CA1263403A - Methode de preparation d'un ester derive d'un phenol dihydroxyle - Google Patents

Methode de preparation d'un ester derive d'un phenol dihydroxyle

Info

Publication number: CA1263403A
Authority: CA; Canada
Prior art keywords: dihydric phenol; carbon atoms; preparing; adsorbent; acid anhydride
Prior art date: 1984-09-18
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.): Expired

Application number

CA000490385A

Other languages

English (en)

Inventor

Benito See

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BP Corp North America Inc

Original Assignee

BP Corp North America Inc

Priority date (The priority date 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 date listed.)

1984-09-18

Filing date

1985-09-10

Publication date

1989-11-28

1985-09-10 Application filed by BP Corp North America Inc filed Critical BP Corp North America Inc

1989-11-28 Application granted granted Critical

1989-11-28 Publication of CA1263403A publication Critical patent/CA1263403A/fr

Status Expired legal-status Critical Current

Links

ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 26
150000002148 esters Chemical class 0.000 title claims abstract description 10
238000004519 manufacturing process Methods 0.000 title claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 24
239000003463 adsorbent Substances 0.000 claims abstract description 20
150000008065 acid anhydrides Chemical class 0.000 claims abstract description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
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 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
229940106691 bisphenol a Drugs 0.000 claims description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
239000002808 molecular sieve Substances 0.000 claims description 5
239000000741 silica gel Substances 0.000 claims description 5
229910002027 silica gel Inorganic materials 0.000 claims description 5
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 5
AREMQPPGVQNRIE-UHFFFAOYSA-N acetic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(O)=O.CC(O)=O.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 AREMQPPGVQNRIE-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000002993 cycloalkylene group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
229930195734 saturated hydrocarbon Natural products 0.000 claims 2
241001550224 Apha Species 0.000 description 12
239000002904 solvent Substances 0.000 description 10
150000005690 diesters Chemical class 0.000 description 8
239000003610 charcoal Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
239000000178 monomer Substances 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
229920001230 polyarylate Polymers 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000000376 reactant Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
RKSBPFMNOJWYSB-UHFFFAOYSA-N 3,3-Bis(4-hydroxyphenyl)pentane Chemical compound C=1C=C(O)C=CC=1C(CC)(CC)C1=CC=C(O)C=C1 RKSBPFMNOJWYSB-UHFFFAOYSA-N 0.000 description 1
RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
XDGXPHFWSPGAIB-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)ethyl]-2-methylphenol Chemical compound C=1C=C(O)C(C)=CC=1C(C)C1=CC=C(O)C(C)=C1 XDGXPHFWSPGAIB-UHFFFAOYSA-N 0.000 description 1
KCAPNGLKHXOABM-UHFFFAOYSA-N 4-[2-(4-hydroxy-2-propan-2-ylphenyl)propan-2-yl]-3-propan-2-ylphenol Chemical compound CC(C)C1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1C(C)C KCAPNGLKHXOABM-UHFFFAOYSA-N 0.000 description 1
ZZXOXJAAKGCFNH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)-1,2-diphenylpropyl]phenol Chemical compound C=1C=CC=CC=1C(C=1C=CC(O)=CC=1)(C)C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 ZZXOXJAAKGCFNH-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
206010042618 Surgical procedure repeated Diseases 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
-1 alumino silicates Chemical compound 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229920006258 high performance thermoplastic Polymers 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002531 isophthalic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003504 terephthalic acids Chemical class 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyesters Or Polycarbonates (AREA)

CA000490385A 1984-09-18 1985-09-10 Methode de preparation d'un ester derive d'un phenol dihydroxyle Expired CA1263403A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US65180784A	1984-09-18	1984-09-18
US651,807		1984-09-18

Publications (1)

Publication Number	Publication Date
CA1263403A true CA1263403A (fr)	1989-11-28

Family

ID=24614302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000490385A Expired CA1263403A (fr)	1984-09-18	1985-09-10	Methode de preparation d'un ester derive d'un phenol dihydroxyle

Country Status (2)

Country	Link
JP (1)	JPS6176443A (fr)
CA (1)	CA1263403A (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51118715A (en) *	1975-04-11	1976-10-18	Konsutanchiinobitsuchi Borisu	Method of producing ester of glycerine * polyglycerine and monobasic aliphatic acid having five to nine carbon atoms
US4439586A (en) *	1982-06-30	1984-03-27	Union Carbide Corporation	Process for preparing polyarylates

1985
- 1985-09-10 CA CA000490385A patent/CA1263403A/fr not_active Expired
- 1985-09-17 JP JP20360985A patent/JPS6176443A/ja active Pending

Also Published As

Publication number	Publication date
JPS6176443A (ja)	1986-04-18

Legal Events

Date	Code	Title	Description
1993-05-29	MKLA	Lapsed

Publication	Publication Date	Title
US4439586A (en)	1984-03-27	Process for preparing polyarylates
TW575597B (en)	2004-02-11	Process for producing polytrimethylene terephthalate
US5136018A (en)	1992-08-04	Macrocyclic polyarylate compositions of decreased crystallinity
US4613678A (en)	1986-09-23	Esterification of aromatic dicarboxylic acids with cyclic alkylene carbonates
KR100798242B1 (ko)	2008-01-24	고리형 에스테르 올리고머의 제조
CA1198446A (fr)	1985-12-24	Preparation d'esters diaryliques d'acides dicarboxyliques
US5969086A (en)	1999-10-19	Quaternary bisphenolates, methods for their preparation, and uses thereof
CA1263403A (fr)	1989-11-28	Methode de preparation d'un ester derive d'un phenol dihydroxyle
EP0019483A1 (fr)	1980-11-26	Procédé de préparation d'esters biphényltétracarboxyliques
US4855484A (en)	1989-08-08	Process for the preparation of 4-hydroxyphenyl 4-hydroxybenzoate and the use thereof
US4612360A (en)	1986-09-16	Melt polymerization process for preparing polyarylates
US5079335A (en)	1992-01-07	Process for preparing a color-improved thermoplastic polyarylate polymer
EP0044510B1 (fr)	1984-03-07	Procédé pour la préparation d'esters diaryliques
JP4053876B2 (ja)	2008-02-27	フェノール系化合物、該化合物から得られるポリマー並びに方法
US4533720A (en)	1985-08-06	Polyarylate formation by ester interchange reaction using γ- gamma lactones as diluent
US4958000A (en)	1990-09-18	Process for preparing polyarylates
JPH06239999A (ja)	1994-08-30	ポリエーテルスルホンを含むエステルの製造方法
US4803295A (en)	1989-02-07	Purification of diphenyl phthalates
JP2003292598A (ja)	2003-10-15	ポリエステル
US4647649A (en)	1987-03-03	Method of producing aromatic polyesters
JPH11228577A (ja)	1999-08-24	高純度スピログリコールの製造方法
JPS6336338B2 (fr)	1988-07-20
US4520168A (en)	1985-05-28	Color improved polyarylate
JPH05262864A (ja)	1993-10-12	芳香族ポリエステルの製造法
EP0044509B1 (fr)	1984-06-06	Procédé de préparation de téréphtalate de diphényle et d'isophtalate de diphényle