JPS63201148A - Production of 2-phenylisopropylamine - Google Patents
Production of 2-phenylisopropylamineInfo
- Publication number
- JPS63201148A JPS63201148A JP3518387A JP3518387A JPS63201148A JP S63201148 A JPS63201148 A JP S63201148A JP 3518387 A JP3518387 A JP 3518387A JP 3518387 A JP3518387 A JP 3518387A JP S63201148 A JPS63201148 A JP S63201148A
- Authority
- JP
- Japan
- Prior art keywords
- ammonia
- phenylisopropyl
- phenylisopropylamine
- bromide
- parts
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 42
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 23
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000010410 layer Substances 0.000 description 10
- 230000032683 aging Effects 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- WSFSJXBURLJOFD-UHFFFAOYSA-N 2-bromopropan-2-ylbenzene Chemical compound CC(C)(Br)C1=CC=CC=C1 WSFSJXBURLJOFD-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、医薬、農薬、その他有機合成原料として重要
な２−フェニルイソプロピルアミンの製造方法の改良方
法に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to an improved method for producing 2-phenylisopropylamine, which is important as a raw material for pharmaceuticals, agricultural chemicals, and other organic synthesis.
〈従来技術〉
従来、２−フェニルイソプロピルアミンの製造方法とし
ては、２−７エニルインプロビルクロライドをアンモニ
アによりアミノ化する方法が知られている（例えば、ケ
ミカルアブストラクト、第１２巻、Ｐ、 １４６７、特
開昭４８−３６１２９公報など）。<Prior Art> Conventionally, as a method for producing 2-phenylisopropylamine, a method of aminating 2-7enylimpropyl chloride with ammonia is known (for example, Chemical Abstracts, Vol. 12, P, 1467, (Japanese Unexamined Patent Publication No. 48-36129, etc.).
〈発明が解決しようとする問題点〉
しかしながら、２−７エニルイソプロビルクロライドを
アンモニアによりアミノ化する方法では、α−メチルス
チレンの副生が多く、２−フェニルイソプロピルアミン
への選択率は、高々６０％程度である。更に回収α−メ
チルスチレンを２−フェニルイソプロピルクロライドへ
の原料として再使用する場合には、不純物が多く、精製
を必要とする等、工業的に有利な方法とは言えない。<Problems to be solved by the invention> However, in the method of aminating 2-7 enyl isopropyl chloride with ammonia, a large amount of α-methylstyrene is produced as a by-product, and the selectivity to 2-phenyl isopropylamine is very low. It is about 60%. Furthermore, when the recovered α-methylstyrene is reused as a raw material for 2-phenylisopropyl chloride, it contains many impurities and requires purification, which is not an industrially advantageous method.
〈問題点を解決する手段〉
本発明者等は、２−フェニルイソプロピルアミンを工業
的に有利に製造する方法を開発すべく種々検討した結果
、２−フェニルイソプロピルブロマイドを出発原料とし
て用い、特定の条件下で、アンモニアと反応させること
により、驚くべきことに高反応率、高選択率で２−フェ
ニルイソプロピルアミンを工業的に有利に製造できるこ
とを見い出し、本発明を完成した。<Means for Solving the Problems> As a result of various studies in order to develop a method for industrially advantageous production of 2-phenylisopropylamine, the present inventors discovered that using 2-phenylisopropyl bromide as a starting material, a specific It was surprisingly discovered that 2-phenylisopropylamine can be industrially advantageously produced at a high reaction rate and high selectivity by reacting with ammonia under the following conditions, and the present invention was completed.
即ち、本発明は、２−フェニルイソプロピルブロマイド
を、不活性有機溶媒の存在、又は不存在下、アンモニア
と反応させることを特徴とする２−フェニルイソプロピ
ルアミンの製造方法である。That is, the present invention is a method for producing 2-phenylisopropylamine, which is characterized by reacting 2-phenylisopropyl bromide with ammonia in the presence or absence of an inert organic solvent.
ここで、アンモニアの使用量は、２−フェニルイソプロ
ピルブロマイド１モルに対し、２モルより少ないと２−
フェニルイソプロピルアミン選択率の低下、α−メチル
スチレンの副生が増加する傾向を示し、一方、２−フェ
ニルイソプロピルブロマイド１モルに対し、アンモニア
をｌＯモルヨリ多く用いることは、容積効率が悪くなり
、経済的な面で得策とは言えない。Here, the amount of ammonia used is less than 2 moles per 1 mole of 2-phenylisopropyl bromide.
