JPH0344080B2 - - Google Patents
Info
- Publication number
- JPH0344080B2 JPH0344080B2 JP9767983A JP9767983A JPH0344080B2 JP H0344080 B2 JPH0344080 B2 JP H0344080B2 JP 9767983 A JP9767983 A JP 9767983A JP 9767983 A JP9767983 A JP 9767983A JP H0344080 B2 JPH0344080 B2 JP H0344080B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound
- group
- formula
- same
- 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
Links
- -1 amine salt Chemical class 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine group Chemical group C(CCC)N(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
本発明は有機環状りん化合物の生成方法に関
し、更に詳しくは、一般式（）
｛一般式（）で、R1〜R8は同一又は相異な
つて、水素原子、ハロゲン厚子、アルキル基、シ
クロアルキル基、アリール基、アラールキル基、
シアノ基、アシル基、又はハロゲンで置換された
アルキル基、アリール基或いはアラールキル基を
示す｝で表わされる有機環状りん化合物の生成方
法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing an organic cyclic phosphorus compound, more specifically, {In the general formula (), R 1 to R 8 are the same or different and are a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group,
The present invention relates to a method for producing an organic cyclic phosphorus compound represented by } representing a cyano group, an acyl group, a halogen-substituted alkyl group, an aryl group, or an aralkyl group.
一般式（）で表わされる有機環状りん化合物
は、各種有機薬品類、界面活性剤、合成樹脂、エ
ラストマー等の空気、光、熱等による劣化、着色
等の防止、難燃化に効果を有し更にこれからの誘
導化合物は各種の基質の物理的化学的性質の改
善、向上に独特の効果を示すものが多く、近年注
目されつつある化合物である。 Organic cyclic phosphorus compounds represented by the general formula () are effective in preventing deterioration and coloring of various organic chemicals, surfactants, synthetic resins, elastomers, etc. due to air, light, heat, etc., and making them flame retardant. Furthermore, many of the derived compounds from these compounds exhibit unique effects on improving and enhancing the physical and chemical properties of various substrates, and are attracting attention in recent years.
一般式（）の化合物は、例えば特公昭49−
45397号及び特公昭50−17979号各公報に記載の様
に、ｏ−フエニルフエノール又はその核置換体と
三塩化りんとを触媒の存在下に加熱反応せしめて
生成する化合物を、加水分解して得られる一般式
（ａ）
｛一般式（ａ）で、R1〜R8は一般式（）
の定義に同じ｝
で表わされる有機りん化合物を、加熱脱水するこ
とによつて得られる。 The compound of general formula () is, for example,
As described in No. 45397 and Japanese Patent Publication No. 50-17979, a compound produced by heating o-phenylphenol or its nuclear substituted product and phosphorus trichloride in the presence of a catalyst is hydrolyzed. The resulting general formula (a) {In general formula (a), R 1 to R 8 are general formula ()
Same as the definition} It can be obtained by heating and dehydrating an organophosphorus compound represented by
一般式（）の化合物は水と反応して一般式
（ａ）の化合物を生成する。即ち上記の加水分
解、脱水反応は反応式（Ａ）に示す通り可逆的で
ある。 A compound of general formula () reacts with water to produce a compound of general formula (a). That is, the above hydrolysis and dehydration reactions are reversible as shown in reaction formula (A).
一般式（）及び（ａ）の化合物は実質的に
水不溶性であるが、一般式（ａ）の化合物に苛
性アルカリ、アンモニア或るいはアミン等を加え
ると、塩を形成して水溶性を増す。 Compounds of general formulas () and (a) are substantially water-insoluble, but when caustic alkali, ammonia, amines, etc. are added to compounds of general formula (a), they form salts and increase water solubility. .
ここで得られる一般式（ａ）のアルカリ金属
塩（ｂ）を加熱すると、例えば特開昭56−
104949号公報に記載の様に、反応式（Ｂ）に示す
通り脱水素反応を起して一般式（ａ）に示す有
機還状りん化合物のアルカリ金属塩を生成する。 When the alkali metal salt (b) of the general formula (a) obtained here is heated, for example,
As described in Japanese Patent No. 104949, a dehydrogenation reaction occurs as shown in reaction formula (B) to produce an alkali metal salt of an organic cyclic phosphorus compound shown in general formula (a).
