JPS63209749A - Reaction method using visco-elastic body - Google Patents
Reaction method using visco-elastic bodyInfo
- Publication number
- JPS63209749A JPS63209749A JP62042040A JP4204087A JPS63209749A JP S63209749 A JPS63209749 A JP S63209749A JP 62042040 A JP62042040 A JP 62042040A JP 4204087 A JP4204087 A JP 4204087A JP S63209749 A JPS63209749 A JP S63209749A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- active groups
- visco
- elastic body
- acidic
- 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
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims description 15
- 230000002378 acidificating effect Effects 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 230000003197 catalytic effect Effects 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims description 13
- 239000003190 viscoelastic substance Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 9
- 238000004898 kneading Methods 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 7
- 238000005260 corrosion Methods 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract description 4
- 238000010008 shearing Methods 0.000 abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 3
- 125000005586 carbonic acid group Chemical group 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 description 17
- 230000007062 hydrolysis Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000010426 asphalt Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 8
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 8
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 239000003350 kerosene Substances 0.000 description 6
- 241000705989 Tetrax Species 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- 238000006277 sulfonation reaction Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 3
- 229960001826 dimethylphthalate Drugs 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000011294 coal tar pitch Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- WOTYBMQPNCOMDB-UHFFFAOYSA-N dimethyl benzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC.COC(=O)C1=CC=CC=C1C(=O)OC WOTYBMQPNCOMDB-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- -1 hydrogen ions Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IVECIWLVOYDMRU-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O.COC(C)=O IVECIWLVOYDMRU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011271 tar pitch Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940006076 viscoelastic substance Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
- B01J19/002—Avoiding undesirable reactions or side-effects, e.g. avoiding explosions, or improving the yield by suppressing side-reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は粘弾性体を用いる反応方法に関するものである
。更に詳しくは、酸性活性基を有し、かつ変換対象物質
を含む液体に不溶性の粘弾性体を、高せん断力のかかる
条件下で曳糸性を示す状態に保ち、これに、前記酸性活
性基で反応変換される物質を含む含水液体を添加混練す
ることを特徴とする反応方法に関するものである。すな
わち、粘弾性体に含まれる酸性活性基の持つ酸触媒機能
を利用する新規な反応方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a reaction method using a viscoelastic body. More specifically, a viscoelastic body having an acidic active group and insoluble in a liquid containing a substance to be converted is maintained in a state exhibiting stringiness under conditions of high shear force, and then the acidic active group is This invention relates to a reaction method characterized by adding and kneading a water-containing liquid containing a substance to be reacted and converted. That is, the present invention relates to a novel reaction method that utilizes the acid catalytic function of acidic active groups contained in a viscoelastic body.
［従来の技術とその問題点コ
従来から、酸性活性を利用した反応方法は、化学工業上
広く行なわれてきた。例えば、反応触媒として、塩酸や
硫酸などの無機酸や、スルホン酸等の有機酸などの強酸
の他に、弱酸触媒としてカルボン酸などが使用されてき
た。しかし、反応活性を示す触媒自体が酸性物質である
ため、装置の腐食や保守などに問題があった。[Prior art and its problems] Conventionally, reaction methods utilizing acidic activity have been widely used in the chemical industry. For example, as reaction catalysts, in addition to strong acids such as inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as sulfonic acids, carboxylic acids and the like have been used as weak acid catalysts. However, since the catalyst itself that exhibits reaction activity is an acidic substance, there were problems with equipment corrosion and maintenance.
酸性物質の代わりに、いわゆる酸性イオン交換樹脂も、
それが同時に酸触媒機能を有するときは固体酸触媒とし
て用いられる。ここでいう酸性イオン交換樹脂とは、一
般的にスチレンジビニルベンゼン共重合体にスルホン基
を導入したものや、スチレンおよびジビニルベンゼンと
共にアクリル酸やメタクリル酸を共重合してカルボン酸
基を導入したものが例示される。これらの従来のイオン
交換樹脂の多くは何れも固体物質であり、反応触媒とし
て使用するために、重合方法を種々工夫し多孔質にする
ことによって、酸性活性基と反応対象物との接触の機会
を増加させ、反応効率を高めて使用されている。しかし
この場合、樹脂の細孔へ不純物か徐々に蓄積して、活性
中心である触媒活性基が反応物と接触し難くなることは
避けられない。固体樹脂の場合、反応効率や反応速度を
決定する主要な因子は固液接触の効率であるため、使用
形態が限定されるなどの問題点があった。Instead of acidic substances, so-called acidic ion exchange resins can also be used.
