| 論文目次 |
目錄 I
圖目錄 V
表目錄 XIII
第一章 前言 1
1-1 研究緣起 1
1-2 研究目的及內容 2
第二章 文獻回顧 4
2-1 土壤基本性質及作用機制 4
2-1-1 土壤有機質 4
2-1-2 腐植質之形成機制 5
2-1-3 土壤中影響有機污染物傳輸之因子 7
2-2 氯酚類化合物介紹 12
2-2-1 氯酚化合物之來源、性質及特性 12
2-2-2 國內氯酚化合物相關管制法規 14
2-2-3 氯酚化合物之毒性及危害 15
2-2-4 土壤中氯酚化合物之處理技術 15
2-2-5 水中氯酚化合物之處理技術 17
2-3 酵素(Enzyme) 21
2-3-1 特性與種類 22
2-3-2 Laccase 24
2-3-3 Peroxidase 26
2-3-4 影響土壤/地下水微生物胞外酵素活性之環境因子 27
2-3-5 酵素之應用 30
2-3-6 酵素在環工上的應用 31
2-4 偶合反應(oxidative-coupling) 32
2-4-1 傅里德－克拉夫茨反應(Friedel－Crafts reaction) 33
2-4-2 酵素於偶合作用扮演之角色 33
2-4-3 酵素於酚類偶合作用過程中可能之機制 35
第三章 實驗方法 39
3-1 實驗內容 39
3-2 實驗設備與儀器 41
3-3 實驗材料 48
3-3-1 土壤 48
3-3-2 溶劑 48
3-3-3 氯酚標準品 50
3-3-4 酵素 52
3-3-5 其他 52
3-4 實驗方法 54
3-4-1 土壤選擇 54
3-4-2 土壤性質分析與調整 56
3-4-3 酵素活性分析 60
3-4-4 不同時間酵素對氯酚水溶液催化反應之影響 61
3-4-5 不同酵素活性對氯酚水溶液催化反應之影響 61
3-4-6 不同時間酵素對氯酚土壤催化反應之影響 62
3-4-7 不同酵素活性對氯酚土壤催化反應之影響 62
第四章 結果與討論 63
4-1 氯酚水溶液之催化實驗 63
4-1-1 溶劑影響酵素活性之測試 63
4-1-2 Laccase氧化還原電位之測試 64
4-1-3 不同時間酵素對氯酚之偶合反應 65
4-1-4 不同酵素活性對氯酚去除之影響 70
4-1-5 LC-MS鑑定偶合產物 74
4-1-6 不同時間酵素對氯酚水溶液之偶合反應 81
4-1-7 不同酵素活性對氯酚水溶液之偶合反應 84
4-2 酵素催化偶合土壤中氯酚之前置實驗 88
4-2-1 索式萃取土壤中氯酚回收率之測定 88
4-2-2 土壤中氯酚於自然環境中之揮發試驗 90
4-3 不同條件下酵素催化土壤中氯酚之反應 95
4-3-1 不同時間酵素對氯酚土壤催化之影響 95
4-3-2 土壤含水率對酵素催化氯酚之影響 107
4-3-3 不同酵素活性對氯酚土壤催化反應之影響 111
4-3-4 土壤有機質含量對酵素催化之影響 118
4-4 酵素催化氯酚土壤偶合反應之產物 121
4-4-1 不同時間酵素對氯酚土壤偶合產物之影響 124
4-4-2 不同酵素活性對氯酚土壤偶合產物之影響 130
4-4-3 不同土壤含水率下酵素對氯酚土壤偶合產物之影響 136
4-4-4 不同土壤有機質含量對酵素偶合氯酚土壤之影響 137
4-4-5 LC-MS鑑定偶合產物 140
第五章 結論與建議 152
5-1 結論 152
5-2 建議 153
參考文獻 155
圖目錄
圖2-1 腐植質之有機質分解及形成 6
圖2-2 Laccase之可能反應機制示意圖 25
圖2-3 Laccase與基質ABTS催化反應圖 25
圖2-4 Peroxidase之反應示意圖 26
圖2-5 受質濃度與反應速率之關係圖 28
圖2-6 傅－克反應：(1)傅－克烷基化：(2)傅－克醯基化反應 33
圖2-7 Laccase催化酚類氫氧基示意圖 34
圖2-8 Peroxidase催化酚類氫氧基示意圖 34
圖2-9 苯酚類C-O鍵及C-C鍵偶合可能之反應機制圖 36
圖2-10 苯酚類C-O鍵偶合可能之反應機制圖 37
圖2-11 酵素催化氧化2,4-dichlorophenol生成自由基偶合可能之反應機制圖 38
圖3-1 研究流程圖 40
圖3-2 索式萃取裝置圖 45
