JPH0240059B2 - - Google Patents
Info
- Publication number
- JPH0240059B2 JPH0240059B2 JP59017164A JP1716484A JPH0240059B2 JP H0240059 B2 JPH0240059 B2 JP H0240059B2 JP 59017164 A JP59017164 A JP 59017164A JP 1716484 A JP1716484 A JP 1716484A JP H0240059 B2 JPH0240059 B2 JP H0240059B2
- Authority
- JP
- Japan
- Prior art keywords
- acids
- aminododecanoic
- acid
- catalyst
- added
- 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
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical class NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- YKHZGLKQBYTRHO-UHFFFAOYSA-N 11-cyanoundecanoic acid Chemical compound OC(=O)CCCCCCCCCCC#N YKHZGLKQBYTRHO-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- QUBNFZFTFXTLKH-UHFFFAOYSA-N 2-aminododecanoic acid Chemical class CCCCCCCCCCC(N)C(O)=O QUBNFZFTFXTLKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- -1 alkali metal salt Chemical class 0.000 claims description 3
- 239000013522 chelant Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NSTXLXGRDZNHGD-UHFFFAOYSA-N 12-(11-carboxyundecylamino)dodecanoic acid Chemical compound OC(=O)CCCCCCCCCCCNCCCCCCCCCCCC(O)=O NSTXLXGRDZNHGD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- YCVJHQSECYGGPB-UHFFFAOYSA-N azane;11-cyanoundecanoic acid Chemical compound [NH4+].[O-]C(=O)CCCCCCCCCCC#N YCVJHQSECYGGPB-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は12―アミノドデカン酸類の製造方法に
関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 12-aminododecanoic acids.
アミノドデカン酸は工業的に有用な物質であ
り、ポリアミド原料、エポキシ樹脂の硬化剤また
はポリエステルの改質剤として用いられるが、そ
の使用に際しては特に高純度のものが要求されて
いる。 Aminododecanoic acid is an industrially useful substance and is used as a raw material for polyamides, a curing agent for epoxy resins, or a modifier for polyesters, but when it is used, particularly high purity is required.
本発明者らは先に、11―シアノウンデカン酸を
水素添加する12―アミノドデカン酸の製法におい
て、ルテニウム、ロジウム、パルジウム及び白金
からなる群から選ばれた金属を炭化ケイ素担体に
担持させた触媒を使用し、温度20〜200℃、圧力
常圧〜350Kg／cm2、溶媒として低級アルコールと
水との混合溶媒を使用し、第二級アミノ酸（主に
12、12′―イミノビスドデカン酸）の副生を抑制
するためにアンモニアを反応系内に存在させる方
法を提案（特開昭51−127022（特公昭55−45066）
公報参照）した。 The present inventors previously developed a catalyst in which a metal selected from the group consisting of ruthenium, rhodium, paldium, and platinum was supported on a silicon carbide carrier in a method for producing 12-aminododecanoic acid by hydrogenating 11-cyanoundecanoic acid. The temperature is 20 to 200℃, the pressure is normal pressure to 350Kg/ cm2 , and the solvent is a mixed solvent of lower alcohol and water.
Proposed a method in which ammonia is present in the reaction system in order to suppress the by-product of 12,12'-iminobisdodecanoic acid (Japanese Patent Publication No. 51-127022 (Japanese Patent Publication No. 55-45066))
(see official bulletin).
しかしながら、前記の条件下で12―アミノドデ
カン酸を得る場合に、副生物としてかなり多量の
第二級アミノ酸が生成し、また長時間連続して反
応を行なうと反応生成物が着色し、しかも重金属
及び灰分を不純物として多量含有し、触媒活性が
急激に低下する。 However, when obtaining 12-aminododecanoic acid under the above conditions, a considerable amount of secondary amino acids are produced as by-products, and if the reaction is carried out continuously for a long time, the reaction product becomes colored, and heavy metals It contains a large amount of ash and ash as impurities, and the catalyst activity decreases rapidly.
さらに、この反応生成物を数回再結晶した12―
アミノドデカン酸を重合させても同じ相対粘度を
有しても溶融粘度がかなり低くなり、得られたポ
リマーが着色する傾向があつた。 Furthermore, this reaction product was recrystallized several times to give 12-
Even when aminododecanoic acid was polymerized with the same relative viscosity, the melt viscosity was considerably lower and the resulting polymer tended to be colored.