When it also has an acid catalytic function, it is used as a solid acid catalyst. The acidic ion-exchange resins mentioned here are generally those in which sulfone groups have been introduced into a styrene divinylbenzene copolymer, or those in which carboxylic acid groups have been introduced by copolymerizing acrylic acid or methacrylic acid with styrene and divinylbenzene. is exemplified. Most of these conventional ion exchange resins are solid substances, and in order to use them as reaction catalysts, various polymerization methods are used to make them porous, which increases the chances of contact between the acidic active groups and the reaction target. It is used to increase reaction efficiency. However, in this case, it is inevitable that impurities will gradually accumulate in the pores of the resin, making it difficult for the catalytic active group, which is the active center, to come into contact with the reactant. In the case of solid resins, the main factor that determines reaction efficiency and reaction rate is the efficiency of solid-liquid contact, so there have been problems such as limited usage forms.
また、イオン交換樹脂中の酸性活性基からの水素イオン
の遊離を助け、反応効率を改善するために、ナトリウム
、カリウム、マグネシウム、カルシウムなどの少量の金
属イオンを反応系に添加することもなされているが、酸
性活性基それ自体は徐々に中和され賦活の必要性がある
。In addition, small amounts of metal ions such as sodium, potassium, magnesium, and calcium have also been added to the reaction system to help liberate hydrogen ions from the acidic active groups in the ion exchange resin and improve reaction efficiency. However, the acidic active group itself is gradually neutralized and needs to be activated.
［問題点を解決するための手段］
本発明は、酸性活性基を有する粘弾性体を、該活性基が
発揮する触媒機能により反応変換される物質を含む液体
と共に、高せん断力のかがる条件下に曳糸性を示す状態
に保ちつつ混練することを特徴とする、粘弾性体を用い
る新規な反応方法を提供するものである。[Means for Solving the Problems] The present invention provides a method in which a viscoelastic body having an acidic active group is subjected to a high shear force together with a liquid containing a substance that is reacted and converted by the catalytic function exerted by the active group. The object of the present invention is to provide a novel reaction method using a viscoelastic material, which is characterized by kneading while maintaining a state in which the material exhibits stringiness at the bottom.
本発明の酸性活性を示す酸性活性基は、硫酸、燐酸、炭
酸などの残基を有するものであり、例え゛ば、スルホン
酸基、カルボン酸基、燐酸エステル残基なとである。こ
れらの酸性活性基は、粘弾性体の種類に応じて、例えば
、従来から公知である反応を適宜に組み合せて粘弾性体
に導入することができる。また、反応によって導入する
他に、例えば、従来のイオン交換樹脂で行なわれるアク
リル酸、メタクリル酸など重合する物質を共重合して導
入してもよい。The acidic active group exhibiting acidic activity of the present invention has a residue of sulfuric acid, phosphoric acid, carbonic acid, etc., such as a sulfonic acid group, a carboxylic acid group, and a phosphoric acid ester residue. These acidic active groups can be introduced into the viscoelastic body by, for example, appropriately combining conventionally known reactions depending on the type of the viscoelastic body. In addition to introducing by reaction, for example, a polymerizable substance such as acrylic acid or methacrylic acid may be copolymerized and introduced using conventional ion exchange resins.