圖3-3 減壓濃縮裝置圖 46
圖3-4 氮氣吹除裝置圖 47
圖3-5 丙酮結構圖 49
圖3-6 甲醇結構圖 49
圖3-7 2,4-二氯酚結構圖 50
圖3-8 2,4,6-三氯酚結構圖 50
圖3-9 2,3,4,5-四氯酚結 51
圖3-10 五氯酚結構圖 51
圖3-11 ABTS結構圖 52
圖3-12 氯酚污染土壤製備流程圖 59
圖3-13 酵素活性測試流程圖 60
圖3-14 不同活性酵素催化氯酚水溶液實驗流程 61
圖3-15 酵素催化氯酚污染土壤實驗流程 62
圖4-1 酵素於不同溶劑中之相對活性 63
圖4-2 不同ABTS添加量對五氯酚偶合反應之影響 64
圖4-3 Laccase偶合2,3,4,5-四氯酚產物液相層析儀圖譜 65
圖4-4 Peroxidase偶合2,3,4,5-四氯酚產物液相層析儀圖譜 66
圖4-5 Laccase偶合五氯酚產物液相層析儀圖譜 66
圖4-6 Peroxidase偶合五氯酚產物液相層析儀圖譜 66
圖4-7 Peroxidase隨不同時間催化2,3,4,5-四氯酚偶合曲線 68
圖4-8 Laccase隨不同時間催化2,3,4,5-四氯酚偶合曲線 69
圖4-9 Peroxidase隨不同時間催化五氯酚偶合曲線 69
圖4-10 Laccase隨不同時間催化五氯酚偶合曲線 70
圖4-11 不同活性Peroxidase催化2,3,4,5-四氯酚水溶液偶合曲線(反應5分鐘) 71
圖4-12 不同活性Peroxidase催化2,3,4,5-四氯酚水溶液偶合曲線(反應1小時) 71
圖4-13 不同活性Laccase催化2,3,4,5-四氯酚水溶液偶合曲線(反應1小時) 72
圖4-14 不同活性Laccase催化2,3,4,5-四氯酚水溶液偶合曲線(反應24小時) 72
圖4-15 不同活性Peroxidase催化五氯酚水溶液偶合曲線(反應5分鐘) 73
圖4-16 不同活性Laccase催化五氯酚水溶液偶合曲線(反應1小時) 73
圖4-17 2,3,4,5-四氯酚水溶液質譜圖 74
圖4-18 2,3,4,5-四氯酚水溶液MS圖 75
圖4-19 Peroxidase催化2,3,4,5-四氯酚水溶液偶合產物質譜圖 75
圖4-20 1 U/ml Peroxidase催化2,3,4,5-四氯酚水溶液 D偶合產物MS圖 76
圖4-21 1 U/ml Peroxidase催化2,3,4,5-四氯酚水溶液E偶合產物MS圖 76
圖4-22 6 U/ml Peroxidase催化2,3,4,5-四氯酚水溶液D偶合產物MS圖 77
圖4-23 6 U/ml Peroxidase催化2,3,4,5-四氯酚水溶液E偶合產物MS圖 77
圖4-24 6 U/ml Peroxidase催化2,3,4,5-四氯酚水溶液F偶合產物MS圖 78
圖4-25 Laccase催化2,3,4,5-四氯酚水溶液偶合產物質譜圖 79
圖4-26 6 U/ml Laccase催化2,3,4,5-四氯酚水溶液A偶合產物MS圖 79
圖4-27 6 U/ml Laccase催化2,3,4,5-四氯酚水溶液B偶合產物MS圖 79
圖4-28 6 U/ml Laccase催化2,3,4,5-四氯酚水溶液C偶合產物MS圖 80
圖4-29 1 U/ml Peroxidase催化五氯酚水溶液G偶合產物MS圖 80
圖4-30 1 U/ml Laccase催化五氯酚水溶液H偶合產物MS圖 81
圖4-31 Peroxidase催化2,3,4,5-四氯酚水溶液偶合產物相對產量趨勢圖 82
圖4-32 Laccase催化2,3,4,5-四氯酚水溶液偶合產物相對產量趨勢圖 82
圖4-33 Peroxidase催化五氯酚水溶液偶合產物相對產量趨勢圖 83
圖4-34 Laccase催化五氯酚水溶液偶合產物相對產量趨勢圖 83
圖4-35 Peroxidase催化2,3,4,5-四氯酚水溶液偶合產物相對產量趨勢圖(反應5分鐘) 85
圖4-36 Peroxidase催化2,3,4,5-四氯酚水溶液偶合產物相對產量趨勢圖(反應60分鐘) 85
圖4-37 Laccase催化2,3,4,5-四氯酚水溶液偶合產物相對產量趨勢圖(反應1小時) 86