そこで本発明者らは、反応生成物から第二級ア
ミノ酸、着色物質等の不純物を除去することを目
的に鋭意検討した結果、本発明に到達した。 Therefore, the present inventors conducted extensive studies aimed at removing impurities such as secondary amino acids and colored substances from the reaction product, and as a result, they arrived at the present invention.
すなわち、本発明は11―シアノウンデカン酸、
そのアルカリ金属塩、そのアンモニウム塩または
その低級アルキルエステルを貴金属触媒の存在
下、水素添加する12―アミノドデカン酸類の製法
において、金属イオンと結合して水溶性キレート
化合物を形成するポリアミノカルボン酸類からな
る群から選ばれた１種の化学物質を反応系内に添
加することを特徴とする12―アミノドデカン酸類
の製造方法である。 That is, the present invention provides 11-cyanoundecanoic acid,
A process for producing 12-aminododecanoic acids in which an alkali metal salt, an ammonium salt, or a lower alkyl ester thereof is hydrogenated in the presence of a noble metal catalyst, consisting of polyaminocarboxylic acids that combine with metal ions to form a water-soluble chelate compound. This is a method for producing 12-aminododecanoic acids, which is characterized by adding one type of chemical substance selected from the group into the reaction system.
この発明の方法で貴金属触媒を一緒に添加する
前記化学物質は、主に鉄、ニツケルなどの重金属
と水溶性キレート化合物を形成するもので、エチ
レンジアミン四酢酸などのポリアミノカルボン酸
類等があげられる。 The chemical substances to which the noble metal catalyst is added in the method of the present invention mainly form water-soluble chelate compounds with heavy metals such as iron and nickel, and include polyaminocarboxylic acids such as ethylenediaminetetraacetic acid.
この化学物質の添加量は、水添反応器へのフイ
ード液（触媒を含む）100重量部に対して0.001〜
0.1重量部、特に0.002〜0.01重量部が好ましい。
また、前記化学物質は水溶液状あるいは固体状と
してフイード液に添加すればよい。 The amount of this chemical substance added is 0.001 to 100 parts by weight of the feed liquid (including catalyst) to the hydrogenation reactor.
0.1 part by weight is preferred, especially 0.002 to 0.01 part by weight.
Further, the chemical substance may be added to the feed liquid in the form of an aqueous solution or a solid.
本発明の方法により、11―シアノウンデカン酸
類を水素添加して12―アミノドデカン酸類を製造
した場合、長期の連続反応において触媒は高活性
を維持し、反応生成物に含有する重金属及び灰分
が著しく減少し、反応生成物の着色も認められな
かつた。 When 12-aminododecanoic acids are produced by hydrogenating 11-cyanoundecanoic acids by the method of the present invention, the catalyst maintains high activity during long-term continuous reactions, and the heavy metals and ash content contained in the reaction product are significantly reduced. The coloring of the reaction product was not observed.
しかも通常の晶析精製によつて得られた最終生
成物中の重金属含有量は、従来の0.3〜0.5ppmか
ら0.1ppm以下へ、また灰分が３〜6ppmから１〜
1.5ppmへと著しく減少した。 Furthermore, the heavy metal content in the final product obtained by ordinary crystallization purification has been reduced from the conventional 0.3 to 0.5 ppm to 0.1 ppm or less, and the ash content has been reduced from 3 to 6 ppm to 1 to 1.
It decreased significantly to 1.5ppm.
さらに、最終生成物を重合して得られたポリマ
ーは同じ相対粘度を有していても溶融粘度が高く
なり、着色も認められなかつた。 Furthermore, even though the polymer obtained by polymerizing the final product had the same relative viscosity, it had a higher melt viscosity and no coloration was observed.
次に本発明の実施例と比較例を示す。 Next, examples of the present invention and comparative examples will be shown.
実施例 １
日本エンゲルハルト(株)製0.5％Ru／sic触媒5gを
水素流100ml／min中、温度130℃、16時間活性化
したものを容量500mlの電磁攪拌式オートクレー
ブ中に入れ、11―シアノウンデカン酸14ｇをｎ―
BuOH140mlと28％アンモニア水140mlとの混合溶
媒に溶かしたものをオートクレーブに仕込み、さ
らにエチレンジアミン四酢酸を0.001ｇあるいは
0.01ｇ添加し、系内を数回窒素ガスでパージ後、
水素ガスで100Kg／cm2迄加圧した。オートクレー
ブを130℃迄加熱し、以後この温度で保つたまま
攪拌を続けた。30分後には水素ガスの吸収がみら
れなくなつたので約70℃迄冷却し、放圧後反応液
をオートクレーブから取出し、溶媒を留去した後
得られた結晶はほとんど12―アミノドデカン酸で
あり、いずれも0.1重量％の第二級アミンを含有
しているのみであつた。Example 1 5 g of 0.5% Ru/sic catalyst manufactured by Nippon Engelhardt Co., Ltd. was activated in a hydrogen flow of 100 ml/min at a temperature of 130°C for 16 hours, and then placed in a 500 ml electromagnetic stirring autoclave. 14g of undecanoic acid n-
A mixture of 140 ml of BuOH and 140 ml of 28% ammonia water was dissolved in an autoclave, and then 0.001 g of ethylenediaminetetraacetic acid or
After adding 0.01g and purging the system with nitrogen gas several times,
The pressure was increased to 100 kg/cm 2 with hydrogen gas. The autoclave was heated to 130°C, and stirring was continued while maintaining this temperature. After 30 minutes, absorption of hydrogen gas was no longer observed, so the temperature was cooled to about 70°C, the pressure was released, the reaction solution was taken out from the autoclave, and the solvent was distilled off. Most of the crystals obtained were 12-aminododecanoic acid. Both contained only 0.1% by weight of secondary amine.
比較例 １
実施例１においてエチレンジアミン四酢酸を添
加しない場合は、同様に操作して得られた結晶は
0.65重量％の第二級アミンを含有していた。Comparative Example 1 When ethylenediaminetetraacetic acid was not added in Example 1, the crystals obtained by the same operation were as follows.
It contained 0.65% by weight secondary amine.
実施例 ２
日本エンゲルハルト(株)製0.5％Ru／sic触媒５ｇ
を水素流100ml／min中、温度130℃、16時間活性
化したものを容量500mlの電磁攪拌式オートクレ
ーブ中に入れ、11―シアノウンデカン酸14ｇをｎ
―BuOH140mlと28％アンモニア水140mlとの混合
溶媒に溶かしたものをオートクレーブに仕込み、
水酸化第２鉄0.04ｇ添加し、さらにエチレンジア
ミン四酢酸を0.15ｇ添加し、系内を数回窒素ガス
でパージ後、水素ガスで100Kg／cm2迄加圧した。
オートクレーブを130℃迄加熱し、以後この温度
で保つたまま攪拌を続けた。30分後には水素ガス
の吸収がみられなくなつたので約70℃迄冷却し、
放圧後反応液をオートクレーブから取出し、溶媒
を留去した後得られた結晶のほとんどは12―アミ
ノドデカン酸であり、アミン価99.4重量％で、
0.25％の第二級アミンを含有しているのみであつ
た。また、水素ガス吸収速度は43mmolH2／ｇ
―cat分であつた。Example 2 0.5% Ru/sic catalyst manufactured by Nippon Engelhard Co., Ltd. 5 g
was activated in a hydrogen flow of 100 ml/min at a temperature of 130°C for 16 hours, then placed in a 500 ml electromagnetic stirring autoclave, and 14 g of 11-cyanoundecanoic acid was added to the
-Pour the mixture of 140ml of BuOH and 140ml of 28% ammonia water into an autoclave.
0.04 g of ferric hydroxide was added, and further 0.15 g of ethylenediaminetetraacetic acid was added, the inside of the system was purged several times with nitrogen gas, and then pressurized to 100 kg/cm 2 with hydrogen gas.
The autoclave was heated to 130°C, and stirring was continued while maintaining this temperature. After 30 minutes, hydrogen gas was no longer absorbed, so it was cooled to about 70℃.
After releasing the pressure, the reaction solution was taken out from the autoclave and the solvent was distilled off. Most of the crystals obtained were 12-aminododecanoic acid, with an amine value of 99.4% by weight.
It contained only 0.25% secondary amine. Also, the hydrogen gas absorption rate is 43mmolH2/g
-It was a cat minute.
比較例 ２
実施例２においてエチレンジアミン四酢酸を添
加しない場合は、同様に操作して得られた結晶は
total―アミン価91.2重量％で、2.98％の第二級ア
ミンを含有していた。また、水素ガス吸収速度は
30mmolH2／ｇ―cat分であつた。Comparative Example 2 When ethylenediaminetetraacetic acid was not added in Example 2, the crystals obtained by the same operation were
The total amine value was 91.2% by weight and contained 2.98% secondary amine. In addition, the hydrogen gas absorption rate is
It was 30 mmolH2/g-cat.
