CN114805035A - 一种4,4’-联苯二酚的纯化方法 - Google Patents
一种4,4’-联苯二酚的纯化方法 Download PDFInfo
- Publication number
- CN114805035A CN114805035A CN202210644379.4A CN202210644379A CN114805035A CN 114805035 A CN114805035 A CN 114805035A CN 202210644379 A CN202210644379 A CN 202210644379A CN 114805035 A CN114805035 A CN 114805035A
- Authority
- CN
- China
- Prior art keywords
- biphenol
- purifying
- activated carbon
- product
- crude
- 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
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 47
- 239000000047 product Substances 0.000 claims description 31
- 238000001914 filtration Methods 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 19
- 238000001816 cooling Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 238000004042 decolorization Methods 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 229920000106 Liquid crystal polymer Polymers 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 abstract description 8
- 238000000746 purification Methods 0.000 abstract description 7
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000012535 impurity Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000001788 irregular Effects 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- -1 -tert-butyl biphenyldiol Chemical compound 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N dihydroxy-phenylborane Natural products OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Images
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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
-
- 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
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210644379.4A CN114805035B (zh) | 2022-06-08 | 2022-06-08 | 一种4,4’-联苯二酚的纯化方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210644379.4A CN114805035B (zh) | 2022-06-08 | 2022-06-08 | 一种4,4’-联苯二酚的纯化方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN114805035A true CN114805035A (zh) | 2022-07-29 |
CN114805035B CN114805035B (zh) | 2023-03-24 |
Family
ID=82520304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210644379.4A Active CN114805035B (zh) | 2022-06-08 | 2022-06-08 | 一种4,4’-联苯二酚的纯化方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114805035B (zh) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01226841A (ja) * | 1988-03-04 | 1989-09-11 | Mitsui Petrochem Ind Ltd | p,p´‐ビフェノール類の精製方法 |
JPH0248543A (ja) * | 1988-08-09 | 1990-02-19 | Dainippon Ink & Chem Inc | P,p´−ビフェノールの精製方法 |
CN105111049A (zh) * | 2015-09-24 | 2015-12-02 | 中国中化股份有限公司 | 一种2,2’-二羟基联苯的制备方法 |
CN105330518A (zh) * | 2015-11-30 | 2016-02-17 | 江门市优巨新材料有限公司 | 一种高纯度联苯二酚类化合物工业化合成方法 |
CN112341316A (zh) * | 2020-10-23 | 2021-02-09 | 河北中化鑫宝化工科技有限公司 | 一种以氧芴馏分为原料制备2,2’-二羟基联苯的方法 |
CN113956135A (zh) * | 2021-11-15 | 2022-01-21 | 宁夏清研高分子新材料有限公司 | 一种高产率的4,4’联苯二酚的制备方法 |
CN114181052A (zh) * | 2021-12-20 | 2022-03-15 | 宁夏清研高分子新材料有限公司 | 一种高纯度4,4’-联苯二酚的制备方法 |
-
2022
- 2022-06-08 CN CN202210644379.4A patent/CN114805035B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01226841A (ja) * | 1988-03-04 | 1989-09-11 | Mitsui Petrochem Ind Ltd | p,p´‐ビフェノール類の精製方法 |
JPH0248543A (ja) * | 1988-08-09 | 1990-02-19 | Dainippon Ink & Chem Inc | P,p´−ビフェノールの精製方法 |
CN105111049A (zh) * | 2015-09-24 | 2015-12-02 | 中国中化股份有限公司 | 一种2,2’-二羟基联苯的制备方法 |
CN105330518A (zh) * | 2015-11-30 | 2016-02-17 | 江门市优巨新材料有限公司 | 一种高纯度联苯二酚类化合物工业化合成方法 |
CN112341316A (zh) * | 2020-10-23 | 2021-02-09 | 河北中化鑫宝化工科技有限公司 | 一种以氧芴馏分为原料制备2,2’-二羟基联苯的方法 |
CN113956135A (zh) * | 2021-11-15 | 2022-01-21 | 宁夏清研高分子新材料有限公司 | 一种高产率的4,4’联苯二酚的制备方法 |
CN114181052A (zh) * | 2021-12-20 | 2022-03-15 | 宁夏清研高分子新材料有限公司 | 一种高纯度4,4’-联苯二酚的制备方法 |
Non-Patent Citations (2)
Title |
---|
汤克勇等: "pH对活性炭吸附染料能力的影响", 《中国皮革》 * |
王运生等: "在活性炭脱色中pH值的影响研究", 《发酵科技通讯》 * |
Also Published As
Publication number | Publication date |
---|---|
CN114805035B (zh) | 2023-03-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109956983B (zh) | 三氯蔗糖-6-乙酯的提取方法 | |
CN110713474B (zh) | 一种精制呋喃二羧酸的方法 | |
CN111499529B (zh) | 一种紫外线吸收剂UVA Plus的合成方法 | |
CN111039777A (zh) | 产率高成本低的十二烷基二元羧酸精制提纯方法 | |
CN114805035B (zh) | 一种4,4’-联苯二酚的纯化方法 | |
CN112409201B (zh) | 2-羟基-5-[2-(4-(三氟甲基苯基)乙基氨基)]苯甲酸的制备方法 | |
US8252922B2 (en) | Method for crystallizing sucralose | |
JP2005029563A (ja) | スピログリコールの製造方法 | |
CN109503441B (zh) | 高含量半胱胺盐酸盐的制备方法 | |
CN115850061A (zh) | 一种联苯醚四甲酸的精制方法 | |
CN111116319B (zh) | 一种1,6-二羟基萘的合成精制方法 | |
JP2010184902A (ja) | イオン液体の精製方法および回収方法 | |
CN112645799B (zh) | 一种间苯二酚的后处理工艺 | |
CN1157383C (zh) | 4-苯基尿唑的制备方法 | |
JP5492497B2 (ja) | 無水糖アルコールの精製方法 | |
KR20030033958A (ko) | 고순도 나프탈렌디카복실산의 제조방법 | |
CN114315810B (zh) | 一种异氰尿酸三缩水甘油酯的纯化方法 | |
CN114478234B (zh) | 一种4-氯代邻苯二甲酸单钠盐粗品的精制方法 | |
CN114133318B (zh) | 一种降除丙泊酚产品中丙泊酚杂质o的方法 | |
CN113773223B (zh) | 沉淀法提纯2-氨基-4-乙酰氨基苯甲醚的方法 | |
CN113563416B (zh) | 一种二肽母液的处理方法及其在二肽的生产工艺中的应用 | |
CN115231992A (zh) | 一种(2-氯-5-碘苯基)(4-氟苯基)甲酮的制备方法 | |
CN115772067A (zh) | 一种高反反式特种氢化双酚a的提纯方法 | |
CN114437099A (zh) | 一种高纯度异山梨醇的制备方法 | |
CN117816164A (zh) | 一种复合催化剂及其在合成取代苯并咪唑衍生物中的应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20231208 Address after: No. 123 Bayiqiao Road, Xinqiao Street, Qianfeng District, Guang'an City, Sichuan Province, 638000 Patentee after: Sichuan Shengxiao Technology Co.,Ltd. Address before: 638500 No. 3, Shibin Road, Kuige street, economic and Technological Development Zone, Guang'an City, Sichuan Province Patentee before: Sichuan shengxiao Technology Co.,Ltd. Patentee before: Sichuan hasheng Technology Development Co.,Ltd. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A Purification Method for 4,4 '- Bisphenol Granted publication date: 20230324 Pledgee: Bank of China Guang'an Branch Pledgor: Sichuan Shengxiao Technology Co.,Ltd. Registration number: Y2024980003289 |