曳糸性とは力のかからない状態では弾性を示すほど高粘
性の物質が、高せん断の条件下で混練されたときに、粘
性により糸を引きながら大きく変形することをいう。高
せん断力で混練されたとき曳糸性を示すような、弾性と
粘性とを兼ねそなえた性質を示すものを粘弾性体という
。本発明の粘弾性体は、高せん断の条件下で曳糸性を示
すものであればよい。このように、せん断力のかからな
い状態では弾性を示し、せん断力かかかる状態では粘性
を示すものの例としては、アスファルト、コールタール
ピッチ、ロジンなどのような天然物質、ポリビニルアル
コール、部分鹸化されたポリビニルアルコール、ポリビ
ニルブチラールのようなビニル樹脂など合成された樹脂
状物質がある。Threadability refers to the fact that a substance that is so viscous that it exhibits elasticity when no force is applied, when kneaded under conditions of high shear, is greatly deformed by pulling the string due to its viscosity. A substance that exhibits properties that combine elasticity and viscosity, such as exhibiting stringiness when kneaded with high shear force, is called a viscoelastic substance. The viscoelastic body of the present invention may be one that exhibits stringiness under high shear conditions. Examples of materials that exhibit elasticity in the absence of shear force and viscosity in the presence of shear force include asphalt, coal tar pitch, natural substances such as rosin, polyvinyl alcohol, partially saponified polyvinyl There are synthetic resinous substances such as alcohol and vinyl resins such as polyvinyl butyral.
これらは何れも、高せん断力のかからない状態では見か
け上置体と見なせるほどの弾性を示すが、せん断力のか
かる状態では粘性を示すようになり、混練することによ
り曳糸性を示しながら大きく変形する。In the absence of high shear force, these materials exhibit enough elasticity that they can be regarded as apparent objects, but in the presence of shear force, they become viscous, and when kneaded, they deform significantly while exhibiting stringiness. do.
また、混練された状態における曳糸性を更に良好に保つ
ために、軟化剤として溶剤を用いこれらを希釈すること
もできる。希釈剤として用いる溶剤は、長時間の混練で
蒸発飛散しないように沸点の高いものが好ましい。具体
的には、灯油、軽油、タービン油、重油などが例示され
る。Further, in order to maintain even better stringability in the kneaded state, a solvent can be used as a softener to dilute these. The solvent used as the diluent is preferably one with a high boiling point so as not to evaporate and scatter during long-time kneading. Specifically, kerosene, light oil, turbine oil, heavy oil, etc. are exemplified.
本発明の粘弾性体は、酸性活性基を有する単独の粘弾性
体の他、酸性活性基を持たない粘弾性体と１昆合使用し
てもよい。The viscoelastic body of the present invention may be used alone or in combination with a viscoelastic body that does not have an acidic active group.
反応変換対象物質は、本発明の粘弾性体に親和性のない
溶媒に含まれ液体状になっている。すなわち、液体の状
態で、例えば、エマルジョン、サスペンションの状態あ
るいは溶解した状態のものである。これらを含む溶媒は
、水、アルコール、ケトン、エーテルなどである。アル
コールは、メタノール、エタノール、イソプロパツール
などの低級アルコール、またはエチレングリコール、プ
ロピレングリコール、グリセリンなどの多価アルコール
が好ましい。ケトンは、アセトンやメチルエチルケトン
などのように炭素数の少ないものが好ましい。エーテル
としては、テトラヒドロフラン、ジオキサン、セロソル
ブなどがある。また、これらの含酸素炭化水素系溶媒の
他に、ジメチルホルムアミド、ジメチルスルホキシド、
スルホランなどのように含窒素、含硫黄系の極性溶媒で
、水によく溶解するものでもよい。これらは何れも高い
極性を持つものであり、酸性触媒活性を有する粘弾性体
に対して溶解性を持たないか、親和性のないものである
。The substance to be reacted and transformed is contained in a solvent that has no affinity with the viscoelastic body of the present invention, and is in a liquid state. That is, it is in a liquid state, for example, an emulsion, a suspension, or a dissolved state. Solvents containing these include water, alcohol, ketone, ether, and the like. The alcohol is preferably a lower alcohol such as methanol, ethanol or isopropanol, or a polyhydric alcohol such as ethylene glycol, propylene glycol or glycerin. The ketone preferably has a small number of carbon atoms, such as acetone or methyl ethyl ketone. Ethers include tetrahydrofuran, dioxane, and cellosolve. In addition to these oxygen-containing hydrocarbon solvents, dimethylformamide, dimethyl sulfoxide,
A nitrogen-containing or sulfur-containing polar solvent such as sulfolane that is well soluble in water may also be used. All of these have high polarity and have no solubility or affinity for viscoelastic bodies having acidic catalytic activity.
本発明においては、酸性活性を有する粘弾性体は、高せ
ん断力条件下で混練されるため、常に大きな変形力を受
け、反応対象物質との接触面は常に更新される。これに
より反応効率は常に良好な状態に保たれる。更に本発明
の方法では、酸性活性基を活性化させるために、金属イ
オンを添加する必要もなく、賦活することもなく触媒活
性を示す。従って金属イオンによって中和された酸性活
性基を再び賦活する必要もなく、長期間安定した酸性活
性状態に保つことができる。In the present invention, since the viscoelastic body having acidic activity is kneaded under high shear force conditions, it is constantly subjected to a large deformation force, and the contact surface with the reaction target substance is constantly renewed. This ensures that the reaction efficiency is always maintained at a good level. Furthermore, in the method of the present invention, there is no need to add metal ions to activate the acidic active groups, and the catalyst exhibits catalytic activity without activation. Therefore, there is no need to reactivate acidic active groups that have been neutralized by metal ions, and a stable acidic active state can be maintained for a long period of time.
本発明の変換対象物は、非親和性液体に含まれ混練され
て粘弾性体との接触により変換される。The object to be converted according to the present invention is contained in a non-affinity liquid, kneaded, and converted by contacting with a viscoelastic body.
本発明の方法を実際に実施する場合、粘弾性体中の酸性
活性基に、吸着し不活性化する恐れのある金属カチオン
が共存することもある。この場合には、ｔめ反応対象物
を含む液体を処理し、イオンを除去しておくこともでき
る。これらの処理の方法としては、従来のイオン交換樹
脂による処理、イオンを不溶性の物質に変換して除く方
法などの従来の液体からイオンを除く技術が適宜選択で
きる。When the method of the present invention is actually carried out, metal cations that may be adsorbed to the acidic active groups in the viscoelastic body and become inactivated may coexist. In this case, the liquid containing the second reaction target may be treated to remove ions. As methods for these treatments, conventional techniques for removing ions from a liquid can be selected as appropriate, such as treatment using a conventional ion exchange resin or a method for removing ions by converting them into an insoluble substance.
また、本発明の粘弾性体中の酸性活性基が、既に吸着金
属イオンで不活性化されているときには、例えば、鉱酸
で処理して該吸着金属イオンを洗浄除去する方法などで
活性化することもできる。Furthermore, when the acidic active groups in the viscoelastic body of the present invention have already been inactivated by adsorbed metal ions, they can be activated by, for example, a method of treating with mineral acid to wash and remove the adsorbed metal ions. You can also do that.
゛ また、粘弾性体に含まれる酸触媒活性基は結合して
おり湧出しない。このために反応はほぼ中性の条件下で
行なうことができ、装置の腐食などの問題点もない。゛ Also, the acid catalyst active groups contained in the viscoelastic body are bonded and do not come out. Therefore, the reaction can be carried out under substantially neutral conditions, and there are no problems such as corrosion of equipment.
高せん断力の条件下に曳糸性を示す状態に保って混練す
るためには、ニーダ−、エクストルーダー、バンバリー
ミキサ−などの目的に応じて通常の混練機を使用すれば
よい。また、これらの混練機には目的に応じて、適宜に
加熱や冷却できる構造を付与することもできる。In order to knead while maintaining stringability under conditions of high shearing force, a conventional kneader such as a kneader, extruder, Banbury mixer, etc. may be used depending on the purpose. Furthermore, depending on the purpose, these kneaders can be provided with a structure capable of heating or cooling as appropriate.
［発明の効果］
本発明の方法によれば、従来過酷な条件を必要とした酸
性活性による反応が、常温常圧でしかも実際上はほぼ中
性という非常に穏和な条件で達成でき、装置の腐食を防
ぐことができる。[Effects of the Invention] According to the method of the present invention, the reaction by acidic activity, which conventionally required harsh conditions, can be achieved under very mild conditions of room temperature and normal pressure, and is actually almost neutral. Can prevent corrosion.
以下に酸性活性反応として、カルボン酸エステルの加水
分解、アルコールとカルボン酸のエステル化反応および
アルデヒドの二量化であるアルドール縮合反応を例にと
り実施例によって説明する。Examples of the acidic activation reaction will be described below, taking as examples hydrolysis of carboxylic acid ester, esterification reaction of alcohol and carboxylic acid, and aldol condensation reaction, which is dimerization of aldehyde.
［実施例］
参考例１ニアスフアルドのスルホン化
針入度６０から８０のストレートアスファルト４００ｇ
を、シクロヘキサン１．５１に溶解して、温度を５０か
ら５５℃に保ち、３０ｇの濃硫酸を徐々に加えてスルホ
ン化した。その後約２時間更に反応させ、反応終了後、
更にｉｎのシクロヘキサンを加えて廃硫酸層を静置分離
し、洗浄水が中性になるまで洗浄した。その後、溶媒の
シクロヘキサンを減圧で蒸留分離し、スルホン化アスフ
ァルトを得た。スルホン化率は、スルホン酸含有量で３
．２重量％であった。[Example] Reference Example 1 400 g of straight asphalt with Niasphald sulfonation penetration of 60 to 80
was dissolved in 1.5 l of cyclohexane and sulfonated by slowly adding 30 g of concentrated sulfuric acid while keeping the temperature at 50-55°C. After that, the reaction was continued for about 2 hours, and after the reaction was completed,
Furthermore, cyclohexane was added thereto, and the waste sulfuric acid layer was separated by standing and washed until the washing water became neutral. Thereafter, the solvent cyclohexane was distilled off under reduced pressure to obtain sulfonated asphalt. The sulfonation rate is 3 based on the sulfonic acid content.
．． It was 2% by weight.
参考例２：イソブチレン重合体のスルホン化インブチレ
ンの重合体である日本石油化学■製テトラックス３Ｔ（
粘度平均分子量３００００） ４００ｇを１．５２のｎ
−ヘキサンに溶解し、温度を４０から５０℃に保って、
３０％の発煙硫酸を徐々に加えてスルホン化した。発煙
硫酸はテトラックス３Ｔに対して、Ｓ０３として５倍モ
ルになるように添加した。反応後は参考例１に準じて洗
浄処理を行なった。スルホン化率は６５モル％であった
。Reference example 2: Sulfonation of isobutylene polymer Tetrax 3T manufactured by Nippon Petrochemical Corporation, which is a polymer of imbutylene (
Viscosity average molecular weight 30000) 400g to 1.52n
- dissolved in hexane and keeping the temperature between 40 and 50 °C,
Sulfonation was carried out by gradually adding 30% oleum. Fuming sulfuric acid was added to Tetrax 3T in a 5-fold molar amount as S03. After the reaction, washing treatment was performed according to Reference Example 1. The sulfonation rate was 65 mol%.
実施例１：酢酸メチルの加水分解
２７０ｇのスルホン化アスファルトと３０ｇの灯油と１
４０ｇの水とを、容量１リツトルの二輪式ニーダ−で、
温度４０から４５℃に保って混練した。混練によって上
記混合物は比較的良好な曳糸性を示した。Example 1: Hydrolysis of methyl acetate 270 g of sulfonated asphalt, 30 g of kerosene and 1
40g of water in a two-wheeled kneader with a capacity of 1 liter,
The mixture was kneaded while maintaining the temperature at 40 to 45°C. Upon kneading, the above mixture exhibited relatively good spinnability.