圖4-38 Laccase催化2,3,4,5-四氯酚水溶液偶合產物相對產量趨勢圖(反應24小時) 86
圖4-39 Peroxidase催化五氯酚水溶液偶合產物相對產量趨勢圖(反應5分鐘) 87
圖4-40 Laccase催化五氯酚水溶液偶合產物相對產量趨勢圖(反應60分鐘) 88
圖4-41 未滅菌土壤置於加蓋血清瓶中於不同時間之2,4-二氯酚剩餘濃度 91
圖4-42 未滅菌土壤置於燒杯中於不同時間之2,4-二氯酚剩餘濃度 91
圖4-43 滅菌土壤置於加蓋血清瓶中於不同時間之2,4-二氯酚剩餘濃度 92
圖4-44 滅菌土壤置於燒杯中於不同時間之2,4-二氯酚剩餘濃度 92
圖4-45 未滅菌土壤置於加蓋血清瓶中於不同時間之2,4,6-三氯酚剩餘濃度 93
圖4-46 未滅菌土壤置於燒杯中於不同時間之2,4,6-三氯酚剩餘濃度 93
圖4-47 滅菌土壤置於加蓋血清瓶中於不同時間之2,4,6-三氯酚剩餘濃度 94
圖4-48 滅菌土壤置於燒杯中於不同時間之2,4,6-三氯酚剩餘濃度 94
圖4-49 Peroxidase催化紗帽山2,4-二氯酚污染土壤偶合曲線 95
圖4-50 Peroxidase催化紗帽山2,4,6-三氯酚污染土壤偶合曲線 96
圖4-51 Peroxidase催化紗帽山2,3,4,5-四氯酚污染土壤偶合曲線 97
圖4-52 Peroxidase催化紗帽山五氯酚污染土壤偶合曲線 97
圖4-53 Laccase催化紗帽山2,4-二氯酚污染土壤偶合曲線 99
圖4-54 Laccase催化紗帽山2,4,6-三氯酚污染土壤偶合曲線 99
圖4-55 Laccase催化紗帽山土中2,3,4,5-四氯酚偶合曲線 100
圖4-56 Laccase催化紗帽山土中五氯酚污染土壤偶合曲線 100
圖4-57 Peroxidase催化台中土中2,4-二氯酚偶合曲線 102
圖4-58 Peroxidase催化台中土中2,4,6-三氯酚偶合曲線 102
圖4-59 Peroxidase催化台中土中2,3,4,5-四氯酚偶合曲線 103
圖4-60 Peroxidase催化台中土中五氯酚偶合曲線 103
圖4-61 Laccase催化台中土中2,4-二氯酚偶合曲線 104
圖4-62 Laccase催化台中土中2,4,6-三氯酚偶合曲線 105
圖4-63 Laccase催化台中土中2,3,4,5-四氯酚偶合曲線 105
圖4-64 Laccase催化台中土中五氯酚偶合曲線 106
圖4-65 Peroxidase催化滅菌台中土中2,4 -二氯酚偶合曲線(50ppm) 108
圖4-66 Peroxidase催化未滅菌台中土中2,4 -二氯酚偶合曲線(50ppm) 108
圖4-67 Peroxidase催化滅菌台中土中2,4,6-三氯酚偶合曲線(50ppm) 109
圖4-68 Peroxidase催化未滅菌台中土中2,4,6-三氯酚偶合曲線(50ppm) 110
圖4-69 Peroxidase催化滅菌紗帽山土中2,4 –二氯酚剩餘濃度柱狀圖 112
圖4-70 Peroxidase催化滅菌紗帽山土中2,4,6 -三氯酚剩餘濃度柱狀圖 112
圖4-71 Laccase催化滅菌紗帽山土中2,4 –二氯酚剩餘濃度柱狀圖 113
圖4-72 Laccase催化滅菌紗帽山土中2,4,6 -三氯酚剩餘濃度柱狀圖 113
圖4-73 Peroxidase催化紗帽山土中2,4 –二氯酚剩餘濃度柱狀圖 114
圖4-74 Laccase催化紗帽山土中2,4 –二氯酚剩餘濃度柱狀圖 114
圖4-75 Peroxidase催化紗帽山土中2,4,6 -三氯酚剩餘濃度柱狀圖 115
圖4-76 Laccase催化紗帽山土中2,4,6 -三氯酚剩餘濃度柱狀圖 115
圖4-77 Peroxidase催化紗帽山土中2,3,4,5-四氯酚剩餘濃度柱狀圖 116
圖4-78 Laccase催化紗帽山土中2,3,4,5-四氯酚剩餘濃度柱狀圖 116
圖4-79 Peroxidase催化紗帽山土中五氯酚剩餘濃度柱狀圖 117
圖4-80 Laccase催化紗帽山土中五氯酚剩餘濃度柱狀圖 117