There is a tendency for the phenylisopropylamine selectivity to decrease and the by-product of α-methylstyrene to increase. On the other hand, using more than 10 mole of ammonia per mole of 2-phenylisopropyl bromide leads to poor volumetric efficiency and economical problems. I can't say it's a good idea from a practical standpoint.
従って、アンモニアの使用量は、２−フェニルイソプロ
ピルブロマイド１モルに対し、２〜１０モル、好ましく
は、３〜８モルが適当である。Therefore, the appropriate amount of ammonia to be used is 2 to 10 mol, preferably 3 to 8 mol, per 1 mol of 2-phenylisopropyl bromide.
反応温度は、高過ぎるとα−メチルスチレンが多く副生
じ、目的物である２−フェニルイソプロピルアミンへの
選択率が低下する。一方、反応温度が低いと、選択率は
高くなるものの、反応系の粘度が上昇し、撹拌混合が不
十分となる。If the reaction temperature is too high, a large amount of α-methylstyrene will be produced as a by-product, and the selectivity to the target product, 2-phenylisopropylamine, will decrease. On the other hand, when the reaction temperature is low, although the selectivity increases, the viscosity of the reaction system increases and stirring and mixing become insufficient.
従って、反応温度は通常−１０〜５０℃、内でも一５〜
２０℃が特に好ましい。Therefore, the reaction temperature is usually -10 to 50°C, preferably -15 to 50°C.
20°C is particularly preferred.
反応に当って使用する不活性有機溶媒としては、例えば
ｎ−へキサン、ｎ−ヘプタンなどの脂肪族炭化水素類、
例えばテトラヒドロフラン、ジエチルエーテルなどのエ
ーテル類、例えば酢酸エチルなどのエステル類が用いら
れる。Examples of inert organic solvents used in the reaction include aliphatic hydrocarbons such as n-hexane and n-heptane;
For example, ethers such as tetrahydrofuran and diethyl ether, and esters such as ethyl acetate are used.
本発明の方法の具体的な一実施態様は、アンモニアを密
閉型反応容器に仕込み、所定の反応温度に設定した後、
２−フェニルイソプロピルブロマイドを圧入する。圧入
後、必要に応じて熟成する。In a specific embodiment of the method of the present invention, ammonia is charged into a closed reaction vessel, and after setting the reaction temperature to a predetermined temperature,
2-Phenylisopropyl bromide is forced in. After press-fitting, ripen as necessary.
この様にして得られた２−フェニルイソプロピルアミン
は、脱アンモニア後公知の方法により精製される。The 2-phenylisopropylamine thus obtained is deammoniated and then purified by a known method.
〈発明の効果〉
本発明の方法によれば、２−フェニルイソプロピルブロ
マイドより、２−フェニルイソプロピルアミンを高収率
で製造することができる。又、副生ずるα−メチルスチ
レンを未精製のまま、２−フエニルイソブロピルブロマ
イドの原料として用いることができる。<Effects of the Invention> According to the method of the present invention, 2-phenylisopropylamine can be produced in high yield from 2-phenylisopropyl bromide. Further, the by-produced α-methylstyrene can be used unpurified as a raw material for 2-phenylisopropylbromide.
〈実施例〉
次に、本発明を実施例により更に詳細に説明するが、本
発明はこれらの実施例に限定されるものではない。<Examples> Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
尚、実施例中の部は、特に断わらない限り、重量部を表
わすものとする。In addition, unless otherwise specified, parts in the examples represent parts by weight.
〈実施例−１〉
内容積５００容量部のステンレス製オートクレーブにア
ンモニア１０１部を仕込み、０℃に冷却した後、２−フ
ェニルイソプロピルブロマイド２４６．３部を撹拌下、
５時間で圧入した。０℃、３時間熟成した後、脱アンモ
ニアし、水を加えた。水層のｐＨを１３以上にした後、
分液し、有機層をガスクロ分析した。２−フェニルイソ
プロピルブロマイドの反応率１００％、２−フェニルイ
ソプロピルアミン選択率９０．５％、α−メチルスチレ
ン選択率７．５％であった。<Example-1> 101 parts of ammonia was charged into a stainless steel autoclave with an internal volume of 500 parts by volume, and after cooling to 0°C, 246.3 parts of 2-phenylisopropyl bromide was added with stirring.
It was press-fitted in 5 hours. After aging at 0°C for 3 hours, the mixture was deammoniated and water was added. After adjusting the pH of the aqueous layer to 13 or higher,
The organic layer was separated and subjected to gas chromatography analysis. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 90.5%, and the selectivity of α-methylstyrene was 7.5%.