｛一般式（ｂ）及び（ａ）で、Ｍはアルカ
リ金属原子を示す｝
一般式（ａ）の化合物は鉱酸等により一般式
（ｂ）に示す遊離酸となる。 {In general formulas (b) and (a), M represents an alkali metal atom} The compound of general formula (a) becomes a free acid shown in general formula (b) by a mineral acid or the like.
一般式（ａ）及び（ｂ）の化合物は、水又
は苛性アルカリ水溶液等により加水分解されて一
般式（）又はそのアルカリ金属塩（ｂ）を生
成することはない。 The compounds of general formulas (a) and (b) are not hydrolyzed by water or an aqueous caustic solution to produce general formula () or its alkali metal salt (b).
然るに、一般式（）のA1＝A2＝A3＝Ｈであ
るアンモニウム塩を加熱すると、意外にも脱水・
脱アンモニア反応が起きて一般式（）の化合物
を生成することを見出した。 However, when an ammonium salt with the general formula () where A 1 = A 2 = A 3 = H is heated, it surprisingly dehydrates and
It has been found that a deammonification reaction occurs to produce a compound of general formula ().
更に、一般式（）のA1〜A3の少くとも１つ
がアルキル基であるアミン塩を加熱した場合につ
き検討した結果、塩を形成するアミンの揮発性が
大きい場合は下記反応式（Ｅ）に従つて脱水・脱
アミンが起こり一般式（）の化合物を生成し、
アミンの揮発性が小さい場合は下記反応式（Ｆ）
に従つて脱水素が起り、一般式（ｃ）の化合物
が生成し、アミンの揮発性がその中間である場合
には反応式（Ｅ）と（Ｆ）とが併発することを見
出した。 Furthermore, as a result of studying the case where an amine salt in which at least one of A 1 to A 3 in the general formula () is an alkyl group is heated, if the volatility of the amine forming the salt is high, the following reaction formula (E) Accordingly, dehydration and deamination occur to produce a compound of general formula (),
If the volatility of the amine is low, the following reaction formula (F)
It has been found that dehydrogenation occurs according to the formula (c), and a compound of the general formula (c) is produced, and that when the volatility of the amine is in between, reactions formulas (E) and (F) occur together.
｛但し反応式（Ｅ）及び（Ｆ）において、A1
〜A3がすべて水素原子である場合を除く｝
ここでアミンの揮発性の大小は単に通常状態下
での程度のみでなく、その化合物が置かれる雰囲
気系全体を考慮して判断される。例えば開放系下
又は減圧系下での加熱の場合は、アミンの揮発性
は大きくなつて反応式（Ｅ）に従う分解が促進さ
れる。 {However, in reaction formulas (E) and (F), A 1
~Except when all A 3 are hydrogen atoms} Here, the degree of volatility of an amine is determined not only by the degree under normal conditions but also by taking into account the entire atmosphere system in which the compound is placed. For example, in the case of heating under an open system or a reduced pressure system, the volatility of the amine increases and the decomposition according to reaction formula (E) is promoted.
例えばアミンがメチルアミン、ジメチルアミ
ン、トリメチルアミン、エチルアミン、ジエチル
アミン、トリエチルアミン等の場合は、常圧下の
加熱でも反応式（Ｅ）に従つて一般式（）の化
合物を生成する。 For example, when the amine is methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, etc., the compound of general formula () is produced according to reaction formula (E) even when heated under normal pressure.
一方アミンがトリブチルアミンの場合は、常圧
下の加熱では大部分が反応式（Ｆ）に従つて分解
し一般式（ｃ）の化合物を生成するが、減圧下
で加熱すると大部分が反応式（Ｅ）に従つて分解
し一般式（）の化合物を生成する。 On the other hand, when the amine is tributylamine, when heated under normal pressure, most of it decomposes according to reaction formula (F) to produce a compound of general formula (c), but when heated under reduced pressure, most of it decomposes according to reaction formula (F). E) to produce a compound of general formula ().
分解生成物が、一般式（）の化合物か、一般
式（ｃ）の化合物かの確認は、融点測定、元素
分析（特にＮ）、液体クロマトグラフイー等によ
り行なわれるが、簡単にはよう素（I2）の消費量
測定により行なわれる。即ち一般式（）の化合
物は定量的によう素を消費するのに対し、一般式
（），（ａ），（ｂ），（ａ），（ｂ），（
ｃ）
はよう素を消費しない。 Confirmation of whether the decomposition product is a compound of general formula () or a compound of general formula (c) is performed by melting point measurement, elemental analysis (particularly N), liquid chromatography, etc. This is done by measuring the consumption of (I 2 ). That is, the compound of general formula () consumes iodine quantitatively, whereas the compound of general formula (), (a), (b), (a), (b), (
c)
does not consume iodine.
本発明の方法は、種々の技術的応用が可能であ
る。例えば一般式（）の化合物を水溶液で精製
したのち加熱分解して高純度の一般式（）の化
合物を得ること、紙・繊維・織物等を一般式
（）の化合物の水溶液中に浸漬後加熱分解して
一般式（）の化合物を固着せしめること、樹脂
等の無機フイラーを同様に処理してフイラーの表
面改質や変質防止を企ること等、従来一般式
（）の化合物が水不溶性のため、乳化液や有機
溶媒溶液での処理が必要であつたり、操作が困難
であつた諸問題点が解決される。 The method of the invention is capable of various technical applications. For example, the compound of general formula () is purified in an aqueous solution and then thermally decomposed to obtain a highly pure compound of general formula (), or paper, fibers, textiles, etc. are immersed in an aqueous solution of the compound of general formula () and then heated. Conventionally, the compound of the general formula () has been treated as a water-insoluble compound by decomposing it to fix the compound of the general formula (), or treating an inorganic filler such as a resin in the same way to modify the surface of the filler and prevent deterioration. Therefore, various problems such as the necessity of treatment with an emulsion or an organic solvent solution and the difficulty of operation can be solved.
次に本発明の実施例について述べる。 Next, examples of the present invention will be described.
実施例 １
特公昭49−45397号公報及び特公昭50−17979号
公報の各実施例１に準じて製造した有機りん化合
物｛一般式（ａ）で、R1〜R8＝Ｈのもの｝を、
小過剰のアンモニアを含む水中に60゜〜70℃に保
ちながら撹拌下に少量ずつ投入し、活性炭少量を
加えた後保温過し、液を冷却すると白色結晶
が析出する。これを取して60℃で乾燥すると次
式で表わされる有機りん化合物のアンモニウム塩
が得られる。Example 1 An organic phosphorus compound (with general formula (a), where R 1 to R 8 =H) was prepared according to Example 1 of Japanese Patent Publication No. 49-45397 and Japanese Patent Publication No. 50-17979. ,
Add the solution little by little to water containing a small excess of ammonia while stirring while maintaining the temperature at 60° to 70°C, add a small amount of activated carbon, keep it warm, and cool the solution to precipitate white crystals. When this is taken and dried at 60°C, an ammonium salt of an organophosphorus compound represented by the following formula is obtained.
この化合物500grを内容積1000mlのフラスコに
仕込み、30トールの減圧下に加熱すると94℃付近
から内容物が一部融解しつつ沸騰状態を示しはじ
めるので、昇温速度を緩やかにして加熱を続け約
160℃まで昇温する。内容物は液相が次第に増え
固相が消失し、ガスの発生が終ると分解が終了す
る。130℃付近で内容物を磁製皿に排出し、固化、
粉砕して白色粉末を得る。この化合物は融点
（118℃）、よう素滴定、赤外吸収スペクトル、液
体クロマトグラフ（これらの測定結果は前記反応
式（Ａ）により得られるものと同一である）によ
り下記構造式で示される有機環状りん化合物であ
ることが確認された。 When 500g of this compound is placed in a flask with an internal volume of 1000ml and heated under a reduced pressure of 30 torr, the contents begin to boil around 94°C while partially melting, so the temperature increase rate is slowed down and heating is continued for about 20 minutes.
Raise the temperature to 160℃. The liquid phase of the contents gradually increases, the solid phase disappears, and the decomposition ends when gas generation ends. Drain the contents into a porcelain dish at around 130℃, solidify,
Grind to obtain a white powder. This compound was determined by melting point (118°C), iodine titration, infrared absorption spectrum, and liquid chromatography (these measurement results are the same as those obtained from the reaction formula (A) above) to identify the organic compound represented by the following structural formula. It was confirmed that it was a cyclic phosphorus compound.
又元素分析の結果窒素は不検出であつた。 Also, elemental analysis showed that nitrogen was not detected.