圖4-81 Peroxidase催化不同有機質含量土壤中2,4 –二氯酚剩餘濃度柱狀圖 118
圖4-82 Peroxidase催化不同有機質含量土壤中2,4,6-三氯酚剩餘濃度柱狀圖 119
圖4-83 Laccase催化不同有機質含量土壤中2,4 –二氯酚剩餘濃度柱狀圖 119
圖4-84 Laccase催化不同有機質含量土壤中2,4,6-三氯酚剩餘濃度柱狀圖 120
圖4-85 Peroxidase偶合紗帽山土中2,4-二氯酚之產物圖譜 121
圖4-86 Peroxidase偶合紗帽山土中2,4,6-三氯酚之產物圖譜 121
圖4-87 Peroxidase偶合彰化土中2,4-二氯酚之產物圖譜 122
圖4-88 Peroxidase偶合彰化土中2,4,6-三氯酚之產物圖譜 122
圖4-89 Laccase偶合紗帽山土中2,4-二氯酚之產物圖譜 122
圖4-90 Laccase偶合紗帽山土中2,4,6-三氯酚之產物圖譜 122
圖4-91 Laccase偶合彰化土中2,4-二氯酚之產物圖譜 123
圖4-92 Laccase偶合彰化土中2,4,6-三氯酚之產物圖譜 123
圖4-93 Peroxidase催化滅菌紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 124
圖4-94 Peroxidase催化未滅菌紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 125
圖4-95 Laccase催化滅菌紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 125
圖4-96 Laccase催化未滅菌紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 126
圖4-97 Peroxidase催化滅菌紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量趨勢圖 126
圖4-98 Peroxidase催化滅菌台中土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 127
圖4-99 Peroxidase催化未滅菌台中土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 127
圖4-100 Laccase催化滅菌台中土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 128
圖4-101 Laccase催化未滅菌台中土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量趨勢圖 128
圖4-102 Peroxidase催化紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量柱狀圖 130
圖4-103 Peroxidase催化紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量柱狀圖 131
圖4-104 Laccase催化紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量柱狀圖 131
圖4-105 Laccase催化紗帽山土中2,4-二氯酚及2,4,6-三氯酚偶合產物相對產量柱狀圖 132
圖4-106 Peroxidase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 132
圖4-107 Peroxidase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 133
圖4-108 Peroxidase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 133
圖4-109 Peroxidase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 134