〈実施例−２〉
内容積５００容量部のステンレス製オートクレーブにア
ンモニア１０１部を仕込み、７℃に冷却した後、２−フ
ェニルイソプロピルブロマイド２４６．３部を撹拌下、
５時間で圧入した。７℃、３時間熟成した後、脱アンモ
ニアし、水を加えた。水層のｐＨを１３以上にした後、
分液し、有機層をガスクロ分析シた。２−フェニルイン
プロピルブロマイドの反応率１００％、２−フェニルイ
ソプロピルアミンの選択率８９．３％、α−メチルスチ
５レン選択率８゜０％であった。<Example-2> 101 parts of ammonia was charged into a stainless steel autoclave with an internal volume of 500 parts by volume, and after cooling to 7°C, 246.3 parts of 2-phenylisopropyl bromide was added with stirring.
It was press-fitted in 5 hours. After aging at 7°C for 3 hours, the mixture was deammoniated and water was added. After adjusting the pH of the aqueous layer to 13 or higher,
The organic layer was separated and subjected to gas chromatography analysis. The reaction rate for 2-phenylipropyl bromide was 100%, the selectivity for 2-phenylisopropylamine was 89.3%, and the selectivity for α-methylstyrene was 8.0%.
〈実施例−３〉
内容積５００容量部のステンレス製オートクレーブにア
ンモニア７３．６部を仕込み、０℃に冷却した後、２−
フェニルイソプロピルブロマイド２４６．３部を撹拌下
、５時間で圧入した。０℃、３時間熟成した後、脱アン
モニアし、水を加えた。水層のｐＨを１３以上にした後
、分液し、有機層をガスクロ分析した。２−フェニルイ
ソプロピルブロマイドの反応率１００％、２−７工ニル
インプロピルアミン選択率８８．０％、α−メチルスチ
レン選択率９．４％であった。<Example-3> 73.6 parts of ammonia was charged into a stainless steel autoclave with an internal volume of 500 parts, and after cooling to 0°C, 2-
246.3 parts of phenylisopropyl bromide was injected under stirring over 5 hours. After aging at 0°C for 3 hours, the mixture was deammoniated and water was added. After adjusting the pH of the aqueous layer to 13 or higher, the layers were separated and the organic layer was subjected to gas chromatography analysis. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-7-enyl-inpropylamine was 88.0%, and the selectivity of α-methylstyrene was 9.4%.
〈実施例−４〉
内容積５００容量部のステンレス製オートクレーブにア
ンモニア７０．８部を仕込み、１０℃にした後、２−フ
ェニルイソプロピルブロマイド１１８．４１ヲ撹拌下、
５時間で圧入した。１０℃、３時間熟成した後、脱アン
モニアし、水を加えた。水層のｐＨを１３以上にした後
、分液し、有機層をガスクロ分析した。２−フェニルイ
ソプロピルブロマイドの反応率１００％、２−フェニル
イソプロピルアミン選択率９３．２％、α−メチルスチ
レン選択率５．３％であった。<Example-4> After charging 70.8 parts of ammonia into a stainless steel autoclave with an internal volume of 500 parts and bringing the temperature to 10°C, 118.41 parts of 2-phenylisopropyl bromide was stirred.
It was press-fitted in 5 hours. After aging at 10°C for 3 hours, the mixture was deammoniated and water was added. After adjusting the pH of the aqueous layer to 13 or higher, the layers were separated and the organic layer was subjected to gas chromatography analysis. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 93.2%, and the selectivity of α-methylstyrene was 5.3%.
〈実施例−５〉
内容積５００容量部のステンレス製オートクレーブにア
ンモニア３７．７１Ｓとｎ−へブタン１００１を仕込み
、０℃にした後、２−フェニルイソプロピルブロマイド
１２６．１部を撹拌下、５時間で圧入した。<Example-5> A stainless steel autoclave with an internal volume of 500 parts was charged with 37.71 S of ammonia and 1001 parts of n-hebutane and heated to 0°C, and then 126.1 parts of 2-phenylisopropyl bromide was added with stirring for 5 hours. I pressed it in.
０℃、３時間熟成した後、脱アンモニアし、水を加えた
。水層のｐＨを１３以上にした後、分液し、有機層をガ
スクロ分析した。２−フェニルイソプロピルブロマイド
の反応率１００％、２−フェニルイソプロピルアミン選
択率９１．０％、α−メチルスチレン選択率７．１％で
あった。After aging at 0°C for 3 hours, the mixture was deammoniated and water was added. After adjusting the pH of the aqueous layer to 13 or higher, the layers were separated and the organic layer was subjected to gas chromatography analysis. The reaction rate of 2-phenylisopropyl bromide was 100%, the selectivity of 2-phenylisopropylamine was 91.0%, and the selectivity of α-methylstyrene was 7.1%.