Claims (1)
つて、水素原子、ハロゲン原子、アルキル基、シ
クロアルキル基、アリール基、アラールキル基、
シアノ基、アシル基、又はハロゲンで置換された
アルキル基、アリール基或いはアラールキル基
を、A1〜A3は同一又は相異なつて水素原子又は
低級アルキル基を示す｝ で表わされる有機りん化合物のアンモニウム又は
アミン塩を加熱分解せしめることを特徴とする、
一般式（） ｛一般式（）で、R1〜R8は一般式（）の
定義に同じ｝で表わされる有機環状りん化合物の
生成方法。[Claims] 1 General formula () {In the general formula (), R 1 to R 8 are the same or different and are a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group,
Ammonium of an organophosphorus compound represented by a cyano group, an acyl group, or a halogen-substituted alkyl group, an aryl group, or an aralkyl group, and A 1 to A 3 are the same or different and represent a hydrogen atom or a lower alkyl group} or characterized by thermally decomposing the amine salt,
General formula () A method for producing an organic cyclic phosphorus compound represented by the general formula (), in which R 1 to R 8 are the same as defined in the general formula ().
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9767983A JPS59222496A (en) | 1983-06-01 | 1983-06-01 | Production of organic cyclic phosphorus compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9767983A JPS59222496A (en) | 1983-06-01 | 1983-06-01 | Production of organic cyclic phosphorus compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59222496A JPS59222496A (en) | 1984-12-14 |
| JPH0344080B2 true JPH0344080B2 (en) | 1991-07-04 |
Family
ID=14198679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9767983A Granted JPS59222496A (en) | 1983-06-01 | 1983-06-01 | Production of organic cyclic phosphorus compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59222496A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0529197B1 (en) * | 1991-08-28 | 1998-01-07 | Daicel Chemical Industries, Ltd. | A process for the preparation of a purified 3,4-epoxycyclohexyl-methyl (meth)acrylate . |
| JP2006342217A (en) * | 2005-06-07 | 2006-12-21 | Sanko Kk | Method for producing phosphorus-containing flame-retardant bisphenol-type epoxy resin, the resultant phosphorus-containing flame-retardant bisphenol-type epoxy resin, and phosphorus-containing flame-retardant bisphenol-type epoxy resin composition |
| EP2053053A1 (en) | 2007-10-26 | 2009-04-29 | Ems-Patent Ag | Method for continuous manufacture of an organophosphorus compound and its utilisation |
-
1983
- 1983-06-01 JP JP9767983A patent/JPS59222496A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59222496A (en) | 1984-12-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fields | The synthesis of esters of substituted amino phosphonic acids1a | |
| JPS6086017A (en) | Production of polyhydrogen silsesquioxane | |
| US4216168A (en) | Preparation of high purity tetrahydrocarbylammonium tetrahydridoborates | |
| US2566363A (en) | Tertiary alkoxy amino silanes | |
| Quimby et al. | Tetrasodium carbonyldiphosphonate. Synthesis, reactions, and spectral properties | |
| US3070615A (en) | Novel organo tin compounds | |
| JPH0344080B2 (en) | ||
| JPS6332357B2 (en) | ||
| Popov et al. | Studies on the chemistry of halogens and of polyhalides. X. The reactions of iodine monochloride with pyridine and with 2, 2'-bipyridine1 | |
| Glidewell et al. | Ambidentate nucleophiles. Part 3. Reactions of phosphoroselenoates with molecular halides: the use of 1 J (PSe) as a structural diagnostic | |
| JP2009269820A (en) | Method for producing basket-formed siloxane compound | |
| JPS5888342A (en) | Manufacture of arylamines | |
| CA1105048A (en) | Procedure for the preparation of n-sulphoalkane- aminoalkane-phosphonic acids and their alkali salts, respectively | |
| Werner | LXXXVIII.—The constitution of carbamides. Part I. The preparation of iso carbamides by the action of methyl sulphate on carbamides | |
| JPS5948838B2 (en) | Recovery method for halogenated organotin | |
| US3974209A (en) | Substituted tertiary amines and processes for preparing the same | |
| US3996342A (en) | Method for thermochemical production of hydrogen from water | |
| US4772737A (en) | Hydrolysis of diorganodichlorosilanes | |
| JP2001192347A5 (en) | ||
| Pike et al. | Preparation and Properties of β-Cyanoethyltrichlorosilane1 | |
| CN105566386B (en) | Phenylphosphonothioic acid two（Tribromo phenyl）Ester compounds and preparation method thereof | |
| US2316152A (en) | Process of preparing sulphonium compounds | |
| JP3915872B2 (en) | Method for producing tetrakis (trimethylsilyl) silane and tris (trimethylsilyl) silane | |
| US2417999A (en) | Preparation of n, n'-methylene bis hydantoins | |
| US4182805A (en) | Decyanation |