圖4-110 Laccase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 134
圖4-111 Laccase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 135
圖4-112 Laccase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 135
圖4-113 Laccase催化紗帽山土中2,3,4,5-四氯酚及五氯酚偶合產物相對產量柱狀圖 136
圖4-114 Peroxidase催化2,4-二氯酚土壤偶合產物相對產量柱狀圖 137
圖4-115 Peroxidase催化2,4,6-三氯酚土壤偶合產物相對產量柱狀圖 138
圖4-116 Laccase催化2,4-二氯酚土壤偶合產物相對產量柱狀圖 138
圖4-117 Laccase催化2,4,6-三氯酚土壤偶合產物相對產量柱狀圖 139
圖4-118 紗帽山2,4-二氯酚土壤未添加酵素質譜圖 140
圖4-119 紗帽山2,4-二氯酚土壤未添加酵素MS圖 141
圖4-120 紗帽山2,4-二氯酚土壤添加10U/g乾土Peroxidase偶合產物質譜圖 141
圖4-121 紗帽山2,4-二氯酚土壤添加10U/g乾土Peroxidase偶合產物MS圖 142
圖4-122 紗帽山2,4-二氯酚土壤添加30U/g乾土Laccase偶合產物質譜圖 143
圖4-123 紗帽山2,4-二氯酚土壤添加30U/g乾土Laccase偶合產物MS圖 143
圖4-124 紗帽山2,4,6-三氯酚土壤未添加酵素質譜圖 144
圖4-125 紗帽山2,4,6-三氯酚土壤未添加酵素MS圖 145
圖4-126 紗帽山2,4,6-三氯酚土壤添加5U/g乾土Peroxidase偶合產物質譜圖 145
圖4-127 紗帽山2,4,6-三氯酚土壤添加5U/g乾土Peroxidase偶合產物MS圖 146
圖4-128 紗帽山2,4,6-三氯酚土壤添加5U/g乾土Laccase偶合產物質譜圖 146
圖4-129 紗帽山2,4,6-三氯酚土壤添加5U/g乾土Laccase偶合產物MS圖 147
圖4-130 紗帽山2,4-二氯酚與2,4,6-三氯酚土壤添加20U/g乾土Peroxidase偶合產物MS圖 148
圖4-131 紗帽山2,4-二氯酚與2,4,6-三氯酚土壤添加20U/g乾土Peroxidase偶合產物MS圖 148
圖4-132 紗帽山2,4-二氯酚與2,4,6-三氯酚土壤添加20U/g乾土Laccase偶合產物MS圖 149
圖4-133 台中土2,4-二氯酚與2,4,6-三氯酚土壤添加20U/g乾土Peroxidase偶合產物MS圖 149
圖4-134 台中土2,4-二氯酚與2,4,6-三氯酚土壤添加20U/g乾土Peroxidase偶合產物MS圖 150
圖4-135 台中土2,4-二氯酚與2,4,6-三氯酚土壤添加20U/g乾土Laccase偶合產物MS圖 150
圖4-136 紗帽山2,3,4,5-四氯酚及五氯酚土壤添加20U/g乾土Peroxidase偶合產物MS圖 151
圖4-137 台中土2,3,4,5-四氯酚及五氯酚土壤添加20U/g乾土Peroxidase偶合產物MS圖 151
表 目 錄
表2-1 吸附與分佈之比較 7
表2-2 氯酚類化合物之物理化學性質 13
表2-3 氯酚污染物於地下水及土壤中之法規標準值 14
表2-4 IUBMB系統六大分類 22
表2-5 常見的偶合反應 32
表2-6 來源不同之酵素及其可催化偶合之物質 35
表3-1 高效能液相層析儀分析條件 41
表3-2 UPLC-HRMS操作條件 43
表3-3 HPLC-LRMS操作條件 44
表3-4 選用土壤一覽表 48
表3-5 選用土壤之基本性質 55
表3-6 選用土壤之pH值 56
表3-7 選用土壤之初始含水率及田間容水量 58
表4-1 偶合產物代號表 67
表4-2 配置氯酚土壤之回收率 89 |
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