CN1323285A - 生产双(4－羟芳基)烷烃的方法 - Google Patents
生产双(4－羟芳基)烷烃的方法 Download PDFInfo
- Publication number
- CN1323285A CN1323285A CN99812257A CN99812257A CN1323285A CN 1323285 A CN1323285 A CN 1323285A CN 99812257 A CN99812257 A CN 99812257A CN 99812257 A CN99812257 A CN 99812257A CN 1323285 A CN1323285 A CN 1323285A
- Authority
- CN
- China
- Prior art keywords
- hydroxyaryl
- aromatic hydroxy
- hydroxy compound
- alkane
- inert gas
- 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
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- -1 aromatic hydroxy compounds Chemical class 0.000 claims abstract description 27
- 239000011261 inert gas Substances 0.000 claims abstract description 13
- 238000009833 condensation Methods 0.000 claims abstract description 6
- 230000005494 condensation Effects 0.000 claims abstract description 6
- 239000007789 gas Substances 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 238000001179 sorption measurement Methods 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 239000002609 medium Substances 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000000155 melt Substances 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 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
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
- DYQPZDLXQPYGSU-UHFFFAOYSA-N 2-cyclopentyl-6-methylphenol Chemical compound CC1=CC=CC(C2CCCC2)=C1O DYQPZDLXQPYGSU-UHFFFAOYSA-N 0.000 description 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种利用双(4－羟芳基)烷烃与芳香族羟基化合物的加成物来生产双(4－羟芳基)烷烃的方法,其中包括:a)将惰性气体通过150℃至230℃的双(4－羟芳基)烷烃与芳香族羟基化合物加成物的熔融体,其中,惰性气体流从熔融体中除去了芳香族羟基化合物;b)通过冷凝去除惰性气体流中的芳香族羟基化合物;c)将惰性气体流精制、压缩并循环到步骤a)。
Description
本发明涉及一种利用由芳香族羟基化合物与酮进行酸催化反应制得的双(4-羟芳基)烷烃与芳香族羟基化合物的加成物来生产双(4-羟芳基)烷烃的方法。
例如，利用芳香族羟基化合物与酮的酸催化反应来制备双(4-羟芳基)烷烃在US-A 2 775 620或EP-A 342 758中已有报道。通常，用作起始物料的双(4-羟芳基)烷烃和芳香族羟基化合物的加成物作为中间产物获得，随后通过蒸馏方式将其从芳香族羟基化合物中分离出来。大规模工业生产的最重要的例子是双酚A的生产，在其生产过程中，得到的双酚A(BPA)和酚的加成物作为中间产物获得，即使在纯化以后，例如重结晶以后，由于采用了酸催化生产路线，此加成物中仍含有痕量的酸(约5至10×10-6mol酸/mol双酚A)。在与温度升高有关的酚从双酚A的分离过程中，这些痕量的酸使双酚A发生部分分解反应，导致副产物的形成。这些分解反应的结果降低了双酚的纯度和颜色品质。这也对由双酚制得的产品例如环氧树脂、聚酯、聚酯碳酸酯和聚碳酸酯的品质产生负面影响，其结果表现在颜色问题、光通过透明产品的传导性差或由这些最终产品制得的模制品的表面有针孔。同样的现象也发生在其它双(4-羟芳基)烷烃的生产方法中。
从双(4-羟芳基)烷烃中分离芳香族羟基化合物，也称为“汽提”，在文献中已经公开，例如在欧洲专利EP-A 343 349中已有描述。此文献中芳香族羟基化合物从双(4-羟芳基)烷烃中的分离是在轻微减压下在温度为160℃至200℃的范围内的填料塔中使用蒸汽来实现的。在芳香族羟基化合物从双(4-羟芳基)烷烃的分离过程中发生热分解反应也是公知的，例如美国专利US-A 5,091,159所报道的。
现在，已经发现了一种在芳香族羟基化合物(单酚)从双(4-羟芳基)烷烃的汽提过程中能够强烈抑制分解反应的方法。在此过程中用惰性气体将单酚从双(4-羟芳基)烷烃中分离出来，在单酚冷凝之后将循环的惰性气体进行精制，因此，能够避免双(4-羟芳基)烷烃降解。
可用于本发明所述方法的双(4-羟芳基)烷烃和芳香族羟基化合物的加成物可以通过其中对位没有被取代并且不包含诸如氰基、羧基或硝基基团的二级取代基的芳香族羟基化合物与羰基上含有至少一个脂肪基团的酮反应制得，其中芳香族羟基化合物的例子有苯酚、邻-和间-甲酚、2,6-二甲酚、邻叔丁基苯酚、2-甲基-6-叔丁基苯酚、邻环己基苯酚、邻苯基苯酚、邻异丙基苯酚、2-甲基-6-环戊基苯酚、邻-和间-氯苯酚和2,3,6-三甲基苯酚，优选为苯酚、邻-和间-甲酚、2,6-二甲酚、邻叔丁基苯酚和邻苯基苯酚，特别优选为苯酚；而酮的例子有丙酮、甲基乙基酮、甲基丙基酮、甲基异丙基酮、二乙基酮、苯乙酮、环己酮、环戊酮，以及甲基-、二甲基-和三甲基-环己酮，其也可以含有偕甲基基团，如3,3-二甲基-5-甲基环己酮(hydroisophorone)，优选为丙酮、苯乙酮、环己酮及其含有甲基基团的同系物，尤其优选为丙酮。双酚A与苯酚的加成物作为优选使用的起始物料。
因此，本发明涉及一种利用双(4-羟芳基)烷烃与芳香族羟基化合物的加成物来生产双(4-羟芳基)烷烃的方法，其中包括：
a)将惰性气体通过150℃至230℃的双(4-羟芳基)烷烃与芳香族羟基化合物加成物的熔融体，其中，惰性气体流从熔融体中除去了芳香族羟基化合物；
b)通过冷凝去除惰性气体流中的芳香族羟基化合物；
c)将惰性气体流精制、压缩并循环到步骤a)。
从由双(4-羟芳基)烷烃与芳香族羟基化合物的加成物的熔融体中制得的双(4-羟芳基)烷烃中分离单酚的过程是在150℃至230℃温度范围内进行的，优选为170℃至210℃温度范围，其中通过引入惰性气体(如氮气)来排出单酚。气体与加成产物的比率优选为约10m3至1000m3/吨加成产物。可任选地通过降低单酚分离所使用的处理单元中的压力来促进汽提，但是汽提优选在常压下进行。利用惰性气体进行的单酚的汽提是在公知设备中进行的，例如在填料、溢流塔中。单酚可以在惰性气体循环系统中被去除，例如通过换热器冷凝。
再循环的惰性气体的精制可以利用使其通过固定床吸附剂(活性炭、分子筛等等)来完成，或者在一个优选的实施方案中，通过充分地洗涤惰性气体来完成。例如，此洗涤步骤可以在气体洗涤器中完成。在一个优选的实施方案中，在循环流动的惰性气体在压缩机中的压缩过程中，所使用的密封液体被作为洗涤介质。
弱碱性水溶液被用作洗涤介质。所使用的水溶液的pH值应该在7至12范围内，优选为7.5至11，最优选为8至10。所有具有碱性作用的物质都可以被用来制备此种水溶液。优选使用碱金属和碱土金属的氢氧化物。在一个优选的实施方案中，对洗涤前后的pH值进行监控，以防止在循环气体的精制过程中过量加入和加入不足。此外，惰性气体流随后可以被送到二级洗涤步骤。二级洗涤介质pH值优选为中性。
根据本发明方法制得的双(4-羟芳基)烷烃以其非常好的固有颜色和高纯度而著称。特别是，其包含低浓度的芳香族羟基化合物(＜100ppm，优选为＜50ppm)和分解产物(如异丙烯基苯酚、二聚异丙烯基苯酚)。
具有低级固有颜色的聚合物诸如聚碳酸脂或环氧化物可以从根据本发明方法所得的双(4-羟芳基)烷烃来制得。
实施例
实施例1
将BPA与苯酚(60/40％重量)的熔融混合物以1吨/小时的速率被送到解吸塔中。使225m3/小时的氮气(作为循环流)连续通过解吸塔。苯酚被氮气吸收，随后通过换热器冷凝。再将氮气送到用很稀的NaOH溶液(pH=10)作为密封液体的压缩机中，氮气在压缩机中被压缩。然后，将氮气送到利用去离子水来工作的气体洗涤器中。用此方法处理的氮气随后再用于汽提苯酚的解吸塔中。得到一种低苯酚含量(苯酚量为40ppm)、颜色明亮的BPA熔融体，该熔融体哈森色度为8。对比实施例1
除了氮气的洗涤被完全省略之外，其它步骤同实施例1。得到的BPA的哈森色度为17。BPA中苯酚的含量为90ppm，这表明发生了分解。
对比实施例2
除了用中性去离子水(pH=6.9)洗涤氮气之外，其它步骤同实施例1。得到的BPA的哈森色度为14。BPA中苯酚的含量为75ppm，这再次表明发生了分解。
对比实施例3
除了用稀NaOH(pH=13)溶液洗涤氮气之外，其它步骤同实施例1。得到的BPA的哈森色度为12。BPA中苯酚的含量为60ppm，这仍表明发生了分解。
Claims (7)
1．一种从双(4-羟芳基)烷烃与芳香族羟基化合物的加成物来生产双(4-羟芳基)烷烃的方法，其中包括：
a)将惰性气体通过150℃至230℃的双(4-羟芳基)烷烃与芳香族羟基化合物加成物的熔融体，其中，惰性气体流从熔融体中除去了芳香族羟基化合物；
b)通过冷凝去除惰性气体流中的芳香族羟基化合物；
c)将惰性气体精制、压缩并循环到步骤a)。
2．根据权利要求1所述的方法，其特征在于：惰性气体流的精制是通过用pH值在7至12范围内的水性介质洗涤而完成的。
3．根据权利要求2所述的方法，其特征在于：将用于惰性气体压缩的压缩机的密封液体作为洗涤介质。
4．根据权利要求2或3所述的方法，其特征在于：在碱洗涤后和在将其循环回步骤a)之前，使惰性气体流经受一个利用中性水性介质进行的二级洗涤步骤。
5．根据权利要求1所述的方法，其特征在于：惰性气体流的精制是通过使其流过固定床吸附剂来完成的。
6．根据权利要求5所述的方法，其特征在于：用活性炭或者分子筛作为固定床吸附剂。
7．根据权利要求1所述的方法可制得的含有芳香族羟基化合物浓度＜50ppm的双(4-羟基)烷烃。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19848026.1 | 1998-10-17 | ||
| DE19848026A DE19848026A1 (de) | 1998-10-17 | 1998-10-17 | Verfahren zur Herstellung von Bis(4-hydroxyaryl)alkanen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1323285A true CN1323285A (zh) | 2001-11-21 |
| CN1173911C CN1173911C (zh) | 2004-11-03 |
Family
ID=7884875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998122572A Expired - Fee Related CN1173911C (zh) | 1998-10-17 | 1999-10-05 | 生产双(4-羟芳基)烷烃的方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6384288B1 (zh) |
| EP (1) | EP1121339B1 (zh) |
| JP (1) | JP2002527497A (zh) |
| KR (1) | KR100608922B1 (zh) |
| CN (1) | CN1173911C (zh) |
| AU (1) | AU6089399A (zh) |
| BR (1) | BR9914607A (zh) |
| DE (2) | DE19848026A1 (zh) |
| ES (1) | ES2190253T3 (zh) |
| HK (1) | HK1042080A1 (zh) |
| ID (1) | ID29771A (zh) |
| MD (1) | MD2705B2 (zh) |
| TW (1) | TW517046B (zh) |
| WO (1) | WO2000023410A1 (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3340510B2 (ja) * | 1993-05-19 | 2002-11-05 | 日本パイオニクス株式会社 | 有害ガスの浄化方法 |
| DE19961566A1 (de) * | 1999-12-20 | 2001-06-21 | Bayer Ag | Bis(4-hydroxyaryl)alkane |
| US6703530B2 (en) | 2002-02-28 | 2004-03-09 | General Electric Company | Chemical reactor system and process |
| US7365116B2 (en) * | 2003-12-03 | 2008-04-29 | E. I. Du Pont De Nemours And Company | Articles of manufacture comprising stiff and resilient ethylene copolymer compositions |
| SG10201900535UA (en) | 2003-12-23 | 2019-02-27 | Genentech Inc | Novel anti-il 13 antibodies and uses thereof |
| DE102004048096A1 (de) * | 2004-09-30 | 2006-04-27 | Forschungszentrum Jülich GmbH | Verfahren zur Herstellung einer verspannten Schicht auf einem Substrat und Schichtstruktur |
| DE102005025788A1 (de) * | 2005-06-04 | 2006-12-07 | Bayer Materialscience Ag | Verfahren zur Herstellung von hochreinem Bisphenol A |
| US7754837B1 (en) | 2007-03-09 | 2010-07-13 | Clemson University Research Foundation | Flourinated aryl ether polymers exhibiting dual fluoroolefin functionality and methods of forming same |
| DE102007026548A1 (de) | 2007-06-08 | 2008-12-18 | Bayer Materialscience Ag | Vermeidung von Feststoffablagerungen in Tropfenabscheidern durch Eindüsung von geeigneten Flüssigkeiten |
| WO2015038888A1 (en) | 2013-09-13 | 2015-03-19 | Genentech, Inc. | Methods and compositions comprising purified recombinant polypeptides |
| RU2016107435A (ru) | 2013-09-13 | 2017-10-18 | Дженентек, Инк. | Композиции и способы обнаружения и количественного определения белка клеток-хозяев в клеточных линиях и рекомбинантные полипептидные продукты |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2775620A (en) * | 1954-07-12 | 1956-12-25 | Shell Dev | Production of bis (hydroxyaryl) substituted compounds |
| US4931146A (en) | 1988-04-05 | 1990-06-05 | Mitsui Toatsu Chemicals, Inc. | Process for obtaining high-purity bisphenol A |
| US4859803A (en) | 1988-05-16 | 1989-08-22 | Shell Oil Company | Preparation of bisphenols |
| US5091159A (en) | 1991-06-10 | 1992-02-25 | Nalco Chemical Company | Use of dextran as a filtration aid for thickener overflow filtration in Kelly filters in the Bayer process |
| CN1050828C (zh) * | 1993-02-16 | 2000-03-29 | 中国石油化工总公司 | 制备高品位聚碳酸脂级双酚a的脱酚新方法 |
| CN1080914A (zh) * | 1993-02-17 | 1994-01-19 | 中国石油化工总公司 | 一种2,2-二(4-羟基苯基)丙烷的制造方法 |
-
1998
- 1998-10-17 DE DE19848026A patent/DE19848026A1/de not_active Ceased
-
1999
- 1999-10-01 TW TW088116896A patent/TW517046B/zh not_active IP Right Cessation
- 1999-10-05 BR BR9914607-0A patent/BR9914607A/pt not_active IP Right Cessation
- 1999-10-05 CN CNB998122572A patent/CN1173911C/zh not_active Expired - Fee Related
- 1999-10-05 JP JP2000577138A patent/JP2002527497A/ja active Pending
- 1999-10-05 WO PCT/EP1999/007358 patent/WO2000023410A1/de active IP Right Grant
- 1999-10-05 MD MDA20010161A patent/MD2705B2/ro unknown
- 1999-10-05 DE DE59904188T patent/DE59904188D1/de not_active Expired - Lifetime
- 1999-10-05 ES ES99947458T patent/ES2190253T3/es not_active Expired - Lifetime
- 1999-10-05 KR KR1020017004787A patent/KR100608922B1/ko not_active IP Right Cessation
- 1999-10-05 US US09/807,645 patent/US6384288B1/en not_active Expired - Lifetime
- 1999-10-05 ID IDW20010848A patent/ID29771A/id unknown
- 1999-10-05 EP EP99947458A patent/EP1121339B1/de not_active Expired - Lifetime
- 1999-10-05 AU AU60893/99A patent/AU6089399A/en not_active Abandoned
-
2002
- 2002-01-03 US US10/037,995 patent/US20020055661A1/en not_active Abandoned
- 2002-05-15 HK HK02103685.2A patent/HK1042080A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ID29771A (id) | 2001-10-11 |
| US20020055661A1 (en) | 2002-05-09 |
| MD2705B2 (ro) | 2005-02-28 |
| US6384288B1 (en) | 2002-05-07 |
| EP1121339B1 (de) | 2003-01-29 |
| BR9914607A (pt) | 2001-07-03 |
| DE59904188D1 (de) | 2003-03-06 |
| MD20010161A (en) | 2001-09-30 |
| DE19848026A1 (de) | 2000-04-20 |
| TW517046B (en) | 2003-01-11 |
| KR100608922B1 (ko) | 2006-08-04 |
| JP2002527497A (ja) | 2002-08-27 |
| HK1042080A1 (zh) | 2002-08-02 |
| WO2000023410A1 (de) | 2000-04-27 |
| AU6089399A (en) | 2000-05-08 |
| EP1121339A1 (de) | 2001-08-08 |
| CN1173911C (zh) | 2004-11-03 |
| KR20010080188A (ko) | 2001-08-22 |
| ES2190253T3 (es) | 2003-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1173911C (zh) | 生产双(4-羟芳基)烷烃的方法 | |
| US5198591A (en) | Method to manufacture bisphenol a | |
| JP2862796B2 (ja) | ジアリールカーボネートの精製法 | |
| EP0522700A2 (en) | Process for the production of crystalline adduct of bisphenol A and phenol and apparatus therefor | |
| EP0558214A1 (en) | Process for therecovery of bisphenol-A bycrystallization | |
| JP2002338679A (ja) | ポリカーボネートの製造方法 | |
| JPH07258131A (ja) | 高純度ビスフエノールａの連続製造方法 | |
| CN1100710A (zh) | 2,2-双(4-羧基苯基)丙烷的生产方法 | |
| EP0459572A2 (en) | Process for purifying phenol | |
| US6414198B1 (en) | Method for producing bisphenol-A | |
| DE4326906C1 (de) | Verfahren zum chemischen Recycling von Polycarbonat | |
| EP0757030B1 (en) | Process for purifying diaryl carbonates | |
| EP0782978B1 (en) | Method for preparing and purifying 1,1,1-tris(4-hydroxyphenyl)ethane | |
| JPS6114227A (ja) | ポリカ−ボネ−ト樹脂の製法 | |
| KR100189205B1 (ko) | 비스페놀a. 페놀 결정 부가물의 정제방법, 이 결정 부가물의 제조방법과 그를 위한 정석 장치 및 비스페놀 a 의 제조방법 | |
| EP0326320A1 (en) | Preparation of 4,4'-dihydroxydiphenyl sulphone | |
| JP2962441B2 (ja) | 着色性の低いビスフェノールａの製造方法 | |
| US5994565A (en) | Process for producing purified ε-caprolactone | |
| JPS59163366A (ja) | カプロラクタムの精製方法 | |
| MXPA01003769A (en) | Method for the production of bis(4-hydroxyaryl)alkanes | |
| KR100190335B1 (ko) | 비스페놀a.페놀결정부가물의정제방법,이결정부가물의제조방법과그를위한정석장치및비스페놀a의제조방법 | |
| JP2000007681A (ja) | スピログリコールの製造方法 | |
| CN1286676A (zh) | 生产山梨酸的方法 | |
| JPH03258733A (ja) | α―メチルスチレンの精製方法 | |
| MXPA01006494A (en) | Method for producing bisphenol-a |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1042080 Country of ref document: HK |
|
| ASS | Succession or assignment of patent right |
Owner name: CARCOUSTICS TECHCONSULT GMBH Free format text: FORMER OWNER: BAYER AKTIENGESELLSCHAFT Effective date: 20120802 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20120802 Address after: Germany Leverkusen Patentee after: Carcoustics Techconsult GmbH Address before: Germany Leverkusen Patentee before: Bayer Aktiengesellschaft |
|
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20011121 Assignee: Bayer Material Science (China) Co., Ltd. Assignor: Carcoustics Techconsult GmbH Contract record no.: 2012990000854 Denomination of invention: The production of double (4- hydroxy aryl alkane) method Granted publication date: 20041103 License type: Common License Record date: 20121128 |
|
| LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20041103 Termination date: 20151005 |
|
| EXPY | Termination of patent right or utility model |