く比較例−１〉
内容積５００容量部のステンレス製オートクレーブにア
ンモニア１０１部を仕込み、５０℃にした後、２−フェ
ニルイソプロピルクロライド１９１．１部を撹拌下、５
時間で圧入した。５０℃、３時間熟成した後、脱アンモ
ニアし、水を加えた。水層のｐＨを１３以上にした後、
分液し、有機層をガスクロ分析した。２−フェニルイソ
プロピルクロライドの反応率１００％、２−フェニルイ
ソプロピルアミンの選択率５９．０％、α−メチルスチ
レン選択率３７．５％であった。Comparative Example-1> 101 parts of ammonia was charged into a stainless steel autoclave with an internal volume of 500 parts by volume, and the temperature was raised to 50°C.
It was press-fitted in time. After aging at 50°C for 3 hours, the mixture was deammoniated and water was added. After adjusting the pH of the aqueous layer to 13 or higher,
The organic layer was separated and subjected to gas chromatography analysis. The reaction rate of 2-phenylisopropyl chloride was 100%, the selectivity of 2-phenylisopropylamine was 59.0%, and the selectivity of α-methylstyrene was 37.5%.
く比較例−２〉
内容積５００容量部のステンレス製１−トクレーブにア
ンモニア１０１部を仕込み、０℃に冷却した後、２−フ
ェニルイソプロピルクロライド１９１．１部を撹拌下、
５時間で圧入した。０℃、３時間熟成した後、脱アンモ
ニアし、水を加えた。水層のｐＨを１３以上にした後、
分液し、有機層をガスクロ分析した。２−フェニルイソ
プロピルクロライドの反応率は２％であった。Comparative Example-2> 101 parts of ammonia was charged into a stainless steel 1-clave having an internal volume of 500 parts by volume, and after cooling to 0°C, 191.1 parts of 2-phenylisopropyl chloride was added with stirring.
It was press-fitted in 5 hours. After aging at 0°C for 3 hours, the mixture was deammoniated and water was added. After adjusting the pH of the aqueous layer to 13 or higher,
The organic layer was separated and subjected to gas chromatography analysis. The reaction rate of 2-phenylisopropyl chloride was 2%.
Claims (4)
有機溶媒の存在又は不存在下、アンモニアと反応させる
ことを特徴とする２−フェニルイソプロピルアミンの製
造方法。(1) A method for producing 2-phenylisopropylamine, which comprises reacting 2-phenylisopropyl bromide with ammonia in the presence or absence of an inert organic solvent.
ド１モルに対し、２〜１０モル反応させることを特徴と
する特許請求の範囲第１項に記載の２−フェニルイソプ
ロピルアミンの製造方法。(2) The method for producing 2-phenylisopropylamine according to claim 1, which comprises reacting 2 to 10 moles of ammonia with respect to 1 mole of 2-phenylisopropyl bromide.
アとを−１０〜５０℃の温度で反応させることを特徴と
する特許請求の範囲第１項及び第２項に記載の２−フェ
ニルイソプロピルアミンの製造方法。(3) The method for producing 2-phenylisopropylamine according to claims 1 and 2, characterized in that 2-phenylisopropyl bromide and ammonia are reacted at a temperature of -10 to 50°C.
アとを、−５〜２０℃の温度で反応させることを特徴と
する特許請求の範囲第１項及び第２項に記載の２−フェ
ニルイソプロピルアミンの製造方法。(4) A method for producing 2-phenylisopropylamine according to claims 1 and 2, characterized in that 2-phenylisopropyl bromide and ammonia are reacted at a temperature of -5 to 20°C. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3518387A JPH0759536B2 (en) | 1987-02-17 | 1987-02-17 | Method for producing 2-phenylisopropylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3518387A JPH0759536B2 (en) | 1987-02-17 | 1987-02-17 | Method for producing 2-phenylisopropylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63201148A true JPS63201148A (en) | 1988-08-19 |
| JPH0759536B2 JPH0759536B2 (en) | 1995-06-28 |
Family
ID=12434731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3518387A Expired - Fee Related JPH0759536B2 (en) | 1987-02-17 | 1987-02-17 | Method for producing 2-phenylisopropylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0759536B2 (en) |
-
1987
- 1987-02-17 JP JP3518387A patent/JPH0759536B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0759536B2 (en) | 1995-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |