である。In general formula (1), the alkylene group of A is CH
Examples of the halogen atom for 3
一般式（１）で示される化合物の具体例としては、これ
らの内好ましいのはＴＥＡである。As a specific example of the compound represented by the general formula (1), TEA is preferred.
ＡＯとしては炭素数２〜４のＡＯ及びその置換体があげ
られる。炭素数２〜４のＡＯとしてはエチレンオキシド
（以下ＥＯと略す）、プロピレンなど）およびハロゲン
置換体（エピクロルヒドリンなど）があげられる。ＡＯ
は２種以上用いても良く、２種以上の場合、ランダム結
合、ブロック結合およびこれらの両方の結合を形成して
も良い。Examples of AO include AO having 2 to 4 carbon atoms and substituted products thereof. Examples of AO having 2 to 4 carbon atoms include ethylene oxide (hereinafter abbreviated as EO), propylene, etc.) and halogen-substituted products (epichlorohydrin, etc.). A.O.
Two or more types may be used, and when two or more types are used, a random combination, a block combination, or both of these combinations may be formed.
ＡＯのうち好ましいものはＥＯおよびＰＯである。Among AOs, preferred are EO and PO.
ハロゲン化ジフェノール類にＡＯを無触媒で付加させる
に際し、付加モル数は通常１〜４好ましに通常、加圧下
で行われる。また、通常、溶媒の不存在下で行われる。When adding AO to halogenated diphenols without a catalyst, the number of moles added is usually 1 to 4, preferably under pressure. Moreover, it is usually carried out in the absence of a solvent.
付加（反応）温度は通常１００〜２００℃、好ましくは
１４０〜１８０℃であり、付加（反応）時間はアルカリ
性触媒を使用した場合と同様、例えば８〜１０時間であ
る。終点はガスクロでチェック出来る。The addition (reaction) temperature is usually 100 to 200°C, preferably 140 to 180°C, and the addition (reaction) time is, for example, 8 to 10 hours, as in the case where an alkaline catalyst is used. The end point can be checked with gas chromatography.
この生成物（１）のＯＨＶは通常１００〜５００ 、好
ましくは１５０〜２００である。色相（ハーゼン法）は
通常５０〜６００である。The OHV of this product (1) is usually 100-500, preferably 150-200. The hue (Hazen method) is usually 50 to 600.
仁の無触媒でのアルキレンオキシド付加物は商品化が可
能であり、無触媒のため後処理の必要がなく、コスト面
で有用である。Jin's catalyst-free alkylene oxide adduct can be commercialized, and since it is catalyst-free, it does not require post-treatment, and is useful in terms of cost.
この生成物にアルカリ性又は酸性触媒の存在下。This product in the presence of an alkaline or acidic catalyst.
ＡＯを付加させるに際しＡＯとしてｔｉ前記のＡＯと同
様なものがあげられ、好ましいものも同様である。When adding AO, AO may be the same as the above-mentioned AO, and preferred ones are also the same.
アルカリ性触媒としては、アルカリ触媒たとえばアルカ
リ金属水酸化物（ＫｏＨ，ＮａｏＨなど）およびアミン
触媒（トリメチルアミンなど）があげられる。Examples of alkaline catalysts include alkali catalysts such as alkali metal hydroxides (KoH, NaoH, etc.) and amine catalysts (trimethylamine, etc.).
酸性触媒としてはルイス酸（四塩化錫など）、ＢＦ、
（ＢＦ、エーテラートなど）などがあげられる。As acidic catalysts, Lewis acids (such as tin tetrachloride), BF,
(BF, Aetherate, etc.).
触媒のうちで好ましいのはアルカリ性触媒であり、とく
に好ましいのは、ＫＯＨ，Ｎａ０ｆｉおよびトリメチル
アミンである。Preferred among the catalysts are alkaline catalysts, particularly preferred are KOH, Na0fi and trimethylamine.
触媒の鼠は生成物（１） １モルに対し通常０．００１
〜１モル、好ましくは０．０１〜０．５モルである。The catalyst is usually 0.001 per mole of product (1).
-1 mol, preferably 0.01-0.5 mol.
ＡＯの付加モル数は全付加モル数が通常？１００゜好ま
しくは８〜２０になるモル数である。Is the number of added moles of AO normally the total number of added moles? The number of moles is preferably 8 to 20.
ＡＯの付加は通常、加圧下で行われる。反応温度は通常
６０〜２００℃、好ましくは８０〜１４０℃である。反
応時間は付加モル数によって異なるが通常８〜１０時間
である。Addition of AO is usually carried out under pressure. The reaction temperature is usually 60-200°C, preferably 80-140°C. The reaction time varies depending on the number of moles added, but is usually 8 to 10 hours.
後処理は中和あるいは酸性白土処理を行う。Post-treatment involves neutralization or acid clay treatment.
反応の終点はＯＨＶで行うことが出来る。The end point of the reaction can be carried out in OHV.
得られたオキシアルキレンエーテルのＯＨＶは通常８０
〜８００．好ましくは５０〜２００である。色相（ハー
ゼン）は通常６００以下である。The OHV of the obtained oxyalkylene ether is usually 80.
~800. Preferably it is 50-200. The hue (Hazen) is usually 600 or less.
以下、実施例により本発明をさらに説明するが、本発明
はこれらの実施例に限定されるものではないＯ
実施例１
１１オ一トクレーブ反応機にＴ Ｂ Ａ １００．９（
０，１８モル）を仕込み、容器内を窒素で充分置換した
。Hereinafter, the present invention will be further explained with reference to examples, but the present invention is not limited to these examples.
0.18 mol) and the inside of the container was sufficiently purged with nitrogen.
攪拌下、１８０〜１９０℃でＥ Ｏ１６，６１１／８
（０，８８モル／８）を滴下反応させ、その後１４０〜
１５０℃まで冷却後、残量のＥＯを滴下した。滴下終了
後、同温度で２時間熟成した。その後１００〜１１０“
Ｃに冷却し、触媒としてＫＯＨを（１２，９（０，００
４モル）添加し、再び窒素で置換を行った。その後１２
０〜１８０℃でＥ ０９７．１ｇ（２，２モル）を約６
時間を要して滴下反応あせた。滴下終了後同温度で２時
間熟成した。E O16,611/8 at 180-190°C under stirring
(0.88 mol/8) was reacted dropwise, and then 140~
After cooling to 150°C, the remaining amount of EO was added dropwise. After the dropwise addition was completed, the mixture was aged for 2 hours at the same temperature. Then 100~110"
C and KOH as a catalyst (12,9(0,00
4 mol) was added, and the substitution was again performed with nitrogen. then 12
E 097.1g (2.2 mol) at 0-180℃
It took some time for the dropping reaction to slow down. After completion of the dropwise addition, the mixture was aged for 2 hours at the same temperature.
その後９０℃迄冷却し、氷酢酸０．１５．９を添加し触
媒を中和した。その後容器に取出し２１１．５／ｉ（収
率＝９８．８９６）のＴＢＡのオキシアルキレンエーテ
ルを得た。この生成物は淡赤黄色の液状物でＯＨＶは９
９．１で色相（ハーゼン）は２００であった。Thereafter, the mixture was cooled to 90° C., and 0.15.9 g of glacial acetic acid was added to neutralize the catalyst. Thereafter, it was taken out into a container to obtain an oxyalkylene ether of TBA of 211.5/i (yield=98.896). This product is a pale reddish-yellow liquid with an OHV of 9.
It was 9.1 and the hue (Hazen) was 200.
実施例２
実施例１と同様の方法で得られる無触媒のＴＢＡのＥＯ
付加物を使用し、この付加物に触媒として要して滴下反
応させた。滴下終了後同温度で８時間熟成を行った。氷
酢酸０．４ｇで触媒を中和後容器に取付し２１９，９（
９８，８％）のＴＢＡのオキシアルキレンエーテルを得
た。この生成物は淡黄色の液状で０）ＩＶは１０１であ
り色相（八−ゼン）は１１０であった。Example 2 Uncatalyzed TBA EO obtained by the same method as Example 1
The adduct was used as a catalyst and the reaction was carried out dropwise. After completion of the dropwise addition, aging was carried out at the same temperature for 8 hours. After neutralizing the catalyst with 0.4 g of glacial acetic acid, attach it to a container and add 219,9 (
An oxyalkylene ether of TBA (98.8%) was obtained. This product was a pale yellow liquid with an 0)IV of 101 and a hue (8-zene) of 110.
比較例１
実施例１の方法において無触媒で反応する代りに触媒と
してＫ ＯＨＯ，２９（０，００８６モル）を使用し連
続的にＥＯを付加する以外は実施例１と同じ方法で行っ
た。この生成物は褐色の液状物であり色相（ガードナー
）は１８（でめった。Comparative Example 1 A reaction was carried out in the same manner as in Example 1, except that instead of reacting without a catalyst in the method of Example 1, K OHO,29 (0,0086 mol) was used as a catalyst and EO was continuously added. The product was a brown liquid with a hue (Gardner) of 18.
比較例２
実施例１の方法において、無触媒で反応する代りに触媒
としてトリエチルアミン０．８．９ （０，００５モル
）を使用し連続的にＥＯを付加する以外は実施例１と同
じ方法で行った。このものはＥＯ２２ｐ（０，５モル）
付加した付近より反応が進まなくなった。Comparative Example 2 The same method as in Example 1 was used except that instead of reacting without a catalyst, 0.8.9 (0,005 mol) of triethylamine was used as a catalyst and EO was added continuously. went. This stuff is EO22p (0.5 mol)
The reaction stopped progressing near the area where it was added.
本発明は下記の効果を奏する。 The present invention has the following effects.
（１）本発明の方法は従来のアルカリ触媒を使う方法ニ
くうべ着色の少ないハロゲン化ジフェノール類のオキシ
アルキレンエーテルが得られる。(1) The method of the present invention uses a conventional alkali catalyst. Oxyalkylene ethers of halogenated diphenols with little coloring can be obtained.
（２）本発明の方法は従来、２モル程度の付加物しか得
られなかったトリエチルアミンとか％Ｎ、Ｎ−ジヒドロ
キシエチルーＮ−ｎ−アルキルアミンとか、有機カルボ
ン酸のアルカリ塩とかを触媒として使う方法（たとえは
特公昭６０−４９６２１号および特公昭６０−５５７８
号各公報）にくらべ、ハロゲン化ジフェノール類のオキ
シアルキレンエーテルの低付加物のみならず高付加物が
得られる。高付加物は粘度が低く、ハンドリング性が良
好である。(2) The method of the present invention uses triethylamine, %N, N-dihydroxyethyl-N-n-alkylamine, and alkali salts of organic carboxylic acids as catalysts, from which only about 2 moles of adducts have conventionally been obtained. Method (for example, Japanese Patent Publication No. 60-49621 and Japanese Patent Publication No. 60-5578)
In comparison to the above publications, not only low adducts but also high adducts of oxyalkylene ethers of halogenated diphenols can be obtained. High adducts have low viscosity and good handling properties.
上記効果を奏することから本発明により得られるオキシ
アルキレンエーテルはＬｆ燃性ポリウレタン樹脂あるい
は難燃性ポリエステル繊維の原料などに有用である。Since it exhibits the above-mentioned effects, the oxyalkylene ether obtained by the present invention is useful as a raw material for Lf-flammable polyurethane resin or flame-retardant polyester fiber.
Claims (1)
キシドを付加させて得られる生成物に、アルカリ性触媒
又は酸性触媒の存在下アルキレンオキシドを付加させる
ことにより、淡色なハロゲン化ジフェノール類のオキシ
アルキレンエーテルを得ることを特徴とするオキシアル
キレンエーテルの製造法。 ２、該生成物がハロゲン化ジフェノール１モル当りアル
キレンオキシドを少なくとも１モル付加させたものであ
る特許請求の範囲第１項記載の製造法。[Claims] 1. By adding alkylene oxide to a product obtained by adding alkylene oxide to halogenated diphenols in the presence of an alkaline or acidic catalyst, a light-colored halogenated diphenol can be produced. A method for producing an oxyalkylene ether, which comprises obtaining an oxyalkylene ether of phenols. 2. The production method according to claim 1, wherein the product has at least 1 mole of alkylene oxide added per mole of halogenated diphenol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11928987A JPS63284223A (en) | 1987-05-15 | 1987-05-15 | Manufacture of oxyalkylene ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11928987A JPS63284223A (en) | 1987-05-15 | 1987-05-15 | Manufacture of oxyalkylene ether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63284223A true JPS63284223A (en) | 1988-11-21 |
Family
ID=14757719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11928987A Pending JPS63284223A (en) | 1987-05-15 | 1987-05-15 | Manufacture of oxyalkylene ether |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63284223A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003504499A (en) * | 1999-07-09 | 2003-02-04 | ザ ダウ ケミカル カンパニー | Polymerization of alkylene oxide to functionalized initiator |
-
1987
- 1987-05-15 JP JP11928987A patent/JPS63284223A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003504499A (en) * | 1999-07-09 | 2003-02-04 | ザ ダウ ケミカル カンパニー | Polymerization of alkylene oxide to functionalized initiator |
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