JP2015500894A5 - - Google Patents
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- Publication number
- JP2015500894A5 JP2015500894A5 JP2014542868A JP2014542868A JP2015500894A5 JP 2015500894 A5 JP2015500894 A5 JP 2015500894A5 JP 2014542868 A JP2014542868 A JP 2014542868A JP 2014542868 A JP2014542868 A JP 2014542868A JP 2015500894 A5 JP2015500894 A5 JP 2015500894A5
- Authority
- JP
- Japan
- Prior art keywords
- formaldehyde
- oxymethylene
- aprotic compound
- catalyst
- weight
- 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
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 107
- 238000000034 method Methods 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000000178 monomer Substances 0.000 claims description 20
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- -1 cyclic acetal Chemical class 0.000 claims description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 239000008098 formaldehyde solution Substances 0.000 claims description 2
- 239000008246 gaseous mixture Substances 0.000 claims description 2
- 239000011964 heteropoly acid Substances 0.000 claims description 2
- 230000000415 inactivating effect Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 0 CC(C*C1)CS1(=O)=O Chemical compound CC(C*C1)CS1(=O)=O 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11190574.1 | 2011-11-24 | ||
| EP11190586.5 | 2011-11-24 | ||
| EP11190567.5 | 2011-11-24 | ||
| EP11190586 | 2011-11-24 | ||
| EP11190574 | 2011-11-24 | ||
| EP11190567 | 2011-11-24 | ||
| US201261718393P | 2012-10-25 | 2012-10-25 | |
| US201261718557P | 2012-10-25 | 2012-10-25 | |
| US61/718,557 | 2012-10-25 | ||
| US61/718,393 | 2012-10-25 | ||
| PCT/EP2012/073542 WO2013076289A1 (en) | 2011-11-24 | 2012-11-23 | Process for recycling a formaldehyde source during a polymerization process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015500894A JP2015500894A (ja) | 2015-01-08 |
| JP2015500894A5 true JP2015500894A5 (enExample) | 2016-01-14 |
| JP6144272B2 JP6144272B2 (ja) | 2017-06-07 |
Family
ID=47216340
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014542867A Expired - Fee Related JP6192651B2 (ja) | 2011-11-24 | 2012-11-23 | 環状アセタールの製造方法 |
| JP2014542866A Active JP6192650B2 (ja) | 2011-11-24 | 2012-11-23 | トリオキサンの製造方法 |
| JP2014542869A Active JP6192652B2 (ja) | 2011-11-24 | 2012-11-23 | 不均一反応系にて環状アセタールを製造する方法 |
| JP2014542868A Expired - Fee Related JP6144272B2 (ja) | 2011-11-24 | 2012-11-23 | 重合プロセスにおけるホルムアルデヒド源のリサイクル方法 |
| JP2014542870A Expired - Fee Related JP6192653B2 (ja) | 2011-11-24 | 2012-11-23 | 水性ホルムアルデヒド源からトリオキサンを製造する方法 |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014542867A Expired - Fee Related JP6192651B2 (ja) | 2011-11-24 | 2012-11-23 | 環状アセタールの製造方法 |
| JP2014542866A Active JP6192650B2 (ja) | 2011-11-24 | 2012-11-23 | トリオキサンの製造方法 |
| JP2014542869A Active JP6192652B2 (ja) | 2011-11-24 | 2012-11-23 | 不均一反応系にて環状アセタールを製造する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014542870A Expired - Fee Related JP6192653B2 (ja) | 2011-11-24 | 2012-11-23 | 水性ホルムアルデヒド源からトリオキサンを製造する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (8) | US9499512B2 (enExample) |
| EP (5) | EP2782907B8 (enExample) |
| JP (5) | JP6192651B2 (enExample) |
| KR (4) | KR101969615B1 (enExample) |
| CN (7) | CN106866615B (enExample) |
| WO (7) | WO2013076286A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013076286A1 (en) * | 2011-11-24 | 2013-05-30 | Ticona Gmbh | Process for the production of trioxane |
| CN105218513B (zh) * | 2014-05-29 | 2017-12-12 | 中国石油大学(北京) | 一种合成三聚甲醛的方法 |
| FR3024729B1 (fr) * | 2014-08-07 | 2018-09-07 | Arkema France | Procede de preparation du trioxane |
| CN104478848B (zh) * | 2015-01-09 | 2016-06-29 | 开封龙宇化工有限公司 | 一种三聚甲醛脱轻塔分离器加碱水洗装置及使用方法 |
| CN105175389B (zh) * | 2015-09-10 | 2018-09-07 | 中国石油大学(北京) | 一种利用酸和盐催化甲醛合成三聚甲醛的方法 |
| CN107474037A (zh) * | 2017-07-03 | 2017-12-15 | 湖北三里枫香科技有限公司 | 一种多级固定床型三聚甲醛生产工艺方法及制备装置 |
| US10829467B2 (en) * | 2018-03-29 | 2020-11-10 | Celanese Sales Germany Gmbh | Process for producing a cyclic acetal in a heterogeneous reaction system |
| FR3108909A1 (fr) * | 2020-04-07 | 2021-10-08 | Arkema Fance | Recyclage de polyacétal pour la production de polyoxyméthylènedialkyléthers |
| WO2021213663A1 (de) * | 2020-04-23 | 2021-10-28 | Wacker Chemie Ag | Verfahren zur herstellung von aldehyden aus 1,3,5-trioxanen |
| CN116323730A (zh) * | 2020-08-14 | 2023-06-23 | 国际人造丝公司 | 利用生物质来生产聚甲醛共聚物 |
| CN112724118B (zh) * | 2020-12-08 | 2023-02-28 | 中国石油大学(华东) | 一种石油基塑料pom的生物质醇解方法 |
| US20220380557A1 (en) * | 2021-05-20 | 2022-12-01 | Xerox Corporation | Polyoxymethylene microparticles and methods of production and use thereof |
| TW202413339A (zh) * | 2022-06-03 | 2024-04-01 | 日商三菱瓦斯化學股份有限公司 | 組成物、及使用其之三噁烷的製造方法 |
| US11643486B1 (en) | 2022-06-08 | 2023-05-09 | Arkema Inc. | Non-linear vinylidene fluoride copolymers |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL298169A (enExample) | 1961-08-25 | |||
| BE656705A (enExample) | 1963-12-05 | |||
| DE1493995A1 (de) | 1964-11-25 | 1969-08-07 | Meissner Fa Josef | Verfahren zum Beheizen einer Destilliereinrichtung bei der Gewinnung von Trioxan aus Formaldehyd |
| AT252913B (de) | 1964-12-29 | 1967-03-10 | Perstorp Aktiebolag | Verfahren zur Herstellung von Trioxan |
| US3457227A (en) | 1965-03-11 | 1969-07-22 | Continental Oil Co | Preparation of polyoxymethylene using metal acetylacetonate polymerization catalysts |
| US3471998A (en) | 1966-08-17 | 1969-10-14 | Asahi Chemical Ind | Process for purifying formaldehyde |
| US3506615A (en) | 1968-01-17 | 1970-04-14 | Celanese Corp | Polymerization of oxymethylene and methylene sulfide forming monomers by metal acetylacetonates |
| US3697546A (en) | 1970-01-14 | 1972-10-10 | Japan Gas Chemical Co | Method of producing trioxan |
| JPS4935839B2 (enExample) | 1971-10-19 | 1974-09-26 | ||
| IT1051890B (it) | 1975-12-23 | 1981-05-20 | Sir Soc Italiana Resine Spa | Procedimento migliorato per la stabilizzazione di omopolimmeri acetalici eterificati e di copolimeri acetalici |
| DE2827974C3 (de) | 1978-06-26 | 1980-12-11 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von 2,4,6-Trialkyl-l,3,5-trioxanen |
| DE2843468A1 (de) | 1978-10-05 | 1980-04-24 | Hoechst Ag | Verfahren zur gleichzeitigen herstellung von trioxan und cyclischen formalen |
| JPS56118079A (en) | 1980-02-22 | 1981-09-16 | Asahi Chem Ind Co Ltd | Synthesis of trioxane |
| US4358623A (en) | 1981-07-23 | 1982-11-09 | Celanese Corporation | Process for catalytically converting methanol to formaldehyde |
| US4420641A (en) | 1981-07-27 | 1983-12-13 | Celanese Corporation | Formaldehyde production |
| US4450301A (en) | 1982-10-21 | 1984-05-22 | Celanese Corporation | Process for converting methanol to formaldehyde |
| DE68914858T2 (de) | 1988-02-03 | 1994-08-11 | Asahi Chemical Ind | Verfahren zur Herstellung von Formaldehyd und dessen Derivaten. |
| GB2218089B (en) * | 1988-04-07 | 1991-11-06 | Asahi Chemical Ind | Process for producing high purity formaldehyde |
| DE3920811A1 (de) | 1989-06-24 | 1991-01-03 | Hoechst Ag | Verfahren zur herstellung von formaldehyd |
| DE4137846A1 (de) | 1991-11-16 | 1993-05-19 | Basf Ag | Verfahren zur herstellung von wasserfreiem und von verunreinigungen befreitem formaldehyd |
| DE59306392D1 (de) | 1992-12-31 | 1997-06-12 | Hoechst Ag | Verfahren zur Herstellung von Trioxan |
| JPH06228126A (ja) * | 1993-02-05 | 1994-08-16 | Asahi Chem Ind Co Ltd | トリオキサンの合成方法 |
| US5767294A (en) * | 1993-02-17 | 1998-06-16 | Hoechst Celanese Corporation | Process for the production of trioxane from formaldehyde |
| JP3304679B2 (ja) | 1995-04-21 | 2002-07-22 | ポリプラスチックス株式会社 | トリオキサンの製造方法 |
| US6388102B2 (en) * | 1997-06-02 | 2002-05-14 | Ticona Gmbh | Process for the preparation of trioxane and polyoxymethylene copolymers |
| DE19810087A1 (de) | 1998-03-10 | 1999-09-16 | Ticona Gmbh | Verfahren zur nicht oxidativen Herstellung von Formaldehyd aus Methanol |
| US6472566B2 (en) | 1998-03-31 | 2002-10-29 | Ticona Gmbh | Apparatus for the preparation of formaldehyde from methanol |
| US6362305B1 (en) | 1998-03-31 | 2002-03-26 | Ticona Gmbh | Method for producing formaldehyde from methanol |
| US6448448B1 (en) | 1998-03-31 | 2002-09-10 | Ticona Gmbh | Process for the non-oxidative preparation of formaldehyde from methanol |
| DE19822598A1 (de) | 1998-05-20 | 1999-11-25 | Degussa | Verfahren zur Herstellung von Formaldehyd II |
| DE19920830A1 (de) * | 1999-05-06 | 2000-11-09 | Ticona Gmbh | Trimerisierung von Formaldehyd in der Gasphase |
| DE10062814A1 (de) | 2000-12-15 | 2002-06-20 | Ticona Gmbh | Verfahren zur Entfernung von Methanol aus formaldeyhdhaltigen Lösungen |
| JP2002226426A (ja) * | 2001-02-02 | 2002-08-14 | Mitsubishi Gas Chem Co Inc | ジメチロールブタン酸の製造法 |
| US20030166972A1 (en) | 2002-02-20 | 2003-09-04 | Regents Of The University Of California Office Of Technology Licensing | Process for production of formaldehyde from dimethyl ether |
| DE10258663B4 (de) * | 2002-12-13 | 2005-07-28 | Ticona Gmbh | Verfahren zur Herstellung von Trioxan |
| DE10309288A1 (de) * | 2003-03-04 | 2004-09-16 | Basf Ag | Verfahren zur Bereitstellung hochkonzentrierten gasförmigen Formaldehyds |
| DE102005012480A1 (de) * | 2005-03-16 | 2006-09-21 | Basf Ag | Verfahren zur Entfernung von Restmonomeren aus Polyoxymethylenen |
| BRPI0615387A2 (pt) * | 2005-08-26 | 2016-09-13 | Basf Se | processo para preparar homopolímeros ou copolímeros de polioximetileno por homopolimerização ou copolimerização de trioxano ou adicionalmente de comonômeros adequados |
| JP2007230979A (ja) * | 2006-03-03 | 2007-09-13 | Showa Denko Kk | １，３−プロパンジオールの製造方法 |
| US20100004409A1 (en) | 2006-07-26 | 2010-01-07 | Basf Se | Method for producing polyoxymethylenes with certain deactivators |
| CA2673572A1 (en) | 2007-01-25 | 2008-07-31 | Basf Se | Removal of trioxane from a trioxane/formaldehyde/water mixture by means of pressure-swing rectification |
| US20100145079A1 (en) | 2007-03-30 | 2010-06-10 | Basf Se | Method for producing cyclic formaldehyde derivatives from polyoxy dialkyl ethers |
| CN101311154B (zh) | 2007-05-22 | 2010-08-11 | 富艺国际工程有限公司 | 使用离子液体合成三聚甲醛的方法 |
| CN101665409A (zh) | 2008-09-04 | 2010-03-10 | 中国科学院兰州化学物理研究所 | 离子液体催化合成1,3-二元醇或其环状缩醛的方法 |
| WO2013076286A1 (en) * | 2011-11-24 | 2013-05-30 | Ticona Gmbh | Process for the production of trioxane |
-
2012
- 2012-11-23 WO PCT/EP2012/073539 patent/WO2013076286A1/en not_active Ceased
- 2012-11-23 US US14/359,594 patent/US9499512B2/en active Active
- 2012-11-23 CN CN201710109742.1A patent/CN106866615B/zh active Active
- 2012-11-23 WO PCT/EP2012/073542 patent/WO2013076289A1/en not_active Ceased
- 2012-11-23 US US14/359,319 patent/US9604956B2/en active Active
- 2012-11-23 US US14/359,308 patent/US20140323686A1/en not_active Abandoned
- 2012-11-23 CN CN201280057948.XA patent/CN103958493B/zh not_active Expired - Fee Related
- 2012-11-23 KR KR1020147017191A patent/KR101969615B1/ko active Active
- 2012-11-23 WO PCT/EP2012/073543 patent/WO2013076290A1/en not_active Ceased
- 2012-11-23 KR KR1020147017187A patent/KR20140107309A/ko not_active Withdrawn
- 2012-11-23 JP JP2014542867A patent/JP6192651B2/ja not_active Expired - Fee Related
- 2012-11-23 US US14/359,333 patent/US9365537B2/en not_active Expired - Fee Related
- 2012-11-23 EP EP12788603.4A patent/EP2782907B8/en not_active Not-in-force
- 2012-11-23 JP JP2014542866A patent/JP6192650B2/ja active Active
- 2012-11-23 CN CN201280057571.8A patent/CN103958492A/zh active Pending
- 2012-11-23 EP EP12794929.5A patent/EP2782909A1/en not_active Withdrawn
- 2012-11-23 EP EP12788601.8A patent/EP2782906B1/en not_active Not-in-force
- 2012-11-23 KR KR1020147017142A patent/KR20140102243A/ko not_active Withdrawn
- 2012-11-23 US US14/359,223 patent/US9574061B2/en not_active Expired - Fee Related
- 2012-11-23 CN CN201711457383.5A patent/CN108164500B/zh active Active
- 2012-11-23 WO PCT/EP2012/073541 patent/WO2013076288A1/en not_active Ceased
- 2012-11-23 US US14/359,314 patent/US9469624B2/en not_active Expired - Fee Related
- 2012-11-23 US US14/359,203 patent/US9546148B2/en active Active
- 2012-11-23 JP JP2014542869A patent/JP6192652B2/ja active Active
- 2012-11-23 EP EP12788604.2A patent/EP2782908B1/en active Active
- 2012-11-23 CN CN201280057570.3A patent/CN104024240A/zh active Pending
- 2012-11-23 WO PCT/EP2012/073540 patent/WO2013076287A1/en not_active Ceased
- 2012-11-23 JP JP2014542868A patent/JP6144272B2/ja not_active Expired - Fee Related
- 2012-11-23 KR KR1020147017132A patent/KR20140102241A/ko not_active Ceased
- 2012-11-23 JP JP2014542870A patent/JP6192653B2/ja not_active Expired - Fee Related
- 2012-11-23 WO PCT/EP2012/073544 patent/WO2013076291A1/en not_active Ceased
- 2012-11-23 CN CN201280057582.6A patent/CN104105695A/zh active Pending
- 2012-11-23 EP EP12788600.0A patent/EP2782905B1/en active Active
- 2012-11-23 CN CN201280057572.2A patent/CN103946219B/zh not_active Expired - Fee Related
- 2012-11-23 WO PCT/EP2012/073545 patent/WO2013076292A1/en not_active Ceased
-
2016
- 2016-06-10 US US15/179,548 patent/US20160280882A1/en not_active Abandoned
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