JPS647060B2 - - Google Patents
Info
- Publication number
- JPS647060B2 JPS647060B2 JP57021257A JP2125782A JPS647060B2 JP S647060 B2 JPS647060 B2 JP S647060B2 JP 57021257 A JP57021257 A JP 57021257A JP 2125782 A JP2125782 A JP 2125782A JP S647060 B2 JPS647060 B2 JP S647060B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydroquinone
- reaction
- phosphoric acid
- solvent
- 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.)
- Expired
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 48
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 42
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 20
- -1 aralkyl monosubstituted hydroquinone Chemical class 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 27
- 235000011007 phosphoric acid Nutrition 0.000 description 23
- 239000000047 product Substances 0.000 description 16
- 239000010410 layer Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 3
- VXQLTVHJJGSMKL-UHFFFAOYSA-N 2,5-bis(1-phenylethyl)benzene-1,4-diol Chemical compound C=1C(O)=C(C(C)C=2C=CC=CC=2)C=C(O)C=1C(C)C1=CC=CC=C1 VXQLTVHJJGSMKL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical group CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000012435 aralkylating agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- FITUHHPILMJZMP-UHFFFAOYSA-N styrene;sulfuric acid Chemical compound OS(O)(=O)=O.C=CC1=CC=CC=C1 FITUHHPILMJZMP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57021257A JPS58140035A (ja) | 1982-02-15 | 1982-02-15 | アラルキルモノ置換ヒドロキノンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57021257A JPS58140035A (ja) | 1982-02-15 | 1982-02-15 | アラルキルモノ置換ヒドロキノンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58140035A JPS58140035A (ja) | 1983-08-19 |
| JPS647060B2 true JPS647060B2 (pt) | 1989-02-07 |
Family
ID=12050029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57021257A Granted JPS58140035A (ja) | 1982-02-15 | 1982-02-15 | アラルキルモノ置換ヒドロキノンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58140035A (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1223392B (it) * | 1987-12-01 | 1990-09-19 | Montedison Spa | Procedimento per l'alchilazione di fenoli |
| EP0418278A1 (en) * | 1988-05-31 | 1991-03-27 | Eastman Kodak Company | Process for the preparation of (arylethyl)hydroquinones and diesters thereof |
| IT1217876B (it) * | 1988-06-21 | 1990-03-30 | Donegani Guido Ist | Procedimento per l'alchilazione di fenoli |
-
1982
- 1982-02-15 JP JP57021257A patent/JPS58140035A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58140035A (ja) | 1983-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3326986A (en) | Process for purifying 4, 4'-isopropylidenediphenol | |
| WO1999006418A1 (en) | Selective synthesis of organodiphosphite compounds | |
| JPS6146465B2 (pt) | ||
| JPH0193560A (ja) | ジアリールカーボネートの製造法 | |
| JPH0899983A (ja) | ６−オキソ−（６Ｈ）−ジベンズ−［ｃ，ｅ］［１，２］−オキサホスホリンを製造するための方法 | |
| JPS647060B2 (pt) | ||
| KR940005954B1 (ko) | 폴리아릴알칸 올리고머 조성물 및 그의 제조방법 | |
| JP3161669B2 (ja) | トリメリット酸エステル無水物類の製造方法 | |
| JPH029576B2 (pt) | ||
| US3004054A (en) | Process for the manufacture of mixed phosphorothioate esters | |
| JP2558497B2 (ja) | アルキルジハロゲノホスファンの製造法 | |
| JP3962467B2 (ja) | １，４−ジヒドロキシ−２−ナフトエ酸アリールエステル類の製造方法 | |
| JP2582881B2 (ja) | テトラブチルビフェノールの脱ブチル化方法 | |
| US3577482A (en) | Process for the preparation of thionophosphonates | |
| US3327026A (en) | Esterification of thionobenzene-phosphonyldichloride in the presence of 2-methyl-5-ethylpyridine | |
| EP0889040B1 (en) | Process for producing 2,4-oxazolidinedione | |
| US2857399A (en) | Process for preparing 4-phenyl-1, 2-dithiole-3-thione | |
| HU186934B (en) | Process for the production of o,s-dialkyl-phosphoro-amido-thioates | |
| JPH0853390A (ja) | ビス（ヒドロキシアリール）ペンタン酸類の製造方法 | |
| JPS59137431A (ja) | トリメチロ−ルヘプタンの製造方法 | |
| US7041853B2 (en) | Process for producing 4-bromothioanisole | |
| EP0075355A1 (en) | The preparation of derivatives of dichloroacetic acid esters | |
| JP2676908B2 (ja) | キシレンジクロライド類の製造法 | |
| US2759968A (en) | Method of preparing esters from chloretone | |
| JP2759087B2 (ja) | １，４―ジヒドロキシ―２―ナフトエ酸アリールエステルの精製方法 |