次に、１５ｇの酢酸メチルおよび更に１６０ｇの水をニ
ーダ−に供給し混練した。水層中の酢酸メチルの減少量
および加水分解によって生成したメタノールの増加量を
分析して、加水分解率を調べた。その結果、酢酸メチル
の添加からの経過時間２．４．８．１２時間における酢
酸メチルの加水分解率は、各々１１．２６．３２．３４
モル％であった。Next, 15 g of methyl acetate and further 160 g of water were fed into a kneader and kneaded. The hydrolysis rate was determined by analyzing the decrease in methyl acetate in the aqueous layer and the increase in methanol produced by hydrolysis. As a result, the hydrolysis rates of methyl acetate at the elapsed time of 2, 4, 8, and 12 hours from the addition of methyl acetate were 11, 26, 32, and 34, respectively.
It was mol%.
実施例２：酢酸メチルの加水分解
実施例１で用いたスルホン化アスファルトと灯油の代わ
りに、３００ｇのスルホン化テトラックス３Ｔを用いて
、酢酸メチルの加水分解を行なった。混合物と水とを混
練したときは、実施例１と同様に良好な曳糸性を示した
。反応開始後、２．４．８．１２時時間口おける加水分
解率は、各々６．１２．１７．１８モル％であった。Example 2: Hydrolysis of Methyl Acetate Methyl acetate was hydrolyzed using 300 g of sulfonated Tetrax 3T instead of the sulfonated asphalt and kerosene used in Example 1. When the mixture and water were kneaded, similar to Example 1, good stringability was exhibited. The hydrolysis rates at 2, 4, 8, and 12 hours after the start of the reaction were 6, 12, 17, and 18 mol%, respectively.
実施例３ニステアリン酸メチルの加水分解１３０ｇのス
ルホン化アスファルト、１４０ｇのアスファルトおよび
３０ｇの灯油からなる混合物と１５０ｇの水とを、容量
１リツトルの二軸式ニーダ−で、温度を４５から５０℃
に保って混練した。混練によって上記の混合物は良好な
曳糸性を示した。Example 3 Hydrolysis of methyl nistearate A mixture of 130 g of sulfonated asphalt, 140 g of asphalt and 30 g of kerosene was mixed with 150 g of water in a 1 liter twin-screw kneader at a temperature of 45 to 50°C.
The mixture was kept at a constant temperature and kneaded. Upon kneading, the above mixture exhibited good spinnability.
次に、１５ｇのステアリン酸メチルおよび更に２００ｇ
の水をニーダ−に供給し混練した。加水分解によって生
成し、水層に湧出したメタノールの増加量を分析して加
水分解率を調べた。その結果、ステアリン酸メチルの添
加からの経過時間、２．４．８．１２時間におけるステ
アリン酸メチルの加水分解率は、各々、４．１３．３７
．４９モル％であった。Then 15g methyl stearate and a further 200g
of water was supplied to the kneader and kneaded. The rate of hydrolysis was determined by analyzing the increase in methanol produced by hydrolysis and flowing into the aqueous layer. As a result, the hydrolysis rate of methyl stearate at 2,4,8, and 12 hours after the addition of methyl stearate was 4,13,37, respectively.
．． It was 49 mol%.
実施例４：フタル酸ジメチルの加水分解ステアリン酸メ
チルの代わりにフタル酸ジメチルを用いて、実施例３と
同様に、フタル酸ジメチルの加水分解を行なった。その
結果、フタル酸ジメチルの添加からの経過時間８時間後
における、フタル酸ジメチルの加水分解率は５５モル％
であった。Example 4: Hydrolysis of dimethyl phthalate Dimethyl phthalate was hydrolyzed in the same manner as in Example 3, using dimethyl phthalate instead of methyl stearate. As a result, the hydrolysis rate of dimethyl phthalate was 55 mol% after 8 hours from the addition of dimethyl phthalate.
Met.
実施例５：酢酸メチルの加水分解
一実施例１て用いたスルホン化アスファルトと灯油の混
合物の代わりに、
（Ａ）１５０ｇのスルホン化アスファルトおよび１５０
ｇの低針人度のタールピッチの混合物、（Ｂ）１５０ｇ
のスルホン化アスファルト、１１０ｇのポリビニルブチ
ラール、および４０ｇの軽油の混合物、
を用いて、実施例１と同様にして酢酸メチルの加水分解
を行なった。加水分解反応開始後８時間における加水分
解率は、各々、２８および２２モル％であった。Example 5: Hydrolysis of Methyl Acetate - Instead of the mixture of sulfonated asphalt and kerosene used in Example 1, (A) 150 g of sulfonated asphalt and 150 g of sulfonated asphalt and kerosene were used.
g of low needle strength tar pitch mixture, (B) 150 g
Hydrolysis of methyl acetate was carried out in the same manner as in Example 1 using a mixture of sulfonated asphalt, 110 g of polyvinyl butyral, and 40 g of light oil. The hydrolysis rates 8 hours after the start of the hydrolysis reaction were 28 and 22 mol%, respectively.
実施例６：エステル化反応
３００ｇのスルホン化テトラックスおよび１４０ｇの水
を二軸式のニーダ−にいれて、温度４５℃て混練し、続
いて１３ｇのメタノールおよび１２ｇの酢酸を１００ｇ
の水に溶解し、ニーダ−に添加した。添加後４時間にお
いて、分離している水溶液中の酢酸メチルの生成量を測
定したところ３７モル％のエステル化率であった。Example 6: Esterification reaction 300g of sulfonated Tetrax and 140g of water were placed in a twin-screw kneader and kneaded at a temperature of 45°C, followed by 100g of 13g of methanol and 12g of acetic acid.
of water and added to a kneader. Four hours after the addition, the amount of methyl acetate produced in the separated aqueous solution was measured, and the esterification rate was 37 mol%.
実施例７：アセトアルデヒドの反応
実施例６と同様に、′水とスルホン化テトラックスとを
混練し、１０重量％のアセトアルデヒド水溶液１４０ｇ
を添加し混練した。添加後４時間口に、分離している水
溶液中のアルドールの生成量を測定したところ３４モル
％の反応率であった。Example 7: Reaction of acetaldehyde In the same manner as in Example 6, water and sulfonated tetrax were kneaded to form 140 g of a 10% by weight acetaldehyde aqueous solution.
was added and kneaded. Four hours after the addition, the amount of aldol produced in the separated aqueous solution was measured, and the reaction rate was 34 mol%.
Claims (1)
する触媒機能により反応変換される物質を含む液体と共
に、高せん断力のかかる条件下に曳糸性を示す状態に保
ちつつ混練することを特徴とする粘弾性体を用いる反応
方法。(1) A viscoelastic material having acidic active groups is kneaded with a liquid containing a substance that is reacted and converted by the catalytic function exerted by the active groups while maintaining stringiness under conditions of high shear force. A reaction method using a viscoelastic body characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62042040A JP2521079B2 (en) | 1987-02-25 | 1987-02-25 | Reaction method using viscoelastic body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62042040A JP2521079B2 (en) | 1987-02-25 | 1987-02-25 | Reaction method using viscoelastic body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63209749A true JPS63209749A (en) | 1988-08-31 |
| JP2521079B2 JP2521079B2 (en) | 1996-07-31 |
Family
ID=12625024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62042040A Expired - Lifetime JP2521079B2 (en) | 1987-02-25 | 1987-02-25 | Reaction method using viscoelastic body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2521079B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103933985A (en) * | 2013-01-18 | 2014-07-23 | 济南大学 | Fused iron catalyst used for industrial synthetic ammonia and prepared from sulfuric acid residue |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6071732B2 (en) * | 2013-04-30 | 2017-02-01 | 日本ドライブイット株式会社 | Stud housing |
| JP6071731B2 (en) * | 2013-04-30 | 2017-02-01 | 日本ドライブイット株式会社 | Stud storage pipe valve structure |
-
1987
- 1987-02-25 JP JP62042040A patent/JP2521079B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103933985A (en) * | 2013-01-18 | 2014-07-23 | 济南大学 | Fused iron catalyst used for industrial synthetic ammonia and prepared from sulfuric acid residue |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2521079B2 (en) | 1996-07-31 |
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