実施例 ３
11―シアノウンデカン酸アンモニウム塩５重量
部のフイード液（触媒を含む）100重量部にエチ
レンジアミン四酢酸を0.002重量部を加え40atm、
温度110℃で水添反応した。この結果、触媒ライ
フ240倍を超えても第二級アミノ酸の生成率は0.3
％であつた。また、この水添反応液を晶析精製し
た12―アミノドデカン酸の結晶は溶融Hz10〜15、
灰分0.8〜1.5ppm、鉄分0.03〜0.1ppmであつた。Example 3 0.002 parts by weight of ethylenediaminetetraacetic acid was added to 100 parts by weight of a feed liquid (containing catalyst) containing 5 parts by weight of ammonium 11-cyanoundecanoate, and the mixture was heated to 40 atm.
A hydrogenation reaction was carried out at a temperature of 110°C. As a result, even if the catalyst life exceeds 240 times, the production rate of secondary amino acids is 0.3
It was %. In addition, the crystals of 12-aminododecanoic acid obtained by crystallizing and purifying this hydrogenation reaction solution were melted at Hz 10 to 15.
The ash content was 0.8 to 1.5 ppm, and the iron content was 0.03 to 0.1 ppm.
この12―アミノドデカン酸の重合物は、成形直
後カラーメーターYI値無色（−20.2）、屋外暴露
７日無色（−20.1）、サンシヤイン102時間無色
（−16.9）であつた。 This 12-aminododecanoic acid polymer was colorless (-20.2) in color meter YI value immediately after molding, colorless (-20.1) after 7 days of outdoor exposure, and colorless (-16.9) after 102 hours of sunlight exposure.
比較例 ３
実施例３においてエチレンジアミン四酢酸を添
加しない場合は、触媒ライフ140倍で触媒活性が
急激に低下し、第二級アミノ酸の生成率は3.2％
であつた。また、この間水添反応液を晶析精製し
た12―アミノドデカン酸の結晶は、溶融Hz15〜
30、灰分３〜6ppm、鉄分0.3〜0.5ppmであつた。Comparative Example 3 In Example 3, when ethylenediaminetetraacetic acid was not added, the catalyst activity rapidly decreased after 140 times the catalyst life, and the production rate of secondary amino acids was 3.2%.
It was hot. In addition, the crystals of 12-aminododecanoic acid obtained by crystallizing and purifying the hydrogenation reaction solution during this period were melted at Hz15~
30, the ash content was 3 to 6 ppm, and the iron content was 0.3 to 0.5 ppm.
この12―アミノドデカン酸の重合物は、成形直
後カラーメーターYI値微黄（−5.0）、屋外暴露７
日微黄（−2.1）、サンシヤイン102時間微黄（−
3.1）であつた。 This 12-aminododecanoic acid polymer had a color meter YI value of slightly yellow (-5.0) immediately after molding, and an outdoor exposure of 7.
Sunshine 102 hours slightly yellow (-2.1), Sunshine 102 hours slightly yellow (-
3.1).
Claims (1)
塩、そのアンモニウム塩、またはその低級アルキ
ルエステルを貴金属触媒の存在下、水素添加する
12―アミノドデカン酸類の製法において、金属イ
オンと結合して水溶性キレート化合物を形成する
ポリアミノカルボン酸類からなる群から選ばれた
１種の化学物質を添加することを特徴とする12―
アミノドデカン酸類の製法。1 Hydrogenating 11-cyanoundecanoic acid, its alkali metal salt, its ammonium salt, or its lower alkyl ester in the presence of a noble metal catalyst.
A method for producing 12-aminododecanoic acids, characterized by adding one type of chemical substance selected from the group consisting of polyaminocarboxylic acids that combine with metal ions to form water-soluble chelate compounds.12-
Process for producing aminododecanoic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59017164A JPS60163849A (en) | 1984-02-03 | 1984-02-03 | Preparation of 12-aminododecanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59017164A JPS60163849A (en) | 1984-02-03 | 1984-02-03 | Preparation of 12-aminododecanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60163849A JPS60163849A (en) | 1985-08-26 |
| JPH0240059B2 true JPH0240059B2 (en) | 1990-09-10 |
Family
ID=11936314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59017164A Granted JPS60163849A (en) | 1984-02-03 | 1984-02-03 | Preparation of 12-aminododecanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60163849A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5434307A (en) * | 1993-05-21 | 1995-07-18 | Howard University | Synthesis of 12-oxododecanoic acid oxime from vernolic acid |
-
1984
- 1984-02-03 JP JP59017164A patent/JPS60163849A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60163849A (en) | 1985-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |