JP5764336B2 - ペンタメチレンジイソシアネートの製造方法 - Google Patents
ペンタメチレンジイソシアネートの製造方法 Download PDFInfo
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- JP5764336B2 JP5764336B2 JP2011016883A JP2011016883A JP5764336B2 JP 5764336 B2 JP5764336 B2 JP 5764336B2 JP 2011016883 A JP2011016883 A JP 2011016883A JP 2011016883 A JP2011016883 A JP 2011016883A JP 5764336 B2 JP5764336 B2 JP 5764336B2
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- Japan
- Prior art keywords
- pentamethylenediamine
- mass
- pentamethylene diisocyanate
- reaction
- lysine
- 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.)
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- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 title claims description 80
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 225
- 238000006243 chemical reaction Methods 0.000 claims description 69
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- 150000003839 salts Chemical class 0.000 claims description 43
- 239000007864 aqueous solution Substances 0.000 claims description 39
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 31
- 239000004472 Lysine Substances 0.000 claims description 29
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- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 3
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
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- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- YAHWUJOBZVKEGY-UHFFFAOYSA-N tridecane-1-sulfonamide Chemical compound CCCCCCCCCCCCCS(N)(=O)=O YAHWUJOBZVKEGY-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- FCFIEBVTVHJMQR-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphite Chemical compound ClCC(Cl)COP(OCC(Cl)CCl)OCC(Cl)CCl FCFIEBVTVHJMQR-UHFFFAOYSA-N 0.000 description 1
- UTAXICGCDMYKKJ-UHFFFAOYSA-N tris(2-ethylhexyl)phosphane Chemical compound CCCCC(CC)CP(CC(CC)CCCC)CC(CC)CCCC UTAXICGCDMYKKJ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<ペンタメチレンジアミンの反応収率(単位:mol%)>
L−リシン一塩酸塩(和光純薬工業社製)、および、後述する(ペンタメチレンジアミンの蒸留)で得られた精製ペンタメチレンジアミンを用い、以下のHPLC(高速液体クロマトグラフ)分析条件下で得られたクロマトグラフの面積値から作成した検量線により、ペンタメチレンジアミンの濃度を算出し、L−リシン一塩酸塩およびペンタメチレンジアミンの合計濃度に対するペンタメチレンジアミンの濃度の割合を、ペンタメチレンジアミンの反応収率とした。
カラム温度;40℃
溶離液;0.2mol/L リン酸ナトリウム(pH7.7)+2.3mmol/L 1−オクタンスルホン酸ナトリウム
流量;0.5mL/min
L−リシン一塩酸塩およびペンタメチレンジアミンの検出には、オルトフタルアルデヒドを用いたポストカラム誘導体化法〔J.Chromatogr.,83,353−355(1973)〕を採用した。
<ペンタメチレンジアミン二塩酸塩の濃度(単位:質量%)>
上記したペンタメチレンジアミンの反応収率と同様の方法にて、ペンタメチレンジアミンの濃度を測定し、ペンタメチレンジアミン二塩酸塩の濃度に換算した。
<ペンタメチレンジアミン二塩酸塩スラリーの含水率(単位:質量%)>
水分計(AQV−7、平沼産業製)を用い、カールフィッシャー試薬として、ハイドラナール・コンポジット5(シグマアルドリッジジャパン製)を用いて、ペンタメチレンジアミン二塩酸塩スラリーの含水率を測定した。
<ペンタメチレンジイソシアネートの純度(単位:質量%)>
ペンタメチレンジイソシアネートの純度は、電位差滴定装置を用いて、JIS K−1603−1に準拠し、n−ジブチルアミン法により測定したイソシアネート基濃度から、算出した。
<ペンタメチレンジイソシアネート反応液の濃度(単位:質量%)>
実施例1で得られた精製ペンタメチレンジシソシアネートを用い、以下のガスクロマトグラフ分析条件で得られたガスクロマトグラムの面積値から作成した検量線から、ペンタメチレンジシソシアネート反応液の濃度を求めた。
カラム;UA−20EX−2.0F、1.2mmφ×20m(フロンティア・ラボ社製)
オーブン温度;100℃で2分間保持、100℃から240℃まで、10℃/minで昇温、240℃で14分間保持
注入口温度;250℃
検出器温度;250℃
キャリアガス;ヘリウム
検出方法;FID
<ペンタメチレンジイソシアネート反応液の反応率(単位:%)>
(1)実施例のペンタメチレンジイソシアネート反応液の反応率
実施例のペンタメチレンジイソシアネート反応液の反応率は以下の式を用いて算出した。
C2/{(W1×C1×M2/M1)/(W1×(100−C1)+W1×C1×M2/M1)}
M1:ペンタメチレンジアミン二塩酸塩の分子量
M2:ペンタメチレンジイソシアネートの分子量
C1:ペンタメチレンジアミン二塩酸塩スラリーの固形分濃度
C2:ペンタメチレンジイソシアネート反応液の濃度
W1:仕込んだペンタメチレンジアミン二塩酸塩スラリーの質量部
(2)比較例のペンタメチレンジイソシアネート反応液の反応率
比較例のペンタメチレンジイソシアネートの収率は以下の式を用いて算出した。
C2/{(W2×M2/M3)/(W3+W2×M2/M3)}
C2:ペンタメチレンジイソシアネート反応液の濃度
M2:ペンタメチレンジイソシアネートの分子量
M3:ペンタメチレンジアミンの分子量
W2:仕込んだペンタメチレンジアミンの質量部
W3:仕込んだo−ジクロロベンゼンの質量部
<ペンタメチレンジイソシアネート反応液の収率(単位:質量%)>
(1) 実施例のペンタメチレンジイソシアネートの収率
実施例のペンタメチレンジイソシアネートの収率は、上記(ペンタメチレンジイソシアネート反応液の反応率)とした。
(2) 比較例のペンタメチレンジイソシアネートの収率
比較例のペンタメチレンジイソシアネートの収率は以下の式を用いて算出した。
(a):抽出率(後述)
(b):ペンタメチレンジアミンの収率(後述)
(c):ペンタメチレンジイソシアネート反応液の反応率
<抽出率(単位:質量%)>
抽出率は以下の式を用いて算出した。
C3:仕込んだペンタメチレンジアミン水溶液のペンタメチレンジアミンの純度
C4:有機層のペンタメチレンジアミンの純度(後述)
W4:仕込んだペンタメチレンジアミン水溶液の質量部
W5:抽出後の有機層の質量部
<ペンタメチレンジアミンの純度(単位:質量%)>
後述する(ペンタメチレンジアミンの蒸留)で得られた精製ペンタメチレンジアミンを用い、以下のガスクロマトグラフ分析条件で得られたガスクロマトグラムの面積値から作成した検量線により、ペンタメチレンジアミンの純度を算出した。
カラム;WCOT FUSED SILICA CP−SIL 8CB FOR AMINES(VARIAN社製)
オーブン温度;40℃で3分間保持、40℃から300℃まで、10℃/minで昇温、300℃で11分間保持
注入口温度;250℃
検出器温度;280℃
キャリアガス;ヘリウム
検出法;FID
<ペンタメチレンジアミンの収率(単位:質量%)>
ペンタメチレンジアミンの収率は以下の式を用いて算出した。
C4:有機層のペンタメチレンジアミンの純度
C5:蒸留後のペンタメチレンジアミンの純度
W6:仕込んだ有機層の質量部
W7:蒸留後のペンタメチレンジアミンの質量部
(ペンタメチレンジアミンの蒸留)
温度計、蒸留塔、冷却管および窒素導入管を備えた4つ口フラスコに、ペンタメチレンジアミン(東京化成社製)を仕込み、塔頂温度が111〜115℃、10KPaの条件下、さらに還流しながら精留し、精製ペンタメチレンジアミンを得た。蒸留精製したペンタメチレンジアミンは、ガスクロマトグラフィーの面積比が100%であった。
(リジン脱炭酸酵素遺伝子(cadA)のクローニング)
Escherichia coli W3110株(ATCC27325)から常法に従い調製したゲノムDNAをPCRの鋳型に用いた。
(形質転換体の作製)
pCADAを用いてEscherichia coli W3110株を通常の方法で形質転換し、得られた形質転換体をW/pCADAと命名した。
・水溶液調製工程
フラスコに、L−リシン一塩酸塩(和光純薬製)を、終濃度が45質量%となるように、および、ピリドキサールリン酸(和光純薬製)を、終濃度が0.15mmol/Lとなるように調製した基質溶液120質量部を加えた。次に、上記のW/pCADA菌体破砕液(仕込み乾燥菌体換算重量0.3g)を添加し反応を開始した。反応条件は37℃、200rpmとした。反応液のpHは6mol/Lの塩酸にてpH6に調整した。24時間後のペンタメチレンジアミンの反応収率は99%に達していた。上記の反応24時間後の反応液を、6mol/Lの塩酸にてpH2に調整し、0.6質量部の活性炭(三倉化成社製 粉末活性炭PM−SX)を添加し、25℃で1時間攪拌を行った後、濾紙(ADVANTEC社製 5C)にて濾過を行い、ペンタメチレンジアミン二塩酸塩水溶液(31.9質量%水溶液)を得た。
・スラリー調製工程
フラスコに、撹拌羽、温度計、および二つの均圧管付の滴下ロートを備え、一方はo−ジクロロベンゼン(以下、ODCBと略する場合がある)滴下用とし、もう一方は、上部に冷却管を設置した留出液の受器とし、冷却管を真空ポンプのラインにつなげた。フラスコに上記で得られたペンタメチレンジアミン二塩酸塩水溶液1000質量部を仕込み、滴下ロートにo−ジクロロベンゼン2141質量部を仕込んだ。冷却管には5℃の冷媒を通液し、受器とした滴下ロートのコックは閉とし、20kPaの減圧下、内温を80℃、回転数を200rpmとし、共沸させることにより、一次脱水を行った。水が200質量部留出した時点で、o−ジクロロベンゼンを200質量部滴下し、20kPaの減圧下、内温を110℃、回転数を500rpmとし、共沸させることにより、二次脱水を行った。さらに、485g/Hの速度でオルトジクロロベンゼンを滴下し、さらに、受器とした滴下ロートに留出したオルトジクロロベンゼンは、随時、フラスコに添加した。滴下終了後、0.5時間、20kPaの減圧下での加熱撹拌を継続し、脱水を終了した。得られたペンタメチレンジアミン二塩酸塩スラリー(a)の含水率は0.08質量%(800ppm)、ペンタメチレンジアミン二塩酸塩スラリーの固形分濃度は13質量%であった。
・ホスゲン導入工程
電磁誘導撹拌機、自動圧力調整弁、温度計、窒素導入ライン、ホスゲン導入ライン、凝縮器、原料フィードポンプを備え付けたジャケット付き加圧反応器に、上記ペンタメチレンジアミン二塩酸塩スラリー(a)を1350質量部仕込んだ。次いで、ホスゲン594質量部をホスゲン導入ラインから加え、撹拌を開始した。内液を徐々に150℃まで昇温し、0.25MPaに加圧し、反応温度165℃で300分間熱ホスゲン化した。なお、熱ホスゲン化の途中で、ホスゲン594質量部を、さらに添加した。熱ホスゲン化終了後、100〜140℃において、窒素ガスを100L/Hで通気、脱ガスし、ペンタメチレンジイソシアネート反応液(a)を1330質量部得た。ペンタメチレンジイソシアネート反応液(a)の濃度は11.0質量%、反応率、および収率は94.9質量%であった。
次いで、留去させたペンタメチレンジイソシアネートを、攪拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに装入し、窒素を導入しながら、常圧下で、190℃、3時間加熱処理を行った。
・水溶液調製工程
実施例1の水溶液調製工程と同様にして、ペンタメチレンジアミン二塩酸塩水溶液(31.9質量%水溶液)を得た。
・スラリー調製工程
フラスコに、撹拌羽、温度計、および二つの均圧管付の滴下ロートを備え、一方はペンタメチレンジアミン二塩酸塩水溶液滴下用とし、もう一方は、上部に冷却管を設置した留出液の受器とし、冷却管を真空ポンプのラインにつなげた。フラスコにo−ジクロロベンゼン2141質量部を仕込み、滴下ロートに上記ペンタメチレンジアミン二塩酸塩1000質量部を仕込んだ。冷却管には5℃の冷媒を通液し、受器とした滴下ロートのコックは閉とし、20kPaの減圧下、内温を110℃、回転数を500rpmとし、ペンタメチレンジアミン水溶液を167g/Hで滴下しながら共沸させることにより、脱水を行った。さらに、受器とした滴下ロートに留出したo−ジクロロベンゼンは、随時、フラスコに添加した。滴下終了後、0.5時間、20kPaの減圧下での加熱撹拌を継続し、脱水を終了した。得られたペンタメチレンジアミン二塩酸塩スラリー(b)の含水率は0.06質量%(600ppm)、ペンタメチレンジアミン二塩酸塩スラリーの固形分濃度は13質量%であった。
・ホスゲン導入工程
電磁誘導撹拌機、自動圧力調整弁、温度計、窒素導入ライン、ホスゲン導入ライン、凝縮器、原料フィードポンプを備え付けたジャケット付き加圧反応器に、ペンタメチレンジアミン二塩酸塩スラリー(b)を1350質量部仕込んだ。次いで、ホスゲン594質量部をホスゲン導入ラインから加え、撹拌を開始した。内液を徐々に150℃まで昇温し、0.25MPaに加圧し、反応温度165℃で300分間熱ホスゲン化した。なお、熱ホスゲン化の途中で、ホスゲン594質量部を、さらに添加した。熱ホスゲン化終了後、100〜140℃において、窒素ガスを100L/Hで通気、脱ガスし、ペンタメチレンジイソシアネート反応液(b)を1330質量部得た。ペンタメチレンジイソシアネート反応液(b)の濃度は11.1質量%、反応率、および収率は95.3質量%であった。
実施例1の水溶液調製工程と同様にして、ペンタメチレンジアミン二塩酸塩水溶液(31.9質量%水溶液)を得た。
実施例1の水溶液調製工程と同様にして、ペンタメチレンジアミン二塩酸塩水溶液(31.9質量%水溶液)を得た。
(考察)
ペンタメチレンジアミン水溶液から、そのスラリーを得た後、そのスラリーにホスゲンを導入することによりペンタメチレンジイソシアネートを製造した実施例1(収率:94.9質量%)および実施例2(収率:95.3質量%)では、ペンタメチレンジアミン水溶液からペンタメチレンジアミンを一度単離し、その後、スラリー化およびホスゲンを導入した比較例1(収率:83.6質量%)に比べ、高い収率でペンタメチレンジイソシアネートを得ることができた。
Claims (4)
- リシンおよび/またはその塩の脱炭酸酵素反応により、ペンタメチレンジアミンまたはその塩を含有する水溶液を得る水溶液調製工程、
前記水溶液に、非水溶性有機溶剤を添加するとともに、脱水することにより、ペンタメチレンジアミンまたはその塩のスラリーを得るスラリー調製工程、および、
前記スラリーにホスゲンを導入するホスゲン導入工程
を備えることを特徴とする、ペンタメチレンジイソシアネートの製造方法。 - 前記スラリー調製工程において、共沸脱水することを特徴とする、請求項1に記載のペンタメチレンジイソシアネートの製造方法。
- 前記共沸脱水における圧力条件が、1〜101.3kPa、温度条件が、30〜180℃であることを特徴とする、請求項2に記載のペンタメチレンジイソシアネートの製造方法。
- 前記スラリーが、2000ppm以下の割合で水を含有することを特徴とする、請求項1〜3のいずれか一項に記載のペンタメチレンジイソシアネートの製造方法。
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